The results of research linking age and sexual risk among men who have sex with men have been inconsistent. This study assessed the relationship between age and sexual risk among 193 Black men who have sex with men in Pretoria. Older men who have sex with men reported engaging in more frequent unprotected insertive anal intercourse. We examined whether components of Information–Motivation–Behavioral Skills model mediated this relationship. Results showed that (1) older age predicts less positive attitudes toward condoms, (2) less positive attitudes predict more frequent unprotected insertive anal intercourse, and (3) attitudes mediate the relationship between age and frequency of unprotected insertive anal intercourse. We consider two possible explanations for these findings: a developmental trajectory and a cohort effect.