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t was Spring, Prom Season. When I was in high school I was a scrawny boy, very fem obviously, and always shy being that my inner gurl wanted to come out. So when I went to my prom I wore my tux, my date got to wear the sexy gown, and I couldn’t help but know the whole night that should be me, but never would be. Fast forward a few years, I came out of the closet, started on hormones, am basically close to full time, and haven’t forgotten my dream of wearing a prom dress. Luckily I’ve met a nice people in my transition into a girl, and great friends are willing to do nice things for a friend. I found the bar (I won’t name it as I don’t think I can on here) when I was still drinking on my fake ID, and found that in December they were talking about having a prom themed party. I got so excited and kept talking about it every time I went in, and I guess I got annoying because they said they would do it. I was so happy. I immediately went out dress shopping with my cousin to find the perfect dress. I ended up with a red satin dress has a chic style with dramatic touches including v-plunging neckline, darling open back design and dazzling beaded work in the center of bust and at back. A thigh-high front slit on the full skirt and small train adds to the drama, a pair of golden 5.5” pump heels, my newly colored soft brown hair in a bun to the side, thick make up, a white push up bra, and a white lacey boyshort, with the white and red garter of course. I felt amazing, I felt ready, I felt fulfilled, I felt nervous! There were going to be a ton of guys and gurls there and I was worried I’d be the most decked out, but I decided I didn’t care, it was time for me to have my prom. I even called a car to come and pick me up and drive me there to make an entrance. I got there and made my grand entrance, and I loved the attention. It seemed as though everything stopped as I walked in, just the attention I had yearned at my other prom. But it was there that I met the man who would change me and it was as soon as I walked in. He took my hand, kissed it, and said “you do realize this is a gay party right?” I giggled and said, “of course, that's why I’m here”. He couldn’t believe I was a transvestite, said that I was way too much girl, and was so flattering about it. Actually, with a man like him, I think I was the one who was flattered he was talking to me. Doug and I spent the whole night together dancing, mingling, flirting, and having a few cocktails of course. It was pretty clear I’d go home with him, he was much older, 45, salt and pepper hair, athletically built, innocent blue eyes, clean shaven, and in a sexy black tux. He finally got the courage to ask me to his apartment at around 12:30 that night and said it was time Cinderella left the ball, I nodded and agreed. We used my driver to take us to his place which was right in downtown Chicago. I paid the driver and told him not to worry about taking me home; I’d find a way in the morning. When we got into his apartment on the 15th floor I immediately started to kiss him just as I did with any guy I went home with, put my hands on his hard body, his hands on my soft body, feeling me under my satin dress, as he lead me to his bedroom. He pulled away and whispered, “I’m going to make you a woman tonight”, which made me giggle because I wasn’t a virgin, which he knew. He continued though, “no condoms for us today, lets just feel each other.” I was nervous, but had thought about this for awhile. Maybe it was the alcohol in me, or maybe it was the night, but I nodded innocently nodded as I looked at him, and began to drop to my knees. His tux pants had a belt which I undid, the whole time my eyes meeting his. I unclasped the pants, I could feel his hard member growing only more with my touch, as I unzipped it came out, and to tease him I smiled and wrapped my little fingers around it, slowly stroking him as he breathed heavily. I put my hands on the waist of his pants, and pushed them as they fell to the floor. His legs were very hairy, but very muscular. I looked up at him, smiled, opened my mouth and slowly let his cock fill my mouth. I began to bob slowly on it, my face touching his pubes as I went further and further in, and it went deeper and deeper down my throat. I could feel the mushroom head brushing the back of my throat, his hand on the back of my head pushing me deeper, my gag reflex coming out a bit as my lips touched his pubes and the bottom of his scrotum. I soon felt his other hand wander down my soft back and unclasp the racerback of my dress so my wide satin straps separated from each other in the back, and loosed the top of my gown. He pulled out of my mouth then and got me to stand, and I let the dress slide off my baby soft body showing my newly forming perky tits in my little white bra, white lacey boyshort and the garter fastened on my leg. As his large body approached me to kiss me, our tongues wrestling with each other. I undid his shirt button by button as I slipped it over his shoulders to reveal a slight gut, but a very toned pectoral and arm region. His hairy arms grasped my half naked body harder in his arms as I was laid back on his bed. Looking up at him as he began to lick my small tits, and then the rest of my soft body. Going from my tits, to my slim tummy, seeing the saliva trail he was leaving as he took his trip, lower and lower. I felt his hands grasp the hips of my panties and he trailed them all the way down my long tanned legs, me moving them to help him out, feeling the lacey material leaving my body as it went around my ankles, and got stuck on my left pump we left on. I felt my cock enter his mouth, as he sucked my limp dick. His head bobbing on me as my back arched up in ecstasy. I started to thrust my hips as I wasn’t used to getting sucked, my hand went and pushed my bra down and grabbed my tits as I bit my lips in the pleasure I was feeling. Then I felt him get serious as his hand went by my boipussy and his finger began to trace my asshole giving me a tingly sensation, and making my cock grow all it could. He pulled up and smiled at me, leaving me so teased, but so ready. His teeth grasped my red and white garter and he began to slide it down my long leg, peeling down the thigh, then easily down the calf, and then flipping it over my 5.5” pump. He put it around his arm and smiled, and I said “you’ve earned that” and he replied “not yet, but I will.” Then he went into a drawer to get out his KY warming jelly and put it all over his fingers as they prepared to enter. He rammed them into me without the gentleness he had once practiced with me earlier and I felt my hole expand and open with his power. I sat up as I did feel pain from it, but could only bite my lip and watch him ready me for him. As my ass was opened, and ready for him, he pulled his finger out and wrapped his lubed fingers around him cock to make it so slippery and warm for me. It was standing out straight, and he was pulsing it so it twitched upward saying that it was just getting started for me. He put some more lube on it, and then picked up my legs and put my heels over his shoulders, smiling knowing he would have my raw ass for the first time. I felt the tip of his dick touching my asshole as I moaned in desire, undoing my bra so I could play with my tits for him. I nodded to give him the OK to plunge in me and take me. I felt the cock slowly slither into my body, opening me up, my body began to flinch and squirm a bit as it was around 7.5” or 8” which was rather larger, and my asshole wasn’t used to that size really yet. I could feel the skin on skin, the veins better, the mushroom tip all invading my ass, as he plunged deeper and deeper by the second. I changed position as it filled me to try to make myself comfortable as I kept my left leg over his shoulder, and my right leg around his waist with my heel right over his ass. Soon after he was all the way in and began to thrust. He didn’t take too long to get going quickly, he was thrusting me hard; my girly body was shaking from his manly power. I told him what a big boy he was and how he was going to own this pussy when he was done. He was letting out grunts and moans making me wonder when he would cum. I could help but feel how amazing the walls of my ass felt with his bare skin, feeling as if I had been missing out, that condoms were cheating me of extra pleasure. He leaned in to start to kiss me, our tongues dancing yet again, I felt his cock grow even harder as he began to pound more authoritatively, as he pulled up and said, ‘fuck you baby’ and I’ll never forget the next feeling. With one hand on my little breast, and the other on my hip, I heard him grunt loudly, a cum grunt, and I immediately felt a warm sensation in my ass, I moaned so loudly, so purely as though I was singing a beautiful song. Rope by rope I felt his dick shoot in me, I wished it would never stop, his cock thrusting, hearing the swishing of the near fluid in my body on the walls of my ass and the skin of his dick, being forced deeper and deeper into my body. As I felt the cum turn from ropes to a few drips I felt him slither out of my body as I gasped out how amazing he was, flipping up on my hands and knees, opening my mouth to clean my ass and his cum of his dick as it grew limper. He smiled at me, out of breathe, telling me how amazing it was, and that it was the best prom night he had ever had. I smiled as I began to slide my gown back on myself. As I slide it on I had to keep my ass shut to keep the cum in, but leaked some and loved the feeling of it as it slide down my soft thighs in the cab ride home. It was a night that changed me and made me realize the greatness of bare sex.
