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Chapter 15
by
Crushedone
What do they ask Matt to do?
Fight Anna
"We'd like you to box Anna," Heather said gesturing to her daughter. Both young men's eyes went wide in response.
"Box Anna...?" Matt asked nervously as he looked at the smaller girl and tried not to focus too hard on her enticing figure. "I don't know ma'am. I don't want to hurt her, and boxing can get pretty rough..."
"That's very sweet of you dear, but I promise Anna is tougher than she looks. Just ask her brother," the mother replied, fixing her son with a knowing grin. He shrank under her gaze, and she loved her growing power over him. "We thought their little match last night had shown just how much potential she had, but decided that maybe we should test that on a different opponent who we could trust to be honest with us. That's where you come in."
"We thought about letting you judge a match between one of us to see if Billy was holding back, but decided that might not be as effective. Especially since Billy has had his bell rung pretty good lately," Anna said, giving her brother a wink before continuing. "So we decided you should spar one of us yourself to judge our ability. Mom does have more experience than me since she got to train with Billy while I was gone, but we decided it should be me after he mentioned last night that I was as good as some of the guys he trains with at school."
That got Matt's attention and he now looked at Anna with real intrigue at the idea. "Really? He actually said that?"
The girl nodded and then all eyes were on Billy. The young champion's mouth went dry at the looks of expectation from everyone in the room. Shit! How was he supposed to explain this all away now?! He thought he would have time to talk to Anna and sweep his claims of her superiority under the rug, but he had just climbed out of bed into a bear trap, and now he was stuck!
Or was he...?
There was no way Anna could take on Matt if he was really trying. If he let them go at it and told Matt not to hold back, then once Matt won Billy could just explain that he had always gone easy on them! Sure, he would have to say that he didn't expect them to be so strong and that he clearly had a glass jaw, but everything else could be explained away as being a good son and brother. Even admitting the knockouts to Matt might be embarrassing, but it sure as hell beat the alternative of confessing that he was getting off to the thought of his mom, and now his sister punching his lights out. He just had to make sure Matt took this seriously.
"It's true," Billy said with a suppressed grin. "She's a natural. They both are. It must run in the family. I know you might want to hold back against an amateur, but believe me, you'll regret it if you do."
Both women smiled, acknowledging the praise that the trained champion had given them. Matt looked mildly surprised, but gave a friendly grin before turning to his apparent opponent.
"Alright then Anna, I guess you're on! Just let me get changed," Matthew smiled before heading to the downstairs bathroom to change into his gear. Billy smirked at the thought of things getting back to normal after Matt took Anna down a peg... then he paled when he saw her putting on those damned boxing gloves.
"A-anna...?" Billy said slowly, his eyes following intently as their mother helped her put the loaded gloves on. "Do you maybe want to try my gloves? Those have been getting a lot of use lately..."
"Oh hush, yours are far too big. Besides, these are practically brand new since you can't last more than a few good shots to chin..." Heather scoofed as she finished helping her daughter. The look she gave her soon was still sweet, but Billy would have to be blind to not see the arrogance on her face as Heather reminded him of his frequent defeats. He gulped, his dick lurching at sight of the two dominant women who had left him a drooling mess on the floor.
"I'll try not to be so rough with your best bud," Anna giggled, bouncing up and down a few times in excitement and treating Billy to quite a show in the process. Her older brother blushed and looked away, desperately trying to ignore his growing attraction to his sister's looks and attitude. Luckily Matt came out a few moments later, fully dressed for their match.
"All set! Hope you're ready to lose Anna..." Matthew said playfully, enjoying the smile he received in return.
"C'mon tough guy, and let's see if your fists are as tough as your mouth," the young bookworm flirted back before leading him to the living room which was still cleared out from her fight with Billy the night before. Anna was enjoying herself so much that she completely forgot about the tiny athletic shorts she was wearing and how her thick cheeks were spilling out of the material. Matt's eyes nearly bugged out of his head as he followed, watching her hips sway confidently. He was far too distracted to listen when Billy tried to give him a quick warning about what to watch out for with Anna.
"Oh no you don't! You are precisely the reason we are having this little experiment, and you are not going to interfere before we even get started..." Heather said with a motherly glare that was 10 times more effective now than it was months ago. She placed a finger to her son's chest and with the slightest bit of effort pushed him several steps backwards until he collapsed onto the couch. She looked down on him with all the tenderness of a mother and the authority of a queen. She sat down next to her son, her large breasts giving a massive bounce as if to cement her authority.
"Alrght Anna, we'll do this nice and fair. We keep going until our opponent cries 'uncle'. Sound good?" Matthew asked, stretching his arms in preparation.
"Sure. And if they don't, I guess we go to knock out..." Anna replied with a wink.
Matt didn't look convinced, but gave her a friendly smile before nodding. "Sure thing. Are you ready..?"
She raised her guard like her brother had shown her with the dangerous weapons on her hands. "Bring it on, big boy..."
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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