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The Sissy's Itch

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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 4: The Photo and the Promise

The silence after the door clicked shut was absolute, and within it, Jamie ceased to be a person. He was a collection of sensations floating in the plush dimness. The ache was a deep, throbbing bass note, a resonant echo of the violation that seemed to originate from his very core and radiate outward, making his limbs feel heavy and foreign. He could still feel the ghostly stretch, the burn of that final, spit-slicked re-entry.Slowly, painfully, he pushed himself up on the bed. The silk sheets were cold and sticky in patches beneath him.He looked down at the ruin of himself. Between his thighs, the lace panties were torn, damp, and crusted. His skin was blotchy, marked by fingerprints that were beginning to purple—on his hips, his throat, his thighs. He gingerly touched the sore ring of muscle, gasping at the raw tenderness, then brought his fingers to his nose.The scent was unmistakable: sex, sweat, and Markus.

He stumbled to the bathroom, his gait wide and unsteady, supporting himself on furniture.The fluorescent light was a brutal reveal. In the mirror, a stranger stared back. Mascara was smudged into phantom bruises under hollow eyes.His lipstick was gone, bitten and kissed away. His reflection seemed softer, blurred at the edges, as if the night’s violence had sanded down his definition.

He didn’t shower.He was afraid the water would wash away the evidence, the proof that it had happened. Instead, he filled the sink with warm water and cleaned himself with a washcloth, wincing as he dabbed between his legs.The water in the basin turned milky. He saw the faint, reddish smear of a tiny tear. A jolt of fear was immediately swamped by a perverse thrill.It was real.He had been taken, thoroughly.

Back in the bedroom, he pulled the ruined lace down his legs and dropped them on the floor. He crawled into the center of the bed, naked, and pulled the heavy comforter over his head. In the dark, warm cave, the scent of Markus was overpowering. He breathed it in, and his body, traitorously, stirred.A faint, dull throb of interest from his spent cock. The empty ache in his ass clenched around nothing, a palpable hunger.

Sleep was a fracturing thing, broken by dreams of being pinned, of overwhelming size, of a voice telling him what he was. He woke often, each time reaching behind to touch himself, as if to confirm the landscape of his body had been permanently altered.

The sharp rap on the door at precisely eleven the next morning sent a electric jolt through him. He’d been sitting in a robe by the window for hours, watching the city sweat, too sore to move much, too wired to rest.He opened the door.

Markus filled the frame, fresh in a tight black t-shirt and jeans, a small duffel bag slung over his shoulder.He looked like a different man—clean, composed, sharply handsome. His eyes swept over Jamie, taking in the robe, the tousled hair, the fragile posture. A slow, knowing smile spread across his face.

“You look like you got hit by a truck,” he said, his voice a low rumble.He stepped in without waiting, his presence immediately reclaiming the space. The room shrank around him.

“I feel like it,” Jamie whispered, closing the door and leaning against it for support.Markus dropped his bag and turned, appraising him. “Walk for me.”

Confused, Jamie took a few hesitant steps into the suite.

“Wider,” Markus commanded, his eyes fixed between Jamie’s legs. “Let me see how you’re carrying me today.”

Jamie felt his face flame. He tried to adjust his stance, the soreness flaring, a visible wince crossing his face. Markus nodded, a connoisseur satisfied with his work.“Good.” He stepped closer, cupping Jamie’s chin.“You thought about it? All night?”

Jamie nodded, unable to lie. “Yes.”

“What did you think about?”

“You,” Jamie breathed.“What you did. What you called me.”

Markus’s thumb brushed his lower lip.“You liked it. Being my little whore.”

It wasn’t a question.It was a coronation.Jamie’s breath hitched. “Yes.”

Markus’s kiss was surprisingly soft, a contrast to the memory of him. It was possessive, deep, and tasted of mint. His hands went to the sash of Jamie’s robe, untying it, letting it fall open. He broke the kiss to look down, his gaze heated and focused. “Let’s see the damage.”

He led Jamie to the bed, pushing him down onto his back. He spread Jamie’s legs, his touch clinical yet intensely intimate.He leaned in, studying him.Jamie shut his eyes, unbearably exposed.

“Fuck,” Markus exhaled, a sound of pure appreciation.“It’s perfect. Still puffy. Red as hell.” He ran a single, thick finger along the outer lips, not entering, just tracing the swollen skin.Jamie jerked.“Sensitive?”

“Very.”

“Good. Means you remember.” Markus stood up, stripping off his shirt, then his jeans. His cock, thick and heavy, was already half-hard, rising against his stomach with a menacing promise. He fetched a bottle of lube from his duffel.“We’re doing this slow today. We got time. I’m gonna make you feel every fucking inch.”

He coated himself generously, the slick sound loud in the quiet room. Then he coated Jamie’s hole, his fingers pushing the cool gel inside, working it gently.Jamie arched off the bed, a moan torn from him. The preparation was almost worse than the assault—a tender violation that coiled the spring of anticipation unbearably tight.Markus positioned himself, pressing the broad head against Jamie’s entrance. He held it there, not pushing, just letting the pressure speak. “You tell me when you want it.”

Jamie looked up at him, at the dark, focused eyes, the beads of sweat already forming on his temples.The power dynamic had subtly shifted. He was being given a choice, a thread of control, and it made him feel even more owned.“Please,” Jamie whispered. “I want it. Now.”

Markus leaned down, bracing his weight on his arms, and began to push.It was a slow, excruciating invasion. The burn from yesterday was a live wire, and the sheer, stretching fullness was a breathtaking echo. Jamie cried out, his hands flying to Markus’s biceps, fingernails digging in. Markus paused, buried to the hilt, his jaw clenched.“Breathe, princess.Just breathe into it.”

Jamie tried. He sucked in air, focusing on the sensation of being split open, owned, used. As he relaxed microscopically, Markus began to move. It was a deep, rolling grind, a far cry from the punishing pistons of the night before. Each withdrawal was a near-total loss, leaving him gaping and empty, each thrust a deliberate, soul-searing reclaiming. Markus watched his face, studying every flinch, every gasp.

“That’s it,” Markus murmured, his voice strained with his own control.“Take it.Your little sissy cunt is sucking me right back in. Feel that? It’s hungry for it.”

The vulgar words, delivered in that low, almost gentle tone, undid Jamie completely.Tears leaked from the corners of his eyes. The pain was transmuting, melting into a deep, resonant pleasure that was rooted in the ache itself. He was being remade from the inside out, slowly, thoroughly.

Markus’s rhythm began to falter, his control slipping. The thrusts became sharper, deeper, hitting a spot inside Jamie that sparked white behind his eyelids.“Shit,” Markus groaned, his composure crumbling. “You’re too fucking tight. Even like this.”

He hooked Jamie’s legs over his shoulders, changing the angle, and drove in hard.The slow burn exploded into a conflagration. Jamie screamed, a raw, unfiltered sound, as Markus fucked him in earnest now, the bed slamming against the wall in a steady, brutal cadence. The gentleness was gone, burned away by a mutual, desperate need.Markus was grunting, filthy, beautiful words. “Take that cock, you slut… milk it… gonna fill this used hole up again…”

Jamie was babbling, a stream of “yes” and “please” and “more,” his own neglected cock aching and leaking between them. He was hurtling toward a peak that had nothing to do with friction, everything to do with surrender.Markus’s thrusts became erratic, his body locking rigid. With a final, seismic drive, he buried himself and erupted, a hot, pulsing flood that Jamie felt as a profound, internal claim. The sensation triggered Jamie’ own climax, a dry, wrenching convulsion that ripped through him without a single touch, leaving him shuddering and spent.

Markus collapsed on him, a heavy, sweaty warmth, his breath hot on Jamie’s neck.They lay there, fused together, for a long time. The city’s hum was the only sound.Finally, Markus shifted, pulling out slowly. Jamie whimpered at the loss, at the sudden, hollow coolness.Markus looked down at him, his expression unreadable. He brushed a damp strand of hair from Jamie’s forehead.

“You okay?”

Jamie just nodded, his throat too tight for words.

Markus cleaned them both up with a warm cloth from the bathroom, his movements efficient but not unkind. He dressed in silence while Jamie watched, a strange, fragile connection hanging in the air between them.

Before he left, Markus handed jamie the duffle bag

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