tootsie roll fruit cup 

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"

tootsie roll fruit cup by andrewn September 17, 2013

Tootsie Roll Stroll 

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!

Tootsie Roll Stroll by maximillion September 3, 2013

Tootsie Popper 

A person that takes someone's anal virginity.

He was Sharon's tootsie popper

Tootsie Popper by T-Rod Money Pubes October 14, 2013

tootsie hook 

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."

tootsie hook by Kyle January 19, 2005

Tootsie Roll

A woman's nipples, especially dark nipples,

as in "whoop there it is, let me see your tootsie rolls"

Tootsie Roll by Urban Stephen June 10, 2007

Tootsie Roll in the Valley 

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.

Tootsie Roll in the Valley by Thaddeus Q. Wellington June 5, 2005

Tootsie Pop 

Used to describe a woman who is rather unattractive, except at her center, namely, her ass; an otherwise ugly woman with a good butt.

"Look at that tootsie-pop, man... if only the rest of her matched up with her ass."

Tootsie Pop by Pseudonym November 10, 2004