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

clam sailing

When a woman with a skirt and no underwear (or naked) stands over a vent that's blowing air.

Marilyn Monroe was holding her skirt down because she was clam sailing to dry off.

by DoomEngin33r March 31, 2017

Sail Boating

Swimming on your back while having a massive erection.

"Dude, did you see Jenny in her new bikini at the pool?"
"Yeah man, I saw her while I was practicing my backstrokes. She had me Sail Boating."

by Sarpa May 26, 2016

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

by TeamCook January 21, 2019

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 08, 2023

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.

by Back Door Buzz July 16, 2019