Milwaukee Tootsie Pop

When one has a Pink Sock and takes a shit in the pink mass that is their own prolapsed anus.

"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

Dark chocolate tootsie roll

When a black man is getting jerked off and he is about to ejaculate.

Stacy had herself a real dark chocolate tootsie roll.

by Digger faggot September 14, 2016

Wisconsin Tootsie Roll

Where an Asian man puts his penis in cheese

Chen got drunk and did a Wisconsin Tootsie Roll.

by PunchMunch August 13, 2024

tootsie

a feminine gay man. calling someone a tootsie can be both derogatory or playful, it really depends on the context in which it is used.

derogatory: "stupid fucking tootsie... i bet he can't even tie his own shoes!"

playful: "i see you staring at him. you must really like him, huh, tootsie?"

by delaanii July 30, 2020

360 tootsie roll

A sexual maneuver in where the participants assume the 69 position and then proceed to rotate on the Y axis 360 degrees.

Man: I 360 tootsie rolled my girl last night
Other Man: I've heard that drives the girls wild.

by keifchief November 28, 2018

Tootsie Rolled

The act of defecating inside of a condom and then inserting the condom into a woman's vagina.

Friend: "Hey bro, how did your date with that girl go last night?
Me: "It got a little weird, we Tootsie Rolled on the top of an old Indian burial ground by midnight."

by Gunner25 January 1, 2012

Tootsie Tot Puddie Pop

Tootsie Tot Puddie Pop (v.):
The unhinged, wide-eyed, saliva-dripping act of sucking on someone’s toes like you're a Victorian orphan who just got handed a Tootsie Pop after fasting through a plague. Usually involves noises that would make a soup kitchen blush and eye contact intense enough to spiritually confuse the recipient.

Also used as a noun to refer to someone who specializes in the practice, e.g. "He’s a certified Tootsie Tot Puddie Pop."

"Bro came home drunk and apparently went full Tootsie Tot Puddie Pop on her feet. She said his tongue was doing straight morse code on her pinky toe!"

by sniffyforastiffy? May 27, 2025