I'm a bit of a punk and will push not only mine, but others' comfort zones.
Most of the pushing was when I first started. I went FT the moment I went on HRT. Before that, I was already out to everyone and mostly full time (mostly, 'cause I didn't have much for clothing, but already had been introducing myself as myself). Then, 2 weeks into HRT I started a new job and went as myself.
I pushed myself a lot when I started (Jan 2006). I went out to the mall and got clothes. I went to the thrift store. I would try the clothes on in the store. I would wear make-up (which was pretty easy, 'cause I already had the goth look going). For about six months I was mostly androgynous but as the summer came along I went more on the female side. Then, summer came and HRT and FT came.
Other trans folk don't really like shopping with me, especially if they are just starting out. I've been known to drag someone into the MAC store and sit them down and get them to have a make-over right in the store. Also, for going into the store and getting them to actually try stuff on and buy stuff. I'm a lot more "jump right in" than a lot of people are comfortable with. And, I have no problems convincing someone to jump with me. Usually the result is good, but I will give that push to someone who is having troubles doing it themselves. At the same time, however, I'll respect it if someone isn't ready or is unsure. I don't make anyone do anything against their will -- but I'm good for giving that push if they need it (and that push, like any change, isn't usually comfortable at first... but feels great after you do it and know you can accomplish something).
Also, before I got my SRS I pulled a big stunt by getting a chelsea hair cut (buzzed in the back, long bangs in the front). I then went and did some drag king stuff, and actually preformed on stage. Not very common for a mtf to do that. I pushed a lot of buttons with people doing that. I don't do shows anymore, however. Last Halloween, although, I went out in male drag and it was fun. I have no interest in being male, however.
Of course, deciding to dress male a couple of times and do a drag show pushed a lot of the comfort zones around me in the mtf community... especially since it was a month before my SRS. It make people angry, while it inspired others to be themselves. The biggest lesson, of course, was that I don't fit in as male at all. LOL But, I wanted to push that envelope to make myself think and be sure that I was on the right direction; as well, I wanted to show people that you can be yourself, and no matter what you are wearing you'll always be who you are.
It was an interesting experiment, anyway. Last Halloween was interesting, too, cause it had been a year and a half since SRS and I haven't done any drag at all since the last time. I painted on a beard, did the clothing... I did pretty well. I then realized how hard it was to act male -- people spotted me as female fairly quickly and often I got, "cool costume!" remarks. LOL It was interesting.
I'll have to admit it was an odd feeling walking around on Halloween and then going to the mall and then theater with my friend (we have a tradition to watch Saw together every Halloween). Psychologically, it really confirmed that I'm a woman and couldn't be a man if I wanted to be... it would be fake.
