I haven't really been able to dress up a lot (that's probably gonna change when I move out, oh for sure!) but the times I did, it was...well...
First time was scary. I mean, I just felt that I should try it, 'cause I've always wanted to...and I did, and it felt very good! There was some arousal, aye, but it didn't last too long. I was very emotionally excited, though, but I didn't get to enjoy it to my fullest, since I had to stay away from windows so the neighbours wouldn't catch a glance. So I only wore them for an hour (I borrowed my mother's

)
Second time...uhm, well, I had become part of this little theatre club, mostly improvised theatre and you get to play a lot of weird roles then

Anyway, we were having a special Impro-evening where we slept over at the theatre, and some of us got the idea that we should go dress ourselves up and stroll around the town. It was close to 11, I'd say. So I pick this -obviously- female coat, get the other girls to help me with the wig (long black hair, yes please!) and put on a hat and I was ready to go! I dare say, apart from the Pirate, I was the most feminine-looking of the bunch. Well, helped a bit that two were dressed as Pigeons, one as a hippie, one as a sleeper...and then the pirate, who was...well, pirates are sexy per definition, so yeah. Anyway, I had so much confidence walking there, laughing for real and having a good time. No arousal here, either. I just felt a part of them and it felt all natural.
I had some episodes during the lower grades of school as well, and I really did notice how I got more confidence when I could escape some of my shackles.
Nowadays, when I stay up late, I put on a skirt and just...well, sit back down at the computer. The hair on my legs ruins the feeling, but it doesn't feel weird to do it.
~Moi