Top Definition
Noun- Unknowingly having poop under your sheets when climbing into bed.


Tootsie Rolling, the act of taking a dump under someone else's sheets without their knowledge, with the intent of ruining that person's night.
Dude, I Tootsie Rolled that asshole, and it's a sloppy one.
by Papua New Guinea Pig August 10, 2011
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 December 31, 2011

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