Flagpole Sitter

When a man/woman shoves his/her arm up their partner's asshole.

"My girl said she wanted to try something new to spice up our relationship, so I gave her the old flagpole sitter.

by coochieman69 May 2, 2010

flagpole sitter

When a man or woman intentionally or unintentially sits on top of a penis. Also, when a Davo sits on top of a Pumster.

Wow, he's got that flagpole all the way up bobby evans' anus! That old skool nigga's one flagpole sitter!

by HugeBreasticle February 20, 2005

flagpole sitter

Someone who sits on top of a flag pole.

Look at that flagpole sitter!

by TimTam February 29, 2004