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.
Dude 2: Isn't she on her period?
Dude 1: Yeah. I'm about to Paint The Town Red
Dude 2: That's gross.
by Jon Jacob Jingleheimer Schmidt October 11, 2010

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

Accidental menstruation on public property including buses, restaurants etc. for an extended amount of time.
by Heat* April 30, 2007

Used to describe Manchester United.
by Kopthis October 3, 2019

I went to visit my nan in the old peoples home yesterday and she'd written her name on the wall in crazy people paint
by Dan the Bastard June 15, 2011

A sexual act in which a female is riding ones face in a sitting position until dripping sweat & pouring cum, then keeps riding.
Last night I let Sandy give me a Pussy Paint Job & i almost drowned from my mouth full of so much cum & piss.
by Back Pack Jack April 28, 2020

by Urbancowboy201 June 6, 2017
