I can imagine the way you must feel about yourself. I have wife who also has big problems with her body. It sometimes causes all sorts of problems at home. Please believe us when we say you look good. We mean it and a crossdresser will know the difference I can tell you!
He will be feeling scared as well. Embarrased and guilty all at the same time. he will need reassurance as much as you do. If you work together and talk about it anything is possible. Take it slow and maybe buy him something femanine. It doesn't have to be clothes to make it count. It's surprising how much the little things work, certainly for me. Just recognition helps a lot.
Yes there are different levels as with everything. becarefull you don't push him further than he is ready to go or you may find the situation reversed. He'll think your'e a bit odd!
I hope it all works out. It sounds like he his a very lucky guy!