Hmm. I feel very insecure about my maleness right now because I'm early in transition and have always been pretty insecure. That, and my...anatomical shortcomings. But I don't worry so much about what other people might expect from me because of my maleness. There are many different kinds of men, and I'm my own kind of man.
I'm pretty sensitive and empathetic in certain ways, and I don't see these traits as hurdles to get over or as impediments to be eliminated. Heck, my therapist is cisgender, and he's gentle and caring. He's managed to live on this planet for at least sixty years now, so it can be done.
I think that for me, it's not so much what kind of man I am but being accepted as any kind of man. A lot of people, if they knew about my past, would not consider me a "real" man. So that's where my anxiety lies.
We all choose what kind of person we are. To some extent we are hindered by society and family dynamics, but we do get to shape ourselves. Just make sure you shape yourself in ways that are comfortable for you; don't simply cater to everyone else. I mean, we do adopt some characteristics in order to fit in and survive, but don't go all uber-male just for that reason. Find a self you can live with.
And it's a slow process, acclimating and evolving. You'll get there. It just takes time.