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I had a group of friends in college, including a hardcore sjw. I didn't like her, but I didn't want to cause infighting so I played nice. She dropped out because she got pregnant, but I still vaguely kept up contact because we had the same friends.

Fast forward to two months ago and I'm having lunch with most of our group and our significant others. SJW friend complains about being busy with the last month of school (she's a secretary for a high school) and not having a babysitter for her daughter. My wife is generous to a fault and offered to watch her. She just had our daughter, so work was off the table. SJW is either desperate or likes my wife so she agrees.

My wife starts sitting almost daily after that. My friend's daughter is nice and cute, so I was happy with her being around. Nothing out of the ordinary happened until this weekend. She was sleeping over that weekend and I went to go check on her. She was already in her PJs with a MLP shirt. I was thing to be fatherly I guess, and asked"Is that the show girls your age are watching?" She shook her head and said "I don't know, I'm not a girl."

I thought she was just being weird at first so I asked her what she meant, and she patted her pants. I just gave her a confused look and she might have pulled down her pants enough for me to see his dick. I was really fucking confused but I scolded him for showing me. It didn't bug me to see it, but I wouldn't want my kids flashing adults. He told me his mom made him dress up like a girl because she disliked guys, including him I guess. I don't really get my friend, but the kid was casual and said he gets punished for telling people the truth.

I told my wife about it and she was weirded out too, but neither of us know if we should avoid the issue or help him deal with it. I haven't told anyone else because I'm unsure of how people would react. I haven't dealt with crazy chicks before, so I'm pretty stumped.