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Chapter 23
by
mlg3789
What's next?
Karen savors her victory.
Billy woke to the bright gym lights shining directly into his face. His whole body hurt, except his cock, which was rock hard and currently getting stroked by something soft and smooth. He let out a soft moan as his eyes adjusted.
"Oh, are you awake? That's good, I was starting to worry..." came Karen's unmistakable voice. Billy lifted his head and stared blearily at her. The milf was standing over him, and as he traced her formidable figure, he looked down her long leg and realized that her bare, delicate foot was what was stroking his dick.
"unnnhhhhhh," Billy moaned again, shifting slightly in an effort to escape her touch. Her touch was tempting, but dangerous.
The pressure from Karen's foot increased as she pinned his cock to his belly underneath her sole, but her voice was soft. "Don't worry, I won't hurt you...at least not any more than I already have." Karen giggled softly. "Just....don't....move," she continued.
Billy froze, and Karen lifted her foot off his cock. He felt her coming closer, even though he wasn't looking straight at her.
He felt like some kind of a prey animal, a rabbit maybe, frozen in place as a predator approached, hoping she hadn't spotted him but knowing deep down that she had, and it was too late to run, and she was too strong to fight.
She sure was showing an awful lot of nicely tanned skin, Billy thought. As his brain continued to come out of its fog, he realized that Karen had stripped off her leggings at some point. Now she was just wearing some cotton panties and a low-cut sports bra.
What the fuck? What was happening right now? Billy's eyes darted around the room, wondering how many of the MILFs were still here watching him. He didn't see anyone though.
"Oh, they all left. I sent them home. Had to take over the lesson when you didn't wake up right away," Karen said matter-of-factly. Then, straddling him, she sank down to her knees and put her hands on his shoulders, pressing him down into the floor. Slowly, she relaxed and leaned back until her bare thighs surrounded his hips and her crotch rested right on his hard cock.
Billy couldn't control himself, he reached for Karen's hips. He hadn't decided whether he was going to try to throw her off him, or just grab her hips and slide her along his cock. It didn't matter, though, because Karen intercepted both his hands, lacing her fingers with his own. He fought her at first, but his arms felt like lead, and she had the leverage too. She overpowered him in a second or two, and slammed his hands to the floor.
Karen stared into his eyes. "No more fighting. You lost," she said sternly. Then, slowly, exquisitely, she dragged her panty-clad crotch over his cock, pressing it tightly against his stomach. Billy threw his head back and moaned, already near the edge of cumming hard. But Karen didn't reverse direction. Instead she kept rubbing her crotch against his stomach, and up to his chest, letting his cock spring free and denying him the orgasm he now shamelessly craved. Karen stopped there, her weight on his chest. Then she placed one knee on each of his biceps. Billy groaned in pain as she crushed his tender muscles.
Karen only grinned. She released his hands and said, "I want to show you something Bianca gave me." She reached to the side and grabbed her phone. After a couple of taps, she turned the screen toward Billy and held the phone in front of his face, resting it against her stomach.
He instantly recognized the action. It was the last few minutes of their match, from Bianca's point of view. She'd recorded it. Billy was currently deep in Karen's clinch, his whole face unseen, pressed against Karen's smothering tits. He watched as she outmuscled him and slung him against the ropes.
As the cheering of the other MILFs escalated, Billy saw Karen brush aside his pathetic guard and start pummeling him like a punching bag. Seeing her from behind, he gained a new appreciation for her body. Every punch she threw, he could see a hint of lats or triceps in her shoulders and arms. And her butt was big and round and tight and firm, and it jiggled alluringly every time she connected with a punch.
As much of a turn-on as it was, Billy was humiliated all over again. Karen was hot and strong, but she still shouldn't have been able to beat him, and her questionable technique was visible on the video. Yet she was giving him the ass-kicking of a lifetime. Worse than what Heather had done. Worse than what Anna had done.
Nothing less than his complete, public destruction at her hands. It was bad enough that several people had seen it. He had no doubt the moms would be gossiping about it for weeks. But it was on VIDEO? He would never live it down.
Karen could see it in his face. "It's all right," she cooed, patting his chest reassuringly. "Bianca is a nice lady, after she transferred the video to me, she deleted it at my request. Now the only one who has a copy...is me," Karen said.
That wasn't reassuring at all! Just as he was literally trapped beneath her right now, he would be figuratively trapped--under her control--as long as she had the video. His eyes were drawn back to it.
He recognized the moment he blacked out by the combination of vicious hooks Karen used, and the vacant look in his own eyes. He saw himself go slack while the MILFs gasped in amazement. He saw his body crumble and his face smack against the mat inches from Karen's pedicured toes.
As Karen started to count him out theatrically, Billy's cock started to harden again. It had barely softened since Karen moved off of it, so it only took a second or two to come back to full hardness. By coincidence, Karen picked that moment to reach behind herself and grab it. "Ooh!" she exclaimed in pleasant surprise. "Does watching me kick your ass turn you on? I bet it does!"
Then she started stroking him. Billy struggled uselessly, not even managing to budge Karen from her spot atop him. "If it doesn't, I bet we can build the association right now!" she said. As Billy watched the video of Karen strutting around his own insensate body, he began to lose control. Just before he spurted cum all over her back, a bit of motion distracted him. He watched as video-Billy struggled to his knees, then to his feet, tottering slightly. Video-Billy raised his fists gamely, maybe not far up enough to protect his face, but far enough to look vaguely like boxing.
"I got back up?" Billy asked incredulously. He had no memory of it whatsoever.
Karen read his face instantly. She could tell he didn't remember this next part. "Don't get too excited," she laughed.
Sure enough, video-Karen didn't seem too intimidated by video-Billy's last-ditch efforts. He staggered towards her, taking an exaggerated swing that she easily got inside. She slammed her fist into his gut, folding him over so that his chin was resting right on her chest. Then she pushed him against the ropes. She started hitting him all over with a rapid series of blows. Video-Billy's face was totally slack. The flurry of punches was similar to the last one that real-Billy remembered, only it was faster, harder, and more accurate.
Soon enough, video-Billy fell like a ton of bricks, this time totally defeated. Billy could tell there was going to be no more movement from his body.
Karen counted him out, making it to 10 long before Billy stirred. She accepted congratulations and cheering from the crowd. If anyone had been rooting for Billy earlier, they certainly didn't make it known now.
Video-Karen was addressing the crowd. "Well, ladies, I guess I overdid it! I didn't MEAN to hurt him, but really...a qualified instructor should have been able to handle an inexperienced mother like me!" The other women murmured their agreement.
"I'm going to have to have a talk with whoever's in charge," she continued. "Maybe we can pick this up again next week? It'll take a few days to find a suitable replacement." She nudged Billy's legs with her foot, but he didn't respond.
As he watched the video and the MILFs leaving, Karen continued to stroke his cock. He found himself right back at the edge, and he could tell Karen knew it because she was subtly picking up the pace.
The video ended, and Karen leaned forward, looking directly at Billy's eyes. "Nobody else has to see that video," she said intensely. "And they won't...as long as you do a couple of things for me."
"Anything," Billy croaked instantly, without even thinking. Images of them fucking each other for real flitted through his mind. Karen seemed to know what he was thinking, because she grinned seductively.
"Yes, anything. But not just that," she said mysteriously. "You'll be my sex **** today and until you go back to college, that goes without saying. But you're going to have to be my regular **** too. You'll come over every day for an hour in the afternoon and clean the house. And once a week we'll have another boxing match. It's okay, it'll only be me and Selena there."
She must have seen Billy's look of despair, because her face softened for a moment. "I'll tell you what...if you win one of those matches, I'll release you from servitude and delete the video," she said. Billy relaxed a little.
Then Karen grinned again. "But you won't win one," she said. It put Billy over the edge. He bucked suddenly, spasms of pleasure taking over his body, thick cum spurting out of his cock and splattering all over Karen's mostly-bare back.
"Ugh!" she exclaimed. "I was going to go straight to dinner from here! Oh well, they can wait for me to shower."
Billy went limp as the pleasure subsided, but Karen didn't get off him. He tried to roll her off, but she didn't budge, pressing him back to the floor with her solid hips. "Ah ah ah...my turn," she said menacingly.
She slid her crotch up a few more fateful inches. Her panties brushed against Billy's chin, and he could feel that they were drenched. Karen wasted no time, pulling the thin panties to the side and pressing her bare pussy to Billy's mouth.
"Mmmmmffff!" Billy exclaimed in a muffled voice as she pinned his face to the floor with her pussy. She started sliding forward and backward, hard deep strokes that hurt his head and neck. He tried his best to participate, but really she was just using him as a sex toy.
She must have been building up an orgasm throughout the match, because within seconds she was gushing, and he felt her abs and thighs tense with a tremendous ****. "AHhhhhhhoooomygggooodddddd!" Karen screamed as she came all over Billy's defeated face.
The lack of oxygen was getting to him. He feebly groped at Karen's thighs, trying to get her to spread her legs and give him a little air to breathe. Either she didn't notice what was happening, or she didn't care, because she just continued to let him suffocate under her.
As Billy drifted off into yet another knockout, the big picture came into focus: he was done. Finished. As a boxer, and as an autonomous human being. He'd indulged in his fetish one too many times with Heather, but at least she wouldn't have taken advantage of him. Then he'd allowed himself to be beaten by his sister, who probably WOULD take advantage of him but at least liked him. This was an unrelated woman he knew to be a stone cold bitch, who had publicly dominated and humiliated him, and in the process constructed a **** scheme that would keep him from ever escaping the same repeated fate. Karen's leverage over him was total, her domination complete.
Billy blacked out, and the final thought that stuck in his mind was that the sexy MILF would own him forever.
What's next?
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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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