I walked into Wills room and lets just say it was a one gentleman in a pantalona situation he did not want me to see.
by good_t-boning October 21, 2020
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
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
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.
by Anorien May 17, 2025
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
When a gentleman or sir takes a walk to let one rip out of courtesy to spare others from the rotten stench.
by BlaineTudor August 19, 2019
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.”
“Uncle Billy is a gentleman bachelor.”
by izaruru May 30, 2023
When a guy remembers a girl's favorite sexual activities to make sex as enjoyable for her as it is for him.
A girl I used to hook up with wanted to have sex once again, so I relied on my memory for a decent gentleman's fuck.
by Truthisalie November 28, 2015