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Chapter 20
by
Raljo
What's next?
Karen cheats
Karen was exhausted. Billy could tell, the other moms watching could tell… The only one in denial about it was Karen herself.
She was a decently fit woman, but even this much “fighting” was exhausting for any untrained middle aged woman. Her body glistened with small beads of sweat under the gym lights, her breath coming heavy and ragged, her gorgeous face slightly red in the cheeks as she glared hatefully at Billy.
God, she fucking hated that brat. She’d been putting everything she had into all of her wild, missed punches - meaning a lot of energy, but no technique. She just wanted him knocked out already. That cocky young athletic prick.
Karen wasn’t used to all of this physical exertion. That much was obvious. So when she stepped forward to throw yet another punch at Billy, it was plainly telegraphed, and slow as molasses. Thrown with that same wild, untrained, techniqueless form, guaranteeing that her balance was offset immediately, and that there wasn’t any real power behind it anyway. This irritable milf had no clue what to do with herself in an actual fight.
As usual, her attack was directed straight at Billy’s face - like every amateur, she was headhunting hard. Not even consciously realizing that hits to the body were a possibility. Just **** to land something and knock Billy out.
But it wasn’t going to happen. That lucky punch earlier, she had unintentionally put the strength of her legs and hips behind it. She had been standing still, after all - but ever since stepping into the boxing ring, Karen had only been throwing by swinging her arms as she advanced forwards. She wasn’t a threat. She was just embarrassing herself.
“Fuck you!” Karen spat as Billy easily moved out of the way again.
Billy shifted his body so that Karen’s follow-up punch was only a near miss. He wasn’t jumping back far anymore - his confidence was returning, and he didn’t want to tire himself out too quickly. Besides, even with his chin 100% compromised, Karen could probably hit him ten times flush with this nooby technique before he actually got woozy.
Billy replied with a quick double-jab of his own, making Karen stumble back into the corner again.
As much as he wanted to knock her the fuck out for being such a bitch, and for humiliating him with that one-punch KO earlier, he knew that wasn’t the smart decision. He was taking this fight to show the other moms that their daughters SHOULD join the boxing club. Brutality wouldn’t accomplish that. It would only scare them off.
Billy would just have to make his fun by tiring Karen out, and making her look stupid all fight. That was good enough for him. And she was looking pretty exhausted already.
Karen brought one of her gloves up to her face, gently holding it and glaring daggers at Billy from over the glove. A few snickers from the observing moms pushed Karen over the edge. She wouldn’t be made a fool of like this. She couldn’t bear it!
Who the fuck did Billy think he was? Smug fucking prick. Him and his whole perfect fucking family. He needed to learn his place.
“You fucker! You BRAT!”
In a rage, Karen rushed forwards and thrust her glove out towards Billy again. Slow as hell and without any true power, despite the massive energy investment, as usual.
This time, Billy didn’t even need to dodge. Karen’s glove missed his head by miles. At first, Billy thought that all Karen’s anger was just making her worse. Sloppier. Hit was too late when he realized that she hadn’t been trying to punch him that time.
“Ghnng!” Billy grunted in surprise, as Karen wrapped her arm around his neck and pulled him in. She had thrown her fist past him on purpose.
Billy was taken off guard. His first reaction was to twist away from her - it was the wrong reaction. Now behind him, Karen easily pulled him into a ****, just like she’d wanted.
Billy stumbled backwards with the guidance of Karen’s arm as she pressed herself against him. All of a sudden, he was in danger. This bitch had become a real threat, just as he was starting to relax. Fuck!
Billy tried to **** himself out by leaning forwards with all his strength, but the milf had him trapped and progress was slow. The squeeze she had on his neck was too good to break out of with sheer ****, at least not quickly. He was in serious danger of being choked out by this bitchy milf.
Karen hadn’t made it far out of the corner, and now that she had Billy’s back, she quickly walked them right back into it again before Billy could pull himself free. When she got there, she leaned back into it at an angle - supporting their weight with her upper back pressed against the padded ring post, but keeping them both leaning back at a steep angle, so that Billy’s balance was offset. He couldn’t brute **** his way out of this anymore. All the while, her sleek forearm had a deep **** locked in. Squeezing Billy’s neck in her milfy, untrained arm.
Billy was in shock. He tried to shake himself loose, but he couldn’t. Karen was growling into his ear, her sweaty sports bra-covered breasts squishing up against his athletic back. He could hear her hot, heavy breathing, and feel it on his face. Her arm was locked tightly around his neck, wrist held in place by the crook of her other arm’s elbow - a perfect rear naked ****, in boxing gloves.
Billy hadn’t gotten a chance to explain the rules yet - none of the moms knew that what Karen was doing wasn’t technically allowed. Truth be told, even Karen didn’t realize she was cheating - not that she would have cared if she did know. She just wanted this fucking prick down on the mat.
“You want a fight, you BRAT?!?” Karen growled, pulling him back further, pressing her soft breasts up against him even more. She knew this was her only chance to win this.
At the angle Karen was holding him, Billy couldn’t get his feet underneath him properly. Leaning back and held as low as he was, he just couldn’t generate enough strength to break out with just the **** of his legs - the angle was too weird. Even trying it, leaning forwards to pull away with just his neck muscles, only tightened the bitch’s **** for her.
Worse, because of his big, stupid boxing gloves, he couldn’t even get a grip on her arm to break her chokehold with his hands. Panicking, and with little else to do, the confident young man just started flailing his limbs around pathetically. **** for a way out of this bitch’s cheating chokehold.
“S-Stop! This is against the rules! This is- ghk!” Billy’s **** pleas were cut off by Karen **** him even tighter. From his back, a wide grin spread across her face. Holy shit - this was working. He couldn’t get out.
Billy began gasping, throwing his arms around more desperately in a total panic. A second wind rushed through the bitchy queen bee milf as she saw his reaction. Invigorated by how red in the face he was getting, Karen redoubled her efforts, squeezing with everything she had. Energized and ready to **** this brat the fuck to sleep.
Billy kept wriggling around as much as he could. Struggling desperately. But he couldn’t break free.
“Come on! Brat! Come on!” Karen laughed, twisting him from side to side as she choked him, to keep him unbalanced. Rocking him to sleep.
His face was getting redder. Drool collecting around his lips. In awe, the crowd of moms gathered around that corner of the ring, watching him struggle against Karen’s tight hold. Watching him slow down.
“Oh my goodness… Is Billy going to lose?” an observing mom gasped.
And he was. He was being squashed like a bug. He was being humiliated. Somehow, that bitch Karen had found a way… And now he was being choked ****, while he swung those stupid boxing gloves around wildly. Looking even stupider, even weaker, than Karen’s nooby milf punches from earlier.
In his desperation, with his vision fading, Billy suddenly realized that he needed his hands free. Maybe then he could get a good grip and pull Karen’s **** away.
With only moments of consciousness left, Billy hastily brought one boxing glove up to his mouth and tore open the velcro strap, shaking the glove off and letting it drop into the ring. His body began twitching and shaking, as his vision grew even darker.
Billy brought his naked hand up to rest weakly on Karen’s forearm. Body twitching madly, and limbs heavy, he slowly brought his other shaking arm up to his mouth. He was barely able to tear open the velcro strap with his teeth before a large, violent shudder ran through his body - and then he stopped.
“YES!” Karen roared. “YOU LOSE, BITCH!”
It was the last thing he heard as he slowly faded. Those cruel, bitchy taunts. Both of his arms fell down, to dangle at his sides, swaying slightly. The one glove he still had on slowly slipped down his hand, and landed with a gentle -thunk- on the mat.
Billy’s wild, jerky motions slowed down. The observing moms gasped as he went still in Karen’s squeezing arms. Their talked-up boxing instructor - choked out by the queen bee bitch Karen.
A few last burbles escaped Billy’s frothing lips, before he went totally slack, slumping over into Karen’s body. Only still standing because the bitchy milf was holding him up with that ****.
Purring with pleasure, Karen squeezed Billy’s neck tighter, pulling his lax body in closer, and brought her lips to the side of his slumped head.
“Goodnight, fucker,” Karen growled into his ear.
Then, Karen released him and just let his body drop. The great champion landed unceremoniously with a dull thud and a slight bounce, put to sleep by a bitchy milf in his own ring. He never even got the chance to start teaching anyone how to fight.
“You’re out, bitch. You lose.” Karen spat hatefully, staring down at his useless **** body. What a fucking mess he was. A tangle of limbs.
Holy shit. The other moms had just seen Karen absolute DOMINATE the supposed boxing champion, with absolutely no training… If any of them had any faith left in this boxing club after seeing Billy get slept in one punch, it was gone now. Karen had firmly taken charge of all of this, just like she always did. But nobody ever expected her take charge PHYSICALLY, rather than socially… To outfight a young athletic boxing champion. Surely, the boxing club would be taking in no new members this year.
Karen turned to the crowd of moms, smug and riding high on the thrill of her win. She herself never would have predicted that she would dominate the strong, young instructor like this - at least, not until that first punch sent him down for the count. He had looked so tough when she’d first seen him. But after what she’d done to him… Goodness, was she feeling great.
So much for the “perfect athlete” Billy. Heather’s brat was fucked. Finished off by a mom he was supposed to teach how to fight.
That perfect bitch Heather would finally have a weakness for Karen to jab at - her embarrassing son, knocked out by Karen. Beloved Heather, adored by all the parents who were sick of dealing with Karen. Heather, with her perfect little athlete son and smartass daughter. Well, she didn’t have such a perfect little life anymore.
Who knew seeing a young man sleep could be so rewarding?
The moms gawked at their instructor, snoozing facedown into the mat. One of the moms was staring at his naked hands, with those curled up fingertips.
“Wh-Why did he take his gloves off…?” she asked.
There was a silence.
“My husband watches fighting on the TV,” another mother eventually chimed in. “One time a fighter took his gloves off in the ring… he said it meant they were retiring.”
Karen leered down at the sleeping athlete smugly. Hmm. “Retiring”. Karen had retired Billy. That sounded about right to her.
“He… He retired…? We just saw him… Retire…?” one of the moms asked.
“Oh my gosh… I can’t believe you knocked him out twice…” another mom said, before silence fell over the gym. Everyone just stared down at Billy. The young man who had retired his fighting career for Karen, just moments before she finished **** him out.
Karen had just won her first ever fight, by knocking out Billy. Just like how her first ever punch had knocked out Billy. What an informative seminar that “undefeated” athlete had given his milfy students.
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Loaded Gloves
She has the advantage
Overconfident men getting their bells rung
Updated on Jun 12, 2026
by Raljo
Created on Jan 25, 2022
by Raljo
With every decision at the end of a chapter your game state can change. Here are your current variables.
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