This person is a PREDATOR. From what you write, it’s obvious to me that he has always been that way, despite your seeing him as “harmless” throughout your life. He MEANT for you to see him as harmless: that was always his goal. It’s what child groomers do. They deliberately act in caring, trustworthy ways in order to get both children and adults to trust them and let down their natural defensive instincts.

Transition is his last-ditch, desperate act to get closer to girls and/or young women. He thinks that since society condones and supports male to female transgenders, and guilt-trips women who express discomfort and fear of them, he can much more easily get away with preying on young women.

And you know what: HE’S RIGHT. If you keep allowing him into your life, including shopping trips to get underwear, he will do something bad to you and/or your family members, though he looks like he’s targeting you. And there won’t be much you can do about it, especially in a trans-friendly environment where his word will carry a lot more weight than yours, IF the authorities will even believe you!

So here’s my advice and I really hope you take it: GET AWAY FROM HIM. Cut of ALL communication and interactions. Don’t explain why or talk to him. If other people question you, just say you’re uncomfortable and change the subject/close the conversation. You DON’T owe anyone apologies and/or explanations.

HE’S A PREDATOR. YOU ARE HIS PREY. Get away from him. And DOCUMENT every single thing he says or does that makes you uncomfortable. I can’t emphasize this enough.