Boy I Am (2006) (Transgender)

BOY I AM looks at the experiences of three transgender men - Nicco, Norie and Keegan - following them throughout some major events of their transitions, including starting testosterone and getting chest surgery. The film also includes feminists, lesbians, activists and theorists voicing their opinions and questions about trans issues. Tackling the resistance of some women in feminists and lesbian communities who view FTM transitioning as at best a "trend" or at worst an anti-feminist act that taps into male privilege, this groundbreaking film opens up a dialog between the lesbian, feminist, and transgender communities while also promoting understanding of transgender issues for general audiences.

http://www.imdb.com/title/tt1024954/