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

Dirt sailing

When a man takes his erect penis and in a smooth "sailing" motion runs it along the butthole of a prone person.

The other day Kenny tied a little sail to his dick and went dirt sailing before throwing a piece of eight on her back!

by Habberstamp July 10, 2022

sails fine

Shit that rides smooth. Good shit. Smooth sailing.

Sails fine, man.

by Neverendbro December 15, 2010

Sets your sail

"Set your sail" is a way of say something excites someone.

Ex. Good looking men set my sail.
Ex. What ever sets your sail!

by Young and Fun July 05, 2018