Loveless Momentum

Reiichi Miyoshi is a professional jazz musician who has a policy of never having a serious boyfriend or girlfriend. He prefers to keep his love life casual with a revolving door of hedonistic one-night stands.When he swoops in to rescue what appears to be a damsel in distress from a group of rowdy men one day, he soon finds out that his latest paramour is no damsel at all, but the crossdresser Sara Aogiri. Sara is determined to have the egotistical Miyoshi all to himself, but Miyoshi isn't going to date anyone seriously without some extreme convincing.

(Source: Animate International)