It was a regular, old prom night, or at least that’s how I thought it was starting anyway. I had went out the night before and got my tux, but before that let me introduce myself, I’m Tony, I’m 18, long hair, probably to my upper back, I’m in a band so I like it long, I’m just under six feet talk and slender, with a feminine type body. I do get girls, but just knowing that I could pass as one if I really wanted to turns me on and I have to dress up sometimes.
But anyway here is what happened, I got my tux and came home, I was so horny I threw on some panties and masturbated, don’t worry this isn’t the good part, then went to bed. I awoke taking my shower and getting out of school early to get ready, once again I was horny and thinking about the cute guys at school, so I just had to masturbate again, I marched around the house in panties all day, and fucked myself with a dildo later on, still not the good part.
Well I finally got ready and went through the whole picture thing, dreading this all day with the parents and grandparents, finally my ride arrived, one of my friends and her boyfriend showed up to get me. I got in and we chatted for a bit until we got to the hotel the prom was at, she was about as tall as me and he was a little taller, we were all pretty good friends, and I knew they would be leaving early since we had a room, but they would want some privacy.
We got there, ate and danced, finally they left, about half way through and when they did I made my way to the bathroom cause I had to pee, there were no boards in between the stalls and there were a few guys in there, none I really had my eye on, so I idly chatted as I waited for a bit as I waited my turn. Finally I got there, standing as I unzipped my pants, revealing my fairly small cock, only about 4. 5 inches when hard, well I turned for a second and there is my friend Derek, at the stall about three down, no one in-between, and he’s standing a little ways away from the stall, allowing me a perfect view of his beautiful, semi hard, 8 inch cock.
Blushing I turned around and finished talking as I zipped and washed up, leaving without saying another word to him.
Just then the idea struck me, my friend, Daniel, the girl I arrived with, well she was about my build, she was obviously by now naked, if I could wear her dress, I could get Derek, not as Tony, but as Toni. With my plan already brewing I ran upstairs and stopped at the door of the room "Oh crud" I thought, why was I hear, what was my excuse, and how would I get back out. . . Just then I struck me, I knocked, Daniel answered, with a sheet around her "Damnit Tony!" She yelled.
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"Look" I said "I really need to get in, I REALLY don’t feel well and I’m not comfortable using the bathroom downstairs, I promise I'll be quick and you wont even know that I left, I wont interrupt you guys I promise. "
"You already did, so what the hell, c'mon. . . "She sighed and let me in as I rushed into the bathroom, just as I thought, her dress, and make-up sitting there, the must have taken a shower together.
I grinned as I pulled the dress off the rack, just hoping to god, yes! her panties and bra were on the floor, she had almost no boobs, so I would fit in it almost perfectly.
With that I went to work, I checked my legs that were already shaved from my feminine adventures the day before, in fact all my body hair was gone, and my facial hair already shaved short. With that I tucked my penis away, pushing my balls into my body and slipping the panties, hoping it would stay. Clasping the bra, I put on the dress, put on some make-up and put my hair up, looking at my watch I gasped, three quarters of the way over! I groaned as I quickly did my nails and borrowed Daniels shoes, running out quickly, I sighed as I finally reached the elevator. "So far so Good. . . "
I Took a deep breath as I walked out of the elevator and into the prom, no one seemed to see me enter, I pushed my way to the middle of the dance floor and saw him finally, about two inches taller than me without heels, he was about my height now, I slowly made my way over and started dancing near him, hoping to get his attention. Finally I did as he moved over, slowly putting his hands on my hips from behind, as I jumped praying that it was his hands and not someone else’s, I smiled and started to dance, saying nothing until a few songs had passed and a slow one started, he asked me to dance, I nodded and put my arms around his neck, a moment later he started the questioning, asking who I was where I was from, why I was here. I lied to all of his questions.
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. . I was Toni, I was from a town a few miles away, I had a date but he left like an ass and I decided to stay, all of which were told in a fairly feminine voice.
As the prom came to an end, he told me that he had a room, that he had planned on having a party in, but would rather just me come up with him for a bit, I smiled and agreed, faking a sniffle, pretending I was upset and vulnerable. We rode up the elevator and I smiled, scooting close to him as he put his arms around me, my eyes closing as I kissed his neck and cheek gently, his hands roaming to grip my bottom tightly as I jumped and kissed his lips.
The elevator then opened to an older couple glaring and stepping on, going to the same floor that we were, we both smiled as they mumbled a few things, obviously derogatory towards 'us kids'. We stepped off before then and walked to his room, walking in I kicked off my shoes and sat on the bed as he took off most of his tux, besides his pants and t-shirt. I smiled at him, with my painted lips as I kissed him again, rubbing my hand down his muscular chest towards hi crotch, running my painted fingernails over his crotch I moaned in his lips as I grasped his semi hard cock, rubbing it up and down as it sprung to attention, to its full 8 inches, just seeing it made my own tiny cock strain at their pantied prison.
I moaned as I felt it strain and slowly got to my knees, his hands resting on the sides of my head as I Slowly licked up his cock, wrapping my lips around his head as he let out a loud moan, and I slowly slid my lips down his cock, pulling them up, rubbing my tongue along the underside of his cock and around the head. "Mmm. . . Your so fucking good" He moaned as I continued this. After a few moments I stopped and looked up.
"I have to tell you something Derek.
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. . "
"What is it?. . . Is something wrong?"
"Y. . . Yes. . . "I turned away blushing. . . "I’m not who you think I am Derek.
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. . "
"What do you mean I just met you Toni. . . "
"No you didn’t. . . I've been in your history class all year. . . And. . . I.
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. . I saw your cock tonight in the bathroom and just had to have it. . . "
"W. . Wait. . . So. . . I should have seen it, especially when you turned around and blushed in the bathroom. .
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. " Smiling he put his hand under my chin and kissed me, as a few tears ran down my cheek.
"You aren’t mad?" He shook his head and smiled.
"I always thought you’d make a cute girl. . . And you do. . . "With that he threw me down on the bed and got on all fours over me, pushing the dress up over my crotch, as he pulled my panties down and threw them off, my four inch cock springing to life as he did, he blushed some and laughed as he saw my dick, my face turning bright red as he spoke. ” Its fine. . . A girl should have a big ol' dick anyway. .
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. especially not one that’s gunna be my new girlfriend. . . "My eyes lit up as I smiled and hugged his neck, wrapping my legs around his waist as he pulled out a tube of KY jelly, smearing it on his dick, then a little on my hole as he put a finger in, then two. He pulled them out, as he slowly replaced it with his the head of his cock, which slowly turned to his whole eight inch shaft, filling my rectum.
"Oh. . . Derek. . . !" I moaned as I bucked my hips, holding onto him tightly, my dildo was only five inches, and half as thick, slowly he started to move, pulling out, then pushing back in hard. He did this for a few moments before speeding up, tensing after a few moments of this as I felt his warm sticky cum fill my ass. I let out a long sigh as my eyes closed and we fell asleep like that, Daniel never did get her dress back, it was kind of messy when we got done, so I paid her back for it, I wanted it as a souvenir as my first bisexual encounter, and of my first boyfriend.
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To be continued, leave me some feed back, if it gets good ratings I'll continue. . .
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