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Chapter 44
by
Raljo
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Anna’s jaw drops
Holy shit, this was EVERYTHING. This was the motherload.
As Anna read through the weeks of conversation history, she just grew more and more stunned. As it turned out, “Karen” wasn’t a student, or one of Billy’s friends - she was a MOM. She had a daughter, named Selena. In fact, though the two never spoke, Anna was pretty sure she’d seen Selena around the school before.
More than that, the text exchanges revealed a never-ending supply of shocking information. Billy’s messages were ****, subservient, fawning. He would flatter Karen, while debasing himself, and begging. Anna could hardly believe her older brother had typed some of these.
Billy: To be honest, when we boxed...you hit me so hard the brain fog still hasn't lifted. I've been having trouble remembering things
Karen: I knew you couldn't handle this :)
The message came with a boxing glove emoji. And later, in that same conversation:
Billy: My skills are getting worse, and I'm worried that I won't even give you a challenge next time we fight.
Holy shit. Was KAREN the one who had been pounding him out? Was the mystery girl just a symptom of Karen’s domination?
At first these messages made it seem like Billy and Karen were fucking. His fawning messages, her constant requests for him to arrive at her house at certain times… But Anna was quickly disillusioned of that.
No, Billy and Karen weren’t fucking. Billy was Karen’s SERVANT.
Karen: You're right, it would be more exciting to beat you up if it's more of a challenge. Go ahead and go to practice, just make sure you're here by 4 to cook and clean. Do NOT be late.
This was where Billy had been going recently. To the house of some mom, where he would cook, clean, and as Anna read through more of the texts, do a lot more than that. Messages mentioned gardening, and cleaning the pool… Billy was Karen’s property. But juiciest of all… It looked like Karen had knocked Billy out. Maybe more than once. In fact, it looked like Billy was afraid of her.
Did she have **** over him? Or was she just that good, that she could make him do whatever she wanted for fear of getting knocked out yet again?
Whatever the case, Anna was glowing, her eyes wide and her mind blown. Her older brother’s big secret was all hers. Which brought her back to that recent message from Karen, which Anna now read, her hands trembling with delight.
Karen: I hope you learned your lesson from yesterday’s beating. I bought Selena a new plasma TV for her bedroom, and you’re going to install it for us.
Oh fuck. This bitch OWNED Billy. Anna shuddered as she read the casual, dismissive way Karen talked to the star athlete.
Anna was starting to get an idea of who this woman was, now that she knew she was a mom. Anna had seen a woman named Karen at some of the school fundraisers and events, a blonde woman who always wore a sneer on her otherwise beautiful face. She had to be in her 40s, and though she had the kind of trim body you can get with a wealthy life, she certainly wasn’t the kind of woman you’d expect to beat a young man at boxing. Let alone one as accomplished as Billy.
As far as Anna knew, Karen was a total bitch. Wealthy as fuck, but a serial complainer. She’d whined and whined when Anna was chosen to represent the school at the public speaking competition, over “her sweet Selena”. Anna had heard Karen snarl that “Heather’s brats” always got special treatment.
Fuuuccckkk, that was hot. Not only was Billy knocked out by a middle-aged woman… But it was one who hated him. A wealthy, beautiful, bitch of a milf who wanted everything for herself. KOing a boxing champion, and the son of her hated rival, then turning him into a servant… Anna had no doubt that Karen was extremely pleased with how all of this had turned out.
And now she had Billy, under her thumb. Anna chewed her lip. This was hot as fuck. She had no idea how wrecked her big bro was getting behind the scenes. But more than that, she was ready to send more text messages as “Billy”. She just had to figure out the right angle to come at Karen with…
Anna considered her options. Should she humiliate Billy some more, like she was doing with the mystery girl? Or maybe, should she challenge Karen’s authority? Anna had no doubt that this smug milf would explode if Billy suddenly stopped being so submissive towards her. Karen was the kind of woman who wanted everything, and never wanted to lose one of her possessions. Getting any kind of pushback from Billy could lead to glorious results.
Karen was a rich bitch, who always stuck her nose where it didn’t belong… And finally, Anna knew exactly what the best way to embarrass Billy some more was. The best way to ruin his reputation even more than it already had been.
Anna began typing “Billy”’s reply, and sent the message. The bitchy milf on the other side had no idea she was actually speaking to Billy’s little sister right now, as she read the text and began typing a reply of her own…
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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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