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A sexual act performed by having a woman lay on her stomach and inserting your big toe into her ass, using it as leverage to perform a kickflip
Man: I just landed my first Jamaican Skateboard with your wife.
by BobbySteve December 26, 2025
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when u got crossed up on the court and broke you're ankle but don't want anyone to know u got crossed up so you tell people u know that u fell off a skateboard
Friend: dam bro how u break your ankle?

Brian: i Fell off a skateboard

Friend: dam thats crazy
by Dawson's gay January 6, 2022
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Shoot the skateboard

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When you rob a bank and you run in with a Ar-15 and proceed to miss all your shots on the person on the skateboard (better used when their name is Jerome.)
You heard that one guy that just recently pulled a "shoot the skateboard
by dopod April 13, 2025
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Skateboarding

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Stereo types aside, it's just a thing that some people like doing. Frowned upon by cops, business owners, and midle aged rich stuck up Bitchy women. You get kicked out of anywhere you can think off by just skating flatground.
HEY! THERES NO SKATEBOARDING HERE. YOUR DAMAGING THAT LEDGE!!!

But, we're skating flatground, though.

THATS IT, I'M CALLING THE POLICE!
by 75283skate March 24, 2011
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The expression is NOT a reference to people critical of the subculture, nor was it EVER used as an excuse for any real crimes committed by people on skateboards. It was responding to the growing numbers of towns in the 90s ban skateboarding in public, despite the number of people who rode bikes, roller blades, and, oh yeah, drove CARS just as unsafely as skaters skateboard.
Skateboarding is not a crime, so take the stick out of your ass.
by Stillravenmad November 4, 2008
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