toledo tootsie roll

To take a shit in ones hand, and proceed to stick just the head of the shit inside ones partner, then take the unprotruded end of the shit in both hands and proceed to roll it like Martha Stewart would roll dough.

Lee - "Dang Mark, I heard you gave her a Toledo Tootsie Roll."
Mark - " yeah I know man it was awesome but now my hands are covered in shit so I just wiped it on her."
Lee - "that sounds awesome I would have definitely rubbed it all over."

by Steve scuba September 22, 2017

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

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

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

Lennie Tootsie Roll

When you make out with a girl in a sleeping bag and she shits on you.

Jenny gave me a Lennie Tootsie Roll lastnight.

Jenny has a case of the Lennie Tootsie Rolls.

by Hotel Whiskey November 27, 2019

California Tootsie Roll

When he/she pisses you off so much that you take a dump on the person in your sleep

Just wait… If she pisses me off again i’m going to giver her a California Tootsie Roll

by ManiacMonsterMalcom July 14, 2025

Tootsie roll

Calling someone (usually a man) queer for liking feminine stuff or kissing boys. It is basically the same as calling a feminine man a twinkie or using "gay" to shame a homosexual, but in a funny way.

*watching Winx Club* Woo yeah! Boyyyyyyyyyyy!
Guy stalking on him: HOLY SHIT OUR BOSS IS A MASSIVE TOOTSIE ROLL!

by Pickle_ur_Tickle April 30, 2024