There's cases all over history of "women" who led their lives as men, dressing in male clothing etc. ... some at great risk, others were known and "accepted" as much as could be in the society that they lived in. I'm sure there's an equal amount of "men" who led their lives as women. There's an interesting book on just the topic of gender reversals in society from an anthropological perspective: Gender Reversals and Gender Cultures: Anthropological and Historical Perspectives. I think Third Sex, Third Gender: Beyond Sexual Dimorphism in Culture and History also kind of deals with this type of gender-bending through history.