Books - Books that directly address the topic of Christianity and transgenderism.
Related Books - Books that don't address both Christianity and transgenderism but may be helpful
Transgenderism in Christian Media - Discussions of transgenderism in the Christian mainstream media
Call Me Malcolm - A documentary about a transman in seminary, exploring how to integrate his gender into his life.
Transfigurations--Transgressing Gender in the Bible - One-person, multi-character, multi-gender play about gender variant people in the Bible.
Transgender Jesus - The gospel narrative imagining Jesus as transman (ie, a female-to-male transexual)
Antony Hegarty - Along with their band, Antony and the Johnsons, is a genderqueer singer-songwriter and occaisionally transgender and Christian themes like Rapture. Antony has an incredible voice - somewhere between female and male, somewhere between earth and heaven.
Kinky Boots - Despite the name, this film is sexually tame, although they do acknowledge the concept of "sexy" (scary!). It's not a Christian film, per se, but has wonderful Christian themes. The main character has through a personal journey, deciding what to do with the family shoe business he has inherited. A genderqueer drag queen allies with him, teaching him using several Christological methods like welcoming the outcasts, dying to self, and walking a mile in a transvestite's shoes. Based on a true story.
The Believers - The Believers is a feature documentary that shatters assumptions about faith, gender, and religion. Built around the world's first transgender gospel choir, the film portrays the choir's dilemma - how to reconcile their gender identity with the widespread belief that changing one's gender goes against the word of God.