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
by wedgie May 31, 2007
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.
by George Betsis June 10, 2007

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