Originally from a Saturday Night Live episode.
Slang word for any white male who has a small penis who participates in a nude activity such as skinny-dipping. Often done by white males who think their penis is of big or average size.
Slang word for any white male who has a small penis who participates in a nude activity such as skinny-dipping. Often done by white males who think their penis is of big or average size.
I have no idea why John played strip poker with the girls, his small vanilla tootsie roll isn't going to impress them.
by Trent Easton May 22, 2006

You fuck a girl in the ass and she shits on your dick. Then you put it in her vagina pull it out and wipe it across her face while she sucks on your balls.
by iTheProphet November 29, 2011

The next level of the Milwaukee Tootsie Pop. Instead of stopping at just shitting inside your Pink Sock, you have your friend or lover ejaculate on the feces filled prolapsed anus.
"I was going to just have a Milwaukee Tootsie Pop, but then Victor sneezed and accidentally jizzed on it. Now its a Cream City Tootsie Pop."
by Jay Shepherd May 26, 2023

by P3R53RT August 18, 2020

I met and surpassed the tootise roll critical number, as i am now here suffering the consequences on the shitter.
by rudog September 8, 2005

by rudog September 26, 2005

A variation on the cleveland steamer where you are pokin your bitch in the ass, but she didnt take a poop before-hand, and you climax inside her rectum, and she takes a dump on your chest, and it resembles a frosting covered tootsie roll.
"I heard Reed got some of dat Eastern Washington Frosting Covered Tootsie-Roll from his skank last night. Truf."
by jram October 15, 2006
