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Oiled Japanese Ladyboys Buggering Each Other

Two best friends oiled and buggering each other.

11 min read November 13, 2026New

The private rooftop pool held the afternoon in a bright still sheet, and the only two people with a key to it were already half undressed by the heat. Estelle, twenty-two, lay on the wide lounger with one pale skinny arm flung over her eyes, her tiny white string bikini doing almost nothing to cover the narrow lines of her body. She was a petite Japanese trans woman, small-breasted, smooth-skinned, ribs showing when she breathed. Beside her, Roxanne—also twenty-two, also pale and skinny, also a Japanese ladyboy with a waist Estelle could nearly span in her hands—shifted onto her stomach and let the sun find the long bare stretch of her back. They had wanted each other since the year they both turned eighteen, a mutual pull neither of them had quite dared to name until the oil came out and the city noise dropped away below the parapet.

"Shoulders," Estelle said. She sat up, uncapped the bottle of sun oil, and poured a heavy stream across Roxanne's skin. It ran in thick glossy ribbons, far more than anyone needed for the sun, pooling in the hollow of her spine and sliding toward the ties of her black bikini bottom. Estelle set both hands to it. She spread the oil in slow circles over shoulder blades, down the channel of the spine, across ribs she could count. Roxanne made a small sound and pressed into the touch. When Estelle's palms slipped under the bikini strings and found the soft undersides of Roxanne's small breasts, Roxanne's breath went ragged.

"More," she said. "Don't be careful with it."

Estelle poured again until oil dripped from Roxanne's sides onto the lounger cushion. She worked it over the high curve of that narrow ass, thumbs dipping just under the bikini edges, and felt Roxanne's hips roll. Then Roxanne turned over, face flushed, dark eyes bright, and Estelle saw the front of the black bottoms already tenting. Roxanne's slim cock had begun to harden, lifting the thin fabric, the shape of her unmistakable in the sun. Estelle did not pretend she hadn't noticed. She tipped more oil into her palm and closed it over that rising heat, stroking through the cloth until Roxanne's cock stood fully stiff and the strings cut into her hips.

"Now you," Roxanne whispered.

She took the bottle and drowned Estelle. Oil sheeted over Estelle's collarbones, her small breasts, the flat of her stomach. Roxanne's hands were sure and shameless, rubbing until every inch of pale skin shone. When she reached the white bikini bottom she found Estelle just as hard, the slim length straining upward, a wet spot darkening the cloth where she leaked. Roxanne stroked her through the fabric, slow, then faster, oil making the glide obscene. Their eyes locked. Both cocks tented the ruined bikinis. The wanting that had lived between them for years finally had somewhere to go, and neither of them looked away.

They did not rush the next part, and that only made it worse. Roxanne leaned in until her oiled mouth was at Estelle's ear.

"I've wanted to fuck you since we were old enough to mean it," she said, plain and shameless. "I think about your ass when I jerk off. I think about putting my cock in you until you can't talk."

Estelle's laugh came out shaky. Her hand was still on Roxanne's cock through the black cloth, stroking. "Then stop thinking. I want you in me. I want to be in you. I want both, today, right here, until neither of us can get hard anymore."

"Say it again."

"I want you to bugger me," Estelle said, and the word felt filthy and perfect in the sun. "And I want to bugger you. Bare. With so much Vaseline we slide."

Roxanne kissed her. It was messy, oil-slick, all tongue, and Estelle moaned into it while their cocks rubbed together through the thin bikinis. Roxanne's fingers found the side ties of Estelle's bottoms and pulled. The white strings came loose. She peeled the soaked fabric down Estelle's skinny thighs and off, and Estelle's cock sprang free, pale, slim, shining with oil and precome, curving up against her flat stomach. Estelle returned the favor. She untied Roxanne's black bottoms and drew them down, watching that slim cock slap up against Roxanne's oiled belly, the head flushed darker than the rest of her pale skin. The bikini tops went next. Estelle's fingers shook a little on the knots, then Roxanne's small breasts were bare, nipples tight, and Estelle's own small breasts were bare too, oil running between them. They knelt facing each other on the lounger, glistening, cocks hard and dripping, nothing left between them but heat.

Roxanne reached under the lounger and brought up the large jar of Vaseline they had set there that morning, both of them already knowing how the day might go if they were brave enough to ask. She twisted the lid off. The smell of it was plain under the coconut oil. She scooped a thick glob onto her fingers and looked at Estelle.

"Turn around. Let me open you."

Estelle went to her hands and knees without hesitation, consent already humming in her throat as a yes. Roxanne's slick fingers found her hole and pushed, Vaseline making the slide easy, one finger then two, working the thick grease deep. Estelle dropped her head and moaned, pushing back for more. Roxanne stroked Estelle's cock with her free hand at the same time, oil and Vaseline and precome making a wet sound that carried across the empty roof. Then they switched. Estelle scooped a heavy handful from the jar and smeared it between Roxanne's cheeks, circling that tight pale hole before pressing in. Roxanne gasped and spread her knees wider. Estelle fingered her slow, then harder, two fingers, three, greasing her until she was open and shining, while her other hand pumped Roxanne's cock in long oily strokes.

"I can't wait," Roxanne said, voice breaking, eyes bright with want. "Put it in me. Bugger me. Now. I want it."

Estelle's own hole clenched around nothing, desperate, and her cock throbbed in Roxanne's grip. The jar sat open between them, half empty already, white grease smeared up both their wrists. They were done teasing. They were done with fingers. The only thing left was to fuck, and both of them were already nodding yes.

Estelle pushed Roxanne forward until her chest hit the lounger and her ass lifted, pale and shining, the hole already greased and fluttering. She scooped another thick load of Vaseline and smeared it over her own cock until the slim length gleamed white and slick, then packed more into Roxanne, two fingers twisting, opening her wider. Roxanne reached back and spread herself, eager, breathing hard.

"Deep," she said. "Don't tease me. I want all of it."

Estelle set the head of her cock against that tight ring and pushed. The Vaseline made her sink in one long glide, inch after inch, until her hips met Roxanne's skinny ass and she was buried to the root. Roxanne cried out, a raw pleased sound, and clenched around her. Estelle held there a second, feeling the heat, the grip, the way Roxanne's body tried to pull her deeper. Then she drew back and thrust, hard, and the lounger creaked under them.

She fucked her in doggy like she had been starving for it. Each stroke slapped oil and grease between them. Roxanne's small breasts swung, her fingers clawed the cushion, and her cock—untouched at first, hanging stiff and dripping—jerked with every thrust. Estelle reached under and found it, stroking in time, Vaseline and precome slicking her fist while she pounded Roxanne's ass. Roxanne sobbed her name and pushed back, taking it, begging for harder, for deeper, for Estelle not to stop even for a breath. The sound of it was wet and relentless. Sun flashed off their oiled shoulders. Estelle bent over her and kissed the nape of her neck and kept driving in, hips snapping, the whole length sliding home again and again until Roxanne was shaking and still asking for more.

"On your back," Estelle panted. "I want to see your face while I bugger you."

She pulled out, the withdrawal obscene and wet, and rolled Roxanne over. Roxanne's legs came up, skinny and shining, and Estelle hooked them over her shoulders and sank back in. Missionary let her see everything: Roxanne's flushed face, her open mouth, the small breasts mashed when Estelle leaned down to kiss her, the slim cock trapped between their stomachs, leaking onto both of them. Estelle stroked it while she fucked, long deep thrusts that punched little sounds out of Roxanne's throat. Roxanne stroked her in return whenever she could reach, hands clumsy with grease, both of them desperate and moaning into each other's mouths. Estelle changed the angle until Roxanne's eyes went wide and her cock jumped in Estelle's fist, and she stayed there, grinding deep, pounding that spot until Roxanne was babbling yes, yes, don't stop, fuck me.

They switched because neither of them could stand not being filled. Roxanne shoved Estelle down onto her back, greased her cock again with a heavy scoop from the jar, and lined up. Estelle held her own cheeks apart and nodded, hungry for it. Roxanne pushed in and Estelle's eyes rolled, the stretch bright and perfect, Vaseline letting that slim cock sink all the way until Roxanne's hips were flush against her. Roxanne fucked her hard from above, strokes deep and mean, one hand wrapped around Estelle's cock, pumping in time. Then she flipped her and took her in doggy, pounding until Estelle's arms gave out and her face pressed into the cushion, ass up, taking every stroke and pushing back for the next. They switched again. Estelle climbed on and rode Roxanne's cock facing her, grinding down while Roxanne thrust up and stroked her. Roxanne bent over the end of the lounger while Estelle stood behind her and drove in, one greasy hand on Roxanne's cock, the other locked on her hip. The jar tipped and spilled a white smear across the tile. They scooped what they could, re-greased, slid back in, frantic, laughing when they slipped, moaning when they didn't. Every time one of them pulled out the other was already turning, already offering, already saying now, again, me.

Estelle felt it build while she was buried in Roxanne again, doggy, strokes going short and vicious. She had let go of Roxanne's cock. She didn't need to touch it. Roxanne's whole body tightened, her hole clamping down in rhythmic pulses, and she came hands-free, cock jerking under her, thick stripes of come striping the lounger while she wailed into the cushion. The clench dragged Estelle over with her. Estelle slammed deep and came inside that gripping heat, untouched except by Roxanne's ass, pulsing until her thighs shook and her vision went white at the edges. They did not stop to recover. Roxanne, still hard enough to mean it, rolled Estelle onto her back and fucked her through the aftershocks, stroking nothing, just pounding, until Estelle came a second time hands-free, cock spurting across her own oiled stomach while Roxanne buried herself and finished with a broken groan, filling her.

After that the erections failed them. They lay panting, cocks softening against their stomachs, holes slick and open and still aching to be used. Roxanne laughed, breathless and wrecked, and reached into the bag they had stashed under the lounger that morning for exactly this.

"Then we use these. I still want you. You still want me."

"God, yes."

Two huge silicone strap-on dildos, thick and long, pale and heavy, with harnesses ready. They wiped their hands on a towel just enough to manage the straps. Estelle stepped into hers first, cinching the harness tight over her softening cock, the massive toy jutting out absurd and perfect from her skinny hips. Roxanne did the same, buckling it snug, the weight of it making her narrow waist look even smaller. They kissed once, filthy with oil and the taste of each other, and then Estelle bent Roxanne over the lounger again and pressed the huge greased head to her hole.

It took a slow brutal push. Roxanne bore down, moaning loud enough to bounce off the water, and the thick silicone sank in, stretching her wider than Estelle's cock ever had. Estelle did not gentle it once the head popped through. She gripped Roxanne's hips and railed her, long hard strokes, the harness slapping pale skin, the toy glistening with Vaseline as it vanished and reappeared. Roxanne screamed her pleasure into the cushion and reached back to pull Estelle deeper, taking the whole massive length, shaking, loving it. They moved without pausing. Roxanne on her back, legs hooked high, the huge dildo plunging while she clutched Estelle's arms and begged for harder. Roxanne riding, sinking down until the base kissed her ass, bouncing, small breasts jumping, moaning so loud the sound skipped across the pool. Then they switched without pulling the harnesses off. Roxanne drove the second massive toy into Estelle, doggy first, deep and relentless, then missionary with Estelle's ankles by her ears, the stretch so full Estelle could only gasp and nod and take it. Estelle climbed on and ground in slow devastating circles, the toy seated to the root, before Roxanne flipped her and fucked her prone, hips snapping, the full length buried on every stroke. They took each other standing at the edge of the lounger, one bent double, then on their sides with a thigh hauled high, then Estelle straddling Roxanne and riding while Roxanne thrust up hard enough to knock the breath from her lungs. Every position they could fold their skinny bodies into. The toys never softened. They came again and again from the relentless stretch and pound, holes clenching around silicone, voices breaking, shared and shameless and loud, until the sun had dropped toward the parapet and their bodies shook with too much pleasure to name.

They collapsed at last onto the oil-slick lounger, too wrung out to pull free, and rolled onto their sides facing each other so the huge glistening dildos stayed buried to the base in one another. Harnesses snug. Thick silicone holding them open. The pool had gone the color of hammered copper. Estelle found Roxanne's mouth and kissed her lazy and deep, and Roxanne kissed back, one hand on Estelle's skinny hip, guiding a slow grind that worked those massive toys in tiny shifts. Neither of them had the strength for another pounding. They did not need it. The fullness was enough—the stretch, the heat, the way each small roll of their hips pressed the silicone deeper and made them both whimper into the kiss. Come and oil and Vaseline slicked the cushion under them. Their softened cocks rested against each other's stomachs, spent, while the toys did what their bodies no longer could. They kept kissing. They kept grinding. They savored the last deep fullness as the light went gold and then thin.

The sun went down on two best friends still split to the root on each other, and neither of them would ever be able to pretend they were only friends again.

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