[arl234]

Oh, wow! If I were you, I would find an opening to test her reaction by half-jokingly, saying something to her, like "You know, it might kinda cool to have some big titties". "What do you think? Would I look good with some B-cups?" "Would it turn you on if I had big boobs and wore a sexy bra for you?" You get the idea. It sounds like she is trying to help you hide your boobs but it also sounds like she might enjoy you wearing a bra, too. I like where tis is going. Good luck.

oh yea, I know what you mean.  Great idea. I am going to take it slow. I think if I complain a couple more times about my nipples being itchy exercising she will buy me a sports bra. That would be such a huge step.  Then see if I can slide in some comments about what if they were bigger.

If you keep making it like you are ashamed of it then she will probably be a lot more cautious about recommending anything.  You are really just hurting yourself.  Think about it, if you were doing something to her and it visibly made her uncomfortable to be the point where she would freeze (using your words) then would you even try to go further with whatever that may be?

Just try one of her bras, a mesh one probably put it on and tell her that for some reason you enjoy how it feels and that you like the feeling of your boobs being cupped by the bra.  If you give her the opening then she might take it but if you just keep diminishing it and getting quiet then she will not pursue it further.  It is what it is.  Just my two cents.