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
Someone who sits on top of a flag pole.
Look at that flagpole sitter!
by TimTam February 29, 2004