Chapter 20
by
Crushedone
What's next?
He sees the gloves, but not his mom
When Billy opened the door, the lights were dim. He could see the boxing gloves on the table next to his mother's bed, but Heather herself was nowhere in sight. Billy cautiously stepped into the room, looking all around for signs of his mother, but she did not appear to be there.
Where was she? The bathroom? The kitchen? Maybe she had even gone to pick up Anna and he hadn't noticed with how hard he had been wanking to her. Either way, the gloves were right in front of him and there was no one around to see him snatch them up. He might never get a better chance than this. Billy quickly tiptoed into his mother's room, careful not to make a sound. He made his way around her bed and saw the bane of his existence, the loaded gloves he had created. Billy picked them up, feeling the slight, but unnatural weight in them. He breathed a sigh of relief, and smiled.
"It's over..." he whispered.
"Can you repeat that...?"
Billy's heart nearly burst in his chest when he heard his mother's voice behind him. He whipped around, expecting to see her with a furious glare on her lovely face, but instead saw the bathroom door, luckily closed with a slight light peeking out from underneath. A moment later he heard her voice again, obviously not addressing him.
"I'm sorry, Judy. I need to put the phone down so I can try on these clothes. Anna had the right idea, I think I might need an update in my wardrobe. Let me put you on speaker," Heather said on the other side of the door. Billy let himself breathe again when he realized his mom was on the phone with his aunt. He was glad she had decided close the bathroom door or he would have been caught for sure. The young boxer knew he should have made a break for it then and there, but he was curious what his mother was talking to her sister about this late, and inched closer to the door to listen when his mom spoke up again. "Alright Sis, go ahead..."
"I'm still just trying to wrap my head around all of this," Judy's voice carried through the door, sounding extremely anxious. "Anna comes home from France, and after just one lesson, knocks out her boxing champion big brother. Then this morning she does the same to Billy's best friend, who immediately asks her out after he wakes up?"
"Mhmm," Heather hummed happily. Clearly she had left out some of the saucier details when explaining the recent events, but she was clear about what she felt were the most important details. "It was so adorable Judes! I wish you could have seen it! Apparently these two have been wanting to get together for years and it took Anna kicking his ass to make it happen. Beating her brother really raised her self esteem."
"I'm beginning to wonder about Billy and his friend," Judy replied suspiciously. "If they are as good as you say, then an amateur like Anna shouldn't have stood a chance. Are you sure they weren't just being nice and trying to make her feel more confident, or that this isn't all some cruel joke to mess with little sister?"
"Oh no, I can guarantee you it was all real," Heather answered smugly. "Billy and Matthew knew nothing about our little challenge beforehand. They had no time to plan anything out. I was just as surprised when Matt woke up and begged Anna to be his girlfriend, but I would like to think that they would have been together much sooner if not for Billy. I was so embarrassed when I found out about the mean trick he played on her. And Anna was furious! If I hadn't stepped in, I think she would have taken her brother's head off!"
Billy blushed as he felt himself get stiff from the memory of his sister charging him with fire in her eyes. He imagined her fist impacting his face and sending him flying like something out of a cartoon, only to crash land at her feet while she flexed over his smashed in face in those sinfully small shorts and shirt she had worn earlier.
Billy absentmindedly brought his hand to his crotch, rubbing his dick through the thin fabric of his shorts.
"From what you told me, you took care of that for her..." his aunt said with an annoyed tone. And yet, Billy thought he caught something else in her voice. Something he couldn't quite put his finger on, but made him all the more interested in their conversation.
"Now don't be like that," Heather scoffed at her sister's quip. "Billy is practically an adult, so I can't just spank him. But that doesn't mean he shouldn't be punished when he does something wrong. He is my son and I will punish him when and how I see fit for as long as he is living in my house. I would have been happy to give him a fighting chance. I think he has just come to accept the fact that his mommy can put him down anytime she wants..."
Billy bit his lip to keep himself from making any sounds. He wanted to tell her so badly that he could beat her in a real fight. That all of this was just some stupid mistake, and he really was the strongest person in the house. But he couldn't shatter his mother's fantasy without revealing his own. And as embarrassing as it was to admit, it wasn't like she was wrong. Billy didn't even think about fighting back this time. He walked willingly into his mom's waiting fists, knowing what it would mean and that a knockout was sure to come. Hell, in that moment, he had wanted it! He got a thrill from being helpless against her. How many times tonight had he cum to the memory of her gorgeous body dominating him as he hugged himself tighter into her enormous tits?
Billy rubbed himself harder through his shorts.
"I just can't believe that Billy is so weak. He always seemed so strong and confident..." Judy let out a disappointed sigh.
"Now don't be too hard on him. Billy is the top boxer in his age group. I've never seen him lose until he started training us," Heather defended her son. "It's just a testament to how gifted the members of this family are that Anna and I are the only ones who have been able to beat him. Would you believe that Billy actually admitted to his sister that he has always been intimidated by how good she is at everything, and was honestly afraid that she might beat him?"
"No!" Judy gasped over the phone. "He actually said that...?"
"It's true!" Heather responded with such confidence and pride Billy could practically see her smile through the wood of the door. "But after I took him out after just one lesson, it shouldn't be a surprise. He warned Matthew this morning that it must run in the family, and clearly he was right. It just seems the women are even more dangerous than the men. Matt confirmed it as well, complimenting how good Anna was right before she gave him a nap. You should have seen her Judes! She even whispered something in French before the big finish. She was incredible!"
"Oh my gosh! I never would have expected shy little Annie to be so daring!" Judy laughed in amazement.
"I can't argue that, but that's what boxing has done for her," Heather said, her motherly pride clear in her voice. "Between beating her brother, having him confess to her how much he was afraid she might be better than him, then knocking out her long time crush only for him to be so impressed with her that he begs her just for a date, I have never seen her so sure of herself. I know how she feels. I have been feeling it much myself since my first lesson with Billy."
"Wow..." Judy whispered with intrigue. After a few seconds of silence, she cleared her throat almost nervously. "Hey Sis, do you think Billy would be willing to teach Miranda...?"
Billy, who at some point slipped his hand in his pants as he relieved all these moments Heather was telling her sister, gulped when he heard his cousin's name. Miranda was much the same as Anna, a timid, bookish girl who didn't seem to have much confidence in herself. In fact, pretty much the only time Miranda and Anna had come out of their shells was when they were competing academically. Both had a habit of trying to show which was smarter, but their own shyness had prevented them from being too expressive, and it was mostly kept to occasional boasting about each others latest accomplishment. But the main thing that had made Billy pause was the idea of taking on his cousin like his mom and sister.
The truth is, Billy had always thought Miranda was attractive, even if she couldn't see it. Like Anna, his cousin had inherited her mother's beauty. While his sister had more curves, Miranda was a bit taller with a thin, yet still generous figure. Billy remembered seeing her in a bikini once at a family barbecue and had nearly choked when he saw what she often kept hidden under her conservative clothes. He still had a picture on his phone from that day that he had used to jerk his cock, much like he was doing now. He only sped up at the idea of Miranda using his face as a speed bag before letting him fall and putting her foot on his chest in victory. All while dressed in that same bikini that was now probably a size too small...
Billy's cock was hard as stone now, and he was trying not to moan from the lust he was feeling.
"Of course he would!" Heather exclaimed, thrilled at the idea of bringing in more opponents for her son to face. "That is an absolutely wonderful idea."
"Y-yes... Based on what you are telling me I really think it will raise her self-confidence," Judy said, though for some reason her voice sounded uncertain.
"Oh, I have no doubt of that," Heather agreed with a sly tone to her voice. "But that's not what you're really wondering, is it..?"
"Wh-what do you mean..?" Judy asked, clearly nervous.
"You want to know if he will train you," Heather said smugly, "because you want a chance to knock him out too..."
There was a long moment of silence before Judy responded with a single word.
"Yes..."
Billy had to shove his hand in his mouth and bite down hard to keep from shouting as his dick burst in his shorts. He could hear his mother laughing and continue talking, but nothing else mattered anymore. When the image of Aunt Judy, a woman with a body as incomprehensibly perfect as his mother's, entered his mind and he imagined being helpless on his knees before her, Billy had simply lost it. Billy pictured his goddess aunt with her gigantic tits hovering over him right before delivering the finishing blow as wave after wave of cum fired from his tireless dick. He barely paid attention to the cum that soaked his leg and made his underwear cling to his leg. It was unfortunately becoming a rather familiar sensation now. Instead he tried to calm his breathing and focus his mind on the task at hand.
Billy had a choice to make. He looked over his shoulder and saw the source of his nightmare, the dreaded gloves he had created. He still had a chance to grab them and run. If they disappeared, maybe, just maybe everything would go back to normal. But now he also had the chance to face his cousin and his aunt. He could make the images he'd dreamt up in these last few minutes a reality if he could just endure this humiliation a little bit longer. But if his mother's gloves vanished, that might not happen. Was he really willing to risk what remained of his reputation, just for a few more moments of pleasure...?
His mom could come out any moment. It was time to choose...
What does Billy decide?
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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