Several scholars have lauded gender crossing as one pathway for tearing down hierarchies of gender and sexuality. Central but often under-examined in their discussions is understanding the skill and persistence of childhood gender nonconformists. In examining some of these skills, this article investigates their relationship to specific social situations or geographic locations and considers their psychological and corporeal aspects. These skills, asserts the author, may prove to have significant implications for a classroom aimed at combating oppression of gender and sexuality premised upon discretely defined genders. (Contains 11 notes.)