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When one has a Pink Sock and takes a shit in the pink mass that is their own prolapsed anus.
"Ah man, I should not have eaten all that Mexican Food before I got anally plundered. I'm not going to be able to hold my shit in much longer and my Pink Sock is going to become a Milwaukee Tootsie Pop."
When a black man is getting jerked off and he is about to ejaculate.
Stacy had herself a real dark chocolate tootsie roll.
A man named Riley that like to kidnap Italians
A dumb guy name crooked tootsie roll that has no life
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.
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.
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Stick the lollipop in her ass and take a nice big suck.
Dude I dipped a big inside out tootsie pop from my girl’s butthole last night.