Gender-related aspects of self-perception were explored for 24 anatomical males consisting of three matched groups of transsexuals, heterosexuals, and homosexuals. MacKenzie's Diagnostic Criteria Scale ratings were used to confirm group membership. Instruments used were the Repertory Grid Technique, the Rosenberg Self-Esteem Scale, Bem Self Role Inventory, Maferr Inventory of Masculine Values, and Derogatis Sexual Functioning Inventory. Results for transsexual subjects reflected lowest self-esteem. Of the three groups, they perceived themselves to be the most like females and the most unlike other males. Transsexual subjects tended to describe themselves in nonmasculine terms and valued their gender role orientation. Homosexual subjects, on the other hand, reported the highest self-esteem. Additionally, they saw themselves as the most similar to males and the most dissimilar to females. As a group, homosexual subjects described themselves in comparatively strong masculine-stereotyped fashion and valued this posture. However, they believed that women do not value the self-orientation which these subjects endorsed for themselves. Heterosexual subjects scored moderately high in terms of global self-esteem. They described themselves as somewhat masculine to androgynous and reported valuing their gender role orientation. Results on the Repertory Grid and the Derogatis Sexual Functioning Inventory showed heterosexual subjects to be the least polarized in their gender-related self-descriptions. This group generally appeared to be least concerned with traditional gender role referents. The importance of a cognitive approach to clinical assessment of the transsexual individual is stressed.