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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: Teenage  •  Go Back...
Chapter #8

Teenage

    by: Vanilla Thunder Author IconMail Icon
You were competitive, you'll admit that. And your best friend was just as competitive, to the extent that you were always making crazy bets with him. By your senior year of high school, it was a common occurrence to be embroiled in one bet or the other. Off the top of your head, you could remember one where you had to walk around school wearing a sandwich board that said something embarrassing on it. But you didn't always lose, sometimes he would, and you'd come up with an equally embarrassing punishment for him. Such was the case on this day...

You were sitting in your bedroom playing video games, when your friend took a look at the high score screen, and said that he could top it in one try.

"No way, you can beat my high score!" you exclaimed. "It took me weeks of practice to get it that high!"

"You wanna bet, Mark?" your friend, Jimmy, responded.

"Yes I do." you said.

"The usual bet?" he asked.

"Winner picks loser's punishment." you replied.

"Let's do this." he said.

Jimmy started playing the game, and while at first, you weren't nervous... he was really good. You started to sweat. The punishments were always so embarrassing... and it's a lot easier to be confident when you're the sure winner... After a while, your face dropped when Jimmy beat your score by 200 points.

Jimmy put the controller down and laughed.

"Well, looks like I win." he said.

You were ready to take the punishment like a man, when a thought occurred to you so fast, that you spoke without thinking.

"Wait." you said. "I bet I can top that in one try."

"No you can't!" Jimmy rebuked.

"If I can, double or nothing." you replied.

Jimmy smiled again.

"Sure." he said.

You picked up the controller and started to play. You put up a good game, but you came up short, only matching your previous high score. You dropped the controller in frustration and sighed.

"Double it is." Jimmy laughed.

"What's the punishment?" you asked, dreading hearing the answer.

"Well... I was just going to make you wear a dress to school for a week... but if we're doing double..." Jimmy started. "I want you to..."

You have the following choices:

*Noteb*
1. Attend the school dance dressed as a girl

*Noteb*
2. Go to a convention dressed as a girl

*Noteb*
3. Something else

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