One in a Thousand Ch. 01

[NOTE: Recently, the number of people following me on Literotica crossed the 1,000 threshold. That amazes me and I'm happy that so many people derive some pleasure from my writing. To mark this milestone, I decided to publish the first chapter of a planned long story that's been percolating in my mind, "One in a Thousand". The significance of the title will become apparent only in later chapters. As always, remember that this is a work of fantasy; it portrays unsafe sexual practices. There's no need for people to point this out in comments. I think we can trust readers to know that fantasies are not blueprints for behavior. —Cyanlot]

Chapter 1: Crossing the Line

I suppose everyone wants to be special in some way. I am, but maybe not in a way that you'll envy. I think you should envy me though; I'm happy and satisfied with my life in a way I didn't know was possible.

This wasn't always true. I used to be a pretty normal guy: 30-years old, decent looking but not a GQ model. I'd dated off and on but never met that "someone special" and I really hated the dating scene. I usually hung out with guys I worked with, especially Matt, who was, I guess, my best friend. My friends were okay and I fit in well enough but I didn't really find these relationships rewarding.

I didn't like my work at all. Whoever thought that white collar jobs are what you should desire, never worked in a low level position in an insurance firm. I made enough to get by but never felt financially secure. I guess I was always one paycheck away from not being able to pay my rent.

Matt was wilder than me. He got me to try lots of things that I never would have tried on my own: hang gliding, skydiving, and things like that. When Matt would propose one of these adventures, as he always called them, I would usually be reluctant. But he was persistent and, ultimately, I came to trust that, even if I found them a little scary, I'd actually enjoy them and be glad that I had tried them.

But, even after I'd come to trust Matt's judgment about edgy adventures, I was really resistant to the one that ultimately, after I'd given in to his incessant nagging, changed my life.

"Come on, Eric," he pleaded when we were out at a bar and he first proposed this. I had flatly rejected the idea, but Matt pressed it. "It will be a hoot!" he said.

Matt's great idea was for us to go to a whore house together. I guess "whore house" isn't politically correct. Let's say, "brothel". Like me, Matt had never done all that well on the dating scene so we'd visited some of those before. Nevada does have some advantages over other states. But his new idea had a twist that I wasn't down with.

Matt had found a brothel that catered to guys—and gals, I guess, if there were any—who were looking for sex with crossdressers and transsexuals. "Cross the Line" was the name of the place. And my immediate reaction was that it was a line I wasn't interested in crossing.

But ever-persistent Matt wasn't to be dissuaded so quickly. He kept circling back to his proposal and finally sort of bated me into agreeing. He suggested that my reluctance was born of some sort of hidden fear that I had gay urges.

"What's the matter? Are you afraid that you might get turned on by a cock? Afraid it might turn you gay or, worse, reveal your hidden desires?"

He said it all jokingly, but it landed. He'd made a challenge and I wasn't going to pass on it. So, with some ambivalence, I agreed to his plan. It turned out not so much to be "a hoot" as to be a transformative—one might say "seminal"—decision.

On the fateful Friday night that Matt and I were to cross the line, I was nervous. Matt and I hung out for a bit and had a drink in the common space where you can meet the girls—or I guess I should say, 'gurls'. We'd decided that we'd both go for shemales instead of crossdressers. "Cross the Line" offered plenty of both and they were conveniently labeled, we learned. The cross dressers wore a necklace with a pendant in the shape of a 'C' and the shemales had a 'T', which looked, ironically, much like a Christian cross, I thought.

As I looked around at our options, I realized that the markers were going to be very helpful. I really wasn't sure I could tell those who managed to trompe l'oeil, so to speak, with just clothing, wigs, make-up, and some prosthetic breasts from those who were in some stage—maybe a permanent stage—of transitioning. Some crossdressers are really good at it.

One of the trannies—Valerie, we learned—immediately struck up a conversation with us and, in a flirting and provocative tone, asked us what we two "gorgeous hunks" were looking for tonight. Characteristically, Matt was the one to pick up the conversation.

"Well, I don't know about my friend here," he began, "but I think I'm looking for someone like you." Valerie was good looking—tall, about 5'9", and slender but curvaceous—and she looked every bit the woman. I could understand his attraction to her.

"Well, then, you're in luck."

"Why's that?"

"Because I'm someone exactly like me, and I'm available," Valerie said flirtatiously. Then, turning to me, she said, "What about you, honey?"

I wasn't quick enough on the uptake, I guess, because Matt butted in to speak for me.

"You know, I was lying when I said I didn't know what my friend wanted. I do—maybe better than he does, Valerie. He wants someone like you, too—that is, if there's anyone else who can compare."

"Oh no, honey. I'm unique—sui generis. But, my friend Kiera is a real cutie. I'll bet your friend will like her. Let me get her."

With that, Valerie walked off to another room. As she sashayed away, I realized the degree to which she'd mastered every detail of feminine behavior. She walked with a subtle sway of her hips that would be the envy of other women and the focus of men's attention.

When Valerie returned with Kiera, I was floored. Kiera was a stunner—at least in my eyes. She had dusty blonde hair down past her shoulders, hazel eyes, and an adorable cleft chin. She was slender and not as voluptuous as Valerie—more of a girlish figure. Her breasts were small and high and perky. I was never a big-breast man, though I had always been a big breast-man, so I found Kiera's figure very much to my liking.

I guess I wasn't doing a great job of concealing that because Valerie piped up with, "I see you like Kiera!"

"She's great," I managed to say, blushing I'm sure.

And so it was set. Matt and Valerie left for one room and Kiera led me to another. Once in the room, I was on my own. I felt awkward and didn't really know how to proceed. Fortunately, Kiera was a pro.

"So, Eric," she said in a calming tone, "is this your first time?"

I started to sputter out a denial that was based on my interpreting her as asking if I was a virgin

"No, silly," Kiera said in a tone that made it clear she wasn't making fun of me. "I mean, is this your first time with a girl like me?"

"Oh, yeah," I managed. "It is."

"Well, no worries. There's a first time for everything and I think you're going to like it." She paused, "You like me, don't you? I mean, you find me attractive, right?"

"Oh, yeah!" I said, maybe with a little too much enthusiasm.

"Good, we're going to have a great time, Eric. Just relax and let me know what you like."

I didn't answer right away so she went on. "I mean, do you like it like a date or something or would you rather get right to the nitty gritty?"

And, again, I didn't know what to say. If the "like a date" meant kissing, that kind of creeped me out. I mean, as much as she attracted me as a female, when I thought about what Kiera was packing between her legs the idea of kissing her was kind of a turn off.

My hesitation was answer enough for Kiera, experienced as she was.

"Why don't you just sit on the bed for now?"

Kiera began unbuttoning her blouse slowly and very seductively. I wondered whether whatever time she'd lived as a male gave her some special insight into what was titillating for a man. Probably not necessary. I'm sure the gurls who worked here learned all the tricks and shared them with each other. Whatever the reason for her knowledge, Kiera certainly had it. She didn't overdo it, which would have destroyed the effect. She just knew how to command my undivided attention.

So I watched her slip off her blouse and reach back to unhook her bra. When the bra fell to the floor, I saw a pair of breasts as perfect as any I'd seen—not only in real life, which wasn't nearly as many as I would have liked, but on the Internet, which was thousands.

Her breasts were round and smooth with no sag to them at all. Kiera had small areolas and very pronounced nipples, which stood out like pencil erasers. I know many men would like larger breasts and I can admire big boobs, too. But, to me, the most beautiful breasts are on the small side—smooth, firm, and just large enough that you can't quite fit them in your mouth. Or, in brief, just like Kiera's.

When Kiera slipped off her skirt, my eyes were drawn immediately to her crotch. On a quick glance, you might not notice that she was packing there. Maybe she'd taped herself back or was just small. But, on closer inspection, there was a definite bulge there.

I didn't know what to think about that, or more honestly, what to think about my reaction to that. On the one hand, it was the thought that Kiera had a cock and balls that made me squeamish about kissing her. On the other hand, there was something fascinating about this very hot woman having a cock.

I didn't have a lot of time to think about it. Kiera walked over to me and knelt down between my knees. She ran her hands up my thighs past my hips, bypassing my crotch, and on up my abdomen, under my shirt. Her hands felt wonderful and I could feel my cock stirring.

Kiera dragged her hands back down my body, taking my pants and underpants with them. Then she moved her hands back up to caress my cock. With one hand on each side of my now rigid shaft, Kiera ran her thumbs on the underside of my cock. I moaned with pleasure thinking that nothing could ever feel better than her soft hands, gently caressing my cock, teasing it to grow even harder.

I was wrong. Something could feel better, as Kiera proceeded to prove. She brought her lips a mere millimeter from the tip of my eager shaft. I could feel the warm moisture of her breath on the sensitive underside of my cock. I thrust up in the hope of contact, but she backed away, intent on teasing me before pleasing me.

Kiera brought her tongue to the base of my cock and very gently, excruciatingly slowly, ran it up the length of my cock, making my cock twitch uncontrollably. Then she blew gently on the skin she had just moistened, causing my cock to twitch again, this time from the slight chill.

Finally, Kiera brought her lips to the tip of my cock and gradually took me deep in her mouth. Her tongue massaged the underside of my cock while her mouth worked on and off of my swollen shaft.

With one hand, she cupped my balls, massaging them gently while she worked her magic on my dick. And then I felt her other hand, somehow lubricated, slide between my butt cheeks.

I'd never really engaged in much buttplay when I masturbated and my experiences with women had never involved that at all. As I felt her fingers pressing into my crack, I felt conflicted. On the one hand, it felt like she was taking on a dominant role and I wasn't sure I liked that. On the other hand, though, as her fingers played with my butthole, it felt wonderful. In any case, I had no intention of pushing her away now that her lips were engulfing my cock.

Though I hadn't done much anal stimulation before when masturbating, I resolved to change that in the future. Kiera's finger, gently pumping in and out of my ass and reaching deep to massage my prostate felt amazing. That, and her warm, wet lips around my cock had me as full and rigid as I'd ever been. And that made her tongue and lips feel even better on my cock.

Kiera was thrusting two fingers in and out of my asshole while she worked furiously on my cock with her warm, wet mouth. When she jammed her fingers hard against my prostate, I exploded in her mouth—jet after jet of cum pulsing up my shaft and filling her mouth. I had my hand on the back of her head, thrusting my hips up in an attempt to plunge even deeper into her mouth.

I was bucking uncontrollably and screaming out, "OH, MY GOD! OH, MY GOD!", as I unloaded in Kiera's sweet mouth.

When my orgasm subsided, Kiera gently pulled her fingers out of my ass, her mouth off of my cock, and backed away. Looking up at me, she smiled and said, "How was that?"

How was that?, I thought. How was that?! Just the most intense, mind-blowing orgasm I could imagine. No one had ever made me feel like that before.

All I managed to mutter between gasping for breath was, "Incredible!", which seemed a terrible understatement.

"Good," Kiera said, apparently pleased with her work.

As I was still recovering, Kiera stood up and slipped out of her panties. As her small, still semi-flaccid, dick popped out of her panties, I stared at it with fascination. She was completely shaved and her small dick and ball sack looked ... I searched for the right word. All I could think of was 'cute'. Her dick and balls looked cute.

I wasn't thinking of this as being demeaning. In my mind, this was not denigration but admiration. Kiera's cock and balls were perfect. They were the ideal complement to her petite figure and her small, perky breasts.

Kiera clearly noticed the focus of my attention and could, I'm sure, sense my reaction. She took a step toward me, stopped, ran her fingers down over her breasts and down her abdomen. She put two fingers under her cock, raising it slightly toward me. I could see it begin to fill slightly and found myself transfixed by the sight.

She took another step toward me and her cock was just inches from my face. I felt a strange confluence of conflicting feelings. I'd never touched another person's cock and the thought of it frightened me. But I felt my mouth watering and I knew that there was no way I was going to resist my urge to take Kiera's sweet shaft into my mouth.

I leaned forward, opened my lips, and, for the first time in my life, felt a cock in my mouth. I was surprised by how wonderful it felt. My motions on her cock began tentatively but soon I was sucking her cock with ardor. I was no pro at this, as Kiera was. Compared to her, I was a rank amateur. (I remembered the origin of the word 'amateur'—one who engages in an activity for the love of it. Appropriate now!)

Amateur or not, I was doing a good enough job to have a dramatic effect on Kiera's cock. It swelled and hardened in my mouth. Its full length and girth wasn't much—maybe five inches long and not much thicker than a jumbo hotdog. But, when I pulled my mouth off of it and beheld it, wet with my saliva, it confirmed my judgment that it was absolutely perfect.

I leaned forward to take her beautiful little cock back in my mouth, but Kiera had other ideas. She pushed me back onto the bed. She pulled up my legs by my knees and spread them.

Oh, shit! I thought. She wants to fuck me!

This was a whole 'nother thing! It was a further, and scary, line to cross. Still, her finger had felt so good and the thought of her adorable little cock penetrating my ass held its attractions. In any case, I didn't have long to dither about it. I felt the tip of her cock against my sphincter and, after she dribbled some more lube on it, I felt it press against my asshole.

"Look at me," Kiera said as she increased the pressure on my sphincter, without actually entering me.

I had been looking at her, but not at her face. I'd been looking at the small, rigid dick as it approached its target. But now I looked up at Kiera. Our eyes locked as she looked down on me, flat on my back with my legs spread allowing her access to my bum. I saw her smile—not a smile of derision, but one of pleasure—as she ever so slowly pressed her cock into my ass.

Now I had another reason to appreciate the small size of Kiera's cock. Not only was it aesthetically attractive—just perfect on her—it was also a very welcome feature given my inexperience with ass play. I've read enough Internet porn to be familiar with the "it hurt so good" trope. But I was relieved that the pleasure that Kiera's cock was giving me hadn't needed to be earned by a lot of pain along the way.

And, indeed, Kiera's cock was giving me pleasure. There may have been no visible evidence of this, apart from the smile on my face. I wasn't getting hard again. I'd just shot every bit of my load, after all. But I was learning that sexual pleasure wasn't always about getting hard and stimulating your cock. I was finding a source, indeed a kind, of pleasure I hadn't known before.

Without interrupting her rhythmic stimulation of my asshole, Kiera began playing with my utterly limp cock with one hand. That had the effect of emphasizing in my mind the fact that the pleasure I was feeling wasn't from the stimulation of my cock.

Kiera could see the pleasure she was causing me with her cock and I could tell that her awareness of that intensified her pleasure, which in turn intensified mine.

"Push your hips up," Kiera urged. "Let me get deep in your ass."

I raised my hips, giving Kiera better access to my asshole and she pushed a pillow under me to keep me up at this angle.

Kiera got a good rhythm going and was thrusting as far into my ass as her diminutive cock allowed, she began urging me to beg for it. And, surprising myself, I did just that—and it wasn't mere playacting.

"Come on, let me know how much you want it," Kiera said. "Do you like my clitty in your boy pussy?"

"God, yes ... fuck me! Fuck me harder."

Kiera complied and soon she was spewing her spunk in my ass. Throughout this experience of losing my anal virginity, my own cock remained limp, flopping loosely whenever Kiera wasn't fondling it. As a man—one who formerly, at least, thought of himself as straight—I'd always associated sexual pleasure with my cock. For me, sexual gratification had always meant my cock getting hard and shooting its load of cum. But Kiera had taught me something new. I could derive sexual satisfaction, a sort of climax without ejaculation, just from a cock fucking my ass.

When Kiera pulled her cock from my ass, there was a moment of awkwardness for me. What did my response to having Kiera take my anal virginity say about me? What would Kiera think about me?

Her nonchalant demeanor put me at ease, though. We both got dressed without saying much. Kiera said something like, "That wasn't so bad, was it." Not a question but a statement. She was right. In fact, it was so good that it worried me.

Matt and I hardly said anything on the way home. We each said our encounters were interesting and left it at that, both of us ruminating in our own memories. I felt a little moisture escaping from my ass. Clenching my ass muscle made my memories of Kiera fucking me even more vivid.

Tonight had been very different from what I'd expected. I'd crossed a line, to be sure. I didn't really know what all lay in store for me on the other side of that line but I'd been so excited by my taste of it that I knew I'd be exploring it more.