Skirt Culture

When I first joked about running the Bolder Boulder in a SkirtSports pink Holiday Dress, I didn't realize stepping out the front door would give me such butterflies in my stomach. I'm used to causing a bit of a scene and getting noticed, but it took some serious balls to wear a dress in public.

As I jogged to the starting area with my roommate and a friend, all the nervous energy turned to contagious laughter. The smiles, laughs, pictures, pointing kids put a huge cheeky grin on my face.

With this race being more of a hard workout rather than a race, it was easy to relax and just laugh. How can you take yourself serious when you're cross dressing? Many of my friends took the time to remind me how much of a goober I am, and I loved it!

As the gun went off, I set out at a comfortable pace trying not to push to hard for the first mile. As I cruised along, I was quite surprised how comfortable the dress was. It didn't fly up or bunch at all. It just stayed right in place. As comfortable in my masculinity as I am, I must also say it felt incredibly smooth, soft, and breathable against my freshly shaven legs.

I think one of my favorite parts of the day was the looks on the guys' faces as I began to bring them back. I heard more than one grumble under the breath "oh man..." They seemed a bit disheartened to be passed by a guy in a pink dress with a pink mohawk while running 5:45 miles. I loved it! The more reactions I got, the more I feed off of it. Flashing guys drinking on their front porches, high five'n little kids, blowing kisses to photographers, hooting and hollering at the aid stations volunteers. It kept a huge smile on my face for the entire race.

I crossed the line in 36:30, after being out sprinted by a couple of guys who "weren't gonna be beat by a guy in a pink dress." It didn't matter to me. I ran a decent time, had tons of laughs and was apparently talked about on the radio and tv broadcasts later that day.

All and all it was the most fun Bolder Boulders I have every participated in (by far the silliest). If cross dressing was always this much fun and applauded, I might think of doing it more often, but for now I'll stick to causing a scene because of the funny little stripe of hair down the middle of my head.

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Will Kelsay is a Professional Xterra Triathlete and SkirtSports Shipper