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Chapter 21
by
Raljo
What does Billy decide?
A moment of weakness
Billy stared at the gloves. Those damned gloves. Not too long ago, Billy had never once been KO’d. Or even defeated. But now, female hands slipped inside of those gloves had sent him to dreamland on four seperate occasions. Or was it five now? Five time that the leather of those gloves had connected with his face, and shown him true defeat?
Billy’s cock slowly rose back up, despite the sticky situation inside his underpants from his orgasm only moments prior.
His mom seriously considered herself a better boxer than Billy. A better fighter. She was a full-bodied middle-aged woman, and she thought she could beat her 19-year-old son in a fight for real. Utterly put him to sleep. The worst part was, as long as she had those, she wasn’t even wrong… He really couldn’t beat her. He just couldn’t. He just… Lost.
Billy’s cock throbbed against the inside of his underpants.
She’d stripped down, and knocked him out. He didn’t even fight back. He was a champion, and he didn’t even fight back.
Billy’s cock thumped twice in a row, and for a moment, he almost came. Almost blew his load into his boxers again as he recalled his last humiliating defeat. As he recalled his mother’s tits and ass.
That’s not even to mention his nerdy, bookworm little sister Anna getting the better of him. Knocking him out cold in front of their mom. Yeah, that was a good for him. A boob-jiggling uppercut, and he was asleep for hours. Knocked out by a novice. She wasn’t even an athlete. What had she said, when she woke him up and pinned him down in his bed? “I thought you were supposed to be good at boxing”?
Another double-thump.
And now… His mom was setting him up to fight Miranda? Little cousin Miranda? As well as the gorgeous, busty bombshell that was Aunt Judy… The only woman who rivaled his mom in her looks. The woman who could make a man cum without even stepping out of her bikini. The woman that Billy had desperately fantasised about so many times. She… She wanted to try knock him out too? To try and punch out her champion nephew, and make him drop? She’d always talked about how much she liked how strong and confident he was. And now she wanted to try and defeat him. No training. No athletic background. And she wanted to knock him out. Would he lose to a second milf, even worse than his current 0-4 record against Heather? After all, if Anna could do it, then why not a more mature woman…?
Billy groaned and doubled over, trying not to cum right here and now as he pictured a million different finishing shots, a million different victory celebrations. Judy was a party animal. She knew how to have fun. Would she have fun with him? Billy grit his teeth and tried not to spray the inside of his briefs with spurts of his genes.
And as for Miranda… Even Billy was curious. Could even Miranda, dainty, geeky little Miranda, could even she knock him senseless if she put those gloves on? Was all his skill and training really so easy to overcome? Small, nerdy, uncoordinated, repressed and self-conscious. A boxing noob. Sleeping a champion boxer.
Part of him wanted to know if she could actually do it. A further part of him wanted to know how she would react if she actually did do it. If she knocked out Billy. If he was shirtless, gloved up, ready to fight, and sleeping at her feet. If he was defeated. If she defeated him. An A+ student, Anna’s academic rival, and now an A+ boxer.
“Sure, I can bring them over now. No, no, I don’t mind, you’re right around the corner.”
Shit! Heather was stepping out of the bathroom. He had to go, now!
Billy rushed out of the room, leaving the gloves behind. And just in time too, as his mother opened the bathroom door and stepped into her bedroom almost the exact moment he made it to the hallway.
Fuck. Billy’s head flooded with regret. He should have grabbed the gloves. He panicked. And his cock was thumping almost with every heartbeat now. Was there still a chance to get them…?
Billy peeked around the corner. Heather was nude. Completely and totally nude. His jaw hit the floor. She looked like a goddess. His mom, who had knocked him out and really thought she could beat him in a fight, was a busty, gorgeous goddess. He couldn’t take his eyes off of those huge boobs…
“Sure. I’ll be there in 25,” she said, scrubbing her head with a towel before letting her gorgeous wet hair fall down over her shoulders. “See you soon.”
With that, she picked up the loaded gloves, along with a nice button-up shirt and some tight blue jeans, ready to drive to her sister’s house. Ready to prepare her son to be pounded out in front of her. Billy could see her small, satisfied smile on her beautiful face. He could see her natural, flowing hair. And he could see her big naked tits.
He came in his underwear again, barely holding in his moans. Then he hurried up to his room. A few minutes later, he heard the car start as Heather went to deliver the gloves to Judy’s house.
Fuck… Now what?
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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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