Everyone sees how loyal Wesley is too Fisk and how loyal the men are to Wesley and Fisk, not just the bribed officers and workers, but personal security. So how about Wilson meeting a Wesley who doesn't feel like a woman, feels like a James, feels like a man deep inside no matter what his body is on the outside. Wilson, may not understand or maybe he does in some way, but he helps and stands by Wesley as he transitions, supports and protects him, gives him a friend with nothing expected in return.

Wesley is grateful, he hasn't had anyone believe in him or his image until Wilson and he loves the man for it, would give everything for the man, even watch him tear down a city to remake it and help him do it, because Wilson Fisk has vision, he sees what everyone doesn't, he saw James, stuck in her body.

+1 if author works in how Wesley extends the same hand that Wilson gave to him to the other transgender people and helps them in anyway he can because he doesn't want them to go through the anguish he did and they become unfalteringly loyal to Wesley and by extension Wilson for what they offered them, acceptance, help, support, etc.

+1,000,000 points to author if they can work in run-ins with Daredevil in costume or out with Wesley or some of the other transitioning or in transition people that work for Fisk.