So, yesterday evening, I was preparing to go to a munch that I was organizing (for those who didn't see my other thread, munches are informal get-togethers at restaurants for BDSM enthusiasts). I attend most munches en femme (in "vanilla", ordinary girl clothes, not BDSM fetish attire), and yesterday was no exception. So I was in my apartment, fully dressed with my makeup and wig, and decided that before my ride came, it would be good to stop by the ATM near my grocery store (just a couple minutes' walk) and grab some cash. Well, on the way down, I saw on the sidewalk across from me two other graduate students whom I know quite well (we are all teaching assistants who work together in the same department). I recognized them, but I don't think that they saw me or recognized me, partially because I quickly (but not too obviously) turned in the other direction and walked off to the side so that my face would not be in view. At that part I was not far at all from my apartment building, and those two graduate students do know where I live, so if my "disguise" had been just a bit worse, they may have recognized me. There is, of course, the chance that they did recognize me and just didn't say anything, but I doubt it. I saw one of those students today (I was in guy mode today) and we had a conversation, and she didn't mention seeing me or hint that she saw me. So she either didn't see me or she is just being very tactful.
Now, I am friendly with these people and neither of them seem to be homophobic (or transphobic) people at all, but I just don't yet feel like I want to be "out" to them. I do, however, feel that I will inevitably be out to a fair amount of people, though. I live in a medium-sized town and I don't have a vehicle or a driver's license, so I walk or take the bus everywhere I go, unless someone is giving me a ride to/from a specific place. Going to neighboring towns just for the sake of avoiding people I know is not an option; I have to deal with the possibility of running into people unless I want to stay in hiding (which I really don't want). I have run into students as well, and said hello to one of them while I was en femme (she was not a student in my section, but was taking the subject that I teach, so we know each other).
It's an exhilarating experience, and part of me really wants to be out and open about it, but I want to take it slow.