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

The Ship Had Sailed Before Its Occupants Made It To The Harbor

Also "The Ship Had Sailed Before Its Occupants Made It To The Port".

An idiom meaning the ship between characters was confirmed canon before people started shipping them.

Person 1: Doom Guy and Isabelle have already been confirmed canon by Nintendo.
Person 2: The Ship Had Sailed Before Its Occupants Made It To The Harbor

by Shugunou October 23, 2023

sail up to Ottawa

That's where you put it in her twat then finish in her mouth

Sure, I know your sister! We frequently sail up to Ottawa together.

by Back Door Buzz July 16, 2019

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

Tag Sailing

Tag Sailing is like a pub crawl but with tag sales. One right after another. Usually on a weekend.

The town-wide tag sale is today. Who wants to go Tag Sailing?

by Randwulf0969 June 24, 2023

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