I milk him 6 times in a row with a prostate vibrator. Sloppy handjob with 5 ruined orgasms

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Title: “6 Times a Charm: A Prostate-pleasing Progression”

The scene opens with our submissive male subject, bound and helpless, his eyes lowered respectfully as he awaits his Mistress’s arrival. The room is dimly lit, a soft bassline thrumming from the speaker as she enters, clad in a sleek black catsuit that hugs her every curve. She appraises him hungrily before sauntering over, running a single gloved finger along his jaw.

“Today, my pet,” she purrs, “we’re going to explore your sensitive prostate. I’m going to milk you dry, again and again, until you’re a desperate, quivering mess. Sound good?”

He nods, too nervous to speak, and she chuckles, a delicious shiver running through him at the sound.

She produces a sleek, bejeweled vibrator from her pocket, and presses it to his lips. “Get it wet,” she commands, and he parts them obediently. The cool silicone rests on his tongue as she guides it deeper, letting him coat it in saliva.

“Good boy,” she croons, withdrawing the satisfied, throbbing toy. She presses it against his puckered entrance, looking into his eyes as she pushes it past the initial resistance. He gasps at the unfamiliar stretch, his body clenching, and he learns then, how different anal play is from vaginal.

“Breathe,” she orders, sliding the toy deeper until he’s stretched around the base. She begins to move it, and he feels the first shudderingly good pulse against his sensitive prostate. His cock leaps to attention, achingly hard, as she works the vibrating toy inside him.

“Look at you,” she teases, “so responsive. We’re barely started.”

She begins to fuck him with the toy, urgent shoves of her hips that make the jeweled butt plug hammer into his prostate, over and over. Pleasure bends him double, drives the breath from his lungs, as she brings him to the edge so quickly.

Just as his cock twitches, betraying his impending orgasm, she withdraws the toy, leaving him empty and aching. “Not yet,” she croons, prolonging his torment. “Not until I say so.”

The denial builds, a fierce pressure in his crotch, as she strokes him with steady pulls of her fist, pounding his prostate with the merciless toy. Over and over she takes him to the precipice, taunting him with denial. Panting, he curls around the toy, desperate for relief, as she brings him to ruin again and again.

By the fourth time, his cock is so sensitive that tears leak from his eyes with each brush of her fingers against the head. His prostate clenches around the toy, devouring the vibrations, as sweat pours down his trembling body.

She fucks him harder, a”So how many times did you milk him?”
“I’ve lost count. At least six or seven. He was begging for mercy by the end, but I kept going until he was sobbing with the intensity. Made quite the pretty ruined wreck too.”

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