ABSTRACT Anal fisting has often been caricatured as an aggressive, if not violent, mode of sexual and erotic practice between gay men, circumscribed by discourses of risk, danger, and even death. In this study, I explore how a sample of 28 South African gay men who regularly incorporate anal fisting into their preferred sexual practices construct and understand the experience of intimacy in the practices and relations of their fist-fucking. Through sexual scripting theory and a Thematic Analysis of unstructured individual interviews conducted with participants, the results highlight a scripting of intimacy with/in anal fisting that is grounded on three recurrent and interrelated themes: trust and vulnerability; connection and communication; as well as pleasure and skill. The results of this study draw attention to the ways in which anal fisting is not only experienced as a deeply intimate form of pleasure and lovemaking for its participants, but, moreover, how the construction and understanding of intimacy in fist-fucking is framed as a queer/er mode of anal sex/uality and erotics that defines and constitutes itself in contradistinction to both hetero- and homo-normative scripts.