As someone who had noticeable pubescent gynecomastia, who suffered through the "ritual" of breast growth in my teens, and no where to turn for help or understanding, who was groped by boys and teased and touched by girls, who, together, helped shatter all body image and self image of myself for decades, bras were an off again, on again kind of thing. In my late teens and early twenties, it was not unheard of that I would pilfer a bra here or there from a female friend or sister or mother of a male friend to try. In retrospect, to have had even a training bra that fit would have been of some benefit even though I suspect in my teen years I topped out around a B cup. Had I been born a girl, at that stage, my parents would have had me strapped in a bra so fast, it would have made my head spin. As was pointed out on numerous occasions at the time by others, I was as large if not larger than some girls my age. In general the bras I took were either too large or too small and never really fit but gave me the idea of what being supported could be and feel like. It didn't feel girly or sissy or feminine. It felt natural. It felt right. It felt good. They also hid my nipples, which seem to be a dead give away for me. It was years later before I gained enough courage to get my first properly fitted bra.
It would have been nice to have had some understanding adults, but it was a time when things like that didn't happen. In those days, girls had boobs, guys didn't. Period. Full stop. Life wouldn't have been easy in a bra in those days, but I think it would have given me a better outlook on myself and my body. Due to my bosom, I stopped participating in sports, because not only of the teasing, but of the physical discomfort on my chest. Had I known better, even a regular soft cup bra would have been better than having them swing and sway freely. But again, there was no one, peers or adults I felt I could turn to. So, like many here, I suffered in silence, questioning what was I?
So now I wear a bra for comfort, and to some extent, appearance due to ptosis (saggy boobs). I have tried to take a more positive attitude towards my body and now dress according to what it demands. I still present male, I dress for comfort, not fetish or sexual. And with sizeable breasts (I am wearing 36DDD/F 38DD), men's shirts don't always work. Not only in fit, but comfort as well. Yes, dressing is more tricky and takes a little longer these days, but I am a happier person, because I have learned to love me and not hate my bosom. I actively deal with what I have, not wish to what I don't have. It's taken a lifetime to get to this point in life.