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Bar Pickup Turns Into Shemale Bitch Training

Trent hooks up with Giselle and her friend Divya for a hot night of shemale bitch training and repeated cum-covered fucking.

12 min read October 23, 2026New

Trent had been nursing the same whiskey for twenty minutes, the ice long melted, when the woman slid onto the stool beside him. He was twenty-eight, a software engineer who spent his days in quiet rooms and his evenings trying not to look as lonely as he felt, and the upscale bar was all low gold light and dark wood. She was the brightest thing in it.

“You look like a man who came here hoping the night would do something interesting,” she said. Her voice was low, warm, amused. “I’m Giselle. Thirty-two. And I don’t waste good evenings on small talk that goes nowhere.”

He turned, and the breath left him. She was stunning in a way that felt unfair: long dark hair, a mouth made for trouble, a black dress cut to show the smooth swell of her breasts and the line of her throat. Her perfume reached him before her hand did. She set two fingers on his wrist, light and sure, and the contact went straight through him.

“Trent,” he said. “And you’re not wrong.”

They talked. She asked what he built for a living and actually listened. He asked what she wanted from a Tuesday night and she smiled like she already knew. They ordered fresh drinks and sipped them slowly, neither of them chasing a buzz, both of them clear-eyed and sharp. Her knee found his under the bar. Her laugh came easy. When she leaned in to hear him over the music, her lips brushed the shell of his ear and stayed there a second too long.

“I like the way you look at me,” she murmured. “Hungry. Polite about it. I want to take the polite off you.”

“Then take me somewhere you can,” he said, and meant it.

Her apartment was a short ride away, high windows and a bed he could see from the door, sheets turned down as if she had expected company. She locked the door, kicked her heels aside, and faced him in the lamplight.

“Still want this?” she asked.

“Yes.”

She turned, and he drew the zipper down her back. The dress fell to her waist and then she pushed it the rest of the way off her hips and stepped out of it, bare from the waist up, skin golden in the low light, breasts full and high, nipples already tight. He stared, and she let him.

“Come here,” she said.

The kiss was not gentle for long. She opened for him, tongue sliding against his, one hand in his hair, the other dragging his palm up to her breast. He groaned into her mouth and bent, kissing the curve of one breast, then the other, licking a slow path to a nipple and sucking it into his mouth. She sighed, arching, fingers tightening in his hair.

“That’s it. Use your tongue. The other one too. Don’t be shy with me.”

He obeyed, licking, sucking, rolling the peaked flesh between his lips while his free hand cupped and squeezed. She stroked him through his pants, palm firm over the hard line of his cock, and he rocked into the touch, mouth still busy at her chest, tasting skin and the faint salt of her warmth.

“Bed,” she said, voice gone rough. “I want that cock in my mouth before I do anything else to you.”

She walked him backward, unbuttoned his shirt, and shoved his pants and briefs down together. His cock sprang free, thick and flushed, and she dropped to her knees on the rug as if the floor had been waiting for her. She looked up, eyes bright, and licked him from base to tip in one long stroke that made his knees threaten to give.

“Fuck,” he breathed.

“Soon,” she said, and took him in.

Her mouth was hot, wet, and devastatingly skilled. She sank halfway, then deeper, lips tight, tongue working the underside while her hand stroked what she could not yet swallow. She pulled off with a wet sound, spit shining on him, and smiled. “You taste good. Hold still.” Then she took him again, slower, deeper, until her nose brushed his stomach and her throat fluttered around the head. Trent’s hand hovered, then settled in her hair when she guided it there. She bobbed, sucking hard on the upstroke, humming, letting him feel every inch of that slick heat. Precum slicked her tongue. She swallowed around him and he swore, hips twitching, already close.

She pulled off before he could finish, kissing the head once, almost sweet. “Not yet. I have plans, and they require you desperate.”

She stripped him the rest of the way, shirt off his shoulders, shoes and pants kicked aside, until he stood naked and aching. Then she nodded at the bed. “Lie down. Arms up. Ankles apart. I’m going to tie you and give you a massage, and you are going to let me. Say yes if you want that.”

“Yes,” he said, already climbing onto the mattress. “Tie me. I want it.”

Soft cuffs waited at the posts, not an accident. She buckled his wrists above his head, then his ankles, snug but not cruel, checking each one with a finger slipped underneath. “Too tight?”

“No. Perfect.”

“Good boy.”

She stripped out of nothing more; she was already bare to the waist, still in dark panties that sat low on her hips. She climbed over him with a bottle of oil, warmed it between her palms, and started at his shoulders. The first pass was slow, thorough, thumbs digging into muscle he had not known was tight. She worked down his chest, circling his nipples until he gasped, then lower, over his stomach, deliberately avoiding his cock while it jerked against his belly, leaking. Oil gleamed on his skin. Her breasts brushed his ribs as she leaned. She massaged his thighs, the sensitive inner stretch, the crease of his hip, everywhere but where he needed her.

“Please,” he said, pulling at the cuffs. They held. “Giselle, please, touch me.”

“Begging already.” She sounded delighted. “We’ll get there. I like you like this. Helpless. Hard. Honest.”

She finally wrapped an oiled hand around his cock and stroked once, twice, slow enough to ruin him, then let go. He groaned, hips lifting into empty air. She did it again. And again. A massage that was also a tease, palms gliding over his balls, a fingertip tracing the seam behind them, never quite enough. He begged in a steady stream, please and more and I need it, and she drank every word, kissing his mouth between strokes, sucking his tongue, leaving him shaking and nowhere near finished.

Then she climbed off the bed and stood where he could see all of her.

“Watch,” she said.

She peeled the oil from her hands with a towel and began to move for him, unhurried. She was already bare above the waist; what remained was the slow theater of the rest. She turned, showing him the long line of her back, the curve of her ass in black panties, and hooked her thumbs in the waistband as if she might take them off. She didn’t. Not yet. She faced him again, ran her hands over her own breasts, down her stomach, and let them rest on her hips. The lamplight caught the front of the panties and Trent’s breath stopped.

There was a shadow there. Not a suggestion. A thick, heavy shape straining the fabric, outlined so clearly he could see the ridge of the head, the weight of the shaft, the way the cloth pulled taut and darker where it stretched. His eyes widened. His cock, already aching, throbbed hard enough to hurt.

“Giselle,” he whispered.

She smiled, slow and sure, and hooked the panties down. They slid over her thighs and dropped. What rose free was beautiful and massive: a thick, veiny cock, easily ten inches, flushed dark at the head, heavy enough to sway when she stepped closer, balls full beneath it. She wrapped a hand around the base and stroked once, letting him see every inch, the shine at the slit, the veins standing proud along the shaft.

“Shock looks good on you,” she said softly. “This is me. All of me. And I am not done with you.” She climbed onto the bed between his spread legs, that gorgeous cock resting hot against his oiled thigh, and leaned down until her mouth was at his ear. “My girlfriend and I are going to make you our bitch. Our eager little bitch. You’ll take our cocks, you’ll beg for them, and you’ll thank us. Say yes if you want that. Say it clear.”

His heart hammered. The cuffs held his wrists. Her cock pulsed against his skin, huge and real, and want rolled through him so hard he could barely speak. “Yes. God, yes. Make me your bitch. I want it. I want both of you.”

The bedroom door opened.

The woman who stepped in was just as gorgeous, thirty-two, dark-eyed, hair pinned up, a silk robe already slipping off one shoulder. She took in the scene—Trent bound and shining with oil, Giselle naked and hard between his thighs—and her mouth curved.

“You started without me,” she said. “I’m Divya. And you must be the pretty thing she texted me about.”

“He said yes,” Giselle told her. “Eager.”

Divya let the robe fall. She was naked underneath, breasts full, waist narrow, and between her legs a cock nearly as thick as Giselle’s, already swelling as she looked at him. She crossed the room, and Giselle rose to meet her. They embraced in front of the bed, bodies fitting, cocks brushing, and kissed deep and unhurried, tongues visible, hands in each other’s hair, moaning into it like they had all night and meant to use every minute. Trent watched, helpless, cock leaking onto his stomach, and the sight of them—two beautiful women, mouths open, cocks sliding together—made him pull at the cuffs and whimper.

They broke the kiss smiling, and turned to him together.

“Our bitch,” Divya said, climbing onto the bed. “Let’s use him.”

Giselle straddled his chest and moved up until that massive cock hovered at his lips. “Open. Tongue out. You wanted this.”

He opened. She fed him the head, thick and salty, and he licked, then sucked, jaw stretching as she pushed deeper. She was careful and relentless, one hand in his hair, fucking his mouth in slow strokes, letting him learn the weight of her, the way she filled him until his lips were tight around the shaft and his throat worked. “Good bitch,” she murmured. “Look at you. Taking it. So hungry.”

At the same time Divya swung a leg over his hips, gripped his cock, and sank down onto it in one smooth glide. She was tight and hot around him, slick, and the shock of being inside her while Giselle’s cock filled his mouth tore a moan out of him that vibrated around the shaft. Divya rode him hard, palms on his chest, breasts bouncing, her own cock slapping against his stomach with every drop of her hips.

“Fuck, he’s thick,” she gasped. “Giselle, his mouth looks perfect on you.”

“It is,” Giselle said, thrusting a little deeper, eyes on his face. “Breathe through your nose, baby. Take more. There. That’s our good bitch.”

They used him like that until his thighs shook and Divya was panting, clenching around him, until Giselle pulled out of his mouth shining and wet and he gasped for air, lips swollen, chin slick. Divya climbed off before he could come, stroking his cock once in farewell, and the two of them looked at each other with the same hungry idea.

“Turn him,” Divya said. “I want his ass.”

They unbuckled his ankles only long enough to roll him onto his stomach and refasten the cuffs, hips lifted on a pillow, ass up, wrists still bound above his head. Giselle’s oiled fingers found him first, circling, pressing, easing one in, then two, patient and thorough while he groaned into the sheets and pushed back.

“You want it,” she said. It was not a question.

“Yes. Please. Fuck me. Both of you. Make me your bitch.”

Divya knelt behind him, cock slick with oil, and pressed the broad head to his hole. She pushed in slow, inch by inch, stretching him open around that thick length until her hips met his ass and he was full, gasping, clutching the cuffs. She fucked him in deep, steady strokes, one hand on his hip, the other coming down in a sharp spank that made him yelp and clench.

“Count,” she said, and spanked him again.

“One—two—fuck—three—”

Giselle moved to his head, lifted his face, and slid her cock back between his lips. “While she fucks you, you suck me. That’s what a bitch does. Both ends. Open.”

He opened. They took him together, Divya driving into his ass, Giselle fucking his mouth, a rhythm that left him nowhere to hide and nothing he wanted to hide from. Spank after spank landed, heat blooming across his ass, each one making him moan around Giselle’s cock and push back onto Divya’s. They switched when Divya’s breath went ragged: Giselle pulled out of his mouth, Divya slipped free of his ass, and they traded places. Giselle’s bigger cock pressed in where Divya had opened him, thicker, deeper, and Trent cried out, the sound breaking into a plea.

“Please—please don’t stop—harder—I’m your bitch, I’m yours, use me—”

“Listen to him,” Divya said, feeding him her cock, salty and heavy on his tongue. “Begging like he was made for it.”

Giselle spanked him while she fucked him, palm cracking against oiled skin, each thrust punching a broken sound out of his throat around Divya’s shaft. They praised him and degraded him in the same breath—good bitch, pretty hole, look at you taking ten inches, such a desperate little slut for us—and he took every word, wanted every word, nodding as best he could with his mouth full. When they pulled out to stroke themselves over his back, he twisted to look, wrecked and shining.

“Cover me,” he begged. “Please. I want it. I want your cum.”

Giselle came first, groaning his name, thick ropes striping his ass and lower back, hot and heavy. Divya followed a moment later, cock jerking in her fist, painting his shoulders and the side of his face when he turned into it, some of it landing on his tongue. They were not finished. They stroked him through the mess, flipped him again, and used him through another round—Divya in his mouth while Giselle rode his cock until she came a second time across his chest, then both of them kneeling over him, cocks in their hands, working themselves until they spilled again, striping his stomach, his throat, his open mouth while he licked and thanked them and came so hard his vision whited out, untouched at the end except for the sight of them and the filth of their praise.

They stayed with him while he shook, kissing his temple, his swollen mouth, murmuring that he had done so well.

When the trembling eased, Giselle unbuckled the cuffs one by one, rubbing the marks at his wrists, and Divya did the same at his ankles. They kissed him tenderly, slow and deep, tasting themselves on his lips, no performance left in it, only warmth.

“Shower with us,” Giselle said, thumb stroking his cheek. “Then, if you want, you come back. We are not done training our bitch.”

Trent looked at the two of them, cum drying on his skin, body used and glowing, and the grin that broke across his face was pure satisfaction. “Yes. Shower. And the next session. I’m already eager.”

They helped him up, and as their hands closed around his, gentle where the ropes had been rough, he understood the night had never been about being taken at all — it had been about being kept.

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