So, I went to visit my oldest friend yesterday and, while I was there, told him that I've been crossdressing since I was a kid. We've been friends basically all our lives, since our moms were friends.
Since it was the first time we'd seen each other since the summer, I started out by asking him if he did anything for Halloween this year, and went on to say that I hadn't this year, but had I ever shown him the pictures from 2 years ago? (Which, of course, I hadn't...) That was the year I went to work as "The Lady in Red", using the old "lost a bet" line, and since I was going to "have to" wear a dress, I might as well go all the way. And it wasn't just any red dress, but a gorgeous, Lauren Ralph Lauren full-length evening gown, with a side-slit up past the knee. It cost way too much money, but when I saw it, I just had to have it.
He was surprised, but totally accepting. It didn't even really faze him when I said that I was wearing a bra, panties and pantyhose under my T-shirt and khakis, as I had been for some of our other get-togethers, and even to university (we independently chose the same program, at the same school!).
In the past, I'd thought of surprising him by dressing one day when he was coming over to my place, but I never did. Now that I've told him, and he seems cool with it, I'm more seriously considering it for next time...
Melissa