ABSTRACT This article offers an analysis of hardcore films by Arthur J. Bressan, Jr, whose status as a pioneer of HIV/AIDS cinema has overshadowed his prolific work as a director of gay pornography. By focusing on the urban landscape of San Francisco as central to the dramaturgy of his early pornographic films, the article considers the documentary impulse evident in Bressan’s representation of urban queer topographies as inseparable from the films’ erotic charge. The article puts critical pressure on representations of cruising, the closet of sexual secrecy, and the prison as a site of sexual fantasy as erotic and spatial tropes central to Bressan’s queer countermapping of San Francisco. The urban landscape and its infrastructures are analyzed as central to Bressan’s cinematic mediation of San Francisco, and are reframed in this article as the scaffolding for the films’ thematic interest in queer pedagogy, gay visibility, and sexual liberation.