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

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

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

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

Mud Sailing

When you pee and take a shit at the same time. Most notably when you have food poisoning or had a beefy 5 layer burrito from Taco Bell.

Dude how's your stomach? Bro I been mud sailing all day from that burrito.

by Jermeiser October 6, 2016

Sailed the bay

Having used the website "Pirate bay"

Dad what are torrents? Ah, yes I sailed the bay many times in my youth. You Spotify kids would never understand.

by Wolvesofthenight March 30, 2025