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  1. Go dress shopping as a boy
  2. I'll do it.
  3. The Prom Bet
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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: Go dress shopping as a boy  •  Go Back...
Chapter #8

Go dress shopping as a boy

    by: Hei Author IconMail Icon
"The bet was to wear a dress to the prom. Not before." You said.

Jennifer nodded. "But wouldn't it be embarrassing if you go in as a guy buying female clothes?" She asked.

"People will just think of us a couple. And that we are buying a dress for you." You said. Jennifer thought about it and knew that you were right.

"Still we need to know your measurements for the dress." Jennifer said.

"We can get my measurements here and just ask them to give us the size." You retaliated,

Jennifer gave a sigh. "Alright. If that's what you want." She said as she got out of her room and came back with a measuring tape.

After the measurements were done the two of you had left to go do some shopping. You had asked if the two of you could go out of town to avoid meeting familiar faces.

"This is what I meant. You should have just gone shopping dressed as a girl." Jennifer said.

"And then what? Go home dressed as a girl as well!" You replied.

What does Jennifer say?
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