What does it mean when your boyfriend enjoys wearing women's clothing?

Answer:

"He would be a Transvestite, Transvestite is where the included party wears womens clothing while still remaining male in the genetalia department, Transsexual is where that said individual had been and had completed a sex change and does no longer have any male genetalia and has been left with a simulated vagina area, made by reconstructiong the male penis by slicing in half and a folded method inside the body to replicate the vaginal structure. in some cases males can remain non-gay and enjoy wearing womens clothing although this may be abnormal it does not essentially label the individual as gay, but most cases males would wear womens clothing to help release their feminine side which can be more dominant than the male hormones." Hope this helps
-Cheers

He could also just enjoy it? Maybe he wants to be a drag queen. To each his own.