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

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

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

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

alaskan tootsie roll

The act of taking a shit outside in extreme cold weather, where the shit only gets half way out of your ass hole before freezing solid.

I had to hurry and take a dump out there before it became an alaskan tootsie roll.

by Webster definer March 24, 2024

Brazilian Tootsie Roll

When a male inserts his big toe into a woman’s anus, pulls it out and let’s her lick his big toe.

“I heard Jennifer’s into Brazilian Tootsie Rolls; must be a freak”

by DeepFriedAss October 7, 2020

Tootsie roll bingo

Another term for anal sex

I'm headed to the club to play some tootsie roll bingo!

by Shiteshady February 27, 2017