tootsie pop

term of endearment; sweet nickname for a sweet person

Brandon is my tootsie pop!

by sheboygan June 8, 2005

cherry tootsie pop

having anal sex with a girl on her period, followed by vaginal intercourse, followed by blowjob

Oh, Mackenzie, I just love cherry tootsie pops!

What's that?

When you let a guy fuck you in the ass while you're on your period, then let him put it in your pussy, then suck him off.

by Bull26 April 6, 2007

Tootsie Pop

When someone falls asleep and gets a baguette shoved up their ass with a chocolate flavored donut put on the tip. The friends test how many licks it takes to get to the center.

Holy Cow look at that huge Tootsie Pop coming out of Vinny's ass, I cant wait to eat that shit up.

by the cotck August 20, 2009

Cream City Tootsie Pop

The next level of the Milwaukee Tootsie Pop. Instead of stopping at just shitting inside your Pink Sock, you have your friend or lover ejaculate on the feces filled prolapsed anus.

"I was going to just have a Milwaukee Tootsie Pop, but then Victor sneezed and accidentally jizzed on it. Now its a Cream City Tootsie Pop."

by Jay Shepherd May 26, 2023

tootsie pop

When a girl gives a guy a blow job and she makes a popping sound with her mouth.

Dam, that girl can tootsie pop!

by http://warez-reviews.blogspot.com/ December 13, 2007

Cherry Tootsie Pop

An act involving a menstruating woman and a second subject, in which the menstruating woman takes a mustache ride and simultaneously releases her bowels, thereby covering the subject's face in the red and brown mixture.

"Last night that kinky bitch showed me how many licks it takes to get to the center of a Cherry Tootsie Pop."

by Shizzynat April 7, 2008

tootsie pop

When a woman has her menstrual cycle, the male inserts his penis in the rear then in the front.

My wife was appaled when I suggested the tootsie pop last night.

by woopwoop123456789 August 17, 2008