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Justice-involved adolescents are particularly vulnerable to engaging in risky sex and developing substance use disorders. Given these negative sequelae, identifying risk factors that place these adolescents at increased risk and potentially influence changes over time is important. Data from 347 justice-involved male adolescents was used for the current study. Participants completed baseline assessments of adverse childhood experiences, impulsivity, sociosexuality, substance use histories, and sexual histories, as well as 3, 6, 9, and 12-month assessments of sexual risk taking and alcohol/marijuana problems. Structural equational modeling (SEM) was used to examine the influence of impulsivity, adverse childhood experiences, and desirability of first sexual encounter on sexual risk taking and substance use at baseline assessment. More adverse childhood experiences and higher impulsivity were associated with higher levels of substance use; and greater desirability of first sexual encounter and higher impulsivity were associated with more sexual risk taking. A parallel process latent growth model was also estimated to examine longitudinal relationships among risky sex and alcohol/marijuana problems, and impulsivity, sociosexuality, adverse childhood experiences, and desirability. Results revealed that more adverse childhood experiences, higher levels of sociosexuality, and higher impulsivity were associated with more alcohol and marijuana problems at 3-month assessment. Desirability was not associated with either risky sex or alcohol/marijuana problems across time. An association was found between impulsivity and the linear slope of alcohol/marijuana problems, suggesting that extreme levels of impulsivity may account for a significantly slower increase in substance problems over time. Implications for future research and interventions for this vulnerable population are discussed.