Definitions by Jon Jacob Jingleheimer Schmidt

Paint The Town Red 

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.

Paint The Town Red by Jon Jacob Jingleheimer Schmidt October 11, 2010