Transamerica

Southern Californian Bree Osbourne, who was formerly Stanley Chupak, has finally received the news for which she has been waiting: she has been approved for male-to-female sexual reassignment surgery. But before Margaret, her therapist, will allow her to go through with the surgery scheduled in a week's time, Bree has to deal with an unresolved issue from her past. Bree got a telephone call from a seventeen year old man named Toby Wilkins, who was looking for Stanley, his biological father. Toby is in a New York jail, he who supports himself by petty crime and hustling. Stanley/Bree knew nothing about Toby before the telephone call. Toby apparently is all alone in the world, with his mother having committed suicide and being estranged from his stepfather in Tennessee. Masquerading as a Christian social worker, Bree, not telling him either of her true identity or her transgendered status, bails Toby out of jail and tells him she will take him to Los Angeles, where Toby has aspirations of becoming a porn actor and reconnecting with his biological father. As Bree and Toby take their trans-American journey which includes some interesting encounters along the way, Bree has to decide what is best for Toby while having the foremost goal of making it back to Los Angeles for the scheduled surgery.

Bree, a pre-operative, male-to-female transsexual, holds down two jobs and saves every penny so that she can pay for one last operation that will make her a woman at last. One day, however, she receives a strange phone call. It appears that on the other side is Toby, apparently her son, who must be the product of a somewhat clumsy sexual encounter years ago when she was a man. He stays in New York, incarcerated. Bree flies from Los Angeles to New York in order to get the boy out of jail. At first she is reluctant to do so, but her therapist convinces her to face up to her past. The boy is handed over to her without a word of explanation and Toby believes the woman to be some Christian missionary determined to convert reprobates to Jesus; Bree sees no reason to clear up the misunderstanding. However, she finds out that the boy just wants to escape from her and hitchhike to Los Angeles. She persuades him to accompany her back to the west coast--secretly planning to leave him at his stepfather's along the way. Toby is happy to take her up on her offer.

One week before her sex-change operation, Bree receives a call from a 17-year-old identifying himself as her son from a college liaison. Bree's psychiatrist won't approve the surgery until Bree deals with this relationship, so Bree flies to New York City, bails the youth out of juvenile detention, and offers him a ride back to Los Angeles without disclosing that she is his father. Both her plans and his go awry, and as secrets will out, what might become a friendship (or more) founders. The lad's step-father, a sex-change support group, a peyote eater, a Navajo wrangler, and Bree's family all play their parts in this exploration of family, gender, and expectations.