Does girlfriend count?
I have always been self conscious about my breasts. I would pretty much always keep a t shirt at least on.
My GF would make sometimes comment about my breasts, man boobs, needing to wear a bra, etc. Teasing, but not awful. I felt uncomfortable with it, however.
My chest was quite hairy, and while I looked chesty, I would not say feminine.
Sometimes, I would get upper back pains, and at times, she would notice, and then seriously say a bra would help. Just say it businesslike: she can relate being a D cup. I always said a bra is too feminine.
Finally, she bought me a white Genie cami in XL and said this looks like a tank, but with support. I reluctantly tried it and she said it looked like it worked for me. My back did feel better, but it looked like a bra on top, with padded bra cups, even. I did not want it, even though it helped my back.
She said Ok, I will get you something to try that has nothing on your chest then. She got me a nude Spanx open bust cami in XL and said it does not come in white.
I put it on, and she asked how does that work for you. I said I could immediately feel how much it helped my back and that I liked how it was open with no bra in the chest. She said you like it and will wear it then? Because it is not cheap, and if you are not going to wear it, I will return.
She said because it is open in front, it is called WYOB style, wear your own bra; With a funny, little smile she said, you sure you don't want me to measure you for a bra? I figured she couldn't resist one little tease and I said no, I am sure. This is perfect just like this.
She said she would cut off the tags and I could just put my top back on and wear all day then. And I did under a heavy sweat shirt.
From time to time during the day, she would say, how is your back feeling? Quite good! Is the cami still comfortable? Very! She said you really like it, don't you? I said a lot! You look like you lost weight. Thank you. You posture looks better. I owe it to you.
No teasing at all, just consideration and compliments. She was clearly pleased by my enthusiasm and appreciation.
It was a positive, reaffirming experience.