After seven long years of sitting around, questioning my sexuality and fantasizing over the one thing I thought I could never have, I finally decided it was time to make a move. I was going to experiment with my sexuality, I was going to look for a real live hot tranny to meet up with and have sex with and hopefully I would enjoy it as much as I had always fantasized I would.

I had been interested in transsexuals since I was in high school, when a freak encounter with one of the computers led me to catch sight of something I did not expect to see. The computers were shared with every class that came into the room throughout the course of the day, and apparently, whoever had used my computer in the class before me had decided it would be funny to leave a picture of a very hot and very well endowed transsexual as the back-round on the computer. I scrambled to find a way to remove it, but could not figure out how to do it at all. I called on the teacher to help but he surprisingly had no idea how to do it either, go figure the teacher does not even know how to work the computers in his own classroom. I was forced to try and ignore this picture and just carry on with my work, I did the best I could but by the time I got home the image had been engraved into my mind and I spent the entire weekend thinking about it.

It eventually began driving me insane trying to figure out what it meant that a picture like that turned me on and I found myself searching up more images and films on the internet that involved these beautiful creatures known to the porn industry as she-males.

The first question that came to my head; was I gay,

I did not know because honestly I still liked girls, in fact at the time I had a beautiful girlfriend who I had been dating for quite some time and hooking up with her was still just as fun as it had been before all of this had begun. After quite some time of struggling with it I decided, it was best to keep this a complete secret and do my best to treat it as if it did not even exist...I tried but it was, easier said than done.

By the time, I was 18 I was convinced that this had to mean something; the thoughts had not gone away at all, and I was really becoming more and more anxious to experiment. I wanted to see what it felt like to be one of those guys' in the pics or movies being dominated by a hot woman with a big fat cock between her legs; I wanted to know what it felt like to be on the receiving end, to see it in real life and also to experience it for myself.

So here I was, 22-years old ready to finally go ahead and see what was out there in the she-male scene. My two best bets were either a gay club that was transsexual friendly or the City paper, although being unemployed and broke both of those options seemed a little pricey. There was a third option of course that I had not considered until it dawned on me at the last minute; craigslist. I typed in the website name in my browser and went straight to the casual encounters section and after twenty minutes of scanning through different adds with pictures included in some, I stumbled upon' the perfect match for me. Her name was Karlie and she was absolutely, beautiful, with long silky red hair, beautiful blue eyes an incredible body and a pretty, large cock too judging by the picture she had added with the post. She was 25-years old a couple years older than I was, and according to the add, she was simply looking for a night of good sexual fun no strings attached and no need for either of them to pay the other.

I immediately responded to the add sending a picture of myself, I was a bit too nervous to take one of myself in the nude so I just took one of myself without a shirt showing off my upper portion of my body and asked her to reply if she was interested at all.

To my surprise' she did indeed reply; she said that she thought I was hot from what she could tell and that she was very interested in me. I did not expect her to ask for a few more photos though until she asked that I send one of myself completely naked as well as a shot of my asshole as she apparently preferred to top during sex. That was fine with me, all the porn I watched usually involved the man bending over and getting, plowed in the ass by the she-male and this was what I was looking for mostly. I did as she requested and sent the photos to her and about half an hour later, she replied again telling me that she was more than interested and that she wanted to meet up as soon as possible.

We exchanged phone numbers, and I called her and we began discussing our plans to meet up and have fun together. She did not live very far from me and I still lived at home with my parents so I did not exactly want her to come to my house; we agreed that I would meet her at her apartment, which was probably only about a 20, minute ride by bus or car. I got on the bus and found that it was less time than I thought to get to her apartment and found her waiting outside on the front step. She was even more beautiful in person than she appeared in the picture she had posted on craigslist.

"You must be Tom?" she asked with a smile on her face.

"That's me; and your Karlie?" I asked shaking her hand. She leaned in and gave me a hug before leading me through the front door and up the stairs to her apartment, which seemed to be a pretty, nice place really. "Can I get you a beer?" Karlie asked me. "Uh, sure...do you have Coors light?"

She went to the kitchen and returned a moment later with a bottle of Coors Light and I twisted the cap off and took a long swig of it. I was a little too obvious about how nervous I was but Karlie did not seem to mind as she took a seat right beside me on the couch and smiled at me the whole time. "So I'm glad to meet you; you're really cute you know that?" she asked seductively as she began running her hand up and down my leg and I smiled trying to relax a little bit. "I can tell how nervous you are, so I'm assuming this is your first time. There's nothing to be nervous about, I love first timers and I'm always extra careful when I know I'm with someone whose' never done it before."

I smiled feeling a little relieved to know that, "Thanks; I'm glad to hear that." I said feeling a little more calm than I had before.

"So shall we get started?" she asked me and I simply smiled nervously and nodded my head, "Okay then." She said before leaning' in towards me, It all happened so fast and before I knew it her beautiful red lipstick lips were pressing against my firmly and her tongue slid into my mouth.

She tasted like strawberries and immediately I felt my cock begin to react to her touch as she ran a hand up and down my left arm. Our kissing became more passionate and soon enough we had made our way into her bedroom, she pulled my shirt off over my head and tossed it to the floor and seconds later she fumbled with my belt, undoing it and pulling my pants off.

Once she had gotten me completely undressed she began undressing herself and as she removed her clothing piece by piece, I felt my cock growing harder and harder. It was becoming increasingly difficult to resist the urge to jump her and fuck the hell out of her right here right now, but she wasted no time after she removed her jeans dropping to her legs and wrapping her warm wet lips around my hard cock. I moaned as she began sucking my cock like an expert, stroking it and playing with my balls at the same time; then she reached up running her hands up my stomach and chest to tweak my nipples and squeeze them lightly. I moaned again as I felt myself growing closer and closer to my orgasm when she stopped and stood up to kiss me again, teasing me by not finishing what she had started.

She broke the kiss and smiling at me seductively, she gave me a light shove and I fell backwards landing on her bed. She climbed on top of me and after a few moments of making out and her licking, sucking and biting at my neck and my nipples, she turned around so that now her ass was in my face and her huge cock was dangling just in front of my mouth. I inhaled the musky aroma of her ass and balls as she once again wrapped her lips firmly around my own cock and I had nothing better to do than lean up and wrap my lips around her cock; for the first time ever I was tasting cock and I had to admit it actually did not taste half bad. Here I was, in bed with a hot she-male in 69 with her sucking my cock while her ass and balls were, shoved in my face it was a dream come true for me.

After just a minute and a half, I felt my cock begin to throb in her mouth and I tensed up a little as she slipped a finger into my tight virgin asshole and started teasing my prostate while continuing to suck my cock.

Finally, with a grunt I exploded, shooting a massive load of cum into her mouth and Karlie swallowed every drop without any difficulties at all. I groaned, still sucking her cock as my orgasm began to subside and she released my cock still fingering my asshole as I sucked her off. By now, she had inserted a second finger into my ass and was spreading me wide open, I grunted in a mixture of discomfort and pleasure as my cock slowly turned hard again.

"You like that baby?" she asked seductively and I could do nothing but moan my approval and she giggled. "How about this?" she asked as she slowly and carefully slipped a third finger into my ass. I groaned, and grunted and writhed in pleasure and pain as she stretched my asshole wide open before sliding off, of me, her cock slipping out from between my lips as she got between my legs. She reached over to her nightstand and pulled out a bottle of lube and a single latex condom, tearing open the wrapper and pulling the condom out handing it off to me. "Hold this for a moment," she said as she started lubing up my asshole nice and good, making sure that it was just wet enough for her to slide into me without causing too much discomfort. Once she felt I was ready, she took the condom from me and smiled as she began unrolling it over her huge fat cock, then applied a bit of extra lube to her cock.

"Ready?" she asked me, "Yeah, whenever you are; just go easy on me." I said smiling as she pressed the head of her shaft against my asshole. She leaned in and kissed me on the lips probing my ass gently with her cock, I groaned at the feeling as she applied just a little bit of pressure and she popped right into me. I grunted in pain as a burning hot sensation ripped through my asshole and she began carefully easing herself all the way into me until she was, buried all the way up to the balls in my hot tight ass. It was anything but pleasurable at first but after a few minutes of her slowly thrusting in and out of me, warming me up, the pain began to subside and slowly it started to feel pretty, good.

Once she was sure I had adjusted to the feeling of her huge cock in my ass, she started to move a little faster fucking my ass with a little more force behind her thrusts. I was in missionary position with my legs wrapped around her and the sound of her balls smacking my ass echoed through her bedroom along with the sounds of our soft moans and grunts, and soon enough she was plowing my ass, slamming in and out of me, both of us moaning quite loudly.

I dug at her back groaning in pleasure as she pushed deeper into me now pulling me closer to her and really pounding away at my ass now. She pulled out all the way at one point and I was left with a feeling of emptiness, but it only lasted a moment before she plunged all the way back into me and my entire body gave a jolt; she repeated the same move, pulling all the way out first and then slamming straight back into me again. She continued this same action for about a minute until my asshole began clenching and spasming around her hard cock, and she knew I was getting close to my orgasm. My entire body was shaking now and we were both sweating as she started fucking the living hell out of me, the bed shaking underneath of us and finally I gripped the bed sheets and screamed, my asshole clenching around her cock and my entire body went into a spasm. It was the most incredible feeling I had ever experienced in my life and I never wanted it to end, but unfortunately it did not last more than a few seconds before my cock spewed cum all over the place and the orgasm slowly began to subside.

Once my orgasm had come to a stop, Karlie started fucking me long and hard again before grunting, she leaned in close biting her lip as her own cock started to throb inside of my asshole. She exploded and bit her lip hard as she started to cum deep inside my asshole, her condom holding her semen back as she moaned and kissed me passionately on the lips.

After a few moments, she caught her breath and shakily pulled out of my ass, my legs fell to the bed and she collapsed beside me, both of us exhausted.

That was it; my first time with a she-male, and it had been just about everything I had ever thought it would be, and so much more too.

She lay' her head on my chest and traced circles with her fingers over my chest for a few moments before glancing at the clock.

"It's getting kind of late," she said softly kissing me on the neck, "You can stay the night if you want too," she suggested. I thought it over for a moment or two then smiled and kissed her on the lips, "If it's okay with you then yeah sure." I replied.

She smiled and moved closer to me, pulling the blankets a little to cover us completely and warm us both up. It did not take very long before we had both fallen asleep, and I dreamed about more unbelievably fun sex with my beautiful new transsexual friend. We would have many more fun encounters ahead of us.