killing people while their blood is splattering around the town, making it red.
“you little fuck head, you should be dead, i’ll pull up in a coffin and paint the town red.” -zillakami
by Fat Mama Joe June 11, 2022
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To have violent intercourse with a woman while she is menstruating.
Dude 1: I'm about to have some super-hardcore sex with my girlfriend.

Dude 2: Isn't she on her period?

Dude 1: Yeah. I'm about to Paint The Town Red

Dude 2: That's gross.
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when a girl is on her period and she wanders the street with a skirt/dress and no underwear on dotting the streets with blood.
Nicole: Steve donkey punched me last night, I think I am going to blow off some steam and paint the town red. Lisa, can I borrow your white skirt?
by sharting sesame seed February 27, 2009
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Accidental menstruation on public property including buses, restaurants etc. for an extended amount of time.
I like, way spaced on tampons and had to paint the town red today.
by Heat* April 23, 2007
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