My uncle has been in prison since the late 80s. He's getting out in a couple of days, and I really want to have a relationship with him. My parents want me to as well. He is completely unaware of my trans status, and he'll probably be devastated if I tell him. His daughter died not long ago, and I think he was really looking forward to getting acquainted with his "niece." I was a three-year-old frilly (not by choice) little "girl" when he last saw me, so this is going to be quite a shock. That said, I do want to come out to him as male. The problem is that my parents don't want me to "do that to him." They don't understand why I can't just "be female" around him. I tried explaining that despite my body, I can't and don't know how to "be female," and situations where I am expected to do so make me suicidal. Well, now my mama thinks I'm "crazy," "dangerous" and "oppressing myself." So she wants to put me through reparative therapy instead of helping me transition. ("I don't want you to make your body male, I want you to make your brain female so I can have my daughter back. I want RACHEL! WHY can't I call you that?!?!) Everyone is telling me that if I come out to my uncle, it will destroy him and they'll never forgive me. So should I, or shouldn't I?

If you don't, it'll destroy you and you're going to break your family apart just by doing what they've asked.
Even if you somehow agreed to this, it will inevitably fail because of built up resentment towards them.

I tell this to everyone...if they love you, they'll get over it. It might take a while but they will get over it. I'm sure it will come as a shock to your uncle, but who knows, maybe prison has given him some time to reflect on life and what is truly important. As a result, he may be the most accepting of all.

I would be your true self and not the person they are trying to force you to be. When I came out, I was told one of my Uncle's was transphobic since someone else in the family had already transitioned. In the end, he was completely fine with it and wanted me to be happy. It's true he had his own way of rationalizing why it happened. The fact is by telling the truth to him it will be better for you and your family in the long run. Your health and well being is what is important here and not their comfort.

If prison didn't destroy him, I doubt you having changed will..?

You may find one of your biggest supporters in him, you won't know unless you try..?