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
Get the the gentleman's tipmug. A business flight in the late morning (i.e. 11 am) to avoid the crowds and to have enough time to masturbate before going to the airport
Gentleman 1: "Are you sure you're down for another strip club?"
Gentleman 2: "Yeah bro I don't have to get up early... I have a gentleman's flight!"
Gentleman 2: "Yeah bro I don't have to get up early... I have a gentleman's flight!"
by CKMeredith June 20, 2025
Get the Gentleman's Flightmug. "A gentleman's scratch" is when you have an itchy bumhole and you fart at just the right capacity to simultaneously release gas and itch your bumhole within the same manoeuvre
by ScottyFxckinT August 16, 2023
Get the A gentleman's scratchmug. Essentially the antithesis to the Madonna-whore complex where a woman may be sexually attracted to the dominant and agressive "gigolo" but may not see him as an ideal partner or spouse. On the other hand she romantically desires the mellow and submissive "gentleman" to be a husband and father to her children but may not respect him as a man or partner. The "gigolo" may possess dark human traits that are deemed "toxic" or "dangerous" such as Machiavellianism or could simply just be charismatic, masculine, and attractive, as well as being able to sexually satisfy the woman. Meanwhile the gentleman may possibly possess pure traits including sensitivity, emotional intelligence and even leadership qualities and financial success, but may also be shy, non-confrontational, passive-agressive, and submissive which at worst makes him more susceptible to molding and manipulation and may not sexually satisfy the woman.
Man 1: Did you see that girl Cheri give that millionaire dude her number
Man 2: yeah but she has a Gentleman-Gigolo Complex, and that guy isn't going for someone like her
Man 2: yeah but she has a Gentleman-Gigolo Complex, and that guy isn't going for someone like her
by TJ May 23, 2021
Get the Gentleman-Gigolo Complexmug. When a female places her mouth upon a male anus and the woman uses her tongue and lips to pleasure the male by way of anal oral sex, the male is receiving a gentleman’s grip.
I mounted the virgin, she proceeded to partake in a gentleman’s grip. All the joy in the world does not compare to the pleasure I felt from such a proper act of love and affection.
by Party McGraw March 14, 2023
Get the A gentleman’s gripmug. by _sillyguy_0 June 9, 2023
Get the The gentleman ghostmanmug. 