The sexual position that occurs when your girlfriend or a random girl is in the bathroom puking after having to much to drink. but your still having sex with her in the wheelbarrow position while holding her hair. Thus being a gentleman for holding her hair.
On Saturday, Jessica came over and she had to much to drink. She spent a lot of time in the bathroom puking but her sex drive was still crazy so I performed the Gentleman's Wheelbarrow
by DanAppleLickrTipperOswinNipper April 13, 2020
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
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
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