Blue Haven (2001)

Two skateboarders search for the perfect swimming pool to skate, but $40,000 and a sex change later, they find true love instead. Henry and Fakie live a joyous simple life combing the city for a Blue Haven pool to skate. If only Fakie could find the forty grand he needs to bankroll his sex change. Luckily Fate intrudes to lend a helping hand but neither Henry nor Fakie anticipate that every weird accident is usually followed up by increasingly weird accidents.