I totally get what you're saying - I've not actually prettied myself up for quite awhile. I do it now and then as a nice thing to do, but mostly I stick to being pretty generic guy but then again, if i was physically a girl I wouldn't dress too different than what I am right now haha. I can fairly fluidly jump between either gender when needed, but I'm way more comfortable being my girl side online where as I feel I sorta go through the paces as a guy. I don't actually know if that is a unique thing or not, since I have talked and read stories from other transgendered people that had a difficult time understanding how the other side lives - its always been a weird second nature to me (not putting anyone down - I just think I may be more fluid than some people)
One thing I've wanted to do for a long time though is go to a transgendered boutique/salon place and get a full day transformation done with the makeup and maybe a wig and the filler cup bras and pads and all that. I actually went looking around for one, but couldn't find one in San Diego =(