I'd like to think that transgender individuals like me help the cause. I myself am genderfluid so "going from one box to the other" really won't help me much since my identity isn't static. If anything, my desire to present consistently with my internal gender is much the same as your desire to wear pretty, feminine things. On my feminine days, I want to act like and be received as a woman. To that end, I dress the part. Some days (very rarely) I work up the courage to go out into public and brave the criticism and ostracism. To the random stranger in the street, I am a crossdresser, cause I'm a guy dressed like a girl.
As for my friends (we're in our 20's like you) most have been accepting and supportive. It's a stretch to say our entire generation is more supportive as a whole, but many of us are.
As for your original question, you said it yourself: we have to be the change we wish to see in the world. And to do that, we have to venture out into that world. I myself am not ready to go out and about full time, and I admire those of us who do.
