I too have been contacted off line about specifics mostly due to the embarrassment talking about bras and breasts bring on for men. I too am still guarded in what and how I say things even though it has taken a while for myself to talk more openly about my breasts and wearing bras.
As a friend of mine has pointed out, it isn't the bra that is the problem, it is the breast. People can't tell if you are wearing a bra, but they can tell if you have breasts whether you are in a bra or not. How will you deal with that?
Even though society is more allowing of things once considered taboo, those of us with unwanted gynecomastia are still discriminated against. "Real men don't have breasts or wear bras." In reality real men DO have breasts and DO wear bras for their developed chests. I didn't ask to have breasts. No one asked my opinion, but since I have them, how do I deal with them and everyone deals differently. I have decided that I will embrace them and celebrate them and take care of them as women do since they are a part of me whether I want them to be or not and surgery isn't an option. But I am more comfortable now physically as well as mentally since doing so even though it continues to be a struggle at times.
I am a male. I present male. A male is what I am. I have no desire to be a female. But due to hormones in my body that I have no control over, my body isn't completely male either. The testosterone and estrogen stay in a constant battle of how my body reacts and looks. It is physically more comfortable for me to wear a bra than to not wear a bra because I have a bust that needs supporting. Since wearing a bra, I don't think about my bust as much as I used to. Bottom line for me is comfort. The physical support of a well fitting bra provides that for me. But that can be in direct odds with male shirts. Women's tops fit my shape better and are more comfortable, particularly in the bust, albeit with a feminine appearance in the torso area, but I wear men's shirts and find ways to wear them without looking out of place as a man. It is hard, but can be done successfully, as many here have proven.
Yes, I would love to not have to worry about what my chest looks like in a shirt. I would love to just put on a bra and a light tee shirt like women do and go about my business with no one looking, but that isn't how it works. I hope one day it will and the only way it will is to be as open as you can and that isn't easy, no matter who you are. Not for me anyway.