The First Time Out
I’d decided I needed to do it. Not think about it, not plan it forever, not wait until I felt ready — just go.
Navy midi skirt, black tights, block heels, a white training top and a bomber jacket. I’d found a coffee shop in a village not far from where I lived that opened early on Sundays. Quiet. Low risk. That was the plan.
I showered at the gym after training and changed there. Which means, technically, I came out in a gym before I came out anywhere else. I hadn’t thought about that until just now. I walked through the gym and out of the door in a skirt and heels. Nobody said a word.
I drove over to meet a friend who knew exactly what I’d be wearing. She was already sitting at a table when I arrived.
I was nervous but holding it together — until my heels hit the wooden floor. That sound. That beautiful, sharp, unmistakable click. The owner — a guy in his mid-forties — and the young girl behind the coffee bar both looked over. I was about 6’5” in those heels. I’m not easy to miss on a normal day. In a skirt and heels on a quiet Sunday morning, I was impossible to miss.
But I held it together. Made it to the table. Sat down. Took off my jacket because I was sweating. And then — slowly — everything went back to normal. They served us coffee. We talked. We stayed until we needed to leave, and then we left. That was it, really.
The skirt fitted beautifully. My bra stayed where it needed to stay. I just looked like a guy in a skirt with heels. That was everything and nothing.
I was sad to take off the outfit before I got home. But I’m very proud I did it. Finally.
