@brainiac: Your dad sounds a lot like mine. If they really are alike, chances are he's going to internalize everything. If you want it to work, you have to make sure to communicate everything to him and make sure he understands everything the best he can. If possible, make sure he has someone other than you to talk to about it.
I wish I had explained everything better to my dad...I thought I did, but he was actually in the dark about my transition, and still is, and now our relationship has kind of hit a wall. I failed to realize it was just as hard for him as it is for me until it was too late, and now we can't talk about it at all. We're both really suffering from it.
That's all I can really think to say for now...Good luck.