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."
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.
a joking slur to describe a gay person
"shut up tootsie pop"
The OG commercial that everyone saw
How many licks would it take to make it to the center of a tootsie pop? The world may never know!
A person that is hard to handle
Man that guy is such a Tootsie Pop
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
When you take your friends toe and shove it in your ass and then take it back out and cut it off. Then wrap it up in paper and let chill. When you proceed to eat it it will be like a tootsie pop.
Bro I had the best damn Jamaican tootsie pop ever last night with Humey.