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). The purpose of this study was to identify attributions for and responses to painful RAI among Black MSM in South African townships. In-depth interviews were conducted with 81 Black MSM (ages 20-39 years) who were purposively recruited from four townships. The semi-structured interviews addressed sexual behavior and identity, alcohol use, and safer sex. Pain during RAI was brought up by many participants without specific prompting from the interviewer. Analysis of the interview transcripts revealed that pain was a common feature of first RAI experiences but was not limited to first-time experiences. The participants attributed pain during RAI to partner characteristics, interpersonal dynamics, lack of lubricant, and alcohol use or non-use. The main strategies participants used to address pain during RAI were setting sexual boundaries and lubricant use; a small number of participants reported purposefully consuming alcohol to prevent the pain associated with RAI. Black South African MSM can be supported to reduce pain during RAI in ways that reduce their HIV/STI risk. Culturally specific sexual health education, supportive sexual health services, and improved access to condom-compatible lubricants are important components of HIV/STI interventions for this population.