Transgender Games Ch. 01

PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

"Ok," he agreed. I shuffled down under the desk and reached inside his still-unfastened pants to gather the stiffy from the folds of his fat belly and his underpants. I'd never seen one before, not close up anyway, but it did look disappointingly small. Only about four inches at the most. Short and stout, like its owner, and barely enough to get a proper grip on, small though my own hands were.

I'm not a virgin, but both of my previous encounters were in almost total darkness, and although I'd held one properly only once before, I knew it must have been bigger than this. I say "both" previous encounters. Really, there were three but I'm not counting the first when I was still at school. I was in the third year of senior school and he was in the fifth year. We were among a group of friends and we were playing Dare. My dare was to choose a boy and put my hand down his pants. I chose him, knowing he was a really shy lad, and he said he'd only let me do it if he could do it to me, too. I had to agree or I would lose my dare, but I suddenly worried, as I had never had to before, whether I was fresh enough "down there". Anyway, his member was tiny, and I suspected I had found the reason for his shyness around us girls. Even so, I told the others it was the biggest I'd ever touched, which was perfectly true at the time, and it saved him humiliation. Well, he *was* quite sweet, and as he was my first, I couldn't be entirely sure his was *unusually* small. From then on though, for my own part, I always washed myself thoroughly down there to save future embarrassment and worry.

I pushed that memory from my mind, stifled a laugh, and looked up at Alf smiling back down at me as I closed my mouth over his bulging tip. I was so glad that he too was a clean person. I had only just begun to tease the tip of his cock with my tongue when I felt his hand tap the back of my head. "He can't be coming already?!" I thought. Then I heard his secretary say, "Oh, I'm sorry. I thought I saw Janice Lane arrive."

"It's ok, Sandra, she did come earlier." he told the woman, and again I had to stifle a laugh. Call my reaction juvenile if you like, but I'm sure it was literally the first time he had ever had the opportunity to use a sex pun, appropriately, and I think that deserved a bit of mirth.

"Can I get you a coffee?" she asked, and it was clear that there was more to her inquiring tone than beverage service.

"No, nothing, thank you, Sandra. I just need some time alone to think." he said.

From my position, on my knees under his desk, I couldn't see her reaction but as she said "Very well." her tone was undoubtedly still one of question. Not that I could blame her; Alf was not known as a man who took time to make carefully considered business decisions.

"Pass me a few tissues." I whispered as I heard the door close. He did so, and I set about the task of giving him what may well have been the first female-assisted orgasm of his life. Honestly, I could not say anything of note about this part of our encounter, good or bad. It was neither the quick-to-finish, "it happens to everyone" awkwardness I feared would end with a split-second's warning between the start and finish of his orgasm, nor a never-ending slog with one or both of us giving it up as a bad job. I have a general understanding of what makes for a good jobby, and Alf was clearly enjoying my by-the-book approach (tease the tip, stroke the shaft, fondle the bollocks, etc.) Finally, not to belabor the point, but his size certainly made it easier to "deep-throat" him to his climax. At the critical moment he tapped me on the shoulder, confirming my suspicions from the sounds he was making that all my hard work was about to come to fruition. I wrapped a wad of tissues around his tip and let him deliver the load and soak the wad without getting a drop on me.

"You don't happen to have a small poly-bag I suppose?" I asked, "And perhaps a few more tissues?" I added. He provided both in a moment, and it made me wonder why he might have a supply of small sandwich bags in his drawer with the tissues. I reconsidered asking, even jokingly, because I honestly didn't want to hear him attempt to answer in a manner he thought would encourage future escapades like this.

"Now for dessert," I told him. I pushed his chair back and wriggled up to stand between him and the desk. Pushing aside his laptop, I rest my buttocks on the edge of the desk, leaned back with my hands behind me for support, and raised first one foot then the other to rest my heels on the edge of his desk. Now I had my legs spread wide in front of him and all that lay between him and my bald, bare pussy was the hem of my pleated skirt. He pushed his pants down and held his meagre, limp, member, looking both optimistic and disappointed at the same time.

"It's ok, baby," I whispered softly, "you're not going to fuck me. You're going to eat me." I smiled. He looked at me, unsure of himself. "Don't worry, baby," I soothed, "I'll tell you what to do." He smiled nervously. "You remember how you kissed these for me?" I asked, fondling one firm, ripe breast with my free hand. He nodded. "Kiss my leg the same way." I told him. He leaned forward. "There," I instructed, touching a point on the inside of my thigh, close to my knee, "use your tongue." I told him.

He began to kiss and lap, slurping at the salty flavour of my bare flesh. "Oh, that feels good," I told him, stroking his head with one hand whilst supporting myself with the other. "Now, work your way down to my hip." I moaned. He moved quickly. "No, baby, no. Take your time." I breathed out my demand huskily. I played with my breast as his tongue teased me, and the closer he went, the wetter I became. My pussy is small and neat and my labia plump, and puffy, looking almost virginal. I could see him about to throw caution aside and close his mouth on it so I stopped him by saying, "Now, do the same to the other side." trying, and failing, for the same husky delivery as before, but the increased urgency in my voice seemed to please him, giving him a new measure of confidence in his ability to drive me crazy.

This time he was more dominant, moving quicker toward his goal. "Slowly, baby," I pleaded, but he wasn't deterred. By the time his lips reached the very top of my thigh I was almost crying out for it. I imagined his inquisitive secretary with a glass up against the wall. She knew I was in there with him. She had seen me arrive. I was quickly losing myself in the very real sensations of having my pussy eaten out, and the voyeuristic fantasy of his assistant listening to my cries of pleasure, perhaps even with her hand in her own panties, bringing herself off. I closed my eyes as his lips touched my vulva, and I let out an involuntary moan as he kissed it. He was so soft and gentle.

"Do you know what to do, baby?" I whispered. He shook his head, with his lips still kissing the opening of my tight hole, which gave me the most amazing stimulus. "Oh," I cried softly, "do that again." He laughed, then pressed his mouth tight against me and shook his head, thrilling me intensely. "Give me your tongue, baby," I managed to say between a few quick breaths. As he inserted it, I continued to coach him. "That's right, baby. Slide it up and down my slit. Oh yes. Oh, that's good. Now can you feel the stiff bit at the top?"

It turns out he was far more of a gentleman than I had imagined, being far too polite to talk with his mouth full, so I just continued. "That's my clitoris," I told him. "Just flick it with the tip of your tongue. Oh, yes. Oh my God, yes!" I cried, rather louder than I had wanted to. "Now, slide your tongue down to the bottom of my slit. Oh, God. Oh, yes. Oh, that feels so good. Oh, yes. Now push in a bit. Can you feel that little hole at the bottom?"

He nodded, driving me crazy with desire again. "Push in more, now. Oh, yes. Oh my God, yes!" I cried out. It was getting increasingly difficult to think, much less talk, and my breathing kept getting quicker. Fortunately, as it happened, I only needed to communicate one more vital request, "Now for the hard part. Do you think you can suck on my clitty as you push your tongue in my pussy?" He could. I was amazed. I was writhing on my back on his desk, fondling my own breasts and nipples. My involuntary responses increased, and before long, I was pushing my crotch up to meet his thrusting tongue. Tiny as I am, I could just make out the squeaky wheels of his office chair moving to and fro, and he gripped me even tighter around my hips. Badly-oiled wheels were soon drowned out by the sound of the tops of my thighs slapping against his face, and his tongue driving in and out of my sopping wet minge. He was eating me as if he'd been doing it all his life. "That's right, baby! Push it in! Again and again!That's right, baby. Fuck me with your tongue! Make me come on your face!" Well, that's what I *would* have been saying, if my mind wasn't being bombarded with constant messages from almost every pleasure center in my body. What I actually got out, in words, was the last bit, and had things gone to plan, he would have no doubt been rewarded with more of my juices than he could handle as I screamed my way through an intense, full-body orgasm.

Sadly, I had rather lost control of both my body and the situation by this time.

My eyes were closed and I was enjoying myself in a way that I had never done before. No one could ever have imagined this stocky little guy capable of giving so much pleasure. It just goes to show how deceptive appearances can be, in a way. But then the feeling stopped. "Oh no. Don't stop," I desperately moaned, still kneading my breasts and rolling my stiff little nipples around between my fingers. That was when I felt him touch me again. At first I thought it was his tongue, until I felt him enter me. I opened my eyes, but it was too late. Already his cock, stiff again from the excitement, was inside me. I tried to get up but his hands gripped my elbows and he pinned me on my back as he leaned over and began to fuck me.

I suppose I should have expected it; even with all of the positive feedback I was giving him during his efforts, I knew that, ultimately, he was a selfish man. He made my workaday life a continual bore with the driest submissions, while keeping the best for himself; of *course* he would abandon me at the edge of incredible release to get himself off again, in a manner I explicitly forbade. What with me being so slight and him being so chunky, I had no choice at the time but to lay back and take it. I knew there were other ways of escape that didn't rely on overwhelming strength, but, in the back of my mind, I was already considering more, ah, memorable, payback methods. I could be charitable and say that his sucking my bare breasts was out of a genuine desire to push me over the edge, but I'm more inclined to think that he simply didn't care to engage in talk of any kind. He quickly escalated his pace of humping into me, and as my legs kicked out on either side of his fat waist I could tell he was already close.

"Ok," I moaned, reluctantly accepting my fate, "but don't come inside me." That too fell on deaf ears, but at least he was mostly spent from the previous orgasm. As he came inside me he was lying on top, suckling on first one firm breast then the other and the strangest thought occurred to me. "I wonder if they taste different?" I thought. "Or if they even taste at all?" I took these musings as a sign of my utter detachment from the present, and as a hopeful sign that my subconscious was even now working on Alf's retribution. My new assertiveness, I decided, was not going to be countered by this selfish prig's actions.

Another handful of tissues and another sandwich bag, and we were both replacing our attire. We didn't say much more, and as put out as I was by his lack of consideration, I couldn't help but smile as I left with a romantic novel, two thrillers, a murder mystery and an erotic novel. What I had no plans of returning to was "The Secret Life of Mollusks", and not because the act would symbolize the beginning of my "new life" or any such tosh: the thing was just a fucking bore. One thing I did make a point of doing though, as soon as I left his office, was to visit my local pharmacy to procure for myself a dose of "morning after" medication, just in case. I had a little over a week's worth of work, which meant I had the same amount of time to come up with a plan to prevent regular purchases of this kind.

But let's put that aside for now, because I want to talk about the sort of person I find myself really attracted to, which would be a woman. Someone like myself, although I hasten to add I've never been with another woman, I just know that if I did, she would probably be small and petite, like that cute little blonde with the group in the coffee bar.

If I had to analyse myself, I would probably say my aforementioned (slight) fear of men stems solely from what I imagine a big man might do do me, physically I mean. And it's not in any sense of an abusive relationship, either, but purely on the basis of the proportions of our respective naughty bits. Not only do I think a woman partner would be more gentle and more likely to give me the pleasure I need, she would do it without the pain that I dread. I've met a few women that I felt attracted to too, but being shy and not too sure of myself, I've never plucked up the courage to move out of my comfort zone and "take the plunge" so to speak. I have no qualms about getting intimate with another woman either, quite the opposite in fact, but neither have I ever been approached by anyone in that respect and before this particular day I certainly wouldn't have thought I could ever initiate the encounter.

So, having just shagged my boss on his office desk an hour or so earlier, I felt quite elated when I looked up from the new erotic manuscript I was reading and noticed Tracey (for that, I was later to learn, was the name of my little blonde object of desire) smiling discreetly at me, before coyly looking away. Yvonne, the tall woman, caught her gaze and turned to scowl at me as if to say "Keep off. She's mine." It was an unnerving glare and were it not for the fact that I so dearly wanted to get to know the delightful cutie, I might well have kept my distance. But I thought to myself "Well, what is she going to do in a public café if I go and introduce myself?" Little did I realise that I was about to venture into the lion's den, or to put it more aptly, the tiger's domain.

They had sat themselves down at a small table in the opposite corner from mine, just to one side of where I was working. Tracey was facing my table with the brunette and oriental women seated on either side of her. The tall, exotic woman had her back to me and seemed to be entertained by the antics of the other three. I decided to throw caution to the wind for the second time that day and go over to introduce myself.

"Hello," I said, in what I imagined to be a friendly, confident voice, "I'm Janice. I wondered if I might join you?"

"Why?" the tall woman asked curtly, turning her stern face toward me. Whatever amusement the others had provided, there was no trace of a smile now; no kindness in her face at all, really, and I felt I had probably never in my life met anyone quite as thoroughly disagreeable.

I was completely taken aback, my earlier confidence faded, and I was lost for words.

"Sorry," the oriental-looking woman said, more kindly, breaking a few seconds of uneasy silence. "It's a sort of, err..."

"A club!" the buxom brunette added on her friend's behalf.

"What sort of club?" I asked, trying to affect something in the neighborhood of a confident tone.

"It's something like a ... special interest group." the cute little blonde added with a kindly smile, genuinely intrigued by my interest, and two of the others giggled discreetly into their hands.

I must have looked as confused as I felt when I asked, "How do I join?"

"You don't," the tall woman said cuttingly, emphasising the word "you" as if she was saying there was no place among their select little group for me personally. I heard the little blonde woman gasp slightly, which I took to be a sign she was just as affronted by the overly-harsh response as I was. I turned my attention to her, to perhaps share a "Can you believe this bitch?" look, but her expression was definitely not one of disbelief.

I say I've never been with a woman, intimately, but there was no mistaking the signs of arousal on her face. She had a white-knuckle grip on the edge of the table, and her head was tilted slightly downwards; her eyes were closed, but her mouth was half-open, and as I watched, she had several full-body twitches. I have no idea how long the sight of her in that state entranced me. My eyes traveled down her body, past her chest, as her gorgeous breasts heaved up and down with her quickening breathing, and the spell only broke when I noticed the two women flanking her had their hands under the table. As much fun as they were clearly having, they must have decided the show wasn't for me, because as soon as the oriental woman caught my lustful gaze, she brought her hand back into view and nodded at the brunette to do the same.

"Oh," I said, shaking my head as if to clear the vision of Tracey in a deep state of arousal, and to get my mind back on the original track. "The club!" my brain helpfully exclaimed, and reminded me that I couldn't join. That left me feeling deflated once again, and yet, I remained curious at the same time.

"You have to be invited," the little blonde explained as she wriggled in her seat. The "club members" on her sides seemed to take satisfaction in her motions, as though they had done a very good job of whatever their hands had been up to under the table.

"These two women are molesting her," I silently deduced, "but she's clearly not objecting so I shouldn't interfere," my thought continued. Out loud, I asked, "Couldn't you invite me?" failing to disguise the persistent hope in my voice, now that I could sense that she seemed rather more approachable than the others.

She looked to the others for support, then said, "I'm afraid I can't," after a few seconds of awkward silence, looking disappointed, "I'm not..." she paused.

"She's not a full member herself." the oriental woman answered for her.

"Oh," I replied. "When will you be a full member?" I probed further, despite my growing feeling that my joining up was never going to be in the cards. The oriental and the tall woman half-smiled at each other for a brief moment, then both tried to answer together.

"Tonigh..." the oriental began to say, a wry, expectant smile on her face, which fell away as she was immediately interrupted by the tall, exotic woman, who challenged me, asking, "Why so many questions?" Again, she managed to wipe all trace of the softer expression she just shared with her friend mere moments before, which was a shame, really. In that flash of a smile, she looked every bit as young as her companions, and the more exotic aspects of her beauty became much more pronounced.

"I'm sorry," I said, gathering my composure as at last I accepted the fact I was going to get nowhere. "I'm interrupting. Sorry to have disturbed you," I added as I spun on my heel to return to my table and my work. I sat at my table for another twenty minutes taking the greatest of care not to even so much as glance in their direction, although I felt sure they were probably watching me and discussing me. There seemed little point in pursuing the enquiry further so I buried my head in my proofing and tried to forget them. My eyes slid over the erotica on my screen without taking in so much as a single, lusty word. I silently berated myself for letting one awful woman's attitude completely demolish my self-assuredness just as I was beginning to discover it. Alf had me under his thumb for months, using me to do the work he never would, and while I had made some mistakes in my first attempt at controlling my destiny, I managed to rebound, somewhat, and even came away with some spoils of victory. In contrast, I had barely an hour's time in the presence of this callous bitch, and already I was regressing into the shy creature that would have meekly accepted her mollusk-book fate.