Sexual abuse of males is common. While a wide body of literature examines the behavioral, emotional, and social consequences associated with being sexually abused, comparatively few studies have focused on males. This study addresses this gap by examining the influence of family and peer context on long- term behavioral outcomes in a nationally representative, longitudinal, multi-informant sample of sexually abused boys 5 years after initial involvement in the child welfare system (N = 171). Cumulative family risk conferred greater risk for internalizing and externalizing problems over time while social skills had a buffering effect. Peer rejection had a more prominent role in influencing internalizing outcomes; however, this influence did not extend to externalizing problems. These findings lend support to the growing body of research underscoring the dynamic and complex relationship between behavioral problems across development. As prevention and intervention efforts for males are developed, it is critical to consider sexual abuse victimization and the multi-systemic risk and resilience processes.