An ethnically diverse sample of 120 mostly gay-identified men who engaged in “bareback” intercourse was recruited via the Internet in New York City. By study design three quarters of participants were HIV-uninfected and engaged in condomless receptive anal intercourse. In the course of face-to-face in-depth interviews, participants were asked what led them to have their first bareback experience as well as to continue with the behavior. Qualitative analysis identified the pivotal role that sexual pleasure and intimacy have in this population and how drives for sexual satisfaction, adventure, intimacy, and love overpower health concerns and condom use recommendations. Men interested in bareback sex use a variety of defense mechanisms to account for, justify, and exonerate their behavior. HIV-prevention interventions have paid insufficient attention to libidinal drives, a crucial element of psychological functioning.