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
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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 19, 2017
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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
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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 01, 2012
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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 28, 2019
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Tootsie roll bingo

I'm headed to the club to play some tootsie roll bingo!
by Shiteshady February 27, 2017
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