There is concern that orphans may be at particular risk of HIV infection due to earlier age of sexual onset and higher likelihood of sexual exploitation or abuse; however, there is limited empirical evidence examining this phenomenon. Utilizing data from 1,694 Black South African youth aged 14–18, of whom 31% are classified as orphaned, this analysis explores the relationship between orphan status and sexual risk. The analysis found both male and female orphans significantly more likely to have engaged in sex as compared to non-orphans (49% vs. 39%). After adjusting for socio-demographic variables, orphans were nearly one and half times more likely than non-orphans to have had sex. Among sexually active youth, orphans reported younger age of sexual intercourse with 23% of orphans having had sex by age 13 or younger compared to 15% of non-orphans. Programmatic implications of these findings for the care and protection of orphans are discussed.