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

dead sailor

When you are having vaginal sex and it slips in the wrong hole

Last night John and I were doing it and I swear he tried to dead sailor me on purpose!

by Realest g around February 17, 2023

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 21, 2023

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

Full Sail

1. Extremely impressive or awe-inspiring.
2. Having a high level of commitment to something you are passionate about.

3. Giving one's absolute best, putting in the work and staying focused.

Synonym: balls out
Antonym: mid

We're going full sail on the marketing project with an increased budget and specialists.

Have you seen Jack's new gaming set up? It's full sail.

by Nora West September 22, 2023

hoisted sail

spread a sail or sails.

As the wind rose up, the crew hurriedly hoisted sail and started off over the wide sea.

by Arminkshipper January 29, 2026

nutty sailor

When you having sex with a women in a bath tub and cum in the water. Afterwards you blow the floating cum into her mouth.

Ted and Wanda were taking a bath the other night when he gave her a nutty sailor.

by Rub_a_dub_chub February 8, 2025