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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.
An Asian man's penis
Lin Da's 3 inch yellow tootsie roll couldn't please his wife.
Is defined as the sexual act of giving anal following the male or female licking fecal matter off of the penis and or testicles
Person 1: How was your date with Jane
Person 2: It was great! I tired anal for the first time and slipped her the old Chocolate Tootsie Pop
Where an Asian man puts his penis in cheese
Chen got drunk and did a Wisconsin Tootsie Roll.