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

Rowdy Gentleman

A Rowdy Gentleman is a male that can make anybody comfortable in any situation. They are typically found with young women, drinking in excess, and participating in extremely adventurous activities. When the word Rowdy and Gentleman are combined and used to describe somebody, it is the highest compliment that can be used to describe a man.

Wow look, that guy just walked up to the bar, bought those girls shots, kissed one, and smacked the other two's asses, he must be a Rowdy Gentleman!

by anonymous September 10, 2016

being gentle

Apparently it means stopping for 60 seconds before, you know, getting going.

"Now then, you know what we've said about being gentle ...."

by Bad Grandad April 21, 2017

The Gentleman

The Gentleman is the act of coming inside a condom whilst it's in a girls mouth. You get the effects of swallow but she has no salty backwash.

I liked her enough to be the Gentleman but not enough to pull out

by Sydney Bear July 11, 2017

A Gentlemen's Race

A race wear two (or more) men start ejaculating at the same time and whoever finishes first, wins the race.

"Hey man I heard they had a Gentlemen's race in the men's bathroom right now."

by JJohn7 August 9, 2017

Pervy Gentleman

A huge pervert who instead of pushing women to fit their pervy needs, is nice and constrains themselves from being over perverted. But also can control their level of pervertedness if needed.

Wow! Kale is such a Pervy Gentleman!

by VoidStormYT February 10, 2018

first gentleman

The husband of a president.

If Hillary Clinton gets elected president, Bill Clinton will be the first first gentleman.
If Pete Buttigieg gets elected president, Chasten Glezman will be the first first gentleman.

by gagiodilo August 20, 2019