Alex’s Losing Streak

"When a string of bad poker hands forces Alex into his sister’s slutty cheer costume, playful teasing quickly turns into a night of humiliating submission and unexpected desire."

Font Size

The four friends—Sam, Jake, Mike, and Alex—were hanging out in Alex’s basement on a lazy summer afternoon, the kind where boredom settles in thick and turns harmless games into something sharper. They were all eighteen, freshly out of high school, friends since middle school. The room smelled of cold pizza crusts and the faint metallic tang of energy drinks. A thick beige carpet covered most of the floor, muffling footsteps and making the space feel a little less raw than the exposed concrete edges suggested. The television sat silent with a paused game frozen on the screen. They had been playing poker for hours, the bets starting small—who buys the next round of snacks, who has to clean up the mess—but the mood had shifted, the air growing heavier with every hand.

Sam, the group’s resident jokester, dealt the next round with a wide grin. “Alright, losers, ante up. Winner calls the shot on the biggest loser. Something humiliating this time.” The others laughed, but Alex—who had been bleeding chips all afternoon—rolled his eyes. “I’m already tapped. What’s the damage?”

A few hands later, Alex folded with a groan. “Dammit. Out again.” Jake, the broad-shouldered jock who naturally took the lead in every situation, slapped the table and laughed loudly. “That’s it, Alex. You’re the big loser tonight. Time to pay up.” Mike, quieter and more observant, leaned forward with a slow smirk. “Remember the Halloween thing last year? When you wore your sister’s cheerleader outfit? The slutty one? Yeah. Put it on.”

Alex’s face flushed crimson. “No way. That was a joke. One time.” But the others piled on, chanting and teasing until the pressure became impossible to ignore. “Fine,” he muttered. “This stays in this room. Forever.” He trudged upstairs to his sister’s bedroom—she was away at college—and rummaged through her closet until he found it: the short pleated skirt in white with bold blue and red trim, the cropped sleeveless top with the big “H” across the chest and matching chevron stripes, and the pair of strappy white heels he had practiced walking in for that Halloween party so he wouldn’t look ridiculous. Tucked inside the top drawer were the silicone breast inserts she’d bought for the costume—soft, realistic-looking pads that gave the outfit its full cheerleader shape. He hesitated, then slipped them in anyway. The longer hair he’d been growing out since junior year fell across his shoulders as he adjusted the top; the guys had teased him mercilessly about it for months, calling him “pretty boy” and “rockstar wannabe,” but tonight it felt like part of the disguise.

When he appeared at the bottom of the stairs, the room erupted. Alex tugged uselessly at the hem of the skirt—it barely reached mid-thigh. The cropped top hugged his torso, the silicone inserts creating two soft, convincing bulges that pushed against the fabric. His longer brown hair framed his face, brushing his collarbones. He wobbled slightly in the heels, cheeks burning under their stares and laughter.

Jake was the first to zero in. “Holy shit, Alex—look at that chest! You actually stuffed the girls in there?” He pointed, grinning wide. “Those look real from here. You practicing for the cheer squad now?”

Sam laughed so hard he nearly spilled his drink. “Dude, with that hair and those tits, you’re halfway to being your sister. We’ve been telling you the hair was too pretty—now it’s perfect.”

Mike smirked. “Yeah, Lexi’s got curves tonight. Nice work.”

Alex’s face burned hotter. “Shut up. It’s just the inserts.” But the teasing only made the outfit feel more real, more exposing. He felt every sway of the skirt, every shift of the silicone against his chest, every brush of his own hair against his neck.

Jake leaned forward, eyes gleaming. “Damn, Lexi, you actually look good. But hold on…” He tilted his head, then burst out laughing again. “I can see your boxers right through the skirt. That’s cheating. If you’re doing this, do it right. Go back up and grab some of her panties. Full commitment.”

Alex’s stomach dropped. “You’re kidding. That’s too much.” Mike shrugged. “It’s just us. Don’t chicken out now. Bet’s a bet.” Sam winked. “Come on, man. Legendary story. Go.”

The gentle but relentless push was enough. Alex sighed and climbed the stairs again. In his sister’s room, he hesitated at the dresser. Most of her things were packed for college, but the top drawer still held a few forgotten pieces. He pulled it open, and a faint, sweet-feminine scent drifted up—lavender laundry soap mixed with something warmer, more intimate. His fingers brushed over stray bras and plain cotton underwear before he found it tucked in the back: a red satin thong, thin straps, glossy front panel. The fabric felt cool and slippery against his skin. Holding it made his pulse jump in a way he didn’t want to examine.

He slid his boxers off and stepped into the thong. The straps glided up his legs like cool silk. The satin settled snug against his balls, then tighter as he adjusted himself, the material pressing his cock and everything else into place with a smooth, insistent friction. He tugged the back strap higher; it nestled between his cheeks. A quick shift to make sure nothing pinched. The sensation was humiliating—and strangely thrilling.

When he returned downstairs, the room went quiet for a heartbeat, then exploded again. “Proof!” Jake demanded, voice playful but commanding. Alex’s face burned hotter. He lifted the skirt just enough to show the red satin, the faint outline of his growing arousal visible beneath it. The silicone chest pushed forward with the motion, drawing fresh whistles.

Sam pointed. “Look at those tits bounce when he moves. You’re killing it, Lexi.”

Jake nodded approvingly. “Yeah, full package now. Hair, chest, thong—the whole slutty cheerleader vibe.”

The basement air felt thicker now, charged. Alex stood in the center of the room, thong hidden under the short skirt, cropped top riding up whenever he moved, silicone breasts giving him an unmistakably feminine silhouette. His longer hair fell forward as he ducked his head, arms crossed tight across his chest as if that could hide the bulges. The heels made escape impossible. The guys passed fresh sodas around, still chuckling, eyes flicking back to him—teasing, waiting.

Jake shuffled the deck with exaggerated care. “One more hand. Same rules. Loser does whatever the winner wants. Lexi’s already halfway there—let’s see how far he goes.” He dealt the cards, smirking like he already knew the ending.

Alex sat gingerly on the edge of the couch, knees pressed together to keep the skirt from riding up too far. His heart thudded so hard he could feel it in his throat. He lost—badly—within three rounds. Mike flipped his winning cards with a quiet smile. “You again, Alex.”

A brief silence settled. Then Sam leaned forward. “Mike gets to decide. What’s the punishment?”

Mike studied Alex for a long moment. “Lap dance. But not to me. To the guy with the second-worst hand. That’s you, Sam.”

Sam blinked, then gave a nervous laugh. “Wait—me?”

Alex’s mouth went dry. “Guys, come on. That’s—”

“Bet’s a bet,” Jake said, tone light but unyielding. “Thong’s already on. No backing out now.”

Mike nodded. “Just us. Five minutes. Keep it fun. Sam, sit.”

Alex looked from face to face—Jake’s expectant grin, Mike’s calm encouragement, Sam’s wide-eyed surprise. He swallowed hard and gave the smallest nod. The submissive pull was too strong to fight. “Okay. Fine.”

Sam scooted back on the couch, legs spread casually, arms draped along the backrest, trying to look relaxed even as color crept up his neck. Alex rose on unsteady heels, the skirt brushing his thighs with every step, his longer hair swaying slightly with the motion. He moved between Sam’s knees, face flaming. Someone turned the phone music louder—slow, heavy bass that vibrated through the carpet.

He started awkwardly, hips swaying side to side, hands hovering before settling on Sam’s shoulders for balance. The skirt rode higher with each movement, showing more thigh. His hair fell forward, brushing his cheeks as he turned slowly, then lowered himself until his ass brushed Sam’s lap. The first grind was hesitant, barely contact, but he felt it instantly—the thick, growing hardness pressing up through Sam’s shorts, hot against the thin satin of the thong.

Alex froze for half a second, breath catching. He could feel the shape clearly now, insistent and real. His own cock twitched in response, the satin suddenly far too tight. He kept moving, rolling his hips in small, uncertain circles, pressing down harder because the others were watching and he refused to look weak.

Sam’s hands settled on Alex’s waist, fingers resting lightly on bare skin just above the skirt’s waistband—not grabbing, just guiding the rhythm a little. Alex’s pulse spiked at the touch. He leaned back slightly, grinding firmer, feeling the bulge throb beneath him. His own erection was impossible to hide now; the front of the thong tented visibly whenever he shifted. The silicone breasts shifted with the motion, drawing another low whistle from Jake.

Sam noticed first. His eyes dropped. “Uh… Lexi. You’re really hard right now.”

Alex’s face burned hotter. He tried to pull back. “Shut up, I’m not—” But another shift made Sam’s cock jump harder against him. “Wait—you’re hard too. Look at that.”

The room exploded. Jake pointed, laughing. “Sam’s rock solid from Lexi’s lap dance!”

Mike smirked. “Pretty obvious, man. Lexi’s got you going.”

Sam shook his head, flushed. “It’s just friction or whatever. I’m not into it like that.”

Jake’s grin widened. “Oh yeah? Prove it. If you’re not turned on, Lexi won’t be able to make you cum. Simple test.”

Sam hesitated, glancing down at Alex still hovering over his lap, long hair framing his flushed face. “How the hell does that work?”

Mike shrugged. “Let him try. Hand, mouth, whatever. If you’re really not feeling it, nothing happens. Easy way to shut everybody up.”

The room fell quiet except for the steady thump of bass. Alex’s breath came short and shallow. He looked down—Sam’s shorts were unmistakably tented, the outline thick and clear. The others leaned in, eyes bright with anticipation. A strange rush swept through Alex—embarrassment, yes, but also something hotter, more compelling. If he could make Sam cum, it would prove Sam was the one turned on, not him. It was dumb logic, but in the haze of heat and pressure it made perfect sense.

“Fine,” Alex muttered, barely recognizing his own voice. “Let’s see.”

Jake let out a whoop. “That’s my boy, Lexi! Show us what you’ve got.”

Alex slid off Sam’s lap and knelt between his legs. The skirt pooled around his thighs; the heels dug into the carpet. His long hair fell forward as he leaned in, brushing his cheeks. His hands trembled as he reached for the waistband of Sam’s shorts. He tugged them down slowly, revealing the straining bulge in the boxers beneath. Sam lifted his hips to help, breath already quicker, face caught between denial and curiosity. Alex hooked his fingers into the boxers next and pulled them down. Sam’s cock sprang free—thick and veined, the head flushed deep pink, a bead of pre-cum already glistening at the tip.

Alex stared, transfixed. His own cock throbbed painfully inside the thong. This was real—hot, pulsing flesh inches from his face. The musky male scent hit him and made his head swim. He wrapped his fingers around the base tentatively, feeling the heat seep through his palm, the velvety skin sliding over rigid hardness beneath. It jumped in his grip. He stroked slowly, up and down, savoring the way it thickened under his touch. The slight curve, the way the veins stood out, the smooth glide—it was all so new, so overwhelming. Dressed like this, in his sister’s slutty cheer outfit with the thong hugging him like a secret and the silicone breasts shifting slightly with every breath, he felt exposed, feminized, slutty. Like he belonged on his knees, pleasing.

“Yeah, Lexi, grip it tighter,” Jake said from the side, voice low and rough. “Stroke it like you mean it. Make him feel every inch.”

Mike leaned closer. “Look at you. Already hooked. Bet that thong is soaked. You love being our little cheerleader slut, don’t you?”

Alex’s cheeks burned, but he didn’t stop. He thumbed the slit, spreading the pre-cum in slow circles until the head glistened. Sam groaned, hips twitching. Alex leaned in and dragged his tongue along the underside, a long, deliberate lick from base to tip, tasting the salty tang, tracing every ridge. His hair fell across his face again; he tucked it behind one ear without thinking. Sam’s hand settled lightly in Alex’s hair. “Fuck… yeah. Just like that.”

Alex wrapped his lips around the head, sucking gently at first, tongue swirling in lazy circles. The stretch of his jaw, the weight on his tongue—it filled him, made him feel used in the best possible way. He bobbed slowly, taking more with each pass, his free hand cupping Sam’s balls, rolling them gently, feeling their warmth and heaviness. The sensations built inside him too—the satin rubbing against his leaking cock with every small shift, the skirt brushing his thighs like a constant tease, the silicone chest rising and falling with his quickening breaths. He felt like he was slipping into a role he hadn’t known he wanted: submissive, eager, slutty. This thickness is stretching my mouth already, he thought. Tastes salty-sweet, not what I expected. Makes me feel so small, so submissive.

“Deeper,” Sam panted, fingers tightening in Alex’s hair, brushing strands away from his face. “Take more. Show me how much you want it.”

Jake laughed softly. “Hear him moan around it? He’s practically purring. Keep going, slut—make him beg.”

Alex moaned around the cock; the vibration made Sam hiss. He took Sam deeper, gagging softly when it hit the back of his throat but pushing through, cheeks hollowing, sucking with slow, deliberate pulls. His own arousal was unbearable—the thong’s friction, the taste flooding his mouth, the humiliation of being watched while dressed like this, long hair swaying with every bob of his head. His body tensed suddenly; a muffled whimper escaped as he came hard in the satin panties, hot spurts soaking the fabric, his cock pulsing in waves against the smooth material. He paused for a heartbeat, shuddering, but didn’t stop sucking, riding out the aftershocks while keeping his lips sealed tight. I just came from this… from sucking my first cock. What the hell am I?

Sam noticed immediately, voice rough. “Holy shit… did you just cum? From sucking me?”

Jake’s eyes widened, delighted. “He fucking did! Moaned like a little bitch and everything. Look at him shaking—hair all in his face.”

Mike smirked. “Don’t stop now, Lexi. Finish what you started. Prove you’re a real cumslut.”

Alex pulled back just enough to gasp for air, lips shiny, long hair clinging slightly to his damp forehead, then dove back in, sucking harder, faster, tongue flicking the sensitive underside. Sam’s breathing turned ragged, hips rocking shallowly. “Fuck—close… so close…” But he held on, drawing it out, making Alex work for it longer—slow bobs turning into deeper, wetter ones, hand stroking what his mouth couldn’t reach. Minutes stretched; the room filled with slick sounds and heavy breathing.

Finally, Sam tensed, fingers gripping Alex’s hair. “Gonna—!” He came with a long groan, flooding Alex’s mouth with thick, bitter spurts—not an overwhelming amount, but sharp and salty, the taste clinging to the back of his throat. Alex swallowed most of it; a little dribbled down his chin as he pulled off, panting, dazed. That cum… warm, not too much, but it hits and stays. Makes me feel dirty. Used.

The guys clapped slowly. Jake pointed at the skirt. “Stand up, Lexi. Show us the mess you made in those panties.”

Flushed and spent, Alex rose on wobbly heels and lifted the skirt. The red satin thong was soaked, dark patches spreading where his own cum had seeped through. The silicone breasts still sat high and proud under the cropped top.

Sam whistled. “Damn, even after all that, the tits are still perfect. You’re committed, Lexi.”

Mike grinned. “He loved being our little cumslut way too much. Guess that means we’re next—no excuses.”

Alex nodded weakly, the submissive thrill still humming through him. He moved to Mike next. Mike was already shoving his shorts down. His cock was shorter than Sam’s but noticeably thicker, the girth promising to stretch Alex’s mouth from the first inch. Alex knelt again; the wet thong clung uncomfortably now, but it only deepened the slutty feeling—like he was marked, ready for more. His long hair fell forward as he leaned in, brushing his cheeks. He stroked the thick shaft slowly, thumb tracing the prominent veins, feeling how completely it filled his hand with every slow pump. This one’s wider, heavier, he thought. Veins like ropes. My jaw’s going to ache just thinking about it.

“Look at you,” Sam said, voice teasing now that he had recovered. “You’re loving this. Our cheerleader slut, already covered in cum and still going.”

Jake nodded. “Suck him good. Show us how much you want every drop. Be a good girl.”

Alex hollowed his cheeks and took Mike deep, nose eventually brushing pubes as he held there, throat working. The fullness made his jaw ache in the best way; the taste was muskier, earthier than Sam’s. Submission crashed over him in waves—he was doing this for them, on his knees in a skirt, his own cum still sticky in his panties, silicone chest rising with each breath. It felt sluttier with every passing second. Mike’s hand rested heavily in his hair, fingers occasionally brushing strands away from his face. “Deeper… yeah, just like that… perfect.” He drew it out too, rocking gently, making Alex earn every inch with long, slow sucks and teasing licks until Mike finally groaned low and spilled—thicker and heavier than Sam’s load, flooding Alex’s mouth fuller, creamier texture that coated his tongue and lingered longer. Swallowing it made him feel owned, like he was truly their toy now.

Last was Jake—the one who had pushed every step, the natural alpha. His cock was the biggest by far: long, thick, a monster with bulging veins and a massive, flared head. Alex stared, a spent twitch stirring in his thong at the sight. “Take your time, Lexi,” Jake said, voice low and commanding, the nickname landing like a spark.

Alex jolted. Lexi. Hearing the girl’s name while dressed like this, on his knees, sent a shiver racing down his spine. It felt so slutty, so submissive, so right. Like he really was Lexi now—the eager little cheerleader in the short skirt and heels, thong ruined with his own cum, silicone breasts shifting with every quick breath, long hair framing his flushed face, ready to worship. His heart hammered; the thrill sank deep into his bones.

“Yeah, Lexi,” Jake continued, grin wicked. “Just like those porn videos you’ve seen. The sluts know how to worship a cock properly. Touch it. Explore it slowly.”

Lexi’s fingers traced the length reverently, feeling the impossible girth, the way the veins throbbed under his touch. He kissed the tip softly, then trailed slow pecks down the shaft, finally reaching the heavy balls. He nuzzled them, pressing soft kisses to the warm skin, inhaling the stronger, tangier musk. This monster is so long I can barely wrap my hand around it, he thought. Tastes sharper, almost tangy. The balls are so full—heavy. Kissing them makes me feel even smaller, more devoted.

“Good girl,” Jake murmured. “Kiss those balls. Yeah. Lick them slow.”

Lexi obeyed, tongue lapping gently, sucking one lightly into his mouth, then the other. Jake groaned in approval. He worked his way back up, licking the full length in long, flat strokes, swirling around the head. His long hair fell across his face again; Jake reached down and tucked a strand behind his ear with surprising gentleness before gripping the back of his head. Lexi took Jake in slowly, inch by inch, jaw stretching wide. He bobbed with deliberate care, tongue working the underside the whole time. It’s hitting so deep, filling me completely. Submission is crashing over me—I’m such a slut for this, loving every thick inch.

“Fuck, Lexi,” Jake panted. “Deeper. Worship it.”

Minutes stretched as Lexi savored every sensation—hands massaging Jake’s balls, throat relaxing to take more. Jake’s grip on his head grew firmer; he pumped slowly at first, then faster. “Gonna fill you up…” He tensed, thrust deep, and came—hot ropes pumping straight down Lexi’s throat. The biggest load yet, endless thick spurts, saltier and more intense than the others, overwhelming his mouth until he nearly choked, but swallowed every drop. The taste lingered like a brand. Jake held him there until he was finished, only then letting him pull back with a gasping breath, feeling utterly broken in, a complete cumslut.

When it was over, Lexi sat back on his heels, lips swollen, chin shiny, the mingled tastes of all three still coating his tongue, thong a sticky ruin. His long hair clung slightly to his damp skin; the silicone breasts rose and fell with his heavy breathing. The guys zipped up, laughing it off like it was just another wild afternoon.

“Epic, Lexi,” Jake said, already reaching for the deck to deal another hand. “But you’re staying dressed—you look way too good like that. Go grab us some drinks. Be a good girl and serve.”

Lexi stood, skirt swishing against his thighs, heels sinking slightly into the carpet as he headed for the stairs. Jake’s hand swung out and landed a sharp smack on his ass—the sting made him yelp, but it sent a fresh wave of submissive heat rolling through him. Behind him, the cards were shuffled, and the game started up again, but the air still thrummed with everything that had happened—and the unspoken promise that it wasn’t over yet.

Published 2 hours ago

Leave a Comment