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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


gentleman's shave

like a hitler except you use you feces to give her/him a moustache and a soul patch, like a frenchman

mikey went to sleep first and i didnt wipe all the way so i gave him a gentleman's shave. he never slept over my house again.

by the black t-dog November 14, 2009


Gentleman's Shave

This is when you shave your Genitals and butt hole in preparation for the summer months at the beach.

"Bro, I need to have a gentleman's shave before i can to go Ibiza"

by Grandmaster Pope March 08, 2020


A gentleman but not a gentle-man

A definition first created by Stefanos Fotiadis meaning someone who is a man of refined manners, courtesy, and social standing, while also being a man who can be not so soft-spoken, and aggressive. Usually referring to the man's manner in sexual activities.

It has been said that I am a gentleman but not a gentle-man darling.

by Anorien May 17, 2025


Gentleman of the street

A polite word for word for homeless, vagabond, or any other person that lives on the street. Thousands of them in California.

"Jimmy was a gentleman of the street," his mother says. "He was a guy who was clean, responsible." She says he was a generous person who loved restaurants, cooking and people-watching.

by PeterBirdman88 June 13, 2018


Gentleman's walk

When a gentleman or sir takes a walk to let one rip out of courtesy to spare others from the rotten stench.

I've got a stinker on board love, just takin' a gentleman's walk...back soon

by BlaineTudor August 19, 2019


Gentleman Bachelor

Another word for a gay man. Especially one that stays a bachelor to “focus on work.” He may or may not have a close “coworker.”

“Why did Uncle Billy bring his friend Larry to the family reunion?”
“Uncle Billy is a gentleman bachelor.”

by izaruru May 30, 2023