Sex sails

A sexual play on the saying ‘wind in my sails’.

Ernie paused to turn up the television volume, which really took the wind out of my sex sails.

by Snake Lovin’ Gurl January 19, 2018

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

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

Wet Sail

A nautical term for when sailors boat sails would become wet and droop and become useless.

Sometimes used as an insult meaning, useless and/or dumb

Guy 1: That chick is such a wet sail.

Guy 2: Yeah she's pretty stupid.

by plaauqe lele October 10, 2013

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

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