TWV: The Bet

“Bet you do!”

“I don’t. Honest.”

“C’mon. Every guy does. My brother still has a couple pairs of tighty whities and he’s in college!”

“Sorry, Jess. I haven’t worn them since I was like eight.” Jess rolled her eyes.

“You’re obviously lying or something.” She said dismissively.

“You’re the one that brought it up!”

“You’re the one that was snickering like a moron about Davey Conta wearing them in the locker room!” Jess smirked. “Bet you anything you had at least one pair of tighty whities upstairs.”

“I honestly don’t.” Why was she so fixated on this?

“Then you won’t be afraid to prove it. Right?” Jess got up off of the couch.

“Can’t I just drop my pants or whatever?”

“That won’t prove anything.” Jess said with a wicked grin. He sighed. She had her mind set on it now, so there was no way to dissuade her.

“Fine, let’s go. But when I prove it, you’re gonna owe me big.”

“What do you want?” She asked as they climbed the stairs.

“I’ll let you know after I prove to you I don’t have any tighty whities.” He scoffed at the very thought as he led her into his bedroom. “See?” He triumphantly yanked open a drawer full of a bunch of boxers and boxer briefs haphazardly shoved in there. He looked at her face, waiting to see the sweet look of defeat on her face. He did not know why, but she gave him a smirk.

“Seriously? You couldn’t just admit it?”

“Admit what?” He looked over to his drawer and his jaw dropped. He had just seen his boxers, but now? There was nothing but neatly stacked white briefs filling the entire drawer. “What the?”

“Real funny.” Jess said. “Do you stack them so nicely or does your mom?”

“I swear to god, those weren’t there a second ago!” Jess rolled her eyes.

“You really expect me to believe that?”

“Yeah, cuz it’s true.” Jess smirked.

“Alright, I believe you.” Sarcasm dripped from her voice. “Let’s go back downstairs.” She turned and gestured toward the door. “Ladies first.”

“Very funny.” He muttered, rolling his eyes. He pushed past her, but she suddenly swooped over and grabbed the back of his boxers.

“Wedgie!” He howled as she yanked up hard. “You’re even wearing them! At least they’re clean!”

“What?” His head turned faster than it ever had to see the white cotton in her hand. “What the hell?” Jess just smirked and gave another tug, cackling as he howled.

“Alright” she said, letting go of his underwear and snapping a photo of his stretched out pristine white briefs. “Fix your tighty whities and I’ll see you downstairs. Tighty whities boy.” She snapped another photo of his predicament before disappearing downstairs, leaving a very confused boy in her wake.