Cover of The Sissy Gambit of a Vegas Escort

The Sissy Gambit of a Vegas Escort

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All characters are 18 years old or older. A story told in 2nd person perspective about me, Kief Clark, 46. a construction tradesskills trainer. I'm just shy of 5'11", 190 lbs, with brown (graying at the temples) hair that I keep fairly short because of its thin nature and a vicious widow's peaked receding hairline. My dark as "poop" brown eyes aren't much to write home about, but if you're an old Asian person, they're what gives away my ½ Indonesian heritage. Ive got a semi- permanent 5 o'clock shadow. I can shave smooth in the morning and you could tell by 3pm that I have a beard coming in, same for body hair. The reason I watch so much bbc gangbang sissy hypno porn, is that Ive identified with sissies(submissive transfemme individuals worth limp micropenises of a tiny limp nature, who are so feminine that most men and every black man with a 10 inch or bigger cock would fuck them aggressively, while achieving multiple orgasms even though they technically have a penis) because they have tiny limp penises and orgasm from anal sex. On a Blacked web page, a wealthy black man, with a 12 inch cock in Las Vegas and tons of friends just like him, would like to have him come live in Vegas and be transformed into a sissy bimbo, 12 inch BBC gangbang addicted high end sissy escort, Lexi Feelexy, and that he will pay the upfront cost of new G Cups, facial reconstruction to look like Alexa Bliss and lipo, also he can deage you to 19. but creating an OF about his will pay for most everything, I just had to agree and do whatever he says. I say yes to everything

Chapter 1: The Arrival

The elevator didn’t have buttons. It just ascended, a silent golden cube, and when the doors slid open Kief felt the air change. It was cooler, drier, and carried a scent—clean, sharp cologne over something deeper, like well-oiled leather and polished stone. The foyer was all black marble and dark glass, reflecting the dizzying kaleidoscope of the Strip fifty floors below.

His duffel bag, stained with old coffee and concrete dust, felt like a sack of garbage in his hand.

“Right on time.”

The voice came from the living room, a low rumble that seemed to vibrate in Kief’s ribs. Dante stood silhouetted against the floor-to-ceiling windows, a skyline of neon fire framing his broad shoulders. He turned, and the city’s light glinted off the platinum of his watch. He wasn’t smiling, not exactly. His expression was one of pure appraisal.

“You made it,” Dante said, walking forward. He wore a charcoal suit that looked softer than anything Kief had ever touched. “Long flight?”

“It was… fine.” Kief’s own voice sounded reedy, pathetic. He cleared his throat.

Dante’s eyes, dark and impossible to read, traveled down Kief’s body—over the faded denim jacket, the Walmart jeans, the scuffed work boots—and back up. That look stripped him bare more effectively than any hands could. Kief felt his cock, half-hard since he’d boarded the private jet, give a painful throb against his zipper.

“This way.”

Kief followed, his boots too loud on the marble. The living room was cavernous. A dozen men lounged on low sofas, glasses of amber liquid in hand. They were all kinds of polished—sharp suits, perfect beards, watches that probably cost more than a house. They all stopped talking and looked. Not at his face. At his body, with a cold, clinical interest that made his skin prickle. One, a massive guy with shoulders that strained his jacket, smirked and took a slow sip of his drink.

“Sit,” Dante said, gesturing to a single leather chair in the center of the room. It faced a low glass table. On the table was a thick document and a pen.

Kief sat, placing his duffel between his feet like a shield. The leather was cool, suppressive.

Dante settled on the edge of the table, right in front of him, blocking the view of the other men. He picked up the contract. “We’ve discussed the broad strokes. The surgeries. The de-aging compounds. The financial arrangement. The… lifestyle.” He let the pages fan slightly. “This makes it real. It gives me legal and physical custody of you for the next five years. You will be Lexi Feelexy. Every debt, every medical procedure, every client I schedule for you is in here. Sign it, and there is no going back to being Kief Clark. He ceases to exist.”

Kief’s mouth was desert-dry. He’d dreamed of this, jerked off to the idea of it a thousand times in his lonely trailer. But here, under these eyes, the fantasy had sharp, cutting edges. “I understand.”

“Do you?” Dante leaned forward slightly. The scent of his cologne intensified. “This isn’t porn. It’s not a video you can close. Once we start, we finish. You will wake up with G-cup tits and the face of a blonde bombshell. You will have the body of a nineteen-year-old bait bitch. And you will use that body to service men. Big men. Men who will use your holes for their pleasure, not yours. Though,” he added, a flicker of something cruel in his eyes, “we both know you’ll get plenty of pleasure from it, don’t we, sissy?”

The word, said in that smooth, commanding tone, shot straight to Kief’s groin. A damp spot bloomed on the front of his jeans. He nodded, unable to speak.

“Good.” Dante placed the contract back on the table. He didn’t offer the pen. Instead, he leaned back, his gaze turning imperious. “Lesson one. Obedience isn’t signed. It’s performed. Strip.”

A cold shock, then a rush of heat. Kief’s eyes flickered to the other men. They were all watching, silent.

“Everything,” Dante said, his voice leaving no room for question. “Let these gentlemen see what I’m investing in. Let them see the clay I have to work with.”

Kief’s fingers trembled as he fumbled with the buttons of his denim jacket. He shrugged it off, letting it fall to the floor with a thud of his wallet and keys. His t-shirt came next, sticking to his damp chest. The air conditioning kissed his skin, pebbling his nipples, tightening the dark thatch of hair across his pectorals. He avoided looking at anyone, focusing on his boots. The laces were knotted. He bent, his back to the room, and struggled.

“Take your time,” Dante murmured, and someone chuckled.

Finally, the boots were off, the socks. He stood in just his jeans. His hard-on was a obvious, shameful tent in the worn fabric.

“The rest,” Dante commanded.

Kief unbuttoned his jeans, pushed them and his briefs down in one clumsy motion, and stepped out of the puddled fabric. He was naked. Exposed. His cock, a pathetic four inches on his best day, stood rigid, curving upwards against his hairy belly. A drop of pre-cum glistened at the slit. He was covered in body hair, a rolling landscape of it, from his shoulders down to his thick thighs. He wanted to cover himself, but he forced his hands to stay at his sides, fists clenched.

Dante looked him over with the detached focus of a sculptor surveying a block of marble. “Turn around. Bend over. Spread your cheeks. Show them your asset.”

Humiliation burned through him, molten and sweet. He turned, facing the window and the indifferent city. He bent from the waist, reaching back with shaking hands to pull the fleshy mounds of his ass apart, exposing his pink, tight hole to the cool air and the hot stares behind him.

A low whistle cut the silence.

“Hairy as a fucking gorilla,” a voice said.

“Needs a lot of work,” another agreed.

“But the structure’s there,” Dante said, his voice closer now. Kief jumped as a finger, cold and firm, traced the furrow between his cheeks, not touching his hole, just outlining it. “The hips are wide. The spine is flexible. The hole is virgin, for all intents and purposes. It’s perfect.”

The finger withdrew. “You can stand up.”

Kief straightened, his face flaming. He didn’t turn around.

“Come here,” Dante said. Kief turned. Dante was sitting in the leather chair now, his own pants open, his monstrous cock freed. It was thick, long, and dark, lying against his thigh like a weapon. Fully soft, it was bigger than Kief had ever been hard. Kief’s own dick leaked, a thin string of sissy precum dripping onto the dark marble floor.

“Lesson two,” Dante said, his hand stroking his own length slowly, making it thicken and rise. “A sissy’s mouth is her first cunt. It’s where she learns to swallow, to choke, to worship. Come and learn.”

Kief moved on wooden legs. He sank to his knees on the hard floor, the cool stone biting into his skin. The scent of Dante—musky, powerful, dominant—filled his head. Up close, the cock was intimidating, a veined pillar of black flesh. The sheer size of it made his own little prick shrivel in submission, dripping uselessly.

“Open wide.”

Kief parted his lips. Dante didn’t guide himself in. He just watched as Kief leaned forward, his own movements hesitant. The broad, spongy head bumped against his teeth. He opened wider, straining his jaw, and took the crown into his mouth. It was warm, salty. He couldn’t get half of it. He gagged, eyes watering.

“Relax your throat,” Dante instructed, his voice calm. He placed a large hand on the back of Kief’s head. “You’re going to take it all. This is what you wanted. This is what you signed up for. Now, take it.”

The pressure on his head was firm, inexorable. Kief tried to breathe through his nose as Dante pushed forward. The thick shaft stretched his lips, filled his mouth, then hit the back of his throat. He gagged violently, spit running down his chin. Dante held him there, not letting him retreat.

“Swallow,” Dante commanded.

Kief tried. The convulsive motion of his throat seemed to please Dante, who began a slow, deep rhythm, fucking his face with a relentless, patient pressure. Each thrust pushed a little deeper, until Kief’s nose was buried in the coarse, dark hair at the base, the entire, terrifying length buried down his throat. His eyes streamed tears. His own tiny cock was a throbbing, ignored ache, drooling a puddle beneath him. He couldn’t breathe, could only exist as a vessel, a warm, wet hole for this god-like man to use.

After an eternity, Dante pulled him off by the hair. Kief gasped, dragging in ragged, wet breaths, strings of saliva and pre-cum connecting his bruised lips to Dante’s glistening cock.

“Not terrible,” Dante said, almost to himself. He looked past Kief to the other men. “Who’s next? He needs to learn his place is on his knees or on his back.”

The massive man from the sofa stood up, already unbuckling his belt. Kief watched, dizzy, as another massive black cock, just as thick, swung free. Dante guided Kief’s head towards it.

“Lesson three,” Dante whispered in his ear, as the new cockhead pressed against his slippery lips. “A sissy doesn’t need to breathe. She just needs to serve.”

As Kief opened his mouth again, as a second thick girth began to stretch him, a profound, terrifying certainty settled in his gut. Kief Clark was gone. He was just a hole now, a collection of entries and exits soon to be remade. And as the second cock began to pump ruthlessly into his throat, he felt the first real, shuddering sissy-gasm building in his worthless, tiny balls—a pathetic, dripping release that had nothing to do with his dick and everything to do with the utter, complete annihilation of the man he used to be.

And as the second cock began to pump ruthlessly into his throat, he felt the first real, shuddering sissy-gasm building in his worthless, tiny balls—a pathetic, dripping release that had nothing to do with his dick and everything to do with the utter, complete annihilation of the man he used to be.

It was a whisper of pleasure, a shallow pulsing in his groin that left a warm, sticky puddle on the marble beneath his knees. No one noticed. No one cared.

The gangbang that followed was a blur of heat, pressure, and brutal rhythm. He lost count. A cock was in his mouth, grinding against his tonsils. Then he was bent over the glass table, his cheek pressed to cold, smeared glass, as a thickness far greater than anything he’d ever imagined split his asspussy open with a single, burning thrust. He screamed, a muffled, wet sound, but the scream melted into a broken sob of euphoria as the pain blossomed into a pleasure so intense it short-circuited his thoughts. His mind went white. His little prick dribbled continuously, a useless fountain synced to each pound of a stranger’s hips against his hairy ass.

Hands were everywhere. Guiding his head onto another shaft. Spreading his cheeks wider. Slapping his flesh, marking him. He was a living, breathing toy. He came again, silently, just a shudder and more fluid leaking from his tiny slit, as a third man emptied a hot, viscous load deep inside his colon.

When they were done, he lay on the floor, a broken mess of sweat, semen, and his own sissy juice. He trembled, every muscle loose and buzzing. The men talked above him, their voices casual, as if discussing a sports play.

“Needs a lot of grooming.”

“The surgeries will fix the frame. De-aging chemo’ll smooth the skin.”

“Gonna be a primo little fuck-doll.”

Dante’s polished shoes appeared in his blurry vision. “Get up.”

Kief tried. His legs were jelly. A strong hand—not Dante’s—hooked under his arm and hauled him upright. He swayed, covered in filth.

“Hold him steady.”

Two men gripped his arms. Dante knelt before him, holding two objects. The first was a pair of shoes. Clear, six-inch platform stilettos, the heels needles, the platforms thick as bricks. Without ceremony, Dante lifted one of Kief’s filthy feet and forced it into the hard plastic. The fit was tight, unforgiving. He did the other. The change in balance was immediate and terrifying. Kief pitched forward, held up only by the men. His weight bore down on the balls of his feet, his arches screaming. He was towering, unstable, and utterly feminized.

“Now, the crown jewel,” Dante said, his voice a satisfied purr.

The second object was a chastity device. It was flat and clear, a minimalist cage of hard plastic. From its front protruded a short, pink urethral tube that ended in a sculpted, open pink mouth, like a doll’s lips frozen in a perfect ‘O’. Dante took Kief’s limp, wet, half-inch penis between his fingers, gave it a dismissive tug, and guided the pink tube into the slit.

A sharp, invasive pressure, then a pop as the head of his urethra was breached. Kief whimpered. Dante secured the base ring behind his balls and snapped the cage shut with a final click. The effect was instantaneous. His pathetic cock was gone, rendered a flat, seamless bulge. And from the open pink mouth at the end of the tube, a steady, clear drip of his precum began to fall. Drip. Drip. Drip. onto the marble.

“These are your fundamentals,” Dante said, standing back to admire his work. “You wear these always. Unless I tell you to clean them, or you’re getting dressed, or putting on a different color or a taller pair. This drip?” He pointed to the falling fluid. “This is your truth now. It never stops.”

Dante walked to a sideboard and returned with a small tray. On it sat a glass meth pipe, a small bottle of clear liquid with a dropper—GHB—and a small brown bottle of poppers. He placed the tray in Kief’s trembling hands.

“You should always be high on meth and GHB. I know you flip them religiously already. They make you rant about BBC gangbangs. That’s good. The poppers,” he tapped the brown bottle, “you breathe in continuously whilst watching hypno porn. It opens your mind. And your ass.”

Dante pointed down a hallway. “Last door is your room. It’s decked out. Multiple TVs playing the good stuff 24/7. It also streams directly to my rig. I’ll be watching. Always. There’s dildos, lube, all the drugs you could want, and water. Nothing else. No clothes that aren’t mine. No books. No phone.”

He leaned in close, his breath hot on Kief’s ear. “Your only job for the next thirty-six hours is to go sit and hypno out. Get fucking obliterated. Let the programming sink past your bones. I want you so deep in the sissy zone you forget your own name. I want Kief Clark to dissolve in a puddle of chem and cum.”

He gave Kief a slight push. “Go.”

The walk down the hallway was a surreal, clattering nightmare. The clear heels click-clacked hysterically on the marble, each step a precarious battle against gravity. The pink mouth at his groin wept its steady confession. He fumbled with the tray, his hands shaking.

He reached the last door. Opened it.

The wall was a constellation of screens. Each one played a different, seamlessly edited hypno video. Glorious, muscled black men moved in slow motion. Sissies, prettier than any real woman, screamed in ecstasy, their caged clits dripping. Phrases flashed: EMPTY YOUR MIND. FILL YOUR ASS. OBEY. BLACK COCK IS OWNERSHIP. The audio was a layered chaos of throbbing bass, moans, and subliminal whispers.

In the center of the room was a plush, pink upholstered chaise. Around it, on stands, were dildos of varying, impossible sizes. Jugs of lube. A mini-fridge. A case of water bottles.

Kief stumbled to the chaise, placed the tray beside him. His hands moved on autopilot, the ritual older than his desire to come here. He heated the pipe, sucked the sharp, chemical smoke deep into his lungs. The world snapped into hyper-clarity, every pixel on the screens vibrating. Then the GHB, a dropperful under his tongue, a sweet, chemical wash that melted the meth-edge into a warm, pliable surrender.

He grabbed the poppers, unscrewed the cap. He brought it to one nostril, pressed the other shut, and inhaled a deep, punishing lungful of the sickly-sweet amyl fumes. His head rushed. His vision tunneled. The screens seemed to bulge outward, consuming him.

CLICK-CLACK-CLICK from the hallway. The door didn’t close. Dante stood there, leaning against the frame, watching him.

Kief didn’t look away from the screens. He took another hit of poppers. The chanting from the videos became his own internal monologue. He slumped back into the chaise, legs falling open, the clear heels splayed, the pink mouth dripping onto the pink fabric.

He was gone. Lexi was here. And from a camera in the ceiling, a small red light glowed, feeding every twitch, every drip, every blank, blissed-out expression directly to Dante’s monitor. The transformation had moved beyond the physical. It was now a live broadcast of a soul being systematically rewritten.

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