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A 70yo man's penis while watching porn trying to jack off ..
Old man Raymond proved that at any age you can still get that tootsie roll to rise up!
by MR Bownes August 12, 2025
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tootsie roll exchange

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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.
by clute April 1, 2011
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Tootsie Roll Mustache

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(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.
by admirallenny November 6, 2014
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tootsie roll fruit cup

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The second best insult to be used on a city boy or hockey player. Indicates they are both soft (like a tootsie roll) and gay (like a fruit cup). Thus calling them soft and gay in one phrase. As seen in Letterkenny problems on Youtube, a series of comedy skits about small town life problems.
The first best insult is ten ply.
Guy 1- Ladies love the flow, bro.
Guy 2-Buddy the only thing ladies love is when you quit talking.

Guy 1 - What'd you say.
Guy 2- You heard me. Buddy your softer than a "tootsie roll fruit cup"
by andrewn September 17, 2013
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Tootsie Roll Stroll

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noun.

1. During sexual intercourse, the moment when the man's penis slips out of the woman's vagina and passes against the anus. He proceeds to slide it in without any objection. He is now performing anal sex, & strolling down her brown hole.

2. Casual anal sex
Trevor: Man, had a really great night with my girlfriend last night.

Alex: Sounds lame, Trev.

Trevor: No, dude. She finally take that Tootsie Roll Stroll.

Alex: Damn, T. Great night indeed!
by maximillion September 3, 2013
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When your partner is on her back and you're titty fucking her, you accidentally shit on her stomach.
I was TF'in my girl last night and straining to get a nut when I accidentally left a tootsie roll in the valley.
by Thaddeus Q. Wellington June 5, 2005
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Tootsie Roll Nipples

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The large, brown, thumb-like nipples that accompany over-use of steroids.
Hey, did you see Barry Bonds' Tootsie Roll Nipples last week? If those things had thumb joints, he could eat chinese food without a fork!
by undertowpull December 16, 2011
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