This study examines the effects of orphanhood status on the timing of first sexual intercourse among youth in Malawi. Log-normal models were applied to survey data collected between May and August 2009 from 1,214 adolescents aged 12–18 in Mzuzu, Northern Malawi. Results of this study show that orphanhood is a significant predictor of age at first sex. Male double orphans experienced first sexual intercourse earlier than their male non-orphan peers. Similarly, female maternal and paternal orphans had their sexual debut faster than their non-orphan counterparts. The introduction of social support variables accounted for the orphanhood disadvantage. These findings suggest that in order to delay sexual initiation and reduce HIV risk among orphans in Malawi, policy efforts should focus on enhancing factual knowledge about HIV/AIDS, household food security, social support, and other measures that will strengthen existing social support networks and connectedness of surviving family members.