This article begins with a male analysand’s report of heterosexual intercourse, which he experiences as intensely pleasurable and disturbing. The analysis of his account produces an initially confusing picture of male sexuality beyond the binaries of man/penetrator and woman/penetrated. In an attempt to situate this analysis in theoretical terms, the habitual male denial of the passive position in sexual intercourse and the emphasis on an actively penetrating phallic position are understood as a gendered defense formation against excessive sexual arousal. With recourse to Laplanche’s theory of the constitution of infantile sexuality as the translation of enigmatic parental messages, I argue that sex always retains the capacity to shatter rigid sexual stereotypes. Meltzer’s concept of the aesthetic conflict in encountering the maternal body is then used to account for the specific psychic difficulties heterosexual men face in sexual intercourse with women.