I'm still new to all this, but I wanted to share my experience in case there may be someone who could benefit (and maybe someone could give me a hand, too!)
I had a wonderful night on the town with my fiancee Friday night. I got dressed in a cute outfit, did my own makeup (this time more subtle, lighter eyeliner under they eye, etc, proud of my pretty "natural" look.)
We went to a performance of a local band in the tourist-friendly downtown area, enjoying just being girls out on the town. We kept getting attention, but not negative attention. It was all very flattering, including the expression we overheard from a group of guys who passed by about the beautiful ladies they had just seen (we were the only women in the area; a big ego-boost). I didn't get any hostile or puzzled stares going in to a local shop for coffee; I was (gasp) apparently unremarkable. This is *very* new to me; I think I may have *finally* gotten my walk down.
Quite simply, we were having a blast.
Then we went to a local gay bar I have visited infrequently for some time. As the night wore on, I realized I was getting clocked more and more. I half-expected *that*, the area being more open to transgendered people, etc... but what amazed me is people recognized me from before. Nothing hostile, but I found myself coming out again and again to people who had apparently missed the original bulletin... and then someone took my picture:

Aaaack! My face was suddenly splotchy, my eye makeup had disappeared, and all sense of being pretty flew out the window... I had been having such a great time up until then... I realize, now, it wasn't that bad a pic, but at the time I felt like I looked terrible, and I wanted to hide.
I did my best to relax, and then it hit me. It really didn't matter. I had been having a great time and others were enjoying my company. I was accepted, even if I *did* begin to resemble my "old self". It took a bit, and I found it very irritating when one person insisted on calling me by my old name, but all in all, I was OK. I went back to having a great evening.
I would, however, appreciate it if someone could help a girl out with a tip on how to make sure her makeup lasts all night...