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. Oh Jimmy, its freezing out here! Aren't you cold? (little does he know im testing him to see if he's a gentleman and give me his jacket
by uhhhhidkwhattonamemyselfyk April 14, 2022
Get the gentlemanmug. A queer or lesbian identifying woman (often in a backward cap) who exhibits "hey mamas" qualities but is a "golden retriever" at heart. Typically they come off as intimidating and douchey, but don't let that fool you, for she is a true gentleman.
I got this jacket from a frat gentleman last night at the club; she gave it to me because I was cold and told me to keep it.
by wrizzyfoshizzy January 7, 2023
Get the Frat Gentlemanmug. Bro 1: Yo, dawg, what's taking Parker so long?
Bro 2: He's giving himself a Gentleman Thrashing. He'll be out after he takes the tux off.
Bro 2: He's giving himself a Gentleman Thrashing. He'll be out after he takes the tux off.
by NattyChamps2021 July 27, 2022
Get the Gentleman Thrashingmug. 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. Windsor Relaxation Centre began as windsor’s first gentleman’s club. and has remained unlike any other, with a reputation built on the quality of our handpicked Pin-Ups who know how to pamper and tantalize you with the ultimate fantasy experience. We double the fun with our welcoming bar staff expertly handling your other senses over two bars, various VIP playrooms (with room service) to ensure the most comfortable conditions on your ideal night out. Windsor Relaxation Centre is Australia’s famous adult entertainment club in Windsor. To benefit our visitors, we also regularlly send out shops' coupons getting discounts to our loyal customers. In our adult service , our preimier adult service venues provide the best sexual services, massage and private girl out call in Sydney, Melbourne, Adelaide, Perth and Brisbane. We are one of Australia’s most preferred adult entertainment club.
Windsor Relaxation Centre began as windsor’s first gentleman’s club. and has remained unlike any other, with a reputation built on the quality of our handpicked Pin-Ups who know how to pamper and tantalize you with the ultimate fantasy experience.
by Windsore Relaxation April 21, 2022
Get the Windsor Relaxation Centre began as windsor’s first gentleman’s club. and has remained unlike any other, with a reputation built on the quality of our handpicked Pin-Ups who know how to pamper and tantalize you with the ultimate fantasy experience.mug.