As a homely 52-yo female wannabe?
He will probably be only "dating" himself.
It should be in a mental asylum...not allowed to pervert children.
Back around 2004 I went to a reunion of members of a Y2K programming staff meeting. I remember seeing an older, ugly and rather heavy set woman in a red dress sitting in a chair in the corner most of the night. She kinda gave me the creeps and seemed really depressed. I didn’t remember her from work and figured she was someone’s wife.
The next week I was having lunch with a couple of people I still worked with that were at the party as well and one said, “did you see Joe?” I said no. They both then went into the details of the antics of Joe and his sex change operation. Yep. It was the “woman”.
He was always an odd duck, and the operation just made him a LOT odder. Pretty wig, though.