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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.
cherry tootsie pop by Bull26 April 6, 2007
Words you can keep

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."
Cherry Tootsie Pop by Shizzynat April 7, 2008
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