I agree with bea. Blouses short skirts a wig. Pretty underwear.
As for as going out it's up to him. As far as the other things you talked about. Those are questions you have to ask him.
It's honestly a pretty common fetish for guys and doesn't mean he's gay or wants to you to wear a strap on. I do believe when they dress up most guys do pick a girl name to be called. He might not be comfortable with others seeing him because for some guys that have this fetish it's could be the same feeling as going out in public in lingerie.
I can't say how he feels but I have hung out in the fetish seen and it is always better to ask questions and be open to what he says so he doesn't have it. A lot of people do hide it from fear of how their partner might react. Also if he did want to do something that make you uncomfortable just say so.
Most people are OK with not doing certain things if they know it crosses a line with their partner. He would love you surprising him with a girly sexy outfit.
Its all up to him how far he wants to take his cross dressing. Ask him if he would like to go shopping with you. And he can go as a guy and still try on clothes Go to YouTube.com and search for "How to look like a girlie girl".
, search also for how to's on cross dressing, clothing etc.
I cant really gove you an answer,but what I can give you is a way to a solution, that is you have to find the anglde that you relate to or peaks your interest. A good paper is one that people get drawn into because it reaches them ln some way.As for me WW11 to me, I think of the holocaust and the effect it had on the survivors, their families and those who stood by and did nothing until it was too late.