The aim of this study is to contribute to the understanding of motivations for cross-generational relationships and how the perception of risk of acquiring sexually transmitted infections (STIs) including HIV affects condom use in Kenya. Eight focus-group discussions were conducted with women and 28 interviews were held with men in four Kenyan towns. Ethnograph 5.0 computer software was used for the analysis of data. Women's primary incentive for engaging in such relationships is financial; men seek sexual gratification. Pressure from peers compels women to find older partners. Although some peers encourage such relationships, other groups, especially wives, same-aged boyfriends, and parents, disapprove of them. Couples are preoccupied by the threat of discovery. STI/HIV risk perception is low, and couples rarely use condoms. Material gain, sexual gratification, emotional factors, and recognition from peers override concern for STI/ HIV risk. Women's ability to negotiate condom use is compromised by age and economic disparities. Programmatic strategies include communicating information about such relationships' STI/HIV risk, promoting consistent condom use, decreasing peer pressure to pursue such relationships, and improving women's access to alternative sources of income.