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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?
Used when referring to a golf cart that has been taken off of (specifically) private property and driven down public roads illegally.
1. I saw Buddy sailing the fucking cart down the street like a champion who gave zero fucks.
2. Bill asked “how will we be getting there?” And Michael answered “fucking sailing the cart boiii !!!”
“I was sailing my side and my main hoe called my phone, I watched the phone ring”
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!
"Set your sail" is a way of say something excites someone.
Ex. Good looking men set my sail.
Ex. What ever sets your sail!
A woman that gives a blowjob to everyone in the room all in a line.
Bitch, you totaly cum sailed that party the other night!