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Chapter 37
by
Raljo
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Karen gets Billy off, then sends him home
“You’re **** for it… Very well,” Karen said, tracing small circles on Billy’s needy cockhead. “Strip naked, and lie down on the table.”
Billy did as she said, mindlessly taking his clothes off and lying back on the large dining table, his legs dangling over the end. Karen’s basically-nude body was right in front of him, her bare torso flanked by that fluffy red open dressing gown. Billy’s dick was rock fucking hard and standing upright - completely exposed for that sexy blonde fox.
With a cruel smirk, Karen stretched out a hand and rubbed a fingertip along his throbbing, needy cockhead.
“Since my pussy did such a number on your poor, battered brain, I won’t bother trying to fuck you,” she leered, as Billy whimpered beneath her touch. “If I did, you might lose your mind for good. I promise you, whatever skanks you’ve fucked before don’t compare to me. My pussy hits different.”
Billy gulped. Karen didn’t know, of course, that he was still a virgin. He had no doubt that a fuck from a woman like Karen could do some serious damage to his mind.
“So alllll I’ll do… Is take these breasts that you seem to like so much… These breasts that you don’t deserve…” Karen said, holding her tits up with her hands, then letting them drop. “…And press them against that big, thick, naked fucking dick. Push them riiight~ into your lap, like this…”
Karen leaned forward, and just as she said, slowly pressed her soft breasts against Billy’s hard, hot, throbbing dick. Her mature chest easily contained Billy’s excited virgin dick, wrapping it up in a pillowy warmth completely opposite to the smug, bitchy attitude Karen exuded.
“…And see how long you can hold up,” she smirked. “Come on, brain fog boy… How badly do I own you? How much power do I have over that hyperactive little cock?”
Billy’s cock was anything but little. Hyperactive, though? This dominant rich bitch sure made it look that way.
Already, it was jumping around in her tits. Just from a simple press. Just from feeling the rich, silky softness of Karen’s chest. Just from a bare-boobed dick cuddle.
Billy gasped, his cock jumping around in those tits harder - faster. Karen didn’t even have to move, just hold him. After the earlier build up, the young athlete was just too excited. And as a dark chuckle escaped Karen’s lips, Billy couldn’t hold it anymore. She had him wrapped around her little finger, and he was wrecked.
With a pitiful moan, Billy’s cock gave in, cumming helplessly against Karen’s bare breasts. The dominant older woman laughed, pulling away from the cock cuddle to watch the show. Billy’s freed cock was spurting everywhere, as he lay back on that table twitching as gasping for breath, completely overwhelmed and losing his mind through his dick.
“Goodness me!” Karen couldn’t help but laugh at the sight.
Poor Billy… Poor boxing champion Billy. Overwhelmed by a milf. Karen laughed at the sight, making Billy tremble even more with humiliation as his dick just kept on spurting out semen.
“Dearie me, you are so cummy!” Karen sneered. “Tsk, such a big load just from my breasts? You’re adorable. I barely even had to move them.”
As Billy’s gasps and shaky moans died down, his overexcited cock finally slowing, a deep shame overtook him. This bitch had knocked him out… She had a good chance of ruining his life. Why did she get him so fucking hard?
“I know I’m hot, but really…” Karen purred. “Have some self control, Billy…~”
The condescension made his face turn red. She was right. She was just so hot, he had no self control. This smug, milfy bitch was the one controlling him. And he just let her do it. Where was his fighting spirit?
“It’s no wonder my pussy gave you weeks of brain fog… You’re not built to handle any part of me,” Karen gloated.
Billy opened his mouth to reply, but had nothing, so he just closed it again. Looking like a dumb fish. Karen purred at the obvious submission, but then a strange fondness crossed her face.
“You know what? You can have today off. You can clean this place up tomorrow. It’s late. And I can tell you don’t have it in you right now~” she cooed.
Billy shivered, still laying back on the table, fighting a torrent of emotions. Feeling weak, feeling dominated, feeling beaten… Feeling loved? Karen noticed his pathetic, silent reaction.
“Oh my, you’re shaking…” she said, as she put a hand to his strong chest, feeling his quaking shudders on her palm. “Awww, do you need a goodnight kiss~?”
With that, Karen bent over, her large soft breasts dangling straight down to allow Billy a perfect view deep into her cleavage. She puckered her lips and leaned in close, kissing him softly on the forehead. Just once. It was a surprisingly gentle and motherly moment from Karen, and the unexpected affection confused Billy’s reeling, rattled brain.
“Good night, brat.”
The rich matronly bitch let out a mocking laugh, as Billy finally got up, pulled on his clothes again, and hurried home.
Karen had him so fucked up. Her aura of authority was inescapable. Power emanated from that mature body. The whole way home, Billy could only think about her. Standing nearly-nude in that open dressing gown. Proud and confident in that divorced older woman’s large, expensive, richly decorated house.
No doubt, Karen felt like a winner. She was now convinced that she had stripped away all of his boxing talent, given him weeks of brain fog, and made him obsessed with her body. That young man had lost everything to her. Physically, mentally, sexually, she owned him.
She couldn’t possibly feel any more superior if she tried.
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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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