Another way of saying going commando (for a male). Willy means dick. Your dick and balls are freely hanging when you go commando.
My favorite way to jog or do jumping jacks is while I'm Free Willy.
by M_Dubz152 June 9, 2023
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When your smoking a bong and start to take a hit but end up coughing down into the chamber causing water to shoot out the stem, like a whale shooting water out of its blowhole
Douglas tried taking a huge bong rip but just ended up free willying
by SaltySB October 11, 2011
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When recieving head the male pulls out just as he is about to blow his magic load and sticks his cock in her ear.
So Tess was being a real butt squirell so Matt gave her a Free Willy and now she can't hear anymore. No whales were harmed in the making of this sexual experience.
by Stefan Beaumont May 10, 2008
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You shoot a load in a fat chick's mouth and hold it shut. You the punch her in the stomach until the load shoots out of her nose.
Dude, this chick was all up on my junk like a fat chick eating a donut. So I decided to free willy her and glaze that cock for her.
by DeezzzzzzNuts January 8, 2015
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A penis swimming through the sea.

This is because in England, Willy means penis.
This is amusing. XD
Sarah: Yeah, well Andy Sixx is just...a penis.
Tk: Hahaha, just a penis with no body. XD Like free willy.

Sarah: I drew Free Willy on my math homework.
Hannah: You're stupid...
by hai_bai November 1, 2010
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When a smoker blows smoke rings and a guy ejaculates through the rings onto the first person's face.
Hey, Jordan, last night this pot-headed chick let me free willy her face.

Wait.. that's sick she smokes?
by Toothpaste18756 November 28, 2010
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