This essay is an inaugural effort to conceive of homosexual boyhood. It focuses in particular on a subset of homosexual boys, parodically called “girlyboys,” whose mixed feminine-masculine gender experience moves beyond the conventional categories of masculinity and femininity. These boys have often been cast from the realm of “gender health” through the reluctance of psychologists and psychiatrists to recognize the actuality of gender variance and crossgendered identifications within the domain of mental health. Propelling and commingling with efforts to capture the subjectivity of girlyboys (largely through clinical material) is a discussion of the need for integration in human life. A call is made to retain concepts such as psychic structure and ego integration, and apply them to reimagine psychic developments that are free from the determinisms that psychoanalysts have so readily fallen back upon to account for human development.