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Chapter 19
by
Raljo
What's next?
Aunt Judy’s favorite sport
Billy was trembling as Aunt Judy opened the door to his room. Poking her smiling, wine-blushed face through, she found him tensed up, already wearing his own gloves and holding them up defensively.
“Please… Please don’t make me box you again Aunt Judy…” the club champion quietly begged.
He was shaking. Was he a better boxer? Absolutely. But the mental damage of being knocked out not once, but twice by this drunken, doting milf was massive.
Aunt Judy smiled, and stepped inside, closing the door behind her. Billy gulped. Even now, scared as he was, his dick was rock hard for her as he got an eyeful.
As in their last match, his Auntie was stripped down to her bra and panties, plus those blue loaded gloves which covered her dainty fists. Her big round tits jutted out, their deep cleavage entirely exposed, just as most of her perfectly formed, mature body was. Her round, perfect ass. Her flat belly. Her long, smooth legs. She had legs for days. If she even knew how to throw a proper punch, if she had some proper training under her belt, those legs and broad hips would make her a knockout artist anyway. Not that her luxurious lifestyle gave her any reason to pursue anything so brutish as fighting, outside of her fun little matches with her nephew.
Billy stared at this mature goddess’ body. He knew he was going to have to knock her out before she got to him, if he wanted any hope for his future. Round One was about to start. He couldn’t go down. He couldn’t get put to sleep again.
“Alright bitch. I’m gonna knock you out!” Aunt Judy pointed at him with a glove, then charged.
The tipsy milf ran forward, nearly falling over as she threw a punch that never would have landed even if Billy hadn’t frantically dodged backwards. Sloppy punches rained towards him, each of which he either avoided or blocked. With the loaded gloves on, those blocked punches were still heavy on his arms, but at least they weren’t loss-inducing. And they had to be tiring her out too, right?
After a few quick shots were all blocked in a row, Aunt Judy paused to laugh, pulling a few steps back and watching Billy with a smug look. All she knew was, earlier he’d been dodging, and now she was hitting him - she didn’t understand the distinction between a blocked punch and one that made it through, so in her mind, she was pounding him out at the moment.
“Had enough!?” Judy taunted gleefully.
Billy set his jaw. He tried to calm himself down.
He was a boxing champion. This wine-blushed, busty older woman was at best a royal amateur. She might’ve watched some YouTube to learn more of the very basics, but she very clearly still had no idea what she was doing. No idea at all.
To her, boxing was a fun little game where at the end of it her nephew was asleep. A game she didn’t know the rules to, but always seemed to win anyway. She didn’t understand the art of it, the techniques, the ringcraft. She just knew that Billy got praised for always winning and being oh-so impressive, yet she could beat him. She just knew that it made her feel good.
Billy wasn’t about to suffer another newbie knockout at this naïve woman’s hands. He wasn’t about to let her put him to sleep without even understanding how she did it. He wasn’t about to become a third feather in her cap of pride and self-gratification. He was a goddamned champion, and he was NOT going to be finished off by a drunken, middle-aged milf who’d watched a few YouTube videos about boxing!
“If you’re just going to let me pound you out, it’s no wonder you got knocked out by your mommy too!” Judy laughed.
With a roar, Billy charged forward, ready to jump on her and start swinging rapid, but precise and powerful punches into her until she shut up. She didn’t have any technique, so he didn’t bother with the usual safeguards. He would take her by surprise and flood her until she quit.
Unfortunately for him, Aunt Judy’s bedtime boxing into the mirror had given her one actually-good punch - the only one she had in her arsenal, copied straight from a YouTube video - a counter left hook as your opponent rushed in. It was the one punch she’d drilled in the mirror the most. She liked the way the twisting of her torso made her boobs move. And that was exactly the punch she threw out in response to her angrily-charging nephew.
“BLEH!”
The punch caught him on the chin, landing flush. And then it was lights out. The last thing Billy saw was his gorgeous Aunt’s leering face and big bouncing boobs as she wound up for the punch that put him down hard.
Thrown off his forward momentum by the shot, Billy was thrown over to the side, arms waving like limp little noodles as his already-**** body did a half-spin before he flopped down onto his back. He landed with a crash, limbs flopping down. Poor Billy was laid out on the floor again, snoozing away. And just like that, Aunt Judy was 3-0 as a fighter.
“YEAH, EAT THAT!” she roared with triumph. “YOU’RE KO’D, BITCH!”
Aunt Judy felt that familiar rush of satisfaction, pride, and power. Her strong, athletic nephew was sound asleep from the shot she had thrown over and over into the mirror, for no reason other than her sober self liked the way it made her chest move when she spun her torso. A habitual technique her drunken self had taken full advantage of.
He was done for. Her naughty knockout left Billy drooling like a little bitch, stopped short by his auntie in his very own bedroom. It was delicious, the way his body landed all crumpled up and sad looking. Defeated by an older woman. An apparent boxing prodigy getting slept by an even bigger prodigy. A milf.
Aunt Judy took off one glove, using her now-free hand to squish Billy’s cheeks together and shake his face around, before picking up her glass of red wine again. She sipped some more of it, accidentally spilling some down her bra with the drunken sway of her hands.
“Oh…” she pouted, setting down the glass wiping at her chest with a hand.
Her fingers ran over the swell of her breasts, rubbing the liquid in more than she was wiping it away, leaving her with a pair of wine-scented boobs. Still, she enjoyed the feeling, touching her breasts as she stood over where Billy lay sleeping, wearing nothing but her bra and panties. She grinned down at her defeated nephew, crumpled on the floor with his boxing gloves still on his hands.
He was so still. So peaceful. She’d really pacified him. She’d silenced his roar. She’d knocked the fight right out of her nephew’s little head with that punch. The champ was finished.
That was so great. What a dominant win! He’d dodged a few punches at the start, but then he just started taking blow after blow after blow. Aunt Judy hit him with everything she had! And right when he tried to retaliate… BLAM! A perfect counter! Good night Billy!
“Were my combos too slick for you…?”
Aunt Judy threw her head back and laughed, towering over the defeated and motionless form of Billy. Then she spotted something out of the corner of her eye - Billy’s championship belt, in his wardrobe.
Aunt Judy smirked.
Billy groaned as he slowly came to. “Guhhh…” he blinked his bleary eyes, and looked around. He was still on the floor of his bedroom, wearing his boxing gloves. At first he didn’t know what had happened, but when he saw Aunt Judy in her underwear, bent over him with a flushed, grinning face as she slowly shook him awake, he guessed it well enough. She still wore a loaded glove on one hand, meaning that even if he hadn’t still been fucked up from whatever she’d hit him with, she was still a threat.
“Hey bitch…” she cooed, drunkenly not thinking to stop slowly shaking him by the shoulder with her free hand, even though she’d woken him up already. Billy stared down the dangling cleavage of her swaying, wine-scented boobs as she continued with a smirk. “I fucking knocked you out again…”
“Ohhh…” Billy moaned, mouth going dry. He could feel her hot wine breath on his face.
“You lost from my punch…” she cooed, hand still shaking his shoulder. “You couldn’t take it…”
“Ooohhhh…” he was still staring down her top, and groggy as hell. His cock was starting to stand up in his pants.
“Now…” she smirked. “You’re not sho much of a “champion” anymore, are you?”
“N-Nooo…”
Billy gasped as she put the knuckle pads of the loaded glove up against his chin, lifting his head up with it. She really had his attention now.
“Then go get me my belt.” Judy commanded, sternly.
Not having the mental fortitude to hold out any longer, Billy gulped and nodded, then crawled over to his wardrobe to retrieve his belt. Judy’s belt. She cocked a hip and watched, smugly, as he took off his gloves, picked up the gold championship belt, and brought it back across the room for his drunk boxer Auntie.
“Good boy,” she purred. Then she put her gloved fist under his jaw again. “Now put it on me.”
With a loaded glove fist on his chin, Billy was once again **** to do what his busty aunt wanted. With shaky hands, he reached up and put his belt around her waist, fastening it around her, just under her bulky, heaving breasts, touching her bare skin as he did so.
Fuck… he got knocked out again. He got finished.
“Mmmnn… That’s right, boy.” Aunt Judy started a slow, swaying dancing, arms up in the air in celebration. Billy stared. She brought her arms down to rub her new championship belt, with both the one loaded glove and the other hand’s dainty, manicured fingers. “I’m the champ… I’m the undefeated boxing champ of this house…”
Without warning, she twisted her body and threw that same left hook she drilled, right into an awestruck’s Billy’s cheek, knocking him out cold again with a thunderous punch. He never saw it coming. WHAM! Billy went from being on his knees to being back on the floor **** in no time flat.
“…And you’re nothing but a jobber.”
She never could have imagined this a few weeks ago. The undefeated Boxing Champ Billy, pride of all family gatherings, getting KO’d by his busty, half-naked, drunken auntie, as she wore his belt. Getting flattened out limp in his own bedroom, his leg twitching before going totally still at the feet of this hot bod boxing newbie. A totally clueless middle aged woman. Albeit, one with a new amateur record of 3-0.
Billy. Was. Knocked. Out. The champ had gone 0-5 against untrained milfs. All losses by knockout. His weak chin couldn’t handle his auntie’s fist kisses without going night-night. And now he was on the ground, limp as can be, snoozing away and deep in a happy little dream at the feet of the real family champion.
What's next?
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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