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. Defines the ultimate goal of any girl where her intent is to engulf your entire member in a near scandalous blow job.
by Angus McCracken March 26, 2020
Get the Tip to Taintmug. by miriamz February 13, 2018
Get the tip of the sloungmug. eating ass with a spoon
by dildor defender of porn December 2, 2016
Get the weezing bag of dick tipsmug. 
When the waitress hands you the bill and the tip starts at 18% and ends at 25%. You feel guilty and leave a 25% tip even though the service and food was not too good
Tom - Hey Matt, looks like they're asking for a $25 tip for out crappy $100 lunch
Matt - Hey, they're just guilt tipping you. Leave $10 - They're lucky to get it
Matt - Hey, they're just guilt tipping you. Leave $10 - They're lucky to get it
by TJ2000 September 9, 2022
Get the Guilt Tippingmug. A sex act in which one partner defecates into the foreskin, filling it with fecal matter, the guy afterwards squeezes from the base upwards to extrude the shit onto the desired surface.
Friend: “Hey man have you tried the Kentucky frosting tip with your girl yet?”
Me: “yeah man! I gave her some chocolate flowers right on her nipples!”
Me: “yeah man! I gave her some chocolate flowers right on her nipples!”
by Schmoopydoop July 6, 2020
Get the Kentucky frosting tipmug.