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"sail" is a homosexual term that means "wander from gay bar to gay bar, not leaving until you've let someone 'drop anchor' in your butthole".
J. Dyer has been sailing between Hulas, Angles and The Man Hole all night but hasn't found any takers
by CaptainAloha July 12, 2018
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To all you dumb fucks who think it is sexual, it is a piece of material extended on a mast to catch the wind and propel a sail boat. Or as a verb it means to go sailing.
"Do you sail?"
"Yeah, I went sailing last weekend and came back soaked and tired."

"That dude has a giant sail on his sailboat!"
"Yeah, I bet that boat does great in regattas!"
by Ija Renrut December 09, 2013
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The little piece of skin that connects the penis to the balls.
she lighty tugged on his sail.
by Rockmjd23 October 04, 2003
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the act of when a guy is skinny dipping and has boner then lays on his back so that his dick is out of the water and his dick acts like a sail of a ship
guy1: Dude i was skinny dipping yesterday and i saw cody sailing away like a pro
guy2: yeah thats the way to sail!
by codythegreek May 30, 2011
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7
When the canon ships your one true pairing (OPT).
Ex 1: "Yes! Finally! They got together! SAIL!" *wheezes*
Ex 2: "They're so cute together! I hope they sail."
by The Quiz-Trivian-Naire December 10, 2017
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