Painting the flagpole

To jerk (masturbate) of

Im going to be painting the flagpole at two in the morning

by Gay man dictionary July 13, 2021

Flog the flagpole

To masturbate

Excuse me while I go to the bathroom and flog the flagpole

by StopSpacism November 27, 2022

flagpoleing

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

flagpoling

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 20, 2011

flag pole

When a person passes out drunk and you stick a broom stick in their ass. It sticks up like a flag pole. Adding a real flag is optional.

I passed out lastnight and the bastards gave me a flag pole!

by bizzach April 11, 2005

flagpoling

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

sanding the flag pole

playing with oneself/ masterbating

JR spent the day "Sanding The Flag Pole"

by Schizzna October 22, 2008