I don't do a lot of mixed matches, but this was an old idea I liked as a close and interesting thought. 3 teenager boys against a fit local champion of a woman. And don't forget to check out my Hentaifoundry and Patreons for more fics and artwork.
Viewed from the outside, Appleoak was a small and cozy neighborhood out in Kansas. They were a fair drive away from anything of real interest, so that left to making their own fun. The latest trend to really take off was backyard wrestling; everyone from the kids to some of the grandparents participated, though the young and the strong obviously dominated the ring. Over the last month or so, Dana Madison had taken an obvious lead in the ranks. The fit single woman was an absolute powerhouse in the ring, throwing around grown men as easily as she did the housewives. Even when some of the neighbors rushed in for some disqualifying payback, Dana was known to bounce back and beat down both of her opponents at once! Nobody had beaten her ever since she got her hands on the championship belt (a plastic one they bought from WalMart, but still a title). People were starting to talk if she would simply go pro and look into actual wrestling leagues.
Despite being in the later end of her 30s, Dana had a build that obviously hit the gym. She had plenty of bulge to her thighs and biceps without bulking up too much of her body. She was tall and on the slim side, but her toned core and powerful limbs made her a devastating opponent. She had shoulder-length black hair and fair skin despite how much time she spent out in the ring or working out. Her black and purple sports bra and underwear with some dark violet leggings made up her standard ring attire, and today was no different. It wasn't a proper title match, or even any referee to witness it. This was a personal challenge, and she wanted to see if she could do it as much as anybody else.
The boys in the neighborhood knew that they had no chance at beating her. It was a common joke that the boys who challenged her were just looking for an excuse to get between the cougar's thighs. Sure, they usually got choked out in a scissor down there, but they could return bragging that they'd touched the foxy champion's boob. Milo, Charlie and Luke had put their heads together and come up with a strategy of their own and appealed to Dana's pride; she accepted the highly handicapped challenge, and even with so many things in their favor, they still had to stifle their worries that the match would turn against them.
The boys arrived at Dana's house in their street clothes. She was one of the families who had installed a full wrestling ring in her backyard to accommodate the matches, calling it a "home turf advantage." She let the boys in, wearing a loose tank top and sweatpants. She peeled them off in front of them, showing she was already in her ring attire and walking confidently ahead of them. The boys had to stare, and she knew it as she smiled to herself. It had done wonders for her confidence ever since she started participating in these matches. The idea of beating all three of them in a row gave her an entirely new shiver down her spine. As much as she loved to win and show off, there was always a higher mountain.
They went over the rules again as she climbed into the ring. They would each fight her one at a time in any order they wished with a 2 minute break in between matches. As a further handicap, they had each picked out a single foreign object to use at their leisure. Charlie had the garbage bag over his shoulder, concealing what they had picked. Dana could still hear the faint metallic clang of them inside, giving her some hint of what they had in store. She was banned from using the weapons on the boys herself, and any match was over if either one ended up unconscious, tapped out, or was fully pinned for five seconds.
"And the loser does whatever the winner wants!" Luke had added at the last minute. "For a week!"
"Fine," Dana had agreed, watching the nervously approaching boys with a smirk. "For a week. I hope you boys like doing yardwork, because I've been meaning to get that garden going for months now."
The three teenagers huddled up while Dana climbed into the ring. "Okay, guys. Remember the plan," Luke advised. He had been the brains from the start, the one to come up with the idea before letting Milo pitch it to Dana. He had short, dark curls to top off his lean and lanky body.
"Right," Charlie said with a nod. "We can't actually win, so use the weapons all the time." He was the heaviest of the group, making them effectively their muscle. He was definitely on the fat side with some shaggy red hair and patchy freckles on his face.
"Jeez, Charlie. This is why you're going first," Milo groaned, the charmer of the three. He'd weaseled his way into some slippery tactics to win his matches, a quick thinker and dirty fighter compared to Luke's actual planning. He had a steady tan to go with his mixed heritage and some long, smooth brown hair. "Wear her out, hit with the objects, but don't overuse them or she'll see it coming. She's not a meathead like you."
"Hey, we'll see who's the meathead when I beat her in round one," Charlie defended.
"It's you," Milo answered for them. "Definitely you. You will be the meathead because you even thought that was possible. Just do all you can before she takes you out."
"Thanks for the confidence," Charlie scoffed.
"You boys going to keep playing truth or dare over there or are you going to come get your asses kicked?" Dana called over their huddle. They patted Charlie on the back as the redheaded boy climbed into the ring wearing his t-shirt and swim trunks. He reached into the garbage bag and took out a folding chair before dropping it out of the ring. "A classic," Dana observed out loud. "But I've taken plenty of chair shots in my time."
"We'll see how you handle this one," Charlie huffed as he set the chair up in the corner. Luke clapped his hands sharply.
"Okay! Start it up!" he declared. Charlie tried to walk right towards the cougar but she smirked and sidestepped him casually, circling the ring to keep him chasing after her.
"She's messing with him already," Luke sighed, shaking his head at the scene.
"She's still fresh. It means she's cocky," Milo pointed out. "It means she could mess up. Especially once she's done tossing around Big Charlie."
Charlie finally broke into a run as he rushed at Dana, grabbing for her midsection. The brunette caught his hands and the two quickly started pushing at each other as they locked up in a proper grapple. Charlie had a decent push to start, but Dana planted her feet and started to overpower the redhead. He grunted and tried to jerk around to break free from her relentless force, but she had him locked in now that she had him by the hands. Her muscles started to bulge as she overpowered the strongest of the boys, powering into him until Charlie was stumbling backward to keep from falling over. With a dull clatter, he reached his original corner and his knee caught the seat of the chair, falling noisily into the unfolded seat.
Dana laughed at his humiliating position as Luke spoke up quickly. "Hey, you can't use the weapons!" he protested. Dana flashed him a smile as she let go of Charlie and backed up.
"Don't worry. I just thought he could use a break," she said, flexing her arms and kissing her bicep. "I want to be nice and ready for all three of you boys. Just wait your turn."
She went back to Charlie as he shook out his aching hands, grabbing him by a fistful of hair. Charlie winced as he stumbled to his feet, though making Dana work to lift up the hefty young man. Just when she got them both mostly upright, Charlie threw himself back and pulled on her hair in return. Dana tripped forward with him, landing on her knees as he pulled her head past him and banged her forehead off the top of the chair.
Dana’s head bounced roughly as she fell off Charlie and onto the mats, clutching her forehead with her mouth agape. The rest of the boys gave a triumphant cheer as their bigger bro hurried to his knees, throwing himself on top of the muscular cougar. He sent a few heavy punches towards her face but she already had her hands up, making blocking them an easy task. While Dana turtled up to protect herself, Charlie went ahead with the plan. Her hands were too busy to block anywhere else, so he rose slightly off the mats and brought his heavy knee crashing down on her abs.
“UMFF!” Dana’s body flexed to absorb some of the impact, but her body still flopped and thumped noisily on the mats. She clumsily tried to block both her head and stomach, but Charlie just went between the two. He grabbed her sports bra and pulled it high up near her neck. The boys flipped out again as Dana’s pale, slightly upturned breasts were exposed, hard nipples and all.
Charlie stayed on his knees, maneuvering around Dana to crouch behind her. The cougar had been topless in a match before, but the heavy boy pulled on her sports bra to loop it around her throat like an elastic noose. The older woman gasped as he tried to lock in the choke, twisting her garment around to close it around her neck. Her face started to go red but she had stayed the champion between her level head and strong body. She drove an elbow back into Charlie’s side, making the big boy jiggle and grunt. She adjusted her aim a little and pounded him with a few more, softening up his ribs before he finally retreated. Dana pulled off and threw away her bra, deciding that a little embarrassment was better than risking another choke.
Milo reached into the ring and nudged the folding chair closer to them. Charlie caught sight of it and as Dana started to drag herself up, he caught the chair and rammed one of its hard legs into her midsection. Dana huffed again as her aching abs tried to soak the hit, doubling over in front of him.
“Looks like I won’t need your help, guys,” Charlie boasted as he swung the chair like a broad club. It crashed into Dana again, but she brought her forearms up to absorb most of the impact. A quick shove threw the weapon aside, and Charlie had a split second to register what had happened before her forearm slammed him in the balls.
Charlie gave a noisy groan, bending over and going right into Dana’s grip. She caught him in a front headlock as she drove some punches into his soft sides, softening him up even further. His teammates outside the ring winced as she had him right where she wanted him, turning and running across the ring to slam his face into the farthest turnbuckle at top speed. The big lug landed on his back, seeing stars despite the sunny day overhead. He barely noticed Dana looping her legs over his shoulders, but he certainly felt it when she locked them in place and squeezed around his neck. Her flexing thighs put a lot of pressure around his head, turning him red within seconds as he gagged and pulled on her iron legs. He’d longingly talked about being stuck between the legs of the topless champion, but it was suddenly a lot less fun when he was actually there. Not that it was all bad really… he groped at her full breasts with his last breaths before he fell limply into her lap.
Dana lifted and dropped one of his motionless arms before she opened up her legs again.
“Alright. He’s definitely out. Which one of you boys is next?”
Milo and Luke shared wary glances. Dana was a little softened up, but she certainly didn’t look like she was easy pickings. Luke finally sighed and slid into the ring.
“I might as well,” he decided as Milo dragged Charlie out of the ring. “Just make sure you pull my corpse out too, bro.”
“Love the optimism. Very attractive,” Dana joked as she stood confidently despite her lost top. She clocked how Luke inevitably eyed them up before focusing on her face again.
Dana moved in swiftly and grabbed the young man. She didn’t want him forming any kind of strategy when she knew she had a huge advantage in size and strength. Luke tried to squirm away but she quickly caught him under one arm and yanked him into a headlock. He took a quick gasp of air before she clamped a muscled arm around his neck, mashing his face against the side of her breast.
“Don’t worry. I won’t go too hard on you boys. I need you healthy enough to do my yard work after all,” she gloated as she dragged him away from the ropes. He was left doubled over in the ring, completely at her mercy in the tight hold. He wasn’t going anywhere as long as she kept her grip.
Unfortunately for Dana, he was counting on that. He shifted his head just enough to bite down on her tit, making her scream as he managed to catch the very edge of her nipple between his teeth.
“AGHHH! You little monster!” Dana howled as she writhed in place. She didn’t want to lose her crushing grip, but the intimate pain was too intense to ignore. She twisted and bent to try to pull herself from his mouth but she couldn’t have both. She released one arm to grab him by the hair and pull back on it, getting Luke to wince and gasp hard enough to let go.
“Little fucker,” she hissed as she kept his head turned away from her. She drove a knee up to slug him in the stomach, knocking more wind out of the breathless boy. He clutched at his stomach, but it was a good enough excuse to grab at his one weapon of the match.
He clutched the flat brass knuckle from the pocket of his trunks and wasted no time in driving it up between the cougar’s legs. Dana let out another cry of agony, this one much more guttural than the sting of her tits being bitten. Her feet bounced off the mats for a moment as she let him go to grab at her privates.
“Hell yea, dude!” Milo cheered at ringside as the champ was left devastated.
Luke rubbed his neck briefly before he grabbed Dana by the hair. He kept up his attack as quickly as he could, pivoting her and throwing her into the ropes. Dana crashed into the nearby turnbuckle, emitting a low groan as her bare chest hit the ringpost. She was still too busy holding her pussy to fully react, leaning draped over the top ropes. That was fine with Luke as he ran in and drove a few knees into her back, getting her to buck and moan as her tits wobbled and her face strained for Milo’s amusement.
Luke grabbed her by the hair to crash her head into the ringpost’s steel, but she snapped out of her haze of agony long enough to slam an elbow back into his ribs. He grunted as he was cut off, letting her size up their position and sweep her leg under his. Luke fell right on his ass as Dana rubbed her back and turned to glare at him.
“Never mind on the not too hard part,” she threatened as she threw a kick into his chest. Luke grunted as he went flopping back, tumbling away and trying to crawl back to regroup.
Dana caught him by the leg before he got very far. She dragged him back towards her and looped her legs around his. He could feel her long and sexy limbs tighten as they clamped his at an awkward angle, bending them in a figure four leg lock. He let out a shrill scream as the hold that had ended matches for her was locked in.
“You’re okay doing my chores in a wheelchair, right?” Dana hissed bitterly. She wasn’t going as hard as she could on the leg lock, trying to go easy on herself after the low blow, but Luke was scrawny enough that making him tap out didn’t seem too hard. She could see him struggling with the pain and prying at her legs desperately enough already.
Or rather, he was positioning her so that he could hold her leg in place and slam his knuckler into the side of her knee. The quick-thinking boy got her howling again, and he kept up the pressure. By a third and fourth blow, Dana was breaking the hold and crawling away clutching her leg. Definitely not broken, but it still hurt like hell.
She shifted up to her knees, leaning on the ropes and nursing her damaged leg. She could still stand but she was giving it a moment’s rest, and a moment was all Luke needed. The scheming boy rushed her and she barely caught his wrist before he could slug her in the face. She slammed him with a quick forearm to the head, but he briefly reeled before he snapped a kick into her bag leg. She gasped and bent over to grab at it, just for Luke to grab her hair and drop to the mats. He brought her crashing face first towards the ring, but with the added twist that she was flying right into Charlie’s abandoned chair from earlier. There was a tinny crashing sound as her head hit the lightweight metal, making her flop theatrically as she laid face down and reeling.
“See? You can outsmart anybody once you know the right weak spots,” Luke panted breathlessly. “Or if you make your own.”
He had gotten some major hits in, but his lack of strength and stamina were showing. He took a few seconds to roll Dana over and tossed himself onto her for a pin. Milo gladly rushed over to slap the mats, barely getting a three-count when the cougar bucked up a shoulder. Luke cursed under his breath and went for her hair to drag her back up, but she wasn’t as vulnerable as he’d hoped.
Dana thrust an arm between his legs and rose up, lifting him with her in a feat of strength before bodyslamming him back down. The scrawny boy grunted noisily and flopped as best he could with her tits bouncing on his face.
“Say goodnight, you little brat,” Dana huffed, particularly fed up with his tricks. She forced his knucklers off and threw them out of the ring as she went to finish him. She moved up enough to sit on his chest and lift up one of his legs, putting as much weight on his shoulders as she could. She started to slap the mats for her own count, and Luke was down for four of the five seconds before she was cut off again.
Dana shrieked as Luke’s hand found itself between her legs once again. Her tight leggings left it easy for him to find her crotch again and dig in with his fingers, locking into a cxnt claw. He even scratched and pulled enough to tear open a chunk of the fabric and gouge right at her pussy lips, making her moan and shudder feebly.
“Weak spots, remember?” Luke grunted wearily. He twisted and pulled at her twat enough for him to wriggle out from beneath her, locking himself in behind her. He kept his death grip on her pussy going, trying to do enough damage to get her to surrender. Dana grit her teeth as tears welled up in her face, but he wasn’t the only one to play this dirty with the champ before.
She pawed at his thighs for balance, bracing herself before she threw her head back. A firm headbutt rattled Luke enough for his grip to loosen a little, so she slammed him with a couple more. He slumped weakly against her back after that, his hand laying limply in her lap. Dana didn’t want to risk him pulling any more surprises so she grabbed his legs and sat up, letting him hang in her grip. She gave a quick spin in place before hurling him like a hammer toss, letting the lanky boy crash land back on the mats a few feet off. He landed like a rag doll as Dana planted her hands on his chest, panting and nearly-naked over him as she slapped out the five-count.
“Done,” she insisted breathlessly.
She gave Luke a firm shove to roll him out of her ring. She stood up and shook her head, tossing beads of sweat from her skin and hair. It made her muscles glisten as she looked to Milo, her final opponent. She glanced down at herself and the large tear in the crotch of her outfit, deciding it wasn’t worth keeping on. She grabbed and tore them open in the middle, feeling a bit like The Hulk as the remaining boy stared wide-eyed at the show of strength and sexuality. She stood naked in the ring and gestured invitingly at him.
“Come on, little man. I’m 2 for 2. Let’s fucking do this.”
Milo was certainly intimidated, but the tan boy still slid into the ring. He wasn’t as strong as Charlie or crafty as Luke, but he hoped they’d used their specialties to ensure his victory.
Milo climbed in warily, making sure the fired-up brunette wasn’t about to decimate him before he could even get into the ring. He approached her cautiously before he took a sudden swing at her. Dana tried but failed to block his quick punch as it cracked across her face, sending her head reeling. She shook her head out, giving Milo a small spark of hope to see she was this worn out already.
He drove a couple more quick punches into her chest, bouncing her bruising tits around while making sure she didn’t get a grip on him. Dana looked exhausted as he took his potshots but she kept stalking after him slow and steady.
Dana lashed out at him and caught one of his arms, making him instantly turn desperate. He swung a kick at her crotch but she had been expecting it all along. Her other hand swung in and caught it, leaving him hopping awkwardly on one foot.
“Fucked up, kiddo,” she scolded with a vicious grin. She lifted him up and body slammed him back down, planting her firm naked body down on top of him. Milo groaned loudly as he was crushed beneath the strongest and hottest woman in town and couldn’t properly enjoy it as the wind was knocked out of him. He shoved and scrambled feebly, in a bit of a daze himself as she dragged him back up.
“Don’t think so, bitch,” she hissed as she placed him in front of her, wrapping her arms around his waist. His tits rubbed on his back and neck before she swung herself over backward, suplexing Milo over her head and into the mats. He let out another sharp “AW!” as he bounced out of her grip, already down and hurting on the mats. The sweaty cougar wiped the sweat from her forehead as she grabbed his limp arm to drag him back up.
“Come on… I’m not letting you off that easy,” she huffed as she propped him up in front of her. He couldn’t wriggle free fast enough in his sluggish pain as she hugged him around the middle. She leaned back and lifted him in a bearhug as his feet kicked around wildly. It was a mocking consolation as her crotch rubbed up against his through his trunks, but he slapped and shoved at her chest to no avail. Her powerful grip was crushing his already beaten body.
Dana cracked a sadistic smile. She was glad to put the cheating boys in their place for trying to think their weapons and numbers could outdo her skill and strength. She was the queen of the neighborhood league and this would make it clearer than ever. She was hoping in the back of her mind that Milo had forgotten his weapon in the heat of the moment, or at least left unable to use it in her largely one-sided beating.
Trapped in the bearhug, Milo saw his moment. She was unable to dodge with her hold locked in, so he pulled the fistful of powder from his pocket. Luke had left him with it before the fight, telling him to be sure it would hit her in the face whenever he used it. He held up the handful and blew it into her eyes, the burning mix of chili powder blasting her in the face.
The heat made her eyes water immediately. Dana screamed madly as she let go of him to rub at her face, but it only helped smear the blinding substance around. She dropped Milo and he immediately threw a simple but very effective kick into her pussy. A fresh scream escaped the blinded cougar as she dropped to her knees, breaking into sobs as her eyes and pussy throbbed in agony.
“Oh my god! You… you little fucking bitch!” she shrieked.
Dana brought a hand away from her face long enough to paw around her, but Milo had wisely gotten well out of reach by then. He circled around her and timed it out where he could swing a roundhouse kick to the back of her head, sending the pained and confused champ dropping to the mat. He quickly went after her to capitalize as he stomped around her head, back, and particularly her injured leg, leaving her screaming and thrashing in helpless pain beneath him.
Milo gasped as she suddenly grabbed one of his ankles, tearing it out from under him. He tripped and fell on his ass as Dana rubbed what tears from her face she could, her red-stained eyes trying to glare at him.
“You are dead, you little shit,” she hissed as she crawled after him.
Milo slammed a desperate kick into her chest and backed away, crab-walking towards the edge of the ring. Dana snarled and rose unsteadily to her feet, charging at the blurry pink blob that Milo looked like to her. He was still on high alert at her sudden struggling, running off to one side. Dana’s vision was still blurry enough that she missed his dodge and crashed right into the ringpost behind him, grunting in shocked pain at the impact. It was becoming more clear to Milo that he’d have been slaughtered if she had fought him fairly, but against a blind champ he had a decent shot.
He grabbed Charlie’s chair from earlier and rushed at her from behind. Dana was feeling around the ropes to understand what happened when the metal crashed into the back of her head, making her shiver and drop limply against the ropes. Milo hurried to grab her hair and shove her head through the bottom and middle ropes, leaving the naked champ helpless as he pressed his knee on the back of her neck. She wheezed and gagged loudly as her throat was crushed on the ropes, choking out what little fight she had left in her. Her already red face only got redder as she thrashed and drooled pathetically halfway out of the ring. Milo even shifted off her of her to grab her hair, pushing on her head by hand so he could grind his raging hardon against her upturned ass.
Giving her a final spank, Milo stepped back and threw her down on the mats. Dana groaned in a completely dazed and helpless state, but still propped an arm under her. She forced herself to almost sit up when Milo went back into his pocket. He threw a fresh handful of the last of his powder into her face, unleashing a fresh hell on Dana’s face. The muscular champ screamed anew and writhed on the mats as Milo went to finish the job.
He climbed the nearby ropes, steadying himself to make sure he was ready to turn and land a flying splash on her. His back was turned when Dana focused through her pain long enough to hear his creaking climb, stumbling up to her feet and kicking the pole with all her might. It made the ropes and ring rattle, and Milo lost his footing to call nuts first onto the top turnbuckle. He choked on a gasp as he clutched his crotch. He wasn’t as decimated as Dana was, but he also lacked her tolerance for pain.
Dana followed his pained groans and started to feel around for him when she suddenly fell over. She was much too blind to see what had happened, and even Milo hadn’t noticed Charlie and Luke coming back from unconsciousness. They’d each grabbed a leg on the champ and nodded to each other, pulling hard to smash her crotch-first into the base of the ringpost.
“AWWWW!” Dana wailed in pain as she tried to grab her pussy, unable to realize there was any cheating going on to call them out. Luke signaled hurriedly to Milo, who forced himself to rise despite the pain in his crotch. He jumped and brought his heels down on the vulnerable Dana’s belly, crushing her tight abs and sending a loud, wet gag from her lips. Her face was frozen in a drooling, crying mess as her head flopped limply over, looking out cold if not for the occasional twitch.
Milo didn’t take any chances. He sat down with his knees on her shoulders and crotch in her face, resting his balls on her mouth with nothing but his trunks between them. Even at a fair pace, their 5-count was assured as the devastated cougar was finally pinned.
“Yea! Only had to ch-” Charlie started before Luke shushed him just in case.
“Shut it. This was Milo’s win, right?” he insisted in case Dana was awake enough to listen but not enough to move.
Luke went over and snapped a picture for proof, making sure to save the date and time. He considered whether or not to send it to the league’s private facebook group, but decided just to hang onto it for now.
“Oh man, we can make her do anything!” Charlie celebrated. “Like fuck her and make her lose matches or give us the belt…”
“True. But… it was Milo’s win that did it. He should get to decide first,” Luke repeated.
The breathless boy nodded as he caught their leader’s eye. He slid out of his trunks and rested his cock and balls on the ruined champ’s face. Precum leaked over her battered but lovely face as he stuffed his dick into her mouth, facefucking her into the mats. She groaned and gurgled mindlessly, but seemed aware enough to close her mouth and sloppily suck him off. He’d never felt such relief in all his life.
Dana would ultimately wake up just in time for Milo to shoot his load into her face and mouth. It was the first of many orgasms she was forced to give the victorious boys, waking her up from her painful daze like a humiliating slap in the face to what had happened.
