As promised, Naci Rema's rewriting of the story with her take on events if they happened in the US, and with her own twist on things.
Dare I ask which version you prefer, no rude or over critical comments please, both versions were written for fun, not for a Booker prize. Enjoy!! :)

Terry’s Story

My name is Brian Smith, and I have know Terry Jones since we were kids. We played on the same street, went to the same school and got involved in the same things when we were little. As we grew up, I got bigger and stronger and was good at sports, while Terry just seemed to stay short and skinny and avoided athletics. In fact, he was always the smallest boy in our class, and even by the time we reached high school he could best be described as a runt. As such, the bullies would have picked on him mercilessly, but he managed to keep them laughing by using his high pitched voice to imitate our female teachers. And, off course, he had me as a friend who would stick up for him if necessary.
The other difference between us was our home life. My parents might have started in the same area as Terry's family, but my dad worked hard at building a profitable business and we moved into better places several times, until we had a big house in the nicest part of town. It was a mansion compared to Terry's tiny home, but at least he did have his own room because he was an only child.
The reason for my friend’s relative poverty was because his father had run out on the family shortly after Terry was born, leaving his mother to raise and support him on her own. Even though she had a decent job, money was always tight. This was made even worse in recent years because she had developed a chronic illness which caused her to miss work a lot. Terry was a good son and did his best to take care of her, which with school and homework didn’t leave him much time for a social life. This was just as well, because a small, shy, skinny boy attracted little interest from the girls.
A very significant event occurred during our junior year in high school. At the time I had just turned seventeen, but Terry was still fifteen due to his having skipped a year of school early on. While waiting in line with him at the school cafeteria, I noticed a sign on the bulletin board about a 'Womanless Beauty Contest'. Neither of us had heard of such a thing, so we read the small print and learned it was a fundraising idea the school board had come up with to help make up for the recent loss of state funding for music and arts programs. Boy students would dress up and perform like women do in normal beauty pageants, to the amusement of their family and friends who would buy tickets to attend. The main thing that caught my eye was the winner would get $500!
We were eating our cold pizza and cokes without saying much until I blurted out, “Terry, you should enter the contest! With your longish hair, baby face and small size you could easily look like a girl. And more importantly, you could really use the prize money since you’re always saying how broke you are.”
He just said, “No way!” and gave me an ‘are you nuts?’ look, but I ploughed on with ideas. I could get some clothes off my sister, who was about his size. His mother, although frail, never looked anything but well dressed with perfect makeup, so she would surely be able to help in making him look attractive. And, for once, his small, almost feminine features and lack of muscles would come in handy!
I kept on pressuring him, though I wasn’t quite sure why. In the end I made him promise to tell his mother about the contest and see what she thought of it. Terry was never a strong willed guy, and I just overpowered him with my more forceful personality.
The next time we saw each other, I immediately asked my buddy if he had told his mother about the contest. He reluctantly admitted that he had, and then, red-faced, he went on to say she not only thought his entering it was a great idea, she insisted he sign up right away! I could tell this was not what he had wanted to hear, but Terry was always an obedient son, and so before the day was over we went to the school office and filled out an entry form for him. Since it was all my idea, I even paid the fee!
And so, little Terry was going to be in a beauty pageant, and for some strange reason I was as excited about that as my friend was upset about it. The date was four weeks away, just before the Easter break, so we had time to prepare and plan for his performance.
My first job was to ask my sister Mary if I could have some cast off clothing of hers. When she asked what for, I explained that it was for my friend Terry, who was going to be in a beauty pageant. She looked at me with a funny smirk on her face, but agreed to give me some of her old things. I left her room with several bags of clothes and shoes, and an offer to help in getting my pal to look like a girl if it was needed.
Next, I went over to Terry's house and found him cleaning the kitchen while his mother was resting in a chair watching TV. As always Mrs. Jones greeted me with a smile, but she never got up, just tucked her medicine bottles out of sight. A minute later, Terry came out to say hello. He was wearing one of his mother’s aprons and looked surprisingly feminine already. I showed him the bags of clothes my sister had given him, and while Mrs. Jones seemed pleased, I saw in my friend’s face a sad, almost resigned look.
I was invited to stay a while and visit, but after a polite chat I got up and left. Terry’s mother said they would sort through the bags later on and see what there was that he might be able to use for the contest.
I would have loved to have been a fly on the wall as my friend tried on the sexy clothes and high heel shoes my sister always wore, but I had to make do with an update when we met at school two days later. In a hushed whisper he let me know that his mother had insisted he try on everything Mary had offered him, and he now had more girl clothes than boy stuff hanging in his closet! For some reason that I couldn’t quite understand, hearing this excited me.
Terry then produced a list of things his mother said he would need if he wanted to be the prettiest boy in the contest. First, high heeled shoes…neither my sisters nor his mother’s were the right size or style; and also makeup…his mother had some, but not the right sort apparently. I learned she did however have a wig Terry could use. Even though his hair was a little long for a boy, it still wasn’t the proper length for a beauty pageant, and fortunately her wig was.
I also learned Mrs. Jones had some silicone breastforms she wanted her son to use! Terry’s face turned red as he explained that they were apparently very realistic, since his mother had assured him they would jiggle and bounce just like real ones when he walked! Cancer immediately jumped to mind as the reason Mrs. Jones had them in the first place, but I didn’t wish to pry in case I was right.
By this time I was really getting carried away with the whole thing, and I immediately offered to buy my friend the needed high heeled shoes and ask Mary for makeup and wig styling advice. It looked like this was going to hurt my pocket as much as it would hurt Terry's male ego, but strangely, I didn’t care.

That Saturday found me at Terry's again. This time things were very different - his mother answered the door with a big smile on her face! She gave me a peck on the cheek and ushered me into the living room. As I sat down, I was wondering what to expect next. I quickly found out when Mrs. Jones called to the kitchen, “Come on in, Teresa. It is only your friend, Brian. Come and show him how good you look!”
The first thing I had not expected was that Terrance, as his mother always called him, would now be called ‘Teresa’. The next was the person who stood at the doorway, head bowed, looking very nervous.
“Come on now, Teresa, let our guest see you.” When Terry slowly walked over and stood in front of me, I was speechless! He was wearing a blue long-sleeve top, a knee-length skirt, beige pantyhose, and black ballet-type flats. That was only the start. The chest on 'her' looked just right (later I was told it was a C-cup), and “Teresa’s” hair was now shoulder-length, thanks to his mother’s wig. Also, when ‘she’ looked up, I could see some make up had been applied, which had made a big difference to the formerly boyish face, and ‘her’ fingertips now sported long pink artificial nails!
“You won’t tell anyone at school you saw me like this, will you?” he asked nervously.
I agreed not to, but from that moment on I knew Terry, or rather, Teresa would be a hit at the contest. But more than that, I found seeing him dressed like a girl to be unnervingly appealing. While I’d never had a girlfriend before, and I had often looked at girls and rated them on their attractiveness, and ‘Teresa’ was off the charts! I wanted to tell Terry how beautiful he looked, but it seemed wrong for me to say to my boyhood friend something that would only be appropriate to tell a girl. His mother had no such hang ups and went on and on about her lovely ‘daughter’! Finally, an embarrassed Terry had heard enough, and he went off to get us all a drink, much like he would have done before, but dressed as a girl he just seemed to be acting more in the feminine role.
While we enjoyed our iced tea, we talked about what ‘Teresa’ would require for her further development. And once again, I offered to pay for anything extra that was needed. Mrs. Jones patted my hand and thanked me for my support. Then, she made plans for me to take Terry shopping the next day for women’s shoes, and if Mary did not have any spare makeup, we would buy some of that, too. I was wondering how two boys might get away with shopping for such girly stuff, but that was just something we’d have to figure out if this idea was going to succeed.
After a while we left Mrs. Jones on her own and went upstairs to Terry's room. It was certainly different than I had remembered, with my sister’s clothes hanging in his closet, her shoes on the floor and in front of a mirror were the few makeup bottles he had used.
I started off with, “Wow, I thought you would just have to wear a dress on the day of the pageant, not all this!”
Terry looked down at the floor. “Pretending to be a girl is not that easy. At first, I wanted to do as you said, but Mom decided I need to get used to the ways of femininity if I want to win the contest. The only good thing about all this is that my mother has been the happiest I’ve seen her in a long time. She’s really enjoying having a ‘daughter’ around for a change.”
“What do you mean by getting ‘used to the ways of femininity’?”
Terry hesitated before finally blurting out, “Mom thinks I need to live as a girl as much as possible during the next few weeks! She wants me to sort of immerse myself in the role, so that when I walk out on stage I’ll think of myself as Teresa and not Terrance!”
“Are you kidding me?” I asked in amazement.
“Unfortunately, no. Mom says from the moment I get home from school until I leave to go back the next morning I have to dress and act like a girl. She’s begun to scold me if I show any boyish traits, and insists I spend most of my free time practicing styling my wig and putting on makeup!”
I tried to stop myself, but then it was my turn to blurt out, “If I was to say you look pretty already, would you be mad?”
“I…I guess not, but don’t you think this whole thing is kind of strange?”
Quickly I replied, “No, it’s just all in fun, right?” I wasn’t going to admit to my earlier thoughts that I was actually feeling attracted to him. I was sure he’d quit the contest immediately if I did, something I was suddenly anxious not to happen.
Terry changed the subject to school, and asked which girls I found attractive. I admitted it was the ones who had long, slim legs and big chests. “A typical guy answer,” he replied with a smile, which looking the way he did didn’t sound strange at all. I asked what he looked for in a potential mate, and he said he thought friendship and a common bond were more important than appearances.
To this I immediately replied, “Well, I also think those things are important in a relationship. For example, with us we have the friendship, a common past, and now a common purpose, you winning the contest.”
“And you’re not just saying that because I have nice legs and a good pair up here too?” he asked with a grin as he glanced down at unfamiliar mounds on his chest. I knew Terry was just teasing me, which was good since it meant he was becoming more relaxed with his new feminine appearance.
“The nice tits do help, but I'll pass judgment on the legs until I see you in a mini-skirt!” For that comment I got hit on the arm. Only, it was not a hard punch a guy would have given me, but more of a girlish, playful slap. I was pleased that even alone with me Terry was staying in the role of a girl.
I looked in my friend’s eyes, which seemed softer and more alluring from the makeup. “So, do I call you Terry or Teresa now?”
“Mom says it should be Teresa when I’m all dressed up like this,” he replied bashfully.
“I think your mother is right, Teresa. And, if you practice hard I’m sure you will make an excellent ‘womanless' beauty pageant contestant!”
Nothing much else happened that evening, but I did arrange to meet Terry at the local mall on Sunday to buy him some high heeled shoes. Once again, I was feeling excited, picturing how much sexier ‘Teresa’ would look mincing about in towering stilettos!

I met up with my friend at the mall as planned. I smiled when I saw that he looked very nervous and was wearing a baseball cap and sunglasses to try and hide his identity. Despite that, with his longish hair and pretty face he still appeared very girlish, which pleased me greatly.
When I asked how he was doing, Terry turned bright red when he said, “Mother thinks I need some new girl’s underwear as well, if you can afford it…” I didn’t answer immediately, my mind trying to picture my boyhood friend all dressed up in sexy lingerie like I had seen in Victoria’s Secret! So, he continued, “Just panties really, and maybe a bra. I hope you don't mind, but Mom’s social security check hasn’t come yet this week and we’re kind of short.”
“I don’t mind paying for your girly underwear,” I insisted, “but how can you be sure of the fit without trying them on?”
“Mom said buying the feminine undies will be no problem. She wrote down my sizes and told me to just say they are for a girlfriend.”
And so, we went into a women’s clothing store, blushing a lot as we walked along the racks of soft pretty underwear. I smiled when I noticed Terry nervously fingering a lacy black bra. I’m sure he was agonizing over the fact that his mother had insisted that he wear such garments on a daily basis until the womanless pageant.
“Can’t we just buy some plain white cotton bras and panties?” he asked hopefully.
“Of course not!” I replied with big grin. “You want to be thinking like a sexy girl for the contest, right? That means you should be wearing the hottest underwear we can find, to put you in the right frame of mind.”
With that I headed over to the bra and panty sets and picked out the most sexy ones they had in my friend’s size. Terry made one last protest that the garments were far too sensual and erotic for a boy to be wearing, but I just grinned and took the lingerie to the checkout counter.
I walked up to the cashier and muttered something about them being for my girlfriend. The older woman glanced over at my feminine-looking companion and said with a smirk, “I hope she appreciates how embarrassed you are getting these things for her!” I turned bright red when I realized the cashier knew they were for Terry, and I paid without saying anything else.
Fortunately, my friend hadn’t heard her snide comment, since he was desperately trying to figure out how he could try on women’s shoes without being labeled a queer. Suddenly, he had an idea. We would avoid regular shoe stores and just shop in one with rack upon rack of stock. There, he could try women’s shoes on without any salesman’s help.
And so, we walked around the mall until we found that kind of shoe store. The plan was simple. First, we would wait until the aisle containing his size was clear. Then, while I looked out for anyone coming, Terry would slip his shoes off, revealing feet encased in girls tights, and try on some appropriate high heeled shoes.
Having seen many beauty contests on TV, I had a good idea of what to look for. And, in the third shop, I found them — pointy-toed, black stiletto, 4 inch pumps! Terry immediately protested, saying he could never walk in shoes with heels that high, but I was insistent and he finally gave in and tried them on. At first Terry complained that the pumps were too tight, and I explained that my sister said the same thing about her shoes but wore them anyway, because they made her feet look smaller and more feminine. Hearing that, he reluctantly forced his feet into the pumps and stood up. I had to catch him when he did, because he almost fell over from being unsteady in the unfamiliar skyscraper heels! Gradually, he regained his balance and managed a few tentative steps, teetering precariously the whole time. I wanted him to practice some more, but Terry heard a salesgirl approaching and quickly slipped the shoes off and back into their box. I blushed again as I went to pay for them. No comment this time from me or the assistant, just a ‘no’ when she asked if I wanted any stockings to go with them.
I had reached my limit on embarrassment, and we still hadn’t addressed the makeup problem. Luckily, Mary had said she would go out and buy what she called a “starter kit for the beauty queen!”, so we called it a day and went back to Terry’s home to show his mother his new lingerie and high heels.
On Monday I brought him the make up Mary had purchased. My boyhood friend was all set up now for his big day as a woman in a beauty contest! I wondered if that thought made him shiver as much as it did me.

A week of school past and there wasn’t much talk of ‘Teresa’ until Friday, when Terry asked me to come by his home the next day. I asked him what for, but he refused to say anything more.
On Saturday I was greeted at the door by Mrs. Jones, who gave me the now customary peck on the cheek. Once again, Terry was in the kitchen, and I could see from the back that he was wearing a velvet dress, dark stockings and the new high heeled shoes. I was going to say something corny like, 'You look good enough to eat!', but stopped myself when he turned around. I couldn’t help but stare at his soft wine-colored lips, big defined eyes and the inviting mounds on his chest!
Mrs. Jones then spoke for me. “Teresa does look beautiful, doesn't she?” I was at a loss for words. “I tell her that all the time, but she doesn’t seem to believe me. You tell her, Brian. I am sure she will trust you.”
“Well, er, yes, he…I mean…she looks…well....er... very pretty!”
Terry looked down at his feminine-looking hands tipped with long wine-painted nails, and said in a soft, higher pitched voice, “It's alright, Brian. I know I look like a girl…I just don't want to believe it.”
“Well, you had better believe it!” I almost shouted, “because you look fantastic!”
Terry blushed prettily and then went over to the table and laid out the food for our meal. It was obvious he and been practicing walking in the tall spike heels, because he handled them as well as any real woman would. I was mesmerized as the stiletto pumps caused his shapely behind to wiggle enticingly in the confines of the tight dress he wore.
After a meal in which I couldn’t take my eyes off my gorgeous friend, Mrs. Jones went out with some neighbors, leaving us in the house alone.
“Do you realize how terrific you look?” I blurted out, still not understanding the strange emotions my crossdressed buddy aroused in me.
“Please don't tease me,” he said with downcast eyes. “I feel awkward enough as it is.”
“No, I mean it. You do look very good…even hot!”
“No, I don’t! I can’t!” Terry insisted, his eyes misting up at the idea that he could actually look desirable to other males. Finally, he calmed down and said, “Anyway, Mother wants me to go out in public as Teresa to get used to being seen as a girl before the contest. She says this will boost my confidence.”
“Mother? Since when did you start call your mom that?”
“Since she told me to. She says it sounds nicer in this girly voice she also insists I use. So listen, I’d like someone to come with me when I go out. Will you do that for me?”
What else could I say? “Of course I will. Just tell me when you want to go out, and where you want to go.”
And so, later that evening after it turned dark, we prepared to venture outside. Terry borrowed a woman’s coat from his mother to wear. It was way too short for him, but I didn’t mind since it gave me a better view of his long, slim legs perched on the skyscraper heels! I began to walk to the front door, but Terry insisted we slip out the back door after I had made sure no one was watching. The outing consisted of a bus ride into town, a short walk around with Terry’s spike heels echoing off the deserted streets, a coke at a Burger King and then back on the bus. We were home by nine. Mrs. Jones was thrilled to hear about her “daughter’s” first time out in the world, and thanked me for being such a good friend.
As I left, she thanked me again, and I said anytime Teresa needed someone to take her out, I would be only too glad to volunteer. Mrs. Jones replied, “That would be wonderful!” and gave me a big hug. I doubted if Terry was quite so enthusiastic about the idea, because when I asked him if ‘Teresa’ was free Sunday evening for another trip outside, he just quietly said, “I’ll see you tomorrow.”

I arrived as requested the next evening, and took Terry for a walk around a nearby park. This time he wore a hooded coat his mother had found, which would help to hide him from possible meetings with people he knew. It was a cold night, so we found shelter and huddled together for warmth.
“Mother really likes me like this, you know,” Terry finally spoke.
“I guessed as much.”
“I have to wear dressy women’s clothes whenever I am at home now.”
“ I thought so. You’ve become very good at walking in those heels.”
“I know. It took a while, but I don’t feel in pain or out of control anymore when walking in these tall stiletto pumps. In fact, it’s when I wear my normal flat boy’s shoes to school that my legs ache. I think it has something to do to my tendons becoming adjusted to the heels, since I wear them so much now. Even worse, Mother said she would like to take me out to get several more pairs of high heeled shoes in other colors, to better match some of the dresses and skirt outfits your sister gave me!”
“That’s too bad,” I replied, secretly delighted that I would soon be seeing my friend wearing some new sexy footwear.
“Brian, do you mind me doing this? I mean, do you think it’s weird that your best friend is living as a woman most of the time?”
“Not in the least. I enjoy you more as a pretty girl than I ever did when you were a sorry runt of a guy!”
“Stop teasing!”
“Okay, but you really do make one pretty girl.”
“Please don’t say that…this is all so confusing!” Terry then turned to me, buried his head in my chest and began crying. I put an arm around his shoulder, and for the first time in our lives I hugged him! It felt so much like having a girlfriend beside me that I just naturally reacted as if Terry was one. In time he calmed down, and then wiped his eyes carefully like a girl would so as not to smudge his makeup.
“We better get you home,” I said, and took my friend’s hand in mine and walked with him just like he was my girlfriend. Now I was the one feeling confused!

The next day Terry and I met for lunch at school. I noticed his face had changed. For one, his eyebrows looked thinner than normal and more high arched, as if they had been plucked drastically. He reluctantly admitted his mother had done this to him against his wishes. She said it was needed for the beauty pageant, and it was better to do it now so any redness would have time to resolve.
I could also see a silver stud in each ear, which Terry said was more of his mother’s handiwork. She had done it with an ice cube to numb the sewing needle which pierced his lobes. Ouch! I thought.
We found a quiet corner, and I started to tell my friend how confused I was by how far Mrs. Jones was taking all this, but was quickly cut off with the reply, “You’re confused? How the hell do you think I feel?”
I tried to imagine how much Terry’s life had changed since I convinced him to sign up for the womanless pageant, but it seemed Incomprehensible to me. Then, he added, “And your asking to take me out certainly doesn’t help things!”
I told him honestly that I was best friends with Terry, but when I was around Teresa I somehow felt like I should ask her out. In reply, he insisted that I resist this urge and never suggest to his mother that we go out in public together again. He explained that she was already hinting that the two of us should go out on a real date together, which would be venturing further into a female lifestyle than Terry was ready for!
Then, he floored me by asking if Mary had a prom gown or some other fancy long dress that he could use for the contest. I said I would find out, but I doubted that my sister would lend something that expensive for a boy to wear.
To my surprise Mary did have a suitable dress for the evening gown portion of the beauty contest, a blue satin gown she had worn to her senior prom. She said Terry could borrow it as long as he came over and tried it on at our place first to make sure it would fit.
When I gave Terry the 'good news' about the ball gown, he thanked me and asked if he could stay at my house for the weekend when he tried it on. He explained that he was well known around his neighborhood, and he was worried someone might recognize him out in girl’s clothes. On the other hand, no one knew him in my area of town, so he could come and go as Teresa without question. I asked about his mother's care, and he said she would be alright for one night, since Mrs. Phillips next door would look in on her.
So, we made arrangements for “Teresa” to stop at my house the next weekend. My parents knew about the contest but were still a little skeptical about having Terry hanging around dressed like a girl. That was until they met Teresa and realized how good she looked! My mother took to the feminine version of my friend right away, and even offered him hair and makeup tips. My father was certain at first that I was trying to smuggle a real girl into my bedroom, and it was only when Terry spoke in his deepest masculine voice that dad recognized my boyhood buddy and gave him the okay to stay.
Among the other things we had to do that weekend was buy Teresa some shoes to go with the evening gown. This time Mary came with us to help Terry pick out some strappy sandals to match the prom dress. There was no buying in private this time. At Mary’s insistence, he had to shop at regular women’s shoe stores and try them on right out in public! Fortunately, with Terry dressed and made up like a woman, there was little chance anyone would suspect it was really a 15-year-old boy trying on high heels!
I could see though that my friend was terribly embarrassed when Mary insisted he try on and walk around in pair after pair of spike-heeled sandals and pumps. However, to my surprise, by the third store Terry seemed much more comfortable parading around in sexy evening shoes in front of other female shoppers. Still, when Mary finally decided on a pair to buy, I saw my pal heave a sigh of relief as he shifted gingerly from one aching foot to another.
When I noticed later that the new sandals had heels even higher than on his other shoes, Terry explained sheepishly that Mary had assured him they were the best match for his gown, even though she admitted they would be a little more uncomfortable to walk in. Hearing him say this pleased me greatly, since it was another indication that my friend was thinking more like a female, who would accept some discomfort for the sake of fashion!
While we were out shopping, we also picked up some cosmetics to go with the outfit, and a small clutch bag for Teresa's incidentals. I was a little surprised to see how much like a girl Terry acted in Mary's company, but when I asked him about this he said the feminine clothes he wore influenced how he behaved. For example, high heels made him walk differently, as did the unfamiliar weight of the artificial breasts on his chest. Also, having long hair, bangle bracelets and artificial fingernails affected how he moved his head and hands, and the short, tight skirt forced him to be extra careful about how he did many things, like sitting and picking things up off the floor.
I could only smile proudly as Terry linked my arm and thanked me for buying him the new evening shoes and bag. I had spent a small fortune on a feminine wardrobe for my boyhood friend, but I didn’t mind. For some strange reason, seeing the results gave me a warm feeling inside, which seemed to grow even more pleasurable the more he became Teresa. I still couldn’t understand why, but I had become determined to turn Terry into the most beautiful and sexy girl that I could!

That evening, Mary took Terry into her room to have him try on the complete outfit. After what seemed like hours, they finally reappeared. I was shocked to see that my best friend was unrecognizable! Mary's blue prom gown fit him perfectly. The bust was full, the long skirt and hourglass shape of the dress said sexy, and when he turned around, the lacing up the back revealed a hint of ass cleavage that looked terrifically hot! I couldn’t believe how well he moved in the skyscraper heels, and the redone makeup, long earrings and alluring perfume all added to his amazingly feminine appearance.
I just stared, open-mouthed, as my sister directed Terry to stand in front of me in a model’s pose, one leg forward, the other bent, and with a hand on his hip. Suddenly, I realized I was no longer confused about my feelings…I was in love! The only confusing part was that “Teresa” was not a real woman, but at that moment it didn’t matter. I just drank in what I saw and decided to worry about the details later.
As for Terry, I could see that he was also filled with mixed emotions. On the one hand, he seemed pleased with all the compliments that showered down on him. But, on the other hand, they were about how beautiful and feminine he looked, which must have upset his male ego greatly!
After a short while of Mary and my mother fussing around Terry to make sure the fit of the gown was perfect, he was ushered out of the room and back to the spare bedroom he would be sleeping in that night. There he changed into an off-the-shoulder dress and matching platform heels that Mary had lent him. The shoes were a little small on his feet, but they had an open toe and sling back, so he managed to squeeze into them.
Terry came back looking so sexy that I could feel myself stiffening in my pants! I assumed this was going to cause trouble later, but at the moment I was in heaven! After some more talk about what an attractive and real looking girl he made, which caused him to blush sweetly, Mary invited the two of us to go out with her and some of her friends to a nearby sports bar to watch a game and have some beer and popcorn. Even though we were both underage, she was certain that everyone would assume because we were with her regular friends that we older, and everything would be fine.
Terry seemed to accept this latest trip out in public as good practice for the contest, and Mary clearly enjoyed his company and made him feel at ease. That is, until she introduced him to her friends as my girlfriend! She later explained to the embarrassed boy how it was easier to do that than tell the full story. This left me an open door to behave like an attentive boyfriend to the hot girl I was with, since I did have to maintain the cover story for onlookers.
At first, when I sat close, put an arm over his shoulder, and took hold of his hand, Terry seemed shocked and put off by my advances. But, as the evening progressed and he had a few unfamiliar alcoholic drinks, he seemed to loosen up, and soon he was laughing and having a good time along with everyone else. In fact, my boyhood pal didn’t act the least upset when I went even further, like fingering his bra strap and putting a hand on his exposed thigh. Emboldened by this, I took a chance when Mary was in the restroom to sneak a quick kiss on his cheek! There was no instant passion in “Teresa’s” response, but I was not rejected or screamed at either. I was beginning to consider the possibility that maybe Terry liked being my girlfriend as much as I liked thinking of him as such!

We got home quite late and just said our good nights to Mary, who remained chatting with her boyfriend at the door. I took Terry to the spare bedroom and asked if there was anything he needed. Then, before I could stop myself, I kissed my friend again! It lasted only seconds, but it was full and firm and right on the lips! When I pulled away I said, “I’m sorry, Terry, but you look so darn good, and with us having played a couple all evening, I guess I was still in the role and did what felt right!”
Terry didn’t speak for a minute, fiddling nervously with a bracelet he was wearing. Then, with downcast eyes, he said that it was all really his fault, and apologized for leading me on! I immediately took him in my arms and gave him a hug. Then, I kissed him again, teasing his nice-tasting lips apart for a little tongue action in the process. This time I did not apologize when we stopped. Instead, I told him he could lead me on anytime he wanted to!
When Terry gave me a pretty smile in reply, I leaned forward to kiss him again. However, he put a hand up to stop me, saying he was dead tired and needed to get some sleep. In reality, he was wide awake, but knew he needed time to sort out all the conflicting emotions he was feeling.

That Sunday I took my “girlfriend” for a walk in the woods, suggesting along the way that maybe when the beauty pageant was over, “Teresa” would still like to appear occasionally for future dates. Terry immediately made it clear that the whole female impersonation thing was to win a contest, and when it was over Teresa would be gone for good. I defended my suggestion, pointing out that his mother liked having a daughter, I liked my hot new girlfriend, and even he seemed to enjoy being a she.
Terry hesitated with his reply. I could tell he was having trouble deciding how much to reveal to me. Finally, with tears in his eyes, he poured out his feelings, saying the whole situation was making him an emotional wreck! Here he was, a normal boy, but everyone seemed to prefer him as a girl. What’s more, his mother and best friend not only seemed to like Teresa more than Terry, they both wanted him to remain that way!
I immediately considered consoling my distraught pal with a hug, but I didn’t for fear it might make matters worse. Instead, I just patted Terry on the back and reassured him that I liked him either as a boy or girl. Then, I added that for now he should just give in and be my girlfriend Teresa for the sake of the contest, and we could talk about the future when it was over. After that, I took his hand and led the confused boy back to my empty house.
There, we had a bite to eat along with some wine my parents had left out. Then, with both of us feeling very mellow, I invited Terry to sit beside me on the sofa to watch some TV. He did so, tucking one high heeled foot under him like a girl would as he sat down.
“You know, if you let me, I would love to go out with you on a real date,” I ventured.
“I know,” came the soft reply.
“So, when can I take you out?”
“Please don't rush me! I’m just getting used to what it’s like being a girl, and next week I have the contest, unless you’ve forgotten.”
“I understand…I need to back off for now. But, that’s not a ‘get lost forever', is it?”
Again, Terry hesitated, before replying honestly, “No, not a get lost forever. But for now, please just shut up and watch TV!” I complied, but before the evening was over, I again had my arm around Terry’s shoulder and my hand on his stockinged thigh. He didn’t object to this, but I knew better than to try anything more then. Still, I was now filled with hope that our relationship would eventually more to another level. Strangely, I had completely forgotten that my girlfriend’s masculine body would severely limit how far we could go sexually.

By the time my mother had packed Teresa and her belongings into the car for the trip back to her home, I was sure I was going to be seeing much more of this girl. After they left, my father had a quiet word with me, pointing out that despite how pretty Teresa looked, she was still a boy, and one they all knew well. Yes, he admitted, Terry did look convincing as a girl, but he still had all the normal boy parts between his legs!
I replied that I knew all that, but when I was around Teresa her real sex never entered my mind. Dad understood my feelings well, having himself felt a stirring in his loins whenever Terry wiggled by in a sexy tight dress and skyscraper heels! He kept that to himself, however, and just answered that he wanted to make it clear to me that what I was doing might be thought of as gay. I nodded, and then asked if he had a problem with that. He thought again of the beautiful vision that was Teresa, and finally said he just wanted to make sure I didn’t get into something I couldn’t handle, and left it at that.
Now that my father had backhandedly given me his approval by not forbidding it, I was even more determined to make Terry my girlfriend! Despite that, it felt a little odd when I met him at school the next day. He still had his own, overly-long hair, pierced ears, and thin, high-arched eyebrows, and he even walked a little differently now, thanks to the many hours spent mincing in towering stilettos. However, I had no desire to kiss and touch him like I had over the weekend, which I think we were both grateful for. In fact we hardly spoke of ‘Teresa’ other than to discuss his preparations for the contest. In that regard, most of the organizing was out of my hands. Mrs. Jones, my mother and Mary had been in touch with each other, and come Saturday, Terry's life would not be his own!
First off, he would be prepared by his mother. I was told he would have to undergo complete body hair removal, prosthetic breasts would be glued on since the prom gown was too revealing for a bra, and his wig would be firmly attached to his own hair. Then, in the afternoon, my mother would pick Terry up and bring him to our place, where Mary would make him up, style his wig and get him dressed for the evening’s performance. All I could do was get in the way, so I made sure I was nearby to enjoy watching his transformation, but not underfoot.
The contestants were asked to be at the high school gymnasium, which was all decked out for the contest, by seven PM. To my surprise, Terry was not completely ready at six, as he sat without his wig on getting final touches to his makeup while wearing a dressing gown and matching high heeled slippers borrowed from my mother. Still, I couldn’t believe how beautiful he looked already, and I was anxious to once again see him in the sexy prom dress he would be wearing for the pageant.
At six-thirty I went with my father to pick up Mrs. Jones and take her to the school. I was surprised to see how fantastic she looked, dressed in a beautiful satin gown she had last worn as a young woman. It must have taken a huge effort on her part to look so good, considering her ill health, but there was no way she wanted to miss seeing her new daughter in a beauty pageant, nor be outdone by her son in looking glamorous!
Meanwhile, Mary and my mother took Terry and the prom gown to the girl’s dressing room at the gym, in order to make any final adjustment required. I imagine that sometime in the past few weeks a conversation must have occurred about how they would approach this contest. Would Terry be an outlandish drag queen, an obvious boy with a poorly fitting dress draped over him, or instead try to appear as a real female. I wasn’t sure who had made the final decision, but I would guess it was his mother since Terry didn’t appear the least bit happy about having to dress and act like an actual woman.
As we stood around, we could see all sorts of ways in which the contest had been interpreted. There were some shocking sights, like hairy-chested guys with ill-fitting dresses and bright red clown lipstick, but most of the boys had the nerve to hide their masculinity beneath a feminine disguise. And although I was naturally biased, I was certain my “Teresa” was the best looking of all!
The pageant started with the twelve contestants walking one by one up to the stage. The next to the last one out was Terry, who I was pleased to see not only handled the six inch platform heels he had on without stumbling, they also added a nice feminine wiggle to his walk! However, ‘Teresa’ didn’t smile at all and appeared very nervous despite getting the most enthusiastic response from the audience. I was concerned that this attitude might cost him points with the judges, but fortunately when one of the boys in the audience called out, “I’m in love!” , Terry laughed along with everyone else. After that he seemed more relaxed and even smiled a little, which made me feel better.
The first activity was an interview with the host, who asked each boy his reason for entering and why he wanted to win. Most made up stories they thought the judges wanted to hear, like doing it to stretch the bounds of sexual equality, or to be a good role model for gender-challenged youth. Terry just told the truth - that his mother was unwell and the money would be a nice financial boost for them. Then, he added that I had been his sponsor, and he thanked me publicly for all my support. It’s a good thing the audience was in darkness, or everyone would have seen me blushing beet red at this!
Next was the catwalk parade, where each boy had to walk up and down a runway and end with a model’s pose right in front of the judges. Of course, Terry won that. With all the practice he had walking in stilt-heels, he was a natural strutting back and forth on the runway, his cute rear end swaying enticingly with each mincing step!
Last, the panel of judges gave each contestant a random question, such as the one Terry was asked: “Do you prefer clothes from upscale women’s fashion stores, or do you prefer buying from trendy boutiques?” His answer was, “Neither… I’d rather have borrowed clothes, because they don’t cost my poor mother anything.”
After seeing some tears in a few judges eyes when they heard this, I felt even more certain of the contest’s final outcome. However, first there was a discussion over who the finalists would be. While this went on, a DJ appeared and some music started playing. The contestants were brought down to the main floor and encouraged to talk and dance with some young men who were recruited from the audience. I have to say that Terry mingled very well. All that taking him out in public as “Teresa” was definitely paying off. However, I did notice that when one eager guy took his arm and led him to the area cordoned off to be a ‘dance floor’, Terry did have a, “What have I gotten myself into?” look in his eyes! Fortunately, Mary had the foresight to show him how to dance like a girl as part of his training, and I thought he looked quite comfortable dancing backwards and in high heels!
Half an hour later the contestants were called back on stage, and the host announced the five finalists. Then, in dramatic fashion, one by one were eliminated, each given a small consolation prize before they left. Finally, it came down to just two ‘girls’, one of which was Terry! I watched with amusement as he and the other boy held hands just like real beauty pageant finalists might as they awaited the announcement of the winner.
Finally, after a tense pause, the host declared that TERRY JONES had won first prize! He added that this included $500, plus a beauty makeover at a salon in town and a gift voucher from a local fashion boutique! Terry’s smile lit up the room when the money was mentioned, but his expression quickly turned to one of puzzlement when the other two gifts were described. Then, he smiled again when he decided that his mother could put them to good use.
Next, a sash that said “Most Beautiful” was draped across his chest, a rhinestone crown was placed on his head and he was given a bouquet of roses. Suitably decked out, he was then asked to make the traditional “winner’s walk” back and forth in front of a cheering audience. I swear I saw tears in his eyes when he did so…I just didn’t know if they were tears of joy or of embarrassment at being declared the school’s most beautiful boy!
The evening continued, with the DJ playing his tunes well into the night. Terry was asked to dance by several more young men who wanted to have a spin around the floor with the beauty pageant winner. He reluctantly complied, but I could see that he was a little uncomfortable with the way some of them pressed their bodies against his and even gave his plump behind a squeeze or two!
I was upset at having my girlfriend courted by so many other guys, and when one fellow became especially frisky with his hands, I quickly cut in. I could see the relief in Terry’s eyes when I did so. He was apparently bewildered by all the unwanted male attention.
As we danced, I became aroused by the lovely creature I held in my arms. Without thinking, I placed a hand on the small of Terry’s back and let a finger caress his butt cleavage! Happily, while this had upset him when others tried it, I got the impression he was enjoying my attention! Mrs. Jones missed all of this. She had stayed to see her son win the beauty contest, but afterwards asked my father to run her home early since she was feeling very tired.
Terry and I danced until the lights were turned on and everyone was told to leave. After that, we all returned to my house for the night. As we sat up reminiscing over how well the contest had gone for ‘Teresa’, I felt myself once more wanting to make “her” a more permanent part of my life!
After a while the women went to remove their makeup to get ready for bed. Terry obviously had to go with them, since he was still dressed and made up like a girl. While the ladies were gone, I sat downstairs with my dad. Out of the blue he told me how feminine and sexy he thought Teresa was, and that he was not shocked that I found such a girl attractive, even if she had a little something extra in her panties!
While I was trying to get over the surprise of this comment, I was dealt an even bigger shock when the others came back downstairs for a nightcap. I had seen mother and Mary do this in the past, but to see Terry come in with hair still up in a feminine style and wearing a satin nightgown and matching high heeled mules was stunning!
When he sat down right next to me, I began to get physically aroused! Fortunately, we talked for just a short while about the evening’s events before Mary, mother and dad left, reminding me to turn off the lights when I went up to bed. After the footsteps had died on the stairs and doors had closed, I turned to face “Teresa”.
“I still can't believe how beautiful and realistic you look! Just for one more night, will you be my girlfriend?” I begged.
I could see Terry hesitate. The contest was over, and what I was asking was a little strange, to say the least. But, I guess he felt obligated after all I had done for him, and so he shyly nodded ‘yes’. And then, my girl moved even closer to me!
“Everyone loves you as Teresa, you know,” I said as I put my arm around my best friend’s small, thin shoulders. Then, I took that beautiful head in my hands and brought it up towards my mine and kissed those luscious lips once more! This time I felt Terry kissing back, and when my tongue went searching into his mouth, it felt no resistance. Before long I was massaging what I knew to be fake but very realistic feeling breasts. From there I worked my way up Terry’s slim legs and underneath his nightgown. The smooth skin was luxurious to the touch and the satin fabric felt very erotic, but when I realized there were no panties and no manhood to be found between his legs, I immediately stopped and asked him what the heck was going on!
An embarrassed Terry lifted the hem of his nightie and reveal a triangle of hair and no penis! Somehow Mary had fastened it back between his legs using surgical tape. When I pointed out that with this arrangement he’d have to sit like a girl to pee, he asked wasn’t that how I’d prefer it - with only one us having a penis? Then, already knowing the answer, he smiled and put a hand on my crotch. Now, until then, no other person had touched my cock, and I immediately began enjoying the unfamiliar sensations. After a few careful strokes by ‘Theresa’, I groaned and erupted into my pants!
“Is that what you wanted?” my ‘girlfriend’ asked coquettishly.
“That was more than I expected, thank you,” I gratefully replied.
“You had a big part in my winning today, Brian, so think of it as payment for all your support.”
“Well, that was some reward!”
“Glad you liked it,” my beauty replied as he got up and walked up to his bedroom, wiggling his satin-covered behind the whole way. I eventually calmed down after that wonderful experience and went to bed myself.
When I woke up the next morning, I had the unexpected surprise of seeing that “Teresa” was still with us! I had not realized it, but Terry had come the day before in drag, and had forgotten to bring any male stuff to wear after the contest. So, unless someone went to get his boy’s clothes from his home, he would have to look like a girl for as long as he stayed with us. And, I for one was certainly not going to rush out to do that!
So, I enjoyed having my beautiful girlfriend with me for breakfast and a little beyond. Finally though, Terry was anxious to get home and see his mother, so I reluctantly drove him back to his house. I stayed for a little while to make sure Mrs. Jones was ok after her tiring day, and also to relive the high points of the womanless beauty pageant with her. All too soon, though, I had to leave my beautiful Teresa and go home to catch up on schoolwork, which I found terribly anticlimactic.

I think it was mid-week before I saw Terry again. I accused him of avoiding me, but he said his mother had not been doing well, so he had skipped some classes in order to care for her. He told me how she had been thrilled to be given the salon voucher, but had refused to accept the cash he had won. However, I was sure Terry would find ways to spend it on her anyway. As for the boutique clothing voucher, he wanted me to give to Mary. While I told him this was a nice gesture, I refused, saying she could afford anything she needed with her high-paying job and would surely not accept it either. He didn’t know what to do after that, so I made arrangements to meet him at the boutique so we would see if there was anything uni-sex he could wear.
When we arrived there the next day, a very effeminate man offered to help us. Now remember, Terry still had the plucked eye brows, his nails were still manicured with traces of polish, and he had not completely lost that swishy walk he developed while wearing heels all those weeks. The assistant must have picked up on this and immediately showed him some extremely girlish things, like a salmon-colored shirt, tight fashion jeans and black slip-on shoes with a low heel, effusing over his pretty customer as he tried each item on.
I could see that my ‘girlfriend’ was going to turn down all the man’s suggestions as being too feminine, so I quickly jumped in and insisted they looked fine on him. So, Terry finally agreed to buy the salmon top, the black pumps, and the eye-wateringly tight jeans with no rear pockets, which looked so slim on him it was like he had leggings on!
After we had made these choices, the salesclerk asked if Terry would like to wear his new things home. When he hesitated, I insisted that he do as the man asked. So, within minutes I was walking out of the shop with a person who I could tell onlookers thought was somewhere between a girl and a boy, but not sure which!
One person who definitely liked the clothes we picked out was Terry’s mother. Unfortunately, Mrs. Jones said the wrong thing when she called Terry’s new outfit 'pretty'. She was clearly in a good mood due to her salon visit earlier that day, and looked so much better for the pampering she must have received. Still, the damage had been done, and I knew Terry would always have a bad feeling whenever he wore his new things.

For the next few weeks my life went back to the old routines - school, working, family, all the normal teenager things. I tried to see Terry as much as possible, but he usually had an excuse as to why he wasn’t available. Still, we would get together occasionally, at which times I would always hint about how much I was missing my girlfriend. He always quietly told me that Teresa was gone for good, and I should find myself a real girl.
However, it was Teresa who I wanted, even though I knew that was wrong. I was never sexually attracted to Terry, the boy. In my mind to have kissed him would’ve been gay. However, kissing Teresa was perfectly acceptable, and unfortunately Terry still reminded me a lot of her, especially when he wore his new outfit. I know it sounds confusing, but that was how my mind was working then.
Anyway, after four weeks I noticed that his nails were still a little long and very neatly filed, his face and arms were still hairless, and I could swear his eyebrows were not growing back, as if they’d been regularly plucked! The problem was, I could think of no reason for him to be doing these things, and he refused to answer any questions I asked about it.
I finally learned the truth by accident. On Thursdays, Terry and I had lunch at the same time, and so we usually ate together in the school cafeteria. One Thursday, however, he was missing, and I wanted to know if he and his mother were alright. Since he was one of the few kids I knew who didn’t own a cell phone, after school I stopped at his house on my way home to see if everything was okay. That was when it all fell into place.
I was greeted at the door by Mrs. Jones. She was not looking at all well, but had enough strength to welcome me in. Then, I was surprised to hear her call out, “Teresa, Brian is here to see you.” Turning to me, Mrs. Jones added, “She is in the kitchen making some lunch for us. I am not having a good day today, I'm afraid, and Teresa stayed home to look after me. I told her she can't afford to miss too much school since it will hurt her grades, but she ignores me.”
I got up and walked to the kitchen, where I was shocked to find a stunning looking young woman standing there. She just wore a simple tee shirt over a matching skirt, with a pretty apron tied around her waist. The high heels, makeup and long, femininely-styled hair she wore added a sexy quality to her outfit. Despite being almost unrecognizable, I knew this beautiful teenage girl must be Terry!
“You…you weren't at school, and I…I thought something might be wrong,” I managed to stammer.
“Come, sit down and join us,” said Mrs. Jones to her feminized son.
Terry just stood there, however, looking horrified now. Finally, he blurted out, “Mother was not feeling well this morning, so I thought I would be of more use here than at school.” He failed to mentioned why he was dressed as Teresa, something I was dying to know.
“Would you like to join us?” his mother asked me politely.
“I don't think so. I had better be going if you are about to eat,” I said as I got up to leave.
“Be a good hostess and see your friend out, Teresa dear,” Mrs. Jones said with a smile.
We walked to the door, with Terry’s high heels clicking a staccato beat on the hardwood floor. There, I turned to look at my stricken friend and he begged, “Please don't tell anyone about this!”
“Of course not, but, why…?” I asked as I waved my hand over his feminine form.
“I dress like this to please mother,” he explained. “She really seems to do better when I dress and act like I’m her daughter, Theresa.”
Confused, I said something inane like, “that’s nice of you”, in reply.
“Please...keep this our secret!” Terry implored. As bad as his life at school had been since being officially declared the ‘prettiest boy’, he knew it would become a living hell if everyone learned he was still dressing as a girl at home.
Suddenly, I realized I could have my Teresa back! “OK. It will be our secret.....just you, me and your mother. But, you have to agree to act like you’re my girlfriend whenever you’re dressed up as Teresa!”
For a few seconds, Terry just stood looking at the floor. “Brian, please, you know I’m not really a girl. This is all pretend. You need a real girlfriend…”
“No, I don't! Not when I can have the one I really want, which is YOU! You will be my girlfriend, Terry, and with the way you look, no one will ever be the wiser!” I realized I had my friend over a barrel. He loved his mother and wanted to make her remaining time on earth as happy as possible, but I knew he was afraid of what pretending to be my girlfriend would surely lead to.
“Brian, please, what I did for you last time was just done out of gratitude. I meant nothing by it other then that.”
“But, I think you did! You didn’t have to kiss me, you didn’t need to act like such a good girlfriend, and you certainly didn’t need to give me a hand-job!”
Tears started appearing in Terry’s eyes. I put a hand on his shoulder to console him. “Sorry, I didn’t mean to upset you. I just want Teresa back in my life.”
He opened the front door and said, “Please go, Brian. I’ll see you at school tomorrow.”
I bent to give him a kiss, but he pulled away. So, I left with all sorts of things running through my mind. It all boiled down to, “Teresa is back!”, and, “How can I get her to accept me as her boyfriend?”

The next day at school I made sure I met up with Terry. He was in his tight jeans, salmon-colored shirt and black slip-ons with the little heel, plus there was a faint smell of flowers about him which I deduced was from some perfume. He eyed my warily, apparently concerned I might want to talk about the way he was dressed the previous afternoon.
“Your mother better today?” I wanted to come right out and demand that he go on a date with me as Teresa, but I decided to try a friendlier approach.
“Yes, thanks for asking.” Then, he added in a whisper, “I didn’t want you to find me like that yesterday, but for some reason it makes my mother feel better seeing me dressed up as a girl, and I do it all the time now when we’re both at home.”
“I didn’t mean to embarrass you. I came by because you were off from school again and I was concerned about you.”
“Thanks,” Terry replied, giving me a warm smile of gratitude.
“I can't deny I liked what I found though.”
“I knew you would. That’s why I didn’t want you to find out about my dressing up.”
“But now that I have, when can I see Teresa again?”
“Please, Brian, I only dress as a girl to make mother happy.”
“What about making me happy?”
“Please don't pressure me,” Terry begged, with desperation in his voice. “I had hoped the contest would be the last time I’d have to pretend to be a girl…” I could tell his strength was leaving him, so I decided to press on.
“But, it wasn't, and now Teresa is back, making her mother happy. So, why not just go with it and embrace your feminine side for a while?”
“And make your dreams come true also?” Terry said with a grim smile.
“Well, that too,” I admitted, red-faced.
“And if I…say no?” he asked hesitantly. I could almost see my friend’s resolve crumbling before me.
“If you say no, I will just keep coming to your house whenever I don't see you at school, because I’m sure to find you there being Teresa.”
“What if I refuse to see you?”
“I don’t think that will happen, since I know your secret and I’m certain you’ll want to stay on my good side to make sure it remains one!” I knew I was being harsh, but I realized I might only have this one chance at getting my girlfriend back, and I wanted to make the most of it.
“Please, don't do this,” he begged, as he started to tear up again.
I felt sorry for him, but I decided to go for the kill anyway. “And, keeping on my good side means becoming my steady girlfriend, and all that implies!” There, I said it. If Terry would not act as my loving girlfriend, he knew the whole school would quickly find out about his secret crossdressing.
I never thought of myself as a bad person, but I could see in his eyes that I had destroyed the boy I had grown up with. I knew this, but I didn’t care. I wanted Teresa, and so Terry would have to go.
“So, I’ll be seeing ‘Teresa’ soon?”
I swear Terry swallowed a sob. “I don't have a choice, do I?”
“Not really. See you later, Terri!” He looked startled, as if he could hear I was pronouncing his name with an “i”. And, from the look of defeat in his eyes, I knew I had my girlfriend back!

Terry made no effort to avoid me at school after that, and he acted in public as if everything was the same. But, we both knew our friendship had changed. We were no longer equal male buddies. Instead, in our relationship I was now in charge, and he would have to do my bidding. I know this made me something of a bully, but despite that I enjoyed the hold I now had over my friend.
For example, when I saw Terry the next day, he did not smell of anything besides clean. So, I subtly commented on how nice he had smelled the day before, and he blushed and promised to wear the scent for me next time. I wasn’t positive he would, but sure enough the next lunch I spent with him he smelled of the perfume again. When I asked what it was, he told me it was a small sample his mother had gotten as part of her beauty makeover. In her weakened state, the scent was a little too strong for her, so she had asked “Teresa” to wear it instead. I told him that when it ran out, he should let me buy him some more, rather than going back to his old male cologne. Rather meekly he agreed, and told me its name. The following Monday I gave him a bag with a bottle of “Desire” in it. He took it and said thank you with a shy smile, but to me what happened had much more significance. Terry was now wearing a woman’s perfume just to please me. Besides that, he had accepted my feminine gift just like a girl would from her boyfriend!
I had a plan not to rush Terry into things, since he could always call my bluff and walk away. So, for a while, I left this stage of his feminization at just the perfume. But, I also made sure to compliment him on his appearance if he wore anything vaguely feminine to school.
Then, when he finally missed a day, I made sure to call at his house on my way home. The door opened with “Teresa” hiding behind it, hoping no one outside would see him.
“Everything ok?” I asked as I walked in, staring appreciatively at my lovely girlfriend.
“Mother is not good at all,” he said, with obvious concern in his voice.
“I’m sorry to hear that.”
Then from the living room I heard a weak voice ask, “Who is it, Teresa?”
“Only Brian.”
“Come in Brian. How are you, dear?” she asked politely.
“Oh, I’m fine, thanks. It’s just that Teresa was not at school today, and I was worried.”
“That's sweet of you, but I am afraid it is me who is not doing well. I’m such a burden on my lovely daughter…”
Terry stepped to her side. “I don't mind at all, mother, you know that.”
I asked if there was anything I could do to help, and promised to call whenever I could. When Terry showed me to the door I couldn’t resist saying, “That top looks terrific on you!” It was the blue tight-fitting shirt he had on when I first saw him as ‘Teresa’.
“Do you have to say things like that?” he asked. “It’s very embarrassing.”
“I can’t help it. I always like seeing it on you because it really shows off your breasts and looks dead sexy!” That compliment just brought a disgusted look to Terry’s face. Still, I decided to take a chance and asked, “Do I get a goodbye kiss from my girl?”
When Terry made no attempt to kiss me, I put a hand under his chin and lifted it up until I could kiss those pink lips that tasted of strawberries. “See you tomorrow at school?”
“If mother is better.”
I kissed him once more, even more forcefully, and then left. I was elated! I was back to kissing my girlfriend, after thinking my chances of even seeing her again had died a few weeks earlier. Now, invigorated by that mild sexual contact, I knew I would want more. Even if the relationship was very one-sided.

That weekend I bought a another gift for Terry. The ear piercings had healed up well, but he only had plain studs to wear. So, I bought him some more earrings, this time with a ruby stone in them! I gave them to him on the Monday.
“Should I be grateful?” he said as he opened the box.
“A ‘thank you’ would be nice.”
“Thank you,” he said without emotion as he stared at the feminine earrings.
“I thought they would make a nice change to those plain ones you always have on.”
“I can hardly wear my mother's long dangling earrings to school, can I?” he answered sarcastically.
I gave him a grin. “Why not...I’m sure they would look lovely on you! Anyway, these are nice and discrete.”
“But, obviously a girl's earrings.”
“Yes, that as well, which we both know is why I got them for you.”
“And you want me to wear them to class?”
“Of course. They would go well with the red t-shirt your mother likes you to wear.”
Terry let out a big sigh and asked me how Mary was now that she had left home. He was trying to change the subject, but I didn’t object since I knew I had won another battle in my efforts to feminize him.

When I met up with Terry the next day, I could see under his hoodie the red top and his new red stud earrings. I pulled the hood back to get a better look, and as a tease I said, “Maybe I should have gotten a larger stud…”
He replied immediately, “No! These are fine just as they are, thanks.”
“So, you won’t mind wearing them all the time for me?”
He nearly said something in defiance, but backed down and just mumbled, “I guess.” The next day I was pleased to see the studs were still in their place, making his small ears look even prettier.

My next move was to visit Terry at home on a weekend. At first, I couldn’t think of an excuse to stop by, but then I thought, ‘Who needs an excuse to see their girlfriend?’ So, I just turned up on Saturday around 7 PM. Terry looked shocked when he opened the door. As I had hoped, he was completely dressed and made up as Teresa!
I was quickly ushered in and went through the usual polite “how are you’s” with Mrs. Jones. She invited me to join them in watching some TV, and insisted I sit with her ‘daughter’ on the sofa. As Terry slid over to make room for me, I took in the full picture of my boyhood friend. He was wearing a tight-fitting pink silk dress, pink lace-top stockings and his black stiletto heels. I noted with excitement that I could see a little of his white lace bra peeking out!
As we watched a movie that could be best described as a ‘chick-flick’, his mother said, “Those pretty earrings you bought for Teresa are so nice. She never has them out of her ears now, she likes them that much!” I could tell that Terry was about to give a rebuttal, so I interrupted him.
“I just wanted to give your daughter a gift, so she doesn't feel neglected by her boyfriend!”
“How very thoughtful of you, Brian!”
When the movie was over, Mrs. Jones got up and said, “If you young people don't mind, I’m feeling tired, so I think I’ll head off to bed.”
It was only eight o’clock, but I just assumed that her illness made her tire out more quickly. That is, until she leaned over to give me a goodnight kiss on the cheek and whispered, “Have fun, you lovebirds!”
As Terry went with his mother to help with whatever she needed, I considered what I had just learned. Not only did Mrs. Jones know that her son and I were intimate, she actually seemed to want to encourage it! I wasn’t sure why this was, but I guessed it had something to do with her wanting Terry to not only accept being her daughter, but to enjoy himself as Teresa also.
While I waited, I amused myself channel-hoping until I found a fashion show which I thought might be a good tease for when Terry returned. When he finally showed up fifteen minutes later, he started to sit in one of the chairs, but I quickly patted the space next to me on the sofa to remind him that this was where my ‘girlfriend’ belonged. Then, with my arm around his shoulders and my hand resting on his nylon-covered thigh, we watched the fashion show.
Terry seemed a little stiff at first, especially when I made comments on how I though each dress might look on him. But as the evening went on, he seemed to loosen up and even snuggle a little closer to me. I thought this made a for a nice first night in with my new girlfriend, so I didn’t try to take things any further for fear of scaring him off. Whether Terry was cuddling up to me to get on my good side, or because he really wanted to, I wasn’t sure. But I was content with the progress I was making, especially after the goodnight kiss I gave, which ‘Teresa’ seemed to reciprocate!
I visited every Saturday evening for the next three weeks, and the same pattern followed: polite chat, Mrs. Jones going to bed early, and cuddling with my girlfriend. By the third week we had moved on from a goodbye kiss at the door to kissing in the living room! I got the happy feeling that Terry was gradually growing more accepting of his new role as my girlfriend. What happened next took me by surprise, but actually helped further my grand scheme.
As usual I came to visit on Saturday, but this time when Mrs. Jones sent Terry to make her a hot drink, she conspiratorially leaned towards me.
“Brian, you seem to be having a nice softening effect on Teresa.” I looked at her questioningly. “You know, the earrings, the perfume, and especially what you two do when I go to bed!”
“Oh?” I said, trying to appear confused.
“Don’t act so innocent,” she said with a knowing smile. “I might be sick, but I still see and hear what is going on!” Then, she put her frail hand on my arm and continued.
“I want to ask you a favor. Sometimes I still find the toilet seat up after Teresa has done her business. I remembered that dress she wore to the contest was so low cut at the back that she could not have been wearing panties, am I right?” She didn’t wait for an answer. “So, the floppy bit between her legs must have been tucked away somehow. Now, what I am asking you is, can you persuade her to do that all the time? It is not nice thinking of her standing up to relieve herself like a boy, but if she has her thingy safely tucked away, then she’d have to sit like a normal female to relieve herself.”
“Well, I guess I could have a word with her about it,” I said nonchalantly, while inside I was jumping for joy at being given the lead-in to the next step in Terry’s feminization!
Just as Mrs. Jones finished, her ‘daughter’ walked in with a tea for her, a beer for me and a lemonade for herself. No mention was made of the previous subject, and we discussed some item on the TV instead.
Later that evening, I was cuddling with Terry as usual, waiting for just the right time to bring up what his mother had asked. Finally, he excused himself to use the bathroom, and I blurted out, “Your mom doesn't like you standing up to pee!” This got a swift reaction.
“You’ve been talking with mother about me?”
“No, it’s not what you think. When you were out of the room, she told me that she really likes having a daughter around, but when you leave the seat up it ruins the illusion. Couldn’t you just fix yourself up like you did for the pageant?”
Terry calmed down a bit and explained, “It takes a lot of effort to get myself all taped up…and it’s very uncomfortable to undo it later.”
“Well then, why not do it once and keep it that way all the time? Then, you would always have to sit when using the bathroom, and you’d never have to worry about forgetting and upsetting your mother. Problem solved!”
“You are serious about this, aren't you?” Terry asked with surprise.
“Of course! Plus, it’ll give you a nice flat crotch for your tight outfits as well.”
“And if I say no?”
“Let's not go down that road again. Look, why not do it just to please your mother?”
Terry turned away from me, deep in thought. I knew he realized that if he did what I asked, he would essentially be giving himself a sex-change, only seeing his manhood for occasional needed bathing. Finally, he just shrugged his shoulders and replied, “Would you like another beer?”
“Yes, thanks.” That was the end of the discussion. Time would tell if I had won another round in the battle to change my boyhood buddy into my dream girlfriend.

Come Monday, I was not sure what to expect, since Terry had been quite cold after the talk of toilet ettiquete. So imagine how I felt when I saw him walking towards me, with his tight jeans showing no sign of male organs, just a flat V creasing into the tops of his legs!
“Have you told your mother what you’re doing?” I asked, barely able to restrain my glee.
“No, I just walked around in front of her a few times wearing snug-fitting panties, so she could see I had complied with your wishes.”
“You know this must please her a lot, since she loves seeing you as her daughter.”
“I know, and I love my mother and want her final days to be as happy as possible. But, she’s certainly not making this easy for me…”
“Maybe not, but I appreciate your efforts as well,” I said, giving his hand a quick squeeze. To my great surprise, Terry smiled and squeezed back!

Later that week, I bought him another gift from the boutique where we got the jeans. I found the same assistant, and though he was disappointed I was on my own, when I said I wanted something for my friend he knew exactly who I meant. With his help I bought Terry another pair of women’s pants, this time in white, which were just as tight as the others. On Saturday I took them with me and presented them to my girlfriend. Mrs. Jones was more thrilled by the gift than Terry, but I didn’t care. With two pairs of tight pants he would be displaying his flat front all the time at school now, so I could enjoy my girlfriend’s feminine appearance even there!

The final exams of the year were upon us, and I ended up doing quite well. Unfortunately, Terry didn’t, I guessed because he wasn’t able to put in the needed work. It never crossed my mind that I might be partly to blame for his poor results! I assumed it was due to the fact that he was spending so much time caring for his mother, and not anything resulting from him not being able to concentrate due to worrying about having to appear at school looking more feminine with each passing day.
At least things progressed quite well on the Saturday night front. I no longer had to prompt special behavior in Terry. He automatically snuggled close to me, even in his mother's presence, gave me kisses without being asked, and in general acted like the female in our relationship. All of this was nice, but I still wanted more.
The next stage came when I got my own car. This meant I could take Terry out on real dates. Naturally, I wanted him to come with me dressed in a sexy top, short skirt and high heels, but he wasn’t ready for that yet. So, the first time I took him out in my new car, we compromised. He wore his tight jeans, a hoodie jacket, and his shoes with the little heels, but this was on the condition that one item would be exchanged for something more overtly feminine the next time. So, after just a few weeks it reached the point where I was taking Terry out with him completely dressed as a sexy young woman! At last I had my boyhood buddy back to where he’d been at the time of the beauty pageant. I was proud to once again be able to take my pretty girlfriend Teresa out to eat or see a show.

The next big change in Terry’s life was bound to happen sooner or later. His neighbors finally found out that the teenage boy was essentially living as a young woman when not at school! One happened to call unexpectedly, and without knocking let herself in shouting, “It’s only me.” Before Terry could hide upstairs he was spotted. At first, the woman did not recognize who the new pretty girl was. But then, when she finally realized it was Terry in drag, Mrs. Jones told her some story about how her son thought he might be transgendered, and he was living as a girl part time to find out if the female life was truly right for him.
Apparently the woman bought this, saying, “As if you haven't enough to cope with already…” But, the damage had been done, and the nosey neighbor quickly told everyone she knew about it. I suddenly had no power over Terry, since his dressing as a girl soon became common knowledge. Surprisingly, it did not change our relationship. If anything, it even lowered his resistance to being seen out in public as Teresa, since he now had the attitude, “What the heck, let them have an eyeful!”
From that point on, I was able to take Terry out his front door, with him proudly displaying his beautifully made up face, womanly chest, and nylon-covered legs ending in sexy skyscraper heels! It had taken a few months, but we were finally getting close to where I wanted to be, despite my ‘girlfriend’ not being in favor of most of the changes along the way.
That summer things were great for me, since I now had the freedom to go out in public with my new ‘girlfriend’ to enjoy the long romantic evenings together, and also the opportunity to take Terry out shopping for sexy new clothes to wear for me! What made it even more perfect was what happened with my family.
First, Mary cornered me into admitting that I was going out with ‘Teresa’ again, after I had been seen by some of her friends with an attractive girl who met her description. Then, I was allowed to skip the annual family vacation and remain home with my sister, who was much more relaxed about my dating a boy than my parents would have been. This freedom allowed me to manipulate some interesting events in Terry's life.
The first thing I did was turn up early the next time Mrs. Jones invited me to join her and her daughter for dinner. Then, while Terry was cooking and his mother was watching TV, I went upstairs, supposedly to use the toilet, but with the real purpose of getting a look at my boyhood friend's room. I had not seen it since the contest, and I suspected it looked very different now.
Once inside I found I was right…the place appeared more like my sister’s bedroom than a teenage boy’s, with makeup and lingerie everywhere! Interestingly, I couldn’t find anything of Terry's…all his male stuff must have been stored away. It pleased me to see his room looking so feminine, and I went back downstairs satisfied that Terry was indeed living full time as a girl.
That evening I drank too many beers on purpose, hoping my hosts would realized I shouldn’t drive home in my condition. Fortunately, Mrs. Jones did insist I spend the night, and with no parents to convince, I quickly accepted.
I slept on the living room sofa, which allowed me to wake up the next morning to the wonderful sight of Terry, dressed in a sexy red and white polka-dot top with a matching ribbon tied in his hair, a tight black skirt and tall, stiletto-heeled pumps, bringing our breakfast to the kitchen table! I imagined that he was my wife and did this for me every day before I went off to work, which pleased me greatly. The most exciting part though was seeing that his fake tits were still in place and his hair was fixed up in the same feminine style from the night before, which meant that Terry looked like a girl even while sleeping!
When he called from the kitchen and asked me what I wanted with my meal, I replied, “You!”
“Don't say that, mother might hear you!” Terry whispered as he walked up to me with sexy sway to his hips caused by his tight skirt and the towering heels on his feet.
I reached under the skirt and stroked his satin covered bottom as I said, “Your mother is still taking her bath, and I would love to have you right now!” Then, several things happened unexpectedly. First, Terry sat on my lap and put an arm round my neck.
“Like this?” he asked with a coy smile as he brought his face up to mine and gave me a kiss!
There must have been something about the sexy outfit he was wearing, because Terry seemed more passionate with his kissing than I could remember. After what seemed like an age, we broke for air.
“How about we go back to my place after your mother has been fed so we can have more privacy?” I asked, hoping to take full advantage of Terry’s unusually amorous state. To my surprise I got an enthusiastic 'yes'! An hour later, a very pretty and sexily dressed Teresa sat beside me as we drove to my house. As I had expected, Mary was at work, so we had the place to ourselves.
“You want me, so here I am,” Terry said submissively as he sat on the sofa.
Now that I had the ‘girl’ of my dreams ready and willing to have sex, I was unsure what to do. I started with kissing, then fumbling inside his clothes. In the end Terry undid his blouse, removed his bra and lowered his skirt. He now stood in front of me in just panties and heels. What a sight!
“Could I make love to you?” I asked tentatively.
“I…I guess. But, how could we do it?” Terry asked with confusion. “I mean, you know what I really have underneath my panties…”
“I’ve been reading on the internet about a way we can have sex by using your ‘backdoor vagina’,” I said hesitantly. Terry was puzzled at first by what I was suggesting, but when I showed him a picture I had downloaded from a website that featured transsexuals having sex with men, his eyes opened as wide as saucers!
I decided to act quickly, before my lovely girlfriend could change her mind. So, I immediately rolled Terry over on his stomach and pulled his panties off. When it comes down to it, getting a stiff penis into a tight hole is not easy, but there was some KY jelly in the bathroom, and with patience I eventually found myself deep inside his bottom!
Terry groaned with discomfort and gritted his teeth as I penetrated him, but that gradually subsided. Then, as I began a slow and steady in and out action, I noticed the groaning turned into a moaning, not of pain but of pleasure! In no time he was pushing his behind against my groin with each thrust I made, and soon we were both writhing in passion. Suddenly, I tensed up and then exploded with a mind-shattering orgasm, filling my girlfriend’s bottom with my seed!
Goodness knows what inspired him, but as I lay there recovering Terry licked my penis clean! As he did so, my erection started to return. My girl saw this and responded by giving me an amazing blow job! Wow, what a turn around! Terry had gone from being a teenage boy who resisted my every effort to feminize him, and had become the sex-crazed girl of my dreams!
“Did my man like that?” he asked as he sensuously licked some of my cum off his fingers.
“How can I say no?” I replied in amazement. Then I added, “What brought that on?”.
“I’m not sure,” he admitted sheepishly, “but seeing you in your boxers this morning, looking so manly, just seemed to turn me on. I suddenly felt like I had to do something to make you happy.”
“Well, you certainly have succeeded there!” I said with a grin.
“I also got to be your first, which must mean something,” Terry said wistfully.
“Yes, it does…that I love you!” I said sincerely.
“Now, don't get carried away just because you’ve had sex with me,” my girlfriend admonished.
“But, I’m not being carried away, Teresa. Ever since the contest, I’ve been in love with you!”
Terry’s expression turned serious as he thought about what I said. Finally, he asked, “Why didn't you say that in the first place, instead of forcing me to become your girlfriend?”
“I couldn't be sure you would accept me,” I explained, feeling more guilty than ever about my actions.
Before Terry could reply, our peace was broken by the front door opening. It was Mary coming home for lunch! I immediately grabbed my girl’s arm and dragged her up to my room and locked the door. Finally, we could relax. That is, until she suddenly realized, “My clothes are still downstairs!”
“OMG, stay here!” I left my love on my bed and dressed quickly before going to the stairs.
“Hi brother, is it safe to come up?” Mary asked with a knowing smile. I could see she was carrying the evidence in her hands! I ran downstairs, took Teresa’s clothes from her, and returned to my room. “You two must really be in love to be at it this early in the day!” I heard her tease as I shut my door.
I was flustered and threw the clothes on the bed, but Terry was the one teasing me now. 'What's the rush… don’t you want me anymore?” he said and gave me a fake hurt expression.
“Hurry and get dressed, and then I’ll run you home!” I demanded.
Terry did get dressed, but waiting in the kitchen for us was Mary. We didn’t have to go out that way, but ‘Teresa’ made a point of going in to say hello. Mary seemed unfazed at seeing my boyhood friend looking like a beautiful young woman who had just been well and truly fucked, which was actually the case! At the same time, Terry appeared totally relaxed as he sat down and casually had a chat with her, I think to make me squirm. And he succeeded!
We didn’t leave till late afternoon, by which time Terry and Mary had discussed everything about the re-invention of Teresa, and even where things might go from there. For the first time I felt that my new girlfriend might have gotten the upper hand in our relationship, and with Mary now in on it, my life could be become extremely difficult.
After that, my sister did indeed enjoy teasing me about my sexy new girlfriend, but not so much because it was actually Terry, who we both knew was not a real female, but more at the idea that I had a girlfriend, period, and had been so secretive about it. Pretty much normal behavior for siblings I suppose.
Terry, however, began taking advantage of the fact that he had the power to manipulate me now. Like the day he came over and made me promise to take him shopping for a new sundress and matching heels before he would satisfy my carnal lust! Not that I minded; he looked lovely in the cotton print dress with a yellow ribbon sash he picked out, which I encouraged him to wear off the shoulder to reveal as much skin as possible! And the new tall, wedge sandals I also paid for revealed his pretty painted toenails, as well as adding an extra wiggle to his already sexy walk!
By the time my parents had returned from their holiday, I think Terry and I had had anal sex five times, and I had gotten several blow jobs from him too! Looking back, we were not very good with our sexual positioning at first, but I did some research on the internet, and by our third session Terry was properly on his back with his high heel tipped legs high in the air. This gave me better access to his rear opening, and in this position I was able to control myself better so I could pump away for what seemed like hours! I also loved the way his glue-on breasts looked so enticing this way, as they sat up firmly on his formerly flat boy’s chest. Then, just as I was about to climax, Terry tensed, arched his back, and came right along with me! I was totally pleased with myself that I had made my boyhood friend come like a woman. And from the expression on his face, I could tell he was happy too. The pendulum had swung back towards me after that, as sex was not just about my pleasure anymore. From then on, I always did my best to make sure that Terry was taken care of as well…that is, if he was a good girl!

After my parents returned, there were not many opportunities left during the summer holidays for Terry and I to have sex at my home. We had a couple of daytime encounters, but my summer job got in the way as much as my family members did.
We did have one last night alone before classes resumed. Fortunately, my parents had plans for the evening, and Mary agreed to hang out with some friends, “so you two horny teens can get your rocks off in private!” Since Terry couldn’t dress up as a girl for school, I decided I would have him be a “schoolgirl” for me at home! I borrowed a costume my sister had worn to a Halloween party, and had him wear his wig in pigtails and not too much makeup, to look more virginal. It was a typical schoolgirl outfit, with a plaid skirt and matching tie, along with a white blouse and knee socks. It wasn’t tight fitting, but ever so sexy…the almost 5” heels on his feet made sure of that! The best part was that aside from some panties, the outfit offered no barrier for sex, as the short skirt flipped up easily, allowing me complete access to my beautiful girlfriend’s ‘vagina’! And, with the house free, I planned to take advantage of the dress’s easy access several times that night!
With that in mind, I had Terry start me out with a blow-job. I did this since I knew it would make it easier to keep from cumming too fast later when we got down to the main event…anal sex! And so, I sat back and enjoyed his lips, tongue and hands caress my manhood. It didn’t take long before I let out with a groan and filled “Teresa’s” mouth with a copious amount of my seed!
While I recovered from the mind-shattering orgasm, I couldn’t help but think how much Terry had changed in just a short time. Once, he was my boyhood pal, but now not only was he my girlfriend, but my lover as well! Just thinking of this helped me to quickly become horny again.
I rolled Terry over and flipped up his short skirt and pulled aside his thong panties, allowing me easy access to my lover’s bottom. Then, I grabbed his ponytail and rammed myself deep inside his ‘boy pussy’! Even though we had had sex this way several times before, I could tell Terry still felt some initial discomfort by the pained expression on his face. However, as always, that quickly went away, and was eventually replaced by a look of sheer bliss! In no time, both of us reached an earth-shaking orgasm, followed by a cuddle in each other’s arms.
We lay that way for a while, until our teenage urges returned and we went at it again. We must have had sex three or four times before it got too close to when my parents were expected home and we had to stop. Still, it was truly a night to remember.
Sadly, on Monday Teresa had to disappear so Terry could attend classes without too much of a hassle. And so, gone was the long hair and the breasts; the heels and makeup were missing as well. I knew I couldn’t push him to dress as Teresa to attend classes, so I had to accept that while in school I would have to put up with my girlfriend looking slightly masculine in jeans and shirts. Even if those jeans required the wearing of panties to avoid bulky underwear lines, and the shirts had a definite feminine edge to them! Terry continued wearing the red jeweled earrings all the time, and when I bought some larger pink ones, he resisted only slightly and then gave in and wore them too.
Mrs. Jones was aware that I wanted her son to become as much of a woman as possible, and I felt sure she wanted the same thing. The toilet seat incident and the transgender story she told her neighbor bore this out. However, even I wasn’t totally aware of all she was doing to change her child. Frail and sick Mrs. Jones might have been, but feeble-minded she was not. It was she who made space for us to spend time together early on. It was also she who first encouraged me to take her ‘daughter’ out on dates. And mainly, it was she who had kept Terry dressing as a girl after the pageant was over. But, what I discovered that autumn completely shocked me.
One time when I was visiting my girlfriend, I learned that Mrs Jones would be needing to spend a few days in the hospital. Before she went in, she took me aside and asked if when I came around to ‘have some fun’ with her daughter, could I make sure Teresa took her medication? She went on to explain how once a day since Terry entered the womanless pageant she made a drink for him, usually tea or cocoa, and dissolved a tablet in the hot liquid. When I asked why not just give it as a pill, Mrs. Jones said it was better if Teresa didn’t know what she was taking, since if she did it might disturb her. I took this to mean the medicine was some sort of nerve-calming prescription, and I quickly agreed to see that she got it whenever her mother was away.
A week later, I was enjoying the freedom of Terry's house with Mrs. Jones gone. After we had our usual round of sex and my girl was in the bathroom cleaning up, I went into the kitchen and made her some hot cocoa which included the pill. Mrs Jones was having a series of treatments, which meant she would be in the hospital for a couple of days over several weeks. I did my best during those times to make sure Terry got his medicine.
It wasn’t until about the third time I was preparing the pill-laced drink that curiosity got the better of me, and I made note of the medicine’s name and looked it up on the internet. To my great shock I found out that Mrs Jones was giving Terry female hormones! I assumed they were originally perscribed for her, but she had decided they would be better used to make her son more feminine.
When I read up on the effects of the pills, I recognised things in Terry that at the time had seemed odd, but now made perfect sense. For example, his voice had never broken, and while I had to shave every day, he still had no sign of a beard on his face. Also, his body seemed soft and without any definition, while mine had become much harder and more muscled.
There were also other, less objective things about Terry that I noticed, like his personality seeming much less aggressive than before, the fact that he could now cry at the drop of a hat, and especially his being turned on by my masculine appearance! All of these changes I now attributed to the female hormones he was unknowingly taking.
And so, to my great delight, Mrs. Jones had begun the next big step in Terry’s feminization, one I hadn’t dared to initiate on my own. Armed with this information, I made it my point to see that Teresa got her daily hormone pill without fail. When I told Mrs Jones the next time we were alone that I knew what she was giving her son, she was at first concerned that I might object to this. I quickly assured her that I was in complete agreement with what she was doing. Further, I had done some research on transgendered boys who were taking hormones, and had concluded that Terry’s body could stand an even higher doseage, which would cause it show feminine improvements much faster!
Mrs. Jones was thrilled to hear this, and she decided that since she had plenty of pills to spare, we would increase the number her daughter was given to three a day! And so, Terry began taking triple the amount of female hormones as before, and the results were noticable in just a few months!
I knew this because when I asked him what he would like for Christmas, Terry mentioned some new jeans, because for some reason, the old ones were getting loose in the waist but tighter around the hips and buttocks. Sure enough, when I took a descrete but careful look at my girlfriend’s behind, it was indeed more full, rounded and womanly in appearance!
Even more exciting to me was something that I noticed about Terry’s chest one day at school when he wore a tight t-shirt. It was obvious from the way the front was pushed out by two small mounds that his shape was changing there too! At first I teased him by asking if he’d been working out. When he asked why, I pointed to his developing pectorals and touched one, which made him flinch.
“Tender?” I asked innocently.
“Very!” was the reply. The next time we were alone in his bedroom, I asked Terry to remove his bra and falsies so I could get a better look at this latest change. Sure enough, his normally flat boy’s chest now featured the small mounds of a young girl just beginning to develop breasts! Mrs. Jones was delighted when I told her about these observations, and I suspect she increased the hormone dosage even further after that, since Terry reported his chest seemed much more swollen and tender in the coming weeks!
By Christmas, I had come clean with my parents about my love for Teresa. At first they were extremely skeptical about such a relationship. They had seen my girlfriend growing up as a boy named Terry, and they felt there was no future with a person, no matter how pretty, who demonstrated such obvious sexual confusion. I quickly reassured them that the former boy was handling his change of gender well, and that he looked even more realistic and natural now than at the contest. Finally, it was decided that I could invite Teresa to visit over the Christmas break.
As it turned out, my parents were as taken with the beautiful and feminine creature I had created as I was. In fact, after my mother got to know Teresa better, she invited her and her mother over to join us for dinner on New Year’s Day, which made Mrs. Jones as happy as I’d seen her in the last few months.

As Terry got better known around town as a transgendered boy, his freedom to be publicly feminine grew. However, for school he had to maintain a somewhat boyish appearance, and I counted the days until we graduated and Teresa could be a full-time female.
The hormones continued to do their work, and by Easter the small mounds of Christmas had grown into actual breasts, preventing Terry from wearing any tight-fitting top to school for fear of becoming even more of an object of ridicule. Naturally, he worried about the changes to his body, and even asked his mother to take him to see a doctor. But Mrs. Jones explained honestly that they didn’t have the money to do so, and then she pointed out that she’d seen some boys develop small breasts right before they were about to begin puberty. Hearing that, Terry felt relieved. He had wondered when his body would start becoming more masculine and hairy like the other guys his age, and now he had hope that the time would be soon. Little did he know that the changes he was hoping for would never happen!
In the meantime, I tried to make Terry more accepting of his new feminine attributes. Whenever we made love, I always took care to gently fondle his breasts and squeeze his swollen nipples, showing him how pleasurable they could be. When he got used to that, I moved on to licking and sucking on them, which soon had my girlfriend begging for more!
Using this tactic, Terry began to expect and enjoy my playing with his breasts as a part of any sexual encounter we had. He especially grew to love my hands on his growing mammary glands whenever we had anal sex, and he would cry out for me to squeeze and pinch them as I pounded his behind with my engorged organ!
By the end of the school year, I knew I had done well enough in my courses to graduate and get a good job. For Terry, it was completely different. He failed all but one course, home economics, but there was no way he could redo his senior year now that his body had changed to the point where he needed to wear a bra at all times to support his growing breasts! So, he never went back to school after that, and just stayed at home and looked after his mother instead.
Over the course of the summer, to my great delight, Terry’s chest developed to the point that he completely filled his old bras. Also, his expanding bottom looked even more sexy as it jiggled in over-tight jeans and skirts. During this time our relationship seemed to settle down to one of an established couple. With my good-paying job and still living at home, I had plenty of money, so I regularly gave Terry expensive gifts, either to wear for me or in some other fashion make himself look even more feminine and sexy.
While I was generally enjoying myself, things weren’t going as well for Mrs. Jones. And then, early in the fall, she lost her fight to live. It was a sad day when I escorted her beloved ‘daughter’ to the funeral. My dad had been very good and arranged everything, but I remember a hard discussion between Terry and my mother about whether he should go to the funeral as the boy he was born or the girl he had become. He wanted to do the former, since relatives would be there who would be confused by his new feminine appearance.
My mother resolved the problem by taking Terry to a full length mirror and asking him what he saw. He had to admit it was a woman. “So how could a woman go dressed as a boy and not look odd?” she asked. “Let those others who never bothered to visit while your mother was sick think whatever they want to. Their opinion isn’t worth as much as their help during the past few years would’ve been.”
And so, Terry went to the funeral as Teresa. My mother took him out the day before and bought him a nice black dress to wear. It was tasteful, but low cut enough to show off his now impressive cleavage. While some at the funeral were confused about who was leading the mourners, no one guessed that the weeping person was anything but an attractive young woman.

After his mother was laid to rest, Terry felt lost with no one to care for and no school or work to go to. He sat at home and tried to consider his future. I was over there a lot, though not for any pleasure of my own. Rather, I was just looking out for someone I loved dearly.
Often, I would find Terry sobbing over the loss of his mother. And, on one occasion I found him standing naked in front of a mirror, staring at himself and questioning what had become of the boy he once was. I knew then it was time to act. Terry’s grief would surely lessen over time, but his doubts about being anything but a girl, my girl, I could not allow to grow!
And so, insisting that he shouldn’t mope around any longer, I took Terry to a salon and arranged for him have a complete make-over. I told the beautician to give my girlfriend ‘the works’! I was told to come back in four hours, which I thought was a little long, but I agreed. When I returned and Terry was finally finished with his make-over, I was amazed at the difference!
I was used to the wig he always wore, but that was gone. Terry’s own hair had apparently grown rapidly from the female hormones, and had been fashioned into a totally feminine style. His eyes had lash extensions, making them extra long and silky, his brows altered permanently into pencil-thin high arches through electrolysis, his lips plumped with collagen, and after many failed attempts to get him to grow more feminine-looking nails, he now sported long acrylic nails painted bright red!
I was a lot poorer, but extremely pleased that I had talked Terry into doing this. It really made a big difference in his personally. And when we got home afterwards, for the first time since his loss we had sex! I even had the nail marks on my back to prove it, though I wasn’t complaining.

My father offered to help sort out Terry’s finances, and it quickly became clear that he had no income at all now that the medical assistance and pensions were gone. He did inherit the house, and if he went back to finish school he could get extra support while studying, but it would not be much. So, I offered to help by moving in with him and sharing the costs. This was viewed differently by everyone. My dad thought I was a fool, my mother thought me generous, and my sister thought I was after sex! I think maybe all three were right.
Terry did not really get a say in the matter. I still saw him as my girl, and so I was the boss. So, I just moved in. He didn’t complain, though, about my unilateral decision, because besides helping him financially, it also gave him someone to look after and a purpose to doing things about the house, which helped heal the grief over losing his mother. For my part, I was thrilled that I now got to see “Teresa” every evening, which was a delight since I have always loved Terry in sexy nightgowns, of which I made sure he had plenty!
A few things had to change though. Terry was uncomfortable sleeping in his mothers double bed, and his single was too small for the two of us. So we redecorated his room and bought a new bedroom set. But in the choosing of colors, I could tell he was undecided between pinks and flowers versus darker greys and more masculine designs. I was disappointed to see that despite my imposed femininity all these many months, Terry still had a part of himself which yearned to return to manhood.
My solution was to take him out and get his navel pierced and fitted with a medalion that had 'Brian's Girl' written on it! I made sure the belly ring was impossible to remove without a special key which only I had, so Terry would have a permanent reminder of who he now was. After that, we returned to the decorators, and a week later Terry had pink walls, lacy curtains and a canopy bed! The former boy’s bedroom looked very feminine now, and totally Teresa’s. When we christened the bed that night, I loved seeing Terry wearing the new navel jewelry, telling all the world that he was my girlfriend!
Without any new pills from Mrs. Jones, I eventually ran out of hormones. I decided to take a bold step and come clean with Terry about what his mother had done. I defended her by saying that she started giving him her female hormone medicine because she wanted her daughter to have a beautiful figure to go along with her lovely face.
Terry was shocked and angry at first over what his mother had done to him. Then, he calmed down and actually felt relieved that he now understood why his body had become so feminine looking. He had thought he might have testicular cancer, which was blocking his male hormones and causing the changes, so at least he didn’t have to worry about that any more.
Then, he put his head on my shoulder and began to sob, crying out that he forgave his mother since what she had done just made it easier for her to enjoy the daughter she always wanted for her final few months of life. In his weakened emotional state, it was easy to convince Terry to see a transgender specialist named Dr. Mills, who after hearing how long the teenage boy had been living as a woman, promptly put him on a proper regime of female hormones and testosterone blockers to insure he continued his feminine development.
During our visit with the specialist, the subject of eventual sex reassignment surgery came up, but Terry wouldn’t hear of it. I spoke to the doctor in private and explained that ‘Teresa’ was still recovering from the loss of her mother, but I assured the surgeon that she had expressed many times before Mrs. Jones’ passing that her ultimate goal was to become a woman so she could marry me. The specialist understood and said that the surgery could be scheduled at some future date whenever Teresa was ready.
As we left Dr. Mill’s office, I was dancing on air! My ultimate goal of turning my boyhood friend into a complete woman was within my grasp. Now, I just had to find some way of convincing Terry to agree to having his sex permanently changed!

Things went along well after that. I got a nice promotion and increase in salary at my job, and Terry went back to school and finally graduated. When he was ready to look for work, he thought about doing it as a male, since his ID’s all showed him to be one. However, I found a job for him that didn’t require an ID and would pay him ‘under the table’, so there was no need to report wages to social security. It was in an assisted living home for the elderly, something Terry knew how to do quite well. So, to their and my delight, the residents of Golden Acres soon had a pretty new assistant named Teresa to help them!

There was one potential problem on the horizon. The transgender doctor had insisted on Terry having counseling to ensure that becoming a female was what he truly wanted. Naturally, I worried that it might undo all the mental and emotional feminizing I had done to him up till then. And so, before and after each counseling session, I made sure we had sex, taking particular care to see that Terry had a mind-blowing orgasm each time! It must have worked, because the doctor told me that ‘Teresa’ never expressed the need to be a boy again.
Despite this, the subject of sex change surgery was still forbidden at home. As time past, Terry and I stayed as boyfriend and girlfriend, while I had to watch as most of my friends got married. This irked me, because as two males we could not be joined in wedded bliss. So, I hatched another plan.
First, I convinced my family to go with us on a joint ski vacation. I had done my research and the hotel we were staying at would be hosting a ‘womanless’ wedding! Terry knew nothing of this until we got there and saw the posters and preparations for this event. I 'innocently' suggested we could volunteer to participate, because technically he was still a male. Terry was reluctant, remembering what happened the last time he entered a ‘womanless’ event!
Mary did her best to convince him that it would be fun to go shopping for a wedding gown together if he was chosen to be the bride, but he still hesitated. In the end, what made Terry agreed to sign up was my pointing out that we probably wouldn’t be selected anyway, since we were not local people. Little did he know that I had arranged with the sponsors beforehand that I would provide our wedding clothes for free if we were chosen to be the bride and groom!
And so, we signed up for the event. It was amusing to see Terry try and dress up like a boy, binding his breasts, covering his long hair with a cap and wearing loose fitting unisex clothes to hide his narrow waist and wide hips, all to no avail. He still looked every bit as feminine as any real girl would have. His male gender would surely have been questioned if it weren’t for the fact that I had showed the sponsors his birth certificate beforehand when I was arranging things.
I didn’t see much of Terry for the two days before the womanless wedding. He and Mary spent most of the time shopping for his wedding gown, matching heels and associated lingerie. Also, the night before the ceremony my sister insisted that Teresa stay in her room, since it wasn’t right for an unmarried couple to sleep together before their wedding!
Finally, the big day arrived. A local church had offered the use of an empty chapel for the event, since it was to raise money for charity. While we waited for the bride, my parents and I looked over the other participants in my ‘wedding’. I noted with amusement that they were obviously all men, even the bridesmaids! Meanwhile, Mary was helping ‘Teresa’ to get ready, and I was certain when she was done no one would mistake my bride for a man!
Sure enough, when Terry appeared, he looked gorgeous, dressed in a long white ruffled gown and a thin veil which did little to hide the beauty of his face. Everyone cheered when he made the traditional walk down the aisle, and I’m sure more than a few doubted it was really a boy underneath the dress, especially when they noticed the ample cleavage he displayed!
In the following hour my bride and I did the vows, the exchange of rings, the first kiss, the signing of a register, and then later the first waltz as man and wife. When we went back to our room afterwards, Terry had on my wedding ring and was carrying a certificate which said we were legally married. Unbeknownst to him, the person officiating at the wedding was an ordained minister, and the certificate was authentic! Terry didn’t realize it at the time, but when he said, “I do,” he was really becoming my wife!
I called him “Mrs. Smith” as I helped my boy-bride out of his wedding gown, causing him to blush sweetly. While doing so I explained that in taking my name he now had to completely accept my authority, due to the honor and obey part of the vows. Looking fantastic in his sexy white wedding trousseau, Terry glanced over his shoulder with amusement at this comment. Then, he replied, “That might be true, Brian, if the wedding wasn’t all just a sham.”
“To the contrary, my dear, the wedding was real and you are actually my wife now!” I then explained about the minister and license being authentic.
“But, how can that be? I’m still really a male and my name isn’t Teresa as it says on the marriage certificate,” Terry pointed out.
“You didn’t realize it at the time, but among all the papers you had to sign so the doctor could put you on hormones was one to legally change your name to Teresa, and another to make your sex officially female on your new birth certificate. In the eyes of the world, you are now officially a woman and my wife!”
Hearing that, Terry suddenly felt faint, and he had to sit down on a chair for support. As the reality of the situation sank in, he groaned, “This can’t be happening. I mean, I’ve still got boy bits hanging between my legs!”
“That’s another thing I wanted to talk to you about,” I admitted sheepishly. “The real reason I chose this town for our wedding was that it is the home of a world renown sex change surgeon. In fact, I made an appointment for you to see him on Monday!”
Terry’s eyes went wide with shock at hearing this. Then, his shoulders slumped, and with a tone of deep resignation in his voice, he said, “I should have fought you years ago, whether it was in entering the womanless beauty pageant, wearing the red stud earrings, or even the toilet seat charade. But, I didn’t, and now I am what you made me to be - Mrs. Teresa Smith! I guess I might as well see this through to the ultimate end that you seem to want so much…”
I picked Terry up and carried him to the bed. As I lay down beside him, I said from the bottom of my heart, “I have loved you ever since I saw you dressed and made up as Teresa for the first contest…maybe even subconsciously before then, I don’t know. However, what I do know is that I will be for you the best husband any wife could have, and I will do everything I can to make your life as a woman as happy and fulfilling as possible!” Then, I kissed Terry, long and hard, and by the time the kiss had ended, it was Teresa who was kissing back!
This was made official one week later when Terry entered an operating room as a boy, and left as a woman, complete with everything but ovaries! I still could not believe that I had actually made this happen, as I checked Teresa out of the clinic and helped her carefully sit in the front seat of my car. I knew we wouldn’t be able to have sex for several weeks, but the satisfaction of knowing that beneath those bandages was a vagina and not a penis and testicles was consolation enough.
As we drove home, I couldn’t stop smiling. I had converted my boyhood friend, Terry, into my dream girl and wife, Teresa, and our future together looked bright! Suddenly, it occurred to me that we couldn’t have children together. I had always wanted to have a son who I could teach to be a man, and a daughter I could spoil and make into a “daddy’s girl”, so this was a big disappointment.
When I thought about it, though, I realized that I could have the children I desired through adoption, or even by using a surrogate female implanted with my sperm! Having resolved this issue, I relaxed and pictured my new wife breast-feeding our baby. I know when Terry was still a boy, he could never have imagined that one day he would have an infant suckling at his breast, and I worried if he’d be willing to do something so femininely iconic. But then, when I turned and looked at my wife and saw the deep love for me in her eyes, and I knew that it would happen, just like I wanted.

The end