Top definition
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 March 26, 2007
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2
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 07, 2008
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