I think that underworks is a good place to start. For a smaller chested and lighter weight guy I'd go with the tritop (I forget the model number), but for those with a little extra padding, or a larger chest the double front 997 is probably the way to go. You could always buy the 997 and suggest that if it rolls up then they could cut the bottom off to make it tritop length, as a lighter and smaller chested guy I had to do this because the rolling up drove me insane, but I've heard it staying down better on those heavier than me.
I'd not worry about offending him, I was too ashamed to ask my partner at the time to ask to get my first binder sent to their house and put on their card. Eventually I cracked and had to ask them -- amidst tears -- if I could. Then they refused to accept any money for it 😛