I have a friend that I suspect may share the same affinity towards women's clothing. His parents are friends of mine, and as hes grown up, he also became a friend.
His mom has pictures of him in a frilly dress when he was very young...she wanted a girl. When he was just at the end of trick-or-treat age, he and a friend came around at Halloween dressed as girls. Both wearing mini skirts, and looking really good...almost too good. He has recently had some meme's posted on social media about "being yourself". His hair is growing really long as well. His girlfriend is very fun-loving, and strikes me as the type that would have fun dressing him up.
I'm just not sure that I would want to ask him about it....it could offend him if I'm wrong, or worse, it could out me.
Has anyone else had a similar situation?