While the explicit rule requiring sexual involvement to be solely restricted to marital partners is owed to religious norms, contemporary society and culture also greatly control the sexual attitude of a person. Cumulatively, these could be viewed as issues that shape masculinity conceptions which have traditionally demanded that men should display sexual prowess and fearlessness. However, adolescent boys have scored below target goals of 95-95-95 goals of HIV testing, ART initiation, and viral load (VL) suppression, respectively, in the past years, with boys constituting more than 68% of AIDS-related deaths in areas such as Siaya County of Kenya during 2018–2021. Although lack of access to healthcare has been attributed to high costs of services and inept medical infrastructure, limited focus has been directed at the extent to which religion and societal-cultural demands of the Luo community in Western Kenya have shaped masculinities in VL suppression continuum. This chapter analyzes the role of social, religious, and cultural demands on young men’s sexuality and the implications that these demands pose for viral load suppression among boys on ART in Siaya County, Kenya. The chapter uses qualitative approaches to focus on field studies involving cohorts of adolescent boys aged 14–19 on ART, highlighting lived experiences of community health providers regarding how societal imperatives including culture and religion shape their sexual behavior in VL suppression endeavors. The majority of adolescent boys on ART are found to have continued to embrace social, religious, and cultural directions which lead them into engagement in multiple unprotected sexual relationships. This in turn renders efforts aimed at achieving HIV treatment and viral load suppression futile. Enhanced targeted masculinity behavior-change sensitization therefore remains critical.