The sex act of taking your dirty hairy underwear off while doggy-style and asking the woman if she wants a Hairy Tootsie Roll, the shoving your hairy skid mark underwear in her mouth.
by Snipedog22 January 23, 2013

It's a good thing Mark is into scat since Barbara gave me a tootsie roll pop when we double teamed her.
by chris giocondo April 19, 2006

by ric_IH December 16, 2007

A massage technique where the masseuse simultaneously sucks on the client’s big toe and inserts a thumb into their anus.
When you go to Massage Envy, don’t forget to ask for the Sloppy Tootsie Thumb Plugger from the secret menu.
by ellllllllllle December 21, 2019

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.
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"
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

Her: I’m on my period
You: Just suck my tootsie roll before you go
Or
Him: You ugly af
You: suck my tootsie roll
You: Just suck my tootsie roll before you go
Or
Him: You ugly af
You: suck my tootsie roll
by Suckmytootsieroll April 27, 2020

Things were going great until she started doing Tootsie Pop Owl Queefs - " Ah one! Ahhh Two! Ahhhh Threeeeeee!"
by Ghostington September 5, 2021
