the gentleman's tip

The sex act where a man, upon receiving a woman's permission, inserts the index finger (no further than the middle knuckle) into the woman's anus during vaginal intercourse, and gently slides this portion of the index finger back and forth.

We find ourselves in the midst of a conversation between Jane and her friend Sarah that has stumbled upon the topic of anal sex, let's observe.
Jane: James has been asking for it forever, I don't know Sarah, like, I think he could be the one. What should I do?
Sarah: just have him start slow, with "the gentleman's tip" and work your way up from there

by JuiceBox89 January 28, 2015

gentlemans tip

when someone fucks in their friends bed and leaves the used condom in their pillowcase.

After I piped that thot I left a little gentlemans tip in his room.

by Monty Money December 15, 2020

Gentleman's Gang

Term used in polite conversation amongst African-Americans to describe a strip club and/or orgy.

"Oh! Hello there Tyrone! You missed my Gentleman's Gang meeting the other night!"

"I was having my own Gentlemen's Gang meeting with my neighbors, DeShawn and Ebony."

by ShaniceJohnsonMohawnson March 27, 2012

gentleman pilled

gentleman pilled, when you leave a large creatin for the cleaning staff, into finance X, and sexing hot babes!!! gentleman pilled. just shit on the bathroom floors and act like a boss.

"i left a large creatin n tartar for the cleaning staff, im so gentleman pilled"

by FrickerMan23 October 13, 2020

A gentleman's scratch

"A gentleman's scratch" is when you have an itchy bumhole and you fart at just the right capacity to simultaneously release gas and itch your bumhole within the same manoeuvre

"i preformed A gentleman's scratch to itch my bumhole in bed last night"

by ScottyFxckinT August 16, 2023

gentleman car

A car where the driver has to open the other door because it wont open for the inside because its broken.

my dads has a car is a two door and only the drivers side door works. We were at the mall and he said this is a gentleman car Ill get that door.

by Coreydlady April 11, 2016

First gentleman

First gentleman or first dude if he's not a gentleman is what the husband of a female president would be called. The primo uomo.

The first gentleman was as good at sports, cooking, welding, or sewing as those girls (his competitive sisters), and he straightened them right out.

by The Original Agahnim January 12, 2022