On Monday, my girlfriend was over, trying on the maid outfit she bought for an anime convention we are attending. I casually asked if I could try it on, she giggled, and said okay. I did and she said I looked very pretty. I then proceeded to tell her about my crossdressing desires, and she said, "Well, let's go pick you out an outfit, then!" We went online to the same shop she got her maid uniform from, and I proceeded to select an entire maid outfit, which I am wearing currently at the time of writing this.
I just wanted to say how amazing my girlfriend is. She encouraged me to shave my legs and arms, (though she likes me to keep the chest hair, which is a fair trade, I think), and we're already planning a lolita tea party, where we can both dress up! Next week, she's going to show me some tips and tricks with make-up, too! I'm already looking forward to my next outfit, which I think is going to be a pink lolita outfit.
So, yeah. That's my story, and I've never been happier!