[Ninja]

I was sitting in my chair and the wife walked by and grabbed my right boob and said that's quit a hand full and smiled, said they may get as big as  mine. I thought to myself that would be great she  is a 38 D

[PerkyAcups]

Last night we had a few drinks around the neighbors firepit.  When we got home I took my smoke smelled shirt off.  While I was standing in living room talking, she reaches over and pinches each nipple a few times then smiles and says you need your tank top. 
I responded ‘I wore it today under my baseball coach practice jersey’
She asked, ‘how was it?’
I said ‘it worked really well and reminded her bad those thin white practice shirts are.
She said, good glad they worked. 
She giggled and said, ‘who would have ever thought I would be buying you girls tops.’ Then she said something like ‘oh well it is what it is’ or something like that. I can’t remember exactly. But it sounded validating
I replied ‘I noticed I held my shoulders straighter and felt more confident’
 She said that's odd.
I replied I realized I had been pulling shoulders in to hide my chest. 
She responded that makes senses.   Then she kissed me and said she was glad she could help and the other 5 are in the mail.
 
I feel like that was great conversation.  It was casual and lighthearted. We both giggled about it.  Needless to say, I will be wearing my tank top again today and loving it.

[PerkyAcups]

I was sitting in my chair and the wife walked by and grabbed my right boob and said that's quit a hand full and smiled, said they may get as big as  mine. I thought to myself that would be great she  is a 38 D

 I love it when they do things like that.

[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.

I think you are exactly right.  I am going to keep wearing these tank tops. Keep having these conversations when the moments present themselves.  The tank tops are hot to wear. Next summer I will make that point and see how it goes. I agree 100%, if I go too fast it will get weird and go away. I am in a great spot now if I work it right.

[PerkyAcups]

Last night my wife playfully reached over and gave my left breast a squeeze. She kind of had a surprised look on her face but didn't say anything. She proceeded to do it a few more times during the evening. While she never said anything about it we ended up getting intimate in bed last night. During our intimacy she squeezed and nibbled on both of my breasts. Im calling it a win!

I love it when the wife plays with my nipples. She hasn't quite grabbed my breast and made a comment yet, but i hope we are getting closer.

[Ninja]

She is aware I have gynecomastia,, but is not aware I have been trying to make my boobs bigger by pumping in private. I hope to get bigger boobs- the way she acts I think she would be very accepting. Nipples are so sensitive would love to have her play and suck them