A skirt or a pair of shorts that ride high over a woman's backside. Used by some prostitutes in poor urban areas to advertise their expertise in backdoor activties. Also used to describe a young girl who is desperate in winning favor or attention from their boyfriends(at a time when anal sex was considered taboo). Also used to describe A gay man faggot.
"I'm going to the Avenue Club tonight to catch me a tailskirt."
by Marleau Sterling October 04, 2006