He tells her about Karen

“…Karen…” he admitted, sadly.

Anna smirked, a wicked glimmer in her eye. She knew she could draw the answer out of him eventually. This late-night visit had been so worth it. But still, a question remained…

“Who’s Karen?” Anna asked.

Billy’s big, pleading eyes stared up into Anna’s confident gaze.

“She’s the one who knocked me out that night,” Billy continued. “She’s… She’s a blonde woman who-“

“Wait, Karen the MOM?” Anna gasped, interrupting her older brother as the realization hit her. “Like- that mom who shows up to school functions and stuff?? You got knocked out by KAREN??”

Anna’s mind was reeling at the possibility. Karen was an incredibly wealthy, incredibly bitchy, older woman. Middle aged. Anna only knew of her from a handful of very limited interactions, usually where Karen was making some kind of loud complaint at a school fundraiser or event.

One particular memory stood out, when Karen had made a scene about Anna being chosen to represent the school at a public speaking competition. Apparently, Karen believed that her own daughter was more deserving, despite Anna being the clear frontrunner. Anna was pretty sure she had heard Karen snarl something about “Heather’s brats” always getting special treatment.

Anna was sure Karen had it in for Heather. Heather was gorgeous, cheerful, well-liked, and the mother of an intellectual prodigy of a daughter and an athletic prodigy of a son. By all accounts, Heather’s life was perfect, and Karen hated that. She viewed anyone else’s success as a challenge to her own, so someone like Heather and her kids were seen as hated rivals.

Had Billy really gotten himself knocked out by fucking KAREN, of all people? Holy shit. How had she not gone around telling everybody yet?? Anna would have thought Karen would let the whole world know, if she had managed to humiliate Heather’s son at the same time as she accomplished something as personally impressive as outboxing a young athletic champion. This seemed like exactly the kind of situation Karen strived for. Looking good as fuck, and making a “rival” look worthless.

“She… She’s really fit…” Billy mumbled, trying to defend himself. Anna burst out laughing.

“Holy shit! KAREN knocked you out??” Anna repeated, as Billy confirmed that she had the right woman in mind. She couldn’t believe what she was hearing. “Oh my god, tell me EVERYTHING!”

Anna was almost shaking, she was so excited. She needed to know exactly what went down. How Billy could have been put to sleep by a wealthy blonde middle-aged woman, who wanted everything for herself. A sneering bitch of a milf with a gorgeous face and a trim body. Karen was fit in a rich-and-does-yoga kind of way, she certainly wasn’t the kind of woman you would expect to beat a young man at boxing - let alone one as accomplished as Billy.

Anna giggled again, picturing Billy flopping **** at that entitled woman’s feet. Oh my god, that was too good. No wonder he’d been trying to keep it a secret! Anna had expected some high-level female boxer at his club to have taken him out, not some untrained bitchy mom!

“…She was trying to figure out if her daughter should join the boxing club, or if it was too dangerous,” Billy began to explain. “Sh-she made me give her a free punch… I just had to stand there and let her hit me in the face.”

“And she put you out??” Anna gasped. “Holy shit, she knocked you out in ONE PUNCH!?”

Billy shook his head, his lips dry. “N-No… No, I took it… I was okay…” he continued. “E-Everything was fine, but I guess she saw something she liked after that first punch, because she challenged me to a fight…”

Anna’s eyes went wide. KAREN had challenged BILLY? Holy shit.

“Sh-She was really confident, too… She kept asking if her one free punch had broken my brain, or slowed me down, something like that,” Billy moaned. “Eventually I agreed to fight her, just to shut her up. It started out well. She didn’t know what the fuck she was doing. Her footwork was awful, and her punches were wild. I was just circling her, jabbing her up, making her look stupid. But… As the fight went on…”

Anna held her breath, as Billy told her about what Karen had done in the fight. The back-and-forth momentum, how she had worn down his arms. Obstructed his breathing. Pushed him into the corner. Billy hoped that, by giving a long, detailed account of the fight - treating that as the whole story - Anna would forget to question the circumstances leading up to the fight. All her questions would be on the details of the match, because that was where all of the story took place.

Anna listened intently, more focused than perhaps she had ever been, as Billy weakly recounted the details of how Karen had put him to sleep. He left out some of it, of course. He didn’t mention the video. He didn’t mention the **** deal Karen had him tied up in since the devastating knockout. He didn’t mention the audience of moms watching it all happen, or that he was supposed to teach them and Karen in a boxing seminar.

But Anna was a curious girl with a lot of questions, trying to form a detailed mental picture of her brother’s lost fight. Under Anna’s precise questioning, Billy eventually gave up some of those details. Better to embarrass himself than to have Anna doubt his story, he thought. Besides, he didn’t have the mental strength to resist his clever little sister at this moment. And so, Billy eventually told Anna that this fight took place at a boxing seminar for moms of the school, one that he was meant to be running, and that a crowd of other moms had seen everything Karen did to him.

“A whole CROWD?” Anna gasped in amazement. “Why haven’t I heard about this?? Oh my god, Karen knocked you out in front of a whole CROWD of moms??? At your OWN seminar!?!”

Anna’s face was beaming with delighted glee. Billy had never seen his sister so joyful. With a weak, shuddering moan, he nodded.

“Yes… They were all watching…” he groaned. “I wanted to finish Karen and get back to teaching, but… I couldn’t… I just couldn’t beat her…”

Anna was subtly grinding her pussy against him now, leaning on his every word.

“Everyone just packed up and left while I was still asleep, after Karen knocked me out… We hadn’t even started the seminar yet…” Billy shuddered. “I woke up, a-and… I was all alone, lying in the ring…”

This was amazing. This was everything. Her prodigy of a big bro had gotten taken out, by a bitchy mom, in the most humiliating way Anna could ever imagine. With EVERYONE watching him fall! She wondered again, why hadn’t Karen told the whole world about this already?

Anna might have felt bad her him, if she wasn’t still riding the high of her own victory that night. Hearing Billy’s humiliating story was just erotic fuel for her at the moment - sympathy was for other, less invigorating nights. This night, all Anna wanted to do was rub this in her big brother’s stupid face.

Anna quirked her head, smiling down at Billy.

“So… With everyone watching, you just couldn’t do it?” Anna asked. “You just couldn’t keep awake?”

She reached out, patting the top of his weary head with a giggle.

“That brain just couldn’t hold on? What a quitter.”

“Ohhhh…” Billy moaned dumbly, automatically pushing his head into Anna’s comforting hand and making her giggle even more.

“Karen fucked you up, didn’t she?” Anna laughed.

Billy nodded, slowly, with another shaky moan.

“Sh-She wore me down… She outboxed me… She outlasted me… She made fun of me and teased me, while she battered my head around, until I just went to sleep…” Billy shuddered, remembering how hot Karen had looked. “She broke me… She was terrible at boxing, and she broke me…”

“Then it sounds like she wasn’t so terrible at boxing,” Anna smiled. She reached out and placed a condescending fingertip against her older brother’s forehead, and continued. “Don’t be a sore loser. You’re the one who got knocked out. If anything, YOU’RE terrible at boxing.”

Billy shuddered and moaned pathetically, making Anna giggle. She thought back to how Billy had said that Karen drained his strength, by obstructing his breathing during their fight - how she had pressed his face into her chest, and how she had squeezed the air from him in a milfy momma bear hug. It wasn’t so different from what Anna had done to drain Billy’s strength during their impromptu wrestling match. It seemed like her big bro was a slow learner.

A popular, handsome prodigy, who just couldn’t last. Not against his mom. Not against his little sister. And not against a bitchy milf.

Anna beat a quick drum rhythm on his chest, the excited rata-tat-tat of a very satisfied girl.

“Thank you for being so honest with me… Eventually,” she snorted. “I’ve got a lot to think about. I’ll let you get back to bed. But this was fun. We should do it again.”

“Noooo…” Billy moaned weakly, drawing a chuckle out of Anna as she lifted herself off of him - freeing his exhausted arms at last. They fell uselessly to the sides of his body, too weary and heavy to lift.

“We’ll just have to see,” Anna said, walking towards Billy’s bedroom door. “Maybe you’ll be honest with me from the start next time I have a question. Nighty night, bro. And sweet dreams.”

With that, Anna left, swaying her cute, satisfied hips as she walked down the hallway to her own room, leaving Billy weakly laying on the floor. The nerdy girl felt extra smug after that tremendously successful nighttime visit. Anna would have to work out some of those feelings of power with her fingers, once she was in her own room. Her pussy was feeling very, very needy.

Even with her gone, Billy was just so exhausted, so worn down… He couldn’t even find the energy to get back up and crawl into bed. And so, finally left alone, Billy just let out one final weak moan and closed his eyes, allowing himself pass out on the carpet.

“Ohhhhh…”

His bedroom door was left open as he drifted off, leaving quite the scene visible from the hallway outside his room. A messy bed, with sheets hanging half-off of it from the earlier tussle, and Billy himself flopped out cold on the floor, dreaming through the night - totally dominated by his younger sister. His limbs splayed awkwardly, and his mind far away, as his body slowly went into recovery mode. Outwrestled, outsmarted. Smothered to sleep in a plump nerd ass. Beaten ****. And **** to share his deepest humiliation. Laid out like a chump.

He had given Anna exactly what she wanted. Now, all he could do was sleep.