I just wanted to add that I do agree with others here in seeking help with a therapist.
It is important that you do find a therapist that is good at dealing with this specific difficulty. Not every therapist is good at every issue and it CAN take time to find the right therapist so know this up front and try very hard to make it a point to interview the therapist and see if the therapist will be a good match for you.

I mentioned the acting Not because you are handsome or that you should go into that field. I was trying to think of a place you could work on expressing emotions that is acceptable and even brought out and appreciated.

Often men DO like acting because it does give them freedom to explore emotions outside the realm of what is deemed acceptable in the social atmosphere. And even Comedy is often expressed and done by people who actually suffer in their real life and can somehow use comedy to offset it.

I can't say that it WILL help you, but it is something to consider trying along with therapy, a place you could perhaps work at expressing emotions that is acceptable.
I think as I mentioned that between you being so conditioned in your childhood along with what is expected socially, sure, you have a definite wall you have to break through.

Open Eyes