All Sail!

it's a word for Pirates

Pirate: All Sail!
Someone: Aye, Aye, Captin!

by All Sail! June 5, 2020

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 9, 2022

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 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.

by lb180 October 11, 2022

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!

by SailorStifi April 14, 2022

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

by pinkpillowprincess July 8, 2025

Hoisting The Sail

When you super glue one ball to each leg and you proceed to run a marathon.

“Man, that marathon was such a pain I don’t think I trained enough!”
“Tell me about it! I was hoisting the sail the entire time.”
“Not surprised, you’re a dirty hoister.”

by SwagRK July 13, 2025