Lily loves living in Manhattan. She also loves her hip apartment on the Upper East Side that she shares with her gay best friend James. James and her had been the best of friends since junior high and he would follow her to the ends of the earth. Over a couple glasses of wine on a relaxing Sunday night, Lily admits that she has never really had an orgasm and James admits that he's always wondered what it was like to be with a woman.
They laugh about their funny little secrets until the following weekend when the two join a few friends for a night on the town. Stumbling home in a drunken stupor, James and Lily both decide to take care of their little secrets and have a passionate night of sex; James really knows how to please his partner. Lily gets her first orgasm and James finds out what it's like to be with a woman...