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Virgin Ladyboy's Colonic Prep and Tranny Buggery

Virgin ladyboy begs a dominant trans woman to thoroughly clean and stretch his untouched ass before she brutally buggers him.

8 min read November 03, 2026New

Stefan stood in the hallway outside Harriet’s apartment with his pale hands clenched and his pulse hammering in his throat. Nineteen, slim as a reed, blue-eyed and blonde, he had dressed in a soft gray tee and tight black pants that did nothing to hide how nervous he was. The door opened before he could knock twice.

Harriet filled the frame. Twenty-eight, brunette, sharp-jawed and broad through the shoulders, she looked him over with a slow, hungry sweep and smiled like she already owned him. “You’re right on time, pretty boy. Come in.”

He stepped inside. The apartment was warm, dim, and private. No one else was there. She shut the door and leaned against it, arms folded, the heavy shape of her cock already obvious under her pants.

“Say it,” she said. “I want to hear you ask.”

Stefan’s voice came out thin. “I’ve never been fucked. Never had anything in my ass. I want you to take it. But I need you to clean me first. Really clean me. Stretch me. I don’t want to tear when you put that thick cock in me.”

Harriet’s grin went mean and pleased. “Eight inches. Thick. And I’m not going to be gentle once I’m in. You still want it?”

“Yes.” He nodded fast, cheeks pink against his pale skin. “I want your cock. I want you to bugger me. Just… prepare me. Please.”

“Good.” She stepped close, caught his chin, and made him meet her eyes. “Bathroom. Clothes off. You’re mine until I’m finished with that virgin hole.”

He stripped with shaking hands. Shirt, pants, panties. His slim body was almost hairless, his cock already half-hard from the way she watched. Harriet stripped too, unhurried, and his breath caught when her cock swung free—long, heavy, visibly thick, the head flushed and the shaft already starting to rise. Eight inches, just as she had promised, and meaner looking than he had pictured.

“On the mat,” she said, and led him into the bathroom.

The colonic kit was already set out beside the tub: bag, hose, nozzle, warm water she had mixed herself. Harriet had him kneel, chest down, ass up, and she spread his cheeks with both hands. His hole was small, pink, untouched. She rubbed a little slick over the nozzle and pressed it to him.

“Breathe out,” she ordered. “I’m filling you.”

The nozzle slid in. Stefan gasped at the strange, firm intrusion, then moaned as warm water began to flow. It was slow. Harriet kept one hand on the bag and the other spread across his lower back, talking him through every cramp and rush. The water swelled inside him, heavy and intimate, until his slim belly felt tight and his cock dripped onto the mat. She held him there, massaging his stomach in slow circles, making him take the full load before she let him release.

They did it again. And again. Each fill left him cleaner, shakier, more aware of the empty ache that followed the flush. By the third time his hole was twitching around nothing, his blue eyes wet, his blonde hair stuck to his forehead. Harriet wiped him down, checked him, and hummed her approval.

“Clean,” she said. “Now we open you.”

She walked him to the bedroom with a jar of Vaseline and a row of dildoes already waiting on a towel. Stefan bent over the edge of the bed without being told, presenting his pale ass. Harriet scooped a thick load of the grease and smeared it over his hole, working it in with two fingers until the rim shone. The Vaseline was obscene, heavy, melting into him. She pushed one finger deep, then two, twisting, scissoring, listening to the wet sounds and the broken noises he made.

“Tight little virgin,” she muttered. “Not for long.”

The smallest dildo went in easy once her fingers had him slick. She fucked him with it in short, steady strokes, then swapped it for the next size. Stefan’s slim hips jerked. His cock leaked onto the sheets. Harriet didn’t rush. She coated each toy in more Vaseline, pressed the heads to his greased hole, and worked them in until his rim stretched shiny and wide. The third dildo made him sob. The fourth made him beg. She held that one buried, grinding the base against him, one hand wrapped around his leaking cock just long enough to keep him aching and denied.

“You feel that?” she asked, voice rough. “That’s nothing compared to me.”

“I want it,” Stefan panted. “Harriet, please. I’m ready. Fuck me. Take it.”

She pulled the toy out slow. His hole stayed open a second, pink and gleaming, before it fluttered shut. Both of them were shaking. Her cock stood fully hard now, thick and dark against her stomach, a fat bead of precum at the slit. She stroked herself once, smearing that slick down the shaft, and her jaw tightened.

“On the bed. Ass up. I’m done teasing.”

Stefan scrambled into place, chest flat, knees spread, blonde head turned so he could still see her. Harriet climbed up behind him. She scooped another heavy load of Vaseline and painted her cock until the whole eight inches shone, grease dripping off the head onto his tailbone. She notched that blunt crown against his prepared hole and gripped his slim hips hard enough to bruise.

“This is your cherry,” she said. “I’m taking it.”

She shoved.

The head popped through the tight ring and Stefan cried out, a sharp, helpless sound that broke into a moan as she kept driving. Inch after thick inch forced him open. The Vaseline made it filthy and wet, but her cock was so much hotter and harder than any toy. She didn’t pause to let him adjust. She sank to the hilt in one long, brutal push, her hips slamming his ass, her balls pressed tight to him, and held there while he shook.

“Fuck,” she growled. “Virgin hole swallowing me whole. Feel that? That’s me. All of me.”

“Yes—oh god—yes—” Stefan’s voice cracked. His fingers clawed the sheets. The stretch burned and bloomed into something devastating, a full, stuffed ache that made his cock jump and drip. “You’re so big. You’re in me. You’re actually in me.”

Harriet pulled back until only the head remained, watched his rim cling to her, then slammed home again. The smack of her hips against his pale ass filled the room. She set a hard rhythm, deep and mean, each thrust punching a moan out of him. Grease smeared between them, shiny on her shaft, shining on his cheeks, dripping down his thighs. She gripped his hips and used them like handles, yanking him back onto her cock every time she drove forward.

“Take it,” she snarled. “Take every inch, you pretty little slut. This ass was made to get buggered. Look at you opening up. Listen to how wet you are.”

The sounds were obscene—slick, heavy, the wet clap of her body against his. Stefan couldn’t form words anymore. He pushed back anyway, greedy, his slim frame jolting with every stroke. Harriet leaned over him, one hand fisted in his blonde hair, the other still locked on his hip, and fucked him harder. Her cock dragged over the sweet spot inside him on every thrust and his blue eyes went wide, unfocused, mouth open on a constant broken sound.

“That’s it,” she said against his ear. “That’s your cherry gone. I’m wrecking it. I’m going to pound this hole until it remembers my cock.”

She straightened, spread his cheeks, and watched herself disappear into him. The sight made her thrusts rougher. She bottomed out again and again, grinding deep, making him feel the full thickness, the heavy swing of her balls against his own. Stefan’s cock swung and slapped his stomach, leaking a steady string onto the sheets. He was moaning her name, begging without shame, hips working back to meet her.

Harriet wasn’t finished claiming him. She pulled out just long enough to flip him. Stefan landed on his back with a gasp, legs falling open, hole clenching on nothing and shining with Vaseline. She shoved his knees toward his chest, lined up, and drove back in with one savage thrust. The new angle let her sink even deeper. His mouth fell open. His blue eyes rolled.

“There,” she panted, bracing over him. “I want to see your face while I fuck you. Eyes on me.”

He tried. Every hard stroke knocked the focus out of him. Harriet pounded him in long, powerful strokes, her brunette hair falling around her face, her thick cock splitting him open over and over. She watched his pale throat work, watched his slim chest heave, watched those blue eyes glaze and roll whenever she hit deep. Her hands pinned his thighs wide. The bed creaked. Grease and precum made a mess of both of them.

“Look at you,” she said, filthy and proud. “Virgin twenty minutes ago. Now you’re taking eight inches like a cock-hungry hole. You love it. Say it.”

“I love it,” Stefan sobbed. “I love your cock. Fuck me. Don’t stop. Please don’t stop.”

She didn’t. She hammered him, missionary and merciless, hips snapping, the head of her cock bullying that spot until his whole body jerked. His hands scrabbled at her arms, not to push her away—to pull her closer. She gave him everything, deep and fast, then slow and grinding, then fast again, using his body exactly how she wanted. His rim was swollen around her, stretched wide, gripping her shaft every time she withdrew. She spat a curse and fucked him harder for it.

“Gonna fill you,” she warned, voice breaking into a growl. “Gonna dump it deep in this freshly fucked hole. Stroke that pretty cock. Come while I breed you.”

Stefan wrapped a shaking hand around himself and pumped, fast and desperate, eyes locked on hers until another brutal thrust made them roll back again. Harriet buried herself to the hilt and stayed there, grinding, her thick cock pulsing as she started to come. The first heavy spurt flooded him. Then another. She groaned through her teeth and kept pumping shallow, stuffing load after load into his open passage until it was hot and full and leaking around her shaft.

Stefan cried out and came across his own stomach, stripes of cum painting his pale skin while her cock throbbed inside him and kept giving. She didn’t pull out. She stayed buried, hips jerking, milking the last thick pulses into him until his hole was packed with her cum and his hand was slick with his own.

Harriet looked down at the mess—his spent cock, his quivering thighs, her grease-shiny shaft still wedged in his ruined hole—and gave one last mean thrust that made cum squelch out around her.

“Keep it in,” she ordered, filthy and satisfied. “That load stays up your ass until I decide you’ve leaked enough.”

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