A Sail

Term referring to when two straight guys rent a sail boat to engage in homosexual sex acts. Originating from the DMV area, particularly where sailboat rentals are available.

Could I tempt anyone with a sail? - a closeted homosexual

by DMV317 February 22, 2023

Sail close to the wind

verge on indecency, dishonesty, or disaster

Here's a sentence using "sail close to the wind":

The politician's campaign ads sailed close to the wind with their negative attacks on the opponent.

by Arminkshipper July 25, 2024

clam sailing

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.

by DoomEngin33r March 31, 2017

Mud Sailing

When you pee and take a shit at the same time. Most notably when you have food poisoning or had a beefy 5 layer burrito from Taco Bell.

Dude how's your stomach? Bro I been mud sailing all day from that burrito.

by Jermeiser February 03, 2016

Sail Boating

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."

by Sarpa May 26, 2016

Sail boating

The act of farting against the scrotum during Anal sex, turning it into a spinnaker sail.

After a delicious taco Tuesday meal, she took me sail boating

by TeamCook January 21, 2019

gentlemen never sail to windward

"nice-guys don't go for anal"

Chantal: I thought gentlemen never sail to windward.
Rodriguez: I'm no gentleman, baby.

by Carl Figleaf August 15, 2022