I’d had it in mind to tell my wife that I was a crossdresser for several months before I actually said the words. By the time I did I’d shown a more gentle side of myself on numerous occasions and in many ways.
I was already taking her for regular shared nail appointments and had a wardrobe of increasingly androgynous clothing. It can hardly have been a surprise when one day I said I was going to start wearing a kilt to the office now and then. There was a drama series showing at the time that she enjoyed. When a brightly colored kilt arrived from Amazon one day I put it on, and her first words were, “Oh god, you look like that guy in that show.”
“Hey, big boy, where’s your sword?”
I looked a little nonplussed.
“I don’t think I have a …. Oh, I see where you’re going with this.”
I didn’t expect the kilt to have quite that effect. The first day I wore it to the office I got a combination of admiring glances, and one or two interesting comments. By day three it was accepted and normal. Admittedly I wanted to wear heels and panties with it, but that wasn’t on the cards yet.
Before long my dress sense was being complimented, and my kilt was both ‘so very masculine’ and also considered daring. I loved it. As for my wife, she was in highland heaven every time I wandered in with it on.
It suppose it had been three months since I’d made the decision to start adopting these changes, before I eventually spoke a word to my wife about it. I’d been wearing the kilt every now and then for at least a month before I broached the subject. I decided that when I did so it would have to be somewhat obliquely. I like being married. I have children. I’ve been divorced before and it’s no fun.
This would have to be done carefully.