A contemporary comedy by Felipe Ossa, Why Does It Sting When I Pee? follows Andrew Walters, a gay actor whose unemployment, looming eviction and struggle to play straight on stage are pushing him to the brink. He yearns to reinvent himself but spends his increasingly inert days watching prison porn. Then it hits him: he needs to go to jail himself. But how does he get there? Enter a mercenary mother, her 13-year old son, and an actress friend hungry for a role on Law & Order, and Andrew learns that dreams can come true.