Once as a teenager I dressed up and then put on my Jason Voorhess hockey mask. It was definitely a surreal feeling and I liked the feeling because I finally felt like I was looking at a female in the mirror. ( at the time I wore no makeup and didn't shave my face )

I can definitely understand why a person would choose to wear any type of mask. I'm not sure if they experience the feeling I had when I put on that mask many years ago if not I imagine it may be similar