Bree, a male to female pre-operative transsexual living in California takes a road trip to New York when she learns that she has a teenage hustler for a son who needs her help.

Thirteen-year-old Henry Wheeler struggles to be the man of his house and care for his reclusive mother Adele, all the while confronting the pangs of adolescence. Henry and his mother encounter Frank Chambers, an intimidating man clearly in need of help. Frank convinces them to take him into their home and later is revealed to be an escaped convict. The events of this long Labor Day weekend will shape them for the rest of their lives.