CHAPTER 10
Meet Ashley
As I walked out into the world again, I was in an emotional high. It was now mid-January, and the weather was cold. But I didn’t feel cold. I felt ecstatic. As I walked down the garden path that led towards the main house, I tried to catch a glimpse of me anywhere I could... in the swimming pool reflection, in any bay window I passed... etc.
I was enjoying being outdoors. It was like a drug. The wind was hitting my face and playing with my hair. It seemed like the colors were brighter. I felt free. Renewed.... reborn.
But as I approached the main entrance, I started to feel extremely nervous. After all, I had never been dressed as a woman in the presence of anyone else. The incident with the cheerleader uniform in the locker room and Martha’s Vineyard don’t count, because I was HIDING. But I had never been dressed as a woman in a public, social event. And that thought crept into my head as I approached the door.
I stopped at the door wondering what should I do? Should I go back to the bungalow and wait for John? Should I go inside and just go with the flow? I was nervous and scared, but at the same time I was ecstatic and confused. All at once. Up to this point in my life I had been Ashton. The minute someone else saw me like this... there would be no turning back.
Suddenly the door opened. It was one of the cleaning ladies. She startled me. I froze. She simply came out of the house carrying a broom and a dustpan.
“Excuse me,” she said casually as she walked into the garden. I just stared at her. She hadn’t reacted strangely. She didn’t stare at me. Except that she suddenly stopped and turned around to look at me. I thought... “here it goes... she knows I’m really a guy and she’ll say something...”. But instead, she simply said, “It’s awful cold out here, miss. Maybe you would be more comfortable inside.” Then she smiled and walked away.
Her words began echoing in my head... “miss”... I took a deep breath then relaxed. A soothing feeling washed over me. It gave me strength. it gave me courage. So I stopped fidgeting, opened the door and walked inside.
It was the first time I stepped into the main house. I didn’t know which way to go. So I started to make my way across the hall towards the living room. I could hear John’s voice coming from there. I stopped quickly by a mirror hanging near the entrance and checked my hair and makeup. I still couldn’t get over myself how pretty and feminine I looked. I kept staring at my eyes. They were still MY eyes. But the rest of my face had become the face of a girl. I took a deep breath and made my way into the living room.
John was standing by the bar pouring himself a drink. Sitting on a chair, was his business associate. A tall, black, former NBA player called Kevin. They were talking shop... something about investment banking, stocks and stuff like that. But as soon as I came into the living room, Kevin suddenly fell silent. John looked up and suddenly he fell silent in mid-sentence. He was so taken by surprise, he actually froze. He didn’t notice that he was still pouring whisky into the glass and it was spilling over the bar.
There was a deafening silence hanging on the living room. Both men simply stared at me. Kevin was calm and curious as to who I was. But John looked like he had seen a ghost. His face went pale and his eyes widened like dinner plates. He quickly tried to regain control of himself. He noticed he was spilling his drink and began fumbling behind the bar. “Shit!”
I was incredibly nervous. All of my confidence suddenly flew out the window the second I realized I had become the center of attention. I tried to say something, but I became self-conscious that my voice would still sound male, so my mouth was just open and no sound came out. Finally, I was able to stutter, “I’m sorry... I didn’t mean to interrupt.”
Kevin immediately stood up to greet me. He was very tall, about 6.5 and lean. He had a Denzel Washington air about him, only taller, much taller. “That’s okay. We were finished talking about business.” His voice was deep and soft... It sounded a little like James Earl Jones.
I started to back away very shy. “I... guess I’ll leave you two alone”. Kevin suddenly looked at John. John had managed to get a grip and bolted from behind the bar towards me. “No, no. Please join us.” He grabbed me by the arm and led me into the living room towards Kevin. “Kevin. I want you to meet...” His voice trailed off as he examined me. Kevin was curiously awaiting the answer... “Yes?” he asked. John snapped out of his stupor when he heard Kevin. “Ashley! Sorry I was just... Um, she’s... my... a very special person...”.
Kevin held out his hand and I shook it. His grip was strong, but gentle. I could feel his strength through his hand. Suddenly I felt John’s hand go around my waist and I blushed. John seemed very nervous. And the way he put his arm around me when Kevin shook my hand was almost... possesive. As if he was jealous or something. He led me towards a sofa chair and invited me to sit. I sat down putting my knees together because I was very self conscious of what still lay inside between my legs.
John walked behind the bar once again. He was rapidly regaining his composure. When he talked to me, he seemed totally in control once again. “What’ll you have, Ashley?” I meekly replied, “club soda...”. John smiled as he began fixing me a drink. “Club soda? What’s the matter? Don’t you remember Martha’s Vineyard?” The memories of that summer at Martha’s Vineyard suddenly cascaded into my head and I blushed once again. John went on, “what was it that we drank that night?” I blushed. I was incredibly nervouse. I looked away and softly said, “margaritas...”.
Kevin just stared at me.I could tell right away that he was into me. But I didn’t know how John would react if I met Kevin’s gaze. So I kept avoiding eye contact with him. John handed me my drink and I started sipping it to calm down. Kevin finally asked John, “So, John. How did you to meet?”
John laughed. Then stared right into my eyes. “Well... we met last year. Through some very good friends of mine. I invited her last summer to Martha’s Vineyard. That was some summer, wasn’t it, Ash? Lot of new discoveries...”
I simply nodded. I kept drinking the club soda in order to avoid speaking. Kevin smiled and looked at both of us. “So.., are the two of you... dating? What’s the story John?”
John didn’t even look at Kevin. He kept his eyes on me. It was like he was taking in the way I looked. After all, I hadn’t given John any heads-up regarding my appearance. “I’m not sure, Kev. What do you think Ash? Are we dating?”
I looked directly at John. I had just finished a glass of club soda, but my mouth was suddenly parched. I looked at Kevin and then back at John. It was obvious that John was putting me in the spotlight and I wasn’t going to be able to sneak out of that question. I took a deep breath, put the glass aside, managed to grab on to all of the courage I could muster, and turned to Kevin.
“I’m not sure, Kevin. You see, John is a very, very special person. When I met him, I had to face some hard-fact about myself. As it turns out, John knew me better than I knew myself. I don’t know what we are... yet. But I can tell you something...” my voice trailed off, then I turned around and looked at John straight into his eyes. “I haven’t stopped thinking about him for the past six months”.
John never imagined I would face him like that. Suddenly, he was nervous again. And he had trouble swallowing. I stood up and walked towards John. His nervousness gave me the courage to push on. “I think I’ll have that Margarita after all...”. Then I slammed the empty club soda glass on the counter. As I stared into John’s eyes, I said, “what about you, Kevin? How long have you known John?”
“Since we were in college. I was the jock. He was the brains. We were roommates. So John. Ashely is your girlfriend, then? Certainly looks that way.”
John quickly regained his composure. He stared into my eyes and replied, “No. She’s not my girlfriend... yet. She’s just... a very special friend”. John put the Margarita in front of me and I drank it with one gulp. Suddenly I felt... safe. I finally relaxed. “May I have another?” John smiled and fixed the drink. I grabbed it and calmly walked back into the chair. John looked at me and winked. Kevin kept staring at me, but now, I felt safe enough to look back at him.
I looked down at my pantyhosed legs. I couldn’t believe it. Here I was in one of the most feminine outfits ever, looking like a million bucks, totally comfortable and feeling incredible. I ran my empty hand up and down my thigh totally ecstatic about the way I looked and felt. John said, “another Scotch, Kev?” “Sure!” Kevin stood up and walked over to the bar.
As John fixed Kevin his drink, I simply allowed myself to enjoy the evening. John and Kevin continued to talk about all kinds of stuff through dinner and I kept touching myself very discreetly enjoying my skirt, sweater and pantyhose. Kevin would stare at me from time to time and that would make me a little self-conscious about my makeup. So occasionally I would retouch it to feel more confident.
John would also keep staring at me. But unlike Kevin, every time John looked at me, I enjoyed it.
Kevin excused himself to go to the bathroom and John took advantage of the opportunity to finally talk to me on a more personal level. “Jesus Christ! You look amazing! I never imagined you would become such a gorgeous looking woman. I thought that you wanted to go back to...”.
“I know. But when you brought me my old clothes, suddenly they felt... wrong. I guess you were right all along.” I said.
“How do you like Kevin?” he asked.
“I think he’s great. But... he makes me a little nervous” I said. “Why?” asked John. “Well, he’s gorgeous and I don’t want him to know that I’m a... “ Suddenly, I couldn’t finish the phrase and I covered my mouth with my hands. John simply stared at me in disbelief. I couldn’t believe that I had made a reference about another man as “gorgeous”!
John said, “gorgeous? I... He... Of all the things you could’ve said, the first thing you say is ‘gorgeous’?” John suddenly stared at me without saying a word. I didn’t know what to say next. I felt exactly the same way as when I saw that video of me wearing John’s ex-wife’s clothes at Martha’s Vineyard. I tried to say something, but John simply put his hand up. A mischevious smile suddenly appeared across his face.
Kevin returned to the table. “Sorry... I had to take care of some personal phone calls. So... what were you talking about?”
“Well... “ John began to say, “it seems that Ashely has a little crush on you...”. I gasped and covered my mouth with both hands. Kevin suddenly whipped his head around to look at me. John simply smiled. Once again, his dark side had appeared. He was like a puppet master playing with me and Kevin. John looked at Kevin’s reaction. I wanted to crawl under the table and die. Then suddenly I noticed Kevin begin to blush and get very nervous. We all sat in silence.
John stood up and walked over to me. He began pulling the chair from under me, very gently but firmly as he spoke. “Excuse us for a minute, Kevin. I need to have a word with Ashley.” I stood up and literally raced out of the dining room. I could hardly look at Kevin anymore.
As John entered the next room he closed the door. I felt humiliated, angry and nervous. “Why the hell did you tell Kevin that I had a crush on him?” John suddenly grabbed me gently by the arms. Then he firmly sat me down and pinned me to the chair.
“Look. I never... and I mean NEVER imagined you would become an incredible-looking girl. Well... almost girl. I’m really, really glad you look like this. Because deep down, I know you’re mine. That means that I’m about to get my wish... the perfect woman. So don’t speak like that to me again, ok?” I calmed down and shook my head. He went on, “As I told you before, I need you to be 100% certain that this is what you want. I take it, you want to me MY woman. But... you’re not a woman yet. There’s one last test you have to pass. And your little remark gave me the perfect opportunity to put you to that test.” John backed away and sat in front of me. He smiled warmly again.
I looked at him curiously. “What are you talking about. What test?” I asked.
“You see... there is one slight problem about you becoming my girl. What if you don’t like it? I mean, I can see you enjoy looking like a woman. But... you still need to FEEL like a woman. And in the end... you’re a virgin. You’ve never had sex. Not as a boy... And certainly not as a girl... So... I want you to have sex. For the first time. I want you to have sex with Kevin. You said yourself that he’s gorgeous. So... you’ll spend the night with him. And after that... we’ll discuss the next steps. I will talk to him about what you have between your legs so you don’t have to explain anything. So... let’s go back in there.” He stood up and walked towards the living room.
I was shocked. I couldn’t move. I couldn’t say a word. I stared into space and let John’s words ring inside my head: “...I want you to have sex with Kevin...” I couldn’t believe it. How could he say something like that. As he got to the door he turned back to me. “Don’t take too long... I know I said I would support you in your decision. But like I also said, don’t cross me.”. Then he left me alone.
CHAPTER 11
Ashley Loses Her Innocence
It felt like hours… but only a few minutes had passed. John’s words kept ringing inside my head: “For the first time. I want you to have sex with Kevin.” Sex with Kevin. The nightmare was back. I suddenly realized how naïve I was at the prospect of having sex. Up to now, my sexual experiences were limited to one thing: masturbating… ALONE. And now I was to have sex with a MAN. Not just any man. A grown, full-bodied, tall, handsome man.
As I thought about that, I started thinking about Kevin. Would he have a big dick? Would he have a small one? Would I have to suck it? Or simply turn around, bend over and let him fuck me in the ass…
Once again, I was very frightened. I didn’t know what to do. Or how to react. What would I say when I returned with John and Kevin? “Uhm, Kev… I’m ready. Ready to fuck me?” I took a deep breath and had a look around the room. There was a mirror where I could see myself sitting down. There I was: a girl. A young, 18 year old girl unsure of what to do.
Then I caught myself in my own thoughts: A GIRL! I was thinking about myself… AS A GIRL. Not Ashton. Not even Ashley. Simply… a girl. That thought made me smile. It gave me courage. So I got up, and confidently walked back into the dining room. As I walked in, both men stood up. Kevin walked over behind me and pulled the chair under me. I couldn’t help but smile a lot. It made me feel… girly.
I sat down. I was very self-conscious of myself. Very subtly and gently, I would touch my legs. I wanted to feel my panty-hosed legs. I had crossed my legs very lady-like. But since my legs were under the table, only I knew it. And that made me feel very feminine. I would catch Kevin stealing glances at me. I could feel his stare, but when I looked at him, he would blush and turn away. That made me feel pretty… and feminine. And for some reason, it also made me feel powerful. And I liked it. No. Wait. Actually, I loved it. I wanted to feel prettier. More feminine. And Kevin was making me feel just like that. The fear of having sex with him was rapidly disappearing, and instead, I was very curious to find out what it would be like to have sex with him. The mutual attraction was palpable and John had grown very uncomfortable at our flirting.
Kevin tried to lighten the mood. “So, Jack. How about a little game of one-on-one after dinner? I’ll spot you 15 points.” John laughed. “No way… I don’t want you to rape me”.
“Well, if John doesn’t want to get raped… why not rape me?” There was a deafening silence that suddenly fell down on the room after I had challenged Kevin. I couldn’t believe I had said it. But it was too late to take it back. I was feeling so pretty and feminine from Kevin’s stares, that I had lost my fears. I was feeling very much like a woman. And… just as before, now that I had reached a new level of womanhood… I wanted MORE.
Kevin was blushing. John was dumb-struck. I was smiling at Kevin. I turned to look at John. And suddenly, I thought I caught a glimpse of deep jealousy. He looked at Kevin with a cold stare that I had received many times before when John was upset at me. But he was the one who had provoked this. So he had to sit, be quiet and suck on it.
Kevin finally managed to say, “I’m sure you’re kidding”.
“No. I play a mean one-on.one. I don’t care that you played professionally for the NBA. You don’t need to spot me 15 points.” I said. I was totally flirting with him and I couldn’t help myself.
Kevin started laughing. John finally loosened up and smiled. I got up and excused myself. “I need to go to the ladies’ room”. Both men stood with me as I stood up. I started to walk around the table. John and Kevin began to sit down.
I was feeling incredibly horny as I walked into the bathroom. My limp dick was very sensitive and I felt an uncontrollable need to rub it. That’s the reason I excused myself. Although my dick wouldn’t get hard anymore, it was like a small stub. You could flick it with your finger. But it had shrunk to about 5 inches. There was some firmness to it that kept it from being completely limp. But I couldn’t really call it “erect” either. I kept rubbing it and rubbing it. I would press my knees together as I lifted my skirt so I would rub my tiny little dick harder. I caught a glimpse of myself on the bathroom mirror, and I couldn’t believe my eyes. There she was: a beautiful girl masturbating. It was like a scene from the porn shows I used to watch when I was 13 and alone at home. Those days seemed to be so long ago and so far away. But as I watched that beautiful girl masturbating, all I could think was: “she doesn’t need to jack off. She’s so beautiful she could fuck anyone… anytime.” As that thought struck me I couldn’t hold it any longer and I finally had a huge orgasm.
I had to bite my fist to keep myself from screaming. And I could feel my dick cuming inside my panties and my pantyhose. I slumped down on the toilet seat. I suddenly began to relax. I felt… exhilarated. But at the same time, I could finally relax. I felt… wonderful. No guilt. No remorse. But suddenly I felt uneasy. I felt my dick cuming into my panties. And I felt it moist. I shut my eyes thinking, “I’s so stupid… I’m going to have stains”. I lifted my skirt and checked my crotch. To my surprise only a few drops of a transparent fluid had been shot. It felt as if I had shot a lot of fluid. But in reality it was only a few drops. It had been mostly a dry orgasm. It was something new. I was used to wet orgasms. But I had barely shot any cum. Yet, the orgasm was deep, wonderful and it felt like it lasted for a long time. And since my panties and hose were black, it didn’t even stain it. Plus, the skirt would cover my crotch, anyway.
I relaxed, straightened my skirt, checked my makeup and returned to the table. John and Kevin were now standing by the bar. They had a brandy and John was lighting a cigar. He looked up at me, and without stopping to light his cigar, he asked me, “everything all right?”. I walked over, put my arm inside his arm, and rubbed myself very close to him. “Yes. Everything’s fine. In fact, everything’s… perfect. You’re a genius. You knew me better than I know myself”.
John stared at me in disbelief. I let him go, and grabbed Kevin by the arm. “Kevin, would you go out on a walk with me?”. Kevin felt like I was putting him on the spot. He turned towards John hoping to find an approving look. John smiled at me. I smiled back. John said. “Sure! I think it’s a great idea!”.
Kevin smiled and he led me outside. We walked together for a short while. We made small talk but I really wasn’t listening to our conversation. All I could think was, “what will Kevin’s dick look like?”. Finally, after a short walk, I told Kevin, “you know, it’s too cold. Will you walk me to my room?” Kevin simply said, “Sure.” He was about to turn towards the main house, but I led him towards my bungalow.
He opened the door for me as he said, “say, this apartment is pretty cool. You’re staying here?” I simply replied, “uh hum”. He closed the door behind him and I turned on the light. I turned around and looked at him. I looked around and I caught a glimpse of the two of us in the mirror. It was like having an out-of-body experience. I just had an orgasm. And yet, I was still horny. I didn’t know what to do. I was hoping Kevin would make a move. I didn’t have to wait too long. He gently grabbed my chin, and kissed me.
Once upon a time, the thought of me kissing a man, would’ve sent cold chills down my spine. At the very least, I would’ve thrown up. But that was Ashton. He was a coward and an asshole. On the other hand, Ashley welcomed the kiss. I couldn’t believe it. MY FIRST KISS. I could feel Kevin’s tongue in my mouth. And instead of feeling repulsed, I closed my eyes and allowed myself to enjoy it. My tongue began to play inside Kevin’s mouth. The taste of brandy was incredible. I wanted more.
Suddenly, my body started to act on its own. I felt Kevin get a hard on against me. It was the first time IN MY LIFE that I felt a foreign dick against me. I hadn’t realized that until that point. The only dick I knew in my life, was my own. I had never touched any other man’s dick. And now, here it was, a huge cock rubbing against my waist. It felt hard, but at the same time, it was flexible. My hands reached out for it and grabbed it. Kevin let out a moan. I let go, thinking I had hurt him by squeezing too hard. But he whispered: “no. Don’t let go”.
So I grabbed it again. He moved his hand and grabbed my breast. It felt incredible. I could feel my nipples get hard as he played around with them. I felt pangs of delight run down my chest and into the pit of my stomach. I moaned with pleasure. At my sounds, I could feel him getting harder and harder. He began to move his hand towards my crotch, and suddenly I became very self-conscious. I pulled back and grabbed his hand.
“Wait.” I said. “You see…”. Kevin interrupted me. “I know. John told me. It’s okay. I’m a little nervous too. I’ve never been with a… a…” He was trying to find the right word to describe me. Finally he asked, “What should I call you?”. I simply smiled and hugged him again, rubbing my body against his dick. “Well, if it’s okay with you, you can call me your girlfriend for tonight”. Kevin smiled and kissed me again. I started rubbing his hard cock over his pants. He lifted my skirt slowly using one hand and reached my crotch. I could feel his huge hand cup my little limp dick. It felt wonderful. My little dick began to pulse. He could feel it. He could feel how hot he had made me. So he lifted me in his arms and carried me over to the bed. As I felt my feet leave the ground and into his arms, I missed a heart beat. I was in paradise. I heard myself say, “Oh, God”.
He sat me on the bed. Almost immediately, I went for his belt and began unbuckling it. He started to play with my hair and kept saying, “my God. You’re beautiful”. I threw the belt on the floor and unfastened his pants. I dropped them around his ankles and his dick was tent-poling his boxers. I looked up and we locked eyes. I wasn’t thinking anymore. My body and soul were on auto-pilot. I pulled down his boxers and his huge cock sprang right in front of my eyes.
I couldn’t help myself. I had to touch it. I had to kiss it. I had to lick it. I caught myself saying “Oh, my…”. I smiled and grabbed it. Kevin closed his eyes. I started rubbing it. But before he could say anything, I felt the urge and put it in my mouth. I couldn’t believe it. I had a cock in my mouth. And I was enjoying it. I started giving Kevin a blow job. And every time I pulled back, I had the urge to squeeze his bulb with my tongue. Kevin would moan in pleasure. I kept sucking harder and harder, faster and faster until Kevin couldn’t hold it any longer and suddenly he came in my mouth.
There was an explosion of salty fluid on my tongue. I guess I should’ve been repulsed. But I was far from being repulsed. Instead, I started to swallow. And I started sucking harder on him. I wanted him to fill me with his cum. I wanted to taste every drop. I could hear Kevin scream with pleasure and I could feel his knees buckling. I kept sucking on his dick until I started to feel his dick get softer. He suddenly grabbed me by the hair, and slowly he pulled me away from him and got his dick out of my mouth.
“Sorry… It’s just that it was almost getting painful. Jesus, Ashley. I’ve never gotten a blow job like that before…” he said, panting.
“I’m sorry, Kevin. I didn’t know I did it so bad. I didn’t mean for it to hurt. It’s just that… it was my first time.” I said lowering my eyes to the floor, and suddenly feeling very uncomfortable.
Kevin gently grabbed me by the chin and lifted my face. “No. I never said I didn’t enjoy it. Totally the opposite. I had never ENJOYED a blow job so much before. That’s what I meant. But after I came, my dick became very, very sensitive. And you just kept going. You sucked me dry. You swallowed everything I had and kept sucking. No girl EVER had done something like that to me before.” He smiled warmly.
I smiled back. He sat next to me on the bed. “Was that really your first time?” I simply nodded. “Shit. You could’ve fooled me”. I turned around surprised and looked at him. I guess he must’ve misunderstood my stare, because he quickly added: “I don’t mean that you’re a slut or anything like that… No offense.”. I relaxed and smiled. Then I put my head on his shoulder. “Don’t worry. None taken. I’m just really, really glad you liked it”. We held each other for what seemed a long, long time. We kissed again, then I relaxed and lay down on the bed.
Kevin stood up and turned around. “So, you’ve never had sex before?”. I shook my head and smiled timidly. Then he asked me “Would you like to?” I smiled broadly and slowly, very slowly nodded. So he finally asked, “Do you have any Vaseline? Or baby oil?”
CHAPTER 12
Popping Ashley’s Cherry
Vaseline? Baby oil? What did Kevin mean by that? I sat up on the bed.
“Uhm, I have baby oil. It’s on my dresser.” I pointed towards the dresser. Kevin walked over and took it. His big dick was hanging down. Even flaccid, it was still a good sized dick and kept bouncing up and down with every step he took. I found myself staring. I couldn’t help it.
Kevin walked over and sat next to me.
“Ashley. You’re a virgin.” I blushed. Kevin went on. “I don’t mean to say that to embarrass you. But you don’t have a…” his words trailed off as he looked at my crotch. “Anyway. Your ass is way too tight. We need something to help me get inside of you. Otherwise I will most likely hurt you. Even damage you physically. Emergency room-type damage”.
He held my face. “My God. I can’t believe how beautiful you are”. His words made me shiver. No one had ever said that to me. To hear it, made me very horny. I couldn’t help myself. I went for his dick, and started stroking it. He kissed me. My little dick would begin to pulse.
Kevin pulled back. Then, slowly, he took my angora sweater, and lifted it over my head. My little tits were nicely tucked inside my lace bra. I was trembling. It was a mixture of fear and excitement. I didn’t feel like myself. But I was fully enjoying every second. I didn’t want the night to end. Kevin started kissing me again. Then he moved his hand and started touching my tits. I could feel the nipple get hard. I had never noticed how sensitive my nipple was. Having Kevin squeeze it gently made me incredibly horny.
I started unbuttoning Kevin’s shirt. He had rippling muscles. Not like a body-builder. But he was nice and solid, and you could see all of his muscles. I started running my hands all over his chest and belly. I loved the feeling of those muscles. And he had little body hair. Just enough to feel it. It was so nice to feel body hair after so long. My body was completely smooth. I ran my hands down Kevin’s torso to his legs. They were like two pillars of dark marble. Solid. Beautiful. Well toned. And with a soft fuzzy feel from his hairs… My little dick was erect. It was soft. But strangely erect.
Kevin noticed my tiny little dick and smiled. “Are you enjoying this?” he asked me. I simply nodded. He grabbed me under the arms and gently stood me up. I opened my eyes. He walked up to me. His dick was starting to get hard again. He ran his hands behind my back and unfastened my skirt. It dropped around my ankles. I pulled his shirt back and tossed it away. Kevin was naked, except for his socks. His dick was beginning to rise. I was in a bra, panties, pantyhose and my boots.
Kevin sat me down again and began running his hand down my panty-hosed legs. He unzipped my boots and gently took them off. Then he stood me up again. He grabbed my pantyhose and started pulling them off. My little dick had made a tiny tent with my black panties. I felt my black pantyhose fall around my ankles so I stepped out of them. I kneeled down and rolled Kevin’s socks off his feet.
He unfastened my bra and my little tits sprang up. He started fondling them. I started fondling his dick. He pulled me back then handed me the baby oil.
“Here. Put it all over my dick. As much as you can.” I popped the cap and started rubbing baby oil all over his dick. He started moaning. As I rubbed his dick with baby oil we locked our eyes together. He asked me, “are you sure you want to do this?”
I was beside myself. I couldn’t stop. I had to go on. I was feeling incredibly horny. It was the first time I was going to have sex, and I didn’t want to stop. I said, “my, God. Yes. I want you inside of me”.
Kevin grabbed me by the waist and spun me around. He pulled down my panties. I stepped out of them. Then he grabbed my legs and spread them apart. He grabbed the baby oil, and squirted it into my ass. The feeling of the baby oil made me tremble. Then he started to rub the oil all over my ass. Then, suddenly, without warning, he took a finger and shoved it inside my asshole.
I screamed. I never expected it. But Kevin didn’t pull his finger out. Instead, he asked, “did it hurt?”
I replied, “No. Not at all. You just caught me by surprise”. I started to tighten my ass around his finger, enjoying it.
Kevin said, “No, baby. Don’t tighten your ass. Relax.”
I started to relax and he pushed his finger deeper. It started to hurt a little and I moaned. He started moving his finger around, pushing the walls of my asshole. I was in heaven. I grabbed my little dick and started rubbing it. Occasionally, my ass would start to hurt. When it did, I moaned. But Kevin wouldn’t remove it. He would try to open my ass wider. And it did hurt. I stopped rubbing my dick, and instinctively, I grabbed the wrist of the hand that had the finger inside. But he wouldn’t let me pull out his hand.
“It hurts a little”, I said.
“It’ll pass. Give it time” he replied.
I held on to his wrist as he widened my ass. Then he pulled his finger out. My ass relaxed and I felt deliciously horny. “More”, I said. I don’t know where the words came from. But I was glad I said them.
Slowly, Kevin pushed me down on the bed and spread my legs. “This is it”, I thought. No turning back. I will become a full woman. I couldn’t wait.
Then I felt it. The tip of his dick roaming my asshole. I started moaning. I started pushing my ass up to meet his dick. “Relax, baby” he said. I was beside myself with anticipation. “Please. Put it in, Kevin. Make me a woman. Fuck me”.
Kevin started to push his dick inside my asshole. The pleasure I was feeling suddenly turned to pain. His dick was huge. I started to scream. “Oh, shit!” I grabbed the bed sheets and started biting down on a pillow. “It hurts”, I screamed. “It’ll pass”, he replied.
Slowly, he started to push inside me. The pain seemed unbearable. I started to scream in agony. But Kevin wouldn’t back away. He would stop, but leave his dick inside me until my screams subsided. Then he would push in again.
I started to cry from the pain. I felt as if his dick had made his way into my belly. I felt stuffed. Like when you need to go take a shit. I tried to push his dick out. But that only made Kevin hotter. I felt as if my ass was on fire. It was very painful. I would try to squirm, but Kevin would hold me with his other hand and keep me in position.
“Oh, God. It hurts so much”. I cried. Kevin would keep pushing his dick inside of me. Slowly, I felt the pain begin to fade. Very, very slowly. I still felt like I had to take a shit. But I felt as if I was getting used to it, and the fire in my ass was slowly passing. That made my asshole relax a bit. The minute Kevin felt my ass relax, he pushed harder inside of me.
At first I thought I would be impaled. I was expecting the pain to return. But instead, I felt the most wonderful feeling. Kevin had pushed so deep and his dick was so long, that he touched my prostate. I let out a great scream. But it was a scream of pleasure. The sensation of being stuffed had passed. And now there was a feeling of absolute pleasure that was coming from inside of me and spreading towards my crotch. I was as if Kevin’s dick had reached my dick from the inside. It was a wonderful feeling. I started pushing up with my ass. I wanted Kevin deeper.
He started to fuck me in a nice rhythm. I pushed back every time he pushed in. I started rubbing my dick. I was in heaven. I didn’t want it to end. I started panting and moaning like a girl. I kept yelling, “yes, deeper, harder”. That made Kevin even hotter.
I felt like I couldn’t take it any longer. “I’m going to come…” I yelled. Kevin panted, “go ahead, I’m about to come too… Let’s try and see if we can come together…”
By now, Kevin was fucking me really fast. I felt like I was about to pass out. My left hand was trying to lift my body enough so my face wouldn’t smash against the bed, while my right hand kept rubbing my dick. I kept panting and moaning every time Kevin pushed inside. “ah, ah, ah!”
Finally, we both exploded into a huge, incredible orgasm. We both screamed at the same time. Kevin pushed inside and grabbed me by the waist as he exploded inside of me. He screamed, “Oh, God!” I screamed “Yes! Oh, God! Yes!”
I never expected an orgasm like this. It felt as if it lasted for hours. I could feel a fluid start running out of my ass and down my legs. I didn’t know if it was blood or cum or what. But I loved how it felt. Kevin started to pull out, but I grabbed his hands and pushed back against him. I didn’t want him out. I wanted him inside of me… forever.
Slowly, I felt Kevin’s dick soften. He couldn’t keep it inside of me anymore. His dick simply popped out of my ass. Then we both collapsed on the bed. Kevin held me. We spooned. I could feel Kevin’s soft, flaccid dick against my ass. I felt my ass ooze with Kevin’s cum. I was in heaven. My dick had cum too. Very little. It had made a small stain under my crotch. And now it was a tiny little protrusion in the middle of my crotch. I started to hate it. I wanted it gone.
We were both really tired. I was trying to wrap my head around what had happened. But I couldn’t. The day had been too emotional. Too intense. I simply allowed myself to drift into a deep, restful sleep in Kevin’s arms.
My emotional transition was complete. Ashton was gone forever. He had completely disappeared. He was a virgin that had gone away. Now, there was only Ashely. Who had enjoyed the best sex of her life.
And now, she wanted more…