I think from personal experience the issue for boys may go a bit beyond just not wanting to abandon structures that benefit them. Lots of boys who feel strong internal pressure to transcend gender norms (many gay boys, for example, who for reasons we don’t fully understand often seem innately effeminate), experience intense social pressure and shaming when they actually do transcend norms.
Perhaps that’s something like boys and men as a group enforcing group privilege? To the point of privilege violators being punished?
In any case, I do enjoy reading about how your important partners display a mix of different gender characteristics. The most important men in my life have felt like that to me.
Lenny was a very large, strong man who could be hard charging and traditionally masculine. But he had a tender effeminate side as well that even displayed itself as campy sometimes. As we gay men can do.
My ex Army helicopter pilot Don is serious butch. Not a campy bone in his body. He builds log cabins and shoots rifles for fun. But he is the most emotionally sensitive, caring father and grandfather you would would ever meet. It’s the mix of the feminine and masculine that attracted me most strongly to him, I think.