Aunt Judy housesitting

It was only a couple of days before Billy saw Aunt Judy again. The second woman who had made his cock so hard and outboxed him twice over. So soon after his impromptu back garden dreaming session, he would again be in the company of a milf who punched his lights out. And it was to be for a surprising extended stay.

Heather had to leave the state for a few weeks on a surprise business trip. Despite Billy’s explanations that he was old enough to be home alone for all that time, his mom insisted that someone more mature be around to look after him. Enter Heather’s sister, Aunt Judy. Mature was the perfect word to describe her, at least physically. And she packed one hell of a punch.

“Mom, really, I’ll be fine on my own!” Billy insisted, as Heather was heading out the door with her packed luggage.

“I knocked you out.” Heather said bluntly as she set her suitcase in the trunk. “What I say goes.”

“But mom… Come on! I’m 19!”

“I knocked you out twice.” Heather repeated, stepping into her car. “You get on fine with Aunt Judy anyway. Stop being such a baby. She’ll be here around dinner time, and she’ll be sleeping in my room until I get back. Show her the respect she deserves.”

With that, Heather drove off for the airport, leaving her irritated son behind. He hated how she held those defeats over his head. Just because she’d put him to sleep a couple of times while sparring… He was still a champion! Where was his respect?

Still, his mom was convinced she had knocked him out legit, and there was no changing her mind. About that, or about his need for a house sitter. Billy stomped back inside. If only he’d never given his mom that first boxing lesson, none of this would’ve happened.

Aunt Judy was the last person he wanted to see right now. Sweet and apologetic or not, she’d still kicked his ass, and having her “look after” him was going to be totally humiliating and awkward. It also meant no parties while mom was gone.

At least those damned gloves were gone. Billy could rest easy knowing that he wouldn’t be getting sparked out by an older woman again for the rest of his life. From now on, he could just admire his mom and aunt’s sexy bodies, and think back on only the good memories from his losing streak whenever he wanted to stroke himself to completion. Sitting in a place of safety as he remembered the old days, when he fell to their feet ****, as a loser. In fact, the hours he had before Judy arrived seemed perfect to do just that. And so that’s what Billy did.

“Billy! How have you been!” Aunt Judy greeted him at the door just before dinner time, as promised. She had a broad smile on her face, and spread her arms wide to greet her beloved nephew, with no idea that he’d just shot semen thinking about the times she’d drunkenly knocked him out.

Billy **** a weak smile onto his face as she stepped inside and took him into a big, squeezing hug. He tried and failed to not get hard as her breasts pushed into him. It was just another reminder of what a goddess his aunt was.

“No more mommy knockouts?”

The question took him by surprise. Aunt Judy’s whisper went straight into Billy’s ear as they hugged, sending a shiver down his spine. He could feel her soft breath of his earlobe.

“She’s been letting you stay awake, right?” Judy continued in that same quiet, accidentally-sultry whisper as she inquired about his dark secret directly into his ear. Billy’s heart beat faster against her soft chest.

“W-What? No… No, there haven’t been any more…” he stammered out.

“Goodie!” Aunt Judy smiled, pulling out of the hug. “I was so worried, picturing you drooling in your bed from her punches. I’m glad you aren’t getting put to sleep. I really thought she might have made it a nightly tradition to smack your chin.”

She had a bright, beaming smile and a genuine look of relief on her face as she said that. It sounded genuine, so Billy timidly stammered out a thank you for her. Judy was so naive about fighting, and what was and wasn’t humiliating to say, that sometimes she ended up making Billy out to be some weak little KO toy for any mature woman to enjoy. Billy, the club champion. He was so glad his classmates didn’t know about any of this. He wouldn’t be able to take that humiliation.

That was when his cheerful auntie lifted up a bag for Billy to see. His eyes grew wide as he stared through the translucent plastic.

“Guess what I broouughttt~?” she sang pleasantly.

Billy’s heart sank. She had brought the gloves with her.

“B-But… I thought you had…”

“I was going to throw them out, but then your mother called and said she wouldn’t be home for a few weeks, and needed me to look after you. Since she won’t be around to knock you out with them, I thought we could get rid of them together! That should make you feel safer, right? To actually see them get thrown out?”

Billy’s mouth was dry. He couldn’t pull his eyes away from the harbingers of his many, many defeats.

Aunt Judy’s lips pursed as she saw her nephew’s fearful reaction.

“Oh, Billy… Here, look! They’re already gone!”

She marched over to the dumpster at the front of the house and made a show of displaying the plastic bag before dropping it inside. There was a heavy “thunk” as the loaded gloves hit the bottom. All Billy could think was, if that had been dropped on him, would it have knocked him out?

Aunt Judy dusted off her hands.

“See? Now you know you’re safe!” she smiled at him.

“Th-Thanks…”

“I ordered a pizza for our first night together. It should be here in about half an hour. Until then, how about we have something to drink? We can finally celebrate the end of you getting knocked out in sparring matches now!”

Billy tentatively agreed, trying to ignore his aunt’s embarrassing way of describing things. He wasn’t 21 yet, but Aunt Judy waved that off.

“Come on. You’re an adult, Billy. You can have a few glasses.”

And so, the two of them sat down in the kitchen, and Aunt Judy poured them each a glass of red wine to drink as they waited for their pizzas.