He could be a slave to parents due to financial constraints, it's hard being independent these days. I'm in the same situation as you, feeling like I needed to please everyone but the fact is this is basically shooting yourself in the foot. Since I live in NYC, we have this place called Callen-Lorde where they offer sliding scales for those, like me, who are eligible for tit and are uninsured. Is there a special LGBT center where you live that can provide low-cost transgender care and help you start transitioning? You do have to remember that you owe it to yourself to be happy and stop pleasing others because you will not satisfy everyone. That is unrealistic. Do you also have a job?