All of this reminds me a lot of my 26-year-old self. That was a long time ago now. If I could go back and talk to my 26-year-old self, I would absolutely encourage him to accept this side of himself and explore these fantasies safely. I always hoped my sex and romance lives would just fall into place, whether the fantasies disappeared or not. I was naive.
The Fortress is a safe place. Just be clear about your experience and interests during the booking process.
I've only been able to serve a Fortress Mistress once because I'm not lucky enough to get to NYC very often. I can wholeheartedly recommend Mistress Jane Li for the kind of treatment you're seeking. I don't think you could possibly go wrong there either.