Cover of The Sissy's Itch

The Sissy's Itch

Read the story

5 chapters · 8534 words · Read 0 times

jamie is a 20 year old skinny short feminine boy who decides to experiment with sex. Hes not sure but he would like to feel what its like to be the passive partner. He will fly to bangkok go to a hotel shave his body, do his make up and dress like a total chastised sissy. After he gets all dressed up he will arrange a meeting with markus a 6'5" nigerian man with a 11 inch thick cock whose escort review are wild. He is nervous (to the point of shaking) and not sure what he is getting into but he wants to know.

Chapter 3: The Collapse and the Confession

The cold seeped into him from the polished floor tiles, a sharp contrast to the furnace still radiating between his legs. Jamie trembled, a full-body shiver that started in his overworked thighs and rattled his teeth. He heard the bathroom faucet run, the mundane sound absurd in the wreckage of the room.

Markus returned, not with the promised towel, but standing there, his imposing frame relaxed, watching him. He was still naked, still semi-hard, glistening with their combined sweat and the evidence of what he’d done. He looked like a statue of a conqueror.

“Up,” Markus said, the single syllable devoid of its earlier growl but leaving no room for disobedience.

Jamie tried. His legs were water, his muscles unrecognizable. He pushed on the ottoman, his arms buckling, and stumbled. Markus’s hand shot out, not to help, but to fist in his hair, right at the crown. The pain was bright and anchoring. He used it to haul Jamie upright, dragging him stumbling until they both faced the large, streaked mirror.

Their reflection was a brutal portrait. Jamie, dwarfed, smeared and broken, held vertical only by the grip in his hair. Markus, behind him, a monument of used power. Jamie’s eyes were wide, glazed, desperately avoiding his own.

“Look at you,” Markus said, his voice low and conversational, as if discussing the weather. He gave Jamie’s hair a slight tug, forcing his head to stay up. “Fucking ruined. Look.”

Jamie’s gaze skittered across the glass—the smudged makeup, the tear-tracks, the blotchy skin—before landing, inevitably, on his own eyes. They held a vacancy that scared him.

Markus’s free hand drifted down, over Jamie’s flat stomach, pressing again where he had before. Jamie flinched, a fresh wave of sensitivity rolling through him.

“Still full of me,” Markus murmured, almost to himself. Then his other hand released Jamie’s hair only to snake around his throat, not squeezing, just cradling the jaw, tilting his face. Their eyes met in the mirror. “Now. Tell me what you are.”

The command hung in the musk-thick air. Jamie’s mouth was dry, his tongue a useless piece of cloth. He swallowed, the motion painful against Markus’s forearm.

“I…” The word was a croak.

Markus’s hand on his stomach slid lower, fingers combing through the damp, tangled lace at Jamie’s groin before slipping between his legs from the front. Two thick fingers found his swollen, slick entrance, pressed against the sensitive, stretched ring of muscle from the outside. Jamie gasped, his knees threatening to buckle.

“What are you?” Markus repeated, his voice hardening. He pushed a finger in, just the tip, a teasing, cruel reminder of the gaping emptiness inside that still pulsed with the ghost of him.

The invasion, from this new angle, this clinical probe, broke something loose. The words, practiced in secret, shameful fantasies, tumbled out in a broken whisper. “A sissy.”

“Louder.”

“A sissy slut,” Jamie choked, the obscenity feeling both alien and devastatingly true on his lips.

Markus’s reflection showed a flash of white teeth. He pushed his finger in deeper, twisting. “Made for what?”

Jamie’s breath hitched. He watched his own face flush a deep, humiliated red. “For… for cock.”

“What kind of cock, princess?” Markus’s other hand tightened minutely on his jaw. His own considerable length, which had begun to soften, was stirring again against the cleft of Jamie’s ass, thickening with a lazy, inevitable intent.

The answer was the core of it, the secret fuel for a thousand late-night searches, the dark magnet that had pulled him across oceans. Saying it aloud here, now, in the aftermath, felt like signing a confession. He squeezed his eyes shut.

“Eyes open,” Markus snapped, and Jamie’s flew open, meeting his own terrified gaze. “Say it.”

“Black cock.” The words were a ghost of sound.

“Again.”

“Black cock!” Jamie cried out, louder, the sound bouncing off the mirrors and velvet.

“Good boy.”

The approval was a drug, instantaneous and sickeningly sweet. Markus withdrew his finger, and before Jamie could process the loss, he was spinning him around, pushing him back over the ottoman, the same position, his exposed ass presented to the cool air. Jamie braced himself, expecting the immediate, brutal re-entry.

It didn’t come.

Instead, Markus’s hands were on him again, spreading him wide, thumbs on his inner cheeks. Jamie felt unbearably open, displayed.

“Look at this,” Markus said, a whistle of genuine appreciation in his tone. “Puffy. Red. Used. Leaking my shit already.” He ran a thumb over the abused rim, and Jamie jerked, a spark of raw sensation shooting through him. “Still hungry, though. Isn’t it?”

He wasn’t asking Jamie. He was stating a fact. Jamie felt it, a deep, internal clench around nothing, a stupid, empty craving. He hid his face in the velvet, muffling a sob of pure shame.

Markus leaned down, his breath hot. “You want it again? Raw? Same hole?”

Jamie couldn’t speak. He nodded, a frantic, desperate little motion into the fabric.

“Then ask for it. Properly.”

Jamie’s mind blanked. What were the words? What did this man want to hear? The filthy script from his fantasies evaporated, leaving only raw, needy instinct. “Please… Please fuck me. Again.”

“Not good enough.” Markus straightened up. Jamie heard the wet sound of him spitting into his own palm, then the slick, deliberate stroking of his own cock. The sound alone made Jamie’s hole twitch.

“Please,” Jamie begged, turning his head to the side, voice cracking. “Please, sir. Fuck my sissy ass. Fill it up again.”

“Whose sissy ass?”

“Yours!” Jamie wailed, the possession tearing out of him. “It’s yours, just please…”

The blunt, broad head of Markus’s cock pressed against him. There was no lube this time, just spit and the residual slick from his own spend. The burn of the initial push was sharper, more immediate, a breathtaking claim of already-conquered territory. Jamie screamed, a short, sharp sound, as Markus sank in, inch by relentless inch, re-stretching the tender, yielding flesh.

Once fully seated, Markus paused, letting Jamie feel the absolute fullness, the heat, the faint ache that promised to blossom. He draped himself over Jamie’s back, his weight a crushing, comforting anchor.

“You take it so good,” he muttered into Jamie’s ear, his hips beginning a slow, deep roll. “This little cunt was made for this. Just to get stretched open and filled.” His pace increased, each thrust a little harder, a little faster, forging a path of fire through Jamie’s core.

Read on DreamPress

Write your own erotic story with AI