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shemales with pigtails 

Transvestites that have both a penis and a pigtail in their crotch area or a pigtail above their ass.
Shemales with Pigtails are in the movie The Hangover 2
Damn if these officers in my pigtail aren't annoying.
Pigtail by Jack Daniels 2011 November 4, 2011
when a cop (pig) is trailing you (tail)
it was awful, picked up a skank ass hooker but i had a pigtail and i got busted before i busted
pigtail by Spangoul March 18, 2007

pulling pigtails 

after i figured out that she was just pulling my pigtails i made sweet sweet love to her causing her pleasrue beyond any that she had felt before, because i am so skilled and awesome!
pulling pigtails by boris! August 14, 2003
During intercourse, a man spins on top of a female while still in her, (like a breakdancer) and there's a chance his member could get stuck and twisted like a pigtail.
I want to pigtail my girl because I am feelling athletic.
Pigtail by Treflexswedisha August 12, 2015