Yes, the berdache tradition falls nicely into what you're hinting at here. Also, Tiresius, who was both a man and a woman, in ancient Greek mythology. Do you know of the Stanford biologist Joan Roughgarden, who writes on sexual selection? Formerly a man. Also, the great travel writer Jan Morris, formerly James Morris, is a wonderful example of this. Check out Conundrum, her recounting of the transition from man to woman. A truly wonderful book.