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flag pole 

An anal retentive person; A person who has a pole up their ass.
My professor won't let you into the class, five minutes after class has started. He is such a flag pole.
flag pole by Brown Eyed Girl June 4, 2005

Flag Pole 

Skinny dick, big foreskin. Typically unsightly. Looks like the skin could be painted and used as a flag. Skin gets so worn that it's hard to get laid. Usually can't get a date so they gotta masturbate. Some times there is lube, some times there ain't. Before you know it your foreskin inflates.
Example 1: "I was going to go down on the guy, but he wiped out a real Flag Pole. It was long but the skin was so floppy I almost gagged on it. I'd be surprised if he even felt it at all."

Example 2: "Today I showed my patriotism online. Painted my dick and foreskin like a Flag Pole and snapped a picture in the wind. They got more of a laugh out of it than anything."
Flag Pole by Half Mast May 27, 2021

Flag Pole 

Your partner grips the bed headboard whilst you lift her legs up in the air wheelbarrow style and go to town on that shi until she screams "fly my like a flagpole!"
When she grabbed the bed headboard i just had to hit the Flag Pole on her
Flag Pole by NigNut97 May 30, 2025

sanding the flag pole

playing with oneself/ masterbating
JR spent the day "Sanding The Flag Pole"
sanding the flag pole by Schizzna October 22, 2008

Akward Flag Pole 

It's when one person puts their fisted hands on top of eachother to make the pole. Another person then puts their hand on top of "the pole" and makes a flag and waves it. It's used in akward or just randomly to get some laughs. Also done when everyone starts doing different kind of akward things, like the akward turtle, blowjob, moose, etc.
After Johhny made his comment we all started doing different akward things, me and Jamie did the akward flag pole to the amusement of everyone.
Akward Flag Pole by Caboose1 December 12, 2009

lickin the flag pole 

Licking the Flag Pole places the partners on their sides with the receiving partner placing their lower thigh under the head of their performing partner, while the upper leg points to the sky - hence Flag Pole. This position really opens up the groin area and is a big hit for the additional hand stimulation that can be provided.