Understand that even in approaching him this way (which is fantastic!) there's a good chance he will still want to hide.

Men are pushed VERY hard to keep this aspect of them hidden. My wife is quite accepting, but even I find myself hiding at times. Just this morning...I was ironing some clothes in the laundry room, wearing a pair of heels. My wife woke up, and came downstairs. I had about 10 seconds notice. ZIP I ran to put the heels away and back to ironing before she came in the room.

WHY do I do this when I know she is accepting? It's very hard, and something I struggle with.

You'll probably face the same problems. Hang in there. It's a hard road for him too.

Oh, and have him dress up as much as he ever does before having him "No, I want to see you the whole nine yards. Then I'll peal it off piece by piece!"