This paper examines the relationship between circumcision status and timing of sexual debut among unmarried youth in Sub-Saharan Africa using Demographic and Health Surveys. Results from survival analysis indicate that the association between circumcision and timing of first sex is place and context specific. Compared to uncircumcised, circumcised men in Rwanda, Uganda and Namibia hasten sexual initiation, whilst circumcised youth in Ethiopia and Mali delayed sex initiation. In Togo however, we found parity in timing to sexual debut. Our multivariate results reveal that, knowledge of HIV/AIDS risk and educational level also feed into the association between circumcision and timing of sex initiation- implying that efforts to prevent new HIV infection through circumcision could benefit from a proper understanding of how diverse set of factors interact in specific contexts to shape youth’s decisions to initiate early sex.