Used to describe a woman who is rather unattractive, except at her center, namely, her ass; an otherwise ugly woman with a good butt.
"Look at that tootsie-pop, man... if only the rest of her matched up with her ass."
by Pseudonym November 10, 2004
The act of sneaking your finger into your buttcrack or butthole and having a girl unknowingly suck on that finger
"Yo dude, i gave that bitch a tootsie pop last night."
by kcchiefs07 September 28, 2007
term of endearment; sweet nickname for a sweet person
Brandon is my tootsie pop!
by sheboygan June 02, 2005
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
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 July 21, 2008
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/ November 15, 2007
When a man Jizzums in a girls butt crack, allows it to harden then procedes to lick it all up only using his tounge, thus getting to the center of her chocolate tootsie pop.
Last night I came in a girls butt crack and this other girl licked it out like a tootsie pop
by Dan Scragg July 28, 2006