Transgender Games

I would like to take this opportunity to thank

Wkd_Macey

for her invaluable contributions to this, my first full story fit for publication. She's an amazing author in her own right, and was amazingly generous with her time in bringing this about. If you have a love for extremely well-written, fleshed-out characters that also happen to have vividly-described encounters, you need to check out her stories.

Much like WM, I am a huge fan of the build-up, so be aware that each chapter builds on the previous in terms of both story and eroticism. There's definitely going to be at least one sex scene per installment, but don't expect the main character to be on her back from the get-go right up to the end.

The story you are about to read is true, in so far as it all totally happened in my head. ;)

Transgender Games: CH 01

Taking a Chance.

So, I was sitting in this coffee bar, minding my own business, when a group of four women came in. They were laughing, joking and generally being a bit raucous. Not so loud as to disturb the other customers unduly, but boisterous enough to make themselves something of a spectacle. I looked up from my laptop and happened to catch the eye of one of their number, a tall, exotic-looking woman. She appeared slightly older than the others, but that may have just been my impression, as she carried herself differently than the others; her stride had a predatory pace, as opposed to the rest of her group who had more bounce to their steps, but perhaps I over-analysed the situation. She looked at me, half staring; it was almost a glare which made me feel quite uneasy before I finally looked away.

I had seen them in the cafè before, about a week earlier, but on that occasion they had been very quiet and I would have hardly noticed them at all were it not for the little blonde sitting among them. She appeared at first sight to be very young to be with a group of women in their mid-to-late twenties, but I was to discover that she was not only their equal in years but she also was married with two young children in middle school. On that occasion, the others were paying her an extraordinary amount of attention, and I remember imagining that they were a group of hunting lesbians and perhaps she was their latest catch. In another life, I could see myself as the exotic woman; the alpha of the pack, leading the way back to the den after a successful day of prowling the wilds, their catch in tow. In reality, though, I was only a spectator to their celebrations.

I paid them little heed at the time, other than the occasional glance up from my work to discreetly monitor their progress with the blonde. Before long, I sensed that they were also watching me, so I finished my coffee, packed away my laptop and left, taking great care not to look back in their direction as I did so, lest I embarrass myself. Even so, I believed I could feel their eyes on me. Perhaps it was just my imagination again, or maybe just a tiny feeling of guilt that I should have been bolder and stayed put. At the very least, I chastised myself, it would have been interesting to see if the blonde was a willing participant in the group's efforts to include her. Even that much, however, was too assertive for my liking. At that time, anyway.

I should really introduce myself.

My name is Janice and I work as a freelance proof reader for a small, local publishing house. The editor is Alfonso, although he hates the name and insists on being called Alf. Alf is a short, stocky little guy, almost twenty years my senior, balding, with glasses, and not particularly well endowed as I was soon to discover. He would give me manuscripts to read on all manner of boring subjects like insects, cooking with rice, railways, walking, gardening, bricklaying, etc. Anything that he didn't want to bother with himself, really. If something more interesting or juicy came in, like spy novels, thrillers, or anything the slightest bit raunchy he would keep those works back for himself. While he may not have overcompensated for his, er, "shortcomings" in the typical fashion of men in his situation, his I-get-the-best-submissions policy was far more irritating to me; if he had simply bought some obnoxious sports car or other stand-in for a more impressive tool, then life there would have been bearable, at least.

I'm on piecework and I can usually get through about three or four manuscripts a week if I put my mind to it. I say "manuscripts", but they're all in machine-readable form these days; far better as there's so much less weight to carry around. Just lately though, the stuff has been so earth-shatteringly dull that I've been struggling to do more than two a week. I needed to do more or I would starve. At first, I thought maybe he was testing me, seeing what he could have me proof that would be *so* dull that it would literally bore me to death. On the morning of the day I would say marked the turning point in my life, he forwarded on to me a work that managed to out-boring everything else he'd given me to that point; some "dead in the head" author had written about the fascinating world of mollusks. Mollusks. And I tried, really I did. It was when I found myself unable to get through even the author's preface, where he failed spectacularly at convincing me that I would be "dazzled by the denizens of the damp", that my subconscious self rebelled and before I knew I was going to do it, I had already opened the door to Alf's office, stuck my head in, and asked, "Isn't there something more interesting I could read?"

There followed an awkward moment where our eyes met as he looked up from his laptop, which, I noticed, he was operating with only the one hand. He quickly sat up, bringing his other hand into view and patting/rubbing his chest in what he clearly hoped was a casual manner. The expressions on his face started off with alternating confusion and embarrassment, but there were hints that darker expressions would take their place once his brain recovered from the sudden shock of my interruption. I could have frozen in place right then, and pre-mollusk me would have done, I'm sure. My own mind was quicker, though, and flashed a scene of my body, lifeless, lit in the glow of a screen showing pages detailing the feeding ranges of Aniva Bay scallops ("...helpless pawns in a harrowing, Russian-Japanese, territorial dispute!"), and I took control of the situation in a way I could not have imagined prior to that point.

I know his eyes are always on me when I come into work, so I tend to wear something to tease him a bit. It's a bit wicked of me but I simply can't resist giving the poor, sad, sap a hard-on if I can. It was my only way of asserting myself, I thought, and to show that despite his complete control over what I could read, he was still subject to my wiles. My breasts are pert and firm so I never have to bother with a bra, and as I quickly sidled in the rest of the way into his office, I could see him watching them jiggle around inside my blouse; clearly, the anger he was building was overriden by whatever perverse thoughts that were now centered on my tits. I've been told in the past they look like two little boys fighting in a sack. He looked me up and down, not caring that he was being completely obvious in undressing me with his eyes. I leaned forward with my hands resting on the front edge of his desk, allowing him a decent view of my meagre, yet still eye-catching, cleavage. With the top two buttons of my loose-fitting blouse undone I knew he wouldn't be able to resist peering inside at the sight of my breasts hanging down enticingly.

He glanced up to see me smiling down at him, which seemed to finally dispel the awkwardness of my catching him in a private moment, then his gaze returned to the open neck of my blouse. "What sort of things would you like to read"? he asked slowly, savouring the moment.

"Oh, I don't know" I said in a wistful, light tone, standing straight whilst fiddling with the third button, which I subsequently "failed to notice" had "accidentally" fallen open. "Something a bit more exciting? A thriller maybe, or even something raunchy, perhaps? There must be someone writing better stuff than 'The Secret Life of Mollusks'" I laughed in what I hoped was a suggestive manner. I leaned forward again and his eyes remained transfixed on my half-open blouse. He could probably see my belly button now, between the dangling breasts.

I'm almost thirty, but I'm quite young-looking for my age. I'm altogether short and petite; just five feet tall in my bare feet, and size eight. I wear my dark hair pleasingly short, which adds to the effect of the rest of my qualities and overall makes me look so young that sometimes I'm even asked for ID when I buy drinks. Not that I have to buy my own drinks very often; I can usually find someone gladly willing to pick up my tab. That doesn't mean I'm a loose woman at all, or a flirt, and I'm certainly not a prick-teaser. If a guy wants to buy me a drink that's fine. I'm happy to let him most of the time. I make no promises, and if he tries to get too close I just say "Sorry, I'm with someone at the moment, but thanks for the offer." and I'll tell him "I'm flattered." The truth is, an awful lot of guys are attracted to small, young-looking women. They will always scowl and rebuke the very idea of paedophilia in the presence of others, but given the opportunity to bed a woman who looks too young for a night of shagging, they will usually jump at the chance. I find it incredibly hypocritical, so of course I don't mind taking them for the cost of a couple of drinks if I can.

I realise that I'm presenting myself as someone who is rather forward, but the truth is, I'm shy, and my being bi-curious just adds to my general unease in social situations. I like men ok, but my ideal guy would be someone not much bigger than myself. Someone fresh-faced and gentle. To be completely honest, I'm probably a bit afraid of being with bigger men. I've always believed that, in general, size is proportional. The bigger the man, the bigger his, err... component parts. Because I'm so small myself, I don't think I would be able to take anything too big inside me, and I know that once the action starts I wouldn't be able to stop a big man if I felt it was too much for me. So I think my ideal male partner would be someone more like my size, I suppose. Not too tall and fairly slim; boy sized, I suppose you might say. Is that me being hypocritical now?

Alf was nowhere close to my possibly-hypocritical ideal, though, and it certainly wasn't my usual, shy self that was now thoroughly commanding the situation. He gulped.

"Suppose I did have something?" he said softly and thoughtfully. "Why would I give it to you when I can enjoy reading it myself?" he smiled at me. No, it was more of a leer. For the first time he was looking into my eyes, thinking, I suppose, that he could take advantage of the situation on his terms.

"Oh," I replied, "is that what you call what I just saw you doing? Reading?" my breathy delivery and slight smile turned what would have been a very sarcastic remark into a promising exchange. "I would be so grateful for something I could enjoy 'reading' just as much." I told him earnestly.

"How grateful?" he asked, and in his continuing effort to regain some control over the situation, he tried to speak in a much more masculine tone than his usual, higher-pitched voice. He might have pulled it off, too, if he hadn't startled himself at the unfamiliar sound of his own words.

I didn't reply. Instead I simply looked into his eyes and walked seductively around the desk toward him, my fingers slowly opened the remaining buttons down the front of my blouse. Once more, his eyes dropped and he wasn't looking at my face. He watched excitedly as the buttons gradually revealed more and more bare flesh, until the blouse was completely open down the front. Even then he couldn't see my breasts. Just the firm cleavage, my nipples still being hidden by the open front of the blouse hanging in place.

A part of me couldn't believe what I was about to do. There I was in my boss' office, about to prostitute myself to him for nothing more than a better book to read. I looked down to his crotch, expecting to see a massive bulge, despite my belief in "smaller gents make for smaller tents". Well, there was a bulge, but it wasn't all that impressive. My theory of penile proportions was, apparently, quite sound, and I was relieved that even if we did get so far as to actually fuck, I was in no danger of taking on more than I could handle. I tossed all caution aside, and guided his hand up to one breast as I swung my leg over to sit across his lap. His other hand moved instantly to my other breast and he squeezed them roughly. The broad smile on his face said it all; if I let him carry on in this manner, he would once again be in control, which meant a brief reprieve, at best, from the usual stream of boring work he doled out.

"Be gentle." I told him, slowly stroking his head as I guided his face toward the gap between his hands. He complied almost immediately, and switched to a more massage-like, firm pressure and I felt my arousal increase at the first warm touch of his lips against the bare flesh between my breasts. I was pleasantly surprised at how well he took direction. I had never imagined myself with him before, but as he teased my nipples with his fingers I felt myself getting wet.

"Suck it for me." I ordered him, my breathing getting faster, as I cradled his bald head in my arms, moving slightly to one side. He took my nipple between his lips and began suckling like a little baby, still squeezing and fondling my other breast lovingly. His free hand rested on my side, then began stroking its way down to my waist then my hip. I closed my eyes and enjoyed the sensation of his lips and his hand stimulating me, until I realised that his other hand had moved between my thighs.

I wanted to stop him. As bold a move as it was for me to get that far, it started off as a tease and I intended to keep it that way, but because I was sat astride him, I couldn't close my legs, so I pulled his head back slightly and said softly, "No, no, naughty boy." but he took no notice.

His fingertips stroked up and down across the slit through the wet gusset of my panties, then tried to fumble their way inside the waistband. "Do you know what you're doing down there?" I asked him kindly. Thankfully, he never saw the bemused look on my face.

"Not really." he mumbled, unwilling to release my nipple from between his lips. I knew that he wasn't married, or even dating anyone, so his answer didn't surprise me at all, but by now he had got me wanting it too. I smiled and pulled away, standing on one leg to remove the other leg from the silky, lace panties whilst still astride him.

He watched with wide eyes and open mouth, in total disbelief as my bare, shaved, pussy came into view just inches from his face. As I resumed my position across his lap I guided his hand to the warm, soft skin of my now exposed labia, first cupping it in his palm to caress the entire area of forbidden flesh for almost a minute, then guiding his middle two fingers into me.

"That's better isn't it, baby?" I said through a long exhale, as his fingers slowly made their way into my tight pussy. Returning his lips to my nipple, I said "Now, baby, frig me until I come."

"When do I get to fuck you?" he asked, the words coming out coarsely.

"You don't, baby," I told him, "but if you're a good boy, I'll blow you."

For an inexperienced, middle-aged man, he seemed quite good at what he was doing. He noticed on his own that when he alternated between sucking on and flicking my nipple with his tongue, he was rewarded with soft moans and my chest pressing forward into his eager mouth. When he took the initiative to switch his attention to my other tit, he genuinely surprised me and I ground my pulsing pussy even harder into his fingers, until I felt the heel of his palm against my stiff clit. I was throwing myself into fully enjoying my new assertiveness, and it was all he could do to hold us steady in his chair as my hips thrust back-and-forth with increasing speed. He got very close to making me come all on his own.

In fact, he only needed one more instruction, "Baby, you're being so good, now I want you to bend your finger, just a bit, until you can feel a part of my pussy different from the rest." I could only see his forehead, wrinkled in apparent confusion, but he did as he was told and, miracle of miracles, found my G-spot after a little experimenting with the angle of the bend. As soon as he heard me catch my breath, and felt me draw his head even closer to my chest, almost suffocating him, he froze his fingers in place. I only had to adjust my motion to give myself a bit more up-and-down on his perfectly-positioned hand, and then it was just a matter of how quiet I could keep my escaping moans as I felt my tight hole clenching with an orgasm that surprised me with its strength. My shuddering body finally came to rest, and I half-opened my eyes to see him giving me a satisfied smile as if to ask "Was that good enough?" It was, of course, and by way of silent reply, I bit my lower lip suggestively as I nodded.

"Can you pass me a tissue from that drawer?" he asked, pointing to the middle desk drawer on his right.

"No," I told him, seeing my chance to establish control again; can't have him thinking that just because he made me come he was the one wearing the trousers, figuratively, at any rate. Shaking my head as I smiled a mischievous smile, I told him "You have to suck them clean." He hesitated. "Go on," I told him sternly, "you never know, it might be the best thing you've ever tasted. And if you do it for me, maybe I'll blow you." I tempted him.

Reluctantly he raised his slick fingers to his mouth, pausing to inhale. It didn't smell bad at all, as I knew would be the case. I'm a clean girl. I shower every morning, and it's never any hardship to pay particular attention to my sweet, little, pussy. Sometimes, I'm under the spraying water for twenty minutes or more. I must waste so much hot water, but what the hell; a fuck is a fuck, wherever it happens, and if anyone knows how to bring me off properly, it's me. Added to that, I hadn't been out of the shower for more than a few hours by that time of day so I was still completely fresh down there.

"Go on," I repeated, making my voice sound as authoritative as I could. He licked the tips of his fingers to test the flavour; given his limited experience with the opposite sex, I could only guess what he was expecting my juices to taste like. Clearly, though, he was not of a mind that it would be anything pleasant, because his face held an expression of disgust up until the very moment his fingertips met the tip of his tongue. "Oh, not so bad!" he must have thought, as a faint smile appeared on his face.

"All the way in." I told him. Finally, he obeyed. Before long, he was rather evidently enjoying it, and by the time he had finished there was nothing left for me.

"Do it again." I ordered. There was no hesitation in his movements, and I involuntarily shuddered with pleasure as he slid his fingers between my still-sensitive pussy lips. But as he raised his fingers to clean them, I grabbed his arm and directed them into my eager mouth. He smiled with a new serenity as he watched me devouring my own juices.

We sat like that for about 10 minutes, sharing my flavour, until at last I asked him, "Would you like your turn now?" He nodded silently.

"Ok. Now, I've never done this before so I don't know the signs." He looked puzzled. "I don't want you coming in my mouth," I explained. "Understand?" He nodded. "Be sure you do, because if it happens I'll put it all in yours. Ok?"