Given the potential for unintended pregnancy and exposure to sexually transmitted infections, both of which can have long-term deleterious health consequences, the identification of predictors of adolescent risky sexual behavior remains an important line of inquiry. Although prior research has identified a variety of family and individual factors that are associated with risky sexual behavior, few studies have examined the role of family economic stress. The current study utilized three waves of data from a community sample of African American families with adolescents (N = 778, 54% girls, average age = 10.4 years old at Wave 1, 12.3 years old at Wave 2, 15.6 years old at Wave 3) to test the family stress model as an explanation of adolescent risky sexual behavior. Multi-group analyses examined gender differences in the family processes expected to link economic stress and risky sexual behavior. Unlike most studies utilizing this theoretical perspective, family structure was also taken into account. The results supported the propositions of the family stress model for boys and girls for both two-caregiver and single-mother households. Further, in single-mother households, maternal psychological distress continued to have a positive effect on adolescent risky sex even after taking into account the impact of parenting behaviors. Overall, the results suggest that economic stress ripples through the family system, increasing adolescent risky sexual behavior through its negative impact on family processes, highlighting the need for systemic policy changes rather than individual-level intervention/prevention efforts.