When a sexual partner is licking a mans “tootsie pop” or penis and then he asks how many licks till you get to the center of my tootsie pop, the woman then licks the mans penis 3 times then proceeds to chomp down on the mans penis, causing him great pain but squeezing the cum, or center of the tootsie pop out.
Friend 1: “Hey I heard that Katie discovered how many licks it takes to get to the Center of the Tootsie Pop.”
Friend 2: “Ya, she left teeth marks and it hurt like a bitch but man did she find that center good!”
Friend 2: “Ya, she left teeth marks and it hurt like a bitch but man did she find that center good!”
by Ohneil69420 October 29, 2019
Things were going great until she started doing Tootsie Pop Owl Queefs - " Ah one! Ahhh Two! Ahhhh Threeeeeee!"
by Ghostington September 05, 2021
The next level of the Milwaukee Tootsie Pop. Instead of stopping at just shitting inside your Pink Sock, you have your friend or lover ejaculate on the feces filled prolapsed anus.
"I was going to just have a Milwaukee Tootsie Pop, but then Victor sneezed and accidentally jizzed on it. Now its a Cream City Tootsie Pop."
by Jay Shepherd May 27, 2023
It's a good thing Mark is into scat since Barbara gave me a tootsie roll pop when we double teamed her.
by chris giocondo March 25, 2006
It is a sentence...........but OK. how many licks does it take to get to the center of a tootsie roll pop
by Sparkle355 March 14, 2017
by Rusty cheese steak November 23, 2018
"Ah man, I should not have eaten all that Mexican Food before I got anally plundered. I'm not going to be able to hold my shit in much longer and my Pink Sock is going to become a Milwaukee Tootsie Pop."
by Jay Shepherd May 26, 2023