Disable your Ad Blocker! Thanks :)
Chapter 20
by
mlg3789
How Does The Match Go?
Decent, at first.
"Let's do this," Billy said grimly. Karen had really given him ****. Five minutes of straight-up taunting had humiliated him, and he hadn't managed to make a dent in her confidence. And she wasn't about to let him simply walk past her.
She had boxed him in, without even throwing a punch. Well, except for those two mini-punches, the second of which had glazed his eyes over. Billy would fight her, and this time he would win, because the gloves weren't loaded. But he still had to be careful.
"You may want to take those off," he said, glancing at her high heeled open-toed shoes. Part of him wanted every advantage he could get, and he could picture how bad her footwork would be with those inappropriate shoes on. On the other hand, if she was going to beat him, he didn't want it to be while she was handicapped by high heels.
Clearly her psychological warfare was getting to him. "Such a gentleman," Karen purred as she effortlessly slipped her shoes off and kicked them to the side. Then she slowly unbuttoned her fancy blouse to reveal a white tank top. Each of the first three buttons slowly revealed more of her perfect tits, and Billy couldn't help but look.
Karen stepped into the ring with Billy and put her fists up. Billy was already sweating, more from fear than anything else. This was supposed to be his comeback, something to reassure him after his recent defeats at the hands of his mom and Anna. And now he was afraid of losing to yet another unathletic MILF.
Except Karen wasn't exactly unathletic, Billy noticed. She was just as curvy as Heather, but her body was harder and tighter. Now that she'd taken her blouse off, he could see a little bit of muscle in her upper arms, and a very slight hint of abs under her tank top. It was clear she put a lot of care and money into her appearance. She was rich, and Billy thought she probably had a personal trainer helping her work on her body.
Whatever she was doing, it was working. Billy felt his dick get hard, pressing against his shorts, and he hoped she wouldn't notice. But her perception seemed two steps ahead of his anyway, so he knew his hope was useless.
"I don't think you're ready for this," Karen taunted, with a predatory smile. Damn, this bitch was relentless with her taunting and insults, Billy thought.
Fortunately, Billy's fear evaporated when Karen started to approach him, barefoot and confident. Her footwork was atrocious, and she clearly had no actual boxing experience. She lunged forward with an overconfident cross, and Billy let it slip by his shoulder, harmless. He then knocked aside her next punch, a hook aimed somewhere in his belly area. It was so clumsy that he couldn't even tell what she was aiming at.
Fuck it...if she was going to be like this, he might as well make a lesson out of it. After all, that's what Coach Lucy asked him to do, wasn't it?
Billy sidestepped another of Karen's clumsy punches and tagged her on the ear with a little hook. "Ow!" she yelped as she backed off.
"Best way to not get knocked out is...to not get hit in the first place," Billy told the other moms as he avoided another blow from Karen, shrugging it off his shoulder. They were starting to get interested, crowding around the ring. Billy could sense that although the general opinion was in favor of Karen, at least a few people were happy he was teaching the bratty MILF a lesson.
Billy followed up with a crisp jab-cross combination to Karen's unprotected face. "Ughhh!" she gasped, taking an awkward step back.
"When your opponent overextends, always make sure to capitalize with a counterpunch," Billy said smugly, as Karen shook her head to clear it.
Then she surprised him by rushing in with some big swings. He stepped out of the way of the first two, but she was faster than expected and her third swing solidly hit his guard.
SMACK! The noise echoed through the gym as Billy was pushed back a bit. Karen grinned and raised her eyebrows at him. The hit was way more powerful than he had expected...it almost felt like Heather's loaded gloves.
Whatever. She must have accidentally coordinated her swing with a lucky twist of those sexy hips. He just needed to keep dodging and stop trying to block.
Billy and Karen squared off again. Karen was sweating and her breasts were heaving, but she didn't look hurt by any of the punches Billy had thrown at her so far. The other moms were rapt, every iota of their attention on this unexpectedly exciting bout.
What's next?
Disable your Ad Blocker! Thanks :)
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.
- All Comments
- Chapter Comments