Well, Spacey already said some of the things I wanted to say, but I have more to add x3
A therapist is still important because he/she will help you sort out your issues in your moment of weakness. Also, if you decide to transition, therapists are important for verification as well as for, most importantly of all, being there for when you actually transition.
Ignoring all social stigmas that are/aren't around as much as they seem to be, or that your body will be stressed with rematuring itself, transitioning functions as a huge workload to the mind. The process of going from male into female definately will be smoother if you can have some support.
--Be careful about being with men. It's a nasty entanglement. Online relationships ARE relationships, after all.
--If you don't want to face family rejection, try to sensitize and educate them. It's hard to say what's appropriate to say and when, but a lot of TS agroing comes out of confusion and fear. Fear that someone is messed up, that they screwed up, or something like that, and confusion because it is such an unnatural thing for a "cisgender" to not be very cis.
--Career-wise, look into colleges. Do it immediately. D: Don't put it off! D: You don't -HAVE- to immediately dig into colleges and stuff, you just need to do your research and understand what it's about. Also look at federal financial aid, because there's grants and stuff that will make financial hardships a lot less of hardships when it comes to college.
As for the guy to let you stay, I would strongly discourage twirling men around your fingers. :\ It's disrespectful, and stirs vengeance. The WORST situation you can be in, is to put someone you're playing with in a lot of power to strike you down over doing it. ---A situation like that gets real ugly real quick, and I say it more out of my concern of safety than my sense of morals when I say you should dismiss staying with men for free as options. (Not to mention, that you're talking about doing this after mentioning you're meeting these men as a woman, despite lack of transition. If you suddenly come to them and they see a guy when they expected a woman, that can get downright dangerous.)