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Rated: 18+ · Interactive · Fashion · #1928522
A bunch of stories that all result in a man dressing like a woman.
This choice: The Prom Bet  •  Go Back...
Chapter #6

The Prom Bet

    by: Vanilla Thunder Author IconMail Icon
Today was the day. You, Daniel O'Malley sat in your homeroom class in your high school. You were a senior, and it was the week before prom, so most students weren't interested in the grades. But you were, and so was your friend Jennifer. You and her were best friends since childhood, and you had a friendly rivalry over grades.

This time though, it was different. Since you'd be going to different colleges next fall, this was the final time you could compete, so you decided to make it an unforgettable bet. It started a few months before. You remembered the bet you made.

"Okay, so here's the rules. Whoever gets the higher grade gets to make the other one do whatever they want." Jennifer said.

"It's gotta be something good, too." you said. "Something the other would never want to do."

"Something embarrassing." Jennifer laughed.

"I've got it! If I get the higher grades at the end of the year, you have to wear a dress to prom!" you said.

"You wouldn't!" Jennifer said. She was a tomboy, and was never much for wearing anything that didn't have pants.

"That's my stakes. If I win, you're showing up to prom in a dress." you said.

"Fine!" Jennifer said. "If I win, you have to wear a dress to prom!"

"What? But I'm a guy! Pick something else!" you said.

"Oh, no. You said anything, and if you're gonna make me wear a dress, I can do the same to you." Jennifer said.

"Fine. You're on. Can't wait to see the dress you've picked out." you laughed.

After your memory of the bet ended, your teacher began to hand out the report cards. You got yours and opened it, seeing that you had gotten the highest grade possible. There was no way that Jennifer could have gotten a higher grade. You looked over at Jennifer, who was grinning. You snickered, since whatever she got, it wasn't higher than your's. Class ended and you walked up to Jennifer.

"Looks like someone is going dress shopping this weekend." you both said in unison.

"Huh?" you both said in unison again. "I got the higher grade."

You looked at her report card, she had the same grade as you. She was similarly dumbfounded.

You both walked up to the teacher and explained the predicament.

"So, you had a bet to see who'd get the higher grade, and you both got the exact same grade?" your teacher asked.

"Yeah." you said.

"I guess the only way to fulfill the bet, would be for both of you to wear dresses to prom." your teacher said.

"If you do it, I'll do it." Jennifer said.

"..." what do you say?

You have the following choices:

1. I'll do it.

*Noteb*
2. No way!

*Noteb* indicates the next chapter needs to be written.
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