Flagpole

n. An erect penis.

Come on dear! climb on top the flagpole tonight!

by 70's guy March 29, 2006

flagpoling

Leaving the country solely for the purpose of re-entering so that you can activate a new immigration document.

ROB: I got approved for a new work permit for my specialized burger flipping job at McDonalds. I'm flagpoling tomorrow at the Niagara Falls border crossing.
JOE: What a joke. I'll show you where you can stick your flagpole.

by Werdly Smith November 2, 2011

Flagpole

An oral sex position, wherein the fellator holds their body horizontally (as a flag relative to a flagpole) while performing fellatio.

"I hear Rebbecca totally gave that RA a flagpole! That sh*t is BANANAS!"

by OctaveO October 9, 2009

the flagpole

Taking a flagpole and ripping the flag off and shoving it in the females mouth while the male shoves the flagpole in the females dilated vagina while the male also continues to shove his penis in the females anus while singing the national anthem

I really enjoyed the flagpole with G-MA last night

by Nigga Stacey January 3, 2014

Flagpole

Swiping your finger(s)in an upward motion on/in the crack of someones ass, not during a sexual encounter(usually).

If you flagpole me, I will punch you in the nose.

by Crystal2007 January 18, 2009

flagpoling

having anal intercourse with a female looking like you are hanging her from your "flagpole"

Me: So how did it go with that girl you hooked up with man?
Peifer: Dude i was totally flagpoling her man
Me: well you might as well be gay right, i mean an asshole is an asshole right?

by Matt aka Stuffin McMuffin May 31, 2007

Flagpole Wedgie

A wedgie where the victim is hoisted up to the top of a flagpole by their underwear. This is the best form of wedgie if you want the victim to suffer the longest, and if done in the summer, can last for days.

I gave this nerd called Jake a flagpole wedgie during summer vacation. I stripped him to his briefs and strung him up on the flagpole, giving him water and canned beans three times a day. I managed to keep this nerd up there for six days, and by the time a construction worker got him down, he was a mess (his underwear was his bathroom) and he couldn't walk cause of the pain in his butt. I still wedgie Jake to this day.

by Rappunk799 June 16, 2014