Celebrity Story Site
Stories & Art => Celebrity Stories => Singers => Topic started by: TheLW on February 04, 2026, 10:32:05 PM
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Losing the Bet
With Kylie Jenner and Madison Beer
Written by TheLW
Codes: MFF, Blowjob, Fingering
Disclaimer: This FICTIONAL story was written for entertainment purposes only.
Celebrity Row buzzed with energy, the game’s intensity reflected in the glow of arena lights. Timothée Chalamet leaned forward, eyes glued to the court, while Justin Herbert exuded a calmness, confidently keeping pace with every Lakers play. Kylie and Madison were sandwiched between them, laughing and whispering, but this time the conversation took on a more charged edge.
“So,” Timothée began, leaning toward Justin with a mischievous glint, “let’s make this interesting. The winner of the game... gets a threesome with both of them.”
Kylie’s jaw dropped. She blinked, unsure whether to laugh or protest. “Wait, what?”
Justin smirked, shrugging. “Totally serious. If the Lakers win, I call the shots. If the Knicks win, Timothée does. Simple enough.”
Kylie hesitated, feeling a sudden weight of uncertainty. “I... I don’t know. That’s... kind of extreme.”
Madison, sitting closer to her, leaned in with a playful grin. “Kylie, come on. It’s not like we have to say yes later if it’s not fun. But... imagine the thrill. The adrenaline. It’s a once-in-a-lifetime kind of gamble.”
Kylie chewed her lip, glancing at the court where the Knicks and Lakers were trading fast breaks. “I don’t know if I’m... that adventurous.”
Madison nudged her gently. “Hey, that’s why I’m here. I’ve got your back. And trust me, it could be a lot of fun. We’ll laugh, tease them, see where the night goes. No pressure, just a little adventure.”
Kylie’s shoulders relaxed slightly. She met Madison’s eyes and saw the spark of excitement there, the kind that makes a risky idea seem irresistible. She smiled nervously. “Okay... maybe... maybe we can try it. Just... go along with the energy of the night?”
“That’s the spirit,” Madison whispered, her grin widening. “Trust me, this is going to be memorable.”
Timothée, oblivious to the internal debate, was bouncing on his heels. “Come on, Knicks! Let’s seal this victory!”
Justin, calm as ever, sipped his drink and smirked. “Just wait. The Lakers aren’t done yet.”
The game intensified. Every three-pointer, every defensive block, every referee’s call made the air in the row crackle with tension. Kylie, still slightly hesitant, found herself laughing at Timothée’s over-the-top reactions, while Madison whispered encouragement and playful nudges, reminding her to enjoy the thrill.
By the fourth quarter, the score was tied 104-104. The arena held its collective breath. With only seconds left, the Lakers set up their final play. The ball swung around the perimeter, the clock winding down, and LeBron James launched a corner three.
Swish...
The final buzzer rang, scoreboard flashing 107-104, Lakers win. The arena erupted, fans screaming, but on Celebrity Row, all eyes were on each other.
Timothée froze, staring at Kylie with a mix of disbelief and fury. “Wait, hang on. No. This isn’t happening. I mean... I can’t...”
Kylie leaned forward, her voice calm, confident, and impossible to argue with. “Timothée, shut up. A bet is a bet. And I want this. I want a threesome with Justin and Madison.”
Timothée’s jaw clenched. “Are you kidding me? You can’t just, this isn’t...”
Madison, sitting close to Kylie, leaned over and whispered with a teasing grin, “Kylie, trust me... Justin is amazing. You’re going to love it. Every second.”
Kylie’s eyes sparkled with a mixture of excitement and determination. She glanced at Timothée, her tone leaving no room for debate. “You can go home, Timothée. Or... you can come with us and watch. But this is happening, one way or another.”
Timothée’s face turned red with anger, his fists tightening. “I... I can’t believe this. You’re seriously doing this? Right now?”
Kylie smirked, leaning back in her seat. “Yes. Right now. And yes, seriously. So either you deal with it, or you step aside.”
Justin, calm and collected, smirked, clearly enjoying the shift in power, while Madison whispered again, softly and enticingly, “Seriously, Kylie... you’re going to love every second of this. Trust me. Justin knows exactly what he’s doing.”
Timothée slammed his hand on the armrest, glaring at the two women. “This is ridiculous. I can’t believe you’re actually...”
Kylie interrupted with a firm shake of her head. “No arguments. I’ve made my choice. You’re either part of the night in the way I said, or you’re gone. Deal with it.”
Madison squeezed Kylie’s hand, still grinning. “See? You’re going to have an amazing time. I promise.”
Timothée sat back, fuming, his pride wounded, his anger palpable. He was not happy. Not even a little. But Kylie’s confidence, and Madison’s teasing assurance, made it clear that his feelings didn’t matter tonight. The bet was happening, and the night had already shifted irrevocably.
A short while later, back at Madison’s place, it didn’t take long, as Timothée sat in a nearby chair, watching as his girlfriend Kylie kneeled on the floor, next to the equally stunning Madison Beer, as the two women worked over Justin his shaft. Justin watched them both from above, almost too stunned to process the symmetry, Madison’s lips on his shaft, the familiar warmth of her mouth, and then Kylie, nervous, hungry, almost competitive, working in tandem to swallow him deeper.
The thick base of Justin’s cock brushed Kylie’s chin as she licked and sucked, the gloss on her mouth smeared and tacky. Madison flicked her tongue around the tip, careful to catch the bead of pre-cum before it could slide down his length. They bunched their shoulders together, cheek to cheek, the two of them so close. They traded him back and forth, occasionally glancing up at Justin as if seeing who could get a better reaction.
Kylie surprised him by squeezing the root hard with one hand, twisting as she bobbed her head. He groaned, and she gave a tiny smirk, eyes slitted and wet, not just from gagging, but with something almost devious. Timothée was watching, his gaze locked on Kylie’s lips as if he could will her to stop or to notice him. But she didn’t look, not even once.
Madison, with a wicked smile, pushed her tongue flat against the underside of Justin’s cock, she shot a wink at Kylie, who, catching the challenge, pressed her lips lower, forcing herself past her own reflex. Justin’s hand drifted to the crown of Kylie’s head almost absently, the gentle encouragement more command than comfort. He could feel her shoulders tense and then relax beneath his palm, each bob of her head more assured than the last.
The heady scent of sex and perfume mingled in the air, familiar, nostalgic, almost narcotic. The ambient music faded, replaced by the wet, explicit sounds of the women working together, the gasp of Madison’s giggle, the sharp inhale from Kylie as she found her breathing rhythm. Madison, ever the instigator, drew back and nibbled gently at Justin’s hip, leaving a mark before she turned to meet Kylie’s eyes, their faces so close, hair tangled together.
“Good?” Madison’s whisper, pitched just for Kylie, reached Justin’s ears.
Kylie didn’t answer. She just angled her neck and redoubled her effort, lips tight, eyes looking up to Justin for his reaction.
Before he could say anything, Madison shifted, and caught Kylie’s jaw in her hand, turning her for a kiss. It was sharp at first, a show put on for the room, but as Kylie parted her lips, Madison softened, pushing their faces closer, wet mouth on wet mouth. Justin could feel the heat burning off them, their unified focus bending the air.
Madison tasted Kylie for a moment, tongue darting, gloss and saliva exchanged, then released her with the same suddenness, an electric pop of movement. Kylie blinked, oxygen flooding her lungs, and then dipped back down on Justin with a hunger that felt upgraded, competitive and possessive both.
Justin watched, spellbound, as Madison took his cock in her fist and pressed the head to Kylie’s lips, almost feeding her, slow and deliberate. Kylie wrapped her mouth around the tip and let it glide in, this time owning the movement, her ego animated by the kiss and the gaze of the room. Madison hovered beside her, hand anchoring the base, her other fingers carding through Kylie’s hair. Two sets of dark lashes blinking up at him, two impossible faces within a fingertip’s reach.
"Alright, you’ve proved your point," Timothée murmured.
Kylie looked over at Timothée, and smirked at him. “Stop?” Her voice dipped. "Oh, babe, this is just the start."
Madison nudged her, lips at Kylie’s ear, barely a whisper, “Show him how much you like it.” Kylie nodded.
Kylie bent back in, her lips grazing against Madison’s in featherlight transit before they both locked onto Justin anew, Kylie’s tongue tracing the ridge where the shaft thickened, Madison lapping at the base, their cheeks pressed together, neither ceding ground. Madison spat in her hand, palmed a glossy coat along the entire length, then bared a feral grin and buried her tongue under Justin’s nut sack, intentional and unflinching.
Kylie’s lips sealed around the head again, but there was a new urgency, a drive that was more than just show for Timothée. She didn’t hesitate. She pushed down, letting Justin’s cock spread her open until it nudged the back of her throat, her nose pressed to Madison’s wrist clutching the base. A moment’s gag, then she steadied, holding herself there,
Justin bit the inside of his cheek, focusing on the sight of the two of them working together. The heat of Kylie’s tongue, the velvet slip of her mouth as she dropped down, then the scratch and gentle graze of Madison’s teeth skimming his balls. Madison’s hands never stopped, guiding, pressing, urging more.
Madison’s boyfriend focused on Kylie’s lips stretching around him. Madison’s hand braced at the base, a ring of pale knuckles, and Kylie’s lip gloss started to feather, the slickness overtaken by heat and friction. You could almost mistake it for a competition, except the pace had synced up, Madison using her hand, Kylie trading deep, insistent pulls. She wasn’t careful, not anymore. She wanted to make an impression, leave a mark, prove something to Timothée and herself at once.
Justin gripped the edge of the bed. Madison shot him a sidelong look, then mashed her cheek to Kylie’s so close he could see their lashes tangle, the tip of his cock bulging between their mouths. Madison whispered encouragement, voice so low it was barely a sound, just a brush of breath against her ear. She snaked an arm around Kylie’s waist, offering leverage, pulling her closer each time she slipped forward.
Kylie braced to swallow again, but Madison’s hand wrapped hers, tugged her head back gently. She spat over the head of Justin’s cock, then kissed Kylie, just the lips first, then deep, sharing the taste. Kylie let her.
They scrambled up, side by side, a thrum running through both women. Justin watched their bodies slide across the bedspread. Kylie’s skin looked impossibly smooth, as she planted herself face down on the comforter, arching almost instinctively. Madison mirrored her, ass-up, bare thighs flexing as she braced her elbows.
Justin’s hands tingled with anticipation. He trailed behind, eyes drinking the symmetry of their bodies, the tight press of hips and thighs, dip of waist, the way their heads turned, hair spilled and tangled, cheek to cheek, waiting for the first move.
“Are you just going to look at us or...” Kylie started to say.
Madison finished for her, breathless, “He likes building up the suspense.”
Justin liked the way anticipation could change a room. It stretched the air, made the ceiling feel lower, the bed wider, the bodies warmer. He ran a hand down Kylie’s back, tracing the arch of her spine with his palm. Kylie tensed, her skin goosebumping under his touch, and he wondered if she’d flinch away or lean into it. She leaned in.
He planted a knee on the bed, flanked by the two of them, Kylie to his right, hair veiling her cheek as she peeked up at him; Madison to the left, lips wet, parted, a faint line of saliva at the corner where she’d bitten down on the inside.
Justin pressed down, hand flat between Kylie’s shoulder blades, urging her to the mattress, and she went, face sideways, arms up, fingers burrowing into the surface. He thought he heard Timothée shift in the chair but Justin didn’t look up.
Justin gripped Kylie’s ass hard enough she’d remember it. He slid two fingers along her slit, a trickle of anticipation, and spread her open. Madison, next to her, angled her hips wider, offering him a parallel view, and went up on her elbows, tilting her chin to watch. Justin guided the head of his cock toward Kylie’s opening, let it rest a second, a weight and a promise, then pressed in.
Kylie’s thigh jumped. No whimper or anything, just a deep breath, head turned so he could see the flush against her jaw as she exhaled. Justin fed his cock in a little more, and a little more, until he bottomed out, hips flush up against her ass. The grip of her was different, tighter, more hesitant maybe, but eager. He rolled his hips, slow, then faster, until the bed started to squeak. Madison’s face hovered inches from Kylie’s, hair falling in a brown-black curtain between them. Madison licked her lips, scooted closer, and brought her mouth to Kylie's shoulder, biting gently.
Kylie’s knees dug deep grooves in the comforter as Justin pistoned into her, the slap of skin forming a beat she couldn’t sync her breath to. She let it override thought, scoured her mind with sensation, let the ache build. Madison’s hand was on the small of her back, thumb stroking gentle circles as if she was, absurdly, comforting Kylie through what was unmistakably mutual pleasure. They were aligned, barely inches apart, Madison’s quickened breath cooling her ear, their hands linked at the edge of the bed.
Justin reached around and cupped Kylie’s hip, pulling her up to him with hard, deliberate thrusts. His other palm pressed between her shoulder blades, anchoring her so she arched against every movement. Maybe that was what Timothée saw, though she couldn’t see him directly. That thrill, the performance of it, only made her want to fold herself further, to see what lines she could cross.
He drove the rhythm harder, Kylie's ass cushioning every collision of his hips. Sweat slicked the small of her back. Justin could feel her body easing open, friction relaxing into frictionless glide, so each new thrust went deeper, the slap louder, then wet and soft and barely muffled by her flesh. Kylie muttered something into the pillow, knocked her head against it, and grabbed at the comforter like she was holding tight to consciousness itself.
Madison hovered, always close, mouth grazing Kylie's shoulder, then her cheek, then lower along her side. The weight of Madison's hand followed the dip of Kylie's waist, dragged as slow as molasses over her hip, then trailed between Madison's own thighs. Justin watched in the periphery as Madison's fingers slipped into herself, the shine already there, never hesitating, her knuckles bumping the covers as she matched his tempo.
Madison moaned, just a shiver of sound, and pressed her face behind Kylie's ear. "God, you look so good like that."
Sound spiked every time Justin’s hips connected with Kylie's, the slap blunt and filthy, louder than the headboard’s shuffle. She shot a look at the closet mirror, caught the kaleidoscope of bodies and sweat and tangled hair, caught Madison’s mouth open, tongue wetting her lower lip, yeah, she was working herself, fast. That thought alone made Kylie’s own breath warp and stutter.
Justin didn’t slow, just fucked her into the mattress, steady and sure. Kylie didn’t care if the whole house heard, didn’t care if Timothée caught every second. Let him. She let her voice go, a full-throated moan that wasn’t planned or dramatic, just a thing that ripped out of her as she came. Her insides clenched hard around Justin, and he braced himself, muscles going taut, hands squeezing her hips like he’d never let go.
Madison, breath coming in little cuts, worked her hand between her thighs with a speed that blurred fingers. She pressed her lips into the crook of Kylie’s shoulder, half-kissing, half-biting, and used her other hand to leash Kylie’s waist, holding them together. Their sweat and perfume mixed, something sickly-sweet and salty.
Madison pressed her hand hard to her sex mound, grinding in circles before she slipped two fingers back inside, curling them upward. Her sounds grew sharper, wetter, and every time she jerked her hand in tempo with Justin’s thrusts, the slap of her palm echoed.
She watched Kylie, watched the cascade of ass and arch and flesh, saw the tension roll up Kylie's back in a slow shudder, saw how Kylie’s cheek mashed flat against the covers, mouth open in a devilish smile.
Justin fucked Kylie for what felt like forever. He held her hips up like a trophy, his own jaw set, biceps flexing with every pull. The tempo went from punishing to cruel, then back again, never relenting. Sweat dripped off his chin and spattered the dim-lit skin below. At some point Madison let her knees slip, sinking to the bed so both of them lay side by side, torsos pressed flat, their hair snaking together over their shoulders and down the bedspread.
Justin wanted Madison next. He didn’t ask, he pulled out of Kylie and let her collapse, chest heaving, breath wild and lost, then grabbed Madison’s waist and dragged her up and back, repositioning her with a grip that left no room for debate. He lined up and slid into her, fast, one smooth push, it made her cry out, full-bodied and instant, no decorum now, none of that practiced porn-kitten noise. Just raw, a slap of pressure and want.
Madison was already so close, he knew her well enough to read it in the way her spine arched, in how her knees nearly left the bed from the force of impact, in how both hands splayed flat on the sheets like she needed to claw herself back down to earth. He fucked her hard, didn’t bother with any carefulness, and her body met him, threw itself onto him with each thrust instead of away from it.
Kylie rolled to her side, hair in her mouth, mascara melted to a raccoon blur, eyes wide but lazy in that post-climax lull. She didn’t say anything. Barely blinked. She watched Justin’s hips piston against Madison, and watched the way Madison took it all.
Madison’s moans rose sharp, then softened into little yips, and Justin’s hand drew hard lines on her waist, smearing the sweat where it bucked out around her hips. Kylie watched the way Madison’s ass bounced, the way the pure force of the thrusts rippled muscle and skin in a split-second wave. Each snap of impact seemed to echo off the walls, the only punctuation to the wet percussion of flesh.
Timothée’s breath rattled, harsh and uneven. Kylie rolled her head on the pillow to catch him in the edge of her vision. He was rigid in the armchair, elbows clamped to the sides, thighs tensed under the sweats. His face, a twisted scowl of loss and something else. Not just rage at being made a spectator, something more feral in the darkness behind his eyes.
Justin never eased up, not for a second. His tempo on Madison bordered reckless, every slam of his hips loud, merciless, a concrete pace that grated the bed legs against the floor. He knew exactly how to angle, how to chase her sounds, if he stroked outward in a slow grind it made her whimper, but if he jackhammered her with fast, shallow thrusts, she moaned, caught off guard by the shock of it. He layered them, a sadist at the metronome, and Madison went wild for it.
Madison egged him on, cursing under her breath, digging her nails through the comforter, bunching it in tight fists. Her noises hit the entire spectrum, low and thick with desperation, then unexpectedly bright and girlish, like something was surprising her again and again each time. She kept her face down, now more like she was hiding from the force than from embarrassment, and when he pistoned into her hard enough, her knees slipped, and she almost bellyflopped into the mattress, only to push up again reflexively, palms flat, one elbow buckling with every impact.
Madison went up on her elbows, fingers twisting into the sheets. Justin fucked her like he was trying to brand every inch of her, then faster. From the side, Kylie watched wide-eyed, almost hallucinating the connection between the wanton action of it and the way Madison’s hips didn’t shy from the collision. It was like Madison wanted every bruise, every echo, like she needed to be split open and put back together all in the same instant.
She howled then. The noise drilled through Kylie’s head, the kind of sound that you heard once and it lived in your nerves forever after. Justin caught her hips and held them up, forcing her to take the full length, again and again, grinding her down into the bed until the springs bit back. Madison shook as the orgasm hit, every muscle in her legs trembling.
Madison didn’t collapse, didn’t quit. Instead, after the ripple subsided. he twisted so she was flat on her back, legs splayed, and yanked Justin on top of her with both hands. She dug her heels into the mattress, locked her knees at his sides, and pulled him into her herself, using her entire body to ride him like she was wringing every last sensation out of him.
From the edge of the bed, Kylie watched, dazed, still catching her own breath. Sweat prickled her skin. Her thighs were sticky, the afterglow lingering. She traced the ridges of her own hip, fingers still tingling. She had never seen Madison like this.
Justin hammered into Madison, with two, maybe three more bone-rattling thrusts. Madison’s mouth shaped a silent fuck, her head thrown back. He knew when it was time. He slid out of Madison in a slick, indecent withdrawal, her legs still quivering. Madison lay there breathless, before she rolled to the edge of the bed, grabbing Kylie by the wrist, pulling her up next to her.
“Kylie, here. He wants to see you, too,” Madison whispered, grinning sideways through a mask of sweat and smeared gloss.
Justin stood at the edge of the bed, knuckles bleached against his cock. Madison sprawled deliciously on her back, her breath jagged. Kylie, hair wild, lips parted, was yanked up by Madison and fell forward, catching herself on an elbow, cheeks flushed and eyes huge, she was maybe half in control, half in shock at how much she’d wanted this.
He couldn’t stop staring at the two of them together. Madison reached for Kylie, slow and calculated, running her fingers from Kylie's shoulder down to her chest, as if arranging her for the finish. The way their skin looked together, slicked by sweat.
The room pulsated. Even the shadows felt like they were watching. Timothée’s breathing was a hard, angry drag at the side of the room, like a vacuum gorging on someone else’s pleasure.
Justin braced his palm against the headboard and stroked himself with two quick, decisive passes. He was so close now he felt weightless. All the air in his body funneled toward the top of his head.
His hand tightened on his cock, and he felt every cell in his body tighten with it, up and down, one, two, Kylie locked eyes with him, her pupils blown and feral, lips parted. He aimed for her face. It’d be a lie to say he did it for Timothée, or even for Madison. It was for the look on Kylie’s lips the instant the first warm gooey spunk hit, her mouth opened, tongue out, a perfect, greedy target.
Justin’s body jerked again, semen spattered across Madison’s cheek, then over her neck and collarbone, a messy, decadent line. Kylie twitched as the next jet caught her in the chin, the warmth of it in strong, unmistakable ropes. Kylie’s smile widened, as if she’d been crowned right there on the ruined bedspread.
“You did good,” Madison whispered.
Kylie licked her lips, tasted Justin, tasted herself, tasted the gooey saltiness of the night. She’d been scared, just a little, but now that fear had been replaced by something else, pride maybe, maybe just the giddy triumph of having rewritten her own rulebook. She wiped a smear of cum from her chin, then, eye on Timothée, drew her fingertip between her lips.
“We uh, we should probably go,” Timothée said.
Kylie scoffed, the sound flat and dry as a smack to the face.
“You’re not serious.” Madison stepped closer, still topless, hair falling over her upturned breasts. She seemed unashamed, as if nudity were just another filter she could toggle on or off.
The End
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This was great. I really loved how descriptive you got. It was sexy without sounding gross. This is how it's done.
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Thanks Blocboy.
I appreciate the comment, it really means a lot to me. Both Kylie and Madison are two of my favorites, so it was great to pair them up.