The current study looked at three related areas of research in the field of child psychopathy. It extends the findings of adult research investigating the link between sexual behavior and psychopathy to a sample of detained juveniles. It also examined the factor structure of youth psychopathy and sexual behavior as well as the Big Five personality domains that have been associated with these constructs. Participants completed self-report measures of psychopathy, personality, and sexual behavior. Results of the current study suggest that, as predicted, there is a relation between promiscuous sexual behavior and psychopathy. The results support promiscuity being a salient predictor of psychopathy for females but not for males. Exploratory factor analyses suggest that the original two-factor structure best captures the structure of psychopathy and sexual behavior in a group of youthful offenders. In both the two and three factor models, promiscuous sexual behavior loaded with the items that comprise the Callous-Unemotional factor on the APSD. Loading on the Callous-Unemotional factor was predicted in the current study and suggests that promiscuous sexual behavior is related to the personality features of psychopathy and not merely a behavioral outcome of psychopathy. Finally, results of the current study find that the Big Five personality profile of youth with psychopathic traits resembles that which has been demonstrated in adult samples: low agreeableness and low conscientiousness. Contrary to expectations, the Big Five profile of youth with psychopathic traits did not include high extraversion.