Tijuana Tootsie Roll

The act of popping in a condom and freezing it. Once it’s good and frozen it’s deep fried, frozen again and inserted back into someone’s anus.

If you think an Alaskan Pipeline is cool, you should try a Tijuana Tootsie Roll. It’s like a twice baked potato for your butt.

by Captain SANDOS May 14, 2025

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

Tootsie Roll

A 70yo man's penis while watching porn trying to jack off ..

Old man Raymond proved that at any age you can still get that tootsie roll to rise up!

by MR Bownes August 12, 2025

Tootsie-Roll-Smear

Your butthole.

"my tootsie-Roll-Smear itches."

by Heartmonger June 19, 2019

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 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