The gentleman's raptor claw 

Extension of the raptor claw; Where one seductively places the thumb into the anus of a woman while in the throes of passionate fisting.

Prudish pornstar: I can't believe he tried to give me the raptor claw on set.
Gentlemen caller: Baby, you've clearly never had The gentleman's raptor claw.

The gentleman's raptor claw by ThatJO February 3, 2018

relaxing the gentleman's way 

In a word- masturbating.

"Sorry, I can't come out tonight, I'm busy; I'm relaxing the gentleman's way."

relaxing the gentleman's way by CaptainWhizz June 25, 2009

to-relax-in-the-gentleman's-way 

to partake in "self pleasuring"

"wacking off"
"choking the chicken"
"knocking one out"

to-relax-in-the-gentleman's-way by rams May 21, 2003

The Gentleman's Cut 

Noun: A style of hair introduced to the world via the Andrew DeWitt Show (podcast). If you ask for the gentleman's hair cut the hair dresser will cut your hair however he or she feels is fit for a gentleman.

Man: I would like the gentleman's cut.
Hairdresser: The what?
Man: You know, something modern.

*Gets out clippers

The Gentleman's Cut by PoltRon June 2, 2014

The Gentleman's Knock 

Slapping or smacking a girl's crotch with your boner and then proceeding to not sleep with her.

"That slutty girl thought she was going to get it good, but he ended up giving her the Gentleman's Knock."

or

"He was too much of a gentleman to get in there, so he just knocked."

The Gentleman's Knock by Amynonomous May 13, 2014

The Gentleman's Disease 

A more elegant way of saying autism

My Doctor just told me I had the Gentleman's Disease

The Gentleman's Disease by MrAvacadoMan August 16, 2023

the gentleman's surprise 

Urban Dictionary-
The Herman, also known as, The Gentleman's Surprise.
To preform the Herman, ejaculate in an object that is commonly used by someone unbeknownst by the owner or frequent user of said object to leave a nice surprise. Such objects can be, but are not limited to, shoes, helmets, pockets, socks, hats, opened alcoholic drinks, and even wallets and purses, preferably while they are not in use.

"herman left the gentleman's surprise in my brother's helmat, hah hahhahahahahaha"

the gentleman's surprise by Austin Johnson/ Steve Sutton November 14, 2007