A word used to describe the massive length and girth of an individual's penis. This particular individual would be a native of Liberia.

A Liberian flagpole can measure anywhere from 9 inches to approximately 11 feet soft.
"Look at that guy's dick. I mean that thing is a Liberian Flagpole."
by BustMyCashew37.5 November 8, 2018
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Hand job given to another person under a table or desk.

Since flags are supposed to be hauled down during rain a flagpole under a protective cover would protect a flag from the rain. Since a flagpole could be an analogy for a penis a penis under a table/desk could be likened to a flagpole protected from the rain - 'rainy flagpole'.
Prudence totally gave me a rainy flagpole during the morning meeting.
by Bucko McCane March 29, 2009
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When a female is orally pleasuring a man and her gag reflex causes her to vomit on said penis.
"Oh man I got oatmeal flagpoled last night"
by Dipstick Master Juice October 8, 2008
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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 21, 2005
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Inserting one's member into different sauces and inserting into your partner's vagina, and then into her mouth so she can guess what the flavor is
I dipped my cock in BBQ sauce and gave my girlfriend a Musky Flagpole, she thought it was fish paste!
by Skibert April 15, 2009
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First you find your nerd. Then you grab their underwear, lift them, and take them to the flagpole. Once there tie the flagpole rope through the underwear leg holes and lift to the top. This is the best to make them suffer
So as a proud bully I have hung many a nerd by their underwear There are two stories though that are my favorite

The first was a nerd named Devon. You see Devon was a nerd that literally no one cares about. So one day of my senior year I decided to offer him a ride back to his home. He accepted and the second that he got in I shoved a used jock strap in his face. The smell knocked him out. I drove him over to this abandoned summer camp my parents bought for me to own and possibly renovate (never). I stripped him to his tighty whities and gave him the flagpole wedgie. He cried like a bitch and since that day, every day, I go back to feed him. His underwear is his bathroom so it is bad. Yes he’s still hanging. There’s still a missing persons case out for him. These extra strength briefs are the best! Hahahaha
The second was Willy. On my freshman year I wanted to prove I was cool so I took this nerdy senior and gave him a flagpole wedgie. Sadly his underwear was weak. He ripped and fell 20 feet down.. poor Willy..
by Bullybro March 11, 2018
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