I have resisted this for many years now, but i finally had enough.
I was working on remodeling a house and sweating like a beast. Everyday I was suffering with sore nipples from the sweaty t-shirts making them hard all day. The final straw that broke the camels back...I hooked a nipple on a shower door when I was painting a bathroom. That was immensely painful for the rest of the day.
When I got home, I took a shower, and I grabbed one of my wife's bras, and it actually fit pretty good. I walked down stairs, and said "can you tell I am wearing this?" Then I lifted my shirt. Told her how miserable I was (actually she was there when I snagged my nipple on the shower door) and this seemed to help immediately.
She just said it actually made my breasts less obvious, less pointy, and she understood. She didnt react the way I feared. She suggested I get my own though. The one I grabbed she didnt like...probably too big of band which is why it fit me, so she gave it to me. My wife has very large breasts, so her normal bras wont fit me anyway. The sleeper one I tried on isnt a perfect fit, but it was a relief from the pain.
I thought I was a 42C, so I ordered one. It was too small. I ordered a few more 44C and 44D from amazon.
Measuring is kind of a crap shoot. Band is 42-43, but over breast across nipples is nearly 51. I have a lot of sumo underarm fat/boob, and a bit of a V shape to my back. Getting it right is kind of a guessing game. Amazon is my friend, as I can try one and return until i get it right. I am way to embarrassed for a formal fitting, and suspect they will sell me a $90 bra and not a $25 one.
I still can't bring myself to wear one in public, but I will probably get there eventually. Baby steps...I guess. I still feel like I look stupid when I see myself in the mirror. All man, except for the stupid boobs and bra. I am not a small skinny guy, or in anyway androgynous. I am also not ready to get cut on just so other people are okay with how i look.
Acceptance is a process. One I have resisted probably with too much effort over the years. It is all a head game.