The Best Prom Ever

My eyes rolled into the back of my head as she took me in her mouth, all the way down to the base on the first try. She lingered there for several seconds, massaging me with her throat muscles, before she came back up for air.

I instinctively put my hands on the back of her head as she began to bob up and down on my throbbing manhood. It wasn't long before I felt the pressure build up in my testicles and I knew I was about to explode.

"Oh god, Mandi, I'm about to come!" I said as quietly as possible, still worried that we would wake her mom. The second I said that she pulled back.

looked up at me with an evil grin on her face. "Do you wanna fuck me?"

I couldn't believe my ears. I had never had my dick sucked before let alone had sex, and here was Mandi Thompson about to be all my firsts. How was I ever supposed to top that?

I nodded eagerly, not being able to muster a verbal response.

"I thought so," she said seductively as she came back up for a kiss.

We made out for a few seconds before she whispered in my ear, "You'll have to take me in the ass though, it's that time of the month."

I nearly passed out. All of my deepest desires were coming true on what was surely to be the most amazing night of my life. She sat up and pulled her dress over her head and tossed it to the floor. My hands instantly went to her ass, desperate to feel her bare flesh. I snapped the string of her black, lace thong in her crack and she jumped a little.

"A little eager are we," she said with a giggle. She then reached into her purse and returned with a small bottle. She squirted a large glob into her hand and began to rub on my cock slowly, making sure there wasn't enough stimulation for me to come before the fun began. She squirted another small glob into her hand and reached behind to rub it onto her bud. I held the string aside like a gentleman while I marveled at the sexy goddess that was straddled on top of me that was about to let me fuck her ass.

She then got up, turned around, and bent over on the couch, presenting her wonderfully sculpted ass to me. I eagerly got up and moved my cock to her awaiting hole. She reached her hand around and grabbed my dick and carefully began to feed it in.

At first I wasn't sure if it would fit, the hole seemed too small to fit my stiff member inside, but with a gentle push, my head breached her sphincter and she gasped. I froze, thinking I had hurt her, but she moved her ass backwards until I was fully inside.

It was the most amazing feeling in the world. It felt as though my dick was in a vice grip, but without any pain. She leaned back, her head was nearly level with mine and began to assault my mouth with her tongue. I reached around and cupped her breasts while beginning to slowly pull my dick out. When the head reached her sphincter, I slammed it back in and she moaned with pleasure.

While I continued to play with her left breast and continue my humping of her ass, I let my right hand drift down towards her crotch, desperate to at least play with her clit. Every time I got close, she would grab my hand and pull it back to her breast.

After about five minutes (I was surprised that I had lasted that long even), my balls began to tighten and I knew was going to come.

"I'm gonna come," I whispered into her ear a second time, praying she wasn't going to leave me hanging again.

"Me too baby, come in my ass," she moaned. "I want to feel your cum inside me."

I held out as long as possible, wanting for us to come at the same time, when suddenly her hand shot to her mouth as she tried to muffle a shriek. Her hole clamped tight around the base of my cock and I couldn't hold it in any longer. I exploded into her bowels and had to fight to hold back a scream of my own. I felt strand after strand of semen shot from the end of my dick into her, and soon I could feel it oozing past my cock and down her legs.

We both fell backwards, with her lying on top of me. We lay there for awhile, my still rock hard member inside of her. My cum was oozing from her ass, dripping down my legs but I didn't care at all. I felt content to just hold her like that. Finally, she sat forward and pulled my dick from her ass. She turned around to face me and I could see that she was crying.

"Hey," I said, reaching out to wipe her tears. I was shocked when she recoiled away.

"Jesse, I... I..," she stammered. She looked away as if trying to figure out how to say something.

I didn't know what to do so I just sat there, but couldn't help but think this was somehow my fault.

"Mandi, I'm so sor-"

"No, no, stop," she interrupted. "It's just... I haven't been totally honest with you."

I had no idea what she was talking about, so I stared at her until she continued.

"I'm not who you think I am," she said, looking down at her hands

"What are you talking about, Mandi?"

"Jesse, I've known I've liked you for awhile now. Like I said when you asked me to the prom, you were different. You always seemed so down to earth, unlike all the other guys at school, and I really grew to like that about you," she paused to take a deep breath, "that's why this is going to be so hard."

"What?" I asked.

She looked at me and another tear slid down her face. Her mascara was smeared all over, but I couldn't help thinking that she still looked beautiful, even as a raccoon.

"I haven't always been a girl."

I stared at her blankly while more tears welled up in her eyes.

"Please say something," she pleaded.

The only thing I could think of to say was, "What are you talking about?"

She looked down at her hands again, a tear dropped to her hands. She stared at it for several moments before answering.

With a deep breath she said, "I was born a boy."

I couldn't believe my ears. I felt like I had just been hit in the stomach with a 2x4. I suddenly felt dizzy and had to rest my head in my hands.

"Please, Jesse, just listen to me. On the inside I've always known I was a girl, but I wasn't born with a girl's body."

I stood up and started pulling on my clothes, suddenly very uncomfortable sitting there naked.

"Jesse!" she said, more loudly than she should have. She stood up and grabbed my arm.

I couldn't help but look at her... him, whatever it was. She stared up at me with those big green eyes, filled to the brim with tears. It was impossible to think of her being anything besides a girl. My eyes drifted to her breasts, still perkier than ever, and down to her slim, toned stomach and shapely hips. My eyes lingered on her crotch and for the first time, I noticed a small bulge in the front of her thong.

Another wave of dizziness overtook me and I was forced to sit back down. I had just had sex with a man, anal sex at that. Suddenly tons of questions flooded my mind. Was I gay? How could I not know she was a dude? What if my friends find out?

"Jesse, listen please," she grabbed my face with both her hands. Why did his/her skin have to be so soft and smooth?

"No one at school knows," she said, and a small wave of relief washed over me. "You are the only one besides my mom that knows. I understand if you never want to talk to me again but please, don't tell anyone. I beg you."

"I...," I tried to think of something to say, but my mind was completely blank. I had gone from having the night of my life with the girl of my dreams, to finding out she wasn't even a girl. Memories of the whole evening flooded my brain: our first kiss, the way she had rested her head on my shoulder, the cute way her nose wrinkled every time she smiled, and suddenly, as if I was hit by some sort of epiphany, that was all that mattered.

The more I thought of how happy I had been with her in my arms, the less I cared that she had a dick. It was weird to admit, but I really didn't care.

I looked back into her eyes and couldn't think to do anything but kiss her. I pulled her to me and we locked lips, but this time with no tongue, just pure, unadulterated passion. I wanted to hold her like that forever.

I felt her tears start to stream down my face and reluctantly, I was forced to pull away. I wiped the tears from her face, before wiping the ones on mine.

"Mandi," I started, wondering how I would come up with the words to express myself. "This has been a lot to take in. But despite what you've just told me, the only thing I could really think about was how you made me feel tonight. I was happier than I've ever been and tonight was the night of my life and I have no one to thank for that except you."

Her face lit up and again she came in for another passionate embrace. I had to pull myself away from her to get one last word in.

I couldn't believe I was about to say this, but sheer curiosity get the better of me. "Do you think I could see it?"

With a grin, she leaned back and pulled the front of her thong to the side, and out it popped. Not that it mattered, but it was quite small, perhaps an inch or two while flaccid. Before I knew what I was doing, my hand reached out to grab it.

Certainly the last thing I expected to be doing tonight was touching a penis other than my own, but I no longer cared. I rolled it between my fingers and heard a soft moan escape Mandi's lips. I looked at her, but her eyes were shut and her head had rolled back.

Suddenly, I was excited at pleasing my prom date in this way and I soon began to tug lightly on it. It began to grow in my hand and to my surprise, I was getting more and more into it. Without thinking, I bent in and gave her head a little kiss. I heard a small gasp, but ignored it, lost in the trance of pleasing my gorgeous date.

I licked the tip just as she had done and soon had it in my mouth. It was only about four and a half inches long and it fit easily into my mouth. I had always gagged on my toothbrush as I brushed my tongue, but this was not the case here, it seemed so natural, so right.

"Oh my god... Jesse," she moaned.

I was overwhelmed with happiness at the thought of giving her pleasure. I pushed my face all the way into her crotch until my nose hit her totally smooth pubic bone. I let it rest there, breathing in her scent as I repeatedly tried to swallow, thinking it would feel good for her.

I was right, as she soon said she was about to come.

I left her cock in my mouth, curious to find out what she tasted like. I tried to swallow two more times before I felt her body buck and the first strand hit the back of my throat, quickly followed by several more. The loads weren't very big, and I was able to hold it in my mouth after she had finished.

It tasted surprisingly well, a bit salty, but somehow very sweet too. I swallowed it down and looked up at her with a grin.

She immediately leaned in and we shared another wonderful kiss. Her tongue darted into my mouth, eager to find any lingering remnants of her seed.

When we finally separated, she looked at me in the eyes with the happiest smile I had ever seen. "Jesse, I think I'm in love with you."

At the rate my heart was skipping beats with this girl, I was afraid I might have to visit a cardiologist soon. But soon it resumed beating, if not a little faster than normal and I said, "I love you too."