cross-dresser

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.

I lay there on my side, with Sarah behind me her arm draped over me; we were in a spooning position and I could feel her hard cock pressing against me, probing my asshole. She started kissing me on the neck while playing with my nipples; I knew what she wanted. She was really trying to seduce me into it to. Until now I had, had no problems at all with any of the things we had been doing together. Hell, I had even sucked her cock and enjoyed that, but the idea of bending over and letting her stick her big fat dick in my ass…that sort of made me a little uneasy. I had seen a lot of anal sex videos, of course, all of those videos had girls getting’ fucked in the ass; I had never watched a gay porn in my life. Regardless, most of the videos I had seen the girl always made it seem so god damn painful; sure about midway through they would start to seem like they were enjoying themselves but it was the wait they had to endure until it slipped from painful to pleasurable.



She must have known I was nervous because she seemed to be trying pretty’ damn hard to convince me to give her what she wanted. I moaned as she sucked my neck and blew in my ear, sending chills up and down my spine. She was driving me crazy, and I was really trying to figure out if I wanted to go through with this or not.



“It’ll only hurt for a few seconds, I promise.”



She obviously knew what I was worried about; yet strangely, as she whispered that in my ear and ran her hand soothingly over my chest at the same time, I could not help but relax. It dawned on me then; I had only known Sarah for a day that was true.



However, Sarah was not really Sarah; Sarah was really Bryan and I had known Bryan now for two and a half years. By this point, I felt like I should be able to trust him pretty’ well, so what the’ hell was I so afraid of? As she continued pressing up against me I caved in and turned over onto my stomach’ and wrapped my arms around the pillow under my head.



She must have gotten the point because Sarah got up and reached for the lubrication and I jumped at the feeling of the cold stuff hitting my asshole. Then I felt something stiff but not big pushing into me; it wasn’t’ big enough to be her cock, and I realized after a moment it was her finger.



She worked her index finger deep into my ass and started massaging my prostate gland; I moaned as she rubbed up against it and I felt my cock start to go hard between me, and the bed. After a few moments of fingering me, she pulled out slightly and I felt my asshole stretch as she worked an additional finger back into me.



She now had two fingers knuckle deep in my ass, stretching me wide and playing with my prostate. It felt good but I also had this strong feeling of fullness and I realized, if it felt this strange just having two fingers inside of me how out of place was it going to feel when she actually started fucking me?



I felt her pull her fingers from me and she reached for the lube, applying’ more of it to my asshole and I heard an additional squirt indicating that she was applying some to her cock as well.



I took a deep breath and tried to relax myself; I knew from experience of fucking girls in their asses that if you were to tense then it would make it all the more difficult and painful. I braced myself, gripping the pillow as I felt her climb over top of me and she started running both hands up and down my back trying to help me relax.



“Are you ready?” she asked softly.



“Yeah; just go easy okay?”



“Don’t worry baby. I will.”



I felt one of her hands move away from my back, she used it to grab her cock and I felt the head of her big shaft pressing against my well’ lubricated and slight widened asshole. She applied pressure using her hand to guide herself’ into me; I felt myself stretching wider and wider and the feeling of fullness returned but a lot more noticeable. She inched her way into me and I felt as though the feeling were becoming overwhelming.



I bit my lip, shut my eyes and’ held my breath trying not to cave and give up to easily on this.



“Are you okay?”



“Yeah,” I replied.



“Do you want me to stop?” she asked.



I could tell by her voice she was not annoyed at all with me; she sounded more concerned and I could hear it behind her words that she really cared.



“No, it’s okay” I said. If she cared that much about me, then she deserved to enjoy herself so I would at least try to stick it out a little longer.



She continued inching her way into my tight asshole until I felt her full body weight on top of me and I could feel her balls pressing against me. She was all the way inside of me now and’ just staying there not moving an inch waiting for me to adjust to the sensation of her huge cock deep inside of me.



“You okay?” she checked.



“Yeah,”



With that, she lifted herself up just slightly, pulling her cock about halfway back and then driving it all the way back into me again. I gasped at the feeling of her moving out and then back in and then she repeated the same action a second time. By the third thrust, I could feel a strange hot feeling deep inside of my asshole with each thrust that she delivered. She was fucking me softly, making extra sure not to hurt me in any way and I could feel the dull pain beginning to subside as the pleasure started to kick in.



When she realized I was starting to enjoy myself, I noticed she had started to pick up the pace a little and was starting to fuck me just a little harder and faster. As my cock started to get really’ hard, I arched myself up off the bed slightly so that my ass was sticking out. She took advantage of my cooperation and grabbed me by the hips getting a firm grip; she started fucking me harder and faster now, breathing heavily as she slammed in and out of me.



I started pushing myself back against her to meet each of her thrusts. I could hear the sound of our sweaty bodies slapping together and my cock was throbbing by now; there was this strange sensation in the pit of my gut and it kept growing and growing. It felt like something huge was about to happen and I found myself praying that I was not about to have an accident from all this stimulation.



It felt like my insides were being twisted but in a good way if that makes any sense at all; I moaned and embraced the sensation and could not help but call out to her and beg her to fuck me harder.



“Harder,”



It came out in a low raspy voice and she almost didn’t’ hear me.



“What?”



“I said…harder…fuck me harder!”



“Tell me what you want me to do baby,”



“Oh god…agh, ugh, ugh, fuck’ me harder!”



She did just as I asked and started really pounding away at me now; the bed shaking underneath of us making the familiar creaking sounds of a couple having some really intense sex.



We had thin walls and I was sure by now at least one of our neighbors could hear what was happening. The problem there was they would hear me begging to be’ fucked harder instead of a girl uttering those words, and I was sure that later on one of my neighbors would probably be giving me an odd look when I ran into them.



I gasped as that twisting feeling over took me, and the tip of my cock started to burn as the room began to spin. I’m’ not sure how to describe the feeling really.



It felt like my asshole was squeezing her cock, clenching and unclenching over and, over again. The spasms became more powerful and as they did, my cock started to shoot a hot load of sticky cum all over my bed sheets.



“Oh shit,” I moaned loudly.



Sarah was pounding me now and now that I had reached my orgasm, she could stop holding back on herself. A few more powerful’ thrusts and’ grunting and moaning and she buried herself, balls deep in my asshole and exploded. Pumping me full of her cum before collapsing on top of me and we’ both sank into the mattress my face buried in my pillow.



We were out of breath and both of us were covered in sweat, exhausted and I actually felt kind’ of hungry. I could feel her cock starting to go limb inside of me and she pulled out rolling over and dropping back on the mattress at my side. We lay there for a few minutes, just trying to collect our thoughts before I turned over and smiled at her. She smiled back and moved closer to me, resting her head on my chest as we finally relaxed and managed to catch our breath.



“That wasn’t so bad was it?” she asked



I laughed, and ran a hand through my hair staring up at the ceiling. “Felt pretty fucking good,” I said. I could hardly believe it myself but it was the honest’ truth, I really had enjoyed every minute of what we just did.



We must have drifted off after a few minutes because I lost track of time and when I woke, I glanced at the clock and was surprised to see that it was almost 9:00 at night. We had slept practically the entire day after our little fuck session ended and I was starving now.



I sat up on the bed and that’s’ when I noticed Sarah wasn’t’ beside me anymore. I rolled out of bed slipped into my boxers and made my way out into the living room to find Bryan sitting on the couch watching TV.



“I see your’ awake finally,” he said smiling at me.



“Just woke up; I’m starving’ to.”



“I made a sandwich about two hours ago; we can order pizza if you want.”



I grabbed a few of the menus that we kept in the kitchen drawer and after a few minutes, we settled on the closest pizza shop that we could find and ordered a large pizza with extra cheese. I sat down on the couch while we waited for the food to get there and could not stop thinking about what we had done earlier and the night before.



All of this was so fucking crazy, last night there was kind of an excuse seeing as we were both so drunk and all; but today we had been completely sober and that had not stopped us. What scared me the most was that I had enjoyed all of it more then I had ever enjoyed any previous experiences of my life.



This had been some of the best’ sex I had ever enjoyed; so what did that say about me if the best sex I had ever had was with another man who liked dressing as a woman? I had no idea what was in store for me or Bryan/Sarah or our future for that matter.



I just knew that right now the feeling of euphoria had worn off and now I could feel the head ache of confusion starting to kick in.

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