Background: Early sex is associated with high-risk behaviors and outcomes, including sexual risk behaviors, forced sex, physical dating violence, and becoming pregnant or impregnating someone. Methods: Using 2005 and 2007 data from the New York City Youth Risk Behavior Survey (N = 17,220), this study examined the prevalence of early sex among public high school students; associations between early sex and other sexual risk factors and violence indicators; and whether associations varied across 4 racial/ethnic groups. Bivariate and multiple logistic regression models estimated the relationship between sexual risk and violence outcomes and "early sex," defined as first having sexual intercourse before age 14. Separate models with an interaction term for early sex by race/ethnicity were also estimated. Results: More than one third of students who ever had sex reported having early sex. Adolescents reporting early sex were significantly more likely than those reporting later sex to engage in most sexual risk behaviors and to experience violence. The magnitude of association varied significantly by race/ethnicity for sexual risk behaviors. Conclusions: The high prevalence of early sex, coupled with its associated high-risk behaviors and outcomes, underscores the necessity of implementing evidence-based interventions that have been found to positively impact these behaviors beginning in middle school. (Contains 3 tables and 1 figure.)