Anna manages to send Billy to Karen’s den

Anna was clever, and knew just the right ways to manipulate her older brother. Using the knowledge she gained from reading that message history with Karen, she came up with an idea of how to get him to go to Karen’s house.

The first step was leaving Billy’s phone in her room, and racing downstairs. Billy was sitting at the kitchen counter, eating lunch, when Anna approached him. He tried to ignore her, but that fell apart when she spoke.

“Hey, bro,” Anna grinned mischievously.

“What do you want, Anna?” Billy groaned. He was still nursing a headache from the previous night, and still soaking in the humiliation of getting smothered out by his little sister.

Losing to her was already bad enough. But losing to her ASS? That was fucking life-changing.

Anna tried to hide her excited giggles, but not THAT hard.

“I just got a text from a woman named Karen. She’s asking where you are, and she sounds mad~” Anna teased. “Is SHE the one who’s been kicking your ass?” Anna asked, acting like she knew less than she did.

Billy’s blood ran cold. Karen was asking for him? Oh, fuck, he couldn’t let Anna know what had been going on between the two of them. If Anna’s ass-smother was life-changing, letting her know he’d become a servant to a rich bitch milf after getting KO’d in front of a crowd was life-RUINING.

“N-No…” he stammered, uncertainly. Anna laughed.

“She sounded pretty mad. Why haven’t you been responding to her messages?”

Billy’s heart pounded. Oh, shit, had Karen been trying to reach him? He hadn’t had his phone all day. **** to not make Karen mad, and equally **** to end this conversation with Anna, Billy sprang up from his seat.

“I… I can’t find my phone, I… P-Please, Anna, tell her I’ll be right there! Tell her I’m sorry!” Billy said, sounding **** and hurrying to get ready as Anna laughed at his pitiful reaction.

In all the concern of having upset Karen, Billy didn’t stop to think how the wealthy milf could have possibly gotten Anna’s number to send those texts. All he was thinking was that he had lost his phone, and Karen thought she was being ghosted. He had to make things right.

He was nearly out the door, when Anna added one more comment.

“She wanted you to bring your gloves,” Anna smiled.

“She did? Why? Fuck!”

Billy knew what that likely meant. Was Karen really trying to box him again today, of all days? He raced to his room and grabbed a pair of boxing gloves.

“She says you’d better show up wearing them, or you’re in biiiig~ trouble,” Anna teased, really struggling to restrain her giggles now.

“Tell her I’ll be there soon!”

“Sure thing, bro…~” Anna cooed as she watched Billy race out of the house. He threw the boxing gloves into the car, jumped into the driver’s seat, and took off towards Karen’s house.

Wow, that was easy. That clever little sister had just sent Billy to certain doom, at the hands of an unforgiving milf.

But it wasn’t enough for her.

Now with the home all to herself, Anna casually strolled back up to her room, and jumped into her bed. While Billy was on the way to Karen’s place, Anna continued sending messages, stirring the pot.

Anna smiled as she laid back on the bed, typing away on Billy’s phone, putting her older brother in deeper and deeper trouble with each message to the wealthy milf who owned him.

“Billy”: You’ll never put me to sleep. It’s impossible. You’re just an old bitch.

“Billy”: Stupid rich bitch hands, never worked a day in your life, and you think you can cold-cock ME?

“Billy”: I’m going to enjoy toying with that trim body of yours after I put you the fuck to sleep. I’ll claim every part of you, and you’ll be too knocked out to stop me.

“Billy”: I’ll squeeze those fucking tits, I’ll kiss those pretty lips, and I’ll smash that tight fucking pussy too, while you just groan and sleep underneath me. You’re nothing but a slumber queen, waiting to lose.

“Billy”: You’re going to be mine. Defeated and claimed. You fucking hag. You’ll never touch my chin’s sweet spot. You won’t even get close.

“Billy”: The slumber queen is going down, hard.

Anna giggled with each message. Karen didn’t stoop to reply to any of these new texts, but the read receipts gave away that she saw each and every one of them, growing more and more enraged with each new taunt from her servant.

She hated being stood up to, especially by such a shitty peasant. Heather’s brat son was getting too confident, forgetting his place. Karen couldn’t wait to hammer him right in that landmine nerve cluster he had been talked about on his chin, and send the shocked brat down to the floor.

How dare he talk to her that way?

A few minutes later, Billy arrived. He rang the bell beside the large front door of Karen’s house, then doubled over, hands on his knees, panting for breath after the long sprint up Karen’s extravagant driveway.

Hearing her footsteps approach, Billy was barely able to gather himself enough to pull his boxing gloves on over his hand before the door swung open, revealing an angry, scowling Karen.

Billy felt himself shrink underneath that Karen scowl. This wasn’t as pleasant as the time she had opened the door wearing nothing but two towels on her elegant body - this time, she was in a sports bra and tight yoga pants, accentuating her curves… And she was gloved up, ready to box.

“I’m going to beat you senseless,” she snarled.

“Wh-what?” Billy stammered, his throat tightening.

“Oh? Did you think you could talk all that shit and get away with it, you brat?”

Billy’s heart raced. Was she that upset about the “typical Karen” comment the other day?

“I… K-Karen, I…”

“Not such a big man now,” Karen smirked those pretty lips of hers, feeling supremely confident now that she saw Billy’s meek posture. It seemed that basking in her presence had reminded him of just how hard she could beat him down. Not that he’d get any mercy for his sudden cowardice. “Get in here. There’s a weak chin I have to crush.”

Before Billy could reply, Karen reached out through the doorframe, taking him by surprise as she brushed her gloved fist over the right side of Billy’s chin. The unexpected touch stunned him, making him shudder.

The bitchy milf gave Billy’s chin a gentle pat, a smug expression on her face as he seemed to wince from the delicate touch of a boxing glove to his chin. It seemed the boy really did have a landmine buried in there… A sensitive cluster of nerves that could spell the end for him.

Billy didn’t understand the slow, delicate touch, but he was too stunned and too afraid of saying the wrong thing to even move.

“Thaaaat’s the spot…” Karen purred. “Are you ready to lose? I said get in here.”

With that, her cold scowl returned, and she turned around and marched inside. Billy hesitantly followed her, all the way to that home gym area he’d cleaned for her before. Where her personal trainer had done a basic boxing class with her.

Why was she so mad at him? And… Oh, fuck, was he even ready to have a rematch right now? He was sure his skills had only dulled since their first fight, and he’d gotten pretty badly battered just yesterday… Was there any chance Karen might show him some mercy?

And if not… What would happen? For fuck’s sake, she was just a middle-aged bitch. She had **** over him, sure, but… Even if he had gotten weaker, she shouldn’t be able to beat him. She just… Shouldn’t be able to!

She was a rich bitch in over her head. She thought she was all that, but she didn’t know the first thing about boxing! Billy was a young stud, a hungry athlete, with prodigal boxing skills and a sharp mind. He could crush any milf like an aluminum can.

So why was he shaking, as Karen turned around to face him, and raised her gloves?