Pain during RAI was brought up by many participants without specific prompting from the interviewer. The semi-structured interviews addressed sexual behavior and identity, alcohol use, and safer sex. In-depth interviews were conducted with 81 Black MSM (ages 20–39 years) who were purposively recruited from four townships. The purpose of this study was to identify attributions for and responses to painful RAI among Black MSM in South African townships. Little is known about painful receptive anal intercourse (RAI) and its relationship to HIV risk and protective behaviors among men who have sex with men (MSM).