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Rated: 18+ · Interactive · Fashion · #1928522

A bunch of stories that all result in a man dressing like a woman.

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Chapter #4

summer break

    by: Unknown
ChatGPT said:
Got it — here's a snappier, more embarrassing version with a clearer setup: Andrew isn’t transferring mid-year, but because he's coming from a different state, there are certain requirements his new school says he has to catch up on over summer. The tone leans more into awkwardness, and the branching sets him up for future humiliation potential.

[SCENE CONTINUES]

You toss the last of the clothes onto the bed and just… stare.

Tight jeans with heart-shaped stitching on the back pockets. A baby blue crop hoodie with “Take It Easy 💖” across the front. Tank tops with spaghetti straps. A couple of soft pastel bralettes that clearly weren’t meant for you, but your mom said “they might fit like undershirts.”

You knew things would be a little different after moving, but you didn’t expect to be stuck in Melissa’s maternity castoffs and Kate’s “freshman girl chic” phase from college.

At least it’s summer break. You won’t have to face anyone for a while. Right?

Heather peeks into the room.
“You find the pink jeggings yet?”
She grins. “Mom said those were stretchy. Perfect for your little hips.”

You freeze.
“I'm not wearing jeggings.”

Heather shrugs. “Okay. Then I guess you’re wearing nothing when we go to Aunt Emily’s barbecue.”

You flop back onto your bed and groan. It’s going to be a long summer.

Your phone buzzes.

📩 WEST PINES HIGH SCHOOL – NOTICE

Hello Andrew,
Due to curriculum differences between states, you’ve been assigned a few mandatory summer catch-up tasks.

You have the following choices:

1. swimming lessons

*Pen*
2. pe tests.

*Pen*
3. something else

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