The film describes the organization and its history. It presents a series of interviews with NAMBLA members who describe their feelings towards boys and justifications for such feelings.
Chris & Don tells the story of a romance that began on the beaches of Santa Monica in the 1950s, when Christopher Isherwood at age 48 met Don Bachardy who then was eighteen years old. Isherwood, an established author with works such as The Berlin Stories, which helped inspire much of Cabaret, helped Bachardy discover and develop his affinity for drawing and painting as he became a renowned portrait painter during the second half of the 20th century to the present. The documentary includes insight from friends, including Liza Minnelli and John Boorman, who tell of the countless struggles the two faced as one of the first openly gay couples in Hollywood. Despite the age difference, the couple endured until Isherwood succumbed to prostate cancer in 1986.
Born as Kyle Dean in a conservative area of North Carolina, Stacey "Hollywood" Dean was never truly accepted in her high school and was always called "creature" because of her desire to become a woman. Ostracized, Stacey left her home town to go to Hollywood, hoping to find more acceptance there. Four years later Stacey is returning home to visit with her parents in her new persona as Stacey Hollywood.
According to the film, prisoners in the United States are incarcerated in men's or women's prisons depending on their biological sex (or, more specifically, whether they have male or female genitals), and not their gender identity. As a result, pre-operative trans women are incarcerated in men's prisons, and trans men in women's prisons.