Square of Despair

While in prison, you are unwillingly taking it up the ass, having one shoved in your mouth and giving hand jobs to guys on either side of you.

Hey man, you hear about Lil' Pete getting the Square of Despair in the showers?

by Darth Zilla the Bob October 16, 2019

square of despair

Similar to the "circle of trust," this is to describe the state of feeling despair-usually when you break-up with someone.

Mary, I am in the square of despair after I broke-up with John.

by im cooler than almost everyone December 12, 2008