This is a touchy subject for sure as every parent will have different views and different ways of talking to their kids about such things. My oldest son was exactly like this boy...he was obsessed with being a girl from the time he was 2 until he was about 9. I never allowed him to leave the house dressed as a girl, but he explored plenty at home. I personally felt that he was too young to make such a monumental decision in his life and I knew that he would suffer terrible teasing at school if he were to dress as a girl. He is now almost 18 and so far has not come out as being gay or transgendered...thou gh we continue to give him ample opportunity to and express that whatever he is is okay with us. He is a fine young man with lots of friends (mostly girls by the way) and will be starting university in the fall. It is a very tricky thing supporting a child's feelings and wants and balancing with the harsh reality of the world.