Dorothy's Boy follows the life of an outcast transgendered boy into womanhood. Set small town Pennsylvania in the 1950's, young Kent tries to cope with desires and confusions which estrange him among the towns folk. Kent is befriended by Benny, a preacher's son. Benny comes from a deeply dysfunctional family. The two boys become inseparable throughout their childhoods but Benny's attraction to Kent eventually becomes more than friendship. Kent's lack of interest causes them to fight and forces them to go their separate ways. Years pass while Kent attempts to live as a man. He finally undergoes a sex change and becomes Kelly, losing everyone she holds dear. She starts anew in 1980's Silicon Valley, far from the Fundamentalist Christian society she once endured. She lives alone but is secretly in love with her neighbor, Ellen as Benny reappears carrying the past with him. Their fateful reunion brings shocking consequences.