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

Sailing the cart

Used when referring to a golf cart that has been taken off of (specifically) private property and driven down public roads illegally.

1. I saw Buddy sailing the fucking cart down the street like a champion who gave zero fucks.

2. Bill asked “how will we be getting there?” And Michael answered “fucking sailing the cart boiii !!!”

by harry pot May 15, 2018

Sailing

sail·ing
/ˈsāliNG/
The fine art of getting wet and becoming ill while slowly going nowhere at great expense.

Sailing is my friend's hobby, but I can never figure out why he does it every weekend.

by TheValGal November 12, 2023

Sailing

To have sex with somebody

“I was sailing my side and my main hoe called my phone, I watched the phone ring”

by Basharrr January 12, 2023

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

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

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