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

Sail boating by TeamCook January 21, 2019

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.

sail up to Ottawa by Back Door Buzz July 16, 2019

Sail Hypixel Guild 

a good guild with active members

Oi mate I jusy joined the Sail Hypixel Guild, it's got lots of active, friendly members and it has decently low requirements, aswell as a decently high level!

Sail Hypixel Guild by SailorStifi April 14, 2022

sail the ocean 

To finger/caress/play with a partner's body while receiving nothing back.

I heard that Tom was going to sail the ocean with Stacy.

sail the ocean by lb180 October 11, 2022

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.

Sail close to the wind by Arminkshipper July 25, 2024

sail the seven seas 

to pirate something, usually software or other electronic downloads. usually the pirating website is very sketchy and you will probably get a virus but it’s worth it sometimes.

i dont have the money for my college textbook so i sail the seven seas to get a pdf

sail the seven seas by pinkpillowprincess July 8, 2025

Set sail 

To experience peak sexual satisfaction

Only Senchou can make me set sail

Set sail by Overseassexyguy July 20, 2021