Patron Reward: Cheerleaders And Chess (Patreon)

A reward I've been working on over the past few months. A bet between two rival school's sports teams leads to a humiliating payoff: the three hottest cheerleaders have to bang the winning team's chess club nerds. Oh the tragedy of hentai characters never being able to say "no, fuck that" to a bet! 

Friendly warning of some stereotypical nerd characters and mild raceplay, but nothing too shocking since it's mostly about awkward sex and clear social status differences.

The rivalry between Parker County High and Socom Valley High seemed only natural. Parker County was a public school, open to just about anyone to attend while the nearby Socom was a private school. It made them more exclusive, and their high standards made them the home of the children of wealthy sorts like celebrities and politicians. Their upper class status didn’t keep the from participating in sports like the rest of the schools in their state, and it created some natural friction between the two nearby schools. Students always showed up to cheer on the teams, and pranks or scraps between the opposing players were unavoidable (if firmly discouraged by the schools themselves).

The teams had managed to avoid any trouble like that this year, but they had arranged their own bet in private. The loser of the next game would have to send some of their cheerleaders to fuck the winning school’s chess team. Even between the public and private schools, the stereotypes remained true to both of them; skinny or chubby nerds in their chess clubs and athletic, good-looking beauties for cheerleaders. Both teams had to talk the girls into it, but some of them volunteered just to see the looks on the Parker/SV losers’ faces when they had to sleep with the opposition’s biggest geeks. The game was intense, but a burst of speed from a receiver landed Parker County the winning touchdown in the final quarter. The stands went wild over the intense rivalry coming to a climax, but the three of their cheerleaders who were onboard with the bet felt her hearts sink into their stomachs. They’d have to pay up their end of the deal by next week.

---

“This sucks! Why do we have to pay for their losing? Those jocks that blew it should be the ones putting their asses on the line,” Shani complained as the three girls entered Parker County High.

“Cuz we had to open our big mouths. I hope they don’t make me take it up the ass, It’s always so messy,” Monique whined beside her.

Shawni, Tisha, and Monique were still in cheerleading outfits, but as part of the deal, they were even skimpier and sluttier versions of what they normally wore to games. There was no coach to keep them from showing off some extra skin, and these new outfits covered little more than your average set of underwear. The curvy girls’ big brown booties and hefty underboobs fell out of their skimpy golden skirts and tops. The SVH logos that were stretched across their tits got everyone’s attention as they passed through the halls, but the rumor had spread enough that everyone knew they were coming. What would have normally been dirty looks were replaced by knowing smirks and lusting leers.

Shani shoved open the door to the chess club’s meeting room. She was in the lead as the head cheerleader and the first to join in on the bet. Her hair was a big curly mop of dark brown, only slightly darker than her skin. She had some clear muscle to her arms and legs, but they were dwarfed by the size of her giant tits and ass. Boobs twice the size of her head wobbled around in her tiny top, and a tiny, hot pink thong only emphasized the huge scale of her butt that was twice again the size of her rack. Pouty, gold-colored lips the same color as her hoop earrings pursed into an impatient frown as she scanned the room.

Four pasty boys sat around a table where two of them were in the middle of a chess game. They looked up in surprise at their sudden entry, expecting to get harassed by a bully. Their shock remained, but their posture relaxed significantly at the sight of the three dark beauties with their curves blocking the doorway. Shani grimaced in distaste at the display of stereotypical dorks and geeks.

“Okay, losers. A deal’s a deal. Get those scrawny little dicks out and let’s do this,” Shani demanded.

Spencer adjusted his glasses. The freckled, red-haired boy was tall, but he was so skinny that it made him look even more awkward than he already was. He was the team captain, for what that was worth, making him marginally more outgoing than the rest of them.

“So you’re here for the bet. Okay. Uh… how do we get started?” he offered, trying to remain polite but eager to claim his unearned prize.

“Virgins. I knew it,” Monique tutted beside her teammates.

Shani marched up to him with long, booty-quaking strides. She pulled on the back of Spencer’s chair, spinning him around to face her. She knelt in front of him and unbuttoned his slacks with a suspicious ease. She dropped his pants and briefs, immediately curling her lip in revulsion. His hard, uncut dick was a few stubby inches long, and it came with a sweaty smell that stung her nose and reeked of unused musk.

“Ugh! Stupid bet,” Shani grumbled.

She didn’t care if Spencer heard her. Clearly he didn’t either since his dick only grew stiffer and twitched against her tits that squashed out over his lap. She curled her fingers around it, starting to stroke him off while hoping that would be enough for him to accept it as payment for the bet.

“Ohhh that’s good,” the ginger boy moaned, leaning back in his chair to shove his cock further into her grip.

“Use your mouth too.”

“God dammit.”

Shani winced and wrapped her mouth around his bitter-tasting dick. He didn’t take much to grooming, as she immediately found through the taste of his cock. If she looked like the did, she wouldn’t be expecting to get laid anytime soon either. Her slutty instincts got the better of her, finding her tongue rolling around his dick and peeling back his foreskin. The nasally voiced nerd moaned and started thrusting at her, piercing his scrawny white cock between her golden lips and silver tongue.

Her squatted down position left her thick ass sticking out well past the confines of her skirt. Her medicine ball-sized ass cheeks bounced up and down temptingly as the other nerds watched with envy. Two of them looked up to Monique and Tisha before hurrying over to the much less enthusiastic girls.

Reggie lingered by the table. He was the opposite of Spencer, if no more attractive. He was a squat, chubby runt with square-framed glasses and greasy, overly combed hair. He had his eyes set on Shani as well and moved in behind her. He didn’t even have to lift up her skirt to peel down her thong, pulling it aside and thrusting into her pussy from behind. Shani let out a disgruntled grunt, but her oral movements and the sudden push from behind made her mouth go harder on Spencer. The red-haired boy moaned and buried his fingers into Shani’s curls, pulling her head down further onto his cock. His slippery white shaft wasn’t big enough to hit her throat, but it still made her gag to have both of the geeks inside her at once. Shani’s big ass still bounced and jiggled around regardless of how much she hated it. Reggie’s fat cock pumped her pussy while his stomach pushed at her ass, forcing them both to wobble around.

While the boys spitroasted Shani, Monique winced as she let Marcus get his hands all over her. Marcus was a fat, long-haired nerd with a stubbly neckbeard that kept tickling against her skin.

Monique was shorter than Shani but nearly as thick as she was. Her long, shapely legs ended in a fat ass to match the rest of her crew. She had a lighter, milk chocolate skin tone and her hair was a tangled swirl of a more caramel color. It was woven into numerous braids topped with pompoms of hair above each of her ears.

The heavy nerd was emboldened by his classmates already making their moves and didn’t waste any time. He had lifted Monique’s top right over her head until her thick big perky tits bounced around in Marcus’ clumsy hands. He quickly guided one into his hungry mouth, moaning in ecstasy. He threw off his jeans and sweat-stained shirt, grinding his cock against Monique’s thigh like a desperate dog in heat. She turned her head away and stuck out her tongue, gagging on the smell of the perving chess player. Marcus was undeterred as he managed to blindly feel his way between her thighs, since he couldn’t see down past his mouthful of dark breast meat. His drool ran down the steep curves of her tits as he fumbled at her skirt in his clear lack of experience at undressing someone else.

“Alright, alright. At least let me get off my feet for this bullshit,” Monique complained.

Athlete or not, she was still the spoiled daughter of a local jeweler. She at least didn’t want to go through this demeaning act with tired legs. She looked around and with an awkward shuffle away from Marcus (who continued to cling to her anyway), she at least got to lay her naked body back on the couch.

Marcus climbed on top of her and finally jabbed his cock inside Monique, his face still latched onto her tit. She groaned underneath him. It wasn't from arousal so much as his weight on top of her made it harder for her to breathe. She squirmed in discomfort, trying to adjust herself so she could at least get off to the fat boy’s eager humping.

“Come on, already. At least TRY and reach the clit, you fat fuck,” she groaned, cutting herself off with a hiss as he bit down on her nipples.

That left Tisha with Nate. Tisha had straight, dark hair that she kept tied  into a ponytail with a ribbon. Her beach ball-like ass was big enough to stick out plenty above and below her skirt, and half of her round tits hung out below her top. She had a slightly sweeter default expression than her fellow cheerleaders, but she still winced at the sight of her mandatory mate.

The last of the dorks was short and thin, giving Tisha no doubt that he had a dick to match. He grinned at her, flashing his braces while his shaggy hair hung over his eyes. Nate was even dressed in a bowtie and suspenders over his needlessly semi formal clothes he wore to school. He squirmed in his chair, reaching out and making expectant grabbing motions at her.

“Fiiiine. Just whip it out and let's get this over with,” Tisha groaned.

She cringed as he peeled off his suspenders like it would do anything to help his sexual appeal. He fumbled through dropping his pants, unveiling his expected disappointment of a cock. At least it was hard, which was hard not to do when looking at the barely dressed cheerleader. Tisha rolled her eyes as he sat back in his chair, staring at her expectantly.

“This’ the last time I make a bet with my pussy on the line,” she grumbled as she hooked her thumbs under her thong.

She lifted one thick but flexible leg, stepping out of her underwear and feeling the familiar breeze of the open air against her bare pussy. She straddled Nate’s lap, a leg spreading out on either side of him to mash her crotch against his. She similarly wrapped her arms around his neck, defaulting to a position she knew her boyfriend liked. The straddling sexual lapdance was a lot easier with her boyfriend’s bigger dick involved, but she made it work as best she could. Nate certainly couldn’t tell the difference, reaching around her thick hips and squeezing her big dark cheeks tightly. The fatty ass meat oozed through his fingers as he humped around just barely inside her pussy lips.

“Nnng! That’s so good!” the scrawny geek moaned beneath her.

“Mother fucker never heard of a clit?” Tisha muttered under her breath.

“Huh?”

Tisha hissed through her teeth. She remembered the faster he finished, the sooner she could leave.

“Nothin’. You’re doin’ great there, stud,” she chimed with a forced smile.

Nate sighed, not needing much encouragement to keep enjoying her body. He pushed his head under her top, burying his face between her tits. He sucked hungrily on her Hershey kiss of a nipple as the skimpy shirt rode up higher. The already taut top flopped up, exposing her braless tits for his groping and sucking pleasure. Tisha just rolled her hips, bouncing her ass in his hands and breasts in his face while she hoped he was a quick cummer.

Shani moaned as she was trapped between the two nerdy dicks. She was still on all fours with Spencer and Reggie taking her from either end. Despite their utter lack of rhythm and experience, she was actually getting wet from the experience. It wasn’t pleasant, but the double dicking was helping Reggie ram her hard enough from behind that he could actually tease against her clit. Half of it was just the ripple of her big fat ass as his hips clapped against it rapidly. Shani even found herself rolling her hips in time with his thrusts to get a little pleasure from it herself. It made the cheerleader’s infamous ass cheeks wobble and clap against Reggie’s lap.

“Mmmhmmf!” she moaned out in a muffled curse of excitement.

If Shani was being humiliated anyway, she could at least try to enjoy herself as best she could. Her rolling tongue stroked and curled around Spencer’s shaft, teasing around the tender space beneath its head. The tall nerd moaned and leaned over her, pushing himself further into her throat. She stared up at his spectacled face as her thick, pouty lips pushed against the skin around his cock. She rolled out her tongue to slip his musky balls into her mouth, subtly shaking her head to slip them inside as well. With a loud, firm smooching sound, she lingered there and slowly drew back. His sack was coated in her runny drool while she had left a golden lipstick print in her wake.

“Ohhh my god,” Spencer grunted nasally.

His legs went weak at the slutty maneuver. He gripped a big handful of Shani’s hair, steadying himself and her head as he started thrusting harder into her mouth. The cheerleader let out a shrill gurgle as her lips instinctively latched around his dick like they always did when somebody pulled her hair during a blowjob. Her noisy slurping tugged his dick as deep into her mouth as it would go. Spencer babbled a string of horny noises as he buried both hands into Shani’s curls, pushing her face into his pelvis as he came in her mouth. The black girl gave another thick choking noise as the ginger’s cum filled her face up. Her full lips managed to catch it all before it could spill out, but she had to keep her mouth shut to keep it in.

From behind, Reggie was panting as he clapped her cheeks. He had to push hard to get past her thick ass, squashing it between his belly and her hips. He still kept ramming against the underside of her clit, teasing a steady slow of her juices out of her. Her bubbly tits swung around and bumped together beneath her as she braced herself like a beast of burden for him to get off on.

“Ughhh.. I’m gonna…” the sweaty dork panted.

Shani’s eyes widened as she realized what he meant. She withdrew her face from Spencer’s lap and tried to turn to face Reggie, only to choke on his cum in her haste. She coughed up a glob of white over her dark cleavage, coughing wildly and unable to stop him. The spasming of her body made the short boy moan and thrust hard enough into her he was practically riding her ass. He bumped deep into her pussy like he was knocking on the door of her womb right before he shot his seed deep inside her. He moaned and leaned over her, hugging her fat ass and resting his head on her lower back.

Shani finally managed to spit out of the last of the cum to turn and snap at him.

“Did you just fucking cum in me, pipsqueak!?” she demanded.

“Uh… yea. Wasn’t that part of the bet?”

“I came inside you too, if that matters…” Spencer muttered.

“Not unless you figured out how to nut through my throat into my pussy! You’re lucky I took my pill this morning!”

Shani paused and pursed her pouty lips. She DID take that damn pill, right? She was in such a hurry to get all this over with…

----

Monique grunted as Marcus fully mounted her. He had seen enough hentai to know what he was after, and fortunately her body was flexible enough to take it. He pushed her legs up and over her ebony body, pushing her toes up near her shoulders as he stuffed himself deeper into her pussy. She gave an annoyed groan as his dick pumped up and down her slit, making his fat belly wobble around on top of her.

“Ohhh yea… that’s so good. Please… call me ‘daddy,” he moaned.

“Ugh… whatever, perv. I mean, daddy,” Monique conceded.

Marcus moaned loudly and leaned over her, mashing his lips into hers. The taste of the candy she’d been snacking on during her walk over made her mouth even more enticing as she shoved his tongue inside her. Monique grimaced as his stubble itched her skin and he drooled over her, but she needed to hold up her end of the deal. She reached down to grasp his hands, moving them up to her tits. She jiggled them against his grasp like a distracting set of toys to keep him entertained. He grabbed the meaty handfuls and pinched around her nipples, making her wince while acknowledging that it was working.

His thick hips started bouncing her harder, slapping his balls against her big round cheeks. The tiny spanking was one more humiliation she had to put up with, but at least he seemed to be finishing up. She bit her lip, forcing herself to focus on the grody feeling of nerd dick inside her. Monique shook her hips and made her pussy flex around him, doing anything she could to hurry Marcus along.

“Oh! That’s so hot! Yesss!”

Marcus’ heavy breathing and moaning moved from her lips down to Monique’s breasts. He grabbed two greedy handfuls of the dark melons, holding the bouncing orbs in place. Marcus’ wide eyes drank in all of her figure that he could at once, from her bouncing curls to her fat ass squashing against the couch cushions. The messy furniture squeaked rhythmically beneath their combined weight, and Monique grimaced from the feeling of their snack crumbs sticking to her sweaty ass cheeks. She felt Marcus’ cock twitch inside her as a spurt of precum spilled inside her pussy.

“Nngh… okay! I think you’ve had enough,” Monique laughed awkwardly.

“Think it’s time for you to pull ouOOFF!”

Monique’s attempts to make him pull out were interrupted by the incredibly distracted nerd kissing her full on the mouth. She sputtered and tried to pull away from his kiss in disgust, but he shoved his tongue in her mouth before she could spit it back out. She gagged on his spit as she tried to turn away, but that only distracted her from the bigger problem. Marcus’ dick swelled and shot off inside her, emptying his virgin balls into the thick black beauty. Monique’s eyes went wide, trying to squirm out from under the fat nerd, but he was too heavy and too far inside her. She ended up rolling to one side, tipping him callously off the couch. Marcus landed with a meaty thud, but he had already finished. Monique sneered as she hastily started wiping at her sloppy snatch.

“You fat little bitch! You better hope that little dick of yours didn’t get in deep enough!” she threatened as she tried to clean up his mess.

Tisha started to grind more enthusiastically on Nate’s lap. She lost herself in keeping up with the rhythm playing in her head to the song that she played last time she lapdanced for her boyfriend. The skinny nerd could feel her wide ass slapping down on his legs while her tits filled his face. He sucked hungrily on one of her nipples, making his braces prick at her skin. Tisha winced and wrapped her arms around his head, hugging him tighter between her sweaty cleavage. He wasn’t that hung, but Nate had some surprising stamina. He could barely keep it hard, which may have been a part of it, even with the overly curvy cheerleader sitting on his lap.

“You like that, stud?” she panted, trying to throw some encouraging dirty talk into the mix to get him going.

“Mmf… yea…” the nasally dork groaned back.

He leaned back into his seat at her slutty praise, thrusting his cock more firmly into her.

Tisha pulled back enough for him to fully look at her rocking upper body. She gave him a flirty glance like she always used whenever she wanted to tease strangers and get boys to do what she wanted. Nate swallowed hard as she met his eyes.

“You think I’m pretty, right?” she pried.

She was half baiting, half bullying him into getting even hornier. He nodded rapidly.

“So hot,” he squeaked.

She felt his inexperienced dick twitch inside her, clearly never having to stay hard for this long in his dorky lifestyle. He hadn’t fucked anything more involved than a sex toy, so he was still figuring out what to do with this much woman. Tisha resisted rolling her eyes at the skinny geek and leaned over to whisper in his ear.

“What’ll make it even hotter?” she cooed to him.

It made a shiver run up his spine, making him vibrate underneath her. His hands ran up her thigh, but his eyes darted around, avoiding hers while clearly thinking of saying something.

“Uh… well…” he mumbled awkwardly.

Tisha was about to sigh at his pathetic behavior when she felt his hand hovering around her ass. When her cheeks bounced from her riding rhythm, she could feel his fingertips touch her soft skin with a light tap. She raised an eyebrow as she seemed to catch on to what he was trying to say without the guts to do so: he wanted to be rougher with her.

Tisha smirked and grabbed his wandering hand, bringing it firmly against her ass. The loud, meaty slap sounded off as her cheeks wobbled beneath his palm, reddening slightly from the sharp impact. She moaned as she leaned in, nibbling his ear.

“Why hold back? I want you to get real nasty and fuck my big black ass like you know you want to, you nasty boy.”

With her outright permission, Nate felt his more sadistic urges take over. He had no idea when he’d have another opportunity like this, and with his shyness cast aside he took her by the thighs. He leaned into her, barely able to move or lift her at all with his scrawny body but it was enough to tip her over backward. Tisha squealed in surprise, a look of real shock crossing her face. Only her cheerleader reflexes managed to adjust her posture and bring her arms back to catch herself in time to avoid banging her head on the floor.

That was only temporary anyway as Nate really let loose on her. He folded her legs up and over her head, leaving her stuck upside down with his cock still inside her. Her heavy tits swung up into her face, blocking out some of her view instead of his as she stared up in shock at him. The boy bit his lip with unbound lust as he plowed into her from above, making her whole body quake with his efforts.

“MMF! Yea! Take that you dirty slut. You fucking cunt. How you like that fat white cock, bitch?!” the pent up geek ranted.

Tisha was speechless. She didn’t expect it in the least, but he clearly had some anger issues and closeted kinks that were coming out at the moment. She gawked up at him, shocked at his behavior. She was almost as surprised by how turned on she was by his aggression. At least he was doing something interesting.

“Oh… uh, yea! Right! I fuckin’ love it. Fuck me up, white boy~!”

Tisha had said lamer stuff during sex. She just wrapped her legs around Nate’s waist, keeping him stuck deep inside her. Nathan slapped her across the tits, and at least he wasn’t strong enough to do any real damage. It was still humiliating, but if letting him roughly grab and slap her curves around helped get this over with (while making it a little more fun for her), so be it. Besides, his mating press position let him get in deeper and fuck her harder, and was actually starting to feel pretty good if a bit dizzying.

“That’s right. Here it comes. Open up and take that strong white seed!”

“Ohhh yeaaa~! Give it to me, Na- wait! No! UAHHHH~!”

Tisha’s eyes widened as the rush of hot jizz poured down her pussy. The shock to her system and the building pleasure mixed together in a stunned orgasm of her own. Her pussy loosened up and squirted as it clung to his scrawny white dick, practically sucking the cum out of him. She was stuck wide-eyed and mouse open as she shivered and jiggled beneath him, her legs hugging him tightly inside her. Nathan groaned as he leaned over her, finishing burying his seed inside her hungry black pussy.

“That… that was…” Nate panted, smiling in dopey bliss.

“SO gross!” Shani barked as her own sexcapades resolved themselves.

She stood up and angrily grabbed her clothes. Monique was doing the same, so Tisha snapped back to her senses and started to crawl out from under the winded nerd. Some of the rival school dorks had to puff on inhalers in the aftermath while the cheerleaders hurried to pack up.

“There! The bet’s paid for! I don’t wanna hear another word about it,” Shani demanded.

She pulled her top back on as Spencer quietly snapped a pic of the redressing girls. Monique shot him a furious glare, but he shrugged.

“Just for… proof for the bet?” he squeaked with a tiny grin.

---

The following week was a busy and uncomfortable one for the girls. Rumors spread about the cost of their bet, and soon all three of them were receiving knowing looks and barely concealed snickers. Shani had to blow off members of their school’s chess club trying to hit on her after hearing that she “had a type,” and the cheerleaders were all rapidly ignoring or blocking attempts from their unwanted lovers on social media. Their cheer squad was all annoyed at them for ruining their reputation, and any of their boyfriends started finding excuses to see other girls. The experience had Shani, Tisha and Monique all feeling disgusted, but at least it was over with. However, the nausea didn’t end there. It didn’t add up until Tisha got a text from Monique.

“Hey, Tish? You might want to test.”

“Test for what?”

A month after their regretful meetup, the Parker County chess team was having another meeting. They were back in their messy little classroom, fussing over their games and whatever dorky conversations topics came up, when the door was slammed open. They jumped in surprise as they saw the trio of cheerleaders standing in the doorway. They looked pissed and… bigger than before? They were dressed in more comfortable clothes than they had been wearing last time, clearly not here for seconds on sex. Their already huge tits filled up their shirts and sweaters while a protruding belly swelled underneath them.

Shani stepped forward and thrust her hand towards them. It held a pregnancy test with a little + sign in the middle.

“Listen up, you dirty little fucks! We got shit to talk about!”