There was a time where Two-Bit wore his mother's dresses just for laughs. He would enter the Curtis home in one of his mother's dresses and imitate a stereotypical woman. He has already ripped a couple of dresses in the process. Yes, he has done this several times.
Poor Ms. Mathews
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The Outsiders Headcanons & Facts
Fanfiction- Things people tend to forget about The Outsiders - Headcanons - Movie Facts If I missed any facts, PLEASE tell me