Few scholars have examined psychopathology correlates of sex work. It has been suggested that sex work may reflect manifestations of impulsive-antisocial psychopathic traits (e.g., reckless disregard, delinquency) in women more than men. The current work examined relative contributions of drug dependence and distinct psychopathic features in relation to traditional forms of sex work (i.e., prostitution) in women, along with gender differences in psychopathy relationships with casual forms of sex exchange (i.e., trading sex for necessities). Study 1 included 171 community-dwelling women offenders, and Study 2 included 319 participants (42.3% women) with histories of drug use and/or violence. Participants completed the Psychopathy Checklist: Screening Version, prostitution was measured as self-report and/or public record data across studies, and sex exchange in Study 2 was assessed using a questionnaire based on prior research on sexual risk-taking. Findings across both studies demonstrated that although psychopathic traits, particularly impulsive-antisocial features, were associated with prostitution in women above the use of drugs, drug dependence did not moderate the relationship between psychopathic traits and prostitution in women. Analyses of Study 2 data revealed that impulsive-antisocial traits were associated with sex exchange at low, but not high, levels of interpersonal-affective traits across participants. As well, interpersonal-affective traits were significantly positively related to sex exchange in men and not significantly (and negatively) related in women. In sum, impulsive-antisocial traits related to prostitution among women, suggesting that women may manifest these traits within intimate contexts. Moreover, findings indicated gender differences in the manifestation of interpersonal-affective traits within sexual exchange contexts.