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. Sexual pain has been studied mainly in the context of heterosexual vaginal sex, and as a consequence, there has been limited study of painful anal intercourse in either women or men ( Sandfort & de Keizer, 2001 Štulhofer & Ajduković, 2011). Despite some empirical studies of painful sex experiences in samples of men who have sex with men (MSM) in North America and Europe, and some attention within HIV research among MSM in Africa, our understanding of pain during anal intercourse remains limited, particularly in relation to HIV risk and protective behaviors among MSM. This study presents findings from qualitative research with Black MSM in South Africa their experiences of and attributions for painful receptive anal intercourse (RAI) are discussed, as are their responses to RAI in terms of HIV risk and protective behaviors. Pain can occur during anal penetration when the external anal sphincter is not relaxed because the anus does not self-lubricate, lubricating substances are also needed to reduce pain from friction ( Hollows, 2007).