Gun Hill Road (2011)

An ex-con struggles to understand his son's sexual transformation in Gun Hill Road (2011). Named after the street in a bad neighborhood in The Bronx, this touching tale of acceptance stars Esai Morales as Enrique, a macho ex-con fresh off of serving a three-year sentence in prison. Enriquereturns home thinking things will be just like they were before he was locked up, only to find that his wife has moved on and is sleeping with someone else, and his teenage son Michael (Harmony Santana) has begun the process of transitioning into a woman named Vanessa. Needless to say, both those things are pretty hard for Enrique to accept, especially after serving time in a place where men who are treated like women don't have the easiest time. For far longer than even the most ignorant dad should, Enrique refuses to accept Vanessa's transition, and forces her to play baseball, go to a brothel, and do all sorts of other macho things in hopes she'll want to become Michael again. Considering she's already on hormones and very obviously happy with her decision, none of that works and the interactions between father and daughter become awkward and hostile. There are some rough scenes to watch, but eventually the prisoner papa will come to accept that he's a girl dad now. Transgender actress Harmony Santana stars as Michael/Vanessa Rodriguez, and 44 minutes in she and her superbly sculpted date Tyrone Brown deflower each other in a tender scene of transgendered teenage lovin'. Gotta hand it to Vanessa, that is one fine black man to become a woman with! But if dad-meat is more your style, just fast-forward to the scenes where Esai goes shirtless in the shower and in bed. Gun Hill Road will make you empty the entire load trapped in your chamber!