tailing 

To follow someone without being noticed.
To be a shadow of someone.

1. I tailed him to his home
2. Tailing Mr. George was very hard because he was always looking behind.

tailing by George Betsis December 29, 2008

tailing 

Rhis is when you have a penis and you push it in between your legs and make it look like a tail. then someone gives you a wedgie and when your penis hurts who ever gave you the wedgie has to now give you a blowjob.(works better with a big penis)

When i was iwth my friends they payed me and my friends 20$ each to tail each other. So first i got tailed and it hurt, but then i had to tail him and he has such a hairy rod, balls, gooch, and ass so right when he cummed they held me down and he stuck his ass in my face. and this is tailing

tailing by wedgie June 20, 2007

huff-tailing

Spending time exploring what can be accomplished on a motel bed after dropping coins into the "Magic Fingers" device. In honor of John Houghtaling, inventor of the Magic Fingers, who passed away in 2009.

With another couple days' driving ahead of them, Mia and JJ thought they should hit the laundromat, but nobody else was going to be smelling them in that junker they'd borrowed, so all their quarters went toward some surprisingly intimate huff-tailing on the saggy motel mattress.

huff-tailing by rotifera June 26, 2009

high tailing 

Runnin yo ass off

You jimmy was getting chased by the jake, I saw him high tailing round bleeker street

high tailing by Creboy November 29, 2013

kite tailing

When a girl's tampon string hangs out of her underwear/bathing suit etc.

Did you see Sharon at the pool yesterday? She was kite tailing hardcore.

kite tailing by Fraboli May 25, 2017

Raccoon Tailing 

A game where two people excrete a turd but force their sphincter to halt the expulsion of the turd mid-way, and proceed to sword fight with said excretory rods. The objective of the game is to knock the turd off the opponents' asshole.

Brad: Yo, I found a turd in the shower this morning. WHAT THE FUCK!?

Chad: Yo, my bad. Thad and I were fucked up and started raccoon tailing last night.

Raccoon Tailing by partisanwarrior97 April 29, 2019

Pussy Tailing 

Pussy tailing is when a Guy likes a Girl and follows her around trying to get into her pants. The guy will attempt to do this by complementing her, admiring her, sticking up for her and generally flirting wit her.

Also related to cock chasing which is when a girl follows a guy around because she likes him. Same as pussy tailing but roles reversed

Guy 1: *hanging wit agroup of girls* Hahahahahahaha *laughing at a poor joke* thats so good
Guy 2: *away from group talking to his real mates* Look at Dave, hes pussy tailing again. Twat.
Girl 1: hahahahahahahahahahaha

Pussy Tailing by TheYoungster April 22, 2010