Protective and risk factors associated with rates of early sexual debut and risky sexual behaviors for a sample of low-income adolescent boys were examined using bioecological theory framed by a resiliency perspective. Protective processes examined include a close mother-son and father-son relationship, parental monitoring and family routines, as well as the adolescent boy's academic achievement, expectations, and school recognition. The risk factors assessed were delinquent behaviors, if the adolescent was born to a teenage mother, family structure, monthly family income, risky neighborhood environments, family of origin welfare receipt, and maternal education. Waves one (1999) and two (2001) of "Welfare, Children, and Families: A Three-City Study" were used (N=528; Wave 1 ages 10-14 years). Associations between early sexual debut and risky sexual behaviors with individual, family, school, and neighborhood protective and risk factors were addressed through a series of d-probit and Ordinary Least Squares multiple regression techniques. When protective and risk factors were addressed independently, academic achievement and parental monitoring protected adolescent boys from early sexual debut and risky sexual behaviors while drug and alcohol use and school problems placed them at risk for these behaviors. However, when the model is assessed together, early parental monitoring and academic achievement were shown to protect boys' early sexual debut and risky sexual behaviors by reducing their delinquent behaviors, specifically early drug and alcohol use and school problems.