I had my boobs measured last week and came in at a grand 30B! I don't need to wear a bra by any means but depending on outfit, I will. I can looks a little pear shaped so will sometime wear a bra to give myself a little lift/shape to try and balance things out.
I loathe seriously padded bras, a light t-shirt bra, fine but those ones with the gel inserts to make yourself 2 cup sizes bigger? He's only going to be disappointed when he takes it off.