Cover of The Inevitable Slipping

The Inevitable Slipping

Read the story

2 chapters · 2184 words · Read 0 times

Written in 2nd person, You are Keith a 46 year old teacher, who at nearly 6 ft and 200lbs of hairy dudeness, dont strike anyone as a feminine. One day while out with some coworkers, you all got to talking about your favorite porn actresses and you said the name of a bimbo sissy who specializes in BBC gangbang porn and your reasoning was that as a hyperfeminine trans actress with a limp micropenis and not a pussy, that squirt from anal sex, she's the only one you could identify with. As an 18 year old big tittied pink haired bimbo that only thought about taking BBC 24/7 and always in hot platform stiletto stripper heels, you wish you made those choices at 18, sounds like a fun time. Now someone is slowly forcing you to become their Sissy bimbo. A little more every day, and you dont seem to notice or if you do, you aren't stopping youre inevitable run towards being a bbc addicted sissy bimbo pornslut.

Chapter 1: The Confession at the Bar

h

The whiskey in Keith’s glass caught the sickly yellow light, turning it the color of old urine. The fluorescent tubes above buzzed like a nest of hornets trapped in the ceiling, a sound that vibrated in his molars. Stale beer and fried regret hung in the air, soaked into the sticky vinyl of the booth.

“You’re telling me you don’t have a type? Everyone has a type.” Derrick from the history department was drunk, his voice too loud.

Keith shifted, the leather of the seat squeaking under his two hundred pounds. He felt oversized here, his hairy forearms resting on the table like belonged to someone else. “I don’t know. Just… normal stuff.”

“Bullshit.” Marcus’s voice was a smooth, dark ribbon cutting through Derrick’s slur. He sat across from Keith, a silhouette of relaxed muscle in a tight polo. The new athletic coach. Twenty-nine. He moved through the high school’s halls with a predator’s grace, and now he was smiling, his teeth very white in the dim light. “Everyone has a secret. A little kink they’d never admit to at a staff meeting.”

Keith took a swallow of whiskey. It burned, but the heat was familiar, a welcome distraction from the prickle at the back of his neck. The neon LAST CALL sign flickered, its erratic pulse making the shadows in the corner of the booth seem to breathe.

“Come on, Keith,” Marcus coaxed, leaning forward. His cologne was something expensive and woody, overpowering the stale bar smell. “It’s safe here. We’re all friends. What really gets the old engine turning?”

A nervous laugh escaped Keith’s throat, rough and unused. He looked at the others—Derrick grinning, Paula from the office looking bored and checking her phone. His heart was a thick, heavy drum in his chest. The buzz of the lights seemed to get louder, drowning out the jukebox in the corner. There was a pressure behind his eyes, a weird, loose feeling in his tongue. The whiskey, maybe. His third. Or fourth.

“I, uh…” The word came out before he could catch it. “Alyxxa Kaye.”

Silence, except for the hornet-buzz. Paula looked up, one eyebrow arched. Derrick blinked.

“Who’s that?” Derrick asked. “Some MILF on Pornhub?”

Keith couldn’t look at them. He stared into his glass, his voice dropping to a murmur only their booth could hear. “She’s… a trans performer. Sissy stuff. Hyper-feminine. Bimbo.” Each word was a stone dropped into a still pond, rippling through him. He’d never said them out loud. The fantasy lived in a locked room in his mind, a pink, shameful place he only visited in the dark. “She’s got this… this limp little micro penis. And she… she squirts. Just from anal. They call it a sissygasm.”

The admission hung in the air, toxic and shimmering. He felt stripped naked, his flannel shirt and denim jeans suddenly feeling like a unconvincing costume. He risked a glance at Marcus.

Marcus wasn’t laughing. He wasn’t disgusted. He was studying Keith with an unsettling, focused intensity, like a biologist observing a rare specimen. His smile had widened, but it wasn’t friendly. It was knowing. Predatory. It reached his eyes, which glinted with captured light.

“Fascinating,” Marcus said, the word slow and deliberate. “The complete surrender of it. The transformation. So you identify with her? With that… limp acceptance?”

Keith’s face flushed hot. He gave a jerky, almost imperceptible nod. He felt dizzy. The room tilted.

“If you were in her world,” Marcus continued, his voice a low, hypnotic drone that somehow cut through the buzz, “what would your name be? Every good sissy slut needs a proper bimbo name.”

It was a ridiculous question. A joke. Keith should have laughed it off, ordered another drink, changed the subject. But the locked room in his mind was blown wide open, and the pink, shameful light was flooding out. The name floated up from the depths, from a hundred secret fantasies, fully formed.

“Livvy,” Keith whispered. Then, clearer: “Livvy Yass.”

Marcus’s smile became a thing of pure, chilling delight. He leaned back, spreading his arms along the top of the booth. “Livvy Yass. Perfect. It suits you.”

Derrick snorted, shaking his head. “Man, you’re weird. I’m getting another round.”

The spell broke, but it was a fragile, temporary fix. Paula followed Derrick to the bar, leaving Keith alone in the booth with Marcus. The noise of the bar rushed back in—clinking glasses, laughter, the jukebox switching to a mournful country song.

Marcus didn’t move. He just kept watching Keith, that smile still playing on his lips.

“You shouldn’t be ashamed, Keith,” Marcus said, his tone conversational, but every word felt loaded. “It’s just a different kind of truth. A purer one. All that masculine performance… it’s exhausting, isn’t it? The fighting, the posturing. Livvy doesn’t have to fight. Livvy just… receives. She exists to be pleasured. It’s freedom.”

Keith said nothing. He felt sweat bead under his arms. He wanted to leave, to run back to his empty, silent apartment and bolt the door. But his limbs felt heavy, leaden. He was pinned by Marcus’s gaze.

“Don’t worry,” Marcus said softly, as Derrick and Paula returned with sloshing glasses. “Your secret’s safe with me.” He winked, a quick, conspiratorial flash. “For now.”

The rest of the hour blurred. Keith drank his fresh whiskey too fast, the alcohol doing nothing to settle the chaotic swirl in his gut. He laughed too loud at Derrick’s jokes. He avoided looking at Marcus, but he could feel the coach’s eyes on him the entire time, a constant, warm pressure on the side of his face.

When they finally stumbled out into the cool night air, the relief was physical. Keith breathed in deep, trying to clear his head.

“Need a ride, Keith?” Marcus’s voice came from behind him, too close.

“I’m good. I walked,” Keith mumbled, fumbling for his keys.

“Suit yourself.” Marcus clapped a heavy hand on his shoulder. The grip was firm, possessive. It lingered a second too long. “Sleep well, Livvy.”

Keith froze. The name, spoken aloud in the real, non-drunk world, was an electric shock. He turned, but Marcus was already walking away, whistling that country tune, his broad shoulders rolling with an easy, confident rhythm.

Keith stood alone under a flickering streetlamp. The dive bar’s sign cast a weak pink glow on the pavement at his feet. He looked down at his hands—big, rough, teacher’s hands. He tried to see them differently, to imagine them with glossy pink nails, delicate, trembling. A wave of nausea twisted through him, part revulsion, part something else—a terrifying, liquid thrill.

He started the long walk home, every step feeling less sure, the image of Marcus’s predatory smile burned onto the back of his eyelids, the name Livvy whispering in his ear with the night breeze.

The walk home was a fever dream. Each crack in the sidewalk seemed to whisper Livvy. The rustle of leaves in the night breeze sounded like the slip of silk against skin. Keith’s heart hammered against his ribs, a trapped thing fluttering in a cage of bone and flannel. Marcus’s smile lingered in the dark behind his eyes, a hook set deep.

His apartment building loomed, a bland rectangle of concrete and indifference. The key fumbled in the lock. Inside, the silence was absolute, and for a moment, he just leaned against the closed door, breathing in the stale scent of his own lonely life. The shame from the bar curdled in his gut, but beneath it, a hot, insistent current pulled at him. It was the same current that had drawn his confession out—a riptide he’d stopped fighting years ago.

He didn’t turn on the main light. A dim lamp in the corner cast long shadows across the living room. It illuminated the ordinary things: a stack of ungraded papers on the coffee table, a teacher’s edition of To Kill a Mockingbird, a remote control. It also illuminated the discreet, locked trunk at the foot of his bed.

Keith’s mouth went dry.

He crossed the room, his footsteps loud in the quiet. The click of the trunk’s latch was a gunshot in the stillness.

Inside, folded neat and waiting, was another world.

The shapewear came first, a slick, compressive second skin that cinched his waist and smoothed the hairy planes of his torso into something softer. He shivered as it tightened, the pressure a familiar embrace. Next, the breastplate. The F-cup silicone was cool and heavy against his chest. He adjusted it, his big hands clumsy on the smooth curves, filling out the cups until the weight felt right, real. A phantom sensation of fullness bloomed there.

The inverted chastity device was polished steel. His hands trembled as he fitted it, the complex locks clicking shut with finality. The familiar, vulnerable ache immediately began, a constant reminder of surrender. He was locking Keith away. Livvy didn’t need him.

At the vanity—a piece of furniture that had no logical reason in a forty-six-year-old teacher’s bedroom—he began the paint. Foundation smoothed over his stubble, contour sculpted his jaw into a softer heart, eyeshadow in pinks and violets bloomed across his lids. False lashes fluttered. Lipstick, a glossy, perfect cupid’s bow. Each stroke of the brush was a meditation, a ritual erasure. The acrylic nails clicked on the tabletop as he worked, long and pink, foreign extensions he had learned to use with delicate precision.

The wig was last, a cascade of pink and violet synthetic hair that fell past his shoulders. He settled it, adjusting the fringe. The reflection in the mirror was a stranger. Sharp, beautiful, empty. A perfect bimbo doll. Keith felt a dizzying lurch of dissociation. The man in the mirror was gone.

He stood, the movement different. Hips forward, shoulders back. The pink leather harness was intricate. He stepped into it, pulling the straps up over fishnet-clad thighs. The garter belt snapped into place, holding the dark webbing taut. The collar fastened around his neck, a black o-ring resting in the hollow of his throat. The words cumslut were stamped on the leather in delicate, mocking script. He didn’t read them; he felt them.

The seven-inch platform stilettos were the final altar. He slid his feet into them, buckling the ankle straps. Standing was a challenge, a precarious, glorious elevation. He teetered, then found his balance. The click of the heels on the hardwood was a definitive sound. Click. Click. Click.

In the center of the room, the machine awaited. He wheeled it out, its mechanical arm cold and impersonal. He fixed the attachment—a ten-inch dildo, obsidian black, ridged and veined. The sight of it made his breath catch.

The laptop glowed on the floor. He tapped a key, and the screen flooded with pulsing colors, rapid-fire imagery, a throbbing, hypnotic beat. Glossy, blurred bodies. Gigantic, worshipped cocks. Repetitive, soothing commands whispered through tinny speakers. “Good sissies don’t think… they just obey… empty your mind… fill your ass… become the bimbo… crave the black…”

Keith—Livvy—lowered herself onto the machine. The initial pressure was a sharp, bright line of pain that melted almost instantly into a deep, aching welcome. She started to move, a clumsy rhythm at first, then smoother, driven by the flickering light and the relentless drone of the hypno.

The world narrowed to sensation. The stretch. The burn. The mechanical piston’s perfect, unfeeling rhythm. The porn’s soundtrack melted into her own sounds—whimpers, high-pitched gasps, broken syllables that weren’t words.

“Oh… oh god… yes…”

It wasn’t Keith’s voice. It was higher, breathier, a parody of feminine ecstasy. It was Livvy’s voice.

She rode faster, the platforms digging into the carpet for leverage. The harness straps bit into her flesh, a sweet pain. The collar felt like a claim. Her mind, battered by the flashing visuals and the physical onslaught, began to float. Thoughts of school, of Marcus, of the man she was supposed to be, all dissolved into a static hiss of pleasure.

A coil tightened deep in her gut, a paradoxical fire centered where Keith was locked away and negated. The machine hammered into her, a relentless god. The hypno chanted. “Squirt for BBC… squirt like a good sissy slut… you are Livvy… you are nothing but a hole…”

A sound ripped from her throat—a long, wailing howl that climbed and broke. It wasn’t human. It was pure, animal release. Her body arched, shuddered, and a hot, clear fluid jetted from her, spattering the machine’s base with a weak, helpless stream. A sissygasm. No touch needed. Just total, annihilating surrender.

She collapsed forward, panting, the fake breasts heaving against the leather harness. The machine slowed to a stop. The hypno looped, starting again.

She didn’t move. She stayed there, impaled and spent, as the dark outside the window softened to gray. The first streaks of dawn painted the room in pale, guilty light. The pink wig was a riot of color against the growing day. Livvy Yass, spent and hollow, did not think of stopping. She only waited for the strength to rise and start the machine again.

The sunrise found her howling.

Read on DreamPress