A Night to Remember Ch. 02

Happy Birthday to me...Friday April 24^th was my four year anniversary of joining Literotica.com, so as a special treat, four new stories in one go!

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Author's note: If you haven't read part one -- A Night To Remember -- that might help provide a little context :P this is a transsexual story about love, confusion and exploring a new world of sex. Enjoy!

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Sometimes, a distant part of me wondered how I could have ended up in a place like this, doing something so dirty, but I guess people do crazy things sometimes.

I'm Alex. I'm you're average 22 year old guy. I work hard at a dead-end job, I go out with friends, I watch bad TV shows.

A few weeks back I was at a Christmas party for my Dad's work, boring stuff as usual. When I finally managed to escape the place I found myself in the company of a beautiful, mysterious woman who asked for a smoke and gave me the quickie of a lifetime, which is surprising in a way, since I found out she actually had a cock.

Don't get me wrong, I'm not against gays or anything like that, in fact I think I'm fairly open minded, and she was a very stunning girl, but it was a little confronting at the time and I didn't really know how to deal with it other than to let her do her thing. She sucked me until I almost came and then rode me until I shot unprotected into her ass, which apparently was enough stimulation for her to cum as well. I felt strange afterwards, a mixture of satisfaction, confusion, shame...and even though I knew what she had between her legs the second she pulled those sexy panties back up and smoothed out her dress she was a sexy, long legged smoking hot girl once again.

I never got her number, or even her last name. all efforts at finding her were futile. I didn't just want to find her, I wanted so much more. I became obsessed with her.

Having no luck actually tracking her down, I fed my obsession with porn. At first I didn't really find what I wanted there either; sure there was a lot available but I had a particular taste, and it wasn't for the biggest fake boobs, or overdone makeup or anything like that, but the girls who literally looked like normal chicks who had grown dicks -- simple, average looking girls.

Luckily there were a few porn stars who provided what I was looking for, some of them had it in bits and pieces, others the whole package (no pun intended), and a lot who's early videos were better than their post-body enhancement later ones, I have to admit. I don't want to name names, but some breasts and lips looked better smaller and more petite.

Eventually I had a steady base of search cues that I could rely on if I needed to get off, which was good since despite my obsession with perfection my tastes seemed to change quite regularly. Sometimes I wanted cumshots, sometimes awesome anal scenes, and sometimes -- not knowing fully why -- I wanted to see a chick with a flat belly and huge boobs thrusting her hips behind somebody else for a change.

After a few months of looking through pictures and profiles, hoping I might track down Frankie, I did make one other useful discovery; I realised just how many other people like her were out there in the world. The problem now was whether I could find a completely new girl who matched what Frankie was able to give me.

And if I did, would I have the courage to tangle with the internet?

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Months of dating websites, hook-up pages and even a call to a nearby brothel that once used to offer shemales (none of them hang around anymore -- no pun intended there either), and I had come up almost completely empty. Oh I had a few hits, some chats with people here and there that led to nothing. Some of them offered pictures, and while I was appreciative they simply didn't have what I wanted. Some pictures were better than others, but of course I couldn't get those people to actually meet me, for one excuse or another.

Finally I had a bit of luck: I got an email from a nineteen year old crossdressing girl named Amy who had a very soft feminine pair of lips, long straight hair and a thin body, based on the few semi-revealing pictures she sent me. We talked for a long time, longer than any other person I had met online so far, and she told me she was getting more into crossdressing and shemale activity, and had the money to buy some sexy girly clothes if I wanted to go shopping with her. I was keen, but way too nervous to go that far so soon, so I told her that after a meet or two I'd see how I felt about that kind of public display.

I didn't hear back at first, but when she did reply I was pleasantly surprised. She told me how she understood my nerves, having only recently become more actively girly, and still mostly doing it in private. The more she talked the more I wondered if I could go through with meeting her face to face. In the end, Amy made the decision for me. She invited me to some swinging bar on the other side of town for a drink, so reasoning to myself that there was no harm in going to a place I'd rarely go to otherwise, I figured why not. Nerves twitching and my heart pumping a little too fast, I made my way out to meet a "girl".

After making my way through the mass of university students who seemed to haunt the bar I got a text from Amy telling me she was already there. I panicked, afraid that I might have walked past her and not even noticed. Eventually I made my way around the bar again and came across some gloryhole booths out the back. At the same time I got a text from Amy, telling me to go into one of them.

I found the number she indicated and went in, putting a few bucks into the machine that turned on the light outside the door and activated the DVD player, a porn scene starting up. I heard a tap on the wall next to me and looked over, seeing a small viewing window and a pair of pretty blue eyes staring at me. She was too short for her whole face to be seen through the glass but I knew it was her, even without seeing the top half of her face in the emails. She quickly disappeared from sight and a pair of red nailed fingers beckoned me through the gloryhole further down the wall. By this point all I had on my mind was Amy's big soft lips, and I was hard enough to slide my cock into the hole without a second thought.

Amy gave me an achingly good blowjob, the best I'd had in a very long time, her tongue and mouth dancing over my cock, her hand stroking me softly before speeding up when she licked me all over, and her lips sliding up and down my shaft, her quiet moans telling me how badly she wanted my cum. I finally sprayed into her mouth, her lips locked over the head of my cock until I was completely spent.

The only problem was that all I really saw of her was that she was wearing a brownish-purple wig, had pretty blue eyes and that her delicate, beckoning fingers which had poked through the gloryhole and tugged on my cock had dark red nail polish on. Beyond that I knew nothing about her, and she sadly left before I was cleaned up properly -- apparently a little too nervous to do much more herself, I later found out.

As wonderful and stress-relieving as it was pressing my cock through a hole in the wall into her mouth -- and she swallowed, by the way -- when I received further emails and pictures from her it was pretty clear that Amy was very much new to the crossdressing gig, with not so much as a single dress or skirt and no breasts to speak of. Yes she did have a cute feminine face, and as a girl she was very pretty, but she was clearly still a boy, and wouldn't be ready for what I wanted for quite some time.

I felt dejected. I couldn't wait for her and I wouldn't be able to give her what she wanted until she was ready. As hard as it was, I politely told Amy that she would have no trouble bagging a big, handsom guy and his long, aching cock that was a lot less obsessive than me, and although she promised to stay in touch, just in case I changed my mind, I can only assume she's doing just that right now. There was no way a slim, super young and super cute girl like her would stay unattached for long.

It seemed more and more like Frankie had left me wanting a lot from the world of transsexuals and crossdressers, and nothing seemed to satisfy me the way she had been able to. During the day I surfed the internet looking for shemales, transsexuals, crossdressers, traps, twinks, bubble butts and pretty much every other descriptive version of Frankie, and at night I dreamt of her riding me on a park bench, her perfect form, her ass, her breasts, her lips, her face, her eyes, and yes, even her cock.

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One particularly bad night I rolled over at 2am having not slept at all. I had waited all day for an email from a promising ad, only to get short one line reply from a girl named Rachel who barely told me anything about herself. I flicked over to my other account and saw no activity there either. Finally, even though I knew it was futile, I opened my second email account and saw no new replies from Amy, and her photos just wouldn't be enough tonight. The frustration was overwhelming, and although I had tried to ignore it after dinner, there was nothing I could do to relax, and I simply could not get to sleep.

Getting up, I padded over to my desk and opened my laptop. I ignored my email accounts -- they had left me feeling rejected, and pining for Amy to be ready sooner wasn't going to help me in the slightest. Not wanting anyone to hear what I was about to listen to, I plugged my headphones in, put them on, and started searching. At least in the porn world, I had finally reached a point where it didn't take too long before I figured out what I needed.

I watched the screen with lust as Bailey Jay sucked a long, hard cock into her mouth. Her babydoll face and big twinkling eyes were what attracted me to her, and I was in the mood for her playful attitude. Ruby red lips slid up and down, swallowing every inch of the cock as her hand moved down to lift her shirt, revealing her enormous tits. I quickly stroked my cock hard as I watched, and with a guilty, taboo satisfaction I watched her lie back, spread her legs and take the entire cock up her ass, her hand working her own smooth shaft gently. The camera looked down at her large, heaving breasts, her beautiful feminine lips, parting as she moaned, and her brown eyes stared back into mine, begging for it as I came hard, desperately wishing I could be the one fucking her in the ass.

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The next day I checked my email and found a reply that, at first glance, seemed average, but turned out to be my next big step into the world of transsexuals. It was from a girl by the name of Sarah, who had been looking for a guy to meet up with for a while now and thought I sounded like what she was after. She was 22, short and slightly curvy, and she called herself a regular crossdresser who had started transitioning to shemale and already wore her makeup and clothes in public. She had plenty of sexual experience and was very much a bottom, but was willing to please a guy any way he wanted, and if that included being the dominant one she had a 6 inch cock under her skirt.

Obviously it wasn't the first reply from a crossdresser I'd seen, and while I didn't immediately discount all crossdressers I had to admit that I was more interested in this one because she seemed to be a few steps closer to shemale than most. I was beginning to think I'd never find the kind of girl I was looking for, willingly acknowledging that Frankie had set the bar extraordinarily high. Nonetheless, I replied quickly that I really wasn't sure what I wanted in a person, was very picky and had struggled to meet the right someone so far, but I'd know it when I see it.

To my surprise, Sarah was all too happy to oblige my frustrations and in her next email she included her photo. It wasn't always that easy and I struggled with providing pictured of myself just as much as the people I talked to, so I already had a feeling this one was different. I didn't entirely know what to expect, but when I opened the attachments I was blown away.

I didn't know what to say. She looked super sexy, and even though I knew I had high expectations I was willing to bet she would meet most of them. I wrote her back and we organised to meet at the end of the week at the park a few minutes drive from my house, late at night when it was nice and dark. She promised to wear something girly that would show off what she had. As much as I wanted to ask what it would be, I decided to wait the two days. She promised to talk lots more about herself in the meantime, but warned me with a wink that she tended to get a little dirty. My cock was already throbbing.

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I pulled up to the park early, wanting to adjust to the scenery before I was joined by my mystery girl. My heart was pounding with both nervous energy and a strange sort of excitement. This wasn't like meeting Amy in the swinger's bar, this was something else, and I on top of everything else I actually felt a bit scared.

I got out of the car and wandered around for a bit, trying to calm my nerves while also seeing that the place was in fact deserted. The playground off in the distance was quiet and dark, and the few lights around the place left many darker areas where two people could get better acquainted with each other. I didn't know if I would want that level of intimacy yet, but then again I did remember to bring condoms and lube, and she told me she always did the same.

I heard a car down in the carpark and moved back there slowly, not wanting to catch her off guard and frighten her off. When I got there she was already out and walking towards me. My heart skipped a beat when I saw her.

It was dark, but I could see that she had her long light brown hair out and draped it down over her shoulders. She wore a light pink tight fitting top and what I guessed must have been a push-up bra underneath that showed off her small perky breasts exceptionally well. Combined with her smooth legs, a short dark blue checkered schoolgirl skirt and a pair of green trim converse runners she looked so much cuter than her pictures allowed. In those she was sexy, and it was all about her body's attributes. Here, in real life, it was all about her look, her style, and how she wore that feminine vibe like a second skin. She had a small black backpack over one shoulder and when she saw me she stopped a few steps away she stood in a relaxed pose, seeming not in the least bit shy or interested in hiding herself. She wasn't thin, definitely not chubby either, but had just the right shape and curve, and what I liked about it was that she didn't let her bones poke out like some of the "girls" out there. Her eyes were a piercing green and her lips were ruby red, and they had a faintly alluring smile on them as I closed the distance.

"Hey," I said, trying to act casually.

"Hey back," she said with a wink. Her voice was feminine enough, and only knowing what she had between her legs let me see and hear the faintest traces of who she used to be. She gestured to the park.

"Did you want to go for a wander? Maybe find somewhere comfortable?" she asked me. I nodded and she walked off, leading the way with her round bottom swaying slightly in front of me, blue skirt fluttering against her smooth legs. I followed that mesmerising ass deeper into the park before we found a small bench in a patch of soft, green grass. Sarah sat down and beckoned to me, patting the bench next to her, so I sat with her, our knees turned to face each other.

"Am I what you want?" she asked me, a bit hesitantly. With the adorable exception of a few freckles across her nose she didn't seem to have a blemish on her, her skin so smooth and creamy coloured that she could have been painted. Her eyes bored into mine as she waited anxiously to see if all that she was could be good enough for me. I could feel the sexual tension between us already. I wanted her alright, and I could tell she wanted me to be pleased with every part of her.

"You're not what I was expecting," I said, causing a flash of doubt to cross her face. "But I'm definitely very happy to meet you. You're even better looking than your photo's let on." Her expression changed from one of fear to relief and joy as she took my hand and rested it on her knee. I felt her fingers on top of mine and could only think that she was a girl, completely and utterly. Her skin was silky smooth, and very soft. Together we moved my hand up and down her thigh, her breath getting quicker as my fingers brushed further up her inner thighs, just underneath the hem of her schoolgirl skirt.

"And...this doesn't bother you?" she asked me. I shook my head.

"No...well, I don't think so. I mean, I asked you to see me, didn't I?" I said timidly, starting to feel a bit nervous. I think she could see that, because before I could say anything more she leaned forward and kissed me.

Her kiss was different; hot, wet, spicy, and a little bit light, as though she wasn't sure what I would do. We parted just a bit and when I didn't pull away she kissed me again, a little harder this time, and I kissed her back with the same intensity. Just like that I was back in Frankie's arms, but this time it was someone else, someone different in her own unique way, and that made it feel all the more taboo. We kissed for ages, sometimes softly, other times harder, her tongue finding mine as her hands moved up my chest and around my neck, pulling me to her.

She kissed me as though all the frustration and lack of anything or anyone for the past few months had been her entire life, clinging to me and revelling in the contact between partners. Moving slowly, one of Sarah's hands trailed down the side of my body to my crotch, rubbing the bulge that was growing in my pants with every minute I spent with this girl. She pulled back from kissing me and smiled, licking her lips.

"Someone's feeling excited," she murmured. I wondered if underneath that skirt she was also getting an erection, but slender girly fingers pulling my zipper down banished all thoughts from my head. I watched as this sexy, adorable young girl winked at me as she quickly leaned over and gave my hard, throbbing cock a long lick, her eyes locked on mine. It was amazing to see. I felt her tongue sliding up and down my shaft, getting it nice and wet before she slipped it in between her ruby red lips, moaning once over my head and working her mouth down on me.

It was heavenly, and I ran my hands down her back and over her shoulders, stroking the back of her neck gently as Sarah sucked my cock. She was very, very good at it, using one hand to stroke the lower half of my cock while her head bobbed up and down as she sucked on the rest, making small moaning noises and wrapping her tongue around me. She flicked the tip of her tongue over my head and dragged her lips down the side of my shaft to keep it nice and wet, her gentle yet firm grip pumping me all the time.

Her hair smelled like flowers and her skin was amazingly smooth, and as she got more and more into it she took my hand in her free one and led me to her breasts, helping me slip my fingers down her top and into her bra cup. They were small, maybe a B cup if I had to guess, and were a nice round shape, not too firm or too saggy, and I wondered how she got them, a thought I quickly banished as her mouth slid almost all the way down to the base of my cock and she squeezed my hand around her breast, her nipple hard and wanting its own attention.

Loving every minute I spent with this girl, I gently rubbed one nipple and got a long moan of appreciation around my cock as Sarah sucked me off, my fingers roaming all over her chest. I was beginning to feel like I could cum from her blowjob skills alone, but as I started to thrust gently up into her mouth she pulled back, kissing the tip and stroking it fast, her spare hand rummaging in her backpack.