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Please see Mature Crossdresser is Owned Part 2

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By *aninnylons OP   TV/TS
2 days 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
10 hours ago

newhall

I really hope there's more to come?

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By *ernne67Man
10 hours ago

Shoeburyness

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