Young Josh went away to college with no friends, plans or dreams for his life. It all comes together for him as Jill but not until a terrible tragedy changes his life.
A Tragic Beginning
by: Teresa Ann Wood
Of course I felt guilty; the opportunity of a lifetime had come to me and even if it turned out to be better than even my wildest dreams that wasn’t the way I had wanted it to happen. I never wanted to profit from someone else’s tragedy.
My name is Josh Benning and I have been a closet crossdresser for most of my young life; living out of the clothes hamper of my female relations and those of my few friends. I was never caught, not once, in all those years of dressing up but that was mainly because I was so cautious. I never once left the bathroom, not even when I knew that I was home alone. I was a coward but with good reason; I’d seen what my father did when my older siblings broke his rules and none of them had ever done anything that would be as bad in my father’s eyes as a boy wearing girl’s clothing. I wanted to dress up, but I wanted to live too.
Anyway I kept my secret all the way through high school and did my best to live a ‘normal’ life in public. I asked out some girls only to be turned down as I was small and apparently completely unattractive to them. I didn’t know why their negative responses were such a relief to me. I thought that I was just scared of going on that first date; I wouldn’t know what to do, how to act, but it reality I just didn’t want to date a woman. Even then I was gay; I just hadn’t admitted it to myself.
My family was poor but I had good enough grades to earn a scholarship to an in-state college. It wasn’t a huge school with tens of thousands of students, but it had enough to maintain most of the major sports teams like football, basketball, baseball, and even soccer. They offered sports scholarships but most were not full scholarships; leaving most of the students to come from very wealthy families. They had a gymnastics team, the only sport I could compete at, and so I had intentions of trying out for it when I got there. My dad wasn’t crazy about it but he was mollified that his ‘sissy’ son was at least going to be competing in a college sport. None of my behemoth brothers had accomplished that.
So off I went, moving from my small rural high school to a community that was just barely large enough to qualify as a city. Lendersville had a population of around 35,000 people, most of which had jobs that were at least indirectly reliant on Lender College. It was a college town, that’s for sure, and all incoming freshmen were made to feel right at home. I certainly was, at least until I met my roommate.
Trent was a conceited jerk, no question about it. In his heart he knew that he was incredibly handsome and the wet dreams of every young woman he met. He was an athlete at Lendersville on a basketball scholarship. At six-foot-three he may have been tall for a point guard, but his ball-handling skills were superb. He had offers from bigger schools but chose Lender College because his family had some sort of legacy there; every one from their family had attended Lender for a hundred or more years, apparently. Trent wasn’t necessarily a cruel guy, but he realized right away that he was the dominant male between us and he simply expected me to do what he said. The worst part of the whole situation was that Trent was every bit as dreamy as he believed, and for the first time I could not deny my attraction to another man. He was mouth-wateringly gorgeous!
As I was planning on trying out for the gymnastics team, I had to arrive at school several weeks early. Trent was already there and before the first week was up I was the one responsible for cleaning our dorm room. I tried to make the best of it and would try to do it when he was gone, so I could slip on a pair of panties (the only female attire I owned and all I dared to keep with me) beneath my regular clothes and pretended to be a woman cleaning the room for myself and my boyfriend (I had it so bad for Trent). I really enjoyed picking up his dirty clothing, particularly his jockstraps, and before long I was doing both our laundry too. In some ways I didn’t mind too much but in others I did; but one peek at his half-clothed body would drive that away. Just about anything was acceptable if it kept us living together; he was so hot! Before long I found myself masturbating daily thinking of him, but unfortunately had never had a chance to catch a peek at his cock. I couldn’t take the chance that he might catch me looking.
Anyway I went out for the gymnastics team, just like I planned. I worked hard for three weeks but in the end I was the last one cut; I had the ability, the coach said, I just didn’t have the experience of the other guys. This was devastating to me since I had really wanted to make the team; not only did I want my father to be proud of me (I’m not sure why) but since Trent had convinced me that I was, in fact, truly gay, I enjoyed the sight of the other male gymnasts dressing or showering after practice. This led to another epiphany for me; I was pitifully endowed.
My dick is tiny, no question. I knew it was smaller than average from some ‘research’ I had done on the internet but I had convinced myself that those men were on there because they were so much larger than normal. Perhaps they were, but even average is apparently far bigger than me. I’ve begun to think of my dick as ‘the smallest in captivity’, as even at full erection I can easily jack-off with two fingers. None of the other gymnasts could match the monsters of the internet, but then again even the smallest of them made an easy three of me. I made sure they didn’t see mine even as I took cautious peeks at theirs.
Needless to say I was really downhearted about not making the team, and dreaded having to tell my parents as I knew my dad wouldn’t take it well. I didn’t have to worry about that, because by the time I went home that next week to break the news; he had died of a massive heart attack. This was devastating to my whole family, even to me; my dad and I didn’t always get along but I knew he only wanted what was best for me in his eyes. Our determination of what was best simply varied too much. He had loved me in his own way, I know that.
I returned to school right after the funeral not because I had to, classes still didn’t start for a long time, but because I wanted to. Home was too depressing, particularly with mom grieving like she was, and I wanted to get back to Trent. Not that he had missed me; he only knew I had been gone because the room hadn’t been cleaned; his days were filled with pickup basketball games and chasing various unattached women. Once I had told him about my dad, however, he became nicer to me and listened as I talked about my grief. It’s amazing what will strike a cord within someone. His own father had died not long before, and that was part of the reason he had came to Lender. He comforted me that first night, not in his arms like I wanted, of course, but we talked most of the night. I loved him all the more for it.
One positive side of my father’s death was that I no longer had to worry quite so much about doing some things that I wanted to; such as letting my hair grow. I had let it grow as much as he would allow before leaving for college and hadn’t touched it since I got here. I was intending to cut it before going home but his death caused me to forget. Now I wouldn’t have to cut it if I didn’t want to; mom wouldn’t care. It grew pretty quickly anyway and so I hoped that by the New Year it would be long enough to reach my shoulders. It was a secret dream of mine to have hair long enough to wear in a ponytail. Certainly it was a feminine hairstyle and yet I could get away with wearing it in public! For me, that was a very brave plan. Who knew if I would ever have the guts to go through with it but I could at least let it grow for awhile to feed the dream. Another positive aspect came a day or two later when I read a notice concerning cheerleader tryouts. There were no scholarships for the cheerleaders so the tryouts were completely open. My heart almost stopped when I realized that I could tryout for the cheerleading squad.
What was stopping me? My dad was gone, he would never have allowed that, and in college there were male cheerleaders all the time. It didn’t carry nearly the stigma that male high school cheerleaders did. Not that my high school would have ever have allowed such a thing. Perhaps I couldn’t make the gymnastic squad, but those same skills just might get me onto the cheerleading squad! Tentatively I mentioned my idea to Trent, who thought it was a great idea.
“You get to look up the cheerleader’s skirts all the time; and they sit right on the palm of your hand when you lift them up in the air,” He chortled. “I would love to be a male cheerleader; they’re bound to get laid all the time if they’re not all queer.”
Trent’s comments emboldened me even as I worried that they were hitting too close to home considering the ‘queer’ comment. He had given me an obvious excuse as to why I wanted to be a cheerleader but even so I was amazed that I had the guts to even consider it. Despite telling myself that I would never go through with it and that it was simply a nice little dream to play around with I found myself in the gymnasium on the first day of tryouts.
I was surprised to see fourteen guys trying out for the four open spots on the squad. There were twice that many girls trying out for only three openings on the girl’s side. At least half the guys were there for the same reasons that Trent had given; they just wanted to get their hands on the girls and so they were quickly weeded out. My tumbling skills got me invited back for the second day but by then it was obvious to me that I simply did not have the strength to do what they needed. I had to be able to lift the females and hold them over my head; it was they who needed the gymnastic skills not the men. Somehow I was invited back the third day with four other guys; I had an eighty percent chance of making it, but at the end of that day the cheerleading coach took me aside and gave me the bad news; I had been cut.
“We’ll keep your name on file, though,” she said, patting me on the shoulder. “If we have an injury we might use you to fill in for the alternate we activate.”
Great. I couldn’t even make it as a full-time alternate. I thanked her and gathered my stuff, delaying as much as possible in the hopes that the other male cheerleaders would come in to shower once more before I left, but I was disappointed in that regard. Most of them were gay just like Trent had joked but for whatever reason those guys didn’t really appeal to me. Not like Trent or the other straight guys did, anyway. When I looked at him, I was immediately aroused. When I looked at the obviously feminine-acting gay men I felt absolutely nothing. At least with women I had some interest in what they were wearing.
I sulked as I left the locker room; apparently college was to be no more successful for me than high school had been, at least not outside the classroom. Most of the gymnasium we had been working out in was empty, the door to the track stood open so they must have been outside running but I noticed one figure sitting near the top of the bleachers on one side. The noise from outside was too loud for me to hear anything but I could tell by the way she was sitting that she was crying. Without thinking too much about it I made my way up the steps to her, approaching quietly so as not to frighten her. That was almost funny to me; no girl was ever frightened of me; I’m smaller than them more often than not. I sat nearby but not threateningly close. I wanted to help but if she didn’t want to speak to me then I would leave.
I recognized her of course; she had been trying out for the cheerleading squad as well, though they had scrupulously kept the men and women apart during most of the tryouts to discourage the horn-dogs that were there just to get a peek up a few skirts. She was quite pretty with red hair and a petite build; she was barely taller than me which was saying something. She had a nice, athletic body and I had thought that she was a shoo-in for the squad. I guess that showed how much I knew. I sat for awhile and was just about to leave when she finally spoke.
“I guess you were cut too,” she sobbed, never once lifting her face from her hands.
I said that I had been and tried to ask her the same question but of course it came out all messed up. Thankfully she was merciful and didn’t take me the wrong way.
“Yes, and it’s not fair! I deserved to make the squad!” she grouched, finally lifting her face and looking at me, daring me to disagree, I supposed.
“I totally agree, you were great,” I said quickly, not wanting to have ‘beaten-up-by-a-cheerleader’ attached to my already weak reputation.
Mollified she calmed down a bit and we began to talk about the unfairness of her plight. I really did agree; she was easily as good at cheerleading as any of the girls that made the squad, and so she found some comfort in my presence. I actually felt better about my own failure as well, just by helping her. That seemed odd to me at the time but I understand it now.
“Do you know why she cut me?” the girl, her name was Debi, demanded at one point. I said no. “Because she’s a lesbian and she only wants girls with big boobs!” she explained, tugging her t-shirt tightly to her body to expose the outline of her breasts. “Do you see anything wrong with these?” she demanded again, glaring at me as if daring me to say that I did. She certainly had the temper to match that hair.
I dutifully looked at the small mounds on her chest, noting that they were likely B-cup unless her clearly visible sports bra was messing with my judgment. Certainly not huge breast but I would love to have them myself.
“No, of course not, they’re great,” I stumbled, looking away from her chest in embarrassment. Had I really thought that I would like to have breasts like hers? “But how do you know that’s why she cut you?”
Debi laughed once, very sharply. “It’s a well-known fact that she’s a lesbian. She was almost fired two years ago for dating one of her cheerleaders. This is my fourth time trying out, and I’ve been the last one cut every year. Now I’m a senior, and this was my last chance. It’s so obvious that she only wants girls with big tits on her squad; if you pay attention to the ones who make the team you’ll see what I mean…” she hesitated, looking a little closer at me.
She suddenly moved closer on the bench, staring intently at me. Not in a threatening way but just very intent. Catching my eyes she also caught my own gaze; I was staring eye to eye at her without the least ability to look away. She was looking into my soul, that’s how I see it now, but then it was very disturbing to say the least. Even in her sorrow she wanted to help me in return.
“You’re gay, aren’t you.” She stated matter-of-fact. My gaze was still captured by hers and I was the only one of us who was surprised to hear my voice say that I was. Perhaps some people might have suspected but no one actually knew. I was mortified over what I had just done!
“Don’t worry, I’m not making fun of you,” she said quickly as she scooted even closer to me on the bench-style bleachers. “I know it had to be tough on you to be cut as well. I can imagine how much you were looking forward to showering with all those cute guys.”
She was teasing me, and for the first time in a life filled with teasing it didn’t hurt; it even felt good. Tearing up myself I shared a little laugh with her and within an hour we were the best of friends.
We spent the next several hours drinking coffee at a little diner and then went back to her dorm until I and any other men visiting had to leave. Then we walked for a while around campus just talking; it was a wonderful evening and completely new to me. I’d never had a close friend and Debi was wonderful. We talked of our disappointments and I talked of being gay and a virgin. She told me about her past boyfriends and her desire to be a cheerleader. Debi promised not to tell anyone about my being gay and for the first time in my life I was able to unburden myself completely. By the time I went back to my own dorm she knew everything there was to know about me; even my desire to crossdress. We agreed to meet for lunch the next day and I could barely sleep I was so excited. Scared and excited. I had told her everything, all my secrets, and if she had been playing me for a fool everyone one campus would soon know. By the time I drifted off to sleep I was frantic with worry. How could I have been so stupid?
But she met me for lunch just like she promised and within minutes I knew that she hadn’t told anyone about my secrets. Indeed I felt that she would never betray me that way and by the time we finished lunch it was almost time for dinner and she had shared such intimate details of her own private life that I knew that my secrets would always be safe with her. Whenever we were alone she started calling me ‘Jill’ but never forgot to call me ‘Josh’ when someone else could overhear.
After dinner we went back to her dorm again, her roommate had not yet arrived for fall classes, and she showed me a smooth plastic dildo she kept locked in her makeup case. She told me about her sexual encounters and confessed that she used the dildo ‘more often than she had to’ because she had never had trouble getting a boyfriend. She told me about giving head, she didn’t enjoy it but had done it a few times for guys she really liked, and told me how wonderful it felt to have her pussy stretched wide by a nice, thick cock and feeling it rubbing against her clit. Naturally this sort of talk turned us both on and after sharing these sort of intimate conversations all that next week it seemed only natural for her to use the dildo on herself in front of me as she explained what felt the best. By the third or fourth time I was even helping her; working the dildo in and out while she played with her clit or cupped her breasts. Sitting through these sessions without even getting hard was the last straw as far as removing my last denial about being gay. I never got excited until she offered to let me try her dildo for myself.
Scared, embarrassed, and surprised, I declined her offer but she wanted to do something for me and so the week before her roommate arrived she finally convinced me to allow her to dress me up completely as a woman; makeup and all, just so I could get the full experience. I was so nervous I almost passed out but I showed up when she told me to, fully shaved from eyebrows to toes, and enjoyed a glorious evening trying on her clothes. We were very nearly the same size, even her bras fit me perfectly though I couldn’t fill the cups, and I must have tried on every outfit she had twice over. I adored her stockings and when I left that night she insisted that I wear a pair of pantyhose home ‘just to get used to them,’ she giggled. We did this every evening until her roommate arrived and I graduated to wearing her panties full-time. Not easy to keep out of Trent’s sight but I managed it well enough. That last weekend we went shopping together, me dressed as a man except for my panties, and she bought a lot of clothing for me as her family was wealthy and she had her own charge cards. She kept the clothes in her dorm for me but with her roommate due to arrive soon we both knew that my dressing opportunities would soon end. That was when she got the news.
Lender College had a mascot, like all colleges I guess, and ours was a Puma. It was a big, angry looking feline with a trademark LC ball cap on its head. Naturally images of it were everywhere on campus, complete with such statements as ‘Puma Pride’ and ‘Go Pumas’. Debi’s roommate had arrived and classes were only a day or two away from starting when Ms. Chlebowski came to see Debi and offer her a place on the squad. She wasn’t nearly as excited as I thought that she would be.
“The mascot?” she grouched. “I don’t want to wear that stuffy old costume, that’s not real cheerleading!”
“Yes it is,” I argued, sipping at my coffee. The diner had become our regular hangout now that her roommate was there. “It may not be the same as having some guy’s hand up your butt all day but you’re still cheering your team on to victory!”
That at least made her giggle and eventually she accepted the position. It certainly wasn’t her dream but finally she agreed that it might be fun but only if I agreed to attend every game that she did. I agreed, what else did I have to do? Study and watch her was about it. I still had no social life that didn’t involve her. Trent thought we were dating as it was.
So Debi became the new Lender College mascot, dressing up in that ratty old puma costume and practicing for hours each day as ‘Lendy’. Fall classes began in mid September but the first football game was more than a week before that. She had to attend all the home games for football, basketball and soccer for both the men’s and women’s programs and had to at least make three appearances each for softball and baseball in the spring. That was far more than the regular cheerleading squad had to do, as they were only required to attend home games for football and basketball plus their own ‘cheer’ tournaments. Being such a small university, we didn’t have varsity and JV cheer squads, nor a pep squad and the like to handle all the sporting events, and only one mascot suit as well. By halftime of that first football game, we lost something like 37-17; I knew that Debi enjoyed being Lendy a great deal.
Now Debi had more demands on her time but she still made room for me. I came over and helped her with her homework, even though she was a senior and I was a freshman, I was a better student that she was. I didn’t always know as much about her subjects but my research skills were impeccable. Whenever her roommate Abby would leave on a date Debi and I would talk about men and clothes. She agreed that Trent was a total cutie, and she would always offer to dress me up. I wouldn’t, afraid that Abby would return unexpectedly, but Debi would still find ways to help me by practicing her own makeup skills while I watched and asked questions. She would also insist that I wear the ‘proper’ underwear while visiting, helping me put on a bra to go with the panties I always wore now. Feeling that sweet tightness across my chest while Debi and I talked about the cuter guys on campus is one of my fondest memories. She would occasionally urge me to ‘come out’ and offered to introduce me to some other gay friends but I always refused. At heart, I was still just too much of a coward despite the thrills these conversations gave me.
My life became very busy as well now that classes were in full swing and I still had to keep my dorm room clean while doing mine and Trent’s laundry (I always thought of it as ‘our’ laundry) along with most of his homework with my own as well as being there for all Debi’s appearances as Lendy and visiting her as often as possible. Debi only came over to my dorm a couple of times but decided to stop when Trent started hitting on her. She said that while he was hot she would never steal a man away from one of her girlfriends. Debi always knew what to say to make me happy.
Wearing that mascot costume was hard work, particularly in the fall once football and soccer were in full swing. Neither sport had really slacked up very much when basketball was starting up so Debi and Lendy did not make every game, sometimes she had to prioritize, but she made a great effort at it. Several times she had to attend multiple sporting events on the same day and she would always come home exhausted. I was at every one that I could be at and gave her long massages afterwards to ease the cramps in her muscles. Obviously she was in great shape to maintain that sort of activity and I enjoyed rubbing the kinks from the muscles of her nude body.
I always wore a minimum of panties and bra when I did so and it was fun and easy to pretend that I was her girlfriend. If Abby wasn’t around I would sometimes use Debi’s dildo on her, she didn’t have much time for dating, and by now I knew just exactly how to tease her clitoris to ensure that she had a good orgasm. She would occasionally again offer the dildo to me for my own use but I continued to refuse. Not even when she offered to do me by hand would I agree to masturbate in front of her. I was both ashamed at my smallness and by the fact that I wasn’t a woman like her but she persisted until the weekend before thanksgiving when she caught me in a truly vulnerable moment.
Abby had gone home for the weekend, so I had allowed myself to be dressed completely for the first time since the semester began. I was in heaven as Debi and I sat together, giggling over boys and trying on various dresses and outfits. I should have realized that something was up when Debi pulled out a stack of brand-new magazines, bought just for me and that occasion I later found out, that were dominated by pictures of nude, handsome men. Two were recent issues of Playgirl and two others were Club magazine. The Playgirls were nice, the men were certainly hot, but their cocks were always soft. They stirred the imagination but didn’t really turn me on as much as the other mags did. The Clubs were primarily full of naked women but there was one blazing hot pictorial in each that featured a woman or women with a rock-hard stud busily working to fill their mouths and snatches. I was mesmerized by the pictures, just as Debi planned, and when she started making her offers I soon gave in.
Lying back on her bed she had me hold the magazine open to a particularly torrid picture showing a tight close up of an amazingly large and erect cock. To either side were the lips of two women, their tongues plastered to the sides of that beautiful dick, captured in mid-lick. Debi handed me her dildo, insisting that I kiss and lick it while imagining that at least one pair of those lips licking that magnificent cock were indeed mine. Lifting my skirt, Debi talked about how wonderful the guys said that I was at sucking cock, particularly Trent who had told Debi that I, Jill, was the best cocksucker he had ever known. All patently false but the fantasy worked like a charm and she barely had to squeeze my miniature cock through my panties twice before I erupted in the best orgasm I had ever had.
That night was amazing. Debi convinced me to hide in her closet when the dorm monitor checked the room and then I spent the night in bed with her dressed in her sexiest nightgown. I used the dildo on her twice, I even licked her clit although I really didn’t enjoy it, but she said that I could pretend that it was a little bitty cock. That didn’t really work but I didn’t mind doing it for her. She jacked me off twice more by morning and I was amazingly happy all the next day despite being exhausted. Debi added to my happiness by convincing me to wear a complete set of women’s underwear beneath my clothing; a girdle, slip and stockings to compliment my usual bra and panties. She explained that since I didn’t have classes on a Saturday and it was cold enough to wear a thick jacket that no one would ever know. They didn’t, but I did, and I was both frightened and exhilarated all day. I didn’t dare go back to my room dressed that way, but otherwise it was fantastic. When I did get back that evening after changing into a more modest pair of only panties beneath my jeans, even Trent commented that I seemed to be in a better mood than usual.
As the semester wound down the football and soccer seasons ended, we didn’t have a winning record and so no post season in either sport, leaving only basketball still going on. Trent and the men’s team were doing fairly well, they had at least won more than they had lost, but the women’s team was something like 0-12 going into conference play. Debi had gone to the football homecoming with a football stud named Darren and had continued to date him through December. I was more than a little jealous but then she gave me a picture of his cock at full staff and I forgave her. It was really nice and I certainly couldn’t deny her that kind of pleasure. I hid the picture well, but I couldn’t help taking it out when I was alone and pretending that it was Trent. Everyone was preparing to go home for Christmas break when the tragedy struck.
It was a typical college party; too much drinking and a bunch of people too young to handle it. Darren and Debi had double-dated with Abby and her latest boyfriend, she was a real slut it seemed, and Darren had drunk entirely too much alcohol. Abby called me from the hospital, babbling about Darren driving like a crazy man and hitting a tree. Debi was the only one who died.
The campus mourned, of course, but not like I did. I called home and told mom what had happened, she knew about my close friendship with Debi and likely believed that we were dating. I told her that I wouldn’t be coming home for Christmas; I really needed to stay here and sort out my feelings. She gave me no problems about it and I just lay sulking in my room for the first several days. When the dean of the college asked me to box up Debi’s things to send home, I couldn’t say no.
Abby had taken Debi’s death hard as well, and had not only gone home but withdrew from Lender College as well. They had roomed together for four years and done a lot of crazy things together. She had packed a few things but had left a lot of her stuff behind, and all of Debi’s remained where she had left it. Naturally I couldn’t very well send home everything; Debi’s dildo for instance, nor the magazines that she had really bought for me, so I was careful about what I packed. I was about halfway through and starting to look through Abby’s stuff when I found a letter from Debi’s parents. They asked that Abby send a few specific things home to them and then donate all the rest of Debi’s things to whatever charity she wished. They were too distraught to handle very much and wanted only a few cherished keepsakes. Unsure what to do I continued to pack up everything in the room, including the clothes that really belonged to me, and simply stacked them up in the closets. I mailed the things that Debi’s parents wanted but the rest I left in the boxes. I had no idea who to donate them to and wasn’t sure that I wanted to. The dean said that he understood the problem, or at least thought that he did, and that I shouldn’t be in any real hurry to get rid of the clothes. I had until the next fall to find a suitable charity to donate them to as the dorm room would remain open until then. The hardest part of the whole process was finding a present addressed to me on Debi’s top shelf. I very nearly lost it then.
I stopped wearing panties for a while. It was just too painful because all that I had had been given to me by Debi. I sulked around for days, spending all my time in Debi’s room, just lying on her bed and crying. When Trent came back after the holiday, he found me there. He sat beside me on the bed and even put his arm around my shoulders. I leaned into him and cried some more; not even turned on by his touch I was so miserable. After crying for what seemed hours, I realized that I had unconsciously wrapped my arms around his waist as I wept; but he hadn’t said anything. What a wonderful guy he could be at times.
When classes started up again I had developed a new routine; I now spent most of my free time in Debi’s dorm room. No one bothered me; the girls there simply looked on me with sympathy as I mourned. They didn’t knock on my door, they didn’t throw me out at night, I almost lived there. Once each day I would go back to my old room and do a quick clean up, washing mine and Trent’s laundry as always but I never stayed for long. Eventually I decided to unpack a few things at Debi’s, and put everything back where it belonged and also began wearing panties again; while folding them and putting them away the urge had simply became too much for me. I knew Debi would want me to have the clothes and Abby apparently didn’t want any of hers either. Finally, about the second week of January, I opened my present from Debi.
Breast forms. They were as realistic as could be with nipples and an adhesive to attach them to my chest. They were ‘B’ cup, the same as Debi. I cried again all night.
The next night I dressed completely for the first time since Debi’s death. It was sort of a celebration of Debi’s love for me. My new breast forms completed my look and I began to realize just how much I looked like a real woman when dressed. In honor of Debi I took out the magazines and her dildo and, with the help of a tube of lube she had, I slid it into my backside for the first time.
What can I say? Flashes of light burst in my brain after I got past the initial discomfort. Staring at that same cock picture and pretending it was Trent that was sliding in and out of my ‘pussy’ caused me to come as I never had before. I had been born with only one testicle and rarely did anything come out when I masturbated but that night must have been really special, because I left a large stain on the front of my blue silk panties. I lay there on Debi’s pink comforter and shook through two orgasms before taking the dildo back out for cleaning. I needed no more urging after that; I was hooked!
It was the very next day that my life changed again; at least it was for the better. The cheerleaders had gotten together and demanded that I be Debi’s replacement inside Lendy. Ms. Chlebowski wanted another female to wear it but all the cheerleaders were aware of how close me and Debi were, so they thought that it was fitting. Everyone knew that I had been the last person cut from the male side of the cheerleading tryouts, so I was obviously qualified. I was reluctant to accept, but the thought of a complete stranger wearing the costume was simply too much; and so I agreed.
The girl’s basketball team had a game in a few days, so I had to go to a couple of cheerleading practices and convince everyone that I had the routines down. No one was surprised that I did as they had all become accustomed to seeing me there watching Debi do them. One surprise I had was where I had to dress; in years past the person wearing Lendy had sometimes been a male and sometimes female, so there was a separate locker room just for whoever was wearing the costume. Debi hadn’t mentioned that. I was shown to the small room by one of the other cheerleaders and once I had shut the door found myself facing a large locker fronted by a wooden bench. Inside the locker was Lendy.
It was rough, I tell you. I shed yet a few more tears for my dear friend as I stared at the head of that fake puma. One of the custodians had cut the lock off for me so that I could get to the costume and when I finally managed to pull it out I was surprised to see what was hanging behind it.
It was Debi’s cheerleading uniform, given to her when she made the team as Lendy. She had never gotten to wear it but had kept it nonetheless. Perhaps she had worn it underneath the costume. Perhaps not. She had told me just how warm it could be in there. Hands shaking I removed it from the locker and hung it nearby. Further exploration of the locker allowed me to discover a small bag containing makeup and things for the shower. The locker room had a private one of those. A clean towel was discovered in a gym bag at the bottom along with a pair of white silk panties, a sports bra, a pair of white socks and some pink tennis shoes.
I put everything back except the costume but by the time that the next game rolled around, the thought of that cheerleading outfit simply would not leave my mind. Arriving well before game time I locked myself in my little closet and then stripped completely, utilizing the single shower to shave away the stubble of my body hair using Debi’s toiletries. I even used some of her perfume, figuring anyone that smelled it would think that it was simply clinging to Lendy from earlier uses. Afterwards I sat shivering on that cold wooden bench and stared at the outfit, wondering just how wonderful it would feel to wear it.
Debi had never brought it back to her dorm, so I had never gotten to try it on. I was certain that it would fit me; all of her clothing did, but wasn’t certain if I should or not. Finally I convinced myself that it would be ok to try it on, Debi wouldn’t mind, but there was no way that I could dare wear it out of the room; not even under the costume. Hurrying now so that I could try it on before having to change for the game, I slipped on the panties she had in her gym bag along with the bra. I had my breasts forms with me, a hint that my subconscious had already made the decision even if I didn’t realize it yet, and soon I was sliding that glorious garment onto my body. Grateful for the room’s mirror, I admired myself for a long time; my shaved legs looked fantastic beneath the short skirt and my breasts forms pushed out the top quite convincingly. With my hair back in my fantasy pony tail (it was short but doable) I looked and felt more feminine than ever before. My pleasure was almost orgasmic!
Telling myself that I would try on the costume over the outfit just to see how hot that it indeed was, I didn’t even hesitate once the head was in place but marched confidently out of the locker room towards the gym. No one would ever know what I was wearing beneath the costume and even if I took the head off during a break no one could see anything below my neck. It was perfect!
I sounded really brave but believe you me I was scared to death when I ran out with the other cheerleaders. I just knew that everyone in the stands knew what I was wearing beneath that fake puma fur. Somehow I managed to get through the game, I think we won but I’m not certain because of something that happened just before halftime that truly blew my mind. We were doing the ‘Lender’ cheer where the cheerleaders use their bodies to spell out the name of our college. The mascot was the last to run onto the floor and it was my job to be the ‘R’. It was while standing there being an ‘R’ that I happened to look towards the seat I had always sat in when cheering for Debi. Sitting in ‘my’ seat and smiling to melt a frigid heart was Trent.
What was he doing here? He had never been to a girl’s game before, I was certain. Not only was he sitting there he was waving at me! Flustered beyond belief I stumbled through the rest of the half and scampered to my dressing room as soon as the halftime show was done. This would be my only chance to take off the head and cool down; you weren’t allowed to take it off where any kids might see, even though there were no more than three hundred people in the stands and probably not more than a dozen kids in the whole gym. Just as I reached the hallway before my dressing room and reached up to pull the head off, I heard someone calling my name.
“Josh, wait up,” said Trent, trotting up behind me. “I’ve been yelling your name,” he said as he caught up, smiling at me in that way that I loved.
“Sorry, I guess I couldn’t hear you through the head,” I gushed, trying to understand why my beautiful roommate had followed me down here, or even came to the game for that matter. My heart was pounding as I looked up into his baby-blues. To him I might be a scrawny boy in a fur costume but at that moment I was imagining myself as a girl dressed in my cheerleading outfit. For me, that fur costume had ceased to exist. I was patently aware of every stitch of female clothing I was wearing and consciously pushed out my pert B cups as far as possible, wishing that they were real and that he would see me as I wanted to be.
“Yeah, I don’t hear too good when I’m getting head either,” he laughed. A typical Trent joke.
Trying to be witty and return his with a cute remark of my own I blurted, “I didn’t say when I’m getting head, I said I couldn’t hear when I was giving you head…”
I was shocked into silence for only a moment before trying to fix my error. Talk about your Freudian slips! “I meant when I was wearing the head… the costume head I mean,” I stammered, knowing that my face was brilliantly crimson.
Trent smiled all the more. “You’re not too good at those comebacks,” he laughed.
I smiled, grateful that he hadn’t teased me more than he had. “What brings you down here? I didn’t think you liked watching the girl’s games?” I asked after a short and uncomfortable silence. Uncomfortable for me, anyway.
“I don’t. Tall girls do nothing for me. I like ‘em short, about your height is perfect.”
Still blushing I filed that bit of information away for future fantasies. “I suppose you like them big breasted too? EE’s or bigger, right?”
Again that laugh. The sight of his lips were making me weak in the knees. How I would adore kissing them!
“Nah, not me,” Trent chuckled. “I like breasts, don’t get me wrong, but those big floppy ones? Nah. C cup is good, but give me a good old B cup anytime and I’m just fine.”
My heart almost leapt from my bra at that comment. If he only knew what he was doing to me! If he said one more thing like that I just knew I was going to cum in Debi’s panties.
“Actually I just came to see you, I mean watch you. Gotta support my roomie after all,” Trent said, blushing slightly for the first time since I’d met him. He suddenly leaned closer and sniffed. “You really smell nice.”
“Well…” I began, flabbergasted by his statement. “Thank you for that, Trent. I don’t know what to say.” I hoped I wasn’t going to cry again. Had I thanked him for coming to watch me or because he said that I smelled nice? I was so confused; thinking straight seemed to be impossible since I had mentioned giving him head.
“No problem, glad to be here, I’m really enjoying the show... well, guess I better get back out to my seat. Break a leg and do a cheer for me when you get back out there,” he said, turning away. I really didn’t want him to go. I wanted to drop that costume there on the hallway floor and shout ‘See? I’m a woman! Your woman, Trent’! Of course I didn’t. I watched him for a moment, his butt looks nice in jeans, and then turned with a sigh back to my locker room.
“Uh, Josh?” he asked, turning and coming back towards me. I gladly waited for him; every second spent talking to him while wearing what I was wearing was pure bliss for me.
“Yes Trent?” I asked, my voice as soft and feminine as possible. I knew he wouldn’t notice; my voice is not exactly masculine at the best of times.
“I just figured that I should tell you that… well the costume is kind of torn… I mean, there’s a rip in it, right here in the back,” he said, turning me and moving quickly before I could stop him.
My heart had stopped in fear. How bad was it? What had he seen? Before I could turn away or run for the safety of my dressing room he was behind me, lifting the puma’s tail in reaching in to place his hand directly on my butt cheek. His hand was beneath my skirt but the bottoms of my outfit barely covered my panties. He was touching me directly on the skin of my ass.
“It happened when you did the splits, there about halfway through the half? I believe I was the only one that noticed, you can’t see anything except when you do a handstand or cartwheel or whatever,” he said, slowing withdrawing his hand from my backside. “But maybe you shouldn’t do any more of those, if you don’t want anyone to see what you’re wearing,” he finished.
My heart had stopped again. I was torn between fear at being found out and desire for him to put his hand back where it had been. I stumbled out a thank you and nearly dived back into my dressing room.
I was mortified with having been found out, and by my roommate no less! My life was truly over, at least at this college. Even as I sobbed my heart out I was shedding my feminine clothing and wondering if my scholarship would transfer to another university. By the time I came back out for the second half it was nearly half-way over, one of the alternate cheerleaders had to be sent to get me and Ms. Chlebowski was furious with me. I mumbled something about having lost track of the time and she eventually forgave me. I was doing a better job than anyone else she could have gotten midway through the year since I knew all the routines already, so she really didn’t have any choice. I finally stumbled back onto the court wearing my boring old sweat suit; I had even removed my panties, beneath Lendy’s furry exterior.
Despite my change of clothing I was still wary about doing cartwheels in the costume. I wasn’t certain what all had been revealed but at the very least the hem of my cheerleading skirt had to been visible for Trent to have recognized it. I’m glad no one could see my face because the mixed embarrassment and fright must have been a horrible thing to see. Who else had noticed? Who else would be waiting to make fun of me after the game or tomorrow? Trent wouldn’t be in the stands anymore, I knew that, he’d be back at our room packing or tossing my things out the window. I didn’t blame him; seeing his roommate wearing women’s clothing must have been a terrible shock. Seeing him sitting there in my old seat was almost more than I could believe.
I’d never been so nervous and I can’t believe that it didn’t show. Everyone said that I did a great job in the second half but I don’t see how. Trent sat and smiled at me, applauding my every move without paying any real attention to the basketball game and my knees knocked in fear and excitement. Only once did he show anything but support for me, and that was just after my first flip of the half. I came up in the victorious, arms high position they teach you in gymnastics to find him frowning. Something had upset him, but what? Immediately after his smile returned as he applauded me and I soon pushed any thoughts of the frown away; apparently he wasn’t mad at me. That made me feel a little better; perhaps his moving out wouldn’t be quite so dramatic after all. By the end of the game I had resolved to be the one to move out just as soon as he brought the subject up; I could stay in Debi’s room after all; no one seemed to mind.
The game finally ended and I fled to the locker room. My intentions were to change as quickly as possible and hurry back to the dorm before anyone who had noticed what I was wearing in the first half could accost me. I even considered leaving in the costume just to save time but knew that Ms. Chlebowski wouldn’t like that. Maybe I could find a side door no one knew about, and so avoid the heckling crowds. An easy escape was not to be, however, as standing right in front of my dressing room door waiting for me was Trent.
My shoulders sagged at the coming confrontation. He was being polite about the issue, staying for the rest of the game was evidence of that, but there was no way I could avoid discussing what he had seen with him. Could I convince him to keep my secret as Debi had done? I doubted it. I just hoped he didn’t get really mad and beat me up.
“Hi Trent,” I mumbled, pulling the puma head off and clutching it to my side. “I hope you enjoyed the game.” My ‘hope’ sounded pretty weak and depressed. I just wanted the bad part of this conversation behind us. He smiled, even when depressed that sent a surge of pleasure through my body. He was so pretty!
“I didn’t really watch much of the game, I was just here to see you,” he said, placing a hand on my shoulder.
“Oh, well thanks,” I murmured, unsure how to progress from here. Surely he just wanted to tell me to get out of our room but he sure was beating around the bush about it. I decided not to be the one to bring up the subject. “I guess I did ok, I was pretty nervous.”
“You did a fantastic job! As good as Debi could have,” he bragged, bringing another blush to my face. There wasn’t anything he could have said about my Lendy skills that would have made me feel better than that. But, he wasn’t done speaking. “Of course, I thought you did a better job in the first half than you did the second.”
Here it came; somehow he was going to swing the conversation back around to what I had been wearing. Suddenly I decided that we needed to get out of the hallway for this conversation; being alone in my locker room with him might get me beat up but at least there was less chance for someone to overhear. Ducking around him I motioned for him to follow me into the room as I responded.
“I guess I was a little tired by the second half,” I said, thinking to myself that ‘tired’ should have been replaced with ‘mortified’.
“Tired? Nah, I don’t think it was that. You just seemed more… comfortable, in the first half,” he said as if thinking hard about it. “You’re movements were more confident; freer, in some way.”
We were halfway through the door now when I realized my mistake. My cheerleading outfit was scattered all over the place; I hadn’t even bothered to hang it up when I had changed. I had been in too big a hurry. Everything I had been wearing was immediately visible to Trent, and it was too late to distract him from following me into the room. Now he would know that I had not only been wearing a cheerleading outfit, but all the feminine underwear that went with it. Even my breast forms were visible! I could have died, and even wished that I could at that moment.
He said nothing, just stepping around me where I stood stiff-backed and closed the door behind him. I could see that he was looking at the panties I had been wearing; they were laying inside-out across the end of the bench. Next he stepped over to the locker itself and picked up one of my breast forms from the top shelf. Cupping it in his hand for a moment he smiled and said: “B cup, I believe.”
That was all I could take, I collapsed onto the bench and began to sob. As much as I had cried since Debi died I wouldn’t have thought that any more tears were possible but they flowed freely anyway. Surprise couldn’t begin to express my feelings when Trent sat down beside me and put his arm around my shoulders.
“Shh, Josh ease up man,” he said, hugging me to him with one arm. I wasn’t sure how to react so I simply sat very still, the tears flowing but the feeling of his arm around me too wonderful to ignore. I tried to think of some excuse for what I had been wearing; a lost bet, a hazing ritual for a fraternity, but nothing that I sputtered made sense. Trent wasn’t listening to my babbling anyway.
“Look Josh, you like wearing women’s clothing, that’s ok,” he said, shushing me. “If it makes you happy, then I’m ok with it. I’m sorry if my finding out hurt you but you have to believe me when I say that your secret is safe with me.”
I tried to choke back my sobs but it was difficult. Of course my secret was safe with him. Now that I thought about it; he couldn’t tell anyone for fear of looking gay himself after having lived with me for all those months. His soft voice eased my tension some, and the stiffness left my body allowing him to pull me a little closer by my shoulders. I couldn’t think of anything to say so I just sat silently, miserable and yet elated at the feel of him sitting so close, even through a puma costume his body heat was palpable.
“It’s not like I didn’t suspect; a lot of people around campus think that you’re gay, but I didn’t realize that you wanted to dress up in women’s clothing. I think that’s great; you should do it if that’s what you feel,” he said, squeezing me closer again. He may have been doing that to show support but he was seriously turning me on!
“Just because I wore women’s clothing, it doesn’t mean that I’m gay!” I managed, looking towards him but not able to lift my gaze above his chin. I was afraid that he would see the lie in my eyes immediately.
“I understand that,” Trent said, reaching down and cupping my chin gently. Lifting it up, he forced our gazes to meet before he continued. “But you are gay, aren’t you Josh?”
The tears were welling up again and I tried to choke out an argument but all that came from my mouth was a sob and four whispered words.
“My name is Jill.”
I cried really hard then. He took me in both his arms and held me close, making those small ‘shh-ing’ sounds that people do to calm someone who is crying. I put my arms around his waist and buried my face in his chest. I was miserable but loving it too. I even cried a little longer than necessary just so he wouldn’t let go. Finally my sobs eased and he pulled away. Reluctantly I let him go before turning to the locker to find a cleanex. It was a good thing that I wasn’t wearing makeup; it would have run all down my face.
Woodenly I began to strip off Lendy, my gray sweat suit plastered with moisture and a distinct odor of sweaty body rising up from me. I stripped the top off but stopped before removing the bottoms; I didn’t want Trent seeing me naked or even nearly so. I needed to take a shower badly but couldn’t so long as he was here. I sat with my back to him, suddenly noticing the two red splotches on my chest where I had removed the breast forms too quickly, looking only at my feet. He stood behind the bench watching me, expecting me to say something, I suppose, but I had nothing to say. My life was over; despite his claims I knew that the whole campus would soon know everything about me. At that moment I really wished that I could die; perhaps Debi and I could be together again.
“I never really noticed how attractive you are,” Trent said, his voice soft yet causing me to jump when he spoke. “I bet you’re beautiful when you’re all dressed up.”
I said nothing; my heart was pounding too loud and would have drowned me out anyway. I wanted him to say that again but he didn’t; he moved on to something even more wonderful.
“As a matter of fact, I bet you look really nice in your cheerleading outfit. I’d really like to see you in it, without the Lendy suit over the top,” he chuckled.
Somehow I managed to turn my head enough to see him. I wanted to see the derision on his face; the proof that what he had just said was nothing more than a cruel joke. I saw nothing like that; only sincerity and his to-die-for smile.
My words were almost a whisper. “I… can’t wear it home… someone would see…”
“No problem,” he said excitedly. “Just bring it home with you and you can model it for me... Jill.”
The woman inside of me leapt for joy at Trent saying my feminine name. The tears in my eyes turned instantly from sorrow to happiness and it was all that I could do not to jump up from that bench and into his arms. At first I had no idea how to respond but finally something came to mind.
“If you want me to, I will Trent,” I managed. “But I’ll need some time before you get there… I don’t want you to see me change.”
Trent’s smile went from hot to panty-melting luscious. “No problem, I’ll go grab a burger and see you at our place in, what? An hour?”
I nodded happily as my mind replayed his words; ‘Our Place’.
He left, suddenly seeming as awkward as I ever was around someone I wanted to date. Our goodbyes were perfunctory but I barely noticed, waiting for him to close the door so I could jump into the shower.
I showered quickly, re-shaving my body despite having done it only a couple of hours before. I needed to look my best after all. Once I was clean and at least partially toweled dry I hastily put on a pair of panties, and to my surprise, a clean bra for the walk home. I rarely wore a bra outside but somehow this situation demanded it. There was still a chance that Trent was setting me up somehow, perhaps bringing some of his jock friends over to embarrass me once I was dressed, but at that moment, for the first time in my life, I just didn’t care. If there was even the slightest chance that I could become Trent’s girl then I was going to go for it. Once my drab male outer clothes were in place I hastily repacked all my girly things and with the cheerleading outfit safely stowed in my gym bag, rushed out of the building.
Almost running I hurried home, stopping by Debi’s place for a few things I would need along the way. I reached our room with only thirty minutes to prepare and flew through my routine. I know it was silly but I put on a pair of sheer pantyhose along with a matching white panty-bra set that was very lacey and almost brand new. The cheerleading outfit slid on as dreamily as before and the little bottoms fit as snugly as they could have on Debi. A pair of ankle socks with fuzzy little pink balls and Debi’s pink shoes completed my outfit, giving me only fifteen minutes to fix my hair and put on my makeup. I made it but only barely; Trent arrived exactly on time; not a second late!
It surprised me that he knocked; he lived there too, after all, but I was glad that he did as it gave me a moment to calm myself. My hair was back in its ponytail, I really didn’t know what else to do with it, and at least according to the mirror I looked as good as any real cheerleader could have. Practicing my girlish walk, just as Debi had taught me, I minced my way to the door as I struggled to breathe through my anxiety. Thankfully the door had a peephole, so being able to see that Trent was alone helped calm me somewhat. Finally throwing caution to the wind I threw the door back and gave him his first look at Jill.
Was he surprised at how good I looked? He says that he wasn’t but I could tell that he was flabbergasted. He had brought me flowers (where had he found them this late?) and never failed to call me Jill after he entered the room. We talked for an hour, me sitting demurely on the edge of a chair while he sat half-reclining on his bed. Eventually he convinced me to put on a cheerleading exhibition for him and watched excitedly as I kicked my legs and tumbled about the room. I could tell that he really liked my legs and when I did a hand-stand he held his breath the whole time my skirt was up; the crotch of my tiny cheerleader shorts completely exposed to his gaze. Finally, out of breath, I allowed him to grab my hand and pull me down to sit next to him on the bed. I looked at him, smiling with the joy of showing off for him and found his lips closing in on mine.
We kissed.
It wasn’t a mouth-open tongue-wrestling match, it was just a kiss even if the world did stop rotating. Our mouths were slightly open, I know I didn’t breathe the whole time, and we probably only held it for about ten seconds but I was immediately in love with that sweet man. When we broke away we didn’t look at one another for a minute or so; just sat looking away and thinking about that kiss. My whole body was tingling; from my toes upward, at the thought of what had just happened. My mind was spinning; perhaps from a lack of oxygen but the kiss had contributed as well. I wasn’t sure if he was sorry we had kissed, but if he wasn’t going to say anything to ruin the moment I certainly wasn’t. Finally I felt him turn towards me so I looked his way as well; even if he was going to tell me that kissing me was a complete mistake I wanted to watch his sweet lips as he said it. He had kissed me!
Whatever he had been planning on saying was never spoken; we silently drifted back together for another soft kiss. Another followed that one and soon enough we were going at it hot and heavy; our tongues licking one another as our lips moved softly together. We didn’t break our lip-lock for what seemed like only a few minutes but could have been hours. When I came back to myself Trent was lying back on his bed and I was laying half-way on top of him. His arms were wrapped tightly around me and my hands were wandering across his muscular chest. We stopped for a moment to catch our breaths and I took the opportunity to rest my head on him as well; it felt as wonderful as I had ever imagined to be lying there in his arms. Soon though I knew it would go further; there was no way I was going to let this end here.
Trent excused himself to go to the bathroom and I freshened up a little as well. When he returned I met him at the door and after making sure the hallway was clear, gave him a long, lingering kiss. His hands slid up my skirt and found only panties between his skin and my rear. I think he liked that; he certainly gave my ass plenty of attention. Once the door was closed I took his hand and led him back to his bed, mine didn’t even exist at that point; I had wanted to be in his with him for so long. I helped him undress as we went; getting those tight jeans off was a chore but I loved ever second of it. Finally came the moment I was waiting for; the removal of his underwear. Trent wore briefs most of the time, and tonight was no exception. I dropped to my knees when his ‘tighty-whities’ were all that he had on and smiled shyly up at him as I grabbed onto the waistband.
He smiled back, and I excitedly began to slowly strip him of his shorts. I was desperate to see his cock but didn’t want this wonderful moment to end too quickly. Slowly, so slowly, I pulled down on the elastic, watching for the first sign of his manhood to appear. I had no preconceptions of how large or small he would be; I knew that he had to be bigger than me, and I really had no idea what it would look like, my only experience with a ‘live’ cock was with my own, and that had never caused the sort of bulge I had seen in Trent’s shorts. I kept expecting to see the head of his cock first, surely that bulge meant that he was already erect, but as the underwear descended I continued to be frustrated. Where was it?
Suddenly it was there, but not the engorged cock head I had been expecting but the thick base of a truly man-sized dick emerged from the crop of kinky pubic hair. I couldn’t believe how thick it was, or that it was apparently still not hard despite the bulge, and began to pull his shorts down even more slowly as my hungry eyes devoured each emerging inch. How big could it be? I couldn’t begin to guess but my mouth was already watering over what I had seen so far.
Inch after glorious inch was revealed as I pulled the shorts down. It was partially erect but protruded at least two inches straight out from his body before it sagged downward beneath its own weight. He gave a sigh of relief as it was freed; I guess it was pretty uncomfortable all bent up like that. Finally, just as I decided that it might drag the floor before I freed it, a complete exaggeration of course, the head of his cock slid free of the restraining elastic, and I could finally behold the beauty that was his dick.
Did I mention that it was big? It was, wondrously so. I don’t know how long exactly but it was certainly bigger than anything I had ever seen on the internet. The head itself was thick and looked to be longer than my thumb. It was the most beautiful thing I had ever seen, at least until it was completely hard. I realized that I was holding my breath and let it out quickly; it was so beautiful it was breathtaking anyway; no sense in passing out now before I had even gotten to touch it!
Hands shaking, I reached out to grip Trent’s massive member, smiling at his groan of approval as the thick base was gently gripped in my palm. I still couldn’t take my eyes off it; it was so perfect with its thick ropey veins and fantastic proportions. It immediately began to twitch once I had it, and to my amazed sight began to thicken and grow. The head started lifting with each twitch, rising from its downward-pointing position until it was almost sticking straight out in front of him… and right directly at me. Tentatively I leaned forward and licked it right on the very tip, reveling in the salty taste of his cock. It was delicious! Opening my lips I kissed it next, sneaking in a second lick as I did so and then grabbed it with my other hand as well so that I could better admire the lipstick I had left there.
“Oh, yeah, Jill,” Trent groaned, his thick cock now jutting proudly out before him. I couldn’t see how it could get any bigger but it was obviously still getting harder and I adjusted my grip to compensate. Trembling with pleasure I opened my mouth even wider and slid his glorious manhood inside, carefully pulling my teeth back just as Debi had taught me and allowing it to nestle on my tongue. Nursing gently on it for a moment with just the head inside gave me a good taste of his precum as his mammoth dick hardened even further inside my mouth. I absolutely adored the flavor. I pulled back only for a moment, his groan of disappointment was too sexy to ignore, and finally got to see him fully erect; and believe you me it was magnificent. I slid him back where he belonged and slid it in and out of my mouth for a while; so happy I could have died.
Rising to my feet I kept his cock firmly in my hand and gently led him to his bed, turning him and pushing him so that he lay on his back before me. He was all mine; his cock jutting firmly upwards with its need; a need that only I could fulfill. Sighing in pleasure I knelt beside his bed and with his cock still gripped in one hand, lowered my face upon it.
It was wonderful! I kissed, licked and gnawed at his beautiful beast, trying to taste every glorious inch. I couldn’t deep throat him, unfortunately, but I did the best that I could. I quickly found the spots he liked me to lick the best and all too soon I sensed that he was nearing the point of no return. I wanted it to last longer, honestly I did, but I just couldn’t wait to taste his cum so I left off sucking his balls and positioned myself so that my hungry mouth was right above him and then I slid his wonderful cock back into my mouth and began bobbing up and down; all the while stroking his meat with both hands as I urged him to cum in my mouth. With a grunt and an ‘Oh, Jill!’ he did just that; arching his back as his sperm erupted into my waiting mouth.
All that I can say as that it was even better than I had ever imagined. Had he cum a gallon, I would have wanted to taste every drop. As it was I ended up wearing a lot of it, but enough made it onto my tongue that I was satisfied for the time being. I sucked on it long after his orgasm was complete, and he rewarded me by never going even a little bit soft.
“Can I fuck you, Jill?” he eventually asked once his breathing had eased. I said nothing, just used my favorite handle, his cock, and urged him out of the bed so that I could take his place. My ‘pussy’ was already well lubricated so I lay on my back with my legs spread wide; I couldn’t wait to feel however much of his cock I could take inside me. He didn’t make me wait but immediately crawled on top of me after flipping my skirt up. Once his body weight was in place, that was really nice all by itself, I felt him tugging my panties to one side and then, glory of glories, his cock head pushing up against my opening. I shivered in a mixed state of bliss; combining fear, anticipation, and a life of desire into one overwhelming emotion. Trent moved his mouth to my neck where he bit lightly at me as my attention remained only on that part of his body that was entering mine. Then, after giving me a moment to gather myself, he began to thrust his hips forward.
Yes it hurt; it felt amazingly wonderful as well. I couldn’t take all of himl but I did pretty well for a virgin. Trent was inside me, his big cock pounding my little pussy as he drove me to orgasm after orgasm. Debi had tried to tell me how good it felt to have a man inside you but she just couldn’t do justice to the act itself. My mind ran away on the waves of repeated orgasms, reveling in the feeling of him sliding in and out of me. Later I heard some of our neighbors congratulating Trent on the fucking he gave that ‘slut’ that night, so I know that I wasn’t too quiet. I didn’t care; all I cared about was the pleasure I was getting from my man. Ten minutes or six hours later, I couldn’t be sure; I felt the warm spray of his sperm inside me. We clung together for a while, whispering little endearments until we fell asleep in one another’s arms.
We tried to keep our relationship a secret and we were successful there; however my crossdressing quickly became the best-kept secret that everyone at Lender College knew about. One of the cheerleaders had also noticed what I was wearing underneath Lendy that first game but didn’t say anything for a few weeks. She apparently had a brother who crossdressed and so was sympathetic. Eventually she did tell her best friend and the two of them decided to speak with me about it. Before long the entire cheerleading squad knew about me and ultimately I was allowed to practice with them in Debi’s cheerleading outfit without Lendy. This led to my forsaking my men’s clothing completely; everyone knew about me already and wearing skirts to class was thrilling. Before I began living as a woman I would never have dreamed that revealing my feminine side could have filled me with such confidence but it most certainly did. Being caught wearing panties and a bra was once my greatest fear but now being seen in public as a woman is something I look forward to.
When one of the girls from the squad twisted an ankle, I was allowed to fill in as an alternate on the cheer squad. That only allowed me to sit on the sidelines and shake my pompoms but it was still a wonderful experience. There were a few nasty things said to me here and there but with Trent’s love and the support of my new friends I overcame them; being a woman full-time was simply too fantastic to worry about that sort of stuff.
Naturally my relationship with Trent became more difficult when my secret got out. He didn’t want to be thought of as gay and maintained that I was all woman to him. I was thrilled with that thought and so I offered to move out of our room and into Debi’s to help preserve his reputation. That was what I did but I still spent most nights with Trent; I still cleaned his room and I did all of our laundry together. I also took care of his more basic needs; that man’s sex drive is insatiable! I am so thankful for that. No one said a word to me about staying in Debi’s room, I didn’t think that they would, and the other girls of the dorm welcomed me as their new sister. I was even offered to pledge with a sorority for my sophomore year!
The next year flew by and so many wonderful things happened to me. Trent and I are still together and as my transformation to living as a woman full-time began we decided that we should move away from Lender College. When that year ended I was beginning hormone treatments, how I desperately wanted my own breasts, and Trent accepted a scholarship at a larger university. I was able to transfer to the same school myself; apparently the grades I make are universally accepted. By the time the new school year began my name was officially Jill and so far as I knew no one at the new university had any idea that I was once Josh. That took some creative paperwork but I managed it. My computer skills are topnotch. We live in a small apartment just off campus and some of our new friends think that we’re married… I love that thought. I wished now that I had legally changed my last name when I became Jill.
I eventually told my mom about Trent, and she wasn’t as supportive as I had hoped but we’ll work through it. I walked on to the cheerleading squad at the new university and made the team… as an alternate (argh!). Still, I get to practice with them and despite my love for Trent do enjoy having my little body tossed around by those big strong men. Sitting upon their hands while they lift me up in the air is pretty nice too; nothing like a good grope to make a girl feel special, lol!
My breasts finally began to come in by the time my junior year began; I was getting so tired of wearing those breast forms. My doctor says that I seem to be destined for ‘big B’ or borderline C cup. That’s more than enough for me, and for my Trent. He loves my breasts and spends a lot of time kissing and sucking them. What that man can do with a nipple… wow.
I think this is going to be our year. After starring at Lender as a freshman, Trent didn’t have to sit out a year but still didn’t play a lot as a sophomore. Now, as a junior, he is starting and is one of his team’s better players. I think I can make the cheerleading squad for real this year; not just as an alternate sitting around waiting for an injury, and if not the dance squad is trying hard to recruit me! I’ve been to meet Trent’s family lots of times; they have all accepted me as a female and I’m not sure if or when we’re going to tell them the truth. Lately I’ve been considering surgery to finish the deal and if that happens, maybe I won’t have to. It would be nice to have my very own vagina but I’m not sure that I have enough ‘equipment’ for the doctors to work with down there.
Thank you for listening to my story. I am happier now than I have ever been but am more than a little sad that it all came about because of the tragedy of another. I wish Debi could be with me and share in my joy but I will always love her for what she gave me; a whole new life.
Jimmy desperately wanted to join the same fraternity as super-hot stud Mike and was willing to suffer through a lot of hazing; little did he know just how far some of the frat brothers would go to drive him away but somehow he held on until the last night... and then things went terribly wrong.
"You give us away you little bastard and I'll cut your balls off!" Dave threatened.
Lying as still as possible I stare up into the dark, thankful that the others couldn't see the look on my face. I was much smaller than both men and had been forced to defend my heterosexuality all of my young life. Now that I was in college and pledging for a fraternity it was even more important that I maintain my masculinity but, unfortunately, the current situation we found ourselves in was threatening my secret.
College wasn't as hard as high school, where everyone knew everyone else and remembered every stupid thing you had done in your whole life. Back home I had been beaten up as a faggot more than once but by my teens the bullies had found other people to pick on and I worked hard to be invisible. Not too difficult considering my small size. No girls ever accepted my date requests and I had been forced to take the biggest, ugliest girl in school to the senior prom. Through all those years I had maintained that I was not gay, and I truly believed that I was not, until I met Mike Stephens.
No one who saw Mike would say that he was anything but gorgeous. Tall, strong, and a body he had worked hard to perfect, he was the best looking person of either sex I had ever seen. We met when I went to a summer orientation a month before my freshmen year in college was to begin; he was a soon-to-be junior and one of the guides. I immediately became flustered at the sight of him and had trouble looking him in the eye throughout my tour. I dreamed about him that night and by morning was masturbating to fantasies of seeing him naked. So much for my dreams of not being gay. I joined Mike's fraternity as soon as I was able and Mike had to vouch for me just to get me in the door. I dreaded the coming hazing but resolutely vowed to survive it just to live in the same house with Mike. I had already heard that they used a community shower and I couldn't wait to see him naked.
And the hazing was just as bad as you can imagine; probably worse than most people would have expected. Because of my tiny size I seemed to be the favorite whipping boy of all the upper classmen and had to embarrass and debase myself in many different ways. But it wasn't all bad; some of the things I had to do were almost wonderful.
Right off the bat they ordered me and some of the other smaller pledges to wear panties and bras at all times, subject to be shown to anyone who asked to see them. Word got out quickly around campus and I had to show my underwear off several times each day. One by one the other pledges were allowed to stop wearing them, but even after two weeks of hazing I still had to wear mine; but that was one of the wonderful parts; I loved every minute of it.
I had secretly crossdressed at home for years even while valiantly defending my heterosexuality to myself. Having a perfectly acceptable excuse to wear feminine underwear in public was like heaven and I had to pretend to be embarrassed when some stranger I didn't even know demanded that I show him or her my panties in class or out on the quad. Everyone knew that I was being forced to wear them so my nightmare of being caught was at least temporarily suspended, and when the other pledges one by one were released from that torment after successfully completing some ridiculous task, I just didn't bring it up, telling the one or two who asked that I'd rather wear the panties than have to swallow live goldfish or dance atop the Dean's house naked during lunch. Surprisingly no one thought this all that strange, and so the sight of me with the lines of a bra showing beneath my t-shirt was not even questioned. Now, with Mike's naked body pressing against mine in the darkness of the closet, I wasn't concerned about him feeling the outlines of my bra or the smoothness of my panties beneath the women's top and short black skirt he himself had ordered me to wear. What I did dread was if he happened to discover the raging hard-on I was sporting... not that it was very big, easily unnoticed in most any other situation, but with him lying directly on me and so little material between us, I had to figure he would notice it poking into his stomach.
And there was literally nothing I could do about it. Thinking about baseball or whatever was useless when I could feel his weight on top of me and feel the hairs of his balls tickling my chin. His cock, the object of so many of my fantasies, was hard and right there, so close to my mouth I couldn't help but drool. If he scooted back just a few inches I would be able to taste him, so there was no way I was going to convince my cock to go limp now; I wanted to remember every moment of this before it was over!
So now the real question is, how did we get in this situation? Pretty simple, really; I was ordered by Mike and Dave, both of which were fraternity officers, to accompany them on a visit to their girlfriends Melinda and Robin; the daughters of the Dean. Both were very attractive but also kind of slutty and Robin was only seventeen; jail bait in our state. In a last attempt at driving me from the fraternity Dave had come up with the ultimate embarrassment, or so Mike had warned me privately, and as the end of the three-week hazing period would soon be over all I had to do was get through this one last
evening and I was a shoe-in to join the fraternity. Certain that nothing Dave could think of was worse than some of the things they had already done to me and some of the others, I was satisfied that I could survive one more evening.
Mike came to my room in mid afternoon, bringing me the pink top, skirt, and pantyhose it had been decided that I must wear. Pretending to reluctantly change I went with the others to the Dean's home, finding out once there that the Dean and his wife were out for the evening and the girls had the house to themselves. Figuring that he had thought of something I would have to refuse, Dave really didn't like me, my task of the evening was to hold each man's dick and insert it into his girlfriend's pussy. I guess it was something Dave thought of as the ultimate shameful act.
"You've never even seen a pussy, so this is your chance to see two and see what a man does with them," he had joked, shoving me around as he explained my duties. I acted very upset but couldn't wait to see, and hold, Mike's cock in my hand. No matter what he did with it afterward, two of my most cherished fantasies were about to come true.
After all four of them were naked, Dave and the girls looked good but Mike was amazing, I carefully took Mike's dick in my hand and worked it up and down Melinda's juicy slit, wishing that it was me who had the pussy that was about to be invaded by Mike's big, thick cock. His dick was as beautiful as he was, in an angry, veined sort of way. I took as long as I possibly could working the thick head inside her without seeming to and was thrilled when Dave ordered me to let go and do him first.
"I'm the president of the fraternity, and no one told you to do Mike first," he had sneered. I didn't complain, ecstatic that I would get to hold Mike again, and worked Dave's respectable cock into Robin's tight teen pussy before returning to take care of 'my' man Mike. Gripping him only slightly tighter than was truly necessary, I again took my time working the head of his meat into Melinda's snatch, letting go only when Mike slid himself deep inside for that first long stroke.
Grumbling something at me, Dave looked mad that I hadn't refused to follow my orders but didn't respond when I asked him to repeat it as he was already pounding away on Robin. Pausing with his cock buried in Melinda, Mike translated for me.
"Dave said for you to go downstairs and watch out in case their parents come home," he said, turning his attention away from me and back to the luckiest girl in the whole wide world. Imagine; being fucked by Mike Stephens! I couldn't think of anything I would enjoy more and she was lying there in that frilly twin bed taking it for granted.
Before I left the room I paused to admire Mike's powerful ass as he pile-drived the whimpering girl beneath him. Leaving the door slightly ajar I finally tore myself away from the sight and minced downstairs, trying not to cry at the unfairness of it all. I wanted Mike so bad and to be so close to him and not have the opportunity to kiss him, suck him, taste him, was devastating.
Dejectedly I walked down the stairs, trying to lose my unhappiness in the joy of watching my nylon-clad legs lifting the hem of my skirt as I walked. Not even the sight of my A-cup tits, falsies added to my daily costume as ordered by Dave only a week ago, thrusting out the girlish pink top did anything to ease my gloom. Flouncing into the Dean's huge living room I petulantly flopped onto his couch and sulked there in the darkness, tormented by the sounds of the lovemaking I could plainly hear from upstairs but couldn't join in on. Would I die a virgin? Would Mike ever notice me? Not that I wanted him to; I didn't want to be known as a queer. Was that bitch Melinda cumming again? While fucking my man? I was so mad I almost didn't react when the headlights shone over the front windows.
As such things generally work out; it was the girl's parents coming home early. I ran upstairs to warn the others and was the first to follow Robin's command of 'hide in the closet'. We all knew we were risking expulsion from the university and more; Robin was underage and Dave at least was looking at possible jail time if we were caught. That's how I came to have Mike's naked body pressing down atop mine; it was almost worth getting caught just to have him there, but I really couldn't face him if he noticed my erection. I lay as still as possible; not wanting to make any noise but also hoping that Mike would mirror me and stay exactly where he was, for hours if possible, and be so intent on watching for trouble beneath the closet door that he wouldn't notice my little panty-covered dick throbbing beneath him. I was so excited that I thought that I might could cum right there, just from feeling Mike's weight pressing down on me.
We lay there for a few minutes, everyone trying to control their breathing, as I wished for just a little more light so that I could see Mike's body more clearly. What little light we had was blocked from my sight by Mike's ass, so we lay quietly listening to Melinda and Robin speaking with their parents. Melinda was downstairs, talking with the Dean while Robin and her mother were standing just outside the girl's room, speaking of why they had cancelled their dinner plans. These conversations went on for a seemingly long time, when Dave shifted his weight and a high-heeled shoe by his foot fell over with a soft 'thunk'.
"Did you hear that?" demanded the Dean's wife, suddenly charging into the girl's room. "I heard a sound from the closet," she stated, stalking directly towards us. Involuntarily Mike shifted his weight back, pushing away from the door and discovery before he realized there was no where to go or hide before he froze again into immobility. I very nearly came right then and there because his inadvertent movement had slid his balls up over my chin and onto the bridge of my nose, leaving the base of his still erect cock resting partially across my lips. His dick was sticky from Melinda's pussy, and smelled like her, but I couldn't help opening my mouth slightly and extending my tongue to rest lightly against him; there was no way he'd feel such a soft touch when his mind was concentrated elsewhere.
"It's just another mouse, Mom," Robin complained. "They chew up stuff in the closet and I can hear them in the walls at night. You promised you'd do something about it."
Pausing with her hand on the closet doorknob, Robin's mom decided not to open the door after all. Seeing a mouse was something she couldn't stand, and Robin knew that.
"I'll ask your father to pick up some more mousetraps," she promised, beating a hasty retreat from the room.
Once her mother had entered the bathroom and closed the door, Robin opened the closet a crack and whispered something to Dave, reaching in to give his dick a good squeeze and a few promissory strokes before she shut the door again. While the light shone in Mike had risen to hands and knees, perhaps thinking we could make a break for it, and gave me a truly amazing view of his manhood directly over my face. Once Robin closed the door again he had relaxed back into his previous position with his balls now resting directly on my eyes and even more of his hard cock on my face. I was truly in ecstasy!
"What did she say?" Mike whispered, his voice sounding muffled to me as his thighs were against my ears.
"She said to be quiet, and not to even move because her father is directly below us and the floors of this old house are even thinner than the walls," Dave replied, his voice barely above a breath.
"For how long? I'm killing Jimmy," Mike said.
That's me, Jimmy, although when I'm dressed I prefer Jenny.
"Be quiet, and be still," whispered Dave.
For the first time ever I loved Dave; I didn't want Mike to ever move. Unable to speak I reached up to pat Mike on the shoulder and gave him a thumb's up to let him know I wasn't in any pain or anything. Reaching back Mike briefly gripped my hand to let me know that he had gotten my signal, and likely thanking me for being such a good sport about it all. I nearly giggled with joy as his actions rubbed his wonderful cock
against my mouth. Teasingly I eased my tongue back out seek his flavor beneath that of Melinda's pussy juice, again being sure not to do anything he would notice. It may have been nothing but my imagination but he tasted better than anything I had ever tried before. It was all I could do not to grip his ass cheeks in both hands and begin the wholesale licking of his thick meat.
After what must have been an hour, but felt like nothing more than a few minutes to my joy-drenched mind, Robin came back to the closet door and told us that her parents were sitting out on the front porch and, while we couldn't leave, we could at least move to a more comfortable position and perhaps even get dressed. Reaching beneath the bed she pulled out a handful of clothes and thrust them into Dave's arms before reaching down to again teasingly stroke his cock back to full hardness. Once she had left Dave pulled a cigarette lighter from the pocket of his pants and lit it, giving Mike enough light to extricate himself from off the top of me. I really didn't want him to go. In the few seconds of light I noticed that he was still rock-hard and ready to fuck; likely thinking of getting back between Melinda's thighs. Working ourselves around in the tiny closet we all regained our feet as Dave tried to separate the clothing.
"Great," he whispered. "I've got my underwear and pants, but no shirt. All you've got is a shirt and a pair of socks."
"Just put on what we have," Mike whispered back. "We'll get the rest later."
I said nothing, just happy to think of Mike's cock still naked and hard next to me.
I was still wearing all my clothes, of course; panties, bra, pantyhose, skirt and top. My shoes were female as well, black with a low heel. Standing between them as I was, I barely came to either of their chins. The closet was deeper than it was wide, so we were crammed together tightly enough there by the door that I could feel either man's hard cock against my stomach or back with a slight sway in either direction, with the clothes of the two girls keeping us from proceeding deeper into it unless we lay back on the floor. I waited until Dave next squirmed about, seeking a more comfortable position and then used the cover of his movement to push myself firmly against Mike, his big dick pressing into my pretty pink top just below my breasts.
"Quit shoving Dave," Mike growled. I didn't move as Dave whispered an apology. I just stood very still hoping that Mike would eventually accept that I was unable to back away because of Dave. Gloriously he did.
"We gotta get out of here," Dave whined. "Maybe we should make a break for it? Run out the back or jump out the window or something?"
"Don't be stupid, Dave. We just have to wait until the Dean and his wife go to bed. It can't be long now," Mike replied, his words trailing away as we heard the Dean come back into the house, announcing loudly that he was going to work in his den. That was the room directly below us.
We stood there quietly for a while, listening to the Dean's wife humming as she did some laundry downstairs. Easing ourselves about as quietly as we could we sought to avoid cramps from the tight quarters, although I didn't let Mike's cock get away from me for even an instant if I could help it. Quietly I was trying to rub away a crick in my neck when Mike gently took the back of my head in one of his big, strong hands and urged me to rest my face on his chest.
"It's ok, you can rest your neck this way," he whispered directly into my ear, causing a bolt of pure lightning to leap from my ear to my cock and back again. I did so gladly, leaning totally against him and reveling in the scent of him as I glorified in the thick wedge of meat pressing against my ribs. What a perfect man.
We stood there for most of another hour, with Mike maintaining his erection the whole time. I began inventing fantasies about the situation; pretending that it was contact with my body that kept him hard and they all ended up with me on my knees sucking him and then being thrown to the floor of the closet for the glorious fucking I so deserved. Finally we heard the Dean's voice again, and a few doors being closed. This time it was Melinda who opened the closet.
"Hurry and get dressed," she whispered, seeing Mike's still rampant cock. With a twinkle in her eye she immediately grabbed him by his dick and playfully tugged him out
of the closet. Muffling his groan he followed her to the bed and enjoyed a hand-job as she used her other hand to feel about under the bed for rest of his clothes. Not being able to find them without letting go, she looked at me and lifted an eyebrow. Understanding her request, I knelt down and crawled partially under the bed, finding the rest of Dave and Mike's clothes well back from the edge. Hoping that Mike was enjoying the view of my panty-covered behind I grabbed the clothes, pausing only to hold Mike's shorts to my face for a moment before I crawled out. I had been doing his laundry for three weeks now, and was well acquainted with his wonderful smell. Disgusted I found Melinda sucking Mike's cock like it was the last she'd ever see. Tossing the clothes on the bed I crossed to the door of the bedroom at Dave's hissed command and kept watch on the hallway, seeing Robin standing down the way watching her parent's bedroom.
Thankfully Melinda didn't have time to bring Mike all the way to orgasm. For that I was thankful; to see him come in another woman's mouth would have been more than I could bear. I'd hate to burst out in tears in front of them all. Once the boys were dressed we followed Melinda out into the hall one at a time; Dave first, then Mike, then me. Aware of the creakiness of the old floors and especially the stairs, we moved slowly and cautiously, taking our time before we placed our full body weight on a spot. It took an eternity for us to make it down the stairs and only a split second for it all to go wrong.
Dave had made the front door, which was being held open by Melinda, and was waiting on the front porch as Mike crossed the floor from the stairway to join him. I was on the third stair up, slowly stepping on the second, when the door to the Dean's bedroom suddenly opened. Robin immediately went into action, speaking to her father as she pretended to be on her way to the bathroom, but the Dean brushed her off and headed for the stairs.
"Just a second Hon, I need to get something from the den," he explained. It was only three good steps from his bedroom door to the top of the stairs and I barely had time to reach the floor before he saw me. The look of surprise on his face quickly faded to another emotion I wasn't certain about, but I knew what it meant for me; I was a dead man. An expelled dead man.
"Hello there, you must be a friend of Melinda's," he stated, coming down the stairs quickly with his hand outstretched. Glancing back over my shoulder I found Melinda standing next to me, a terrified smile on her face. The front door still stood ajar but there was no sign of my two 'friends'. Stunned and uncertain, I managed to put out my dainty little hand as Melinda introduced me to her father.
"Yes dad, this is my friend Jenny. She's a freshman at the girl's college," she said, speaking of the small private college that shared the same town with the Dean's sprawling university. I was trembling as we shook hands; not believing for a moment that the man was actually mistaking me for a real girl.
"So nice to meet you, Jenny. Any friend of Melinda's is welcome here. Out kind of late aren't you?"
I couldn't think of anything to say but again Melinda came to my rescue.
"She needs some help with her schoolwork and I offered to tutor her. This was the only time she could make it."
A sucker for anything academic, the Dean gave me a wink before he replied. "That's fine, Melinda. Perhaps you should ask Jenny to spend the night? That is, if her parents wouldn't mind?"
"That's a great idea dad, thanks," Melinda said, her fake smile quivering. "We'll call them in a bit."
Smiling in return the Dean stepped aside, offering me the stairs with a flourish. With Melinda's hand on my arm I made my way upstairs, my legs trembling so badly I probably would have collapsed without her aid.
"What a perv," Melinda whispered as we reached the top of the stairs. "He watched you all the way up the stairs just so he could peak up your skirt."
Embarrassed beyond belief I kept my eyes focused on the floor as we made our way back into the girl's shared bedroom. Robin looked as scared as Melinda but neither could match the fear living in my chest.
"What are we going to do?" Robin whispered, having heard the conversation with her father. "He can't stay the night!"
Melinda shook her head. "No, but she can," she said, staring meaningfully at her sister. It took a long moment but Robin finally accepted it.
"Ok, but there's no way we can let mom see... her, and not dad either in the light of day. She'd never pass."
Turning me towards her Melinda looked me over. "No, but with a little makeup and some different clothes, I think we can get her out of the house."
No one asked me what I thought, they just made their plans without me. As a pledge to the fraternity I was supposed to be under their control this evening, just like I was Dave and Mike's, so perhaps they were just continuing along in the same vein. I only tried once to make a suggestion, and was shushed before I even got a word out.
"You'll need to practice a more feminine voice before you speak," Robin cautioned. "Your mannerisms are good and your body looks great, but your voice is a dead giveaway."
"Not that it couldn't work with a little practice," Melinda added. "But it is your biggest flaw."
Nodding I accepted their decision and stood awkwardly as they discussed my fate. To let me leave now would look suspicious since we were supposed to be studying and the girls eventually agreed on keeping me there that night but set their alarm clock to get up extremely early. That way they could hopefully sneak me out of the house before their parents got up and explain that I had an early class.
Dressed in one of Melinda's nightgowns I spent the night in her bed while she slept with her sister. Torn between fear and excitement I slept very little, extremely conscious of what I was wearing and where I was sleeping. My few moments of sleep were broken by dreams of being fucked by Mike in this same bed; just as he had been fucking Melinda in it a few hours before. When the alarm went off, I was awake and ready to make a break for it. Unfortunately Robin found that her father was already up.
"He has an early meeting, so he's downstairs making himself breakfast," she had explained. "We can't him see Jenny; he'll get busted for sure."
Melinda knew what they had to do. "Then let's fix her up so dad won't be suspicious; I'll find her some clean clothes and you work on her makeup. Jenny can go downstairs and straight out the front door so that if dad does see her, it'll be only a glimpse. I think she can pass if we do a good job."
With no other options the two put their plan into motion, and shortly I was wearing makeup and had my hair combed out and fixed into a very feminine style. My clothing was a simple pink dress but my underwear was very elaborate with stockings and even a corset to give me as womanly a figure as possible. The full slip felt wonderful against my stocking-clad and freshly shaven legs and even to me my reflection looked fully like a woman. The whole transformation had taken the two girls only about forty-five minutes to complete.
"Come one, let's get her out of here before mom gets up," Robin said.
Clutching my borrowed purse I walked as swiftly as I could in the short-heeled pink shoes, stumbling twice before we made it down the stairs. The Dean was waiting for us at the bottom.
"Good morning girls," he said, looking me in the eye. "Jenny, it's so nice to see you again. I trust you slept well?" he asked, dropping quick, leering glances at my breasts. He really was an old horn-dog.
Remembering what the other girls had said about my voice, I squeaked a soft, "Yes sir," and tried to keep it shut.
"Would any of like some breakfast?" the Dean asked us, but he was really asking me. Thankfully Robin interceded for me at that point.
"No thanks dad, Jenny has an early class and has to get going. She's almost late as it is."
Unwilling to let the cute little angel from his sight so easy the Dean offered to drive me in his car. I didn't want to protest too much as I was uneasy about my voice and before I knew it I was being ushered out to the Dean's audi.
"Don't you worry at all, Jenny," he soothed. "I'll have you to class in just a few moments. I looked fearfully towards his daughters, who looked every bit as frightened as I was. They could do nothing else for me except give sad little waves from the front porch of their home.
Trying to remember every feminine mannerism I had ever seen, I waited while the Dean opened my door for me and made sure to tuck my skirt under me as I slid sideways into the seat. I had seen women do that when wearing a skirt and apparently I did it well as the Dean kept that sick little smile of his plastered on his face as he ogled my legs. The trip to the private school went well enough; the Dean asked me many personal questions but took my one or two word answers easily enough as he much preferred to hear himself speaking. He told one or two jokes, using the deliverance of the punch line to place his
hand on my knee and squeeze. The old perv was actually hitting on me!
Once we came close to the girl's school I began to get worried anew; I knew nothing of the campus and had no idea where to tell him to drop me off. Luckily I saw a number of people filing into a big stone building and I pretended that was where my class was. Hurrying around to my side, the Dean opened my door and gave me his hand to help me out of the car. Forgetting to keep my legs together I inadvertently allowed him to see quite a bit more leg than I had intended, and true to form he took it as a hint that I was flirting with him, causing him to hold onto my hand just a little tighter and longer than he might have otherwise. I made all this worse when I accidentally bumped the back of my hand into his pants as I hurried past him, the unmistakable outline of an engorged cock easily identifiable. Smiling the Dean took my accident as intentional, and gave my butt a brief squeeze as I escaped.
"You're certain you have to make this class?" he asked, the leer on his face leaving no doubt as to what he had in mind.
"Oh, ah yes, I do. It's very important," I all but whispered, hurrying away towards the building.
"Well you come back to visit any time, Jenny. You're always welcome to stay the night with me," the Dean called. I knew exactly what he meant; he had not had a slip of the tongue. Waving goodbye I hurried along the walk, watching from the corner of my eye to see when his car was out of sight so that I could change direction. Unfortunately the old perv stood by his car and watched my wiggling ass until I had to enter the building to get out of his sight. Only then did he leave.
Ignoring the strange looks the other girls in the building were giving me; they obviously didn't know me and wondered who I was, I left by the backdoor and hurried down the nearest street on the lookout for the Dean's car. I didn't want to accidentally be seen and perhaps even picked back up by the man. Seeing a payphone I found enough change in Melinda's purse to make a call and with trembling fingers dialed the frat house. It took some time to convince whoever answered that I needed him to wake up Mike, but eventually I was able to explain where I was and beg a ride. Thirty minutes later I was safely in his car.
"Damn, Jimmy, you look great," he blurted as I slid onto the seat. Mortified I looked at him, causing him to blush and backtrack quickly. "Sorry," he said. "I forgot myself. But I can't help noticing that you look... well... just a real girl. I wouldn't have known you if you hadn't gotten into the car."
Blushing, I murmured an explanation about the girls' helping me and loaning me the clothes and followed with a quick summary of what had happened after he and Dave fled. The only thing I left out was the Dean's flirtations, particularly when he rubbed by ass. Mike apologized for abandoning me and said the two boys waited outside the Dean's house for more than an hour before deciding that I must have slipped out another way. Since the police hadn't come, they figured that I hadn't been caught. He also expressed envy at spending the night with both of the sisters.
"That must have been something; three beautiful girls in one room!" he joked.
Thrilled with his compliments I didn't know how to handle them and as soon as possible went quiet, but couldn't help sneaking peaks of him out of the corner of my eye. I knew that I looked better at this moment than I ever had in my life and being treated as a beautiful woman, even if my friend was only teasing me, felt absolutely wonderful. What my eyes saw with my sneaking glances was Mike wearing ratty old jeans and a white t-shirt, his hair uncombed from sleep. What my mind saw was Mike totally nude and with an erection sticking upwards so far it was interfering with the steering wheel. Giggling despite myself I imagined taking him into my mouth and sucking his dick limp simply for safety's sake; we didn't want to be in an accident did we? Unaware of the reasons for my laughter, Mike joined in.
"Yeah, I guess we did dodge a big one this time, didn't we?" he said.
I agreed and he went on talking, telling of legendary fraternity pranks of the past. I alternated looking him in the eyes when he glanced my way with staring at the bulge of his package when he watched the road, finding that I was thoroughly enjoying myself now that the danger of being caught in the Dean's residence was past. We were nearing the campus quickly, too quickly, and I began to wish that we had a lot further to drive. Once we got back to the frat house, my hazing would end and I would have to give up my panties and skirts. Desperately I tried to think of some excuse to remain dressed the way I was and in remain in Mike's company but nothing would come to mind. Thankfully Mike came to my rescue.
"Hey, I'm hungry. Want to stop for breakfast?"
Mind spinning I stuttered out a 'yes'. What did agreeing to this do to my image in Mike's eyes? I knew I was gay and totally gaga over him but he certainly had no clue. By agreeing to be seen in public after hazing was over, it was possible that he might understand that I wanted to be dressed this way. If he ever suspected that I was secretly in love with him I just knew that I would die. Whatever he was thinking remained a secret, and the dear boy just kept telling frat stories until we pulled into a small restaurant.
"Wait, don't get out," Mike said when I reached for the door handle.
Leaping out of his side of the care he hurried around to my side and opened my door. Flustered I daintily spun my legs around and took his hand as I stood, my confusing obvious to him. Laughing he explained, "Hey, you've got to believe me when I say just how amazing you look. You're the hottest girl I've ever been seen with and I think we should try and fool everyone in the restaurant if we can."
Blushing I stepped aside so he could close my door before I spoke. "You really think we can fool them?"
Grinning he slid an arm around my waist. "No problem; no one is going to mistake you for a man, trust me. Besides; even if we do get caught we'll just say it was a last minute stab at hazing you before we let you join the frat. No one is going to question me on something like that."
Too excited at having his arm around my tiny waist, I didn't bother to argue. He could have told me the moon was made of cheese and I would have just nodded dumbly at that point. Guiding me along, we entered the restaurant and asked for a booth in the very back. Mike continued to act the gentlemen and seated me before sliding in beside me. Again I felt a thrill to have him sitting beside me, our hips touching in the narrow booth, but I had no idea about how I should react. Was he just playing a game or was he flirting with me too? Either way, I was on cloud nine. Naturally something arose to break my reverie.
"Mike, I need to pee," I blurted, barely remembering to keep my feminized voice at a whisper. How could I have agreed to come here? There was no way I could hold it throughout the entire meal and the ride home.
Failing to see the problem Mike simply slid out of the booth and took my hand. "So go use the ladies room; no one will question you."
I protested by Mike's assurances and the tightness of my bladder soon convinced me to make the attempt. Nervous and trembling I approached the bathrooms with fear making my heart pound beneath my corset. The place was nearly empty but I just knew that someone, likely a woman, would immediately raise a ruckus when I entered the ladies room. Despite my fears I pushed the door open with issue and found myself alone.
Making use of the nearest stall I began to relax as my bladder emptied and by the time I was finished had regained my composure. Pausing at the mirror on the way out I took time to touch up my makeup before leaving, passing an older lady at the door without a problem as I left. Happy that I had passed such a trial, I floated back to where Mike awaited me and gleefully slid into the booth after he stood.
"See?" he said. "No one even noticed, did they?"
Agreeing that they didn't, I breathlessly commented. "I can't believe no one can tell I'm not a girl!"
"You should take my word for it Jenny; you look nothing like a boy anymore. You are one hot babe," Mike said, handing me a menu.
The meal went great, though I hardly ate anything. Mike continued to be a gentleman and, even better, treated me like a lady. Our waitress suspected nothing, or was one great actress, and by the time Mike was finished wolfing down two stacks of pancakes and half my eggs we had laughed until my side hurt. Regretfully I agreed that the meal was over and allowed my dream man to lead me back out to the car. Once seated, I managed to 'accidentally' flash Mike a little more leg than I had when I got out, my mind raced again with possible ways to delay our arrival back at the frat house. I truly didn't want my time with Mike, dressed as I was and being treated like I was, to end. Alas, it had to, and within moments we were home.
"Oh," Mike added as we got out of the car. "I spoke with Dave and he agreed that you could be my roommate if you want; once you're officially voted into the frat. You may not realize it yet, Jenny, but you've got a permanent favor owed to you by him now; you witnessed him having sex with a minor, so he won't be so quick to mistreat you in the future."
Blushing with joy I couldn't respond verbally so just nodded instead. Sleep in the same room with Mike? It would be wonderful, and heart-breaking, but that was probably the only thing that could have cheered me up now that it was time to abandon my female persona for good.
We entered the frat house with Mike's arm around my waist. He had whispered in my ear that it might be fun to see if we could fool the other guys before I changed and I had quickly agreed. Still acting the gentleman Mike held the door open for me and kept on hand in the small of my back at all times; giving me goose pimples of pleasure at his touch. Disappointed, we found no one else around, at least not on the ground floor. Surely some were in the various bedrooms but for the moment the rest of the house was quiet and abandoned. Regretfully I trudged upstairs, hoping that I wouldn't start crying. I loved how I looked, how I felt dressed this way with Mike's strong arm around me.
"Wow, Jenny, your legs are amazing," Mike whispered as he followed me up the stairs. "Did you shave them?"
Nodding that I had, I was still too choked up to talk, I led the way towards the pledge room where my stuff was located but found the door locked.
"What the...?" Mike asked, as surprised as I. "That door doesn't even have a lock, not since Moose broke it off last year when one of the pledges tried to hide from him. It must just be stuck."
Standing mutely by I watched as Mike tried to force the door to no avail; it simply wasn't going to budge. Finally Mike gave up.
"Oh well, it doesn't matter. You're staying with me now anyway; let's just go back to our room."
My heart skipped a beat at the words 'our room', but practicality burst forth. "Mike I need my things; I don't have anything to change into."
Stepping back Mike looked me up and down admiringly. "We'll get someone to open the door later and if you need something to wear you can borrow something of mine. Besides," he added, looking meaningfully at my legs, "you look too good to change; you should just stay dressed like that."
Ignoring the joyful choir that burst into my life between my ears, I made the excuses that a real man would make in such a situation but they sounded lame to me even as Mike brushed them away.
"You look good, you've already told me how comfortable those clothes are; just keep wearing them, no one but us will ever know. For all I care, you could stay dressed as a woman forever."
Light-headed with joy I allowed him to slip his arm around my waist and lead me to the top floor, where 'our' room was located. Once we were inside he immediately stripped off his t-shirt and jeans, tossing them back into the corner he probably took them from when he came to rescue me. Trying not to stare at his bulge I stood uncertainly in the very center of the room, unsure what to do with myself now that I was here.
"That's your bed," he pointed. "I sleep here," he continued, turning to the closest bed and dropping on it. I noticed that his was unmade and mine was just a bare mattress. "I hope you have some sheets and blankets."
Surprised I said that I didn't as I daintily sat upon the bed, keeping my knees together this time as a lady should.
"No problem, you can buy some later. Until then you can share my bed," Mike said patting the mattress beside him. "Come on over and check it out; it's not all that soft but it has served me well," he laughed. Amazed, surprised, and with a glimmer of hope in my heart I crossed the room and joined him, sitting down as close to him as I could manage. Could he possibly be teasing me? He was obviously flirting now; was it just a ruse? A trick? One last attempt at hazing? If so I was falling for it; sitting as close as I was couldn't be construed as anything but what it was; I, a woman, was demonstrating my interest in a man.
We sat together for a moment before Mike stood back up. "I think I'm going to grab a shower," he said, then unceremoniously stripped his shorts down to the ground. Stepping from them his thick member, already semi-hard and bouncing slightly as he moved, he moved a little closer to me spoke.
"Well, pledge, I assume you're still wearing your panties, right? Let's see them."
My mouth opened but I couldn't speak. Hazing was supposed to be over; I didn't have to do what he said, but the idea of lifting my skirt for him while he stood naked before me was too good to pass up. Keeping my eyes glued to his cock I stood, lifting the hem of my dress to give him a good look at my long legs covered only by my nude-colored stockings. My panties, a soft pink pair made of silk, were clearly visible to him. Fascinated I watched as his cock pulsed slightly, obviously getting harder as I looked.
"Very nice, Jenny," Mike said, his voice softer now. I looked up at him, finding his eyes focused on mine. "Now turn around, and show them to me from the back."
My heart racing I turned around, spreading my legs wide as I tugged my dress up even higher and then bent at the waist to present my girlish bottom to him. To my amazement he stepped closer to me and touched me on the butt cheeks, softly stroking them were they were covered by the panties.
"You are so damned hot, Jenny! I should make you suck my cock for turning me on like this. Do you want to join the fraternity, Jenny? Would you suck my cock to earn my vote?"
Turning slowly, my mind made up, I met his eyes as my right hand slid out to
gently take his hard member.
"No, Mike, I won't. But I would suck my boyfriend's cock, if he asked me too," I whisper.
For a long moment he said nothing, just staring into my eyes. His mischievous smile was there, the one that had often forced me to find a quiet corner to masturbate in, and finally he replied.
"Well Jenny, your boyfriend is asking; will you suck my cock for me?"
Moaning in absolute lust I slide to my knees, gripping his beautiful cock in my hand as I began stroking it gently. I wanted him so badly I couldn't wait to taste him, but because one part of me still thought that this was some kind of trick I didn't want to hurry through it too fast. I stroked it lovingly for a time, inspecting it as it completed its journey to full erection, then began licking it firmly as I had dreamed of so often. Beginning at
the base I licked every glorious inch of his manhood until it gleamed wet with my saliva. Pausing briefly to suck his balls I next nibbled my way up his length and wrapped my lips around the head. Looking up I caught his eyes and gazed loving up at my man as I gave his cockhead a thorough tongue lashing. Unable to hold back any longer I sucked deeply on his dick and then, our eyes still focused on one another's, I lowered my mouth down onto him.
I had practiced deep throating on vegetables once my interest in Mike began undeniable, and so I had real plans at taking all of him down my throat. That quickly proved to be impossible, it would take a lot more practice before I could do that to something this big, but I managed to take a lot of it. Gripping his cock with both hands I began sliding my face up and down his thick pole, licking, sucking, and gently biting it all the while. His precum was flowing and tasted as wonderful as I had dreamed that it would, and all thoughts of making this first blowjob last fled from my mind as I started moaning and slurping his cock. It was as if my whole life had faded away and was beginning anew at that moment. I had no memories, no past; I had only been created just now and my sole purpose in life was sucking Mike's cock.
Moaning and groaning I slid my mouth over his dick as I came in my panties. It was the best orgasm of my life and I wanted more; I wanted to taste his sperm. Stopping me briefly, I almost cried when he made me open my mouth, Mike sat down on his bed and then motioned for me to continue. Dropping to my knees between his spread legs I was so happy to feel his cock slide again across my tongue that I did cry a little, but they were tears of joy. Jacking his dick I gave him a serious tongue-lashing and then slid his powerful meat back into my mouth where it belonged. Sucking and bobbing, I felt his cock get even stiffer as I sucked him and I knew it wouldn't be long before he came so I redoubled my efforts, wanting only to taste the reward I had earned. Feeling one last twitch I knew the time had arrived and I pulled back just enough to allow his first salty burst to spray onto my tongue before plunging his thick cock back down my throat. Groaning deep within his chest Mike blasted jet after jet of his delicious seed into my waiting mouth.
Sitting back I smiled up at him as I savored his delicious seed, softly nursing on his still-hard cock as I did. He smiled back and then patted the bed beside him.
"I hope you're ready to lose that cherry, Jenny."
I said nothing, there was nothing to say. I just smiled all the wider and climbed up next to him. Being in a fraternity was going to be better than I had ever imagined.
Mark, a loner who grew up in a small Kentucky town, has always been a lonely and tragic figure. When his mother passes away it marks the end of his former life and forces him to rebuild as he moves away to attend college. Helped by Todd, his only friend, Mark finds himself anew but struggles to find happiness as Megan, his alter ego, insists on a place for herself.
As with many of my stories there are a lot of real-life facts contained within. Yes, some of these events really did happen. Reality diverts into fantasy at some point; I leave it to my readers to choose what falls into each category. This is, intentionally, a long story.
The situation I have found myself in didn’t arise overnight. It took the events of my whole life to finally lead to this moment. To accurately share my present I need to tell you some details of my past.
Hillbilly Girl
Chapter 1
Life in the mountains of Kentucky is a little different than in other places and my own even more so. They found my father’s body in a tent on top of Yancey’s Peak when I was only four. He’d died drunk; smothered by his own vomit, and was naked; they never did find the bimbo who’d been there with him though my mom had her ideas. He’d left us alone and broke with no way for my crippled mother to provide for us. I guess I learned to have a good work ethic; food-stamps didn’t pay the bills. Even Mrs. Priddy’s small son Mark understood that.
I worked hard at the part-time jobs I could find. I’d do most anything from mowing yards (tough in the mountains where level ground doesn’t exist), to working in the general store to babysitting. Hard work was nothing to me though I was never a large boy; in fact I was always small for my age and mistook occasionally by strangers for a girl because of my long hair. I tried to date but didn’t have much luck; I never had enough money to take girls out to eat or to the movies. My one indulgence was sports; though I wasn’t very good at most things and really didn’t want to play in some. When you go to a high school as small as ours everyone has to participate if we’re going to have enough kids to put out a team. Like in football for example; even with my reluctant participation we only had nineteen players my senior year and that’s even counting one eight-grader who was kind of big. I’d return kickoffs or punts and did ok; I was pretty fast. I was better at baseball where my weak throwing arm could be hidden at second base and even better at cross country and track where my little legs could easily out pace most competition. I never excelled at anything well enough to draw the attention of any colleges, but I enjoyed it enough to deal with practice schedules in and around school work and jobs. Not that my grades didn’t suffer; they did, but I maintained a solid C average.
The summer after my senior year my mom passed away. She’d been dying for years so it while it wasn’t surprising it was devastating all the same. We didn’t own anything that mattered; no house or car, so I managed to get rid of everything in one extended yard sale... everything but a few personal possessions and some clothes. Not all of them my own.
When I was small, probably about six or so, though I don’t clearly remember my age, I started trying on my mother’s clothes that I found in the dirty clothes hamper. I’m not sure why, but it was fun and I did it in secret, somehow knowing I shouldn’t let my mother know. Eventually I graduated from panties and panty hose ‘fresh’ from the hamper to bras and slips borrowed from my mother’s drawers. She still had clothes from her younger days when she and my father were newly weds and by the time I was ten or eleven I started trying on her corsets and ‘naughty nighties’. By that point masturbation was a big part of my dressing up though my emissions were nearly nonexistent and I loved to imagine that the girls from school were wearing identical underwear as I was at that moment. Somehow it brought me closer to them in my own mind. Not once did I have a fantasy about another boy; I was not interested in being gay.
For the most part I was healthy, though I did have one issue come up that really depressed my mom, and also me at first. The doctor explained it all but to a twelve year old it didn’t make a lot of sense.
My mother was concerned that I was nearly thirteen and had yet to grow any body hair. Also; my voice hadn’t changed and remained the same clear tenor it had been when I was little. Mom began to worry about me, normal I suppose because of her own history of health issues, and when she suggested that I go to the doctor for a physical I agreed. I would have done anything to ease her mind. Being in no hurry to grow hair in my armpits I wasn’t concerned. I was active and had no doubts about my ability to pass the physical but that’s the way life is; imagine my surprise when I failed some blood tests.
“It’s nothing that means life or death,” the doctor explained to us when we returned for my final follow up. “Apparently Mark has a rare disorder known as Hypogonadism, caused by Klinefelter’s syndrome. It’s a genetic disorder.”
He had gone on to explain that my testicles hadn’t developed correctly and were producing practically no testosterone.
“What does that mean?”
“First of all, you may be infertile; we can test for that. You can expect your body to continue to soften as you lose muscle and gain fat. What little testosterone your body has produced is dwindling and this situation will only get worse. You’ve had this issue since before you were born, so you have nothing to feel guilty about. If you don’t begin an immediate regimen of testosterone injections and medications your body’s feminine characteristics are going to become undeniable. Some of which are already showing though it’s possible you haven’t noticed.”
Mom, of course, who didn’t entirely trust doctors after years of their failing to properly diagnose her, had a million questions and taxed the doctor’s patience I’m sure, none of which I really understood. He finally summed it up for me.
“Mark, you may develop breasts. They’ll likely remain small, but they may very well be functionally capable of creating milk under the proper circumstances. You would have probably never noticed them, thinking only that they were loose skin or fat but I assure you that they are breasts. Without the testosterone treatments they will develop and they will remain. Your body cannot produce enough testosterone on its own; without these treatments you may lose the ability to get an erection.”
Embarrassed beyond redemption at hearing the doctor speak of me having erections in front of my mother I pretty much shut my hearing down for the rest of the visit. Mom wheedled a week’s sample of the drugs from him and we left. She cried a lot and apologized to me but I still didn’t truly understand what she was upset for. My chest didn’t look like a girl’s no matter what the doctor said. Naturally we couldn’t afford the drugs but eventually I grew a little body hair, enough that my mother decided that I had ‘outgrown’ whatever condition I had and dropped the subject.
Of course this new idea increased my dressing up for a while. I liked trying on a bra, pretending that I did have breasts of my own but it was all just a joke. I had nothing on my chest besides the same baby fat I’d always carried there. I just loved the thought of dressing and acting like a girl, not truly being a girl.
Those times ended when my mother caught me. I was thirteen at the time and was sitting on the clothes hamper wearing panties and a slip when my mother walked in carrying a load of clean towels. She cried, telling me that she had been suspicious because of her clothes being in disarray but never certain. She blamed herself and wanted to know what she had done to make me do this. I cried too and said that I only did it to see what it felt like and swore never to do it again. She probably wasn’t convinced but I did avoid dressing up for nearly two years, though I would often wake up through the night after a wonderful dream of dressing and cry myself back to sleep. Finally I went to a local church that was part of the ‘Mountain Mission’ where people donated clothing for the poor people of the Appalachians. They arrived dumped in garbage bags and I volunteered to sort through one truck load. They’d been washed before they’d been sent but there was no rhyme or reason to the packing so things had to be separated into appropriate piles for distribution. There I managed to obtain a few pairs of panties and a really nice bra for my personal use. I also took a slip, though it was very boring; made of cloth and with no feminine, lacey touches. These I hid inside an old T.V. tennis game (a Pong knockoff that had never worked) in my closet and so my secret dressing continued. I longed for panty hose and a truly feminine slip, not to mention the dresses I had only barely begun to try but I didn’t dare let my mother catch me again. It was enough. It’s not like I had a lot of time to indulge myself anyway.
I learned to be so careful that my mom never again suspected; at least I don’t think so. In all those years of dressing up my mom was the only one to ever catch me until the summer between my junior and senior years. I was sixteen then and was working in the local general store as well as part time at a sewing factory where I was paid to load the cloth remnants into an incinerator three times a week. I also had baseball games twice a week as well as a few practices but all in all I had more free time that summer than any up to then, so naturally I was dressing more. One particular Tuesday I was home alone; a rarity because my mother seldom left home because of her physical ailments. My uncle had taken her into Lexington that day for some medical tests and I knew they’d be gone for hours. I had showered and put on my best panties along with my bra and slip before walking into my mother’s room to gaze longingly into her closet. Most of her clothes were utilitarian but some were amazingly nice to someone like me. I would take out the special ones one by one and hold them before me as I gazed into the full-length mirror. It was as far as I dared go but the desires were killing me. I knew that the softest, silkiest slips and panty hose were right there in the room with me and that with only a very minimal effort I could quickly be dressed completely as a woman. It was enough to make me swoon with emotion. I was holding my mother’s wedding gown up to my chin when I heard the noise behind me.
To be truthful I had heard the noises earlier but had discounted them. We live well off the main road with the nearest neighbor more than a mile away. Our driveway was a dead end and was maintained by the owner of the property primarily to give access to the field his father had cleared behind the old house we now lived in. The only visitors we ever had were my uncle and the farmer who always came on his tractor to work the field. In either case we always heard them coming long before they reached the house. I had no friends to speak of and not even traveling salesmen came back here. I had to ride my bike out to the road just to catch the school bus. When I heard the faint noises of someone in the yard, I just assumed it was a stray dog or the old tom cat that lived in the barn. I never expected anyone and in particular never dreamed that Todd Hammond would be in my yard, much less looking in my mother’s bedroom window.
I guess I should explain who Todd is. His father Duke owns the farm and house we live on and he’s their only son. He and I had gone to school together from kindergarten on up but had never truly been friends. Acquaintances would be more accurate. We nodded and occasionally spoke in passing as minimally as two of the only six boys in our class would need to. It’s not that I disliked him, despite his obvious flaws; we just never really ‘clicked’. His flaws? Well for one thing he was much bigger than me, standing at least a foot taller than my 5’4’’. His thick blonde hair and good looks made him the center of attention for all the girls in my school, leaving me and my black mop almost unnoticed. Where I was slim he was muscular. Where I relied on quickness he relied on power and was the standout on virtually every sports team in our school. He was the school stud and I was the school pansy. Not that he ever bullied me or mistreated me or anything; he didn’t need to. He was so overwhelmingly my superior in every way that I was no competition to him.
“What the Hell are you doing?” he had chortled, catching me in the act of daydreaming about the wedding dress. The windows were tall and open and the only thing separating us was a window screen. In defense I had spun towards him, holding up the dress to cover my slip but it was too late and we both knew it. My life was over whenever he chose to talk about what he had just seen. Naturally I began to beg for him not to tell anyone, telling him anything I could think of to convince him that I was just ‘fooling around’ and wasn’t really a guy who wore women’s clothing. He only laughed and waved away my excuses then walked around the house and came in the back door.
Petrified and very nearly wetting myself in fear I had quickly hung the dress back up and rushed to meet him in the kitchen. Standing before him wearing only panties, bra and slip I was prepared to debase myself in any way he demanded to keep him from telling on me. I was ready for any insults he cared to throw at me and was frantically preparing defenses to the ‘fag’ and ‘homo’ references he was about to shower me with when he surprised me by asking if he could borrow my old baseball glove.
“Excuse me?” I stammered, so shocked I couldn’t comprehend what he was saying.
“Your old baseball glove, the one with the broken laces?” he had explained, telling me that his sister had left his outside and it had gotten too wet to use in practice later. “I’ll re-lace it for you if I can borrow it for a few days.”
Stunned, my heart barely beating, I led him back to my room still in my feminine ‘finery’ and there dug my old glove out of a box in my closet. Taking the glove he thanked me and simply turned to leave! I chased after him, begging him again not to tell anyone about me and swearing that I’d never done it before and never would again. Finally he turned back to me as we entered the kitchen and said simply, “Hey, don’t worry about it.” Then he left the house, climbed on his bike, and rode away.
I quickly removed my girl clothes and spent the rest of the day crying in my room. I didn’t go to practice that evening and told my mother that I was sick. My life was over and I frantically tried to think my way out of the predicament I was in. There was nothing I could do. Todd knew about my dressing up and soon everyone would.
Chapter 2
Two days later we had a baseball game and I had to show up. I avoided Todd and stayed as close to the dugout door as I could. Every time someone laughed I nearly cried, because I knew they were talking about me. I went 0 for 4 and made two errors, easily the worst game of my life. As soon as the game ended I ran for my bike and fled for home; hoping to avoid the beating I would take when the local kids learned that I was a ‘panty-wearing sissy’. I knew that no one in my rural town would ever believe that I wore girl’s clothing and wasn’t gay, and being gay in rural Kentucky was not a safe thing to be. I didn’t even get out of the parking lot before I was stopped by Todd’s dad in his pickup truck.
“Throw your bike in the back,” he yelled, being mostly deaf. I knew I couldn’t say no without hurting the old man’s feelings and did so expecting the worst. I tried to salvage something by climbing into the back with my bike but was ordered into the cab with him and Todd. As I slid in I kept my eyes downcast, answering Mr. Hammond’s conversation with minimal replies without ever lifting my eyes from my dirty knees. Finally I couldn’t stand it any longer and sneaked a look at Todd, expecting to see his look of derision and so suffer again my shame. He wasn’t even looking at me; instead staring out the windshield as if considering something. Finally he did look over at me, giving me a little half smile but saying nothing before returning to his contemplation. We left the truck at their house and I rode my bike home without a word from Todd, other than a ‘thanks’ as he tossed me my now re-laced glove.
As far as I know Todd never told anyone. After about two weeks I accepted his silence on the subject as an unspoken promise not to reveal my secret. Another two weeks after I had accepted his promise I was back in panties again and began to feel friendship towards him. Not that I’d ever hated him before, but despite the arrogant confidence he always exuded, I had now seen another side of his character I wouldn’t have imagined. He was really a nice guy. Not that we hung around together more; he was still the BMOC and I was as far from it as possible, but he was never impolite to me, not even when football practice began and we were daily naked around one another in the team showers. He never acted self-conscious around me or gave me a second glance, really. Obviously I didn’t like guys and didn’t look at the others when they were naked but I made a concerted effort not to even glance at anyone or give Todd any hint that I really was gay. Not that I didn’t notice certain physical attributes; no guy can shower with others and not occasionally, accidentally, notice the size of their cocks, particularly when mine was so much smaller than everyone else’s. Todd’s, quite naturally, was easily the largest of all. I’ve always heard that a large dick gives a guy confidence. Well, if that’s true then Todd’s confidence was well earned and it’s quite understandable why I have none whatsoever. To further embarrass me during these times were the slight protuberances on my chest. No, they weren’t really breasts but my nipples were a little larger than the other boys and the only fat on my whole body seemed to concentrate there. I changed my shirt quickly and showered with my back to the others, always ‘accidentally’ holding my arm or a towel just perfectly to disguise my weirdness. No one ever mentioned anything.
I finished out my senior year confident that my crossdressing secret remained my own, and Todd’s, and returned to my routine of dressing whenever I could find the time. I still masturbated to thoughts of being with women but did occasionally widen my fantasies to include actually being a girl, though I never included a man in my conscious dreams. I had one or two night-time dreams about me as a woman with another guy, who was sometimes Todd, and these disturbed me greatly; even driving me to a week at a time here and there when I would give up dressing altogether. Eventually, however, I always returned to my panties, my small treasure now slightly augmented by further explorations of the Mountain Mission archives.
By the time the school year was closing I knew that mom wouldn’t be around much longer.
When our meager things had been sold I had reduced my worldly possessions to the contents of four suitcases and an old wardrobe of my grandmother’s. Inside two of the suitcases were my clothes. Inside the others were the best of my mother’s things. Included in the wardrobe was the wedding dress carefully wrapped in plastic along with her nicest dresses and skirts. Also kept were the breast forms she’d been given after her first round of cancer. Not that she had ever used them; they were still in their package. My longing to try the clothes on was temporarily muted by her death but I still had the presence of mind to keep them because I knew that sooner or later I would be dressing again. But for now, that side of my life was put on hold.
I placed my mom’s things in storage and left for college once the estate, such as it was, was settled. The timing had been good because I had needed to stay with my uncle for only a week or so before it was time to leave. I didn’t have a scholarship and had barely passed the minimum requirements but I had been accepted. Naturally I had to work to support myself as well as pay for the school but I was no stranger to that. I blew into town and had a job at an all-night convenience store before I even moved into the freshman dorm. A weekend job cleaning houses was next and a local fast-food restaurant agreed to schedule me around my classes. I bought a creaky old bike to get me around. I was exhausted and had no time for myself but without sports claiming any of my time I was doing well, even saving some cash for the future. I didn’t dress up once that whole year, though I would often lay awake at night fantasizing about it. My old life seemed a distant memory. The only real reminder I had was occasionally seeing Todd around campus.
Yes, he had chosen the same school that I had, though he was there on a football scholarship. I went to every game but he only played on special teams. The big Stud quarterback on our little team was the fourth-string safety here as a freshman. I still cheered for him. We only spoke once or twice that whole year; we just moved in different circles. He remained polite and always gave me a smile and a wave when we passed on the quad. I figured that seeing him combined with my lack of opportunity to dress up was what triggered the recurrence of my dreams.
They were more intense now; with me always as a woman or at least dressed like one with Todd invariably somewhere around to hold my hand or even kiss me. I was mortified! My thoughts on the purpose of these dreams were wild and varied; either I needed to swear off dressing forever and remove the lure of my mother’s things back home in storage or I needed to find a way to dress as often as possible so that I could ease my desires properly while fantasizing about women. In desperation I tried to date any number of women on campus without success. Desperation is not an attractive attribute I am sure, particularly when you are as small and forgettable as me. I even tried to avoid any place where I occasionally passed Todd and tried to change directions if I saw him coming my way; just so he wouldn’t smile at me. I didn’t want to give those stupid dreams any more fuel. I was not gay!
Chapter 3
By the time my freshman year ended I was almost desperate for an opportunity to dress up. I would catch myself walking through a department store, stopping to stare longingly at some feminine garment or another. The knowledge that my personal stash of clothing awaited me back home, in particular that beautiful wedding gown, was almost more than I could bear. I was desperate to feel that soft garment sliding down onto my feminized body, whispering its silken message as it eased down over my slip. But even if I did reclaim my things, a three-hour or more bus ride away, I had nowhere to wear them. The crowded dorm was not an option and once the summer break began I had to be out of there anyway. I needed somewhere to live.
The day I moved out of the dorm I moved into an efficiency apartment. Sixty dollars a month with all utilities paid. A virtual castle, I am sure. Cold cement block walls surrounded a tiny second floor rectangle room that was divided by a similar, partial block wall into living room/kitchen, and bedroom/bathroom. Between the kitchen and the tiny bathroom was a closet with a water heater but room enough and more for my few clothes. As soon as I could take off from work I went home, shipped my girly clothes back to my apartment, and gave the wardrobe to my uncle. I never planned on coming back.
I was so thrilled to hang my dresses and skirts up in my closet! They were mine! And hanging right there in the closet for all to see! Not that anyone could see them, and no one ever came over, but still the thought gave me a thrill. I admired how they looked and moved them to the front of the closet so I’d see them every time I opened the door. I then took the next couple of days and immersed myself in femininity; staying dressed every second I could when I was home. I finally tried on ‘my’ wedding dress and it was every bit as glorious as I had imagined. I tried out a fantasy where I was a girl getting married and, not having any other guys around, chose Todd as my fantasy husband. Nothing gay about it, mind you; he was just there to supplement the real fantasy by giving me a reason to wear the dress. Things were going along splendidly as I pretended to march down the isle, but then went horribly wrong as I got carried away in the moment and pretended to kiss my new husband.
Every time I dress up I invariably finish by masturbating, though my ejaculations are almost non-existent. That time I almost didn’t need to touch myself as I very nearly came when I fantasized about kissing Todd. I was so guilty I nearly tore my dress getting it off and once again cried myself to sleep. I knew that I wasn’t gay; I wouldn’t allow myself to be gay, so why did I have to be cursed to enjoy dressing like a woman so much? It was natural that dressing would lead me towards that, I assumed, but men kissing men no matter what they were wearing was sick and I simply wouldn’t allow it. I did, however, return to dressing the very next day though I was more careful about my fantasies after that.
So my summer routine was set. I worked long hours every day at a variety of minimum wage jobs but took Saturday mornings off so I could cruise the local yard sales. If I was home, I dressed up or was asleep and eventually began sleeping while dressed after I bought my first night gown. I bought a single bed, though it was almost too big to fit into my ‘bedroom’, and then an old couch that was broken through on one end and likewise dominated my TV-less living room. I slowly pieced together enough mismatched dishes and pots and pans to make living possible. I also augmented my feminine wardrobe and bought some wigs at yard sales though I rarely wore them and even bought makeup from the Convenience store I worked at, ringing it up when everyone else was on break. I worked with almost all women there and they liked to take magazines from the rack like Glamour and Cosmo to read on break. They rarely if ever returned them so they’d be there for me to absorb when I took my break. I all but memorized them. Practicing with the makeup became a nightly ritual and I never dressed without my breast forms. All-in-all I was pretty happy, so long as I avoided thoughts of men when I masturbated.
When the fall classes started I reenrolled and adjusted my work schedule to compensate. I wasn’t making as much money now but I had saved up some and was able to get by. I chose my major; education, and loved the thought of teaching a class of young kids while dressed as a woman. “We love you Miss Priddy,” they’d say. It made me very happy in my dreams. Todd came back to school as well, after returning home for the summer. I saw him once as I left the library. He smiled and waved. I walked home smiling like an idiot. I didn’t see him again for more than a week, and then not under the best of circumstances.
It was a Friday evening and I was freshly showered and dressed in a light pink sleeveless dress as I cleaned my apartment. It was light and airy and perfect for a ‘girl’ trying to keep cool as she worked. I still didn’t work on Saturdays and was preparing for a glorious night of being Megan when there was a knock on my door.
No one had ever knocked on my door. Not a neighbor, not even the landlord; I’d been anonymous since day one in my crummy little apartment. After making sure the curtains and blinds were properly in place, all the apartments opened up to the outside, I quietly eased over to my door and look through the peephole, to find who else but Todd standing there. I almost died!
He knocked again. This time he called my name. “Mark? You in there? I know you are; your bike is here. I got something for you.”
I said nothing, trembling in fear at being caught by Todd again. Perhaps I had convinced him that the first time he had caught me in panties was simply an aberration but if he found me here, now, wearing a dress he’d truly know my secret. A secret I never wanted anyone else to know. I kept silent, easing back from the door. He was persistent.
“Mark? I have a letter here from your uncle. He asked me to bring it to you but I didn’t know where you were living. Took me some time to find you. Mark? Open the door and I’ll give it to you.”
I said nothing, standing still and trying not to breathe. We must have stood that way for five minutes; he waiting for me to open the door, me waiting for my heart to explode. I could only stare at the doorknob that I only then realized was not locked. It seemed like hours before he spoke again.
“Ok, I guess you’re not home,” he announced, though why he would say anything if he believed that I couldn’t imagine. “I’ll leave the letter here,” he said, his voice muffled as he bent over and tried to slip the envelope under the door. Finding that impossible, the gap was too narrow, he mumbled something and then grabbed the doorknob, giving it a quick twist he pushed the door open slightly and flipped the envelope inside where it drifted lazily down to land atop my pink shoes. Almost he pulled the door back closed to leave but belatedly, almost comically, realized what he had seen. Pushing the door back open he followed my pink shoes up until he looked me in the eye.
Chapter 4
“Hi, Mark,” he said, giving me that familiar grin as he came into my apartment. Bending down he picked up my uncle’s letter and handed it to me. “Sorry, I thought you weren’t home. Here’s a letter from your uncle; he asked me to give it to you.”
Stammering a ‘thanks’ I dropped the dust rag I held and shakily took the envelope, fixing my gaze on it as I trembled in fear. He’d caught me again, and this time I knew he wouldn’t let it pass without berating me somehow. I couldn’t have brought my gaze up to meet his if he’d held a gun.
“So how you been?” he asked. “I was surprised to hear that you didn’t go home for the summer. Your uncle wanted to write you, but the only address he had was at the dorm, so he asked me to look you up.”
Taking a step around me he looked over my tiny apartment. From there he could see everything that wasn’t in the bathroom, because the closet door was standing open with my dresses on display. My bed was covered with panties and clothes I had intended to try on later and there was little doubt that my feminine wardrobe was much larger than my male one. I knew I was dead. I couldn’t say anything.
“Nice apartment,” he laughed. “Well, not really but at least you have some privacy. I’ve been accepted to a frat, so I’ll be living there now.” I still couldn’t comment. I’d heard about the frat; all the football players on scholarship joined it after their freshman year. “In some ways, I envy you having your own place. I sure get tired of stepping over people in my own bedroom, and all the parties are ridiculous.”
I still said nothing, though I did manage to lift my eyes.
“Can I borrow your bathroom,” he asked, turning to meet my gaze with his own. Were his eyes always so blue? I couldn’t remember.
“Yes,” I stammered, seeing that he was waiting for a response before going. Throwing me his famous half-smile, known back in high school as the ‘panty-peeler’, he went into my bathroom and shut the door. Belatedly I remembered that the sink was covered in makeup and two pairs of nylons were hanging over the shower curtain. Shaking my head I realized that it didn’t matter; there was nothing else he might find that could embarrass me worse.
Shortly he left the bathroom and came back to where I still stood, facing the front door and gripping the letter in my little fist; the pink of my fingernails smudging on the paper. I’d been in a hurry and hadn’t let them dry properly. He towered over me, looking down on me in all my feminine ‘glory’. He didn’t even chuckle.
“Well I guess I should go,” he said, “looks like you’re busy cleaning up. Stooping down he picked up my dust rag and handed it to me. “Maybe I’ll come by another time.”
With a smile and a wave he left, pulling the door gently closed behind him.
My dreams were incredible that night. I spent all day Saturday awash in guilt over them. Unconsciously I not only continued to remain dressed, but wore my frilliest, sexist clothes. Once I realized what I was doing, I felt even worse, but I didn’t change.
Chapter 5
I went to the first football game of the season that Sunday and did something that I had never done before. Underneath my regular clothes I wore a pair of panties. I wasn’t sure why; I’d always been scared to do it before, but it felt wonderful to be out in public knowing what I was wearing. Todd played a little, no more than a few plays, but I cheered for him just the same. I didn’t see him again for two weeks, but it was once again a Friday night when I heard a knock on my door. After seeing him through the peephole I swallowed my fear and just let him in; it was a little late to worry about what he might think of my choice of wardrobe. This night was one of my yard sale specials; a pleated white skirt that hung to my knees and a white blouse that did little to hide the lacey slip I was wearing beneath it. At least the slip concealed my bra, though he had to know I was wearing one the way my B cup ‘breasts’ were pushing out the fabric of the blouse; my breast forms seeing daily use now.
“Hi Todd,” I sighed, stepping back to let him in. He flashed me a ‘panty peeler’ and brushed past.
“What’s up, Mark?” he asked, flopping onto the ‘good’ end of my couch. “Not house cleaning again are you?”
“No, just relaxing,” I said, sweeping my skirt beneath me as I joined him on the couch, consciously sitting as far from him as I could without sliding off into the hole. He wanted something; his silence surely had a price. He’d come back to blackmail me now, I was certain.
“You don’t look relaxed,” he smiled, leaning back and looking very relaxed. “You look like you’re not happy to see me.”
I hesitated before speaking. “Todd you can see what I’m wearing and you know I’ve been dressing like this for a long time. You know it’s not just a passing fad. I appreciate that you’ve never told on me but it makes me very uncomfortable when you see me like this.”
“Yeah and you’re getting really good at it. You look dead-on like a girl, dude.”
Cutting my eyes towards him I thank him. “I know you’re just being nice Todd; I know I don’t really look like a girl. I just want you know that I’m not gay, ok?
Laughing he unabashedly met my timid gaze. “Gay or not gay, I don’t care. I’m not here to ask you out. You like dressing like a girl, that’s fine with me; and you do look good, whatever you want to believe. If I didn’t know you, I’d never guess that you’re a guy.”
Breathless and pleased I looked towards the floor and just grinned stupidly. I wanted to thank him because I worked hard at being a girl but I couldn’t find the words. The thought that I might be going to pass out flashed through my mind.
After a short pause he continued. “I came by to see if you wanted my old TV set. I just got a new one and was going to sell it but then I remembered you didn’t have one.” I pulled my eyes up from the ground to meet his sparkling blue ones just as he asked, “Are you interested?”
Stammering I reminded him that I wasn’t gay, causing him to laugh loudly.
“No, silly, are you interested in the TV?” he chortled.
“Oh,” I said, my face glowing with embarrassment. “I suppose, if it works and it’s not too expensive,” I managed, tearing my eyes from his and lowering them accidentally to pause at his lap, then on to his shoes. Why had I looked at his lap?
“Great, I’ll go get it. It does work, though the colors are kind of off, but it won’t cost you anything.”
Ignoring my protests over him giving it away for nothing he dropped me another panty-peeler and went out the door. Shortly he returned and easily carried the large, old set in though it was almost too wide to fit through the door. He was amazingly strong, particularly in comparison to me. It had to be from the early seventies if not older but he plugged it up and proved to me that it worked fine. The colors seemed to be primarily blue but since our TV growing up had been a black and white I was enormously pleased to have it.
“Are you sure I can’t pay you for it?” I gushed, my emotional roller coaster leaving me almost giddy.
“Nah, I don’t want your money,” he laughed. “Just let me come over and hang out some times, so I can get away from that monkey house I live in.”
“Sure, but, you know I like to dress... like this...” I stammered. “If you let me know when you’re coming, I can have on my regular clothes so you won’t be uncomfortable.”
Again he shared a laugh and flashed his cute grin. “Don’t change clothes on my account. I think you look great. You dress however you want; I won’t mind.”
Overwhelmed at the thought of someone, anyone, coming around to see me, much less seeing me dressed as a woman, nearly took my breath again. I never thought that it would be possible to have someone accept me as I was, without judging me. Almost, I came very, very close, to throwing my arms around his neck and giving him a hug. I managed to alter my momentum into a squeeze of his arm as I thanked him.
Chapter 6
Football season being as hectic as it is Todd didn’t come over again for almost three weeks. Two straight away games were followed by an unseasonably cold home game that was played on a Thursday night. I went to the game, naturally, and was able to get a really good seat because the crowd was smaller than normal. Since I was able to wear a coat I treated myself to not only wearing panties but also a bra, though I left my falsies at home. So scared was I that even though I found myself sweating beneath the big coat, I kept it on, petrified that someone would see my bra straps. Todd saw me in the third quarter and waved from the sidelines. I can’t remember if we won or not. The very next evening he came to see me.
I was just starting supper when he knocked. I was wearing a cute little one-piece outfit that combined a bib overall top with a jean skirt. I was wearing a tight white tee that clearly revealed my lacy bra and the bib pockets hung low while the galluses ran to either side of my breasts giving the illusion that they were bursting out of the top. If Ellie-Mae Clampett wore skirts this is the outfit she’d have worn. I’d just shaved my legs so even if I say so myself; I looked good. I’d spent hours getting ready and knew that I looked damn cute. Todd complemented me right away.
“Damn, you’re hot hillbilly girl,” he said. My hands were clasped behind me as I smiled up at him pushing out my breasts at his admiring gaze. He was really my only friend and to hear him compliment me at the only thing I was any good at made me feel wonderful. He surprised me when he reached out a finger and pushed on my left breast.
“Are those real?” he asked. Shocked, I could only shake my head.
“No, they’re not,” I finally replied, vowing in my heart at that moment that I would find a way to make them real and thinking for the first time in years about my genetic disorder.
Nodding he gave the same breast a good squeeze. “They sure feel real,” he marveled, running a finger over the bump on the very tip. “I mean; that sure feels like a nipple.”
Hardly able to breath from the emotions running through me I stammered that they were fake breasts and had built-in nipples then tried to change the subject. Obviously I didn’t mention that my real nipples were suddenly so hard they almost hurt. My face was red and I was so flustered I blurted out what was supposed to be a joke.
“Well you can’t just grab one without making the other one jealous,” I said, immediately regretting my words. His spontaneous grasping of the one, even though it wasn’t really a part of me, had sent a shockwave through my body to that place hidden inside my panties. I wasn’t sure how I felt about that, I wasn’t gay after all, but my ‘joke’ now made it sound as if I was asking him to touch me.
“Oh, sorry,” he laughed, gently give my other breast equal attention. It felt almost as good as the first time. Trembling, I looked up into his eyes as he held my breast, feeling very weak and vulnerable; as well as close to orgasm. Still smiling he finally released his touch and moved to drop onto the couch.
I quickly finished the meal, for which he enthusiastically complemented me for my cooking skills. I thanked him of course but how can you ruin a meal of soup and salad? We took our time eating as we caught up on the details of our recent lives and then moved to the couch to watch TV. I sat near the hole as to give him the arm rest but somehow he inadvertently sat closer to me than he meant to and we ended up virtually hip to hip. He apologized and eased away but only a fraction of an inch. I decided to be a good hostess and not complain, but instead leaned back and tried to concentrate on the show. For some reason I couldn’t get into it, though Todd sure seemed to enjoy it.
During a commercial he looked at me, I just happened to be looking at him at that moment so our eyes met, and thoughtfully he asked, “You know, I feel odd calling you Mark when I come over. You don’t look anything like a ‘Mark’. Don’t you have another name I could use so I don’t feel weird?”
Concerned, I asked, “I didn’t know you felt weird around me. I told you I don’t have to dress like this if it makes you uncomfortable.” I was suddenly on the verge of panic. Todd was my only friend; I had no one else in the whole world except a seventy-five year old uncle who rarely spoke. If my dressing like a girl made him uncomfortable it was only a matter of time before he drifted away.
“Are you crazy? I love how you look,” Todd said, giving me a panty peeler. “I’ve told you that you make one amazingly beautiful woman. I just thought you might have a girl name to go with your girl self. But if you want to just be Mark…”
All I heard was that he thinks I’m beautiful. He had to repeat himself before I manage to stammer out my girl-name; one I’d only decided on that week.
“Megan… my girl-name is Megan.”
Smiling again he leaned back, sitting so close that we were touching all along our sides. “Megan it is then. You look like a Megan.”
Chapter 7
I’d always been a quiet boy and one prone to spats of melancholy. My periodic dressing as a girl would make me happier, though after my orgasm the inevitable guilt would hit me and I’d be even more depressed than ever. After Todd started to call me Megan the guilt seemed to wash away; he accepted me for who I was, at least the part-time me that never left my apartment. For some unknown reason my dreams were particularly intense during that period of my life and always involved Todd kissing me or holding me, even lifting my top to kiss my breasts, but they failed to spark much guilt. I would wake up with his kisses still burning on my lips and reject the guilt; accepting the dreams as simply unconscious reactions to my dressing up and nothing to worry about. I knew that I wasn’t gay, after all, and if I had a few dreams… well, I wasn’t hurting anyone. I knew that one day I would meet the right girl and my urge to dress would go away so a few dreams now meant nothing.
It was also during this time that I began researching a way to enhance my natural breasts in some manner, or to be truthful, I put more serious effort into it. I’d long thought that it would be wonderful to have real breasts but Todd touching me had become a game with us; he’d sneak up behind me in my apartment and reach around to grab them both, then pretend to apologize because he didn’t realize that I wasn’t a real woman. Sometimes I’d stand there with his arms around me, his hands clamped to my breasts as we laughed and feel my body demanding that I make the breasts real. Nothing that couldn’t be reversed, of course; I didn’t want to become a woman, just enhance the joy I received from my pastime.
Breast enhancement surgery was an option, except for the cost and the fact that everyone involved would know that I was a guy. But it was reversible. I’d learned of several herbal substances that would help but at this time I really looked into the details. The side effects concerned me but the worst seemed to be a slight feminization of the body and loss of body hair. I wasn’t too concerned about those, being small and feminine looking even when I didn’t dress up. Estrogen seemed promising but I had no ready supply of that, so I went with an herbal concoction of various things and brewed them into a tea that I drank twice a day. It didn’t taste great but I learned to tolerate it. It was a few weeks before I noticed anything but over time I became confident that I was slowly on my way to having my own breasts. Wouldn’t Todd be surprised when he grabbed a handful of the real things!
By the end of the football season Todd and I were spending more time together. He’d come over most nights and we’d study together. I tutored him on grammar and spelling and he’d help me with math. I’m terrible at math. We’d move the TV to the floor and drag my tiny desk, the only place I had to put the TV, over to the couch and we’d scoot up next to one another and hit the books. My grades, never a strong point, suddenly showed improvement and I had to admit to myself that studying had never been so much fun. So long as Todd was there to help me, I’d gladly study all night.
It was after completing one such marathon study-fest that Todd broke my couch, or at least made it worse. He’d just put my TV back on the desk and flopped down on the sofa near the end with the hole. He broke straight through, halving the part of the couch that was still capable of being sat on. I fell on him twice trying to pull him out and he took both opportunities to paw at me. We laughed so hard I almost peed myself. He’d always made fun of my couch but I couldn’t afford anything better. After that we were almost sitting atop one another when we watched TV. Sometimes one of us would sit on the floor and lean back on the other’s legs. That was nice, but I preferred to share because it was so much more comfortable. Todd, being so muscular and wide at the shoulders had to put one arm across the back of the couch to give me room to squeeze in next to him. We discussed his putting it around my shoulders, he was afraid I would be offended, and finally decided that just draping his arm around me wouldn’t hurt anything; we were just two good friends watching TV. I had to admit that it was more comfortable; that way I could scoot in real close to him and not have to hang out over the hole.
Other than going out drinking with his friends from the frat, Todd was at my apartment whenever I was in those days. I still worked a lot of hours but would rush home to get ready for him as soon as I could. He always gave me an hour or so to prepare and looking extra nice for him became another game for us. My only regret from those days was Todd’s drinking. He and his frat buddies were really overdoing it. Friday evenings and most of the day Saturday were ours and Todd usually managed to drop by the other days, but his frat was famous for their parties and he was always willing to partake. He never was drunk around me, though, at least not in those days. He managed to get into some trouble but nothing serious. I got into trouble as well, though it was minor and entirely of my own making.
It was a Thursday afternoon. My last class ended at noon so I went to work at the convenience store from one to four so another girl could go to a doctor’s appointment. I was supposed to work from seven to close at the restaurant so I hurried home to get ready for Todd’s arrival at five. He was bringing takeout and we were going to have a quick meal together before I had to get ready again for work.
Knowing that I only had a few moments I didn’t get all dolled up but just jumped into the shower, taking care to keep my hair dry, and then threw on a matching set of black panties and bra, with breast forms in place of course though they were starting to get tight now that my teas were having a slight effect. Then I fixed my makeup and pulled on a simple black dress that barely came to mid-thigh before throwing my hair up into a pony tail. Todd liked pony tails and they certainly were easy. Grabbing a pair of black flats I walked into the living room when Todd knocked on the door. Smiling that he was early I threw open the door to reveal myself to only the third person who had ever seen me dressed as a girl. It wasn’t Todd; it was my landlord.
Mr. Williams was a quiet, elderly man who never seemed to leave his apartment on the first floor. He spoke gently to me when I paid the rent and if he needed to tell me something specific invariably just dropped a note in my mailbox. Now he was staring at me while I was wearing a dress entirely ‘too short for company’, as my mother might have said. In that instant my sweet old landlord turned into a depraved old pervert as his eyes locked on my legs.
“Hello, Miss,” he said, dragging out the ‘o’ in ‘hello’. “I didn’t realize young Mark had a visitor. Are you his girlfriend?” he asked, stepping into the apartment without being invited.
“No,” I stammered, involuntarily stepping back as he barged in.
“No?” he chuckled, his eyes trailing up to focus on my breasts. “Then why are you in his apartment?”
My mind didn’t always work particularly well in stressful situations. I searched for some reason why Megan should be found in Mark’s apartment when I noticed the remnant of mine and Todd’s meal from the night before still scattered across my kitchen table. Picking up the dirty dishes I put them in the sink and turned on the water.
“I’m Mark’s sister, Megan. He pays me to clean up for him,” I lied, adding some dishwashing liquid. As the water ran I picked up a sneaker from the floor and carried it to the closet.
“Oh, you don’t have a boyfriend?” the pervert said, apparently ignoring my explanation as he came closer with an odd gleam in his old eyes. “Pretty little thing like you ought to have a boyfriend.”
Again I was scrambling for a response. I was really getting scared.
“I didn’t say that I don’t have a boyfriend,” I explain, darting around the landlord to get back into the kitchen to turn off the water. “I said that Mark wasn’t my boyfriend.”
“And who would that be?” he asked, moving to stand between me and the door. I could swear that he was staring right through my dress.
What other name could I have thought of in such a stressful situation? “Todd Hammond is my boyfriend,” I blurted.
“That’s right, old timer, she’s my girlfriend,” Todd said, his powerful frame blocking out the light from the open doorway as he stepped inside. His usual smile was different now; not the panty peeler I so enjoyed but something more feral; more dangerous.
Mr. Williams immediately lost his predatory gleam as he dropped a letter on the table and darted from the apartment. “Make sure young Mark gets that,” he mumbled as he left.
I stood there after he was gone, holding myself and trembling. Todd closed the door and came to me, taking me in his arms and holding me as I cried.
“I was so scared,” I snuffled after a long while. I felt comforted there in his embrace and held him tight so he wouldn’t step back. Not yet.
“He’s gone, don’t worry about him. I’ll have a little talk with him when I leave; he won’t bother you again,” Todd whispered, squeezing me to his thick chest. I stayed there in his embrace until I couldn’t pretend to cry anymore and then stepped back, thanking Todd for his timely arrival and his reassurance.
Todd didn’t say anything, just looked down at me with his panty-peeling smile on full display beneath the most beautiful blue eyes I could ever imagine. That tiny part of my remaining maleness, pushed back between my legs as usual, was rigid from the closeness to Todd and my fears were now a memory as I looked up at him. We stood that way for long minutes as my trembling eased and my body, most of it anyway, lost its tenseness.
Looking down as he held me Todd started to chuckle until his spell of maleness finally lost its hold over my feminized self. Punching him lightly on the chest I still didn’t step away from the circle of his arms.
“What’s so funny?” I demand.
He still didn’t immediately answer. Finally he chuckled, “So I’m your boyfriend?”
Chapter 8
So now we had a new joke. Todd would laughingly refer to himself as my boyfriend and I would laugh along, calling him ‘sweetie’, or ‘honey’. My dreams certainly didn’t take it with the same humor that we did and in my nightly adventures Todd and I became very intimate. I took solace at the thought that it was, after all, just a harmless joke between friends. The letter brought by the landlord? A notice that my rent was being raised by $10 a month.
It was just after this event that I learned of a new research project being started on campus. One of the professors was going to research a new sports drink and wanted to study the effects on long-distance runners. I applied for the job as one of the research subjects and was chosen, provided I passed a physical. I was rarely sick and although I didn’t run much now I was good at it before. I didn’t think for a moment that the physical would be so thorough. You guessed it; I failed some blood tests.
“It’s nothing that means life or death,” Dr. Phelps explained, almost mimicking the words my childhood doctor back home had used years before. You have a disorder known as Hypogonadism, caused by Klinefelter’s syndrome.”
I had almost forgotten about that. Mom said the doctor was exaggerating the issue and it had never been a problem for me; I didn’t want body hair and couldn’t care less about a deeper voice, but the news made me think of my mom, which upset me a little. He offered the same testosterone treatments my family doctor had and urged me to start them as soon as possible. I thanked the doctor and told him I’d come back the next week to tell him of my decision but I didn’t go back. Starting that evening I doubled my intake of the tea.
Chapter 9
Christmas was wonderful even though Todd had to return home. We had a small dinner at my place the evening before he left and exchanged presents. I bought him a nice shirt; it was a soft blue that really set off his eyes. He bought me a bracelet with little silver hearts on it, along with three pairs of nylons, explaining that, “You look too good in nylons and don’t wear them often enough.” He was already gone home to visit his family when I found the engraving inside the bracelet.
“To my girlfriend.”
Talk about your erotic dreams. I barely slept for days after that; each time my eyes closed I would find myself in Todd’s arms, his naked body atop my own; his kisses lighting me on fire. When he next came to see me I met him at the door with a fierce hug and held him close for a long time. When finally I pulled back he asked, “What was that for?”
“Can’t a girl hug her boyfriend?” I replied. We shared a laugh at our little joke, but my heart was pounding with joy.
Chapter 10
In mid January Todd surprised me again. We were snuggled up together watching an old movie on my blurry TV, his left arm around my shoulder as I basked in the warmth of his body. We had a blanket over us as the concrete walls of my apartment were chilly at the best of times. Sometimes I had to remind myself that all of our talk of boyfriend and girlfriend were just a game. I knew I wasn’t gay but sometimes I would forget when I hugged him hello or goodbye or when he held me to prevent my falling into the hole in my couch that I really wasn’t a girl. It felt good; comfortable, but I knew it was nothing but fantasy. Todd, I knew, was still dating girls and his campus conquests were well known. Still, he always made time for me and our friendship was strong.
“Why don’t we go to a movie next Friday night?” he asked.
“I guess we could,” I reply, turning to look up at him. “But you know I’m a stay-at-home type of person.”
He shifted his weight slightly, accidentally pulling me in a little closer to him. “Well Megan needs a night out; she stays at home too much.”
Frightened I sat upright, catching his eyes. “No, Todd! You know I can’t go out as Megan! What if someone saw me? I’d die!”
His smile was as electric as ever. “No one would know you’re not a girl. I forget myself sometimes. I don’t know how you pass as a guy, anymore,” he patted my arm to calm my outbreak. “Look, I understand your feelings and I’ve put a lot of thought into this. Will you hear me out?”
“Yes Todd, I’ll listen,” I said, leaning my head back down on his arm. I couldn’t look him in the eye; there was no way he could talk me into leaving my apartment as Megan.
“Thank you. I won’t even dwell on your landlord’s reaction to you; or how I see you myself. You pass easily as a woman but you won’t accept that so I’ll skip it.”
Pleased despite my misgivings, I adored hearing Todd saying that I looked so convincing.
“You know the drive-in theater in Greenville?” he asked, not waiting for my answer. It was about twenty miles away and one of the last drive-ins in the state. “They show a double feature that starts after dark. We stay here until the sun goes down. I’ll take the bulb out of your outside light and I’ll park there by the back stairs. We throw a big coat over you and drive straight there. We get to the drive-in in time for the second feature, park in the back and we never leave the car. No one would ever see you and Megan would get a night out. What do you think?”
I carefully explained all the reasons why I couldn’t possibly do what he wanted. My arguments were well thought out and rational and I was confident in my ability to sway him. He kept smiling at me and his big blue eyes soon trapped mine and my words trailed off into nothing. At least he helped me pick out my outfit.
Things went well, though I thought my heart was going to explode from fear. I wore a dark blue dress that went to mid-calf with a longer woman’s coat and a scarf over my head. Todd removed the bulb from the light by my apartment door and we hurried down the concrete steps to the back parking lot that few people ever used. I darted into the car and hunkered down; I never did calm down during the whole ride. Todd laughed at me the whole way. I kept my face averted at the ticket booth and then we were inside and parked well away from the other cars. Despite my fear I felt excited; Megan was finally outside!
We got there a little early and watched the end of the first movie. It was a kid’s movie and kind of silly. After the intermission, that I spent slumped down in the floorboard, the lights went out again and the main feature came on so I resettled into my seat and tried to relax enough to enjoy the show.
It was cold despite the car’s heater and Todd noticed that I was shivering so he lifted the armrest to make the front seat into a bench and motioned for me to slide over next to him. I snuggled up to him but felt no warmth through our mutual coats. He must have noticed I was still shivering so he made some adjustments by opening his coat and allowing me to slide inside and he hooked my legs and lifted them up to rest over his knees. Then we took my coat and draped it over us. I was so warm and toasty I immediately began to relax. This was the same position we always watched movies in at home, though I was snuggled up to his right side rather than the left I was used to. I decided that either was okay. Soon I was enjoying the movie, and wrapped my arms around him inside our coat-cocoon and gave him a thank you hug.
“You were right, Todd, this is great,” I said, smiling up at him. He just smiled back and gave me a good squeeze.
I felt so wonderful and relaxed and despite a good movie fell fast asleep; not for long I don’t think, maybe fifteen or twenty minutes. Something funny happened and Todd chuckled and that’s what brought me back to consciousness. I went through a blissful moment where I wasn’t sure where I was but absolutely didn’t want to move and ruin the ecstasy I was feeling. Slowly my situation returned to me and I knew that my head was pillowed on Todd’s chest and my left arm was wrapped around his back. My legs were still draped over his knees and my right hand was wresting on his lap.
And that’s when I really woke up. My hand had drifted while asleep and now my wrist was resting atop a very firm, very masculine lump rising within Todd’s pants. He had an erection, caused by something in the movie no doubt! And I was almost touching it! If my hand had slipped two, maybe three inches more at the most, I would be holding him in my hand. I slipped one eye open and saw the reason for the erection; there was a nude girl’s locker room scene showing and all the sluts on the screen were topless. What a terrible movie! I wished Todd would start the car so we could leave right then!
This definitely wasn’t what I wanted, but I didn’t know what to do. If I moved my hand Todd would know that I was awake and might suspect that I had been awake all along and intentionally touched his cock! If I stayed where I was, I would be intentionally touching his dick. Todd wouldn’t know, but I would. Unsure and conflicted, I stayed still and kept my breathing steady, hoping that I could just fall back asleep and forget the whole thing but that wasn’t going to happen. I was so aware of his erection that it was all I could think of; it felt like it was burning into my wrist. My body reacted to the turmoil and my own little cock was straining to escape its restraints; not from touching Todd’s cock, just from the fear and stress. My nipples were hard as well, and trying to chew their way out from beneath my breast forms. Another ten minutes went by as I held perfectly still; trying to ignore the firmness beneath my wrist as I mentally struggled with what I should do next. Todd chose for me.
“Damn,” he mumbled, suddenly shifting his weight. He then reached beneath his coat and gently moved my hand aside, then shifted again as he adjusted his manhood to a more comfortable angle. Next he retook my limp hand and placed it back on his lap, but this time he put the palm of my hand directly on his dick, groaning as he squeezed my hand so that my fingers squeezed him.
“Oh yeah,” he sighed, easing his seat back. Petrified I sat very still, cupping and holding his dick as I continued to pretend to be asleep. I was barely breathing, I was so scared. Or maybe it was excitement; but that couldn’t be true. “You awake?” Todd whispered. I didn’t respond. “Thought you were awake,” he mumbled. “Kind of takes the humor out of it,” he added. So, placing my hand on his cock had been a joke and he had expected me to jerk it away immediately but I had missed my chance. I should have pretended to wake up then, using his words as an excuse, but I didn’t. I continued to feign slumber and left my hand right where it was for the rest of the movie and suffered mixed emotions when the show ended.
“Wake up Megan,” Todd said, nudging me gently. Reluctantly I released my grip and sat up, blinking sleepily as I helped him readjust his seat for the drive home. We were more than halfway there before I realized that I hadn’t slid back over to my seat, but was instead still snuggled up to him. Not wanting to draw attention to my lapse I just stayed there. He’d think I was still sleepy.
Darting back up to my apartment was anticlimactic and I was disappointed that my adventure was over. I gave Todd a very enthusiastic hug once we were safe and thanked him for taking me. He just smiled.
“We’ll do it again soon,” he promised, squeezing me back, then ‘honking’ one breast and then the other. “I can’t remember when I’ve enjoyed a movie more.”
Leaning back I gave him a playful slap across the chest. “I bet, with all those topless cheerleaders running around,” I stated, pretending to scowl up at him. Then I remembered that I was supposed to be asleep during that scene. Todd’s smile said it all; he’d just caught me.
“Yeah, well. I like girls,” he said, dropping me a panty-peeler before one last hug goodnight. I was too embarrassed to say anything.
Chapter 11
It was only a few days after my movie adventure that a package arrived for me in Mark’s name. I had discovered mail-order catalogues and my wardrobe had expanded exponentially. This package, however, was special.
All of my bras were ‘B’ cup to match my breast forms but since I began drinking my special herbal tea I had noticed that my tiny chest bumps had begun to expand slightly. Now the cups of my bras were so full that my forms were bursting from the top. After careful measurements I decided that my natural bust had finally reach a full A cup, so I had ordered some new A-cup bras to celebrate.
Excitedly I slid one of the bras up my arms and fastened it; then adjusted it over my breasts. For the first time in my life I was wearing a bra that actually fit! It was my own breasts that filled the cups! The way my cleavage was bulging, I was even over-filling them, as if I were larger than an A. I could feel ever glorious inch of my bra; not just the straps! It was amazing and I couldn’t wait to surprise Todd with my ‘natural’ look. My tiny cock immediately responded, which was becoming a rare event.
That worried me, of course. I still enjoyed orgasms, naturally, and didn’t want my penis to stop working completely. In the month previous I could count on one hand the number of serious erections I had had, and none of those were related to actual sexual acts. My fantasies had always been familiar and tried and true; but not anymore. I would picture a woman dressed in a similar outfit as I was wearing and with just a few two-fingered strokes I would be finished. Suddenly I found myself sporting a ‘reverse woody’, as I called them, without even thinking of a woman.
Peeling back my panties I peeked down at my hairless crotch, seeing nothing of course. Whenever I dressed as Megan I always pushed my dick back between my legs; my miniature testicles were barely there and of no consequence, and I kept my dick there by pulling my panties up tight. A few days before the movie date I had given up on my boy-briefs altogether and began wearing panties full-time, always being careful to wear low-rise panties and high-rise pants in class or at work. From that point on my cock remained pushed back between my legs pretty much all the time and since it rarely if ever got hard, it wasn’t uncomfortable. Even erect it stayed back out of the way, though it wasn’t quite as comfortable. But why had I gotten hard at that moment?
I tried to think back; to see what stimuli were common to my most recent erections. I’d had one at the movies when I was curled up on Todd’s lap, and the most erotic thing about that were the many naked girls in the locker room scene; but none of those girls had been even remotely attractive. The others had been more difficult to pin-point. Once had been while I was sitting on my couch with Todd but were just watching a game show, so no topless girls there. And this latest one was undoubtedly because of the glorious feelings from filling a bra for the first time, but that wasn’t really erotic. Perhaps it was a chemical imbalance thing; it just happened when it happened and no outward stimuli had any effect.
But now I had a new problem; my breasts were undoubtedly there and had to be dealt with if I was going to keep Megan a secret from those who knew Mark. I loathed binding them down; I’d just gotten them! But figured I wouldn’t have to so long as the weather was cold. A good, thick jacket would work wonders until the warm weather forced me to decide. Almost I was tempted to start wearing a bra beneath my coats but was concerned about the straps being seen if I bent or stretched.
Todd was supposed to come over that next Sunday for our Valentine’s Day supper so I was working on planning my outfit. We originally hadn’t planned on anything as he was going out on a date with his latest squeeze, Dalia, but they had unexpectedly broken up over something. I had to work most of the day but had managed to exchange shifts at the restaurant so I could be home that evening. Todd said that he had a present for me since I’m his girlfriend and it’s Valentine’s Day. I laughed, knowing that whatever he gave me would be whatever he had planned on giving Dalia, but that was okay. I liked feeling like a girl and a gift like that would be nice. Anything to get rid of Dalia; she wasn’t at all right for Todd. It wasn’t like I had any romantic notions about Todd; but a box of candy or flowers would be fun. That was the night I planned on unveiling my new boobs.
Well not unveiling as in showing them to him. I was going to wear an outfit that showed enough cleavage to proudly show Todd my new attributes and enjoy the surprise on his face. Just the thought of his surprise made my nipples hard; it would be a really good joke on him!
The new bra I was wearing would be the start of my outfit, along with the matching panties. They were black, lacey, and very thin. The bra itself was on the verge of being see-through but I wasn’t concerned about that; I wasn’t going to take off my top. I had a new set of black stockings with garters too and of course had to try them on with my black heels. Standing in front of my full-length mirror I was amazed at how good I looked. My nipples were just barely visible and my ass looked amazing. It was funny; I didn’t have an erection any longer though I was honestly excited by the way I looked. At least I didn’t have one until someone knocked on the door; then I began sporting my finest though of course it was hidden between my legs.
Todd wasn’t due over that day so I admit; I panicked a little as I crossed to the front door. It was locked, thank goodness; I kept it that way now that Todd had his own key. Quietly I stood on tiptoe to look out the peep hole and saw that my visitor was someone I didn’t know. At least; I wasn’t certain.
He was taller than the peephole and had blonde hair. He was handsome too, as best I could tell in the distorted image. As I was looking he knocked again, causing me to jump back a foot. Holding my breath I simply waited him out; there was no way I was opening that door.
“Guess no one’s home,” I heard the guy say. Another male voice replied. “Well this is where he always comes to; I’ve seen him.”
They continued to talk as they walked away. Who had they come to see? Me or Todd? I didn’t know the one that I had seen and knew of no reason he’d know me, but what of the other man? Feeling more bold than usual I snatched a dressing gown off its hanger and hurried to the door. At this time of day there shouldn’t be anyone around and if I was quick I could step out the door, take three or four steps down the breezeway, and see the men as they walked across the front parking lot. Maybe I’d recognize the second man and be able to figure out what was going on.
Easing the door open I looked both directions. Seeing no one I stepped slowly outside, my heart pounding like a drum, and as quietly as I could stepped around the corner and into the breezeway; almost walking into the two men as they stood there talking.
Nope; I didn’t know either one of them.
“Damn,” the blond man said, stepping back and looking down at the gap in my dressing gown. Snatching it closed I fled back around the corner and into my apartment as the men laughed at me.
With the door shut and the lock engaged I leaned against the portal and began to sob. They’d seen me and soon my secret would be out. I’d have to leave school, quit my jobs, move; my life, which was only just now worth living, was over.
“Told you Todd had him a squeeze up here,” the blond guy was saying.
The second man, a freckled kid with red hair, laughed. “And what a squeeze! She was fuckin’ hot!”
“Did you see those tits bouncing when she came around the corner?” the blond said, his voice trailing away as they left.
Chapter 12
They were friends of Todd’s; fellow football players to be precise. They’d gone back to the dorm and bragged that they’d seen the girlfriend he kept hidden away up here, expecting to have a little fun at Todd’s expense but he just laughed at them.
“They were just jealous,” he told me. “Either one would give their left nut to be with a woman as sexy as you.”
Glad as I was to have passed another test, it worried me that so many people now knew of Megan and where she lived. Only a couple of people knew where Mark lived, and only Todd and landlord had been here to see him, but the more pieces of the puzzle that got out the sooner someone would put them together.
But the things they had said! My tits were bouncing? My little A-cup boobs? I was ‘hot’? You can imagine the effect those words had on my dreams. They had a different effect as well; I knew then I had to wear a bra full-time or start binding my breasts down. They did indeed have some bounce to them; more than I could hide under a work smock or an apron. I even began to wonder if someone might have already noticed.
Valentines Day was amazing. Todd showed up wearing a suit and tie and there wasn’t a girl alive who wouldn’t respond to him, looking like that. If I was gay I’d have raped him on my doorstop but as his friend I simply met him with a big smile and gave him an enthusiastic hug. He brought me flowers and his eyes almost popped out when he saw my cleavage when I stepped back.
“Where did those come from?” He demanded, smiling. Before I could respond he thrust a finger into my cleavage and hooked my bra, pulling me back to him. Stumbling a little at the unexpected move I had to throw my arms around his waist as my breasts were pushed up against him. His finger felt like a firebrand from where it nestled; firmly touching the sides of both breasts.
“They’re mine,” I stated proudly, giving him a long look down my cleavage, hoping he wouldn’t ever move his finger.
He did eventually move his finger, but not until I promised to give him a good feel of my breasts. I put my flowers in a vase and joined him on the couch and he took a good five minutes to cup and feel them through my dress, finally pronouncing them as perfect. Out of breath from his touch, I nearly came, it took me some time to explain about my herbal teas but I don’t think he was interested in the details; he just asked if he could see them.
Laughing I told him no and we moved on to eat our dinner. I offered to listen if he wanted to talk about his breakup with Dalia, but he refused.
“Nope, tonight is just about me and my real girlfriend,” he joked. I beamed with pleasure. I was wearing the bracelet he gave me and enjoyed that joke as much as he did. I gave him his present after dinner; a new wristwatch. He then excused himself and went down to his car, bringing back a large package for me.
Flabbergasted I immediately opened it. Todd stopped me, saying that he was a little nervous about giving me the present.
“Why?” I demanded, anxious to see my gift. The box was huge.
“Because I’ve never bought an outfit for anyone before, much less for my girlfriend. I don’t know if you’ll like it and I don’t know if it’ll even fit.”
Smiling like a fool at the ‘girlfriend’ joke I said, “Don’t worry about that! I’m sure I’ll love it. If it’s the wrong size, we can just exchange it.”
Again he stopped me from opening the paper. “Look, I’m still a little nervous. Promise me this; if I give this to you, will you at least model it for me? I want to see you wearing it even if you never wear it again.”
“Of course,” I laughed. He pulled his hands back and I tore the paper from the box and lifted the top, finding the box absolutely filled with paper. I started throwing the paper out, looking for the present as Todd looked at me and laughed. Just as I began to believe the box was empty, just another elaborate joke, I found the present.
It was a negligee. It was white, it was see-through, and it had a matching breast-baring corset with white stockings. It was the sexiest thing I’d ever seen and I had already promised to wear it for Todd.
Chapter 13
Thankfully Todd agreed to take a rain check on my modeling as we weren’t going to have time tonight, plus my heart had stopped and I hyper-ventilated when I saw the outfit. He made jokes about how easy I was to trick and I tried to laugh and before he left he’d talked me into going out with him again once the drive-in theater opened up in the spring. Apparently they weren’t open year-round. He had me so confused I would have agreed to anything he said right then; modeling that white outfit for him was all I could think of. It was both the most frightening and exciting thing I had ever considered.
My dreams that night were a mixed bag of being fucked by Todd like a woman to waking fantasies of just being seen by him in the new outfit that blended together to the point that I couldn’t separate them. I awoke exhausted, stumbled through my classes and showed up to work at the convenience store with my eyes blurry, but I really didn’t feel sleepy; only terribly distracted.
About an hour into my shift I was waiting on a man who looked familiar; most people in the town pass through the store eventually, and then he recognized me.
“Oh, you’re Mark, right? Mark Priddy? You tried out for my case study on the sports drink, didn’t you?”
I knew him then. The doctor who had given me the physical.
“Yes, that was me,” I said, smiling. I hoped he wouldn’t bring up the reason that I had failed; not here where anyone could hear. “Sorry I couldn’t help you Dr. Phelps.”
He waved my apology away. “No problem; that sort of thing happens. Look; I thought of you yesterday and was going to try to find you, so I’m glad to run into you. There’s another study starting up; a colleague of mine has the grant. You would be a perfect case study for it, if you’re interested.”
Suddenly wary of what he might say I nodded and began waiting on the next customer in line. “I might be interested, but I can’t really talk about it now. Perhaps I could come by your office?”
“Fine,” he smiled, gathering up his gas receipt and sliding a business card over to me. “I’ll see you then.”
Chapter 14
The next Friday night Todd talked Megan into a drive around town. We stayed on back roads and I was glued to his side in fear, but everything went ok. No one had even a chance to see me and by the time we made the mad dash back up to my apartment I had loosened up enough to giggle about it. Thankfully Todd gave me a little more time before calling me on my modeling debut so all-in-all it was a wonderful night.
My appointment with the doctor was for that next Tuesday. I had just enough time to go between classes. I was a little early but the receptionist brought me straight back to his office. Shaking my hand Dr. Phelps asked me to sit.
“Mark I understand that you need to get to class so I’ll just lay it out for you. My colleague, Dr Thomas Josten, is starting up a study at UCLA. His grant is for the study of a very specific disorder and the psychology behind those who have it. Hypogonadism, caused by Klinefelter’s syndrome is very rare and it proved to be impossible for him to find enough people that qualify even in Los Angeles, so he’s contacted other universities to help. You are the only person I know who has this disorder.”
Naturally I was a little nervous but I knew that these studies generally paid well, so I nodded for him to continue.
“The study is divided into two categories. One is for those who have the disorder and choose to take testosterone treatments and those who choose to take estrogen and so enhance the effects of the disorder.”
“But doctor,” I protest, slightly embarrassed and confused. “I don’t take either of those.”
He smiled. “Don’t you? I know you didn’t take me up on the testosterone treatments I offered but it’s obvious to me that you have taken estrogen. Even in the few weeks since I saw you last I can tell, though I am a physician and more attuned to such things than others.”
I protested of course, but he had me and he knew it. I started to cry. My tea wasn’t exactly estrogen but they did have a similar, though lesser, effect.
“Please don’t do that,” he said, coming around the desk to pat me on the shoulder, offering me a Kleenex from the box on his desk. “I’m not judging you, just making you a business offer. One that, I think, my be in your interest.”
My tears subsiding I listened as he laid out the offer. If Dr. Josten accepted me for the study I would need to fly to UCLA for a physical and a battery of psychological tests, after which I would need to visit a local psychiatrist for frequent sessions. I would be given a free supply of estrogen for the length of the three-year study and would need to return to LA every month for tests. The pay would be substantial, at least compared to what I made then, and would accommodate my college studies as much as possible. He even went on to explain the side-effects of my taking the estrogen, though I was well aware of those.
“You’ll never be mistaken for a man again, at least not by your outward appearance. In fact, you’ll probably choose to live as a woman full-time; most people in your situation do as I understand.”
I really broke down then, and the doctor had a big job calming me down. Eventually I promised to think about it and let him know. He told me when the deadline was and I left, skipping my next class and calling in sick at my job so I could go home and cry. It was a bad day. It got worse.
Chapter 14
I cried until I went to sleep, then woke up, changed into a night gown and went back to bed. About midnight I was woken again by the sound of fire trucks passing by. Terribly depressed but unable to go back to sleep I tried to watch television but couldn’t find anything that kept my interest. Listlessly wandering around my apartment I found myself looking at the outfit Todd had bought me. I’d never even tried it on. Robotically I did so then; hating myself for my weakness over something as simple as clothing. My health problems I couldn’t help; they were genetic. But my overwhelming desire to live, dress, and act like a woman wasn’t genetic; it was just sick. Still, by the time I had finished dressing and stepped in front of my mirror to judge for myself how I looked, I was in a slightly better mood. I really looked good. My breasts were very visible through the thin material and pushed up and out proudly by the corset. My nipples were achingly stiff. My body had all the curves of a real girl, and my face was undeniably feminine. There was little doubt about it; I was a girl, or should be. There was nothing about my appearance that said ‘boy’ anymore.
That was when I heard the rattle of keys in the lock. No one had a key but me and Todd, and he wouldn’t be coming over here this time of night. Frightened that it might be my landlord I ran to the door and grabbed the handle of the deadbolt to keep it from turning, then stood on tiptoe to see who was here. It was Todd; and he looked awful.
Forgetting what I was wearing I threw open the door and asked him what was wrong. He blinked a few times, smiling at what I was wearing, and then the smile went away. Leaning against the doorjamb he mumbled something about my looking ‘good enough to fuck’ and then released a long, smelly belch before closing his eyes.
He was drunk; and as far along as I’d ever seen anyone. He was wearing a pair of sweat pants and ratty t-shirt beneath a blue jean jacket. On his feet was a pair of sneakers and no visible socks. Almost he fell backwards when the door opened but I stepped outside, my feet freezing on the cold concrete, and took his arm to steady him and help him inside. A voice laughed from the darkness as I struggled.
“See? I told ya his fuck-bunny would take him in.”
“Look at those tits! That girl needs to be fucked!”
I ignored them; Todd wasn’t just drunk he acted as if he was hurt and he stank to high heaven of alcohol and smoke. Staggering beneath his weight I dropped him onto the couch before shutting the door, ignoring the leers of the two jerks now standing there looking at me.
“Yep! He’s in good hands,” laughed the larger of the two. I recognized the shorter one as the red-head who’d been there before.
“Wish I was in your hands,” smirked the red-head, grabbing his crotch as I slammed the door in their faces. Bastards.
Hurrying back to Todd I found him unconscious and leaning dangerously far over the hole in my coach. Straining my little body I managed to push him back upright and checked to make sure he was breathing ok. Unsure what else to do I perched on his lap, there wasn’t room on the coach for me, and held his hands within my own.
“Todd? I whispered, raising one hand to stroke his cheek. On TV they always slapped people to bring them around but I couldn’t bring myself to do that. I tried stroking his face with both hands, leaving both of his in my lap as I held his dear face and called his name. “Todd?”
With a surprising suddenness Todd’s eyes popped open, finding me only inches away as I held his face and sat in his lap.
“Hey, hillbilly girl,” he slurred. “You comin’ on to me?”
Smiling at the familiar joke I sighed in relief and slipped my arms around his neck for a hug.
“I thought you were hurt,” I said, squeezing him only a little longer than necessary. “You were so unresponsive.”
Lurching to his feet Todd managed to keep his balance despite holding me in his arms. “I’ll show you responsive,” he said, smiling down at me. True to his word I felt the sudden presence of his erection pushing firmly into my butt. Stumbling a little he had to put me down or both of us would have fallen. Holding him around the waist I only just managed to keep him upright as he pawed at my breasts.
“Damn hot… girl,” he smiled, pinching gently each of my nipples in turn. I didn’t even try to pretend that didn’t feel amazing; my own erection was about ready to pop. With an effort I managed to get him to sit back down on the couch, winding up back on his lap in the struggle as he apparently wanted to remain standing. In another of his sudden reversals he stopped struggling and slid his arms around my waist as he pulled me more firmly onto his erection.
“Mmm, feels good,” he laughed, trying to dry hump me while I was still on his lap. I didn’t cooperate but tried to slide off his erection but he wasn’t having any of that. I finally gave in and remained where he wanted me. He was too drunk to know what he was doing.
“Todd? What happened? Why do you smell like smoke?
Tears filled his eyes at my question, and his erection subsided immediately. “It burned down, Megan. It all burned down,” he slurred, choking back the tears. He had awakened when the fire alarms went off, but being drunk he had barely managed to slide on the sweats and t-shirt before leaving. The shoes were his but he had no idea where the jacket had come from. The whole fraternity building had become engulfed and he and his frat brothers had staggered off into the night to find more alcohol. When they ran out of money and began to wonder where they were going to sleep it off, Todd’s buddies had thought to bring him to me. I’d never seen Todd cry before, so I was an emotional wreck as I sat on his lap and held him in my arms. Later we learned that no one died in the fire and the cause was officially listed as faulty wiring.
“I got nowhere to go,” Todd said, holding me as I was holding him. His tears hadn’t lasted long but I could feel them on my shoulder. “They told us to go to the arena but I didn’t wanna go there.”
Hugging him fiercely I intended to tell him that he was my best friend and that he could stay with me as long as he wanted or needed to; that my apartment, small and mean as it was, was empty without him here and I insisted on him staying with me. That’s what I thought, but this is what I said:
“You can sleep with me,” I blurted. I was so glad my face was buried in his shoulder, because I know I had to have turned bright red.
After a long silence I explained what I had meant to say and once I risked looking him in the face I found him smiling at me.
“My girlfriend needs some loving huh?” he said, lurching again to his feet and cradling me like a baby in his arms. “I’ll just do you right here,” he said, walking to the door and pinning me up against it as his reawakened cock began to poke randomly at my ass. We both had a good laugh at that one.
“I need to sleep,” he stated, lowering me gently to the floor. His erection was making a tent in his sweat pants and I felt the thrust of it all along my side as I regained my footing. “But I ain’t kicking you out of your bed.”
His slurring made his speech difficult to understand. I pointed out that he couldn’t sleep on the couch and the concrete floor was out of the question.
“You take my bed and I can curl up just find on this end of the couch,” I explained. He just waved my lucid explanation away.
“We can share the bed,” he said, picking me up again and staggering towards the bedroom. I again wiggled away, feeling the unmistakable bulge of his manhood trailing up my ass and lower back before I was free.
“Not yet,” I said, steering him at an angle towards the bathroom. “You’ve got to take a shower; I don’t want my whole apartment smelling like a burning house!”
He chuckled but cooperated, shrugging off his jacket as he lurched towards the bathroom. I followed along, reminding him what he was supposed to be doing as he kept stopping and staring around blankly. I swear I could have done anything to him at that moment and he wouldn’t have any idea what was going on; nor have remembered it the next day.
Finally I guided him up against the sink so I could squeeze past him and turn on the water in my tiny shower. Once it was running I found him with his shirt stuck over his head; he was just too drunk to get it off alone. Standing on tiptoes I managed to get it off of him, then reached down for his sweat pants just as he decided to turn around and bumped into me. I lost my balance, dropping to me knees in front of him as I pulled his sweats down to leave me kneeling face-to-face, so to speak, with his cock.
Thankfully it wasn’t completely erect. It had subsided drastically since he had dry-humped me by the front door but was still so big and thick that it reminded me how pathetic my own equipment was. Still partially engorged it stuck out slightly from his crotch a good inch or so before it leaned over to point towards the floor. I was so close to it that had it been fully erect it could have been pushing against my lips, so I was thankful he wasn’t hard. Trying to be professional about the situation I continued pulling the sweats down; the sooner they were off the sooner I could get up and away from his dick. Then two things caught my eye; one was that Todd wasn’t wearing any underwear and the second was that we hadn’t untied his shoes yet.
“You really are needing some, ain’t you hillbilly girl,” he laughed, pushing his hips towards me so that the head of his dick swung slightly towards me. Dutifully laughing I tried not to look at him as I untied his shoes but it was difficult to miss the gargantuan cock dangling right in front of my face. With Todd leaning back on the sink I managed to get him completely naked at last, it took much longer than I would have thought, and just before I arose I chanced to look up, catching his eyes. I must have looked pretty funny, kneeling there before him, my eyes peeking up around each side of his dick as I looked up at him. He didn’t laugh, though he did give me a panty-peeler.
“Megan you look amazing,” he said, reaching down for my hand to help me up. I couldn’t help but notice a twitch in his cock as I rose past it.
Holding on to his hand I guided Todd into the shower and told him to wash up; then had to reach in and help him with the body wash after he repeatedly dropped it. I even had to stand on the toilet to wash his hair; that boy was really drunk. He managed to wash himself from the waist down without my help; for which I was profoundly grateful though strangely disappointed. I liked helping him. This was my one opportunity to give back to him after all he had given me in our friendship. I hadn’t wanted to touch him down there but liked the thought of him needing me. I did get to towel him down and made sure that he was completely dry before allowing him into my bed.
“Wait, gotta piss,” he mumbled, turning to face the toilet. Hurriedly I reached around him and lifted the lid, then watched as his stream missed the bowl completely. He wasn’t even making an effort to aim; just stood in front of the toilet and let go! His eyes were even closed! Reacting without thinking I grabbed his cock and adjusted his aim as I yelled at him to pay attention. Todd cracked one eye and mumbled ‘sorry’ but didn’t bother to take over my job. I had to stand there holding his naked cock, the first one I had ever held other than my own, as he completed his business.
I was embarrassed, obviously, but couldn’t get over the sheer weight of the man-meat in my hand. I cupped it in my right palm, amazed at the size of the beast as I felt the urine flow through it. His bladder was full and it took a long time before his stream lessened, though it went by quickly for me. I couldn’t get over how big it was, and how much better it felt to hold his cock than it did my own. If I’d had a cock like this, I might never have tried on that first pair of panties!
After the final shake I washed my hands, used his wet towel to clean up his urine from the floor, and then led Todd back to my bed. I helped him sit down before explaining our next problem.
“Todd I have to find you something for you to wear and then change myself,” I explained, asking him to remain on the edge of the bed and not to fall asleep until I returned. I had exactly three pairs of boy underwear left to my name and they were in an unopened package I’d kept for the inevitable day when I gave up my girly lifestyle for good. Hopefully they’d fit him, though I knew they wouldn’t; my waist and his thigh were a good match for size. The issue never came up as he took charge of the situation.
“You ain’t changin’ nothin’, he croaked, snaking an arm around my waist and pulling me to him. “You look good; wanna just hold you.”
“No Todd,” I protested, giggling as he easily pulled me atop him as he lay back on the pillow and atop the covers. “You need something on, you’re naked!”
“Always sleep… nude,” he whispered. Then he began to snore.
Chapter 15
It took some adjusting but I knew where I would be most comfortable. Slipping into the gap between Todd’s right side and his arm I had to wiggle a little to get my head pillowed onto his shoulder just right. Lying on my left side like I was I placed my right hand onto his abs and draped my right leg over his and voila! I was there. Instant relaxation and contentment washed over me despite the tightness of the corset. If I was a kitten I would have purred. My apartment was always cold but with Todd’s body heat I was warm and couldn’t imagine a better pillow than where I was laying my head. I was hoping right then that Todd would never move out.
Realizing that the lights were still on I roused myself with a growl and pulled myself up from my nest. The switch was on the far side of the room, right between the closet and the bathroom, the light of which was also still on. Wedged as I was between Todd and the wall I had little room to maneuver. The foot of the bed was blocked by my low dresser so I had no choice but to climb over Todd to get out of bed but I didn’t want to wake him. Seeing no alternative I threw a leg over his waist and lifted my butt as high as I could so as to avoid brushing against his manhood. His sleeping monster was curled around with the head resting in his bellybutton at an angle. I was mostly successful in my attempt, the hem only of my negligee barely sliding across him as I half-leaped from one knee to the other over him. The bed rocked so I held still for a moment, watching the face of my beloved friend to be sure he didn’t awake. My fears were for nothing; he didn’t even miss a snore.
Climbing off the bed I stepped to the bathroom first to turn that light off but ultimately didn’t; deciding to leave it on so Todd wouldn’t be disoriented if he awoke through the night and needed to go to the bathroom. Reentering the bedroom I reached for that light switch but hesitated when I noticed Todd; his cock was hardening as I watched; stirred into life by the hem of my negligee or some dream of his own.
What was I supposed to do now? I couldn’t climb over that thing by the dim light from the bathroom, and I couldn’t simply sit and wait for it to go back down on its own! It might be hours and I was really getting tired! Deciding that I would have to step onto the bed and then step over him seemed to be the only safe way to avoid him but I would need to leave the light on. So that I wouldn’t have gotten up for nothing I took off my corset and the stockings, putting them away but leaving the negligee and white panties on; I couldn’t sleep nude like Todd though the thought of my still-hard nipples rubbing against his muscular chest almost made me strip the top off as well. I talked myself out of that by deciding that Todd wouldn’t like that; it would just be too gay if he found me sleeping half atop him with my breasts bare against his skin.
Carefully stepping up onto the bed I was lifting my leg to step over Todd when he suddenly shifted his weight on the bed, causing me to have to step back down to the floor or lose my balance. I tried again with the same result and decided that putting my full weight onto that one spot on the mattress was what was disturbing him. By this time his cock was probably three-quarters full and looked like a high hurdle to my wide eyes. I knew I was going to have to cross over him on my knees again. It seems silly now but it never occurred to me that I could cross lower down, over his legs. I was so fixated on avoiding his manhood nothing else even entered my mind. Once again the hem of my naughty-nighty rubbed against him, as did my right inner thigh. It felt like a hot brand against my leg! The heat coming off it was amazing.
I regained my comfortable place without waking him and finally allowed myself to truly relax. My right hand I left on his chest; it was too risky putting it on his stomach now that his dick was getting hard. I didn’t want to accidentally touch it or anything. That beast was still growing and soon would reach full proportions. It was so big I couldn’t pull my eyes away from it. I mean, it was right there, just across my arm from my face, and the lights were on so it was plainly in view. Todd’s dick didn’t poke straight up when it was hard, but instead ran up along his belly with an inch or so of space between his cock and his stomach. It was peering at me over my wrist with its one eye and the head looked thick and mean. What girl could he ever put that into?
Well, rumor had it that he had found plenty willing to try. Todd had been with all of the girls back home that he wanted and several more in his two years here. There was one pudgy girl in our high school named Gina who was his go-to girl when he came up dry on a date. He’d sneak over to her house late at night and she’d suck his dick, or so the stories said. Todd himself never said anything about it but Gina let everyone know she and Todd were in love. That poor girl never had a chance of keeping Todd for her own. I’m certain he never made her any promises. He wasn’t like that and didn’t need to be.
By now his cock was fully rampant and I moved my arm out of the way so I could study it. The thick, ropey veins stood out against the skin and it looked to be incredibly stiff with need. I guess Todd hadn’t gone out with anyone tonight; at least not since the fire. About then it occurred to me that this was ‘my’ erection; I’d caused it when my negligee had slid across it! I know a touch like that from a silken garment had often caused the same result in myself over the years, though not so much lately. I’d known him to have erections around me before, but they were never truly because of me; he was just responding to my acting like a girl and were of no real consequence. This time, however, he had been unconscious when he responded and that made me feel more girly; this wasn’t something that happened just from playing around; his body had responded to something that I did.
Wow! I ‘made’ that amazing thing? The skin was stretched so thin it looked ready to burst. The head was an angry red. I giggled then, glad that he wasn’t awake and demanding that I help him get rid of his erection since I was the one that caused it. Then I sobered; was I girl enough to cause an erection in a man? Or woman enough to do anything about it?
Almost in tears I thought about my life and all that had led up to this moment. Was I really a boy? I sure didn’t act like one. Was I really a girl? Small and useless as it was, I still had the wrong equipment. Gently I placed my hand back on Todd’s stomach, but this time low and to the side of his cock so that I didn’t interrupt my view. I thought of the times I had felt it. Many times Todd had jokingly used it to prod me in the legs, lower back and ass. That one time at the drive-in was still vivid in my memory, as that was the closest I had ever come to touching it erect, though it had been protected by the thick material of his jeans. Tonight I had held it in my hand while he urinated, though it had been soft. If I really was a girl I would want to hold it when it was hard; to hold it and maybe even kiss it. Suck on it, perhaps.
Shaking my head I pushed that image away. As a real girl I would only be doing those things to get Todd ready to fuck me, and even if I was attracted to men, which I wasn’t, I didn’t have the proper place to put his glorious manhood. Maybe I was feminine enough to make dicks hard, the comments from Todd’s frat-buddies seemed to say so, but I had no desire or ability to do anything else.
Sighing I closed my eyes for a moment, thinking about the study I had been asked to participate in. The estrogen would help me pass even more easily as a woman but still wouldn’t make me a real girl. Did I truly want to be a girl? How could I know for certain? Then I had an idea; a plan that might give me some indication of what I really wanted. Normally I kept thoughts of Todd well away from my mind when I masturbated but what if I took a few moments and gave in to them? What if, just for a minute or two, I pretended that I really was a girl and that Todd was really my lover? Would I be as disgusted as I assumed I would be? Would I be incapacitated with guilt? Or would I discover something about myself I perhaps didn’t really want to know?
Settling in and relaxing my body I allowed a fantasy to take control. I was Megan; a woman. I had a woman’s body and a woman’s needs. Todd, my boyfriend, was in my bed to satisfy those needs. His hard cock was waiting for me, Todd was waiting for me, to hold his dick, to squeeze it; to take his cock into my mouth and then to make love to him.
The orgasm that rolled over me set off fireworks in my mind. In my fantasy I had taken the head of his dick into my mouth, barely locking my lips around it before my tiny sex exploded in ecstasy. My fantasy self kept that lip lock even as I writhed in pleasure, having done nothing physically to myself beyond squeezing my legs together around my tiny penis which faithfully ejected a tiny trickle of fluid into my panty crotch.
My pleasure seemed to last for an eternity but it still ended far too soon. Rather than my usual guilt I found myself awash in a new fantasy; one where I lay with Todd and held his stiff erection in my tiny little fist. We were talking about nothing; just spending time together as a young couple in love will, but my fantasy self never relinquished her grip on that dick; gripping it, stroking it, studying it lovingly from only inches away. I’d never had two erections in any one day before that I could remember, but my tiny dick remained stiff and needy despite having just came. I wanted more. My clit wanted more. Did I dare take Todd’s cock in my hand? Just once reach out and wrap my hand around it and give it a gentle, loving squeeze? Did I want to risk Todd’s waking up to catch me? I had to.
Opening my eyes once my decision was made I found that I had dozed off for a few minutes. Todd’s dick had subsided in the interim and I found myself with the only erection in the bed, and I was sporting three if you counted my nipples. Disappointed I looked at his flaccid beast and wished fervently that it would regain its swollen glory, but it didn’t, though I stared at it and silently commanded it to do so. Perhaps I could make it hard again by touching it?
Todd groaned and sat up, gently slipping his arm from around me as rose. Placing one hand on the wall he staggered his way back into the bathroom, his muscular ass clenching and bunching as he stepped. Between his legs I could see his dangling dick, almost comical as it swayed and bobbed around with each movement. I watched admiringly as he again urinated, this time standing in profile to me where I lay on the bed. It looked very nice, but I liked the view better when it was next to me and hard.
Coming back to bed Todd had his eyes closed against the light, which he thankfully didn’t choose to turn off. I didn’t offer to pull the covers down and he didn’t either; simply rolling into bed in the exact same position sprawled out on his back as he’d been in previously. Once again he surprised me, leaning over to bring his face to mine and giving my astounded lips a gentle kiss.
“’Night Megan,” he slurred, and then fell immediately back to sleep.
He kissed me! I couldn’t blame it on his being drunk or disoriented; he’d called me by my own name! Nearly hyperventilating I lay gasping for air by his side, holding him tightly to me as my heart pounded. By the time I had calmed down he was back asleep and snoring again, and my next step was obvious; I had to get him hard again.
Checking once more to see that he was asleep I made my move quickly before I lost my nerve. Reaching down I took his flaccid dick gently in hand and held it for a moment; testing its weight as I had before. It stirred slightly but not nearly enough, and so I put it back down on his stomach and began stroking it softly with a finger. That brought the response I was looking for and his snake began to thicken and grow.
I held it in my palm again as it rose, marveling at the feeling of the growing erection in my fist. Squeezing softly now and again I quickly had it up half-size, and then jacked him a few times to increase the response. It was amazing and I found myself drawn closer to it; watching the head thicken with my face only inches away. As soon as it was fully erect I would let it go, or so I told myself. I didn’t let go. It was time for another fantasy.
It was an easy fantasy; I pretended I was a girl and was holding my man’s cock. It was so amazing to hold him; to know that this erection was mine; intentionally caused by me as a woman does when she loves her man. I found it impossible to keep my eyes closed and was soon stroking it and squeezing. It was amazing but I wanted more; I wanted to cum again but this time as a woman.
Easing up, never relinquishing my grip on his cock, I knelt for a moment and drank in the beauty of this man. His body was thick, muscular, and his cock as well. His abs were well defined and he was all the man any girl could ever need. I knew then that he was all I needed; and I needed him badly. Regretfully I let go of his precious manhood and placed both hands on his chest, then lifted my right leg and eased it over his waist before pausing to admire the thick cock sprouting from his groin and waiting to grind into my pussy. My own sex was hard and ready and leaking precum like I never had before. It remained pushed back between my legs and was separated from him by only an inch of air and the silken crotch of my white panties. I didn’t dare remove the panties, but the distance that kept us apart was something I could easily eliminate. With a soft feminine sigh I lowered myself down atop him.
I nearly came from the contact of my silken clit against his rampant manhood. Gazing through lowered eyes I looked at the point where we came together; the hardness of his cock and the feelings it was causing my only thoughts. If my apartment had caught on fire then I would have died, unable to tear my vision away from this living fantasy. Almost I came, but then I slid myself up along his dick, my weight supported on hands and knees as I ground my clit into his maleness, and my ‘almost’ exploded into a body shaking, mind altering eruption of delight.
Moaning and groaning I ground my clit into him, forgetting about holding myself up as I threw my head back and thought of nothing but maintaining the contact between our sexes as I pistoned my hips back and forth. There was no thought of gay or straight; I was a woman whose needs were being taken care of by her man and my orgasm washed over me again and again until I collapsed exhausted atop of Todd, then slid over into my comfortable place to lay panting and sated. Immediately a sense of completeness came over me and I ran my hands over the hard muscles before me as my body truly relaxed for the first time that I could ever remember. I barely found the strength to look up at Todd before I fell asleep; the dear man had given me the greatest sexual experience of my life and he never even woke up.
Chapter 16
If my alarm went off the next morning, we didn’t hear it. It didn’t matter; classes had been cancelled because of the fire anyway. Even after I awoke I didn’t move, lying snuggled up to Todd’s powerful body for another hour until the needs of my bladder forced me to move. He slept on until well into the afternoon, which gave me plenty of time for some soul searching.
Showering and changing delayed any serious thoughts but couldn’t stall them forever. I had to do something about getting Todd some clothes or at least washing what he had but found myself in a dilemma; the apartment’s washers and dryers were in the basement and I simply couldn’t bring myself to dress as Mark long enough to even walk down there. I could have washed his clothes in my sink and hung them up to dry but I rejected that; I had come to some realizations the night before and needed to follow through with them before I completely lost my nerve. Gathering our laundry, after spending quite a bit of timing sitting in a chair and just watching the still-nude Todd sleeping, I dressed in a simple denim skirt with a pink top and jacket and, taking a deep breath, stepped outside my apartment. Megan was going to do her laundry; no matter who saw her.
No one saw me, though the thrill that I would be seen was amazing. I started the clothes in the washer and went back upstairs to check on Todd, then returned to put the clothes in the dryer without seeing another soul. On my way back up with the finished laundry I saw my landlord at a distance, but he didn’t see me. I was almost disappointed until I got back home; Todd was still asleep and hard again, so I sat in my chair and just drank in the sight of him. That was ample compensation for a little disappointment.
When finally he awoke I watched him pee again and then sadly watched as he put on his clothes. Without underwear the sweats were quite a sight; with the steady bulge of even his soft cock tenting out in a lump down one leg. He only smiled when I giggled, despite his hangover.
“Yeah, very funny, hillbilly girl,” he said, grabbing his crotch and thrusting it at me. “Maybe I’ll take it out and beat you with it.”
We had a late lunch as we talked about what Todd was going to do about the fire. He’d lost everything, he knew, but had grabbed his wallet before he left so his father-provided credit cards would allow him to buy more clothes. I could tell he was a little sad and once we had eaten I slid into his lap and gave him a nice hug.
“You know you can stay here as long as you want, honey,” I said, falling into our pretend boyfriend/girlfriend relationship. A relationship I now wish whole-heartedly was true.
“Thanks, Megan. I may have to take you up on that,” he said, giving me a good squeeze in return. “I’ll have to come back tonight at least; but long term I’ll have to do whatever coach wants us to do.”
I understood and asked him what time he’d be back, all the time hoping against hope that he’d kiss me again.
“I’ll be back before dark. I just need to check in with coach, maybe do a little shopping so I have something to wear.”
We laughed. “At least get some underwear,” I said, playfully tugging on the waist of his sweatpants to reveal the very top of his pubic hair.
“Yeah, that may be a priority,” he said, giving me a panty-peeler as he stroked my ass through my skirt. “It’s tough going commando when you’re wearing new blue jeans.”
As we finished our chuckle I grew somewhat melancholy and lay my head onto his shoulder. “I’m so glad you weren’t hurt. I don’t know what I would do if you never came to see me again.”
Holding me tight he comforted me. “I’m not going anywhere. You’ll always be my girl and I’ll always come back to see you.” Loving the feel of his arms around me I just sat very still; not wanting him to leave.
“And speaking of seeing you; I want a promise out of you,” he said sternly, a mischievous look in his eyes.
“What?”
“I want you wear that white outfit for me again. I didn’t really get to enjoy it last night.”
Smiling I made the promise. “When you come in the door I’ll be wearing it and waiting for you just like any girl does for her man when he comes home.”
Smiling he gave me another hug, and then stood up still holding me before setting me gently on my feet. I really loved that and I think he knew. Saying goodbye he moved towards the door and I noticed that his dick had hardened slightly while I was sitting on it.
“You kissed me last night,” I blurted, surprising myself. Pausing, Todd looked thoughtful for a moment as if searching his memory, then dropped a panty peeler on me.
“Yeah, I remember that… barely. I was really out of it.” He added, breaking my heart as he did so. Pacing back over to me he took me in his arms and pressed his lips sweetly against my own for a blistering second before releasing me.
“See you later, Megan,” he called, closing the door behind him.
I just stood there. I couldn’t even open my eyes for a long, long time.
Chapter 17
I was a busy girl that afternoon. As Megan I nervously walked to the corner and called Dr. Phelps’ office, asking his receptionist to relay a message to the doctor, accepting the place in Dr. Josten’s study. Thanking me the receptionist told me to call back on Monday and I would be given further instructions. Then I called in to my jobs and told them I was sick. I didn’t have time to go to work; I needed to be ready when my boyfriend came home! No one gave me a second look during my stroll, though one middle-aged man slowed down as he drove past me. He probably was looking at the address on the building but I pretended he was looking at my legs. That was a nice little tingle.
That afternoon and evening was, by and large, a very happy time for me. At some point in the day I really accepted my femininity. My only melancholy thoughts were of the fact that I had basically taken advantage of Todd while he slept, and I felt a great deal of guilt at using his unconscious body for my own pleasure. Just the memory of that glorious orgasm made it difficult to be depressed, but I knew it was wrong to do what I had done. If I ever did it again; he would be awake and participating, though I knew that was a pipe dream. Todd was a sweet man who truly cared for me as his friend, but he was too much of a ladies man to ever want a pretend girl like me.
Returning home I cleaned my apartment from top to bottom to get the smoke smell out, even opening my window and propping my door open for the first time since I had lived there. Then I lay the white outfit out on my bed, glad that I had washed the panties that morning. Since I knew that Todd would be seeing me wearing it I took extra care with my preparations; showering long and shaving my legs and crotch close, with twice the normal amount of time spent getting my hair and makeup just right.
Nearly an hour of that day was taken up as I purged my boy clothes and carried them to the trash. It was on the way back from my last trip that I realized that I had only one pair of pants to my name, and they were a pair of blue jeans. How was I going to go to work? Smiling to myself I decided to worry about it later. Right now was a happy time. I didn’t dress until the sun was almost down, then I hurriedly slipped on my corset and negligee, giddy with the thought of being seen by a sober Todd while wearing it. I hoped he liked it… I hope he loved it, and me!
I was wearing nothing but panties and a bathrobe when my landlord knocked on my door. I started to just ignore him but, in for a penny, in for pound as they say. His eyes tried to climb my legs when I opened the door.
“Is young Mark in?” he asked as I stood impatiently with on hand on my hip. When I said ‘no’ he asked me to relay a message.
“He had to go back home for a while; I’ll be staying here and looking after his place,” I explained, hoping the old perv would just leave.
Turning a deep red the old man’s gaze returned to my gaze as he continued. “Yes, well the message is really for you. It seems that some of the neighbors were awakened this morning, really early, by a young woman… uh… feeling happy.” He looked like he was going to pass out from embarrassment. I was feeling close to joining him. A woman was moaning in pleasure loudly enough to wake the neighbors? I didn’t remember making any noise at all but it had to have been me when I was grinding atop Todd.
I thanked him and assured him that I’d keep the TV turned down next time. He accepted the lie and turned to leave when I stopped him with a sudden impulse.
“Uh, I have a message for you too, from Mark,” I said, hoping I sounded more confident that I felt. “He’s moving back home and said I could take over his lease, if you’re okay with it,” I mumbled.
Happy to see his revenue stream continue Mr. Williams just smiled and said that would be fine, so long as Mark signed a letter saying so.
I thanked him and he left; calling me ‘Ms. Priddy’. It was just that easy; no longer was Mark Priddy living here; now it was Megan Priddy’s apartment. Just as the sun went below the horizon I heard the sound of Todd’s key in the lock.
I met him at the door with a hug and a shy smile. Moving towards him slowly I allowed him a good, long look at my barely concealed body beneath the see-through garment. His smile was wide as he took in the sight; as he was still wearing the sweat pants I knew right away he liked what he was seeing. He dropped the bags he carried and after a good, solid hug he gave me another breath-taking little peck on the lips followed by a long, slow grope of my ass as he held me close. I looked at his mouth, hoping for a chance to show him how his girl really could kiss.
Still holding me tight he told me of his day. We were standing in the open doorway and I was wearing next to nothing but I didn’t care; so long as Todd was holding me I would stay there and anybody who passed by could look all they wanted.
“Coach said for us to stay wherever we could for now, and they’d make long-term arrangements for us later. Not everyone had a willing roommate ready for them and the university had to put them up in a motel, so I’m glad you were here for me.”
I could only beam with pleasure as he continued.
“I bought enough stuff to get me by,” he explained, nodding towards the bags. Normally I was always interested in shopping but now I just smiled happily; he was all I was interested in at that moment. Once he had told me everything he needed to I asked him how he liked the outfit.
Gripping my butt cheeks he pulled me up, my legs spreading naturally to encircle his waist as he lifted me up until our faces were on a level. Lowering me slightly I felt the warm bulge of his hard cock pushing up into my butt. If I had a pussy, and our clothes hadn’t been in the way, I would have slid right onto him. Leaning forward he whispered a ‘thanks’ and then kissed me again. This time he did a more thorough job of it. Now I knew why girls sometimes swooned.
Chapter 18
We ate our dinner with me sitting in Todd’s lap; taking turns feeding each other as I giggled insanely at anything he said. I pretended not to notice what I was wearing or that his rock-hard erection was trying to burrow through his sweats throughout the meal. When were finished Todd stood up, cradling me easily in his arms and carried me to the couch where we watched TV for a while as we told one another about our day. Well, Todd watched TV; I just lay with my head on his shoulder and watched him as let his hands roam over my breasts. I’d always known that he was handsome, but that night I realized that he was the most gorgeous thing on the planet! And, at least for a few weeks, he was my live-in boyfriend!
“Are you ready for bed?” he finally asked. I replied with an enthusiastic ‘yes’ before he’d even finished his sentence.
“Did you get any pajamas to wear?” I asked, praying that he hadn’t.
“No,” Todd laughed. “I always sleep in the nude. I hope that’s okay? I mean, if it bothers you I could put on some underwear.”
I assured him I wasn’t bothered in the least then luxuriated in his arms as he carried me into ‘our’ bedroom. I felt like a living doll when he did that; like I was something so precious to him that he wouldn’t allow me to walk even that short distance on my own. He sat me gently onto the bed and then retreated to the bathroom. I lay back on the pillows and thought about what I was hoping would soon happen.
What did I want to happen? Did I want Todd to make love to me? Yes! Most definitely! But in what way? Did I want him to push that wrist-thick manhood of his up my butt? Not really; that thought scared me. It would never fit and would undoubtedly hurt. Did I think he’d be content to just let me climb atop him and grind myself against him? He might let me do that once or twice; but only as a joke. There was nothing in it for him, after all, and I couldn’t take my pleasure without returning the favor. I could give him a hand job; that might work, though I would have no idea how to pleasure a cock that size with my hand; I had never needed more than two fingers for myself. And since I knew my little body wasn’t woman enough for him he’d have to close his eyes and think of some slut he’d once fucked before I could get him off, and I didn’t want him thinking of any girl but me.
Underneath all these thoughts was the realization that Todd really wasn’t gay. He liked women; he’d proved that often enough, and had shared any number of stories about the women he’d fucked. He liked ‘messing around’ with me, as he liked to say, and I hoped he’d never stop the touching and the kissing but If I pushed him too far intimately he’d eventually reach his limit and just stop coming around. That limit had to be pretty close; I never dreamed he’d actually kiss me!
Trying to relax I thought of what was coming that I knew for certain would happen. He’d be nude, in my bed, with me draped across him wearing almost nothing. I’d probably get a goodnight kiss and I could put my head on his chest and admire his cock all night long, provided I left a nightlight on.
Sighing at those wonderful thoughts I decided I could make do with that. Once he was asleep I could even rub myself off to the sight of his nude body. It wasn’t everything but it was more than I could have dreamed of even a year ago.
I watched as Todd left the bathroom and moved back into the living room, wearing nothing but his sweat pants with its delightful bulge. The muscles of his chest were very arousing; they were thick and sculpted. He came back with the clothes he had bought and quickly put them away then in one sudden and dramatic move he shucked off his sweat pants just before he turned off the bedroom light, then moved over to the bathroom to turn that one off. The sight of him standing there, silhouetted against the apartment’s only light nearly took my breath away.
I could just make out the curves of his muscular ass but the outline of his cock was clearly visible where it dangled between his legs. He stood there with his legs spread slightly in the door for several seconds as if in thought as I unthinkingly touched myself at his beauty. His body was perfect and he belonged to me.
“Do you mind if I leave this light on?” he asked, turning to look at me. Guiltily I jerked my hand out from between my legs, pretending to fluff the pillows, and told him that I didn’t mind.
“Good, if I have to go to the bathroom I want to be able to avoid tripping over stuff,” he laughed, turning around and walking back to me. I couldn’t see his face with the light behind him but I could see the soft bouncing and swaying of his cock where it dangled down between his legs. Wow.
“Besides; you’re wearing that outfit for me and I want to be able to see you in it through the night,” he added, dropping a panty-peeler on me. He needn’t have bothered; I’d gladly drop my panties for him anytime if I had a pussy to share.
He helped me remove my corset and then we settled onto the bed. He collapsed onto his back in the very middle and I eased into my comfortable place between him and the wall, his right arm around me. We talked about sleeping habits; he said he almost always slept on his back and I assured him that I didn’t need a pillow so long as his shoulder was available. We also agreed that a blanket at the foot of the bed in case it got really cold was plenty and that we didn’t really want one over us usually. I was really happy about that; I wanted nothing interrupting my view of his nude body.
After a little chit-chat about school and some of the people we both knew his eyes started to droop. I hadn’t expected anything more but was still disappointed; I could have lain in his arms talking to him like that for days.
“Come here,” he mumbled, tugging me up with the arm around my waist. I gladly did so, glad for any excuse for intimate contact. When my face was above his he gave me a long, soft, lingering kiss as I melted all over him.
“Good night,” he said, relaxing his hold on me. Sadly I started to return to my place when his arm tensed back up. “Wait a second; I want another kiss,” he said, pulling me back to him. Gladly I returned and eased my lips up against his, sighing with pleasure as he slid one hand into the back of my panties to stroke my ass crack.
“You really want to be a girl, don’t you,” he asked when our kiss regrettably ended.
Lowering my eyes I admitted that he was right. “I do want to be a woman; not just a boy dressing like a girl. I wish I had been born a girl; then I could be happy.”
“But then we wouldn’t have had a second baseman,” he teased, stroking the skin of my butt lightly.
“Screw your second baseman,” I said, lightly slapping his chest. Smiling I add, “I’m talking about my own happiness; not sports.”
“You better not screw my second baseman,” Todd said, his face mock-severe. “You’d better be screwing me; I’m your boyfriend!”
That made me laugh, but then I started crying. Todd felt bad and pulled his hand from my panties to pat me on the back and comfort me.
“I’m sorry Megan. I didn’t mean to hurt you.”
“You didn’t, Todd. It’s nothing I haven’t thought of already.”
“You’ve thought of screwing me?”
“No! I mean my not being able to screw you… I mean… Oh, you know what I mean.” He’d made me giggle. “I want to be a woman but I’ll never be and things like being with a man sexually just aren’t possible.”
“Well I think you make a great looking woman. If I saw you anywhere, I’d hit on you in a minute.”
That made me feel nice. “Thanks, Todd. You’re sweet. I just don’t know what to do. No matter how bad I want to be a woman I can’t be. My body will always be a man’s.”
He put one had back into my panties and the other slid down my top to stroke my breast. “I am not holding the body of a man. You look like a woman to me and I have proof.”
Enjoying the attention I looked up to meet his eyes. “What proof?”
“Look down there,” he said, pointing with his chin. I followed his gaze and found his rigid cock staring at me with its one leaky eye.
Giggling I reached out and took it into my hand, giving it a good, gentle squeeze. “This thing? It gets hard when the wind blows; it has nothing to do with me.”
Groaning low in his throat Todd pinched my nipple. “Are you crazy? You keep me hard all the time because you are the sexiest, prettiest girl I know. You’ve driven me insane now for months; keeping me constantly hard and not doing anything about it.”
Having taken the step of grabbing his dick I didn’t let go, but kept it enclosed lovingly in my fist.
“What am I supposed to do about it, Todd? If I was a woman I’d fuck you now; you’d never have to worry about being hard with nowhere to put it. But I’m not a woman; I don’t have a pussy!”
He smiled. “There’s other ways to help a man’s erection, Megan.”
Blushing I looked away, staring again at the thick cock in my hand. “I know about anal sex, Todd, but you’d never be able to get this in me and I don’t think it would feel very good for either of us if you did.”
“You might be surprised on that but that’s not what I meant.”
I started slowly stroking his meat. “You mean do it by hand? I could try if you think I could do you any good.”
Thrusting his hips slightly at my touch Todd groaned again. “I have no doubt you could help me that way but I was thinking of you putting that soft, sweet mouth on it.”
Surprised I stopped my stroking for a second as his words worked their way through my dull mind. Put his cock into my mouth? I didn’t know how to do that either, particularly since no one had ever done it to me. I was a virgin in every possible way and ignorant of all but the basics of sex. All I knew about sex was what I had heard Todd and others talk about at school, plus a few R-rated movies. I’d heard about blow-jobs but didn’t have the first idea how to do it.
“Are… are you asking me suck your cock, Todd?”
Pulling me back up to his face he replied, “No, I’m begging you to suck my cock, just like any girlfriend would for her boyfriend; it’s kind of a responsibility and one you’ve been neglecting.” Smiling he pulled me closer and kissed me again, this time sliding his strong, masculine tongue into my mouth.
“Please, Megan; I need you!”
That was all I needed to hear. Using my grip on his dick as my guide I lowered my face to his manhood and without preamble slipped it into my mouth.
Chapter 19
Being completely clueless about what to do I began by nursing gently on the head of his cock for a while, thoroughly enjoying the feel of his spongy head against my tongue. Instinctively I lapped at it with my tongue, getting a good taste of his precum. I’m not sure what I expected, flavor wise, but I quickly grew to enjoy both the slightly sweaty flavor his flesh and the salty yet even more flavorful fluid that came from it. All the jokes about cock-suckers I had heard as a child came back to my memory but the insult they once held had gone; I knew that this was something I was going to love.
“Lick it all, Megan,” Todd urged, his voice low and husky.
Since that sounded like a good idea to me I gladly complied. Releasing my lip lock with a ‘pop’ I slid my tongue down his length, my upper lip also in constant contact, as I explored the unimagined territory. His dick was amazing; soft flesh over a stiff iron rod that I couldn’t begin to bend with my tiny hands. I particularly enjoyed tracing the bulging blood vessels along its length. Todd seemed to enjoy that too.
“Fuck, get it all wet honey,” he groaned, teaching me how he wanted his cock sucked. I was a willing and eager student.
My mouth was already watering so it was easy to get him good and wet, though he did have a lot of dick to work on. I unconsciously kept one hand firmly gripping him at the base; perhaps I thought he might try to escape? The other ran over his chest and abs, tracing the lines between the muscles as I worshiped the man he was along with the manhood beneath my tongue.
“Be careful with your teeth,” he said at one point and since I was pretty sure I hadn’t scrapped him with them I decided he wanted me to use them in some way, so I lifted myself more firmly atop him and began to lightly bite my way down his shaft, careful not to injure him or even break the skin. He was such a mouthful even like that. This maneuver was rewarded with a thick, happy groan that thrilled me to my core, firing a lightning bolt of pleasure down my spine and radiating out from my sex. I was making love to Todd and he was enjoying it!
“Oh! Put it back in your mouth, honey! Slide it in and out of your mouth!” he panted, his cock getting harder as his heavy balls tightened into position. Always obedient I did as asked, slipping his cock between my lips and sliding it in as deeply as I could, then pulling it almost all the way back out before repeating the move. His whole body was tensing.
“Shit! Yes! Keep doing that and jack me with both hands!” he moaned, his voice revealing his deep need.
I had a deep need of my own and his need for orgasm was fueling my need to be his woman. Grabbing him gently but firmly I began to slide my hands up his shaft even as I pushed my face down it, and even the novice that I was knew that he would soon cum.
“I’ll try to warn you,” Todd moaned, his body rigid and his hips thrust upwards to meet my efforts.
I had no idea what he meant, really I didn’t, and just kept concentrating on what I was doing. My body was afire with pleasure and I was nearing my own release without even touching myself. I knew that some fluid came out of a cock at completion, and I knew clinically that this fluid was what made a woman pregnant. I had no idea that Todd’s balls produced so much greater a volume than my own did. I was hungrily sucking his meat, sliding my mouth up and down his wonderful length and working him with my hands when he suddenly groaned and launched the first spray of cum into my mouth.
Luckily for me I was on the upstroke when he blew. His first spurt splashed against the roof of my mouth and flooded it. Luckily I had been swallowing my own saliva mixed with his precum so I drank that first spurt down out of reflex without choking. The second was tougher, blasting out before I was finished swallowing the first so I had to hold that mouthful for a long second to get ready, but then the third jet emerged and I suddenly had cum leaking from my mouth on all sides of his cock. Pulling off I managed to swallow what I had as another few weaker globs bubbled up and out of him.
Surprised at his orgasm, as well as the amount, I most certainly was. The flavor of his sperm wasn’t too bad but my initial thoughts were that it felt like snot in my mouth. However one look at the bliss on Todd’s face immediately erased any misgivings I might have had. If I was going to suck his dick, I wanted him to cum in my mouth. It was a conscious decision; it was just the natural one for me. The feel of the thick wads of cum splashing against the top of my mouth had been a serious turn on and if the texture was the only thing I didn’t care for, well, I wouldn’t mind learning to live with that.
I must have looked shocked at the initial spurt because Todd immediately began apologizing that he hadn’t warned me he was about to cum. I ignored the apology and just smiled at him as I took his still-hard but softening cock back between my lips and sucked him dry, then licked up everything I had missed. By the time I had cleaned him, he was again rigid and throbbing.
“Come here, girl,” he said, pulling me up to cradle my head again on his chest as he struggled to catch his breath. My body hummed with contentment as I idly stroked his meat. I had joined his orgasm with one of my own and could still feel the slight dampness between my legs. My jaw was sore and my legs were cramping from the odd positions but I didn’t care about any of that; I had just made love to Todd and I felt wonderful.
Chapter 20
We talked for a while as he recovered, all the time I was teasing his manhood. He again apologized for cumming in my mouth but I told him not to worry about it.
“You can do that any time you want; I loved it!”
“Seriously?” He grinned. “Most girls I’ve dated won’t swallow for shit. I’ve had them get up and leave if I was just slow to warn them.”
Considering the flavor of his sperm, which I could still taste, and how womanly it made me feel to have this big, virile man cum inside me, I couldn’t imagine not wanting him to cum in my mouth. To me it seemed the ultimate validation of my womanhood; that I could, as a female, bring his big cock to an orgasm.
I explained my feelings and he just smiled, proclaiming that I was the best woman he’d ever known. I really liked that. Soon I was back between his legs, kissing and licking his rampant cock again.
“Look, it’s hard again!” I had proclaimed, reveling in the fact that I had not allowed it to ever really get soft after he came the first time. “Guess I know my duty!”
Since neither of us felt the urgency that we had earlier I took my time, teasing his thick meat as we talked. Over the next hour or so I would lick or suck on him as the desire arose and he would tell me what he liked. I experimented on his dick with hands, lips, and tongue and at his urging took a turn at sucking his balls, which he liked and I didn’t mind. He called it ‘blow-job practice’ and told me I would have to show up for every scheduled practice if I was ever going to make it as a full-time cocksucker. I vowed to never even be late and Todd laughingly told me that if there was ever an Olympic cock sucking team that I could represent my country proudly. Finally the need in both of us became too great and I began to seriously suck my man’s hard cock.
I loved his dick with my mouth for a long time, or so it seemed. He had amazing resilience, as I would come to learn. It happened as he was leaning forward to cup my face in his loving hands; guiding me up and down his shaft as I face fucked his glorious cock. One second he was thick and rigid against my tongue and the next he was grunting and coating my mouth with another load of hot seed. I came rubbing my crotch against his leg as I sucked and fingered myself off again after he fell asleep.
Things were finally beginning to make sense.
Chapter 21
My boss at the convenient store accepted my change of clothing with no problem but was concerned about some of his customers who might not be so accepting. He was a bright guy, however, and soon had the answer by arranging a transfer for me to another store across town that was owned by the same chain. My new name tag read ‘Megan’ and I proudly wore it to my new job while Lou, my old boss, kept my paychecks, which still read ‘Mark’, coming to his store. I quit my job at the restaurant and my job cleaning houses became fun as I worked alone in empty homes and now wore my far more comfortable clothes. Once in a while someone would come home and surprise me but no one seemed to suspect my secret. A couple of the men even flirted with me and offered me ‘jobs’ babysitting. I declined because I knew what they really wanted me to sit on.
I thought my classes would be difficult to manage. It was too late to change my schedule and people knew me as Mark. My visit to Dr. Phelps helped in that regard. He arranged for me to take my finals in his office and even got me extra credit for participating in the study. He also arranged for my appointments with a local psychiatrist as required by Dr. Josten. His secretary even booked my travel arrangements for my trip to California.
Home time was domestic bliss for me. We decided that my cocksucking practice was to be ‘scheduled’ for the first time I saw Todd every afternoon. So as soon as Todd walked in the door, I had his dick in my mouth. Naturally he enjoyed my attention but I swear I loved doing it even more. So enthusiastic was I that sometimes I would be busily slurping away when I realized that the front door was still open. Once I looked up to find a neighbor lady watching me, the look on her face a mixture of disgust and envy. I smiled around my mouthful of cock and waved, guiding Todd a step or two further into our apartment so I could close the door.
That first blowjob of the day was wonderful, but it couldn’t compare with the second. Todd invariably came quickly the first time, usually no more than ten minutes after my tongue made first contact. The second time he could go for hours, so we saved that one for after we went to bed or at least until after supper. I would pile blankets in the hole in my couch and lay atop them so I could casually lick and suck him as we watched TV. I learned to keep him rampant for long periods of time but figured out how to make him cum when I was ready for a taste. I was in complete control of his orgasms and he knew it. More often than not I awoke him sucking on his ‘morning wood’ as well but I considered those as part of the previous day’s count.
Todd had made me a promise that he would make a woman out of me by one day fucking my ‘pussy’ with his cock. To that end he bought me some presents; to be precise he bought a bunch of dildos. There were six in the box and they ranged in size from the size of my pinky to one nearly as big as Todd’s manhood. They were labeled with some male porn star’s name and huge letters proclaimed it as his ‘training kit’. It came with multiple tubes of KY jelly and Todd bought me a copy of the latest Club magazine for ‘inspiration’. Club has at least one pictorial in every issue that show a man with one or more women and these men were always well endowed and wonderfully erect. I was terribly embarrassed but didn’t throw any of it away.
It was sad when I had to leave Todd to go to California but since he had spring practice and it was my first time on an airplane I managed to cope. I still cried. Luckily I got a window seat but the guy in the next seat was a fat salesman who kept trying to peak up my skirt or down my blouse. Walking through the airport in LA someone slipped a hand up my skirt and got a good solid grope of my left butt cheek. He received a solid slap to the shoulder, the highest on him I could reach, but he didn’t seem to mind the exchange at all. A middle aged woman led me into a ladies room to help me stop crying and advised me that the next time something like that happened I should ‘aim a little lower’. She soon had me laughing.
My contact at the LA airport was a stunning young man named Drew. He was waiting by baggage claim with “Megan Priddy” written on a piece of cardboard. Drew was almost as pretty as my Todd and I flirted outrageously with him as he carried my luggage to his car. He held doors for me and treated me like a lady and I was so turned on I considered using him for ‘practice’. I let my skirt ride up a little higher than I should have, and when I leaned over I didn’t bother to conceal his view down my cleavage, so I think I did return his kindness in some ways. He was a graduate student in Dr. Josten’s study so he knew what kind of girl I was. Drew saw me to my hotel and promised to pick me up in the morning for my appointment with Dr. Josten. Almost I asked him to stay with me. Almost. But I couldn’t cheat on Todd. I was glad I brought two of my smaller dildos. They received a serious workout that week.
Chapter 22
I met Dr. Josten briefly but mostly I spent my time with various under graduates helping with his study. They were studying my genetic disorder but they were really concerned with how that disorder affected people in the development of their personalities. Not all of us became ‘girly’, for example and most did not at some point decide that they were gay. Or so I learned later. I was examined physically and took a battery of psychological tests exploring my thoughts, dreams, as well as a complete examination of my childhood. They asked everything! I was so embarrassed.
Drew drove me back and forth from my hotel and took me to dinner twice. He was so sweet I had a terrible time not giving in to the urge to practice on him. He let me know early on that he was interested in me too. My plane left on Saturday evening and my testing was done on Friday so he took me to the beach. It was my first time seeing the ocean and I had to buy a bikini but it was fantastic. Yes, I allowed Drew to rub sun block on me. He did a great job. Of course I felt compelled to return the favor. That was one very attractive man.
The best thing that came from the trip was the fact that they put me on female hormones for the duration of the study; which was scheduled for three years! I had to make weekly visits to the psychiatrist back home and fill out weekly questionnaires about my feelings and thought patterns, and then return to UCLA every one weekend a month for further physical testing. Free hormones and trips to California! All that and I was being paid too! They even helped me get a California ID in Megan’s name.
Todd met me at the airport and we immediately found a secluded place to practice. God I missed his hard dick so much! His initial needs satisfied we returned home to spend a long night in one another’s arms. I sucked his cock for hours and completely satisfied my man. There was no morning wood in evidence that next day… darn it.
But the best of times can’t last forever, and that next day two things happened to depress my joy. The first was a letter from a lawyer explaining that my uncle had died. That was bad; I wasn’t close to him but he was my only living family. He’d represented a connection to my mom that I would never have again. He was also my only connection to my home and the place that I grew up. The second depressing thing happened as I was tearfully cleaning up the mess Todd had made while I was gone; underneath our bed I found a pair of panties… and they weren’t mine.
Chapter 23
No, he didn’t deny it and seemed surprised that I was upset.
“Megan I love being your boyfriend and you suck cock like no body else but I’m still going to fuck other girls,” he said.
I was devastated but eventually had to accept his feelings. He’d never said that we were exclusive and I honestly never thought that we were, but it’s different when you see the evidence for yourself. He did promise not to bring them back to our place, even when I wasn’t there, and I was grateful for that.
We went back home for my uncle’s funeral. Todd drove so I didn’t have to ride the bus. It’s only a four hour drive but I didn’t get to suck his cock even once as I was pretending to be Mark and Todd thought being sucked off by a guy would be ‘creepy’. It’s not like I looked like a guy; I was wearing panties and a bra and girl’s jeans. I had to buy a really big sweatshirt to conceal my breasts and not wear makeup but it was still me in the mirror even with my hair in a ‘boy’s’ ponytail. I didn’t want to make him uncomfortable so I didn’t force the issue. I stayed in the town’s only motel while he slept at his parent’s house. I knew better than to let anyone who knew me have unnecessary opportunities to really look at me. My new lifestyle had changed me physically and in my mannerisms. Personally I didn’t care who saw me as Megan anymore but I didn’t want to cause any trouble for Todd. I probably wouldn’t ever come back here again but he would.
The funeral was sad but I didn’t cry. I held my tears until I was alone. A lot of people came to see my uncle at the viewing but hardly anyone came to the funeral itself. I stayed there a few days after, signing papers authorizing my uncle’s lawyer friend to liquidize all the assets as I was the only heir. They would send me a check for whatever was left after his house sold. When Todd came to pick me up for the drive back it was Megan who got in the car. Mark was never seen again.
Chapter 24
Todd stayed with me for another few weeks but had to move back home for the summer to help his father with the family business. I loved him at every opportunity, hoping against hope that I could so satisfy his desires that he wouldn’t even look at another woman while he was gone. I knew better but it was a sweet dream. Almost every weekend he would drive back down to see me and we would have a glorious homecoming. His birthday was on one such weekend and I had one special present ready for him; my virginity.
We made a day of it and I wore my wedding dress for him as we pretended to be married. Then he carried me into the bedroom for the honeymoon. It was wonderful, even before we made love. I had been diligent with my dildos and the largest one, while still a challenge, no longer seemed so frightening. I lubed myself up and slobbered all over his cock before presenting myself to him. He was a gentle lover and took his time working his manhood inside my ass. He took me the first time in the missionary position, which I wanted as it seems to me to be the most ‘girly’. Todd insisted that I keep my panties on; he doesn’t like seeing my little dick, but had no problem hooking them aside in order to penetrate me.
The feel of his erection sliding up into me was magnificent; as was the feeling of his body weight atop my own. I felt like a complete woman as I lay on my back, legs spread wide with him on top of me and his hardness deep inside; my stiff nipples being teased by the hair on his chest. It took him a long time to fully penetrate me but he was careful to keep himself lubed up and when he held still for me to adjust he would occupy himself sucking my nipples or kissing me long and deep. I came during one of these ‘timeouts’ but not like I did later after I told him that I was ready to be fucked.
He did not disappoint. Pulling his enormous dick out until only the very tip remained inside me he would then slide back in the full length, not pausing until his balls were against my ass crack. Then he’d rest a heartbeat or two before repeating his actions. I nearly lost my mind at the pleasure when he completed those wonderful down strokes. After a few minutes of that I was ready for more and urged him to fuck me faster and again he obliged, speeding up the timing of his thrusts even as I lifted my hips to help draw him in. Finally he stopped whispering for me to be quiet and set his mind to pounding my pussy. I gripped at him with my arms, legs, and pussy muscles as he drove himself into me again and again; showing me once and for all what a woman was made for. I screamed and I cried out in completion as orgasm after orgasm came and went. He fucked me for quite a while and after coming inside me he pulled out just long enough to flip me over onto my belly before driving his still hard cock back where it belonged, picking right back up with his frantic pace as he pounded me from behind. He manhandled me; lifting me up by my hips to get the angle he wanted as he took what he wanted from me; which was also, wonderfully, what I needed to give him.
His strokes remained long and forceful for a long, long time as his grunts, barely audible over my yelps and groans, grew deeper and rougher between gasps for breath. His last dozen strokes were accompanied by the pounding of someone on my front door and someone else shouting ‘shut that slut up’! I barely heard them over the howls I was making in the midst of my best orgasm of the night. After I had squeezed every last drop of semen from my lover Todd collapsed atop me.
Several minutes passed as we regained our breath. I recovered first and looked over my shoulder at the beautiful face of my satisfied boyfriend. His cock was only half-deflated and I could still feel it inside me.
“Todd? You know I’m going to want this every night now, don’t you?” I managed between gasps for air.
Smiling he gave one last push with his hips before replying. “Then you’re going to have to find another apartment,” he laughed.
Chapter 25
Can you imagine how sore I was the next day? I had taken off from work anticipating some ‘issues’ of that sort and I was very thankful that I had. I wouldn’t have traded it for anything. I knew that with practice the soreness would go away just as the soreness in my jaw had when I was learning to suck cock. Todd went home very happy as well. I found a note taped to my door demanding that I learn a ‘sense of dignity’ and have some compassion on my neighbors. I think they’re just jealous. Sometime in the middle of that week I had a visitor.
I was wearing some ancient petal pushers and a shapeless smock as I cleaned my apartment when someone knocked. I opened the door to find a beautiful blonde woman with perfect teeth, flawless skin, and breasts that were trying to explode from her tight top. Her legs seemed to be longer than I was tall, an exaggeration of course, and her skirt was so short I could have probably told you how close she had shaved that morning. I had never seen a more beautiful woman in my life, not even in magazines or in a movie. She smiled sweetly, in as fake a smile as you can imagine, and introduced herself as Amanda. I gave my name and assured her that I was glad to meet her. She laughed.
“I doubt that, sweetie. I have a message for you that you’re not going to like,” she said, looking at me as if I was a bug crawling up her leg. I didn’t invite her in.
“We have someone in common; his name is Todd. I know he uses you for easy sex but those days are ending soon. Todd and I will be exclusive very shortly.”
My heart was pounding as I fought the rage and embarrassment that rose up. This woman was physical perfection; the kind of woman I would have fantasized about as a boy and dreamed of being as a woman. Tall, thin, and with a body that had all the right bulges in all the right places. This divine creature didn’t have to worry about her boyfriend urging her to keep her panties on to conceal her miniature dick; she could have any man she wanted with a smile. She was everything I wanted to be and I felt like nothing more than a skinny little boy in my raggedy homeless-shelter clothes. But she had also made me mad.
“That’s odd,” I opined, my eyes wide with innocence. “He just spent the whole weekend with me and never mentioned you once,” I stated, then slammed the door in her face. I didn’t cry until she left, which she didn’t do for some time. I ignored her knocks and hid my face under my pillow. Once she was gone I cried hysterically. Just before dark I cycled down to a pay phone and called him.
“Megan you know I see other women,” Todd said, as if that was all the defense he needed. “I’m not exclusive with her or you,” he explained patiently. “If she’s bothering you, I’ll dump her next time I’m in town, but I can’t be tied down to just one woman.”
I knew all of this but I was still stunned to hear him say it. I made a lot of crazy demands and asked silly questions and spent half my week’s salary on the call. Todd explained that while he had been with lots of women since I’d become his girlfriend that I was the closest thing to a steady he’d ever had.
“Other women come and go, but you’re the one I never leave. You’re the only girl I’ve ever stayed with,” he finished. “You are the only person I’ve ever cared about but I can’t see us being together forever. Someday I’m going to want children.”
We talked for almost three hours but that’s the gist of the conversation. He made me feel wonderful, telling me he loved me and that despite all of his other conquests I was the only girl he ever came back to. Then he tore it all down with that last part. I looked like a woman to him and felt like a woman, and represented an eager and willing mouth and, now, pussy for him to cum in but long term I was nothing more than a temporary place to put his dick. I’d do until he found the mother of his children. He hadn’t even gotten mad when I said that perhaps I would find other boyfriends, and I think that hurt me the most.
I woke the neighbors that night too, but it was from crying. Only one person knocked on my door, and it was my neighbor lady whose name I never did learn. She simply handed me a box of tissues and patted my cheek.
“Men will do that to you, honey,” she said, and then walked away.
Chapter 26
Todd’s visit the next weekend was subdued. He still rocked my world with multiple orgasms and I returned the favor by coaxing every possible load of cum from his sweet cock but he could tell that I was sad. I made sure he didn’t have a moment of rest where he could sneak away to visit that bitch Amanda. If he even looked towards the door I mounted him. He left more than satisfied. I was worried though because the next weekend I was going back to California, and he’d be free to fuck her. I knew I couldn’t compete with her.
My flight was uneventful though one of my small suitcases was lost somewhere. I had dressed very flirty in a short floral print dress that showed off my breasts to best advantage. Drew picked me up at the airport and I immediately began flirting. Who am I kidding? I was hitting on him from the first moment I saw him. His hand slid from its guiding point in the middle of my back down to the top of my butt and I just slid right up into him as we walked. After he put my surviving suitcase in the trunk of his car he held me in his arms and gave me a long, sweet kiss. It was nice. Not Todd-level nice but exciting nonetheless. It felt good to know that there was more than one man who found me attractive.
Drew tried to leave after he dropped my suitcase onto the bed in my motel. Silly boy. I told him I needed another kiss and he gladly complied. I had his shirt off quickly and guided him onto his back on the bed, never releasing my liplock as I lay atop him. My trip was definitely getting better.
He was muscular; though not as bulky as Todd he was active and fit. I enjoyed kissing my way down his chest and stomach, grinding into his hard dick as I did so with whatever part of my body was against him at the moment. His jeans were difficult to unfasten but I persevered, licking every bit of skin I uncovered.
Briefs, not boxers. I pulled them down with my teeth.
Drew was well-hung and had nothing to be ashamed of. He didn’t match Todd for girth or width but it was a beautiful piece of meat and when hard stuck straight out from his body with a slight upward curve. I immediately began licking up and down it, getting it wet enough for the deep-throating to come. It was wonderfully hard and my soft lips soon had him making dry thrusts upward as he begged me to suck him. I couldn’t deny him very long and gladly slid my face down his length, glorying in the taste of his cock as I slid my lips up and down, slurping and sucking as I urged him to completion.
To my surprise he didn’t just lay back and enjoy my attentions, he used his hands to urge me to spin around, working us into a 69 position. Once he had his face under my dress he embarrassed me by sliding my panties aside and licking on my barely stiff little clit. I wasn’t expecting that. My reservations soon disappeared as he returned my sucking, pulling my weak little cocklet into as close to an erection as I had experienced in months. It felt so good I lost track of what I was doing and paused with about half his length in my mouth, my tongue quivering against his head as I sat with eyes closed and my approaching orgasm on my mind. Once I had came I finished him off with a flourish and discovered that Drew’s cum tasted better than Todd’s ever had. His was less ‘musky’, perhaps. I’d read that diet played a part the taste of one’s cum, so perhaps that was it. Drew took a little while to recover but I adored spooning with him before we fucked. He was kind and gentle and we had a great weekend together.
My examinations went well, though the person who counseled me was surprised at my breast development.
“You’re a very petite young lady,” she explained. “So I’m surprised to see your breasts developing so rapidly, particularly when your mother was not a large-breasted woman.”
Obviously I had no real answers to that. “How much larger do you think they might get?”
Thoughtfully staring at my charts she replied, “Well a C cup is certain and you might even reach a D. For your sake I hope not; you’re tiny body just wouldn’t be able to support them.”
I was really excited to know that! C cup! Who would have thought even two years ago that I had C cup titties in my future? And now we were discussing possibly D’s? I was ecstatic! Let’s see little miss perfect Amanda show my Todd some D cups!
Of course, that thought made me sad. No doubt Todd was fucking Amanda, or someone else like her, right that moment. My guilt over sleeping with Drew wasn’t too strong; Todd had made it very clear that we weren’t exclusive, but it was still there. Jealousy was tearing me up inside, thinking of Todd’s glorious cock being sucked by that bitch; or worse, her getting to feel it pounded up into her pussy; something I would never be able to truly accomplish.
Drew, which I found out was short for Andrew but he detested Andy, took me to the beach so I had a second chance to wear my bikini. The water had been too cold to wade in last time but this time I got wet, which turned out to be a mistake as my white bikini top became see-through and I didn’t realize it right away. I wondered why the guys on the beach were all smiling at me so happily. At least I got to work on my tan and Drew was again standing ready to rub lotion all over me. He even rubbed it on a few spots that weren’t going to be seeing any sun but he said that he wanted to be thorough. Don’t worry; I repaid his kindness when we got back to my hotel. He fucked me once standing up in the shower; that was something new. Todd and I had taken showers together but I always wore panties or a swimsuit bottom to conceal my little dick. I had always enjoyed sucking him with the warm water running over me but Drew made that whole experience extra special.
We went to dinner together and made out through an entire movie; I don’t know what we were watching as I had eyes only for him. I warmed up his cock with my mouth as we drove home and he fucked me leaning over the desk just inside the door to my room. He didn’t share Todd’s stamina but he was enthusiastic and, of course, paid a lot more attention to my needs. He was a very, very sweet guy.
I returned home to find a note from Todd, telling me that he missed me and couldn’t wait until he came up next weekend. That made me happy, yes, but also depressed me as I knew he’d been fucking Amanda in my apartment while I was gone. I checked the bed to find that the sheets had been changed but, sure enough, found a pair of her panties lodged well up in one corner. She couldn’t miss the chance to tell me she’d been there. I spent most of that week, when I wasn’t working, plotting my revenge against her. I found her address in the campus phone book but by Friday night I was so deeply missing my boyfriend that I had quite forgotten my jealousy of her when Todd finally came home.
Jumping into his arms I had forgiven him everything halfway through that first heart-pounding kiss of pure animal lust. I had my arms and legs wrapped around him like vises and made sure he was breathless before I let him up for air. After kicking the door shut he took me to the bed and ravaged my breasts for a long time, making both nipples so stiff with need it was a wonder they didn’t bore through his chest when he finally mounted me. Drew made me feel like a lady. Todd made me feel like a woman in heat. At that moment in my life I couldn’t have told you which I liked better.
Chapter 27
The school had renovated an old dorm for the football team so Todd would be moving out before the fall semester, which naturally depressed me. I hadn’t even enrolled yet as I wasn’t sure how to accomplish it as Megan and I had no desire to do so as Mark. I spent every second with Todd that I could and kept him with me in our apartment as much as possible. I didn’t ever want him to leave. My monthly trip to California became weekend-long fuck-fests with Drew and I marveled at the differences between the two men. I truly loved them both, just in different ways. Neither ever asked about my life outside of the time I spent with them.
I was regularly seeing a psychiatrist now who was supposed to be exploring my gender-identity issues. Mostly we talked about my relationship with Todd. She said that he was just using me and I explained that I understood that, but that he had given me so much that I wanted him to continue using me and me alone! Without him I wouldn’t be the woman I am today. He was the first person to ever accept me as Megan and did so before I had even accepted it myself. Every single bit of joy and happiness I had experienced since I was a teenager, including the fun I had with Drew, were directly connected to Todd! How could I not love him?
I knew that she didn’t understand, not completely, but she didn’t judge me. She made her regular reports for Dr. Josten’s study and often congratulated me for avoiding the mental anguish so many trans-gendered and crossdressing people suffered as they tried to find themselves. That was another thing I had Todd to thank for.
A new routine developed for Todd and myself. Once he moved out and classes began, with, of course, football games starting up again, I didn’t see him as often as I would have liked… which was every second. He would still come over when he could, sometimes showing up in the middle of the night just to fuck me and then leave. Other times he would stagger in drunk and ask me to suck him off before falling asleep sitting on my couch. He never stayed the night, as the football coach had a curfew for his players during the season, but he showed up at really odd times which told me he wasn’t really obeying that curfew or was sneaking back out after check in.
I saw his car at Amanda’s a lot, but knew that he was also dating another girl named Carrie whose father had a lot of money. I began to notice that on nights I didn’t see his car at Amanda’s that I would see him later at my apartment. Now I understand what was going on but then I couldn’t see it; Carrie didn’t put out but Amanda did, so on the nights he dated Carrie he would come to me later to ease the pain in his blue balls. I was more than willing, even grateful, for the opportunity to do that. Even when he only came over for an hour I was thrilled just to be with him. He was my whole world, outside of work and my one weekend a month with Drew.
I went to all the home football games to cheer for my infrequent boyfriend but spent more time exchanging glares with Amanda then I did watching him play. Todd never did miss a game waving to me and seemed to spend more attention on me than he did Amanda but he didn’t just ignore her completely, which drove me nuts. I tried to dress nicer and nicer each game to show her up but she always outdid me. Her clothes were better and her body better built; I had no chance. Todd waved away my tears.
“I spend more time with you and enjoy being with you a lot more than her,” he would say, dropping a panty peeler on me and then kissing me softly. “She’s hot and the sex is great but you’re the one I always come back to.” That was his new mantra; I was the one he always came back to. I just wish he wouldn’t leave so he wouldn’t have to come back to me. I came to understand that he did care for me but I was more of a convenience, like an old comfortable shoe, than someone he couldn’t live without. No matter what went wrong he knew that I’d eagerly welcome him back with open arms, and spread legs, whenever he needed me. I was his new Gina, though I think that he cared more for me more than he had for her. I hoped so anyway. By Thanksgiving it wasn’t enough anymore.
Chapter 28
It was early November when I went back to California. Drew picked me up as usual but he wasn’t alone; he had a little tramp named Toni with him. Toni was his new girlfriend and they were exclusive. I guess he wanted her along so that I wouldn’t rape him. Toni was an ugly little drudge with hair extensions and no boobs; what could he have ever seen in her? She was also in the same study as me but lived only a few blocks from Drew. She claimed to be ‘pre-op’ and to have been on hormones for years but she looked like nothing but a boy in a dress. She liked wearing low-cut tops but had razor stubble on her chest! Razor stubble!
Things weren’t any better when I returned home. I caught an earlier flight and reached my apartment a couple of hours before I should have and surprised Todd fucking Amanda. They were going at it like the world was ending and he was hammering away at her snatch like an engine. They never even heard me come in and I got a good view of his piston-like ass drilling away between her spread legs as she grunted away beneath him. Something just died inside me. I left without their even knowing I’d been there. When I returned later Todd was there to welcome me home, kissing me and grinding his hard cock into me as he hugged me fiercely.
“I missed you so much,” he growled, guiding my hand to the bulge in his pants. “I need you now.”
Hating myself all the while I still sucked his dick. He came over Friday night, no game that week, and we had a small Thanksgiving dinner together. I told him that it was over for us and explained what I had witnessed. He was sad, he even cried, but was so very sweet and understanding that it broke down all my fortifications and left me sobbing in his arms. We made long, slow love that night as we knew it was going to be the last time.
I quit my jobs that next week and closed out my lease. Dr. Josten’s office arranged for me to get an apartment in LA and I was enrolled at UCLA for the spring semester… as Megan. They were very helpful and even helped me to get my name legally changed. The move itself was easy as most of my stuff was easily disposed of, we burned the couch in the back yard, and after purging my clothes of any remaining icky-boy things and most of my early girl things I shipped my surviving clothes to my new home.
Todd was supportive about the whole thing and gave me a ride to the airport. He brought Amanda along and as a farewell gift gave me the most passionate kiss and grope I’d ever experienced outside my apartment. People were staring at us! The jealousy on Amanda’s face was exquisite and I whispered my thanks in Todd’s ear as he all but dry-humped me against a wall. He could be so sweet.
He made it even better as I boarded the plane, waving to me and, right there in front of Amanda, called out, “I’ll always love you Hillbilly girl!”
I thought Amanda was going to go into convulsions right there.
I don’t think I needed the plane to fly that day.
Chapter 29
So that’s my life story, but it’s only the beginning. I’m here in my new LA apartment looking at some brochures Drew gave me when he dropped me off… with Toni along of course, making sure I didn’t sneak in a grope somewhere along the line I guess. The brochures are on Sexual Reassignment Surgery and something I’m seriously considering now that I have the money from my uncle’s estate.
I don’t know what the future will bring but right now I’m sitting on my new terrace, watching the shirtless pool-boy cleaning the pool. He’s tanned dark from the sun and his little Speedos are doing nothing to conceal the distinct bulge in his crotch that has grown since he first noticed me in my tiny, floss-like bikini. I’ll start looking for work tomorrow but as for today, perhaps some sun bathing is in order. Maybe I’ll ask that delicious young man if he can spare some time from netting leaves out of the pool to rub some sun-tan lotion on my nearly naked body. Perhaps I’ll reward him for his faithful service with a breathtaking blowjob.
After all; we Hillbilly girls need to keep in practice.
Hello, my name is Teresa and I would like to share a little fantasy with you. Most of it is true, the rest is imagination. I’ll leave it to you to decide which is which; I know that’s my preference when I’m reading stories such as this one.
I’m not very big, nor overly masculine. I love dressing up in women’s clothing and have a variety of wicked fantasies I indulge in when hiding within the sanctity of my home. Many of them involve me being made love to by a man, and I am particularly fond of being a cheerleader when I seduce my current imaginary stud. However in my fantasies I am either a real woman or so passable that the hot man of my current dreams has no idea that it’s not a woman sucking his cock. I love the fantasy of being caught dressed like a woman but not being forced into doing anything as a result of it. When I kneel before my man I want him to know it is absolutely voluntary.
So normally I dress at home and have only rarely ventured out into public. A few times I have dressed up, hidden everything under a long coat, and went out to rent a video or something. Once when I lived in the country I went outside totally dressed and drove my car in about a five mile circle right back to my own house. I love the thought of being caught, but not so much that I actually want to be caught. I’m not prepared for those repercussions. Therefore I live a somewhat lonely life, but I really don’t mind.
Physically I am very fit, and work hard to keep myself as thin as possible. It helps me feel pretty when I dress up. Nature, combined with specific weight training and endless aerobics, have given me natural A cup breasts and wide hips although I normally augment my chest with breast forms to a C when I want to feel sexy. If I just want to dress casually I’ll wear my smaller bras without the forms. My hair is long but I often prefer wigs to my natural mousy brown. Occasionally I take a weekend and concentrate totally on feminizing myself, and I must say that when I take care with my makeup I am almost passable, at least to myself. I am too big a coward to ever take a chance that someone might ‘make’ me, so I don’t know for sure how well I do it. At least I didn’t know until recently.
I work in a large factory, and I do mean large. Our company does business with a variety of industries including the automotive. We have extensive assembly lines and manufacturing areas and at any time have millions of dollars of inventory on hand. Keeping track of all that inventory is difficult, and so our company created a small department of six people whose sole purpose was to count something every day, correcting any errors found but ensuring that the quantities of parts shown in the computer were, if not accurate, at least pretty close. It’s not a hard job but it can be awfully boring.
As the member of the Inventory Department with the least seniority, I often get stuck with the worst possible assignments but as even the worst assignment in Inventory is better than the best assignment on one of the assembly lines, so I don’t complain. At least I’m on day shift.
As you can imagine there aren’t many days that there isn’t something going on somewhere in the plant. I once worked on Easter Sunday. Even if every bit of production is shut down, there are likely to be Maintenance men or contractors working on something. Those days are primetime for the Inventory Department, as we can inventory items that might otherwise move too quickly for us to keep up with, so you can count on our department being ordered to count something any time that production is shut down for any reason.
I joined the department last February and as each holiday approached and we found out what parts we had to count it became quite clear to me that none my higher seniority coworkers were going to volunteer to work for even one of them. I resigned myself to working every holiday for the next several years.
At first I was appalled when told that I would be working both Christmas Eve and Christmas, but a few words with Ike, the guy who was the lowest senior person in the department before I arrived, assured me that it wasn’t so bad. He explained that last Christmas Eve he had been alone in the plant except for a handful of contractors, and completely alone all day on Christmas so he had hurried through his few duties and spent the day surfing the web and sleeping. Not bad work for double-time and a half. He explained to me that I could even come in on third shift if I wanted to, so that I could have my holiday-days free. I mulled this over for a few days and decided that perhaps working those days wouldn’t be so bad after all.
I did some investigating and found out that there would indeed be some contractors in the plant on Christmas Eve, but only during the morning hours. No one was going to be in the building on Christmas except me. My devious mind began planning some fantasy activities for me.
Arranging to work third shift on one day and second another was as easy as Ike had said it would be. The plant would be deserted starting at 11am Christmas Eve and I didn’t have to clock in until noon. Then I was off from 8pm until Midnight, when I would clock in again. It might seem like a tough schedule but those hours gave me the maximum amount of time alone in the factory while limiting any chance that someone might show up for some reason. There was always some suck-up foreman coming in to check on something during the day, but with those hours I would be safe, I hoped. Being the natural coward that I am I still couldn’t convince myself of that completely.
Preparations for my upcoming fantasy began two weeks in advance. I knew that I wouldn’t completely go through with everything I had planned, but getting everything ready was so much fun. In my dreams I went to work in a dress and high heels, and I packed my oversized lunch box with a variety of fun things to do when I got there. The reality was far less, of course, as I couldn’t take the chance of being caught. If nothing else I could be fired for not coming to work wearing the baggy blue work uniforms we were assigned, not to mention the steel-toed work boots that had to be worn even by the people who never left the office. Still, I felt myself quite daring when I left the house wearing what I did.
I spent Christmas Eve morning napping, shaving, and nare-ing myself to complete smoothness. I wore a nightgown all morning, just to get myself in the proper mood. I knew that if I was not really horny when I left for work, I’d chicken out and not go through with my ultimate plan. When the time came to get dressed, I naturally didn’t follow through completely, but I packed as if I was.
First off was my underwear. Pink satin panties with a cute little flower on the front went on first, completely and easily disguising my tiny dick even when erect. I groaned at the feeling of wearing my panties, I dearly love them. Next I slid my stockings up my long, smooth legs, then slipped my waist-cinching girdle on and fastened the snaps to my stockings. I was already nearly too excited by this time. I knew that I would go no further with my clothing, but teased myself by putting on the matching bra for the panties, knowing that I would chicken out and remove it before I left the house. It was one of my A cup ones, and I loved how delicious it felt as it caressed my breasts. Next I donned my hated uniform, ignoring the dress I had laid out. I knew I couldn’t wear it or the high heels but wanted to enjoy the illusion as long as possible.
Finally I packed my lunchbox as if I was going further with my little fantasy, including my breast forms, a size C bra that also matched my panties, a wig, and a satin top slip went into my purse, which also contained my makeup. I even added my dildo, doubting that I would dare take it out but loved the thought of peeking in at it. I slipped my purse into my lunchbox and was almost out the door when I remember that I was still wearing my bra. That was when I exceeded my expectations, as I dared leave it on for the drive to work.
My confidence was sufficiently buoyed by the sight of the deserted parking lot that I even dared to wear the bra into the plant. I knew my uniform would conceal most of my girlish underwear, even the slight bumps from my little A cups, but also knew that if I stretched the wrong way my bra straps would be clearly outlined on the back of my shirt. I swallowed my pounding heart and entered the building, glad of the concealment of my jacket even as I kept my arms crossed over my chest. I just knew someone would be there.
A quick search of the offices revealed no hidden person, as did my survey of the nearby shop floor. I was so glad we didn’t have any security people, for whatever reason our plant didn’t have any, or camera’s. We depended solely on a sophisticated alarm system that I of course knew the password too. I checked the secondary parking lot, then the primary one again, seeing only my rusty little Volvo. I was truly alone.
At this point I realized that my bladder was about to explode. I had been so intent on searching for hidden spies that I had neglected it. I entered the locker room with the intention of peeing and then using one of the lockers to lock up my lunchbox, as I normally do, when I suddenly remembered what I was wearing. Hands shaking, I removed my purse from the lunchbox and slipped it over my arm. Peeking down the hallway in both directions I dashed breathlessly across the way, sliding into the women’s locker room without really opening the door.
“Anyone here?” I squeaked, the pounding of my heart so loud I doubt I would have heard any reply that might have been given. I quickly peed in the closest stall and dashed back across to the men’s locker room as if a monster was on my heels. There I reclaimed my lunchbox, deciding that I wanted everything to stay with me, replacing my purse within it, and nearly ran back to the front of the building to recheck the parking lot.
I was still alone, and began to be concerned with having a heart attack as it pounded away beneath my pretty bra. I was so frightened, and so excited!
Walking back to the Inventory office normally takes no more than five minutes. I took the longest possible way, doubling that time, so that I could inspect as much of the plant as possible for habitation. I still saw no one, but couldn’t seem to calm my racing heart. It just felt so good to be wearing my feminine underwear, how I wished I dared wear them all the time. I just couldn’t face being found out.
I reached the Inventory office, a former large closet that had been given over to our use when office space elsewhere became scarce, and closed the door behind me, loving the feel of my bra stretched across my chest as I sucked air through my wide open mouth. I snaked my way between the tightly situated desks to my little cubicle, and immediately sat down to try and compose myself.
Which took some time. I fired up my computer and checked my email messages, gratified that the work due that day was not overly time-consuming, Ike had helped me get as much of it done as possible in advance, and that nothing new had been added. Grabbing my clipboard I prepared to go begin my first count, and then made the first of a series of fateful decisions that day. Telling myself that no one was here but me, I unbuttoned the top two buttons of my shirt.
Now I knew that even with those buttons open, no one who might show up was going to see my bra unless I pulled my shirt open for them. Still it was quite a thrill for me to be able to so easily peek inside and see the lacy edges of my bra, and the hint of miniature cleavage I was pleased to have. Next I secured my long hair behind me with a rubber band in what I considered a masculine way and then, clutching my clipboard over my breasts, I fearfully opened the door.
Again I saw no one, despite returning to both parking lots to be sure. I trembled as I held the clipboard over my breasts, my pulse pounding behind my eyes as I shakily began counting my inventory. After about twenty minutes I relaxed enough to lower my clipboard, and after an hour I calmed down enough to even open another button. Anyone approaching me now would easily see my bra but I was now brave enough to believe that no one was coming in and even if they did, I would see them coming and have more than enough time to fasten one button.
Break time arrived as I finished my first count. I clutched the clipboard to my chest; now pretending it was my homework as I walked home from school rather than trying to hide my chest from anyone’s view. I practiced my feminine walk, placing one foot directly in front of the other as I strutted my way across the plant. I felt so good, so sexy. So feminine.
I sat in one of the breakrooms, drinking a diet coke and skimming through an old newspaper someone had left there. After using the ladies room again, I strutted back out onto the plant floor and began a different set of counts, all the while wondering if I was going to have to masturbate in order to make a good count. As time went on I became more and more relaxed in my situation, which of course caused my mind to begin searching my options.
Returning to my office I began my research, checking the inventory records against my counts. All the while I was staring at my computer screen, the corner of my mind was glued to my nearby lunchbox. I wanted more, more feminization, more thrill, and more excitement.
I ripped the top off of the lunchbox and tried to choose what to do. I still didn’t feel completely confident but knew I had to take the chance and push the envelope a little more. I considered the long black wig, but rejected it just as quickly. I considered my breast forms, and blushed at the mere thought of the dildo. Finally I slapped the top back on the lunchbox and settled on readjusting my hair, removing my ‘masculine’ tail and replacing it with a high ponytail. That felt pretty nice, bouncing around on the back of my head, yet I knew I could easily laugh off anyone who saw it, claiming that many men had pony tails. It only took a few moments before I realized that the ponytail just wasn’t going to be enough.
Taking my purse, leaving only the wig in my lunchbox, I peeked out the door of our little closet to make sure no one had wandered in. I then eased the door open and spent a few moments listening. Confident that no one was around I slung my purse over my shoulder and minced over to the ladies room, admiring the simple word as I slowly swung the door open. “Women” it said. So simple a word, and yet it thrilled me to no end to be able to open this door.
I made sure my shirt was open enough to give me a view of my bra peeking out of my shirt as I spent five wonderful minutes primping my hair in front of the mirror. I readjusted my pony tail, ensuring it looked as feminine as possible, secretly assuring myself that I could pull the rubber bands out quickly enough if need be. I gathered up my purse to leave when I had another thought the set my heart to pounding. Again with hands shaking, I am such a coward, I took out my lightest shade of lipstick and gave myself the thinnest coat possible. Eyes wide at my own courage and drunk with the eroticism of it all, I staggered back to my hidden cubicle licking my lips in near ecstasy.
Now I know that compared to some of you girls the things I was doing were not erotic or dangerous but to me that were both those things and more. No one knows about Teresa, no one. I have always been content with that outside my personal fantasies. What I risked that day was my entire life as I presently knew it, and I was nearly petrified with fear and arousal.
Once I had regained a little composure, I felt that stirring again. I knew I wanted to take this just a little bit further. Initially I resisted the impulse, contenting myself with working at my computer for over an hour. Finally I simply ran out of things to do, and my idle hands joined my idle mind in my desire. Grabbing my purse I returned to the ladies room, but this time I nearly went berserk.
My A cup bra went into the purse as quickly as I could get it off. My C cup replaced it, breast forms firmly attached with glue into place. Next I put on my slip, I dearly love slips, and regretfully put my ugly uniform back on over it, making sure that enough buttons were undone to leave no mystery as to what I wore beneath it. I was almost sick with fear, yet I took a good half hour fixing my makeup to perfection. No wanton slut here, just a girl trying to look her best. I replaced my usual clear nail polish with something a little more daring, wishing that I had my nail extensions along but I had forgotten them. I touched up my hair and nearly lost my nerve when it came time to leave the bathroom. There was no way I could explain any of this if I was caught now.
I must have looked like someone in fear for her life as I slunk from that bathroom. Unable to stand the suspense I went to the front of the building, slinking from hiding place to hiding place, until I could view both parking lots and assure myself once again that I was alone. Gasping with emotion when I saw that they were both empty of trespassers, I returned to my office for my clipboard and began counting those parts I was supposed to be counting on the next shift. I had to do something or I was just going to explode!
Time again eased my fears until I truly began to enjoy myself. I spun about, laughing and practicing my feminine voice, pretending all the while that this was just any old workday and I was just a girl doing her job. I found myself drifting by work areas were particularly good looking young men normally worked and found excuses to ‘accidentally’ bend over in front of them, showing off my ass or cleavage, pretending that they were enjoying the view as their cocks grew harder and harder. In real life I was only showing off for robots. Sigh. The thought of my dildo was getting tougher and tougher to resist.
After recounting my parts three times, I had a hard time keeping my mind on my job; I finally assured myself that I had a good, accurate count of what was on the production floor. I only needed to check the receiving warehouse for current stock to be done with my count. As it was well past lunchtime already, this was the last task I would do that day, saving my remaining paperwork for my shift later that night. I went to the warehouse door and entered the long building, emerging in the middle of the centermost aisle.
And there stood a man looking at me.
Not that he was anywhere close to me. He was at least a hundred yards away but he could see me just as clearly as I could see him; that is to say not very. Still I had just been seen clearly dressed as a woman for the first time in my life.
We were too far away to make out details, you say? I know better. I could see him and knew he was a guy wearing blue jeans and a yellow jacket. He was also wearing a hardhat, which meant that he was likely a contractor. I was so scared I know I squeaked in fright at the sight of him and then just stood there, stunned and likely with my mouth hanging open. He returned my stare with a smile, taking a step towards me and saying “Hi there.”
I ran away.
No, not really, but I didn’t stick around to wish him a pleasant evening. As quickly as I could escape I did so, darting back through the door into the main building. A glance over my shoulder showed me that he was still coming towards me, perhaps following me. I made sure to walk as femininely as possible, hoping to maintain my illusion since he wasn’t anywhere near me. What should I do? Where should I go? I needed to get my hair out of this ponytail, and get these breast forms off my chest, and get this makeup off! But what if I didn’t do it fast enough, and he caught me in mid transformation? He’d know I was a guy and would then tell my secret to whomever he knew in the factory. Would I be better off trying to pass myself off as a female? Could I pull it off? What if I did and he later asked for the girl he met working on Christmas Eve? I was the only employee here!
Nothing I thought of seemed to be the right answer, so I did what my inner voice said: Hide! If he never got close enough to see me clearly, he would either forget he saw me at all or confuse the details over time. “You saw a lady in here the other night? Naw, that was just Chad. He’s kinda small, and he’s got that long hippy hair, but he ain’t no girl. Yeah, I guess you were kind of far away, easy to understand.” That was my only hope.
But where? I started to head for the ladies room, but thought that he might wait outside if he saw me go in. Why shouldn’t he? If he was a local contractor, he likely knew a lot of people that worked in our factory, and may even think that he knew me. It was no accident that I looked somewhat like a pretty young lady that worked in the Human Resources Department. I’d switch bodies with her in a minute. She was often on my mind when I played dress up, as I truly admired how good she looked even in her company uniform. She was a primary source of emulation for me.
With the bathroom rejected I settled on the Inventory office. No one ever came there as it was out of the way, tucked into corner on the second floor of the payroll department, and at the end of a hallway that either went to our office or a room filled with generators. I could not remember the last time someone not from out department had even been in there. There I would be safe.
With the office door firmly closed behind me I leaned against the portal and trembled. It occurred to me that I had just ran out of options. If this mystery contractor did find me now I had only but two choices left to me. Since I had forgotten my purse in the bathroom, I could now either try and pretend to be a woman for real or beg him to keep my secret.
Eventually I calmed down. He wouldn’t find me here. No one ever came back here and this guy wouldn’t have any business with me. He had obviously surprised me and I had moved quickly away. He would think that I was afraid of being raped or something and likely leave as soon as possible. He wouldn’t come looking for me.
I sat with my head in my hands, slowly calming down. It was nearly 8pm and time for me to leave. I would wait until the last minute, then sneak out to retrieve my purse, change back into boring old Chad and then drive home like my life was in danger. I would come back at midnight in male clothing and I would from now on keep the panties and skirts in my bedroom.
The pulse pounding in my ears must have been why I didn’t hear him until he knocked on the door.
“Uh, excuse me Miss?” he asked, his voice muffled by the cheap wood.
Mortified I held my hand cupped over my mouth, so scared I dared not breath. Please let him go away.
“Uh, Miss?” he said again, obviously no great whiz at conversation. “Look, I’m sorry I frightened you but I have permission to be here.”
It was then I knew that he knew I was in here. I wasn’t going to fool him that way but if I could keep him outside the door, perhaps he would never know I wasn’t a real female.
“What do you want?” I squeaked, using my practiced female voice. It’s pretty good, and I was at least a little hopeful I could fool him with it, just so long as the door remained closed.
At the sound of my voice he opened the door.
“Hi, sorry again for scaring you. Someone should have told you I was coming by. I’m with Sanders Electric, and I was supposed to give this paperwork to Joe Clemons,” he said, waving a sheaf of paper. “He was supposed to meet me at his office.”
I spun my chair about, unwilling to give him a clear look at my face. I knew Joe, and his office was indeed back in the Receiving Warehouse. I also knew he was off work, having left early the day before when his wife went into labor.
“He’s not here,” I said, praying that he didn’t figure out my secret. So far he hadn’t given me any reason to believe he knew that I was a man.
“Maybe I could call him. Do you know his extension?”
I don’t know if my fright was making me a better actress or if he was simply preoccupied with something else but when I took a quick peek at him he was obviously unaware of who I really was, digging through a pocket organizer in search of Joe’s extension number. Rather than risk speaking again I snatched up the phone that sat on the table right next to him, bringing my hand uncomfortably close to his crotch as I did so, and dialed Joe’s in-house extension before handing the handset to the intruder. He accepted it gratefully, thanking me and again calling me ‘Miss’ to my inner delight.
As he waited for Joe to answer the phone, something I knew would not happen as Joe was certainly still at the hospital and unlikely to return to work just to meet a contractor, I was thankful that I had turned my name plate over upon my arrival that day and that I had chosen a uniform whose name tag had been ripped off. After a few futile rings he hung up, and asked me how to dial out so he could try Joe at home. My shaking little hand reached over and dialed the four-digit code necessary to make a local call, but my eyes were fixated on the bulge of his jeans just a couple of inches away from my pinky. I whispered a ‘There’ and went back to staring at my monitor, trying in vain to judge the man’s reactions by his reflection in my monitor. I pretended to type something, but I’m sure it was just gibberish.
“Damn,” he said, laying the phone back down. “He’s not home either. Oh well, I guess I could just leave it on his desk.”
I nodded, looking back just enough to give him a small smile before returning to my supposed work. I thought he would leave but he seemed to be waiting for something.
“Look, my name is Tom and I really am sorry I scared you a while ago. Joe told me that I could always find someone here in this office if he wasn’t here, but I truly thought that he’d let you know I was coming just in case.”
I assured him that it was all right, trying to be polite but not allowing him any opportunities to continue the conversation. Why wouldn’t he just leave?
He continued to talk, asking simple questions like my name, and how long had I been with the company and the like. I answered him as truthfully as I dared, with short one or two word answers such as ‘Teresa’ and ‘three years’, and then abruptly told him that I had to go, as it was time for me to get off work. That was certainly a mistake.
“Well let me walk you to your car at least,” he said, a shy smile just turning up the corners of his mouth.
Then I made my biggest mistake of the evening, I looked up into his eyes.
He was gorgeous! His blue eyes were perfect, as was the sweet little dimple in his chin. I found myself staring at his lips, wishing I was being kissed by them. With his jacket open and nothing underneath but a thin T-shirt, I could see that his body was lean and well muscled. I opened my mouth to thank him but graciously decline his offer but what came out was a grateful acceptance.
What was I doing?
He waited patiently as I shut down my computer and then sweetly held my jacket for me. I noticed him peeking down my shirt before I realized that I had forgotten to rebutton it when he entered the room. Not wanting to draw attention to my lacy slip I turned off the lights and led him across to the bathroom, explaining that I had left my purse there. He waited patiently for me as I took the opportunity to touch up my makeup and rebutton two of my buttons, one of which I unbuttoned again before I left.
We chatted as we left the plant with Tom doing most of the talking. We had to go out of our way to leave the papers on Joe’s desk but I found myself not minding the extra time with him. He was very polite and mannerly and I found myself enormously attracted to him. However the fear of discovery still loomed far too large for me to consider anything else. I had hoped to part ways with him at several different turnings necessary to leave the building but he seemed intent on walking me all the way to my car. This irritated me somewhat until I saw that his pickup truck was parked next to my Volvo.
A true gentleman he took my keys from me and unlocked my door, holding it open for me to slide behind the wheel. However he seemed in no real hurry to leave, and continued his small talk for some time. Eventually I stated that I had to leave and explained that I was due back to work in just a few more hours.
When will I learn what not to tell? This fact simply gave Tom more ammunition to talk about and I found myself enraptured with this sweet man. After an hour had passed he asked me if I’d like to go out for some coffee, as it was nearly nine thirty and I had already stated that I did not intend to go to sleep right away.
What was I to do? Obviously the guy wasn’t going to leave me alone and I was more and more sure that I didn’t want him to. I couldn’t take my eyes off of him and he was beginning to flirt with me! Was I fooling him? Did he really believe that I was a really and truly a girl? I’m not sure at what point that I made my decision, but I resolved that if this sweet, handsome man thought that I was a real woman, or just wanted to pretend that I was and treat me that way, I was going to go all-out to enjoy the experience.
I insisted on taking my car and getting takeout and so we spent the next two hours sitting at the lake, drinking lukewarm coffee and talking. He drove, naturally, as he was very sweet and a real gentleman. I’ve never laughed so much in my life! I found myself lost in his eyes a number of times, other times I found myself watching his sweet lips moving without a clue what words he was saying. I couldn’t imagine a more attractive, thoughtful person. Time was flying along and suddenly I found myself leaning towards him as he was leaning towards me. He was going to kiss me!
Odd how I didn’t think about that fact that I was kissing him too. I was totally into my female role at that point, and my handsome boyfriend was kissing me.
I sank into his sweet lips, going limp at the magnificent pleasure that was blazing through my body. This man was absolutely perfect, and he was kissing me, Teresa! I felt like I was finally a woman; an attractive, desirable woman! I’m not sure how long I experienced the heavenly pleasure of his lips. When I came to myself again he had reclined my seat and was leaning over me, our mouths attached as if life itself depended on the contact. One of my hands held him prisoner by the back of the head, and his hands were busy cupping my face and softly squeezing one of my breasts.
That was when I noticed the dashboard clock said 11:43.
We barely made it back to work on time. I told Tom that I had to get to work but my sweet Romeo insisted on walking me back to the time clock. How I wished that I had never asked to work third shift that night! But what would I have done? Taken Tom back to my place? I already knew he was from out of town, and was driving home tonight. Plus I couldn’t have done what I wanted with him anyway, I was still convinced that he believed me to be a woman. I told myself that if I had a pussy, Tom would have gotten lucky tonight if I had had to mount him in a broom closet.
I clocked in, then leaned against the wall to say goodnight, and goodbye, to my gorgeous stud. Tom leaned against me, kissing me like I have never been kissed before. My knees were weak as I tried to drink from his lips. We stood there at least an hour as he sweetly tasted me and lovingly stroked my breasts. My inhibitions were all but gone; I don’t believe I even realized that I was really a man by the time he said he had to go. I cried, holding him tight and refusing to let go of him. I begged him to get closer to me, and he tried, pinning me against that cold cement block wall as he melded his body to mine.
And there was his cock, raging and hard and pushing into my belly button. I gave up then, looking up into his baby blues as I came in my panties.
My moans may have given me away but I simply told him that I had to ‘freshen up’ and that he was to wait for me right there until I could give him proper goodbye, and as I said this I stroked his erection through his thick jeans. I don’t think a gun would have made him leave at that point. I hurried into the ladies room and cleaned myself as best I could, touched up my makeup, in particular my smeared lipstick, and then hurried back to my man.
Now it was his turn to lean back against the wall by the time clock. I threw myself against him, kissing him with all the love and passion that had been building in my life. I gripped his erection tightly, squeezing it until he gave me a groan of satisfaction. I then dropped to my knees, unbuttoning my shirt as he unfastened his jeans. When I took him into my mouth I wanted him to see the soft, lacy slip and bra I wore, showing him just how feminine a woman it was that was about to suck his cock.
He was taking too long getting himself free of the jeans, so I began to help him. I was scared and excited and couldn't wait to get my hands, and lips, on him. My few sexual experiences had all been with women, and now it was my turn to be the woman.
Finally I got his zipper down, biting his cock through his underwear in my passion. He pulled his briefs down and his beautiful cock sprang free. My face was so close it bounced off of my nose. I immediately began licking the underside of it, so lost in the passion of the moment that it seemed my entire awareness existed only in those parts of my body that were touching his cock.
And a beauty it was. Long, thick, and hard, I'd never seen anything to match it. I gripped it with both hands and still had plenty to work with my tongue. I met his eyes when I couldn't stand to wait any longer, and looked lovingly at him as I finally took him into my warm mouth.
I don't know which one of us groaned louder, or enjoyed the blowjob more. I worked my lips up and down his hard rod, using my tongue to inspect every inch, every bulging vein as I bobbed up and down on him. I maintained my suction all the while, releasing one hand from his cock to reach up under his T-shirt and stroke his muscular body. It may have been an hour, or it may have been only a moment or two, but all too soon he groaned and began bucking his hips, feeding me his delicious cock as poured his cum into my grateful mouth.
His semi-hard cock slipped from my lips but I didn’t stop making love to it. I continued to lick it while adding occasional kisses and gentle sucks on the very tip. I caressed his balls and stroked the sensitive spot behind them. By the time his breathing slowed from his first orgasm, his cock was once again rock hard and nestled firmly inside my mouth.
Our lovemaking was slower this time as I gently nursed on his hard prick. I slid up and down his pole slowly, keeping a steady suction as I firmly but gently rubbed my tongue over him. The feelings were fantastic. I was keenly aware of my stocking covered knees touching the floor, even through my pants. The steady squeeze of my bra and the satiny grip of my panties were exquisite, as was the hard yet soft texture of my man’s hard dick sliding across my lips.
He moaned, he groaned, and somewhere along the line I came in my panties again. I made it last as long as possible and although my jaw hurt terribly later, it all just felt so right. Regretfully my loving attention became too much for him, and he fountained a massive load of cum into my mouth. Not regretfully that he did it, just regretfully he came so soon.
I licked his cock clean and we said a tearful goodbye. Well I was tearful; Tom was weak in the knees yet completely sexually satisfied. He promised to look me up next time he came to town.
After he left I flew back to my office, I say flew because I’m pretty sure my feet never touched the floor along the way, and stripped off my hated uniform when I got there, nudged my soiled panties to the side, and mounted my dildo right there in the office; I didn’t care if anyone caught me. Of course you know whose face was in my mind as I bounced happily on that plastic cock don’t you? The same one that has filled all my private fantasies every since.
Somehow I managed to finish enough work that I didn’t get into trouble. It’s only been a couple of weeks since I had Tom, and as yet I’ve not seen him again around the plant. I know that if we do ever meet again it will likely be very awkward and likely a bad scene for me, but as long as I work here I’ll have my memories of that beautiful man and the taste of his delicious cock. At least twice a day I pass by that same time clock and gaze fondly at the spot where I once knelt with him in my mouth.
By Teresa Ann Wood
When Tom, now Teresa was cursed for his mistreatment of women, he had only a certain amount of time to fulfill the terms of the curse, learning what it meant to be a woman, or be stuck as a female forever. As his time ran down she desperately entered a contest at the urging of her friends as a last attempt at salvaging her old life.
I am trying something new this time. I have no real story here, just a prelude to some hot action. Based on the feedback I have received, this is what most people seem to want. The history that leads up to this story is alluded to but the exact details are left to the imagination of the reader. Hope you enjoy!
“Ok, here’s how the contest works,” Kelly stated from her perch atop the coffee table. “Each guy puts twenty bucks into the bucket, then takes off his clothes and sits down. We’ll draw lots to see which girl sucks which guy. The girl who makes her guy cum first wins half the money. The guy who manages to hold out until last gets the other half.”
“That’s a win/win situation for the guys; they’ll get at least a blowjob out of it,” laughed Christy who stood in the circle of our closest friends in one corner of the room.
“Twenty dollars for a blowjob is pretty cheap,” added Stacy. “I bet all the guys will want to be in on this.”
“Well they can’t all be; you can only have as many guys as you have girls, and I doubt there will be very many wanting to get in,” offered Tonya.
“Speak for yourself,” stated Christy. Everyone knew how much of a slut she was.
“There’s a bunch of drunk girls here; I’m sure some of them will get interested when the pot goes over a hundred bucks or so,” said Rhonda.
“What about Teresa? Shouldn’t she get in on this?” asked Tonya.
Everyone looked at me; I’m sure my face must have been blood red. I hadn’t had that much to drink.
“No way!” I announced. “I’m not sucking anyone’s cock; not for money, not for any reason!”
“But this is the perfect situation,” Rhonda said, cutting me off. “You’ve been practicing on that dildo for weeks, and what better way to finish off your education as a woman? You give one blowjob in a public place where you won’t have to worry about being forced into anything more. We’ll all be here to help you. If this doesn’t fulfill the terms of your curse, nothing will!”
“And we could talk Chuck into entering the contest; we’ve all seen how much you enjoyed dancing with him, and he’s not a jerk like that Todd you were making out with,” offered Jill.
I tried to protest, again, that I hadn’t been making out with Todd; he’d been making out with me! And as for Chuck; he’d been sweet as we danced but I certainly didn’t want to suck his cock. Rhonda cut me off again.
“And all the boys here tonight are super cute, so it’s not like you’re going to draw some dork’s name,” Jill added.
Finally I managed to squeeze a word in. “Chuck knows that I wasn’t born a woman and was just trying to help me fulfill the terms of the curse, whatever they are,” I protested. “I don’t want him to stick his dick in my mouth!”
For the first time Angie spoke. “No but you want to become a man again don’t you? Learning how to be a woman is all that will do that, right? You only have a few more hours before the deadline, and you’re still in the body of a college cheerleader. Everything you’ve done up to now hasn’t helped you; you’re going to have to step it up or you just might be a woman forever.”
She certainly had a good argument. I wasn’t sure what constituted learning how to be a woman, the exact details had been left for me to figure out, but living as one for the past month hadn’t been enough to release me from the curse, and neither had my experiments with the dildo. Then Rhonda sealed the deal.
“Unless of course you’ve decided that you want to stay a girl.”
No, I didn’t want that.
By the time the contestants were all sorted out there was something like twenty guys entered into the contest but only six willing girls counting me and Christy. To my surprise they made all the guys pay their money and announced that only the six names drawn would get to actually participate. A few dropped out right then but most stayed in; I guess they thought that twenty bucks was cheap even for the chance at a blowjob. Not all of them were as cute as Jill proclaimed but the six that ultimately had their names drawn weren’t bad. I kind of knew them all but only one well; Chuck. I hoped to get him, because at least I knew him and he had been nice to me.
Nervously I took my place before the guys, keeping my eyes on their feet as I embarrassingly waited to hear who I was going to have to suck. I had no thought about winning the money; I had no idea how to suck a dick, nor any desire to. I just wanted to get it all over with and hopefully get the curse lifted. Hadn’t I learned my lesson? I thought that I had. I would never think lightly of women again, nor treat them badly.
Three couples were announced before my name was called. Chuck was still without a partner. He smiled supportively at me as he tried not to stare at my cleavage. Shakily I stepped up to the ice bucket and reached in, praying that it would be Chuck’s name that was called.
Kelly spoke as she unfolded the name I had randomly chosen. “And Teresa will be partnered with... Bobby Thompson!” she announced with a flourish. My heart sank; Bobby Thompson? I didn’t even like him!
Bobby was a jerk; a ladies man and a heartbreaker. I also had to admit that he was very handsome and, rumors said, very well endowed. His blond hair and blue eyes had melted the panties off of many a young coed and my face must have showed my disappointment; he was probably as experienced at sex as any man in the room and it would be impossible for me to get him off and even if I did it would take me forever. Not that I wanted to get him or any man off, but that might just be the ticket to my return to manhood. I hoped I didn’t throw up on him.
“Alright gentlemen, strip down,” Kelly ordered.
The girls in the room cheered as the boys obediently did so. The rumors were true; Bobby was not only gorgeous; his cock was huge. That was when I had a disturbing thought; did I just think that Bobby was gorgeous?
Not that he had the only big cock in the group; Chuck standing right next to him was pretty impressive too. In fact his cock was actually prettier, if not bigger, and jutted proudly out. Disturbed again I found it difficult not to stare at them; why was my mouth watering? Why was the sight of them making my knees weak?
“Now ladies,” Kelly stated, turning to us. “You have a few moments to prepare yourselves. Remember; you want to make him cum as quickly as possible, so how you look, and what you show might be as important as what you do. The first spurt of cum has to be in your mouth, no hand-jobs only, then you have to pull back so we can see the second one spurt to determine the winner. We’ll also need to see the one in your mouth. What you do before and after that is completely up to you.”
The bitch. She was really enjoying this. I noticed that she wasn’t participating in the contest; it had probably been all her idea in the first place and designed to humiliate me because I was the better cheerleader.
Immediately the girl to my right, named Grace if I remembered correctly, stripped off her dress and then her bra, exposing her breasts for everyone to see. She had drawn Chuck, and she was busily making seductive poses for him as she squeezed her tits and ran her tongue over her lips. Chuck’s eyes widened slightly; she was hot, and he glanced apologetically at me. I don’t know why he did that; I didn’t care who sucked his dick... did I?
Somehow I found myself unaccountably jealous. Looking around I saw that all of the other girls had breasts exposed or had stripped off their panties; one girl was completely naked! Christy was only in her panties and had pulled them up into a distinct camel toe. Bobby was watching me expectantly, hungering for a sight of my beautiful body. Well he could just keep on hungering; I wasn’t trying to win this competition; just finish! I unfastened the top button on my dress so that the tops of my breasts and the uppermost cups of my bra were exposed, but that was it. I wasn’t about to show any more than that. I’d do my best because I had to; no one needed to see me naked.
He was disappointed I’m sure but Bobby’s thick cock didn’t soften one little bit. It remained as stiff as my arm as he looked around at the cheerleader flesh exposed all around him. More nervous than ever I stepped forward when told to do so and dropped to my knees. I was scared to death of this thick piece of meat! What was I doing here?
I was wearing panties, pantyhose, bra, slip, and a dress, kneeling before a good looking man so that I could suck his cock while others looked on. Not only was I wearing women’s clothing and makeup; I was truly a female with all the physical equipment that entailed. And I was a hot one too! And a cheerleader! As difficult as this was to believe, there was another thought that kept intruding in my mind.
I wanted to suck Bobby’s cock.
True, if I had my choice it would have been Chuck’s cock I chose to suck, but I wasn’t nearly as disgusted by the thought of taking Bobby into my mouth as I thought that I should have been. I was looking forward to it! What was wrong with me?”
“Remember, you can’t touch it until time is started,” came Kelly’s voice. “On your mark, get ready... GO!”
Startled despite her countdown I was the last to reach out and take my man’s cock into my small, delicate hand. It was a true monster and I found myself fascinated by it. Gripping it tightly in one hand I gently cupped his balls with the other as the cheers of encouragement from the onlookers began. The girls to either side of me were furiously sucking cock, with that bitch Grace already deep-throating Chuck. A flurry of movement to my left brought my attention to the naked girl, to see her straddling her now-sitting man and working his cock into her pussy. That was cheating! No, I realized, it wasn’t; the first splash of cum had to be in her mouth and the second visible for all to see; what you did before was up to you, hadn’t Kelly also said after? Oh yeah, that was up to you too.
“Come on, Teresa, you can do it,” shouted Rhonda. She and my other friends were standing just behind Bobby, cheering me on. With a nervous smile of thanks for their support I gave in to their urging and the desires of my rebellious body. Pulling Bobby’s cock downward I leaned forward and kissed it.
Well the taste wasn’t too bad. Kind of sweaty but not terribly so. A drop of precum was visible on the head and I got a little taste of that too, finding it salty but not disgusting. Remembering the lessons learned from my dildo I worked up a mouthful of saliva and began licking the cock, starting at the base and working my way up to the tip as I soaked it down. Someone was moaning to my right; a guy about to blow already? But I ignored them and concentrated on what I was doing; I wasn’t trying to win, only finish. Once I had his dick thoroughly soaked I moved back to the head and twirled my tongue around it a few times, trying not to think about the string of precum that was stretched between my lips and his pee slit. Then I opened my mouth wide, looked up into his eyes, and lowered my mouth onto his cock.
And had an orgasm.
I’d never had an orgasm that felt that good. Not as a man, not when working my vibrator in and out of my pussy. I hadn’t even realized that I was close, until it happened.
Looking back up at Bobby I trembled with my release as I held him in my mouth; gently nursing on the tip of his cockhead as I came. His eyes widened at the sight, could he possibly know what had just happened? The overwhelming urge to take him into me, all the way into me, washed over me at that moment and I slid my mouth slowly downward onto his rigid tool, his eyes slowly closing the further he slid into my mouth. Groaning with thanks he felt my lips touch his pubic hair, all my practice with the dildo hadn’t been for nothing, and I glorified at the feel of his manhood in my throat. That’s when I felt the second orgasm beginning.
Slowly, lovingly, I slid my mouth up the long length of his rod, sucking and licking my way back up. With just the tip in my mouth I licked the cockhead and then just as slowly slurped my way back down, glorifying over every inch that slid past my lipstick covered lips. Each second of sucking brought me ever closer to another orgasm and after only four or five strokes I could contain myself no longer and felt another tremor begin. Gripping his delicious cock in both hands I looked up to find him looking back down at me, his mouth agape and his eyes fixed on the point where my lips touched his cock. He saw me trembling, recognized my orgasm for what it was, and then closed his eyes with a sigh as he flooded my mouth with his sperm.
Surprised I swallowed the first jet of his seed and then the second filled my mouth as he blasted his appreciation of my oral skills into me. Belatedly I remembered why I was here and pulled his meat from my mouth in time for the third blast of cum to spray into the air, splashing across my left cheek in a line that ended on my shoulder as a cheer arose from the crowd, while I obediently held my mouth open for everyone to see the cum on my tongue. Kelly had not said what to do after that and without thinking I slid Bobby’s cock back into my mouth and nursed him dry as I finished my own orgasm. It had been even better than the first.
Feeling someone slapping me on the back I reluctantly released my lip-lock on Bobby and turned to find my friends gathered around me. One by one they gave me hugs and congratulated me. I had won!
Still on my knees I looked around at the other contestants, seeing that the nude girl was grumpily pulling on her panties as she tried to see out of the eye not currently coated with her man’s cum. Another man groaned and pasted his cheerleader’s face with a long blast as I was watching, and his voice was then matched by another behind me. Four of the six men were finished and two of the girls were still working. For a minute or so they continued to face-fuck their partners but, realizing that they had already lost, the girls both lost their enthusiasm for the contest and slowed down; making only half-hearted attempts at getting their men off even as the guys worked hard to keep from busting their nut first and so losing. When the crowd started yelling for them to finish what they started one of the girls gave in and with one furious flurry of activity had their man blasting his load in moments. That left only one couple still working, and so the male winner of the contest was proclaimed.
Chuck had won! By this time I had forgotten what it was that he had won, so amazed was I by the two hundred in cash I myself had just earned. When she realized that she was the only one still with a hard cock in her mouth, Grace grumpily pulled off Chuck and got to her feet, pulling her dress on to cover herself and grabbing her bra from the floor.
“Wait a minute, he’s not finished,” someone in the crowd yelled, pointing at Chuck’s still-rampant dick.
“Yeah, well I am,” Grace stated. “He was the last one, so he won. I don’t have to finish him off,” she added.
Several people booed her but Grace didn’t care, stomping angrily from the room. I still sat kneeling on the floor, amazed at my victory and flushed from my orgasms as I watched her leave. I looked back over to see a disappointed and yet elated Chuck still sitting on the couch with his thick dick sticking up in the air. She could have at least finished him off; he was awfully good-looking and his cock looked delicious. I’d have much rather sucked Chuck’s cock than Bobby’s, and here she was leaving him high and dry! That was when I realized that I didn’t need to remain disappointed; I could have him too! With that thought I slid over to kneel in front of Chuck and immediately slid his cock into my mouth, causing the room to go silent for a moment before erupting into cheers.
And it was wonderful! So much smoother, and yet harder, than Bobby’s had been. If I hadn’t been in a hurry with Bobby I was much less so now with Chuck, and took my time as I lovingly slurped on his member. He groaned the moment my lips touched him and I did what I could to keep him from coming too soon. But after studiously resisting Grace’s attentions for so long he couldn’t help but give in to my superior cocksucking abilities, and far too soon for me he was blasting his cum into my waiting mouth.
I didn’t pull it out for everyone to see either; but kept it right there until I had milked him dry.
Standing up to the cheers of the entire room I smiled embarrassingly at Chuck before fleeing back to the protection of my friends. They were leading the crowd in chanting my name as Kelly announced me the Cocksucking Queen of the Campus! I didn’t want to be thrilled, but I was. I was so proud!
From somewhere they brought up a trophy, two gigantic lips on a pedestal. Two hundred dollars was pressed into my hand as my friends congratulated me. Then Chuck was there, and we were kissing.
People were still congratulating me when Chuck whispered that it was time for us to leave. Holding his hand I waved goodbye to my friends and allowed myself to be led from the party. Any thoughts of breaking the curse were gone now and all I had on my mind was getting fucked by Chuck right now! We had all been drinking so a line of taxis were waiting outside.
I mounted Chuck in the backseat of the taxi, sliding his sweet, hard cock into my pussy before we were even pulled away from the sidewalk. Facing him I slid up and down his glorious rod, all our naughty parts hidden by my dress though the driver turned his mirror to see what he could. The muscles of my pussy gripped him hard as we fucked, with Chuck thrusting his hips up on each of my down strokes. I came over and over but he held out, staying strong and orgasm-free until we reached his apartment. He was hard as a rock!
Not even waiting for Chuck to get his change I grabbed onto his cock and led him into his apartment on the run; I wanted him back in my pussy! We didn’t even get the front door closed; I turned and dropped onto my back right there in the floor, tugging my dress up and out of the way of my pussy. Obediently Chuck lowered himself onto me, lining up his precious manhood with my vagina and easing it home, where it belonged, deep inside me.
Groaning and chanting his name I wrapped my legs around his waist as he fucked me, slowly but surely picking up speed as his thick meat split my pussy open wide. The friction against my clit was amazing and he certainly knew what he was doing; within a very few minutes I was coming again, and not long after that he gave up the fight and sprayed a thick mass of cum inside me. It was amazing.
We took a few moments to shut the door and took turns in the bathroom. While Chuck was in the kitchen making us a drink, I took the opportunity to strip off my clothes, leaving my dress and underwear scattered about the living room as I waited for him to return. I never did know what drink he fixed me, because when he returned I was leaning over the arm of the couch, waiting for him to enter me again. He didn’t disappoint me, taking only enough time to strip before approaching and sliding himself in to the root.
We fucked there for maybe fifteen minutes, then we moved onto the couch cushions were I again felt his wonderful weight atop me as he plowed my pussy. I came again and again but still Chuck remained determined not to cum, and held back his seed even as he curled my toes. Finally he pulled out and led me to the bedroom, where he took me again on the comfort of his bed. It was there, somewhere around three am that morning, when I found the true meaning of womanhood as I gasped out the best orgasm of the night as I watched Chuck’s intent, sweet face as he sprayed my womb with his cum. I learned how to love, how to give to sex as well as take. I learned how to let others be in control, and how wonderful it could be. I knew then that the curse was broken; that my lesson had been learned and my path back to manhood was available to me.
But I no longer wanted it.