On the outside I maintain a persona of being very male. At home and in private I feel free to express myself as a cross dresser. I have thought of having a more feminine outward appearance, but I'm not there yet. Even considered female hormone treatments and other treatments so to appear more like I envision myself as someone that falls under the category of the 'T' in GLBT community.
I think more dialog with your son may help you understand his interest in change of gender appearance.
I have known males that remain heterosexual, keep their genitalia and have transformed into women with facial surgery and hormones as far as looks go, yet they still act like guys in many ways.