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

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

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

argh walk the plank you scallywag yo-ho let's go sail the seven seas

pirate

"argh walk the plank you scallywag yo-ho let's go sail the seven seas you varmint"

by mm 9 September 22, 2025

Sailing

sail·ing
/ˈsāliNG/
The fine art of getting wet and becoming ill while slowly going nowhere at great expense.

Sailing is my friend's hobby, but I can never figure out why he does it every weekend.

by TheValGal November 12, 2023

Sail

Slang for suicide, or a suicide attempt. Similar to the slang associated word, "off, offed, offing".

"Yeah did you hear? That guy sailed"

by Nomicaluran December 23, 2023

Bullish Mast & Sail

a bullish mast & sail, invented by Theodicy in 2021, is found by a identifying a massive green candled centered in between ascending bottoms and tops left to right

The bullish mast & sail on Google's stock ticker makes me hard AF rn

by Theodicy_sandman July 5, 2021