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Challenge Accepted: When Sibling Rivalry Turns Intimately Hilarious

Chapter One: The Bet

Jane and Joe were comfortably sprawled out on the couch in their shared apartment, nursing glasses of wine as they discussed their latest romantic escapades. Joe, the younger of the two by two years, was lamenting about the fact that none of his ex-girlfriends had ever gone all the way with him.

"Come on, Joey, it's not like you're small or anything," Jane joked, patting him on the shoulder.

Joe raised an eyebrow at his sister. "Oh, really? You think so?"

Jane shrugged. "Well, I've never seen it, but I assume it's average."

Joe smirked. "You know what they say about assumptions, Janey."

Jane rolled her eyes. "Yeah, yeah. But seriously, if you're so concerned about it, why don't you find someone who's willing to, you know, test the theory?"

Joe's smirk grew wider. "And why don't you find someone for me?"

Jane laughed. "Nice try, but I'm not setting you up with any of my friends. Besides, I don't think any of them would be willing to take one for the team, so to speak."

Joe's smirk turned into a full-blown grin. "What if I told you that I had a willing participant right here?"

Jane raised an eyebrow. "Who?"

Joe gestured to himself. "Me."

Jane blinked. "You?"

Joe nodded. "Yep. And I'm willing to put my money where my mouth is, so to speak."

Jane's eyes narrowed. "What are you suggesting?"

Joe shrugged. "I'm suggesting a bet. If you can prove that I'm small, then I'll buy you dinner at your favorite restaurant. But if you can't, then you have to buy me dinner at my favorite restaurant."

Jane's eyes widened. "Are you serious?"

Joe nodded. "Dead serious. So, what do you say? Are you up for the challenge?"

Jane hesitated for a moment, then shrugged. "Sure, why not? I've got nothing to lose."

Joe stood up from the couch, stripping off his shirt, pants, and boxers in one swift motion. Jane couldn't help but do a double-take at his size.

"Holy shit," she muttered under her breath.

Joe raised an eyebrow. "What was that?"

Jane shook her head. "Nothing. I just didn't realize you were so...well-endowed."

Joe smirked. "See, that's where you're wrong. I'm not just well-endowed, I'm above average."

Jane rolled her eyes. "Okay, okay. I get it. But just to be sure, I think I should, you know, test the theory."

Joe nodded. "Be my guest."

Jane stood up from the couch, stripping down to her bra and panties. She was surprised at her own boldness, but she wasn't about to back down now.

Joe sat back down on the couch, and Jane straddled him in the missionary position, guiding him inside of her. She was surprised by how deep it felt, gasping as he filled her up.

"Holy shit," she muttered again.

Joe smirked. "Told you."

Jane picked up the pace, causing Joe to groan in pleasure.

"Oh, fuck," he muttered.

Jane jokingly told him not to cum inside of her, but Joe continued to thrust faster and deeper.

"I'm going to cum inside of you," he warned her.

Jane jokingly replied that he could, surprising herself with her own forwardness.

Joe started to cum inside of her, and Jane felt him still hard inside of her. She was surprised by how much she was enjoying it, but she didn't want to admit it out loud.

Joe rolled them over, with him now on top, thrusting faster and deeper. Jane wrapped her legs around his waist, moaning as he hit just the right spot.

"Oh, fuck, Joe," she moaned.

Joe grinned, picking up the pace even more.

"You like that, don't you?" he asked.

Jane nodded, biting her lip.

"Say it," Joe demanded.

Jane hesitated for a moment, then sighed. "I like it."

Joe grinned, continuing to thrust deeper and harder.

"Cum for me, Jane," he commanded.

Jane didn't need any more encouragement. She came hard, moaning as Joe continued to thrust inside of her.

Joe came soon after, collapsing onto the couch next to Jane.

"I think it's safe to say that I won the bet," he said, smirking.

Jane rolled her eyes, but she couldn't help but smile.

"Fine, you win," she conceded. "But next time, I'm picking the restaurant."

Joe grinned. "Deal."

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