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The homosexual behavior of male inmates has been extensively studied; however, similar behaviors by female inmates, other than descriptions of the role of masculinity in prison settings, has been virtually ignored. Observations suggest that the incidence of both lesbianism and unusual masculinity among females may be higher in prisons and jails than in the general population. This study surveyed both heterosexual and homosexual female detainees to determine whether lesbian inmates, particularly those with a masculinized appearance, are more prone to violent or antisocial behavior, than heterosexual females without masculine features and, if so, whether this relationship is a function of biological conditions or sociological influences. Results indicated that lesbian detainees had more masculine traits, more feelings of hostility and anger, and experienced more physical child abuse than did heterosexual detainees. Although they did not report significantly more violent crimes, they were more often detained for longer periods of time. And while self-reported symptoms of Attention Deficit and Conduct Disorders were more prevalent in lesbian detainees, other conditions of biologic origin were not related to sexual preference. These findings suggest that lesbian detainees are treated more harshly by the criminal justice system and that further research is needed to sort out the various biological and social contributors to behavioral and attitudinal differences.