They say everyone remembers their first time, and I have a lot of firsts to remember.

But the one I want to tell you about is my first time getting it on with a woman while I was wearing ladies’ clothing. While I’m definitely what you’d call sexually experienced, I’d never shared my frilly fetish with anyone else, and I’d certainly never had sex while dressed up as a woman. But when I started dating Holly, I knew I wanted to let her in on my secret.

We’d been dating for a few months when I decided that I had to tell her about my desire to wear women’s clothing. She came over for dinner at my place, and after our meal, I slipped away to change while she put together the dessert she’d brought for us. I wasn’t sure how she’d react to my surprise, but... Read More