The current study examined 14 waves of data derived from a large, community-based study of the sexual behavior of impoverished youth between 12 and 17 years of age residing in the Deep South. We used multilevel linear modeling to identify ecological predictors of intercourse frequency and number of sexual partners among gender-specific subsamples. Results indicated that predictors of adolescent sexual behavior differed by both type of sexual behavior and gender. For males, age, maternal warmth, parental knowledge, curfew, self-worth, and sense of community predicted intercourse frequency, while age, parental knowledge, curfew, self-worth, friend support, and sense of community were significantly associated with having multiple sexual partners. Among females, age, curfew, and self-worth exerted significant effects on intercourse frequency, while age, parental knowledge, curfew, and self-worth exerted significant effects on having multiple sexual partners. Implications and future directions are discussed.