Chapter Text
Oliver was finally going to do it. He’d finally built up enough gumption to ask out the girl of his dreams, Wendy Barton; captain of the girl’s football team, subject of many tomboy girlfriend memes in Dalton high school Discord, and all-around cool beauty. Normally Oliver wouldn’t have a chance with her, considering he was a small boy, weighed thirty pounds wet, and had a bit of a babyface, but recently Oliver got to know her during the summer. He went to a chess championship, participated in the finals, and strangely he met Wendy at one of the newbie tables. Her father was catering the event, she had little to do, was bored and got curious about chess while watching the junior finals. Oliver offered to teach her a few moves and surprisingly she accepted. And even more surprisingly she was very nice, lacking her usual cold stare, and imposing aura. She was genuinely curious about chess and Oliver spent the last few days of the tournament teaching her how to play at the newbie tables. It was great and she was a surprisingly quick learner. Oliver offered to spend some time teaching her when school started, and he bought her a new portable chess set. Hoping to play a few matches with her next time she was free.
Oliver waited by the school courtyard fountain, on the first first day back. The sound of falling water and excited (and not so excited) students filled the area. Oliver was keeping a sharp eye out for Wendy and after a couple of minutes, he saw her long black ponytail peeking up from behind the crowd. Oliver waded through dozens of his classmates and walked up to Wendy who was chatting with her friends. She had a cherry lip gloss that made her lips shine slightly, and the famous cold stare that scared off most guys. “Hey, Wendy,” said Oliver, causing Wendy to look over and give him a blank look. Oliver tensed up and lost a bit of his never, but it was too late to give up now. “I just… I just wanted to…” But before he could spit it out, Oliver felt a hand on his shoulder. “Get the fuck out of my way faggot.”
Then before Oliver realized what was going on he was knocked onto his back. His glasses were tossed onto the pavement below him. Oliver scrambled to grab his glasses, luckily they were unbroken; a plus side to getting the thick metal frames. Oliver looked up, putting on his circular spectacles to see the captain of the track team and famous asshole, Sam Bulger. The guy acted like he owned the school, and all because he was a tall, black, muscled pretty boy who won the school three first prize trophies; not even mentioning his family connections. Plus he never followed the dress code, opting to wear a thick hoodie and sweatpants, opposed to the white short sleeve dress shirt and khakis (or skirt) the other students had to wear. Oliver won the school trophies too, but chess never got the respect it deserved.
He had already had an arm around Wendy’s shoulder and was smugly asserting himself right after pushing Oliver. “Heeey girl,” said Sam, his voice sly and giddy as he continued, “I hardly heard from you this break.” He puckered his lips mockingly as asked, “When are you gonna slide some sugar my way?”
Wendy just responded, “I told you, I’ll have time later…” The ringing of the school bell interrupted Wendy as she sighed, “But now I got class, let’s go girls.” Her two gal pals followed behind her as Oliver tried getting to his feet but Sam knocked him back again spitting, “Not done with you yet bitch.” Sam grabbed Oliver by his collar, pulling up his shirt as he continued, “Listen faggot I don’t know what your chess club looking ass is doing looking at Wendy, but back the fuck off.” Sam let go of Oliver, pushing him back against the pavement as he said, “You don’t want another confrontation do we?”
Oliver shook his head and Sam laughed, “Good boy,” producing a condom from his pocket as he taunted, “Can’t wait to use a couple of these tonight.” Sam ruffled Oliver’s dirty blonde hair, adding one last, “Later faggot.” Before he ran off after Wendy, who had barely entered the school. Oliver sat on the pavement for a moment, earning a few weird looks from his classmates as he sat, nearly in tears, but resolved that it would be best if he just toughed it out through the day. Who knows, his chess club meeting might cheer him up.
-Nine Hours Later-
The chess club meeting did not cheer Oliver up, and the fact it was an extra-long meeting too didn’t help. The first meeting of the year was always the longest and by the end of it, Oliver felt drained. Not even the janitors were still around after they finished. And just to make things a bit harder on Oliver it was his job to lock up after the meeting; being a team captain has perks after all. He waved out the other dozen or so members of the chess club. They all wished him a good night, though one of them, a slim ginger girl called Jenny offered him condolences. “I heard what Sam did to you this morning. He’s such a jerk,” said Jenny.
Oliver turned to face Jenny, possibly the only chess club member his height. She had a very slim body and pointed face, and her deep green eyes displayed concern as Oliver responded, “Don’t worry Jenny, Sam will continue to be a dick as long as his father is the principal and we can’t do anything about it.” Oliver sighed and waved her out, “Now get going, I’ve still gotta lock up.” Jenny paused, taking a quick look at Oliver before mumbling, “Hey Oliver, would you like to…” Oliver peeked up as Jenny spun around, “Actually I’ll tell you tomorrow, have a good night!”
For a second it looked like Jenny was blushing but Oliver figured he must’ve been mistaken; it was a long day. Oliver quickly cleaned and locked up the library before exiting the school, deciding to take the shortcut through the track field to get home a bit quicker. Though as Oliver rounded the corner he saw something a tad strange. The lights were still on in the school’s sports storage shed, and there wasn’t anyone around. No one running around the large rough, red rubber tracks, and the bleachers were empty. Oliver was about to leave, but he figured he should do the janitor a favour and lock up the equipment shed; plus a second raccoon infestation wouldn’t be good for anyone. Never again, thought Oliver as he walked over to the shed, and as he began opening the door he heard moaning, followed by the phrase, “You like that bitch boy?”
Oliver immediately perked up and peered through the door to see Wendy’s hot sweaty chocolate body grinding against… “Holy shit,” muttered Oliver as he realized Wendy was doing the fucking! In the middle of the storage shed Wendy was on her knees, completely naked overtop a bright blue wrestling mat. Her jiggling double Ds’ both tipped by dark nipples were bouncing up and down as she thrust her hips. Her slender toned hips and muscled tummy flexing with each balls deep pump into, “Sam!” Spat Oliver, stepping back, shocked to see Sam in all his… twinky glory. Sam drooled, his face displaying tortured pleasure as Wendy bulged his slender muscled midsection, her hands firmly on his hips as she cheered, “Was this the kind of action you were expecting big bo…” Wendy paused her thrusting, letting Sam twitch and limply drool on the mat as she asked, “Who the fuck is out there? Is that you, Britney, I already said that your turn is on Tuesday nights...”
“No, ummm, sorry I was…” Oliver tried to open the door slowly but tripped over himself. Accidentally throwing the door open hard enough to knock over a rack of footballs as he stuttered, “Ah sorry about that, just let me…” But before he could fix his mistake Wendy interjected, “What are you doing here… Wait, are you spying on us?” Her accusatory tone mixed with her cold judgemental stare made Oliver tense up (despite them technically being in the wrong, having sex on school grounds), but he still managed to squeak out, “Well after chess club I saw the light was on…”
“And,” asked Wendy, folding her arms under her breasts.
“And I came… to… to turn it off and lock up.” Stuttered Oliver trying his best to keep eye contact with Wendy as she... laughed? She just broke into laughter nearly falling over as she snorted, “Hahahaha, you’re such a dork Oliver,” Wendy wiped a tear from her eyes as Oliver awkwardly chuckled along. “But you’re a cutie, so tell you what,” Wendy slowly pulled her cock out of Sam’s ass, leaving his chocolate booty a gaping mess as he trembled, his little black cock twitching as Wendy continued, “If you like, I’ll give you a little service.”
Oliver blushed straightening his back as he said, “Oh well that’s… I don’t know if you’ll like me I’m…”
“Hey, don’t worry about it, chess boy.” Giggled Wendy as she stood up. Her muscled ass cheeks glistened with sweat along with her tight muscled, frame, thighs and cock; which must have been at least foot long and was slick with some kind of clear lube. Oliver wondered how no one noticed she had a dick, but answering the question was secondary compared to keeping as much composure as possible ass he strutted over to him. Their height difference was clear in an instant, Wendy had at least a foot on him and was smiling as she said, “It’s fine if you’re not packing.” Wendy squatted to Oliver’s crotch level and started unbuckling Oliver’s belt, her smooth hands gripping his beige khakis as she continued, “Bitch boy over there thought he was hot shit packing only four inches…
“Nyyggghhh, five…” moaned Sam, his body still twitching in pleasure.
“Whatever,” Wendy rolled her eyes and continued to pull down Oliver’s pants as he said, “Wendy I am flattered but I really don’t think…”
“Serious I said it’s fiiiiiine, a little white cock won’t make me… holy shit!” Wendy’s eyes went wide after she pulled down Oliver’s pants, she didn’t realize the beast she had released. A foot and a half-long white cock, topped by thick dirty blond pubic hair flopped out of those dorky khakis and nearly slapped Wendy across the face. Her jaw hung open as she stared up at Oliver wide-eyed and surprised. “I’m sorry I know it’s disappointing,” cried Oliver, looking away, “But I… It’s just how I am… Are you mad?”
“What the fuck are you talking about?” Wendy looked up at him, grabbing the base of his cock thinking, fuck, I can barely fit my fingers around it and his nuts are massive. They’re like fucking grapefruits and the smell... Wendy deeply inhaled, sniiiiffff oh fuck he smells better than Britney. She paused, licking her thick black lips before putting her forearm against his dick, shouting, “Your dick is fucking incredible, why on earth would you be ashamed of this massive, white, meat?” Wendy could feel her cock throb and her pussy trembled as she inhaled Oliver’s musk, this kid was something else. Yet he looked miserable as he mumbled, “Umm- weeeell,” Oliver paused his lips trembling and voice dismal as he continued, “My only girlfriend took one look at it and screamed. She said my cock was disgusting...”
“Haha, fucking nerd can’t even keep a girl with a big dick.” Chuckled Sam his energy returning to him. Oliver was nearly in tears, until Wendy shouted, “Shut the fuck up bitch boy!” She stood back up her cock slapping against her thigh as she looked at Oliver before saying, “Give me a second sweety.” Before walking over to a pile of clothes, pulling out Sam’s black sweat pants and producing a condom. “This bitch boy thought he was going to finally get to use this, ha.” Wendy moved over to Sam and stepped on his trembling black cock, “I told him he could finally smash if he shaved and toned himself up over the summer. I figured he’d finally deserve some sugar after being my mediocre cock sock for half a year, buuuuut no.”
Oliver looked at Sam tremble, his cock leaking over his stomach as Wendy ground her heel against him. Sam looked so pathetic in this state, body completely hairless, muscles slender, and on closer inspection, Sam was wearing eyeliner and some lip gloss. It really puffed out his thick lips, bringing out a feminine side in him that Oliver thought didn’t exist, but Oliver’s attention snapped back to Wendy as she continued, “I wouldn’t let this pathetic bitch boy anywhere near my pussy, but you Oliver, have a very good chance.” Oliver blushed as he turned his head away, but he couldn’t help cracking a smile.
Wendy reached down and dragged Sam by his tricep over to Oliver’s feet, dropping him as she opened the condom, “Ha, you bought the XL size,” Wendy shook her head, smiling, “Sam you silly sissy, you’ll never change. This condom couldn’t fit you if you were twice the size, but let's see if it can fit this “little” guy.” Wendy started to slide the condom down Oliver’s cock and it took up a whole third of his dick; getting mostly stretched out when his cock got thicker near the tip of his dick. “Look at that bitch boy, it doesn’t even fit half of Oliver’s massive white bitch breaker.” Said Wendy, her voice cheery as she asked, “Now, who is the bitch now?” But Sam just averted his eyes, dodging the question as he muttered to himself. “Hey bitch,” shouted Wendy, grabbing Sam’s afro, “I asked you a question, but maybe you can’t see?!” And with a quick motion, Wendy shoved Sam’s face against Oliver’s half-hard cock, “Now that you have a good look, answer my fucking question sissy.”
“Yes ma’am, ahhhnngg” muttered Sam.
“Yes, what,” demanded Wendy, tightening her grip on Sam’s hair.
“He’s waaaay bigger than me, aggghhh” Wendy pulled up on Sam’s hair, his nose pressing against Oliver’s cock as she asked, “Bigger than your, what?”
“Nyyyggghhh, h-he’s much bigger than my pathetic black sissy clit. I’m sorry for thinking I deserve to fuck your puuuussshhiii!” Oliver could see Sam’s cock get hard and twitch like an excited dog’s tail as he moaned. “Good girl,” chuckled Wendy as she looked down at his stiff clitty, continuing, “Awwww, the little masochist is already hard, do you want some love, sissy?”
Sam nodded, simpering like a lost puppy before Wendy shouted, “Too fucking bad,” throwing him onto the mat. Sam groaned, his body trembling as she continued, “I’ve finally got a cock worth fucking and I’m not wasting this premium opportunity with a sissy faggot!” Wendy looked over to a wide-eyed Oliver and winked, “Plus the guy it’s attached to isn’t too bad either.” Oliver felt his heart skip a beat as Wendy winked at him. Her big blue eyes looked so warm, her thick black lips looks so tasty. Oliver felt so overwhelmed and he just…
“Mmmmmmph!” Planted a kiss on Wendy’s lips, he could feel her tongue press against his, the taste of some cherry lip balm mixed into their spit, and Oliver felt her arms clap his shoulders, but instead of pushing him away (like he expected), she pulled him in. Embracing the small white boy in her arms, lifting him off his feet, his cock pressing against hers as she slid her tongue down his throat. It might have been the most intense moment of Oliver’s life and it felt like it lasted only a second.
“I should’ve done that this morning,” said Wendy after breaking the kiss. A single strand of spit connected the pair’s lips as Oliver muttered, “Yea, me too…” He straightened his crooked glasses as Wendy put him down and immediately dropped to her knees. “Wendy what are you going to, ahhhgggnn!” Yelped Oliver tensing up as he felt Wendy rip off the condom before planting her soft lips on tip of his rock-hard cock.
“Mmmmm, I’m just giving you that special service I promised, mmph!” Wendy’s lips enveloped Oliver’s cock head. He could feel her tongue slowly lick around his fat circumcised cock head. Her motions got a bit faster with each throb of his cock. “Mmmmph, such a tasty cock,” Wendy kissed his cock tip, “And I’m not going to let it go until I’ve had my fill!” Oliver squeaked as Wendy deep throated over half his dick, bobbing her head up and down the middle of his shaft. Wendy grabbed the base of Oliver’s meat with one hand and started pumping her own shaft with the other. Slow strokes along the un-throated part of Oliver’s cock.
“Wendy, it feels so gooo-mmmmpphh!” Moaned Oliver, his adorable face scrunching up only made Wendy want to take more of his cock down her throat. She pumped her own cock faster and faster as she swallowed all of Oliver’s white meat. Her throat bulging from the girth yet the sudden realization she couldn’t breathe felt secondary to keeping Oliver’s hot throbbing cock down her throat for a couple more seconds.
“Wendy I’m,” Oliver’s hands grabbed Wendy’s long black hair, causing her eyes to look up at him as he bit his lower lip, screaming, “Cuuuuuming!” Then without a second to prepare herself, she felt Oliver’s thick load bloat her insides filling her belly to the brim with his thick white seed. Wendy could feel it bloat her belly, and overflow up into her throat. I was the thickest thing Wendy had ever drunk, but she kinda liked it, feeling it seep into her body as Oliver’s cock pulsed in her throat felt strangely addicting, and it looked like Oliver felt the same way. He looked so relieved as he came, his cute little round face scrunched up as he softly moaned. Wendy didn’t even mind when Oliver leaned on her for support, barely keeping balance as he clogged her throat with thick white spunk.
Oliver exhaled as the last of his cum finished shooting down Wendy’s tight throat, and he muttered, “So-sorry Wendy, it felt too good.”
“Fucking hell Oliver,” spat Wendy, blowing cum bubbles as she spoke, “How long has it been since you last came?”
“Ummmm, well I couldn’t be alone at the chess tournament, or space camp, or hmmm.” Oliver rubbed his chin and thought before continuing, “About two months, probably three.”
Wendy licked her thick cum stained lips, scraping a bit of the spilt spunk into her gullet before responding, “You gotta unload more often…”
“Sorry, it’s just hard doing it by myself.”
“Mmmm, don’t worry I’m not complaining. That was a fucking tasty load, but we’re not done yet.” Wendy crawled over to a quivering Sam, his cock dribbling onto the mat as he watched Wendy’s throat get pumped by the scrawny white nerd he pushed into the pavement earlier that morning. Though Wendy was completely unconcerned by Sam’s shock and flipped him onto his ass while shouting, “Time to make yourself useful bitch boy!”
“Bu-but Wendy I’m,” sputtered Sam, unable to stop his moaning as Wendy slapped her cock between his fat black cheeks. “Shut up Sam,” Wendy brought her hand down on Sam’s ass, shutting him up as she continued, “You’ve cum like four times and I haven’t cum once.” Wendy pressed her cock head against Sam’s asshole and his bussy eagerly accepted her tip. “Now be a good bitch and shut up while I fuck your ass.”
Oliver watched as Wendy sunk a foot of big black futa dick into Sam’s ass, leaving not a single detail of the sissy’s ass breaking to his imagination. Oliver could see the twisted face of embarrassed pleasure Sam was making, he was trying not to make eye contact with either of them but his soft moans were not as easily contained. Oliver was about to leave the pair to their fuck session but was interrupted as he was pulling up his pants.
“Hey dork,” Oliver raised his head and looked over the Wendy, who had both hands on Sam’s hips as she asked, “Where are you going?”
“Well, I just thought I’d leave you two…”
“Fuck no,” spat Wendy as she reached back with one hand and spread her ass for Oliver continuing, “You’re the only man that’s got me close to orgasm tonight and I’m not letting you leave until you’ve given me a good pounding.”
Oliver blushed, he could see Wendy’s perfect black lips and heavy nuts as they slapped against Sam’s thighs. He really wanted to join, but... “I’m flattered Wendy, but I’ve never done it before and what if hurt…”
“Again, I don’t fucking care,” Wendy looked back her face shifting to annoyed as she shouted, “Ruin my cunt, shove it in and awkwardly thrust or cum early, it doesn’t matter!” Wendy let go of her ass and turned back, her long black hair whipping as she slapped Sam’s ass. “Because if I leave it up to Sam, I’ll probably cum just in time for school.”
“Heeeey,” spat Sam, “You love my, nyyyggghhh!”
Wendy slapped his ass, shouting, “Quiet down faggot, you’re a better fuck when you shut up,” Wendy looked back, “So what are you waiting for nerd?”
Oliver wondered if there might be lasting consequences for his actions, what if someone saw them, what if they got arrested, and what if he did hurt Wendy? But none of those reasons seemed to matter after he heard Wendy’s ass cheeks clap. Oliver pulled off his shirt and tossed his pants to the side before kneeling behind Wendy. He pressed his throbbing cock tip against her cunt, slowly pressing his tip past her tight lips.
“Come on Oliver,” Moaned Wendy, “Just shove it in me, I want it so, mmmph bad…”
Oliver’s breathing got heavy, his glasses fogging up slightly as he grabbed Wendy’s hips and thrust his massive meat inside Wendy’s sloppy cunt. “Ahhhggg, fuck yea!” Moaned Wendy, sinking balls deep into Sam’s asshole, “Don’t hold back, fuck me silly with that fat nerd dick!” Cried Wendy as she leaned over and ground her dick inside Sam’s ass, her fat cock head punching his stomach as she laughed, “Ha, don’t think I’ve forgotten about you bitch boy!” Wendy grabbed Sam’s afro and pulled his head back as he drooled, softly moaning as Wendy’s cock pounded him.
“Now keep tight, don’t leave all the work to Oliv-aaaggghh!” A shiver shot up Wendy’s spine causing her to drop Sam’s head. She looked down to see her belly bulging as Oliver slowly pumped her. His cock stretched her up to her womb and scraped her out with each pullback. “Sorry Wendy,” moaned Oliver, “I’ll sto-mmmmpphh!”
Oliver was shut up as he felt Wendy reach behind his head, grab a handful of his dirty blond hair and plant her lips against his. Shutting Oliver up instantly as she tongue punched the back of his throat. “Mmmm, shut the fuck up white boy and fuck me harder!” Mewled Wendy after she pulled her tongue out of Oliver’s mouth, she had a big sultry smile on her face and Oliver tightened his grip on her hips. “Fine, I’ll fuck you until you can’t walk!”
“That’s the whoaaa!” Wendy nearly fell over Sam, her cock bottoming out in her bitch boy’s booty as Oliver started pounding her hard. Wendy’s cunt was being used as a cheap sex sleeve while Oliver’s heavy nuts slapped against her own. “Hooooooly fuuucck,” stuttered Wendy trying to keep balance as Oliver bottomed out in her cunt. Womb penetration was a new sensation and one she’d get addicted to fast. Wendy felt a chain of micro orgasms throb through her cunt as Oliver awkwardly pounded her pussy.
“Gimme more of that nerd dick,” Cried Wendy tears flowing down the corner of her eyes as she mewled, “Fuck the shit out of tight black pussy. It’s all for that fat white nerd dick!”
“You’re so tight Wendy,” panted Oliver, “I’m having trouble keeping up the pace.”
“Come on white boy!” Taunted Wendy moaning as she ground her cock against Sam’s prostate, punching his stomach with her cock tip. “Fucking ruin me, I wanna feel you beat my fucking womb or are you a sissy like this bitch!?”
Oliver’s face tensed up as Wendy slapped Sam’s ass, causing Sam to yelp, “Nyyggghhh!” His pathetic moans edged Oliver into more frantic thrusting. Hearing his bully and crush moan like sluts was making his heart beat faster and faster, his cock pump harder and harder; until his cock throbbed, he rutted in Wendy’s sloppy pussy. Pausing as he muttered in a tense voice, “Wendy I think I’m gonna…”
Wendy turned back, her eyeliner running down her cheeks as she moaned, “Dump it all in me, neeeeerd!” Wendy’s tongue fell out of her mouth as she felt Oliver’s seed bloat her belly. An ultra-thick load that made the few drops that Sam dribbled out onto his chest look pathetic in comparison. Though Sam couldn’t understand that or anything else at the moment. The sissy’s eyes had rolled up into his head and his moans had turned into erratic panting by the time Wendy had busted her own nut inside him. Wendy could feel her pussy throb as Oliver pulled out and fell back onto the mat, letting his load spill out beneath her as he wheezed trying to catch his breath. “Mmmph, that was pretty good for your first time Oliver, I’m in-mmmmmm!” Oliver watched as Wendy squirted on the mat, her gaping cunt spilling out clear juices as her cock flopped out, shooting a few ropes over Sam’s ass. The trio paused for a moment, all of them breathing heavily before Wendy stood up, her knees wobbling for a second, but she remained standing as she turned to look at Oliver. Her cock was half-hard and coated with cum as she said, “Impressive, I’ve never cum that hard.”
Oliver’s eyes went wide as he took a deep inhale, cuming so hard into Wendy it literally took his breath away, but she wasn’t done with him yet. “But are you ready for round two?”
“Wow Wendy, I’d love to but don’t you want a break before…”
“Such a gentleman,” interjected Wendy as she stood over Sam, “But I’ll be taking a break.”
“Then who…”
“I was offering you this bitch boy’s ass.” Wendy placed her foot on Sam’s fat black bubble butt causing his loose asshole to leak more of her thick cock cream as she continued, “He should be loose enough to take your massive white bitch breaker…”
“Bu-but Wendy I don’t want that faggot’s dick!” Groaned Sam.
“Shut up,” responded Wendy, sitting on the back of Sam’s head, smoothing the whiny sissy boy in her thick black cheeks and slapping her fat cock on his back as she continued, “I own your fat sissy ass and I’ll let whoever I want to use this filthy bussy.”
“Mmmmm, yeeeesshh ma’am…” Groaned Sam, his black clitty hard and leaking pre-cum in plain vision of Oliver who wasn’t sure what to say. He wasn’t gay and never really thought of men in a sexual sense before, but something about the way Sam’s fat black cheeks jiggled made Oliver wonder…
“Come on dork,” said Wendy, “This asshole pushed you to the pavement earlier today, acting all fly and cool, but look at him!” Wendy clapped Sam’s cheeks causing him to groan as she spread them for Oliver. A gaping glazed puffy black asshole was on full display, Oliver could see it twitching beside Sam’s clitty as his hole leaked a stream of Wendy’s thick cock cream. “Moaning on the floor from a bit of fat girl dick, imagine how badly he’ll break if you fuck his boi-pussy.”
“Mmmmm,” muttered Oliver, his cock getting hard as he watched Sam’s asshole throb. Wendy took notice and upped her teasing, “Such a timid boy, still need convincing?” Wendy’s voice was almost mockingly provocative as she continued, “If you don’ rape this fat black ass, Sam’s just going to beat you up tomorrow and I might not be around to…”
“Shut the fuck up!” Shouted Oliver and Wendy back straightened up, she never heard Oliver get so loud and it surprised her. “I’m tired of you and this bitch pushing me around!” Oliver jumped behind Sam and pressed his hard cock tip against his ass, sputtering, “If this is the only way to shut this bitch up then I’m going to fuck him stupid!” Wendy cracked a confused smile at Oliver’s silly line, but couldn’t deny the results as he buried his cock to the base in Sam’s ass, causing the sissy boy to squirm under Wendy as Oliver started out pounding. His breathing was feral as his thrusts quickened with each slap of his heavy nuts against Sam’s ass.
“Damn Oliver I wasn’t expecting you to...”
“To what?” Asked Oliver looking up from Sam, “After all that teasing about this faggot beating me up, you expected me to do what exactly? Fucking leave with my tail between my legs?”
“No, I just meant…”
“Well no more!” Spat Oliver as his heavy thrusting got louder. His voice became angrier as he spat, “I’m not going to let this bitch boy make fun of me anymore and if he even thinks of trying to knock me down again I’ll rape his ass in front of the entire scho...Mmmmmph!” Oliver again was interrupted by Wendy kissing him on the lips, stopping his thrusting, and cooling his rage. Oliver closed his eyes, nearly forgetting what he was doing as his tongue entangled with Wendy’s for who knows how long.
“Mmmm, better?” Asked Wendy as she pulled her lips back.
“Yea,” murmured Oliver
“Good,” Wendy leaned in for a hug, squeezing Oliver between her tits as she consoled him. Her voice was soft as she said, “Sorry for teasing you too hard. You fucked me so hard I forgot this was your first time.” Oliver’s face lit up bright red as Wendy ran her hand down her chest, “I was just surprised you started fucking Sam so hard.” Wendy looked down at Sam’s drooling O-face, “Not that he doesn’t deserve a hard fucking. Sam’s a fucking asshole most of the time.”
“Mhhaaaaa, nnnuuuuuh,” mumbled Sam, spitting drool as he tried to object, but failed as his limp clit shot more clear cum onto the mat below. “Hehe, looks like he enjoyed it,” commented Wendy, pointing down at the literal puddle of sissy boy spunk bellow Sam’s twitching clit. “I think you made him cum, like ten times in under a minute.”
Sam let out a giggled moan as Wendy moved off of him and beside Oliver, leaning her head on his shoulder. Which was a little awkward considering the over a foot of height difference, but Oliver still enjoyed it. Her hair was soft and her voice sombre as she said, “I really should’ve stopped Sam this morning, but I’ve gotta keep up this cool girl persona or else I’ll get shit from everyone.”
“It’s okay,” sighed Oliver, “I really should’ve stood up for myself. Though it feels a lot easier now that my cock is buried in his ass.”
“Fucsshhh ooofff fagggoooot!” Drooled Sam, a big smile on his face as he continued, “I won’t take shit from-nnyyggghhh!”
“Shut up Sam and be honest or I won’t fuck you for a year!” Said Wendy.
“Nuuuuuh!”
“Do it or I’ll,” Wendy paused and reached over to her backpack. Letting go of Oliver for a moment to pull out her phone. “Say butt slut!” Cheered Wendy as she snapped a couple of pics of the pair. “I’ll send pics of you being fucked by Oliver to every girl on the cheer team. And you know how much those sluts like to gossip.”
“Mmmm, fine!” Moaned Oliver before looking back at Oliver. His face was a mix of frustration and pleasure as he said, “Your cock feels good, faggaaaaaaat!” Wendy slapped his ass, interjecting, “Say it properly sissy or else.”
“Your fat white cock feels so fucking good, sir!” Screamed Sam, his black clitty throbbing as he screamed, “It’s way better than my little clitty, please continue fucking my fat black ass!”
“Better,” Moaned Wendy, “Now Oliver do you want to keep fucking this fat sissy slut?”
Oliver nodded and Wendy continued, “Good, now let me do something special for my man.” Wendy pulled Oliver out of Sam and got underneath Sam’s body, slipping his legs underneath his pits and shoving Sam’s face into her crotch as she ordered, “Now start sucking sissy or else I’ll torment your clitty.” Wendy flicked Sam’s clit and without pause, he buried Wendy’s fat black cock down his throat before looking up to Oliver. “Don’t worry about Sam, just bury that big white dick into his asshole!” It almost sounded like an order, but Oliver wasn’t about to object. He crawled back behind Sam and pressed his cock into his asshole. He could feel his tight anal walls compress around his dick as he slowly inserted his white meat into his depths.
“Good boy,” whispered Wendy before kissing Oliver’s heavy nutsack. “Mmmmph so heavy, let’s help you empty these full nuts!” Oliver shivered as he felt Wendy slowly suck on his balls starting with the left and moving to the right as his cock sank into Sam’s greedy asshole. His loud boy moans, muffled by Wendy’s cock as they all melded into each other. Oliver could feel his cock leak pre-cum as his sack was gently slurped. Then when he finally buried his dick balls deep in Sam’s ass, Wendy broke her lips off his spit-slicked sack and moaned, “This is the fun part!” Oliver shivered as he felt Wendy grab his ass cheeks, spreading them as he yelped, “Ahhhn, Wendy what are you doing!”
Wendy licked her lips, “Giving you a special service. You should be excited, I've never tried this before…” Oliver instinctively tried to pull out but Wendy kept a vice-like grip on his cheeks and the second he felt her lips tongue his asshole he melted. “Ohhhh, that is… mmmmm!” Oliver’s face tensed up for a second as Wendy’s lips touched his tight white asshole, his lips quivering as Wendy slipped her tongue into his hole, rotating around the inside of his asshole. He could feel his cock oozing in Sam’s tight boi-pussy, so close to cuming, but the vice-like grip his hole was managing to pull combined with Wendy’s teasing kept him on the edge.
“Mmmmm, such a tasty fucking asshole!” Moaned Wendy, licking her moist black lips, “Even better than you dick, Oliver.” Wendy kissed his asshole before continuing, “I might get addicted to this, every day, licking your filthy asshole… mmmmpphh!”
Oliver nearly went limp in Wendy’s grasp as she furiously tongued his fart-box, breaking him down and making his cock ridiculously hard. Sam’s asshole could barely handle it and Sam himself was nearing passing unconsciousness. His eyes rolled up into his head as Wendy’s thick black girl dick stretched his throat out and the second Sam attempted to pull back for air, Wendy’s leg locked him. Forcing his nose directly into her nuts. It was degrading, humiliating, and Sam’s asshole would never recover from the brutal bleaching he was experiencing, but he almost didn’t want to. Sam’s cock was raining cum all over the mat with each throb of Oliver’s cock. The boy he teased almost daily was currently grinding against his prostate, turning it into mush along with Sam’s brain and Sam didn’t think that was so bad.
“Fuck this bitch is throating me hard,” Wendy broke her lips off of Oliver’s asshole, pouting, “He better not like you more than me now…” Before she returned to her eating. Oliver could feel his prostate melt as Wendy’s tongue pressed against it, his cock oozing thick pre-cum like a fountain. Oliver could feel his lust grow, boiling to the surface like a kettle and without warning he erupted. Drenching Sam’s insides in spunk so disgustingly thick it could barely be called a liquid. It clogged Sam’s insides as his little clit squirted over Sam’s tits. Though his cum was quickly diluted by Oliver’s spunk as it spilled from the corners of Sam’s asshole. While Oliver’s asshole received a merciless tonguing as Wendy dumped her own, hole clogging load inside Sam’s throat. Sam could swear the pair’s hot cum met in his stomach, bloating him as he came his brains away.
Wendy was the first to speak, breaking her lips off of Oliver’s spit slick hole before moaning, “Whoooa, that was something...” Wendy’s gip eased on Oliver’s tight white cheeks and she fell back on the mat mumbling, “I came soooo fucking hard, how bout you Oli?”
“I… I…” stuttered Oliver, “I think I’m gonna collapse.” He fell back missing Wendy’s head, but the torrent of nut sludge did not. Wendy got a surprise facial as a large glob of cum jettisoned out of Sam’s gaping asshole onto her face, messing her long black hair, and staining her cheek as she sighed, “You’re lucky I like your cum.” Wendy pushed Sam to the side rather easily, considering he was in a cum-comma, softly mewling as spunk leaked from both ends.
“Will he be okay?” Asked Oliver.
Wendy looked back at trembling Sam and shrugged, “Probably, I’ve done much worse to him.” Wendy scraped the cum from her face, swallowing a thick glob before moaning, “But I think you’ve fucked him the deepest.” Wendy cleaned her face up, scraping the rest of Oliver’s load into her gullet as Oliver sat, panting, trying to catch his breath. “Incredible,” he muttered under his breath as Wendy crawled up to him. Oliver embraced her and she did the same, wrapping her arms around him, their sweaty bodies pressing against each other for a good few moments; until, Oliver said, “Wait I have something for you.” Wendy looked up at him partially confused as Oliver crawled over to his satchel and pulled out a small portable chess set; small enough to fit in a sweater pocket. “Here,” Oliver presented the set to Wendy, “I got this for you after the tournament. In case you wanted to play sometime?”
The room was silent for a moment, Wendy just stared at him wide-eyed before grabbing the board. “See all you have to do is fold it open and all the pieces are inside this little cubby. It’s very portable and…” Oliver paused as Wendy gave him a pec on the cheek, stunning Oliver before she said, “Thanks,” and Oliver could swear he saw Wendy get shy, but it wasn’t meant to last. In about two seconds she was already on top of him, her thick black cock pressing against his white one as she asked, “I’m going to ride your dick all fucking night white bo…”
Before Wendy could say another word, the piercing sound of a high-pitched musical tune cut through the lustful atmosphere, breaking the pair’s focus in an instant as Oliver muttered, “Sorry it’s my phone.” Oliver reached into his back and pulled out his Samsung and immediately after answering he heard the shrill voice of his mother scream, “WHERE THE FUCK ARE YOU YOUNG MAN IVE BEEN WORRIED SICK ABOUT YOUANDONCEYOUGETHOMEYOUBETTER… Click.” Oliver sighed and looked up at Wendy who was still over top of him.
“I’m sorry but I’ve got to…”
“Yea I heard,” pouted Wendy stepping off of Oliver. She sighed, “Well it seems like I can’t hog you all night, but don’t worry I’ll clean up here.”
“Thanks Wendy,” said Oliver, quickly shoving his clothes back on. “But you didn’t answer my question, did you want to play sometime?”
Wendy slid her skirt back on (which did a surprisingly good job at hiding her meat), saying, “Hmmm I’ll give you my full answer tomorrow.” Wendy made a shooing motion, “Now get out of here quickly before I tackle you down, again.”
Oliver wasn’t sure if he should be aroused or terrified (he was both), but he quickly re-dressed and exited the school grounds. Moving a full sprinting speed to try to get home and avoid the full wrath of his parents.
Epilogue
Oliver got an earful from his parents when he arrived home at one a.m this morning and he barely got any sleep after being grounded for a month; yet, he still felt amazing. He hadn’t seen Sam all day or seen him for that matter, same with Wendy. Oliver thought it was strange, but assumed nothing was amiss until he started walking home, taking the shortcut across the track field, but just as he was about to round the bleachers he felt a hand grab him and pull him behind.
“Hey dork, I was begging to think you weren’t going to show up.” It was Wendy standing beside a rather embarrassed-looking Sam, who averted his eyes as she pulled Oliver in for a hug. “Wendy,” Oliver’s voice perked up immediately, “I thought it was weird when I didn’t see you at school.”
“Ahh, how sweet worrying about me, but I was only playing hooky.” Wendy smiled as Oliver took a step back. The pair were both dressed pretty standardly, Wendy in a crop top, slacks, and a blue letterman jacket, and Sam wearing his normal baggy apparel. “But that’s not the point,” continued Wendy smiling, “The point is we got a little surprise for you.”
Oliver smiled, overjoyed she was thinking of him and he asked, “You didn’t have to reciprocate my gift Wendy and you certainly didn’t need to skip...”
“We did,” interjected Wendy, “Now shut up and take a look at these!” Wendy pulled down her skirt slightly, revealing the base of her cock and a tattoo, right above her dick; a pure white heart about the size of your palm and a red ‘Q’ in the center. Wendy peered over to Sam who was looking away hands in his hoodie pockets, and nudged him with her elbow spitting, “Hey faggot, you have to show off too!”
A woozy smile crept across Sam’s face as he pulled up his hood, revealing a matching jack of hearts tattoo, “I’ve decided to stop teasing you faggot, but only if you keep pounding me with your cock…” Sam turned away, and Oliver wasn’t sure what to say, but Wendy continued, “You’ve convinced me to be your girlfriend and despite his initial unwillingness, bitch boy is completely addicted to you too.” Sam gave Wendy an annoyed look and she responded, “What? Like an hour after he fucked your fat black ass you switched your phone's wallpaper to his cock.”
Sam’s face scrunched up as he blushed, causing Wendy to laugh as she looked over to Oliver who was blushing, “This bitch boy has white fever and you know what,” Wendy walked up to Oliver before planting a kiss on his lips. Oliver could feel himself get woozy as she nearly sucked the air out of his lungs. Their tongues pressed against each other for just a moment before she pulled back moaning, “Mmmm and I do too.”
“Wow Wendy,” Oliver could feel his cock harden as Wendy’s hand rubbed up against his bulge, “I don’t know what to say.”
“Don’t say anything,” Wendy stepped back and pulled down her pants before leaning on the support beams and looking back, “Just pick one of us and start pounding. I’ve been feeling horny all fucking day.” Sam gave Oliver a nervous smile and did the same, spreading his fat black bubble butt for him. Oliver’s heart was beating so fast, but he naturally knew what to do, quickly pulling down his pants and thrusting into Wendy. She groaned in pleasure, her fat black futa cock throbbing as Sam meekly watched. “I won’t leave you alone sissy,” said Oliver as he began to finger Sam’s loose asshole.
The sissy squirmed and moaned, “Nyyyggghh,” as Oliver teased, “I’ll make sure to give my new girlfriends all the love they need.” Oliver slid another finger into Sam’s tight black asshole as his pumping intensified, “And I’ll make sure to give you my dick every day Sam. I like you a lot better when you’re behaving.” Sam groaned as Oliver scrapped out Wendy’s asshole, Oliver never felt so good and hoped this moment would never end.