Knowledge about sexual practices and life experiences of men having sex with men in Kenya, and indeed in East Africa, is limited. Although the impact of male same-sex HIV transmission in Africa is increasingly acknowledged, HIV prevention initiatives remain focused largely on heterosexual and mother-to-child transmission. Using data from ten in-depth interviews and three focus group discussions (36 men), this analysis explores social and behavioural determinants of sexual risks among men who sell sex to men in Mombasa, Kenya. Analysis showed a range and variation of men by age and social class. First male same-sex experiences occurred for diverse reasons, including love and pleasure, as part of sexual exploration, economic exchange and coercion. Condom use is erratic and subject to common constraints, including notions of sexual interference and motivations of clients. Low knowledge compounds sexual risk taking, with a widespread belief that the risk of HIV transmission through anal sex is lower than vaginal sex. Traditional family values, stereotypes of abnormality, gender norms and cultural and religious influences underlie intense stigma and discrimination. This information is guiding development of peer education programmes and sensitisation of health providers, addressing unmet HIV prevention needs. Such changes are required throughout Eastern Africa.