[PerkyAcups]

I'm in a similar situation and about the same size boobs. I ordered a couple of bras and when the wife saw the charge on the card got upset. I explained that my boobs jiggle when I walk and I get self-conscious. Also getting pain from excessive movement of which she could relate.  It took her a couple weeks to warm up to the idea but after I  had her stand behind me and actually grope my boobs, she's finally on board. 
 I have to admit that I really enjoy wearing a bra!

yea, this has been a very slow process.  complaining about shirts rubbing on my nipples.  Finding shirts where my nipples don't show.  If she found one of my bras I don't think it would go as well.  I really needed it to be her idea.

Agreed! It should definitely be her idea.If you are willing to wait a few months, next Summer you could suggest that the vests are too hot to wear in the heath and get her to suggest sports bras (that are essentially shorter vests). 
If that goes through, make a few comments about how good the light padding feels when it protects you nipples further.

From there, the following Winter when you wear more layers, you could progress into t-shirts bras, which are lightly padded "actual" bras.

Take it easy. If you raise the bet too soon it could cost you everything.

thought I would give an update.  I have been wearing the tank tops my wife bought me most days for the last 8 months. Not much has really been said during that time. Few months ago I bought an under armour women's crop tank top.  It fit nice and snug. Not being as long it was more comfortable.  Folding laundry my wife held it up and said here is your girlfriend's shirt, its an XL and kind of frowned.  I told her I liked the brand and wanted to try it. Didn't realize it was so short, but I liked that it wasn't so hot.  I haven't worn it since.  

It is summer now and it is starting to get really hot.  The tank tops just aren't practical in the summer. I get so hot and uncomfortable.  I mentioned one day out working in yard how hot the tank tops are. She said maybe you shouldn't wear it while your working. I replied I wasn't comfortable without one on when I am with friends.  We are at youth baseball fields for tournaments all weekend through June.  I complain to her fairly often how hot I am getting in these tanks.  She hasn't said much in response so far. 

I am thinking about asking her if they make some sort of nipple covers I can wear on hot days.  I actually have a pair of silicone one, but I want her support. They hide my nipples well, but I think makes my breasts appear more round and doesn't offer any support.  But maybe this will open the door to the next option.