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All In - Chapter One

by kneelingsissy

All In - Chapter One

"Raise. Fifty-five." Master threw a sliding stack of chips across the line, where they spilled into an artful red splash against the felt. He did not look at me, nor I at him. I thought I saw Jeanette glance in my direction, but I resisted the urge to return the look, so I wasn't certain. It was probably nothing more than my knowledge of her knowledge: not a guilty conscience, because any guilt I felt about such games had long since melted away, but perhaps a vigilant one – a person involved in the type of relationship Master, Jeanette and I have does well to remain on alert for the awareness of others. That awareness can be a crucial part of the play – onlookers in a club while I'm on the rack or bent over a bench, drunk couples passing by the mouth of the alley against whose wall I am pressed cheek- and palms-first, with my skirt stretched taut between spread ankles and a ball of wet, shredded cotton that used to be my panties gathering drool between my teeth – but that awareness can also be a dire threat, as in police detainment when the fun stops bending the public indecency laws and starts breaking them.

With Master, the fun always starts breaking them.

"Going for a beer," I said. "Anyone need anything while I'm up?"

Nobody did, save Jeanette, who asked me with a sly sparkle in her eyes to refresh her margarita. I took her sweating glass and my empty longneck and went through the living room to the kitchen, hips swinging just the right amount, which is to say enough for a careful, appraising eye to notice but not quite enough – hopefully – to attract the attention of men three beers deep in their Hold 'Em hands.

To be clear, I'm not gay, although I didn't find the label particularly derogatory even before I started satisfying Master's member in an astounding variety of ways. I am also not gay despite the several articles of custom-ordered women's underwear which have for some months resided in my top dresser drawer, articles which bear various creative terms such as "cockgulping faggot" and "I love my boyfriend." Then there's the "temporary" tattoo template that cost Master more than $200, the one which has frilly script reading "Faggot Fucktoy" wrapped over a glossy red heart; it's not the only such template he keeps on hand for me, but it's one of his favorites. Ironically, Master is one of the most tolerant people I know; the F-word just seems to really crank his engine, though only when applied to yours truly.

In the kitchen, I stood still for a moment. Hearing nothing but the sounds of the game coming from two rooms away, I set down the bottle and the glass and snuck back into the living room and thence to the side hallway, being careful to keep out of sight of the den, which gave onto the living room and from which the players could see me if I wasn't careful.

In the half-bath, I closed the door slowly behind me and locked it before dropping my pants and underwear and sitting on the john. As I "made water," I examined the panties around my thighs for signs of wetness. I saw some, which was unavoidable, but they were nearly dry. They were a bright red "cheeky" pair from VS, both Master's and my favorite color, and a good color to betray the water that leaked from my ass when I didn't hold myself clenched tightly to prevent it.

That water, which I now expelled, was the remains of a substantial ice dildo that I had inserted about forty minutes ago. Every once in awhile, at long enough intervals to prevent health risks from the significant amount of ice in a very sensitive area but frequently enough to keep me from getting comfortable, Master raised the pot by $55, and this was my signal to find an excuse to sneak into the kitchen and insert a fresh dildo from the supply he kept in the freezer. The dildos, like the tattoo templates and so many of the other gloriously sleazy toys and accessories purchased for my edification, had cost a pretty penny; they were made from plastic freezer molds, the kind kids use to turn Kool-Aid into popsicles, which were in turn made from a plaster mold of Master's erect cock.

So I pulled up my panties, snapped my skin-tight jeans, and returned to the kitchen, where I found a neat row of Master's cocks waiting for me, hidden rather casually beneath a gallon bag of chicken tenders. Again I dropped trousers, waiting every moment for one of Master's poker friends to walk into the kitchen for a beer or bowl of pretzels only to find me bent over the counter, waxed ass bared, with red panties bunched around the lower curve of my buttocks and a steaming ice-cock poised between my cheeks.

My phone buzzed. I jumped, nearly dropped the dildo, and caught myself with my other hand against the side of the fridge. The phone was on silent but its vibrate was very strong, and the thin fabric of my skinny jeans kept it pressed hard against my thigh. It might seem like a buzzing iPhone would feel the same against a man's hairy leg as it would against a sissy's shaved one, but the difference is noticeable, and my ringing or shaking phone was always a tiny reminder of my status: shaved legs, waxed loins, collar beneath my turtleneck, the little clutch of loud eyeshadow and hot pink lip gloss and ruby blush that hid in my glove box. A sissy's distinctions.

I stood in the kitchen, feeling the phone and the drip of ice water as it ran down the edge of my hand, waiting like an American Pie character for someone to stumble upon me in my moment of absolute abjection. I thought, This is ridiculous, and pushed the dildo into place.

I began the move by flexing my heels outward and pressing my ass into the icy head, but as always, when I felt the first penetration, the kiss of frost against my long-suffering nether door, I blanched a little. I'd learned long ago that such a reaction not only displeased Master, Jeanette, or whichever Dom happened to be requesting admittance, but also resulted in a more painful experience; anyone who has had something the size of a seven- or eight-inch phallus put into their rectum will recognize the sentiment. Thus, when I felt myself instinctively puckering against the dripping head of my Master's simulacrum, I exhaled through pursed lips, let loose every muscle from my abdomen to my thighs, and shoved. This is not a maneuver I recommend to the uninitiated, as an improper execution can be quite the learning experience, but my ass hasn't had the privilege of being uninitiated for about eight years, and the six months I'd known Master had put it through more trials than an inner-city circuit court, so the phallus slid home quite neatly.

It was a piercing shock of violating pain. It was a barb of pleasure, unbearable because of the cold and because though its shape reminded my flesh of Master's sex, it brought none of the throbbing heat or life to my body that the genuine article always did.

I wiggled a bit, holding my index finger in place as I made sure the toy was seated properly, and then pulled up my panties and jeans, working my sphincter into a clenched gate. I licked my finger dry, which is less repugnant than it sounds since, like most highly-active anal sub missives, I'm kept scrupulously clean, especially on evenings when Master has special play scheduled, such as tonight. I washed my hands, refilled Jeanette's drink, plucked a fresh Miller 64 from the door of the fridge, and then remembered my phone. I set down the bottle and tugged it from my pocket.
Master – New Text Message, it read.

I clicked through the menus and saw: earrings.

A spike of ice that had nothing to do with the frozen shaft pinning me from behind rose up through my stomach. I left the beer on the counter and made my way back into the side hall, where I opened Master's bedroom door and found a pair of my earrings waiting for me on Jeanette's vanity. They were discrete – tiny silver studs, no more than little molten balls of glossy metal – but they shone like polished glass even in the low light of the recessed track-lighting that fell upon the room from the far corner, near the master bath. They would glint gloriously in the glare of the green-shaded fluorescent hung above the poker felt back in the den.

Time was wasting, big blinds were passing, and cocks were melting. I ducked in front of the mirror, appreciating even in my haste my flawless shave and glossy bob-cut hair, which fell in a dark, sultry sheet across both cheekbones and covered all but the lowermost third of my ears, where the silver studs would o. I popped them in, retrieved Jeanette's margarita, and headed for the den, stopping only to gather my girly, 64-calorie beer from the kitchen counter.

"Where was that beer," Jeanette said as I sat down, "Dallas?"

"Missed the blinds," Master said, not even looking up. "Pony up."


I remember my first day on the job that Master got me. It was at his firm, which was respectably average as tax-accounting law firms in the southwest went and generally required a moderately-impressive resume and a couple years of paralegal or administrative experience from even the lowliest applicant. Unsurprisingly, taking it up the ass from one of the titular partners proved an adequate substitute for the standard qualifications.

I had been at my desk for about two hours, navigating as best I could the stacks of copied forms, triplicate invoices, and mismatched files, when I met Dani. I don't know how long she watched me suffer beneath the mountain of unfamiliar paperwork, which I had thought I was managing passably well due to my eight months of hard-core time as an intern at a mom-and-pop patent firm back in Waco, but I remember being so surprised when she finally spoke that I was sure the medium plug Master had asked me to wear was going to pop right out of me and fill my boy-short panties with four inches of conical rubber and a quarter ounce of water-based lubricant.

"God," she said, "who did you sleep with to get here?"

I spun in my ergonomic chair and saw a girl who couldn't be a day north of seventeen leaning into my peasant's cubicle. She had dark hair and dark jeans and eyes like a laughing sea. I remember admiring the cut of her blouse and the way her chic faux-suede jacket went with her jeans, because it was the jeans, a dark stone-wash affair which appeared to have been vacuum-sealed to her hips and legs, that gave me my rebuttal.

"None of your P or Q," I said. "Who did you sleep with to get away with wearing jeans to work here?"

Her eyebrows reached for the sky. "Who said I work here?" she said. "What if I'm the favored mistress of one of the managing partners, and I hang around for the sole purpose of getting new and incompetent paralegals fired for making snide remarks about my wardrobe?"

Warming to the repartee, I opened my mouth, but then considered the possibility that she was telling some variety of truth. After all, I was basically what she had just claimed to be, though "favored mistress" was a far cry from what I was to Master Alex.

"Relax," she said, having taken my hesitation for trepidation. "I'm fucking with you. I'm Dani."
"Sam," I said. We shook.

"So, seriously," she said, eyeing with mild alarm the mountain range rising around me, "are you in over your head here?"

Some ninety minutes later, with the Alps reduced to Appalachians and some distant semblance of order emerging from the jetsam, we sat hip to hip on a capsized two-drawer filing cabinet, having jettisoned the ergonomic swayback as a space-hog. We had briefly considered having her sit on my lap, she joking and I not, and she had countered this proposal by suggesting that I display a more tolerant attitude toward gender relations by sitting on her lap. I had made it most of the way there when she'd squealed with alarm and goosed me through my fitted slacks. We'd looked at one another, each half-offended and each guilty of blurring a line, and a long moment had passed, during which we might have stiffly parted ways and never really spoken closely again. Instead, something solidified between us in that silence, and we laughed, not without anxiety, and had kicked the chair out into the little carpeted aisle and cannibalized the empty cabinet as our loveseat.

It was then that Master Alex, known to the serfs as Senior Partner Alex McRae, came down the central aisle in the cubicle farm. Neither of us registered his presence until he clapped a hand on either of our shoulders.

"Neck deep already, eh?" he said. "Dani, glad to see you're helping the new help. Mandelson doesn't need you this morning?"

"I came in early to refile his accounts pending, sir," she said. "And we were able to knock out the deposition transcripts for the Connolly account two hours ago."

"That's my girl. Partner by November at this rate."

She smiled dutifully at this, and Master pulled back. I felt his hand brush my earlobe as it withdrew, and his fingers found the sensitive place behind my lower piercing – empty and nearly invisible while I was at the office – and gave the briefest of squeezes.

"Keep hitting it hard," he said, and then, as though it had just occurred to him, "Oh, ah, Sam. Come find me when you're through for the day this afternoon. I want you and Debbie to go over that new secondary alphabetization you mentioned in your interview. The one you said you helped institute at Stanford?"

"Oh, uh, I did, sir. Yes sir. I will, sir."

"Great! See you then."

After he was gone, I reached for the leaning stack of files we had been processing. My ear tingled and hummed. My pants felt tight in front, and it seemed every line of the cute little sailor-striped panties and every curve of the plug had somehow come alive in the last twenty seconds. I shuffled the file, opened it, and realized that Dani was staring at me. I shot her a look.

"Stanford my lily-white ass," she said. "That's who you're sleeping with. Senior Partner Alexander Moneybags McRae."


"And he invited you up to his office to-" here she put up big floppy air-quotes- "correspond with Debbie? Is that his imaginary assistant who he invokes when he wants to call a little boy-sugar to his private suite on the top floor without drawing undue attention?"


She looked at me, half stupefied and half grinning.

"I'm not gay," I said, sure that my tone or my ear, which felt like it was the shade of the stripe on a barber pole, was giving me away. The irony was that, as I said earlier, I'm not actually gay. I've never had what I would call a relationship with any man other than Master, and I'm not sure what we have qualifies as the kind of thing that gay men dream about when they get out of the shower or watch the latest romantic comedy.

"Don't worry," she said at length. "Your secret is safe with me, boy candy."

I was becoming angry – who did she think she was? – but I breathed in and waited for it to pass. I reached for another folder and thought again that perhaps she was this impertinent and tactless because she was what she said she was: candy, a piece of ass on retainer, cute little bejeaned ass plugged and panties leaking in anticipation of the next time her beau, whoever he might be, buzzed her cell and summoned her upstairs for an evening romp. All fours and a leather horse-bit on the high-pile burgundy carpet. Playing footstool with a vibrator at each end and Sir tapping ash into a tray perched precariously upon the arched curve of her ass.

We went back to work, but the silence between us had cooled.

"Hey," she said, after some minutes.

I looked at her.

"I don't care," she said. She put a hand on my arm. "I'm a nosy bitch and I have a big mouth around my friends, but I meant it, about keeping mum. And I don't care. Maybe it's nothing, anyway. Did you really go to Stanford?"
I had really gone to Stanford, and Master hadn't made up the bit about the filing system I'd helped pioneer there. Nor was Debbie imaginary; she was a frumpy fortysomething who had been his administrative assistant for at least the last thousand years, and though she must have known about his odd predilections, I never knew her to tip so much as half a wink about any of it.
I reported to Master Alex's office that afternoon at 4:41. We did not do any filing.
I tossed twenty-five dollars into the pot – both missed blinds plus ten for my shitty middle pair: eights, worth playing especially from just behind the blinds but not really worth a trap raise before the flop, and sure to melt once we saw the board. The fresh dildo spoke to my prostate and my bowels and the bottom of my spine in pulsating waves of cold so intense it was like a backache and a stomachache combined. I kept myself shut against the urge to let some of the runoff leak out into the bed of my panties. I told myself that the pain would pass as the toy melted, which was true, and that I wasn't about to leap through the roof in a fit of sexual frustration and maddened arousal, which was not; I felt like a cat in heat, claws and raised ass and frenzied yowling that sounded like I was both getting the fuck of my life and being torn apart while still alive. This feeling was fitting, since with Master Alex, both descriptions were likely to be accurate.

He wasn't huge – the ice dildos were his size exactly, down to the perfect head framed by its circumcised hood and its net of positively-lickable veins, and both the toys and the original were no longer than about 7.5, with above average girth but none of the monster thickness that one sees in BBC porn or on novelty shelves in adult shops. He was big; Master's cock hurt me the first time I felt it, and it hurts me still, every time, though every time including the first, the pain brought a dark, blossoming pleasure in its wake, like the nocturnal flower at the end of a thorny stem. But he wasn't enormous, and the tearing apart I mention came much more from his methods than from his measure alone.

Master was, well, a master with his cock. He could strike a rhythm as slow as Chinese water torture or as fervent and full of stroke as a steam engine, and he could hold that rhythm for stretches of time that make me weak in the knees and in the small hollows of my belly when I think about them. Those times were almost never longer than half an hour or perhaps forty-five minutes, but let's be honest; that "fuck me for hours" talk we hear in porn stories and tall tales very rarely holds up to scrutiny, and I'm not saying that Alex McRae started fucking me and came half an hour later. I'm saying that he put me into a position, sometimes freestanding and sometimes restrained, and put his dick into me at a certain speed and intensity, and held that precise rhythm, if he so desired, for as long as three-quarters of an hour on a fairly regular basis. Try that, the next time you're pelvic-bone-deep in a girl or guy, and let me know how long you make it before your triceps give out or your back throws in the towel or your hamstrings lock up. These positions were not missionary; in fact, I'm fairly certain that some of them, homosexuality aside, are illegal on two or three continents.

So when I say that he tore me apart, I mean that he could work my behind like a speed bag for hours, changing positions and speeds if he saw fit, hammering me not only with his cock but also working in flurries of blows with his open hands or floggers or crop or belt or paddle. He liked to saw at my prostate, but only when he had my cock, average in size but prissy in its omnipresent panties and girly accoutrements next to his perennially-tumescent rod, firmly restrained, either in an expensive clear plastic cage, linen rope, or clothespins. He knew that the prostate work drove me wild, and he went to great lengths to totally prevent me from gleaning any substantial penile stimulation from it. He also tore me apart with CBT and various other forms of wickedness while he worked my ass; the times when Master entered me and relied solely on intercourse for his pleasure were not rare, but they certainly felt fewer than those evenings when he did all he could to overload my tied, flogged, reamed body with layer upon layer of punishment and humiliation.

My eights held out; they caught a companion on the flop, giving me a set, the nuts (ironically), and making the freezing throb between my cheeks feel a little further away. I mulled for a moment, knowing that my high hand would likely pan out but also feeling the superior skill and experience of the older men around the table bearing down on me like hot lights; I might take the pot, but if I didn't misrepresent my monster hand, they would smell a trap and walk away, leaving very little pot for me to take.

"Raise. Fifty-five," I said, deciding that the best way to hide my huge hand was to act ilke I had a huge hand. I didn't know if it would fly, but the worst thing that could happen, shy of some devious and highly-unlikely bad luck on the turn or river, was that the four others would fold out and give me the sixty or so dollars in the pot.

Master raised his eyebrows at me. I squirmed a bit beneath his gaze, as always. I thought about the cock in his pants, a curled beast waiting to strike at my soft targets, a bone waiting to take the shape of the shaft of ice pumping its shrill pulse through my loins. My own bone, unburdened as yet by any of Master's chastity cages, began to throb and twitch in my panties.

The two men between Master and I, both middle partners in the firm, folded.

"Raise," Master said. "One-ten."

The other two, faced with no paint on the board and a massive price tag for whatever paltry help fourth and fifth street might bring, bowed out.

"Call," I said, moving before I could think my way out of it. I knew it was the right call, mathematically speaking, but as I shoved in my chips, the throb of the ice dildo intensified, and I felt a tiny line of cold water leak into my panties like sweat.

The dealer burned a bicycle and laid the turn. I watched it come, thinking that, when your opponent is going to end the evening by handcuffing you to a headboard and sodomizing you on live webcam, there's really no good way to finish a three-hundred dollar poker hand.


excellent - kinkysub44

Great writing. A unique perspective in a crowded field of sissy porn. Hot and fantastical, yet totally believable.

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