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.
by Tootsiesocks July 10, 2018
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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.
by Lisa1982 March 16, 2010
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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.
by Lil' Shammie August 20, 2013
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Before intercourse, one inserts a lucky rabbits foot into the anal cavity of ones partner in order to ensure a quality time.
My girlfriend had a bad week so I gave her an ootsie tootsie.
by Sabby, MD PhD DVM October 21, 2018
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A synonym of the stinky pinky the tootsie hook is the act of fingering your sexual partner in the ass with one's pinky. A distant cousin of the finger blast, the tootsie hook works best on people with really tight assholes.
"That ass is so tight, I just wanna give it the tootsie hook."
"Before I anally penetrate, I like to start off with a really good tootsie hook."
by Kyle January 19, 2005
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An individual who demonstrates prestige in the buttocks department. In laymans terms; A cutie with a booty.
"Yo B check out that Lauren H.... she a tootsy pants fo shizo.
by B..e...a...n..... February 28, 2009
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