Anal sex between men has been constructed in many ways throughout the last century. In this paper, I describe three realms of discourse that have offered ideas regarding the meanings and motivations of anal sex: (1) Freud's exploration of anal erotism using classical psychoanalytic language, (2) a radical sex theorist describing transcendence and community through anal sexuality, and (3) a Lacanian perspective that questions the idea of the anus as passive. Recurrent themes regarding power dynamics, identity and gender are identified and explored, and the role of anal sex as cultural signifier is examined.