Chapter 23
by
Raljo
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Karen goes crazy for Billy’s dick
“O-Oh!” Karen yelped, surprised, as her hips met Billy’s.
His dick was fatter than she had realized. In one quick motion, Billy’s full length had been fully sheathed inside her warm, tight pussy, stretching out its walls pleasurably. Karen bit her lip and began slowly riding him, up and down, getting a feel for his cock.
“Oohhhhh yeah… This is good stuff…” she rolled her head back to stare at the ceiling. This boy’s dick was hitting all the right spots. Despite herself, a satisfied purr escaped Karen’s lips.
“Nnf… Keep bouncing that fat ass.” Billy grunted.
“Oho. Maybe I will, boy.” Karen glared at the challenge, though this glare was less intense and hateful than the ones that had come before.
Lifting her hips and then dropping them back down again, Karen began speeding up. Her large breasts bounced inside her top as she rode the champion’s dick with more and more vigor. Her hair fell in front of her face, messily, as she tried to overwhelm the brat with her fucking.
“Y-You should… Know your place…” she growled, feeling her walls stretch for him, like his cock was giving her tight, overworked pussy a nice deep-tissue massage. She would just have to work even harder to bully it into submission. “I’m the… Queen of this gym now…”
Yeah. That was right. Good dick or not, she was still the one doing the fucking. She was the one who had knocked him out with a punch. She was in control, no matter how good she was feeling.
“You look more like the whore of it.” Billy quipped, earning him another glare.
“Watch y-your tone… A-Ahhn~~” Karen’s eyes went wide as the cute moan escaped her lips. Her gaze snapped down to Billy accusingly, as if he had done something to her pussy, other than give it a good dick to play with. As if he had somehow cheated at sex.
“E-Enjoying yourself?” Billy asked, putting on a face of bravado. Karen’s pussy was a lot for him to handle as well, its tight wetness engulfing and hugging his dick in a cozy cuddle, but he could handle it for now.
“Sh-Shut up. I still knocked you out.” Karen reminded him. Did she just feel his dick throb and get fatter in response? She didn’t even know a cock could get any fatter.
Karen let her head hang down, her hair dangling loosely, as she brought her hands to Billy’s strong chest to stabilize herself and continued to pound against him. She wouldn’t let this boy get away with it. There was no way, the cold-hearted bitch thought, that she was going to get outfucked by one of Heather’s brats.
But that was exactly what was happening. The harder and faster she fucked him, the more of a sloppy mess she became. Moans escaped her lips without permission. Sweat beaded across her body. Warm juices trickled out from her weakening pussy lips, down Billy’s shaft. He was pummelling her with his dick, that perfect dick. The milf was losing control.
Meanwhile, Billy showed no signs of crumbling. Nothing like Karen did. A slight redness to his face was nothing to Karen’s burning cheeks. An occasional grunt was nothing to the choruses of yelps and moans from the stacked milf fucking herself stupid on his dick.
She hasn’t expected this. She hadn’t expected him to be this good. She was losing badly, but she couldn’t back out now. She didn’t even want to. Karen, the serial complainer and all-around arrogant, hated bitch, was being fucked into submission by the student brat she had meant to humiliate. She was making mewls and purrs and sounds that nobody had ever heard her make. And she didn’t like it.
Her red face twisted into a scowl, glaring down at Billy, with her hair hanging either side of her face like messy stage curtains. She didn’t slow the fast, powerful slamming of her round ass onto his pelvis.
“I- I hate you,” she said, glaring at him, as she hilted his dick inside herself again. “I hate you, I hate you, I hate you, I h- haaate… I-“
Her sour face morphed into one of ecstasy. Somehow, her piston-like thighs and broad hips sped up even faster.
“I-Oh… Oh my GOOOODDDDDD—!!”
Karen kept ramming herself down on his thick rod, to the point of losing her mind. The mature, bitchy, domineering woman was overcome by pleasure.
“FUCK! FUCK! FUCK! FUUHCK YESS~~!”
She was a mess. Her eyes were unfocused, and slightly crossed, as she yelled out into the large, empty, echoing gym. She looked like a stupid whore, the true definition of getting your brains fucked out.
“YOU BRAT! YOU LITTLE SHIT! FUCK!! FUCK YOU! FUCK YOU! FUCK YOOOOUUUU~~!”
Karen came with a scream. Her cunt pulsed, vibrating and massaging Billy’s dick as her body was wracked by the largest orgasm she’d ever felt. It was shameful, watching a grown woman shaking and quivering on the dick of a teenager. The blonde, bitchy milf was cumming this hard for a brat, and there was no way she could hide it.
Fuck, she hated him… Gawd, she luved this diiiicckk…
“A-Aghh-Ahhnn~~”
Karen panted, and her eyes rolled back into her head. She managed to find the willpower to lift herself, on shaky, smooth legs, off of his dick - before her knees gave out and she felt uselessly onto her back.
Karen hid her red, sweaty face in the crook of her elbow, panting in shock and disbelief. Her stupendously sexy milf body had broken down like a piece of old machinery. An overworked, quivering heap of defeat. What had she ever done to deserve such a heavenly fuck?
“F-Fuck you… You’re disgusting… I hate you…” she said between heavy breaths, eyes still hidden by her arm.
THIS was the woman who had taken it upon herself to humiliate him, and knock him out cold? Billy grinned at her. She was a mess. He hadn’t even needed to do anything, but watch Karen dick herself into submission. For the first time in recent memory, Billy had won against a milf. And this was quite the win indeed.
“So, I take it you’re deleting those pictures?” Billy asked, lifting himself to his knees to survey the shaking, heaving mess of a milf who had subjugated herself on his cock.
Karen took her face out of her elbow and glared at him. The hateful fire had returned to her eyes. She hated losing, and even now refused to admit how badly she just had.
“No. Fuck you.” she growled. “Everybody going to see that you got knocked out. Everybody’s going to see your stupid fucking- Ahhn~! F-Fuck! FUUUCCKK!!”
Billy’s rugged fingers found her soaking, shivering pussy, and began fingering it convincingly. Karen’s head jolted back, her mouth falling open in a stretched-out ‘O’ and her back arching off the ground as he ran his fingers skilfully through all of her newly-found weak points. His dick was the bomb, and his fingers were the cleanup crew sent to take care of any survivors.
“NO! F-FUCK YOU! I WON’T… I HATE YOU! I… I…”
Karen let out a loud yell.
“FINE! I’LL DELETE THEM! I’LL DELETE THEM! I’LL DELETE THEEEEEMMM!!” she shouted, as she came like a geyser.
Girlcum squirted from her cunt farther than anyone would have thought possible from such an uptight bitch, before she fell back again with a moan, and not enough energy to even lift her blonde head. The cold-hearted bitch reduced to a moaning, quivering heap once again.
“Thank you,” Billy smirked.
He leaned down and kissed her on the blushing cheek, and she glared hateful daggers at him. But when he withdrew, she grabbed him by the back of the head and pulled him back towards her lips for another, deeper tongue-kiss. Billy was surprised, but happily engaged Karen in the liplock.
She put up a brief fight, but soon resigned herself to losing the tongue battle as well. She just didn’t have the energy to fight back. Billy easily wrestled her submissive tongue down, grabbing her by the back of the head now, and pulling her deeper in to his face with ****. Karen’s eyes glazed, and she moaned against the student boy’s lips. When Billy finally finished, he pulled away, a string of saliva joining their lips and then snapping as the distance grew too far.
“I hate you…” Karen mewled softly, a hand running down to her pussy. “I… I love you… I hate you… Fuck…”
She was just on autopilot now. There was nothing of Karen left in there. And those pictures were as good as deleted.
Satisfied, Billy turned to leave. He’d thoroughly beaten the challenge of Karen’s uptight pussy. Effectively pleasured the domineering attitude right out of her. But he barely made it one step.
“N-No…”
Face burning hot and red, Karen reached up and tugged on Billy’s arm to stop him from going. He looked back at her, but her embarrassed face was turned to one side, refusing to make eye contact. She seemed more surprised than anyone as she clung tightly to his wrist.
“L-Let’s… Again… Some time,” she finally managed to say, clearly at great strain to her pride. “P-Please…”
Billy’s cock twitched at the sight. It had seemingly melted away her bitchy coldness. What was left was a shy, embarrassed milf with a tight pussy, amazing ass, and great tits. And she was begging for his cock. There was only one thing Billy could say, looking at her now, and remembering the stuck-up bitch she used to be.
“Ha.”
He pulled his wrist from her grip. For a moment, Karen’s heart skipped a beat fearfully, dreading that he might just leave her there. But Billy wasn’t walking towards the door.
Taking a marker from a nearby gym whiteboard, Billy approached the moaning heap that had once been Karen. Lifting the lower hem of her top, he wrote his phone number over her sweaty lower abdomen, almost as if signing her womb. Karen shivered with pleasure, but made no other move. When he was done, Billy capped the marker, threw it down between the tamed bitch’s large breasts, and left her alone lying there. He walked out of the gym.
“A-Ahhnn~~”
Karen mewled, and stretched out her arms like a cat. The marker rolled off of her big milf tits, landing next to her head. Karen ran a hand down her body, its fingers gliding delicately over where Billy’s phone number marked her womb.
Nothing remained of her bitchy attitude. She felt happier and dreamier than she ever remembered feeling before. Karen the milf had tamed herself on the cock of a boy who went to the same school as her daughter. And now, she lay there alone in the gym, sweaty and gushing and paralyzed by pleasure. And all she could think about was doing it again with him, in her own bed. Her plans to humiliate Billy, to make the school look bad, to show off to the other moms… They were all forgotten. That cunt Heather might have been a stuck-up bitch, but she had sure raised a good boy. A very fucking good boy indeed.
Karen cooed, rubbing her hand over Billy’s phone number.
Yes. That sure was one good boy. And good boys deserved to fuck naked milfs facefirst into their own collection of pillows. She hoped desperately that he would accept the invitation when she sent it. Her face burned imagining herself typing the text, but she didn’t care anymore. She wanted him in her bed. She wanted to show him her naked breasts. She wanted his approval, his dick. She wanted to totally submit. Karen wanted Billy to be hers, and she wanted to be his. Student or not, she just didn’t care anymore.
She was his first knockout loss, and he was her first real dicking. She had never cum like that before. The two of them were meant to be. Her milf boobs and ass were as good as his, to play with, to fuck roughly, to own. The infamous bitch Karen had finally been tamed.
“D-Date me… Love me… F-Fuck, I love you… Nnn…” she quietly admitted to herself. A quiver passed through her as the next, final word escaped her lips.
“B-Billy… aahhn~~”
And, just like that, Karen was no more.
Fuuuucckk. That was a good dick.
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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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