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Chapter 4 by Throne65
How does the confession go?
Better than she could have dreamed
Jenny swore under her breath as she knocked on Jason's door. The night was warm and there were no cars on the road, but she still didn't want this to last any longer than it needed to. She planned to just tell Jason what happened, ask him out, and then go back to her house. If she was lucky, maybe Jason could give her a coat.
The door swung open as her favorite neighbor came into view. Jason was dressed in his own set of black pajamas, causing Jenny to worry she had woken him up. His blue eyes widened and his eyes darted up and down her bare body. Jenny hadn't bothered to cover herself; may as well go all the way with this dare, right?
"Uh, Jenny?" Jason asked. "Are you okay?"
"Oh yeah, I'm fine!" Jenny said, trying not to let her voice crack. "So, my friends and I were playing truth or dare and I was dared to tell you a secret about me."
Jason blinked once, finally processing what he was seeing. "Okay, I'm listening."
"Sooo, I was dared to admit to you that I've had this...crush on you for, I dunno, since we first met?" Jenny let out a nervous giggle, breaking her façade.
Jason's eyes opened ever wider. "R-Really? That long? Why didn't you say anything before? And why did you decide to do it naked?"
"First, the dare was just to tell you. My friends stripped me while I was outside and locked me out," Jenny explained. "And second, I really didn't know how to say it. I was kinda scared."
"You? Scared?"
"Yeah. I mean, I'm the girl who plays pranks on everybody and parties all night long and acts like everything's a joke. Since I turned 18, I've been doing riskier stuff, like streaking all over the neighborhood at 4 in the morning."
"That was you?" Jason asked. "I took my dog out that night, but I couldn't see you."
Jenny blushed with shame for the first time in her life. "Yeah, that was me. Come on, be honest, would a guy like you really want to go out with a girl like that?"
Jason eyed her up and down one last time. "Wait here."
The door closed and Jenny found herself sweating. This had been a horrible idea from the start. She realized she should have just found a way to sneak back into the house. Now she worried that Jason was calling the cops and would never talk to her again.
The door opened to reveal Jason had taken off his pajamas, leaving him just as buck naked as Jenny. "Does this make you feel any less embarrassed?"
Jenny found her eyes locked on his obvious erection and acquired a new first: a loss of words. "Uh...huh...gah…!"
What will the two do now?
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That lucky bastard/bitch!
Winning against the odds
The worst thing to have happen to someone is to lose their clothes in public or be into a humiliating situation. But for these poor losers, it causes them to have the best day of their lives. Maybe they win the lottery or get a promotion. But usually, the unthinkable happens: their crush or even a hot stranger can't get enough of them.
Updated on May 10, 2026
by Cyclops
Created on Jul 12, 2020
by Throne65
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