Allowing your boner to stand straight up, making it visible to all who are around.
Girl 1: "I think he's into you"
Girl 2: "Why?"
Girl 1: "Because he was flagpoling during your entire conversation."
by Jerry C. August 16, 2011
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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.
by Werdly Smith November 2, 2011
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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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Flagpoleing a sex position where the woman is on your d*ck or flagpole and she is the flag and she waves like flag.
Bill: good night?
John: yeah she was great.
Bill: you bang her?
John: we were flagpoleing
by hercumungous August 1, 2014
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The classic place for two opponents to meet for a fight.
1. "Meet me at the flagpole, 3 o'clock. We'll work out our difficulties."

2. "Excuse me, I have an appointment at the flagpole."
by Berzerkley April 21, 2008
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typically before a blowjob; when a girl is kneeling in front of a guy she’s about to dome, and he smacks his dick both ways across her face, back and forth, by twisting his hips side to side.
guy 1: bro, she let me flagpole and then i facefucked her so hard.

guy 2: dude, that’s so sick. i wish my girl would let me do that.
by trevdaddy11 September 7, 2019
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Come on dear! climb on top the flagpole tonight!
by 70's guy March 29, 2006
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