Fantasy Football Bet

Mark’s cock sat soft and average in his boxers when the final scores locked in. Fantasy football had never felt this personal. Nine months of dating Talia, nine months of her laughing whenever he joked about bringing another girl into their bed, and now the league had decided the shape of that fantasy. If her team took the season, Mark would not simply watch her with another woman. He would be a second woman. The lesbian friend who had been circling Talia for years—Karma—liked trans girls too. That was the real prize. If he wins, they will find a willing bi chick online either way he gets the threesome he had teased ever since he learned Talia is bisexual and had several women partners.

Week one belonged to Talia.

She leaned against the kitchen counter the moment the app refreshed, red hair falling over one freckled shoulder, blue eyes bright with victory. “Panties only inside the apartment. Starting now. Strip.”

Mark’s face heated. He was twenty-seven, five-seven, one-fifty-seven, the kind of ordinary body that had never drawn second glances in a locker room. His soft cock measured a neat three and a third inches in both length and girth; hard it managed five and one-sixteenth by four and two-thirds. Average. Forgettable. Talia’s body was the opposite—five-four, thirty-six-inch legs, 32C tits that sat high and freckled on pale skin, 143 pounds of soft curves he usually got to bury himself in.

He peeled off his clothes while she watched. She handed him a pair of her own black cotton briefs, the ones that still held the faint scent of her cunt from the day before. The fabric was soft and slightly worn, the elastic waistband already stretched from her hips. When he stepped into them the cotton cupped his soft cock and balls into a smooth, rounded bulge, the front panel warm from her body heat and faintly musky. The back of the panties settled into the cleft of his ass, the seams pressing against the sensitive skin of his inner thighs. Nothing else. No shirt, no socks. Just panties. The cool air of the apartment kissed his bare chest and the backs of his knees; every step made the cotton shift and rub against the head of his cock.

Ten minutes later she had him pressed against the refrigerator. The stainless steel was cold against his shoulder blades. Talia dropped to her knees on the kitchen tile, the sound of her knees meeting the floor soft and deliberate. She leaned in and mouthed the front of the panties, breathing hot through the cotton until the thin fabric grew damp and translucent against the outline of his cock. Her freckled cheeks brushed the insides of his thighs. She licked along the ridge of his still-soft shaft through the cloth, the wet heat of her tongue soaking the cotton, the texture of the weave dragging against the sensitive skin of his glans. When she pulled the waistband down just far enough to free him, the elastic snapped lightly against his lower belly. His cock, half-hard and average, bobbed free, the head already shiny. She took him into her mouth with a greedy little sound, lips stretching around the four-and-two-thirds-inch girth, tongue pressing flat along the underside where the vein pulsed. The inside of her mouth was hot and slick, the soft palate brushing the head each time she took him deeper. One freckled hand rolled his balls, the skin there tight and warm, while the other slipped between her own legs, fingers working wetly. Mark’s hands fisted in her red hair; the strands were silky and slightly tangled from the day. She kept him trapped in her throat, swallowing around him so the muscles fluttered against the head, until the pressure in his balls tightened and he came with a choked groan. Thick pulses of cum flooded her mouth; she swallowed greedily, the contractions of her throat milking every drop, then licked the head clean with slow, deliberate strokes of her tongue, tasting salt and the faint residual musk of the panties. She tugged the waistband back up over his spent cock, the cotton now warm and sticky against his softening shaft.

“Leave them on,” she said, voice rough. “I want to feel them when you fuck me later.”

That night on the couch she straddled his lap still in her work blouse, no panties of her own. The living-room lamp cast a warm yellow light across her freckled thighs. She rubbed her bare, slick pussy along the cotton-covered ridge of his cock, the soft lips parting around the fabric, her wetness soaking through almost immediately. The heat of her cunt radiated through the thin cotton; each slow grind smeared her juices along the length of him until the front of the panties was dark and shiny and clung to every contour of his shaft and balls. The scent of her arousal rose between them—salt and skin and something faintly sweet. Only then did she reach down, pull the crotch aside with two fingers, and sink down. The head of his cock parted her folds and slid into the tight, velvet heat of her. She took him to the root in one smooth motion, the stretched cotton of the panties framing the base of his cock, the waistband digging into his hips. Her inner walls clenched and fluttered around the five-and-one-sixteenth inches, the wet drag of her cunt against him audible in the quiet room. Mark’s hands gripped her freckled ass, the soft flesh yielding under his fingers, the dimples at the top of her cheeks warm. She rode him with short, hard rolls of her hips, the blouse sliding up so her 32C tits swayed above him, freckles scattered across the pale curves, nipples tight and pink. Every downward stroke forced the panties tighter against his balls; every upward drag made the soaked cotton drag along the sensitive underside of his shaft. She came first, thighs trembling, cunt clamping down in rhythmic pulses that milked him, a broken moan spilling from her lips. She kept moving through the aftershocks until the pressure in his cock became unbearable and he spilled inside her with a broken sound, thick pulses of cum flooding her, the heat of it mixing with her own wetness and seeping back out around his shaft into the already-ruined panties. She climbed off slowly, the loss of her heat leaving his cock wet and cooling in the open air, then left the mess in the panties and made him wear them to bed. The cotton clung to him all night, stiffening as it dried, the scent of their mixed fluids rising every time he shifted.

The next morning in the shower the water was hot and the steam thick. Talia stepped in behind him, the spray plastering her red hair to her freckled shoulders and running in rivulets between her breasts. She soaped her hands and washed every inch of his body except the panties—palms sliding over his chest, down his stomach, around to the small of his back, the lather slick and fragrant. She left the black cotton on, soaked and clinging, the fabric turning translucent against his cock and the cleft of his ass. Her soapy fingers stroked him through the wet cotton, the weave of the fabric dragging over the head and along the shaft until he was hard and leaking, the pre-cum mixing with the water and soap to make the front of the panties slippery. Then she turned, braced her hands on the cool tile, and pushed her ass back. Water streamed down the long, freckled length of her thirty-six-inch legs and pooled at her feet. Mark yanked the crotch of the panties aside; the elastic bit into his hip. He guided the head of his cock to her entrance and pushed in, the heat of her cunt a stark contrast to the water running over their skin. He fucked her from behind under the spray, the wet slap of his hips against her ass loud in the small space, her freckled back arching, the muscles in her thighs flexing. Water ran down the crack of her ass and over the place where his cock stretched her open. He came deep, the pulses of his orgasm forced out by the clench of her walls, then pulled out and watched the water dilute the cum that leaked from her. She made him keep the dripping panties on while he towel-dried her, the soaked cotton heavy and cold against his softening cock, every brush of the towel against her freckled skin leaving him hyper-aware of the fabric still trapped between his legs.

Mid-afternoon when she got home early she found him on the couch scrolling his phone in nothing but the black briefs. The afternoon light through the blinds striped his bare chest and the pale pink of his thighs. She didn’t speak. She simply climbed onto the couch, straddled his face, and pulled her skirt up. The scent of her cunt filled his nose—warm, musky, already wet. She ground her bare folds against his mouth, the soft lips parting, the slick heat of her coating his tongue and chin. Mark licked and sucked, the taste of her sharp and salty, the texture of her inner lips soft against his tongue. She rocked her hips, smearing her wetness across his face and down onto the front of the panties until the cotton was soaked through again and clung to his half-hard cock. Only after she came—thighs clamping around his ears, a long, shuddering moan, her juices flooding his mouth—did she slide down his body. She freed his cock from the wet fabric, the air cool on the saliva-slick shaft, and sank onto him reverse-cowgirl. He watched the wet black cotton stretch and frame the base of his cock every time she rose and fell, the fabric shiny with her earlier release, the pink of her inner lips visible around his shaft. The wet sounds of her cunt taking him were filthy and rhythmic. She rode until her second orgasm made her clench hard enough that he followed, spilling into her while staring at the ruined panties stretched around the root of his cock.

That night in bed with the lights off the only illumination was the faint glow of the streetlamp through the curtains. Talia lay on her back, knees spread, the freckles on her inner thighs barely visible in the dark. Mark settled between them in the same pair of panties, now stiff with dried cum and her juices, the cotton rough against his skin where it had dried. He lowered his mouth to her cunt and ate her slowly, the taste of their earlier sex still lingering, the soft folds parting under his tongue, her clit swelling against the flat of it. He licked and sucked until her thighs shook and her fingers twisted in the sheets, her wetness coating his chin and dripping onto the already-filthy panties. When she came with a quiet, broken sound he pushed inside her while the waistband still dug into his hips, the dried fabric cracking slightly as it stretched. Her cunt was hot and swollen and still pulsing from her orgasm; every thrust dragged the stiff cotton against his balls. She came twice more before he finished, her walls fluttering and clenching around him, the wet heat of her milking every drop. When he finally pulled out she reached down with careful fingers, tucked his soft, sticky cock back into the ruined cotton, and kissed him with a satisfied hum, the taste of her own cunt still on his tongue.

“Week one done,” she whispered against his mouth. “You look good in my panties, baby.”

Week two flipped.

Mark’s team crushed hers by forty points. The apartment still smelled like sex and laundry detergent when he told her the new rule.

“Every morning. Blowjob before I get out of bed. No exceptions.”

Talia’s blue eyes narrowed, but the bet was the bet. Monday morning the light through the blinds was still gray when she woke him with her mouth already around his soft cock. The sheets were warm; her freckled body was warmer. She sucked him slow and wet under the covers, the heat of her mouth a sudden, slick pressure around the three-and-a-third inches of his soft shaft. As he hardened she took more of him, lips stretching, tongue pressing along the underside, one freckled hand stroking what she couldn’t fit while the other slipped between her own legs. The wet sounds of her sucking were muffled by the blanket; the scent of sleep and skin and her rising arousal filled the small space under the covers. Mark’s fingers tangled in her red hair, the strands soft and slightly damp from the night. He lasted longer than he expected; the novelty of waking up to her throat made the blood surge into his cock until the average five-and-one-sixteenth inches was fully hard and throbbing against her soft palate. When he came she swallowed every drop, the contractions of her throat working around him, then licked him clean with slow, thorough strokes of her tongue, tasting the salt of his cum and the faint musk of sleep. Only then did she let him sit up, her lips shiny, her freckled cheeks flushed.

That same morning after she finished he was still hard, the head of his cock flushed and sensitive. He rolled her onto her back, pushed her knees up toward her freckled shoulders, and fucked her deep while the taste of his own cum was still on her tongue. Her cunt was already wet from touching herself during the blowjob; the first thrust sank him to the root in one smooth, hot glide. The wet heat of her walls clamped around him, the soft give of her body under his hips, the way her 32C tits shifted with every thrust. She came around him with a sharp cry, nails digging into his shoulders hard enough to leave crescent marks, her inner muscles fluttering and milking him until he followed, flooding her with thick pulses while her legs trembled around his waist.

Wednesday night, after the morning ritual that had left his cock clean and satisfied, she was restless. The kitchen light was bright and unforgiving. Mark bent her over the kitchen table, the wood cool against her freckled forearms and the soft undersides of her breasts. He yanked her yoga pants and panties down in one motion; the fabric bunched at her knees. Her bare ass was pale and freckled and already slightly arched. He took her from behind while she was still talking about work, the first thrust cutting her sentence short. His average cock stretched her just enough; the wet slap of his hips against her ass was loud in the quiet kitchen, the soft flesh of her cheeks jiggling with every thrust. He could see the place where he disappeared into her, the pink of her stretched rim, the way her freckles moved with the impact. The scent of her cunt rose between them, sharp and wet. He finished fast, the pressure building too quickly from the visual and the tight heat, and stayed buried inside her until he softened, feeling every small after-twitch of her walls. When he pulled out he watched his cum drip down the freckled insides of her thighs in thick, slow trails, the sight filthy and satisfying.

Thursday morning the blowjob turned into a sixty-nine under the warm sheets. She started as usual, mouth sliding down his soft cock, but he pulled her hips over his face until the soft, freckled weight of her thighs framed his head and the wet heat of her cunt settled against his mouth. He licked into her while she sucked him, the taste of her morning arousal sharp on his tongue, the soft folds parting under the pressure of his lips. The wet sounds of their mouths on each other filled the small space under the covers. They came within seconds of each other—her grinding down hard on his tongue, her juices flooding his mouth, him pulsing against the back of her throat in thick, rhythmic spurts that she swallowed without pulling off.

Friday night, after the morning ritual, he kept her naked all evening. The apartment was warm; her freckled skin glowed under the lamps. He fucked her once on the couch, her long legs wrapped around his waist, the soft give of her 32C tits against his chest, the wet heat of her cunt taking every inch of him while the couch cushions creaked. He made her come once that way, then carried her to the bed and took her again, slow and deep the second time so he could feel every flutter and clench of her walls around him. She came three times before he allowed himself to finish, her freckled body arching and trembling, her cunt pulsing so tightly around him that the final orgasm was dragged out of him in long, heavy pulses. When he finally pulled out she was shaking and smiling, the insides of her thighs shiny with their combined fluids.

“You’re getting mean with your wins,” she murmured against his neck, breath warm.

“Just following the rules.”

Week three belonged to Talia again.

The scores came in and her smile was sharp. “Panties all day, every day. Outside the apartment too if you leave. Inside, panties and a bra. Nothing else.”

She had already bought him a simple black t-shirt bra that almost fit his flat chest. The cups sat empty and slightly ridiculous, the underwires pressing against his ribs, the straps digging into his shoulders with a constant, unfamiliar tension. The panties were a pale pink pair this time, soft cotton that stretched tight over his soft cock and balls, the front panel cupping him into a smooth, feminine bulge. That was all he was allowed to wear once the front door closed behind him. The air of the apartment felt colder against his bare skin; every movement made the empty cups of the bra shift and the pink cotton rub against the head of his cock.

The moment he finished dressing she pushed him against the wall in the entryway. The plaster was cool against his bare back; the bra straps cut into his shoulders. Talia dropped to her knees on the hardwood, freckled hands settling on his hips. She mouthed his cock through the pink cotton until the fabric was transparent and sticky, her breath hot, her tongue pressing the weave against the sensitive head until pre-cum soaked through. She pulled the crotch aside just enough to free the head and sucked it, lips sealing around the flared ridge, tongue swirling, the wet heat of her mouth a sudden contrast to the cool air. Then she stood, turned, and bent over with her hands on the door, her freckled ass presented, the long line of her back arched. Mark yanked the pink panties to the side; the elastic bit into his hip. He guided himself to her entrance and pushed in hard and fast, the empty bra cups bouncing with every thrust, the underwires digging into his ribs. The wet heat of her cunt swallowed him; the slap of his hips against her ass was sharp and rhythmic. He came inside her with a groan, the pulses of his orgasm forced out by the tight clench of her walls, then pulled out and watched the thick white of his cum leak from her. She made him tuck himself back into the wet pink panties before he was even soft, the fabric clinging cold and sticky to his spent cock.

That night she kept him in the bra and panties while she rode his face, then his cock. The bedroom lamp cast a warm glow across her freckled skin. She settled over his mouth first, the soft weight of her thighs on either side of his head, the wet heat of her cunt grinding against his tongue until he was coated in her taste and scent. When she came she stayed there through the aftershocks, then slid down his body, pulled the pink crotch aside, and sank onto his cock. The underwires of the bra pressed into his ribs every time she leaned forward; the empty cups shifted and bounced with her movements. Her freckled tits swayed above him, nipples tight; her long legs bracketed his hips. She rode him with deep, rolling strokes, the wet drag of her cunt around his average cock loud and filthy. She came twice before letting him finish, her walls clamping and fluttering, then made him stay inside her until he softened completely, the pink panties stretched around the base of him, the bra straps still digging into his shoulders.

The next morning he woke already hard, the pink panties tented and damp at the tip. Talia climbed on top without removing a single piece of his assigned clothing. She pulled the crotch aside with two fingers, the elastic stretching, and sank down in one slow, hot glide. Her cunt took him to the root; the soft heat of her settled against the stretched pink cotton. She fucked him slow, hands on the empty cups of the bra, pinching and rolling the fabric as if he had nipples worth attention, the underwires shifting against his ribs with every movement. The visual of her freckled body moving above him while he wore her lingerie made his cock throb harder. When she came she stayed seated, grinding in tight circles until the clench of her walls dragged his own orgasm out of him in thick, pulsing waves that filled her.

Mid-week when she got home from work she found him on the couch in nothing but the bra and a fresh pair of black lace panties she had left out for him. The lace was soft and slightly scratchy against his cock, the pattern of the weave pressing into the sensitive skin. She didn’t speak. She straddled his lap, the fabric of her skirt pooling around them, and rubbed her bare cunt along the lace until both of them were soaked, the heat and wetness of her turning the black lace translucent and shiny. The scent of her arousal was thick between them. Then she reached down, pulled the lace aside, and took him inside her, sinking down until the soft lips of her cunt kissed the stretch of the panties around his base. She rode until the lace was ruined and her thighs were shaking, her freckled ass flexing under his hands, the empty bra cups bouncing with every downward stroke. When she came the clench of her cunt forced him over the edge; he spilled into her while staring at the black lace stretched filthy and wet around the root of his cock.

That night in the bedroom with the lights on she had him on his back, bra still on, black lace panties shoved to the side. The overhead light left nothing hidden—the freckles on her pale skin, the empty cups of the bra on his chest, the average length of his cock shiny with her earlier wetness. She sat on his face first, the soft weight of her thighs framing his head, and ground her cunt against his mouth until she came on his tongue, the taste of her flooding him, the wet sounds filthy and close. Then she slid down, guided him back into her, and fucked herself on his cock while he watched the empty bra cups bounce and the black lace stretch around the base of his shaft. She came a second time with his name in her mouth, freckled body trembling, inner walls pulsing hard around him, then leaned down and kissed him wet and deep while he finished inside her, the taste of her cunt still thick on both their tongues, the underwires of the bra digging into his ribs with every breath.

When it was over she rested her freckled cheek on his chest, fingers tracing the underwire of the bra, the metal warm from his skin.

“Three weeks,” she said softly. “And you already look like you belong in these.”

Mark’s soft cock twitched inside the ruined lace. The elastic of the bra straps still cut faintly into his shoulders. Outside the apartment the real world still waited—work, friends, the rest of the season. Inside, the rules had already started rewriting the shape of his body and the way she looked at him.