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1.
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
 
2.
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 01, 2010
 
3.
Someone who sits on top of a flag pole.
Look at that flagpole sitter!
by TimTam February 29, 2004