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All of this is easy for Kellycan to say because she's so passable and pretty. :D (sorry, when someone tells me not to say something- most of the time I have to)
Seriously, though, when I dress a lot of times, I don't think I look "passable" because I see too much of my "normal" self in the mirror. My wife and I were out shopping for new outfits for me and I was all about "I don't want to show too much arm" (feeling self-conscious about size and tone and looking too "masculine" although realistically I'm not built that big). Then I saw some GG's on tv who were built similar to my stature and I've seen some t-girls on other sites that are built the same, so my mind has changed.
Essentially what I'm saying is that sometimes we look at ourselves and see something completely different than what everyone else sees. Either way, you have to be yourself and be comfortable with who you are. There are a lot of ways, not just with crossdressing, that I'm still learning and working on being completely comfortable with myself. I'm 36 years old and still learning those lessons.