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

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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 1, 2012

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A competition between two people when they have their legs interlocked. Their anuses firm pressed together. Then one person begins to push a large length of firm excrement completely into the other persons anus. The goal of the person receiving is to push the excrement back into the originating person's body as if it were a normal bowel movement.

I tried to give bro that Tokyo Tootsie Roll but he pushed it back.

On our date we stayed up all night playing Tokyo Tootsie Roll.

by anonymous July 18, 2024

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Creamsicle Tootsie Roll

A sexual act, in which a man of standard height or stature, grabs a hold of a midget, or vertically challenged female, and holds her upside down. He may bear hug her lower body, or use both hands to hold her by the ankles if he has the hand strength to do so. But while she is being held upside down, she is performing oral sex on him, and simultaneously he is licking and sucking on all ten of her toes. This must continue until the man ejaculates into the dwarf's mouth

Little Gina from the strip club, she's asleep in the other room right now, she blacked out while I creamsicle tootsie rolled her... I had to finish bro, her toes tasted like pig asshole

by Kramardi September 15, 2022

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