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n. An erect penis.
Come on dear! climb on top the flagpole tonight!
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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.
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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!"
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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
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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.
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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?
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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.
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