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Please see Mature Crossdresser is Owned Part 2

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By *aninnylons OP   TV/TS
7 weeks ago

Ipswich

The numbers on the screen blurred into a meaningless drizzle of light. £2,400. The final bid.

A username he didn’t recognize—‘SilverFoxHenderson’—had won the right to his Monday. The screen went dark. Gary’s hand, still a comforting, terrifying weight on his shoulder, gave a final squeeze. “Mr. Henderson is a man of particular taste. He prefers quiet. Obedience. He’ll be here at eight.” The words were a sentence, a promise, a threat.

The day passed in a haze of anxious preparation. Gary bathed him, the water scalding, then chilling. He was shaved again, every inch of him smoothed to a poreless perfection. The outfit chosen was not the intricate lace of his time with Edgar, nor the decadent silk of the group. It was simple, stark. A plain black satin chemise that fell to mid-thigh, sheer black stockings, and nothing else. No panties. No cage. Gary had simply looked at his soft, vulnerable flesh and said, “He won’t require that. You’ll be kept… occupied.”

At eight o’clock precisely, a quiet knock echoed through the cottage. Gary ushered in Mr. Henderson. He was , perhaps in his late sixties, with a lean frame, a head of striking silver hair, and eyes the colour of flint. He carried an air of quiet authority that didn’t need to shout. He wore a perfectly tailored suit, the fabric whispering as he moved.

“Gary,” he said, his voice a dry, rustling leaf. “He’s ready?”

“He’s all yours, sir,” Gary replied, and with a last, lingering look that promised a debrief, he was gone.

Mr. Henderson’s flinty eyes appraised Colin, who stood trembling in the center of the room. The silence stretched, thick and heavy. He didn’t circle. He didn’t touch. He simply looked, his gaze a physical pressure that made Colin feel utterly transparent.

“Turn around,” he said, the command soft but absolute. “Bend over. Place your hands on the coffee table.”

Colin’s heart hammered. The position was brutally exposing, the hem of the chemise riding up to reveal everything. He heard the rustle of clothing, the clink of a belt buckle. A cool, slick droplet of lubricant landed on his exposed cleft, making him jump.

“Be still,” Mr. Henderson murmured. His fingers, surprisingly smooth for his age, spread the cool gel, not teasing, not preparing, simply anointing. He positioned himself, the head of his cock—slender, elegant, and rock-hard—pressing against the tight furl of muscle. “You will not make a sound unless I give you permission. You will take what I give you. Is that understood?”

Colin could only nod, a frantic bob of his head, his knuckles white on the table’s edge.

“Good.”

There was no slow push, no gradual yielding. Mr. Henderson simply… entered. It was a single, fluid, unstoppable motion that buried him to the root in one smooth stroke. The air left Colin’s lungs in a silent shudder. The stretch was exquisite, a deep, filling pressure that was more intense for its lack of ceremony. He was just… taken.

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By *aleuk1965Man
7 weeks ago

newhall

I really hope there's more to come?

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By *ernne67Man
7 weeks ago

Shoeburyness

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By *ocklover50100Man
6 weeks ago

Holsworthy

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By *oLadyTV/TS
6 weeks ago

crewe

👏👏👏👏👏

On the edge of my seat…….dribbling

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By *ohnny 52TV/TS
6 weeks ago

Middlewich

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By *aninnylons OP   TV/TS
6 weeks ago

Ipswich

And then he began to move. His rhythm was not punishing, not frantic. It was a slow, deliberate, metronomic pistoning. Each withdrawal was almost complete, each thrust a full, deep re-occupation. It was maddening. There was no building wave, just a constant, plateaued state of being thoroughly, relentlessly used. Colin clenched his jaw, obeying the order for silence, though soft breaths hissed through his nose. His own cock, free and ignored, hung heavy and aching between his legs.

Mr. Henderson’s hands rested on Colin’s hips, not gripping, just anchoring. His breathing was even, controlled. He was a machine of pure, focused sensation. He shifted his angle minutely, and on the next thrust, the head of his cock grazed that devastating spot deep inside.

A broken gasp tore from Colin’s lips before he could stop it.

The rhythm stopped instantly. Mr. Henderson froze, buried deep. “I said no sounds,” he reminded him, his voice still calm. His hand came down on Colin’s left buttock, not a hard slap, but a firm, stinging spank that echoed in the quiet room. The shock of it, the shame, sent a jolt of pure heat straight to Colin’s groin.

“I’m sorry, Sir,” Colin whimpered.

“I know,” Mr. Henderson said. And he began again, the same slow, measured pace.

This time, when he found that spot, Colin bit his lip until he tasted blood, determined to be good. He focused on the sensation, the impossible fullness, the slick sound of their joining, the contrast of the cool air on his exposed skin and the burning heat inside him. The denial of noise made the pleasure more internal, a silent scream building in his core. His untouched cock leaked a steady stream of pre-come onto the rug below, a testament to his aching need.

Mr. Henderson’s pace never changed. He fucked with the patience of a man who had all the time in the world, drawing out his own pleasure, and in doing so, drawing out Colin’s torment into an unbearable, beautiful agony. Colin’s thighs began to tremble with the strain of holding the position, with the effort of staying silent.

Just when Colin felt he might collapse, Mr. Henderson’s rhythm finally fractured. His thrusts became slightly quicker, deeper, his breathing harsher in Colin’s ear. One hand snaked around Colin’s hip, fingers wrapping around Colin’s dripping, neglected cock. He didn’t stroke it. He just held it, a tight, possessive fist around the base, a promise of nothing.

“Now,” Mr. Henderson grunted, his composure finally breaking. “Now you may come.”

The dual sensation—the final, deep thrusts hitting his core and the firm, denying grip on his cock—was the trigger. Colin’s orgasm exploded out of him, a silent, convulsive wave that had him seeing stars, his body clenching violently around the cock still pumping its own release deep inside him. It was a climax of pure submission, of being used exactly as his owner saw fit.

Mr. Henderson held him through the aftershocks, then gently withdrew. He tucked himself back into his impeccable trousers, righted his suit jacket. He looked as composed as when he’d arrived, save for a slight flush on his neck. He placed a card on the coffee table. “My number. Leo will arrange the transfer of the rest of the week. A… satisfactory evening.”

And he was gone, leaving Colin slumped over the table, shaking, spent, and more profoundly owned than ever.

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By *unwithuMan
6 weeks ago

Manchester

Brilliant

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By *ohnny 52TV/TS
6 weeks ago

Middlewich

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