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

He could be a Transvestite. A transvestite is where a man wears women's clothing on occasion while still remaining male in the genitalia department and in his everyday social gender.

In many cases, males can remain heterosexual and enjoy wearing women's clothing. However, some narrow-minded people may still consider this abnormal. In most cases, males would wear women's clothing to help release their "feminine side" which can be more dominant than their "male side."

A transsexual is someone who needs or has sex reassignment surgery, though after surgery, they are no longer transsexual, but legally and socially female. After sex reassignment, such a person no longer has any male genitalia and has been left with a constructed vagina area, made by reconstructing the penis by slicing in half and a folded method inside the body to form the vaginal structure.

Then again, such a guy could also just enjoy it. Maybe he wants to be a drag queen, or it just makes him feel more comfortable. To each his own.
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