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"Set your sail" is a way of say something excites someone.
Ex. Good looking men set my sail.
Ex. What ever sets your sail!
A woman that gives a blowjob to everyone in the room all in a line.
Bitch, you totaly cum sailed that party the other night!
To spend long periods of time on one's front porch. Usually involves music, conversation and some form of inebriates. May also involve food, especially food produced from a grill.
I'm just planning to sail the porch tonight, you can come hang, too.
When a woman with a skirt and no underwear (or naked) stands over a vent that's blowing air.
Marilyn Monroe was holding her skirt down because she was clam sailing to dry off.
Chantal: I thought gentlemen never sail to windward.
Rodriguez: I'm no gentleman, baby.
Swimming on your back while having a massive erection.
"Dude, did you see Jenny in her new bikini at the pool?"
"Yeah man, I saw her while I was practicing my backstrokes. She had me Sail Boating."