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

gentlemen of culture

this is how dudes commenting on thirst trap (and often ai-generated) youtube/facebook/tiktok videos salute and acknowledge each other's motives and aspirations

"Gentlemen of culture, we meet again>"

by nouiknouik May 3, 2025

gentlemen sausage

A man's dick

I want you to taste my gentlemen sausage.

by Shanuatwork October 17, 2018

MAMTEB GENTLEMEN

A member or members of the group MAMTEB, who most generally have the following traits: wearing top hats and/or bow ties, being part marmat, and being extremely well-hung.

Mrs. Percy: "Oh, dear. I haven't had my clitoris stimulated or my hedges pruned in the shapes of funny little forest creatures lately. What shall I do?"

Brad Pitt: "Call a Mamteb Gentleman. They are all hotter than I am."

Mrs. Percy. "Okay. You're right. Mamteb Gentlemen always satisfy every desire."

by Steven Gardner October 24, 2007

Gentlemen’s Woman

A lady who gets all the guys. The female version of a ladie’s man.

“I’ve never seen any gentlemen’s women portrayed in media ever. I thought I’d see some?” -me

“Erica the gentlemen’s woman gets so much dick she’s living the life” -Stacy

by Superjuliam November 22, 2022

A Gentlemen's Race

A race wear two (or more) men start ejaculating at the same time and whoever finishes first, wins the race.

"Hey man I heard they had a Gentlemen's race in the men's bathroom right now."

by JJohn7 August 9, 2017

Gentlemen's Cocaine

A combination of multiple prescription medications, powderized and meant to be snorted to induce a sensation of euphoria, to a level unobtainable by any other drug.

"Last week I did Gentlemen's Cocaine, i didn't really get high, but everything has seemed better since then."

by Ananaa January 22, 2012