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tootsie roll exchange 

When a person (or animal-- see below) defecates directly into the anus of a willing sexual partner. This is accomplished by both partners getting on their hands and knees, or laying on their backs with legs in the air, with their buttocks pressed together. With a lot of patience and experience, an expert pitcher and catcher can oftentimes maintain a back-and-forth for hours of pleasure.

It is widely debated whether or not the Tootsie Roll Exchange happens in nature, or if it is a man-made creation; this has caused a rift in the animal sex-science community, spurring many heated arguments, and even one slap-fight at the annual Animal Sexuality-Science Convention in Zurich (citation needed).
Things started to heat up when she suggested a Tootsie Roll Exchange after just three dates.
tootsie roll exchange by clute April 1, 2011

Tootsie toss 

Defecating in the shower, catching it in your hand, and throwing it over into the toilet.
I was running late the other day, so I just did a quick tootsie toss in the morning.

tootsie boots

A sophisticated way of saying socks . A way I which you tootsies are being warthed by your tootsie boots
Jamie was wearing tootsie boots to sleep, what a freak.

Tootsie-Matized 

Tootsie-Matized. Another word for a penis. It's hypnotizing, your mind stays focused on how you will worship and please it, although you are not near it, it'll leave you dreaming about what you will do with it and appreciate it because you know he's worth it.
My baby got me tootsie matized, he got me feining. I'm Tootsie-Matized.
Tootsie-Matized by Lisa1982 March 16, 2010

Tootsie weekend 

A weekend in which a man dresses in women's clothing and assumes a female identity in order to determine whether or not he would enjoy being a woman. Inspired by the movie "Tootsie" starring Dustin Hoffman.

Not to be confused with a Doubtfire holiday in which a man dresses as a woman to secretly spend time with his children.
1.)
Brett: Hey, man! You wanna come over on Saturday and play "Call of Duty"?
Marty: No, thanks. I'm gonna do a Tootsie weekend.

2.)
Devin: Do you like mascara?
JJ: Yeah, I kinda do. I think I'm gonna do a Tootsie weekend.

3.)
Ryan: Hey, how was your Tootsie weekend?
Gus: Great. I think I'm gonna become a woman.
Tootsie weekend by Lil' Shammie August 21, 2013

Tootsie Roll Mustache 

(noun) Fecal mater on your upper lip obtained after performing anal cunnilingus (Often in the form of a Tootsie Roll Canoli)
Bieber was giving me some good Tootsie Roll Canoli and I gave him a little Tootsie Roll Mustache in return.