Aunt Judy, And She Has A Challenge

“Billy?” Aunt Judy asked, peeking her head through the door as it slowly creaked open. “Are you still… awake?”

Aunt Judy pursed her lips together in excitement. Her sister had gone to bed after drinking more wine than she could handle, and Aunt Judy had a fair amount herself. When Heather fell asleep in her living room chair, a somewhat-**** Aunt Judy helped her sleepy sister to her bed and prepared to call an Uber home, when she stopped, eyes catching on the bedside table’s boxing gloves.

Heather had proudly shown them off to Judy not that long ago. The gloves that knocked out her nephew. Twice. Aunt Judy gulped as Heather gave her a full tour of their surface, even letting her hold one.

Now, Aunt Judy glanced at Heather, conked out in her bed. The story had been so exciting. And in her wine-addled state, she wasn’t herself. Aunt Judy put one of the gloves on.

“Wow…” she breathed, staring at the boxing glove now on her hand. It fit perfectly. She threw a few punches at the air, making her breasts jiggle. She had never thrown a punch before, and her technique was terrible. Even if she hadn’t been drunk, the punch was all in the arm, using none of the massive power she could generate from her mature thighs and hips. Still, to her, it felt great, and she giggled, feeling like a powerful woman.

Shooting another look at her busty, passed-out sister, Aunt Judy made her decision. In an excited rush, she put on the second glove and ran up the stairs, straight to her nephew’s room. She’d had too much wine to have much of a plan, but she knew that she’d fucking loved the story her sister had told her, and now she wanted to live it. Tipsy and eager, she wanted to box Billy. She came to knock him out, wearing those same gloves Heather showed her.

Now she stood at his slightly open door, biting her lip, excited to test herself out against him. Her nephew had always seemed so tough… Hearing about his moments of weakness in front of Heather got Judy so hot. She wanted the feeling of empowerment that came with knowing that she wasn't too old to hang with a younger guy in 'the ring'.

Had she been more sober she would have known that at her age there was no way she could even give Billie a run for his money, nevermind knock him out. But her current state stopped her from connecting the dots. She was adamant that she was going through with this, to hell with her complete lack of athletic experience. She hadn't even been to the gym once in years, and the only reason she was still in decent shape was the fact that she was eating healthy. But no amount of healthy food could turn an early 40s wine aunt into a championship boxer. What could do that, however, is quite conveniently a couple of loaded gloves.

“Hm? Aunt Judy? What are you doing still here?” Billy’s voice came through, and Aunt Judy’s heart fluttered. This was it. She had seemed to Billie as sober so far but that notion would be gone as she slurred through her next words. "I came here to challenge you!" She emphasized that last word by raising her right hand and pointing a glove at her nephew.

Billie immediately knew by how much strain his aunt had trying to lift the glove that she had the loaded gloves on. His mind raced as he considered the prospect of losing a match to his aunt. She would certainly brag about her triumph to the entire family! He would become the laughing stock of his cousins, a supposed boxing champion who was put on his ass and went out like a light by a couple punches by some untrained milfs.

What made this worse was that he knew that his aunt had been drinking. The only possible thing worse than losing a boxing match to an older woman with no experience was losing to her while she's not completely sober. There was absolutely no way he could explain this to anyone. He could just say that he was taking it easy on his mom the first time, that he got distracted the second time, that she got in a few lucky shots. How would any of this make sense to anyone? There was no way he would go through with this.

"Aunt Judy you're obviously drunk, why don't you go back down and wait for me to call you an Uber?"

"Uh uh, no way. You're not getting out of the match this easy. We're doing this before I leave."

"Aunt Ju-"

"No. Stop right there. Your mother said she knocked you out twice. I want to give it a shot."

Billie was getting irritated. His aunt was being completely irrational! If she knew that the gloves were loaded, maybe it would make some sense for her to be pushing for this. But she was blind to that fact! Did she really think she could take him even in her condition? Did she know something he didn't? Had his mom found out about the weights and told his aunt about them? Billie started getting more and more nervous as he tried to come up with a reason his aunt was so confident. Was he... was he actually scared of boxing his aunt?

Billie cursed his stupid mind for feeling like this. Then he realized something truly terrifying. His heart was beating faster than usual, and he felt a slight pit in his stomach. His entire body had internalized his unfounded fears of being beaten by his aunt.

Billie was internally screaming at himself. "She's just a tipsy old woman. She has no experience boxing, she throws weak punches, she has NO business in the ring with an ACTUAL boxer. WHAT THE FUCK ARE YOU SCARED OF?"

Billie started shaking away the fears as he realized that aunt Judy was not a credible opponent, and more importantly, he didn't even have to box her. He'd just stand his ground and tell her to fuck off. What could she do, restrain him and **** him to put on his gloves and box her? Billie started to regain his confidence as he prepared to confront her into dropping the matter.

"I'm calling an Uber." Billie turned away to grab his phone from

"Hold on there. You wouldn't want the entire family to find out you pussied out of fighting your own aunt because you were too scared, now would you?" Billie paused and looked back at his aunt. "It's fine if you don't want to fight me, honey. It really is. But it would be such a shame for all your cousins to learn about how big bad aunt Judy had scared the socks off of 'boxing champion' Billie so bad that he backed out of a fight with her. What would they think of you?" He took in this new information as he kept silently staring at the mature women standing by his bedroom door. "I might even throw in the fact that your own mother put you out a couple times. Maybe that will give them an idea of why you were so scared!"

"Enough!" Billie decided to put an end to this once and for all. "You want to box me? Fine, but after I beat your ass all over the living room don't start crying about how badly I destroyed you." He had gotten very mad at the cocky attitude aunt Judy was displaying.

"Big words from someone who is 0 in 2 against an older woman!" He couldn't believe it. She was trash talking him! "Fuck you," he spat back. "I'm afraid it is you who's going to be fucked." She raised both her gloved fists and stuck them on her wide hips as she stared daggers into her nephew. Billie knew that she had won the war of words, and it slightly intimidated him. But there was no backing down now. He had to shut her up once and for all.