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."
Your partner grips the bed headboard whilst you lift her legs up in the airwheelbarrow style and go to town on that shi until she screams "fly my like a flagpole!"
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.
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.