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Chapter 42
by
Raljo
What's next?
Anna texts her back, as Billy
Anna made her decision. She was too excited, and too horny, to make any long-term plans. So instead, with her heart fluttering, she gave in to her desires. This was a rare opportunity for Anna to talk with a girl who had beaten Billy, and who enjoyed humiliating Billy, and who believed that Anna WAS Billy.
Anna liked humiliating Billy too. And so, still not knowing exactly who this girl was, she began typing up a message. She was going to text Carly back, as “Billy”, acting woozy and weak and fucked up.
“Billy”: We can’t have a rematch yet. I need some time to recover.
Anna’s mouth was dry as she stared at the screen. The conversation had ended a while ago, and it was late now, so she likely wouldn’t see a reply. But then those three dots appeared, telling Anna that the mystery girl was typing, and Anna’s heart soared. Apparently, Carly was too amped up to get much sleep either.
Anna’s heart thumped hard in her chest. She was **** to see what kind of humiliating insult this mystery girl would have for her older brother.
Unknown: XD damn right u do! wait, so are u admitting i fucked u up? are u admitting ur chin got stolen by a girl?
Anna squealed with glee. This girl was perfect. Perfect! Excited to continue, the young girl began quickly tapping her reply. Sitting on top of a sleeping, drooling Billy, wrecked by his younger sister’s fat ass, as she texted his apparent rival with the goal of making a fool of him.
Billy’s legend had taken some hard knocks recently, and Anna wanted to ruin her older brother’s reputation even more.
“Billy”: You got lucky. I didn’t expect you to be so much faster than me. It took me by surprise.
Unknown: omg just fucking admit it. admit i kicked ur ass!
Anna licked her lips. Her response to this message had to be perfect. Should she deny it? Admit it, already? It felt a bit too early to make “Billy” admit defeat. So maybe…
“Billy”: Look, to be honest, I don’t really remember the fight. And I have a really bad headache. But my friends told me you didn’t knock me out, so you can’t have beaten me that badly.
Anna smiled, grinding her pussy against Billy’s **** body. That was perfect.
Unknown: OMG, did i wreck ur brain or smth? u cant even remember the fight?
“Billy”: No. I remember that you were faster than me, and that’s it.
Unknown: LOL! billy, ur such a little bitch. i didnt think i hit u THAT hard! XD
“Billy”: Pleassss stop. My head hurtsss.
Anna was mewling like a **** kitten in real life, as she finally gave in to making “Billy” appear as though he was still reeling from whatever this girl did to him.
Unknown: omg, i fucked u up. all u boxers are such pussies. kickboxing is where its at.
“Billy”: Boxing is just a sport. You’re not supposed to actually fight so hard. You really hurt me.
Unknown: omg this is too good. ur brain is fucking cooked. I cant believe u just admitted that, LMAO. i must have pounded all the male pride out of your body.
“Billy”: Stopppp
Unknown: do u admit it? do u admit that I beat u?
“Billy”: Yesss you beat me. Fuck. I lost to a fucking girl.
Unknown: thats right~! lol, I never thought u would actually agree. so much for the undefeated champ.
“Billy”: It was just sparring. It doesn’t counttt
Unknown: whatever lol. I beat u
“Billy”: I was trying so hard. You shouldn’t have been able to beat me.
Unknown: LOL what happened to not going 100%? I knew u were trying ur hardest. doesnt make a difference. i basically KO’d u LMAO
It was then, grinding her steamy pussy against Billy’s chest, that Anna came. Squealing and cumming hard against her big bro’s collarbone.
Breathing heavy, Anna stood up, and walked back to her room, never looking up from the phone screen as she tapped away at it. Leaving Billy behind on the floor.
The conversation continued deep into the night, and through another two orgasms, Anna texting this mystery girl and making sure “Billy” admitted to all kinds of humiliating things. Being afraid of her, being stunned by her accuracy, thinking she was “too beautiful to punch that hard”, and more. When both parties finally went to sleep, with Carly feeling smug and deeply satisfied, and Anna feeling a similar way, Billy’s phone rested screen-down on Anna’s chest.
Exhausted from the late night, and the many orgasms, Anna slept like a log deep into the next day, while Billy slept on his own floor in the room next door. When he finally woke up in the morning, embarrassed to have lost to Anna, he was at least somewhat glad that she had seemingly given up on pulling a confession out of him. He didn’t dare enter her room, for fear of provoking another attack. Though surely, now that he was rested up and a bit less sore, a second wrestling match wouldn’t go the same way?
Damn, though… KO’d by Anna’s ass. That was the worst one yet. He’d just… Fallen asleep. He couldn’t even push her off. All she had to do was sit, and he was smothered. Drained. Wrecked. Into a deep, night-long sleep. Fuccckkk, he just knew Anna was going to be extra annoying after that. Billy struggled with the sense that his little sister may never respect him again. But he didn’t want to think about that right now. An elite boxer getting KO’d by a nerd’s plush ass was too much for him to deal with emotionally.
…Huh. Billy wasn’t sure where his phone was.
Had he left it at the boxing club? Or Karen’s place? Downstairs? Had it fallen behind the bed? Billy truly wasn’t sure, the bedtime conversation with Carly the last thing on his mind, overshadowed by the very memorable, humiliating encounter with Anna.
Damn. He would have to find his phone later. How annoying that he had misplaced it somewhere.
When Anna came to in the mid-afternoon, with that phone screen hot against her chest, she was immediately reignited with the need to continue having her fun. And so she sent the mystery girl the first text, still acting as Billy, and waited for a reply. She planned on keeping that phone to roleplay with for the whole day, maybe even longer. Saying all kinds of humiliating things, fingering herself with her free hand, laughing as the mystery girl took more and more pleasure in humiliating Billy.
Anna wanted to know more. She knew she needed to meet up with this girl, or message from her own phone, or at least learn her name. But for now, she couldn’t pull herself away from Billy’s phone, and this new, novel way of humiliating her older brother.
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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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