This essay explores the emergence of a form of sexual desire that did not strictly exist before the late 20th century—desire for the “pre-op” male-to-female (MTF) transsexual woman—a partially feminized male-bodied person who typically has breasts developed through hormone therapy or breast augmentation and some other female characteristics but who has not yet undergone female-to-male sex-reassignment surgery. The historical development of this new form of sexual desire is documented, in part, by the emergence of the transsexual pornographic video as a heterosexual male genre. The primary focus of this article is on the male spectator, with a secondary emphasis on the “male” performer. It explores how both male performers and consumers self-identify, what concepts of gender that both performers and consumers hold, and how the adult entertainment industry organizes and reflects sex and gender conventions and practices.