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Chapter 16
by
Crushedone
What's next?
An unexpected start
"Mom, just what are you trying to prove? You are either going to get hurt, or if you do win it will be because Matt was holding back," Billy said nervously as he watched Anna help their mom into those damned loaded gloves that were the source of all his troubles.
"That attitude is precisely why we are having this little experiment, young man," Heather scoffed in annoyance. "You told Anna that you were intimidated because she might be better at you than boxing. You would have us believe that you were holding back for our sake, but I saw how nervous and sloppy you were. And now that we know that your performance has been slipping with your teammates too, I think I know the reason why..."
Billy blushed in embarrassment at the thought of his mother finding out his horny little secret. "Mom, I can ex-!"
"You're ashamed," the boy's mother interrupted with absolute certainty in her voice. "You think that just because you are the man of the house, you should be the strongest. You've been an undefeated champion for so long, that the idea of a beautiful woman demolishing you, putting you to sleep with her soft, dainty little fists, and then stripping you of your title, all almost effortlessly, it's..."
Heather trailed off when she saw the mortified look on her boxing son's face. Luckily, Anna was there to finish her sentence with a smirk. "It's humiliating!"
"Yes Anna, thank you," the chesty mama smiled at her daughter, trying to hide the amusement she felt from watching her formerly unstoppable son deflate. She gave him a reassuring pat on the cheek while wearing her prized boxing gloves, and was secretly very proud when she saw him flinch at their approach. "Don't you worry sweetie. Mommy is going to make it all better by showing you that you have nothing to be ashamed about..."
Before Billy could protest about being spoken to like a frightened toddler, Matt came into the room dressed in his boxing attire. "Alright Ms. Heather, are you ready to get started?"
"Yes Mattie," she responded with a dazzling smile before shoeing her kids out of the impromptu ring. "And there's no reason so formal. You are an adult after all. A full grown man. Just Heather will do fine..."
Matt gulped at the wink the milf sent his way and nodded. He squared his guard, mostly hoping to hide the blush on his cheeks. "S-so I guess we go until someone cries 'uncle'..?"
"I'm sorry, but no," Heather shook her head, the sweet smile on her face morphing to something more devilish. "My son wants us all to believe that his sister and I sent him to Lala Land by accident. My job is to prove that isn't the case. I also need to be sure that you are taking this seriously..."
"M-mom..?" Billy's eyes widened in realization, "Y-you can't seriously be thinking that..."
"We go to knockout," the busty mother heard with excitement.
Billy was horror stricken! This was the worst possible scenario. If Matt won the fight and hurt Billy's mother, they would all feel terrible about letting this whole thing get out of hand. Especially Billy who was the cause of all this madness. On the other hand, if his mom won, which was a very real possibility with her reinforced gloves, this would only cement her superiority over him and allow her domination to continue. In fact, it would likely grow worse now that Anna was starting to demonstrate similar power over her brother.
"Mis-? Oops, sorry. I mean Heather," Matthew corrected himself timidly, "I'm not going to try to knock you out! I told you before that I don't want to hurt you."
"You really are such a gentleman, Mattie," Heather smiled with a seductive lilt to her voice. She started swaying her chest back and forth ever so slightly, just enough to grab the young man's attention. When she saw his arms start to slack and his mouth open, she's smirked. "Alright, if you feel like you should stop at any point because you think you're hurting me, we can stop. But I want you to know, that doesn't change anything for me. I plan to end this match the same way my first one with Billy ended. With you face down at my feet, drooling all over the floor..."
Both boys in the room felt their dicks stiffen at that image. Matt had to clear his throat to keep his voice from cracking, "Y-y-yes ma'am..."
Both opponents then raised their fists and started slowly approaching one another. Matt gave a few light punches, testing out Heather's guard and reactions, but she just his gloves bounce harmlessly off her arms. She giggled at the weak punches, a flirty sound that distracted the veteran boxer. She gave a few slow, easy punches of her own, barely a tap. Matt smirked at the playful nature of her strikes, enjoying the peek at her gigantic tits that each one offered. He relaxed his guard, feeling more and more like this whole situation had been a joke. The next time he swung, his shot was intentionally slow and overextended.
Heather didn't waste a second. Her fist shot out like a snake at his open face. Matt's instincts kicked in and he dodged back, trying to block the blow with his other arm. Unfortunately, he had to reach across his body to do so and he was only able to slightly deflect it. The milf's punch glanced her opponent on the side of the face, and with her loaded gloves barreling forward the blow was far more brutal than he was ready for. Matthew went down hard, twisting as he fell. He rolled when he hit the floor, his body naturally trying to correct itself where he ended up on all fours facing the mesmerizing woman who had nearly taken his head off.
Matt's eyes darted around the room, trying to make sense of where he was and what had just happened. The young boxer felt like he had just climbed off a tilt-a-whirl! Or rather, he felt like one had just slapped him across the face if the pain in his jaw or any indication. He could hear Anna cheering for her mother. As he settled on the shape in front of him and his best friend's full-bodied mama started to take shape again, the stunned boxer jumped to his feet, almost falling back to the floor with how unsteady his legs felt beneath him.
"I told you to take me seriously, Mattie..." Heather sang with a teasing shake of her chest once her opponent had regained his balance. Matt couldn't believe what he had just experienced. He knew he had avoided the worst of that blow, but his head was still throbbing and swimming. If he had taken the full brunt of it, she might have just landed a one hit KO! Nobody had ever pulled that off, not even Billy!
"Y-you're right Mi... Heather... Lesson learned," Matt replied nervously putting his guard up while the hot mama just stared him down with her unwaveringly confident smile. It was clear she was absolutely sure that she could repeat what had just occurred, and that she looked forward to doing it. That made the boy nervous...
And excited.
"Good," she gave an approving nod before lifting her own fists. "Then get ready, Matthew. Here I come...!"
What's next?
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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