This piece is written as an autoethnographic memoir and study of how it has been and is to live as an HIV-positive gay man from Aotearoa New Zealand across a time of great cultural change. It is a reflection through a sociological and historical lens of how the personal side of my life as a gay man intersects with wider cultural, political and health-related themes. Generational trauma impacted how gay men coming of age during the AIDS crisis engaged in sexual practices. The biomedical methods of HIV prevention, like pre-exposure prophylaxis (PrEP), have the potential to transform community practices, with profound psychological consequences. In this chapter, I present an account of Allan, a gay man in his sixties who lives in Aotearoa New Zealand and uses PrEP. During the AIDS crisis, Allan’s perception of physical closeness with other men became contaminated with fear of HIV transmission and feelings of mistrust, guilt and shame. With PrEP, these feelings disappeared as Allan recovered important functions of his sexual experience: transcending the boundaries of individuality and resisting heteronormative norms through subversive practices. The effects of PrEP can be viewed from a generational perspective to reveal the undoing of the psychological effects of the AIDS crisis trauma and the recovering of the pleasure of sexual connection by older gay men.