Crossing(2007)

Overview:

A romantic thriller, Crossing follows the story of macho Danarama (Sebastian Spence), who makes a deathbed promise to his father to turn their family from petty gangsters to upright brokerage owners. The only thing standing in Daniel's way is his newly discovered desire to dress up like a girl. Embroiling himself in an intense romance with a blackmailing prostitute (Crystal Buble), Daniel must find his way through a maze of disgrace and pleasure to discover where his true loyalties lie.