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

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 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 Roll

A little douche bag.

Love him or hate him Adam Levine is a tootsie roll.

by Dan&LeesExcellentAdventures April 24, 2023

Tootsie-Roll-Smear

Your butthole.

"my tootsie-Roll-Smear itches."

by Heartmonger June 19, 2019

trump tootsie roll

A steaming dog turd wrapped in a candy wrapper with trumps face on it

those morons ate their trump tootsie roll and said, "please sir, may i have some more"

by The Phrogg May 7, 2025