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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 15, 2022


GARAGE SAILING

The act of going from one garage sale to the next, to the next, to the next, and so on and so forth. Taking a day or a weekend or a few hours to desperately search for other people’s junk.

Me and Fred are going garage sailing this weekend you should join us, we’re too broke to go to the store....

by Descriptiongiver101 August 16, 2019


sails and cervix

What a horny dude would hope dat da hot female skippers of a schooner-tours company would offer.

When booking an outing with a seaside shop offering “sails and cervix” package-tours, one should make sure to ask if their standard price includes having your gorgeous guide spread her legs for you, or if said delightful “extra” actually COSTS “extra”!

by QuacksO October 8, 2023


Sailing

To have sex with somebody

“I was sailing my side and my main hoe called my phone, I watched the phone ring”

by Basharrr January 12, 2023


Sailing the cart

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 !!!”

by harry pot May 15, 2018


sails and service

What a marine-supply store offers.

I always shop locally for all my boating needs; they have exceptional sails and service.

by QuacksO March 22, 2023


Floor Sailing

Floor Sailing is the next submission to the Olympic Games Committee defined by the distance a person travels while tripping or slipping on a smooth, slick or slippery surface!

Dude if you had only practiced a little more you could have gotten a Gold Medal in “Floor Sailing“ for that record slide in class!!

by OneVisionVideo November 28, 2020