Track Ban
A Vignette
By Maryanne Peters

If you really know your horses, on track betting is the way to win. People who treat horseracing as a game of chance are fools. Why not toss a coin? That is chance and probability, but if you know horses and courses and watch the animals and their riders and the track close up and in the flesh, then it is not a gamble, it is the exercise of special skills.

The problem was that I had been banned from the track for the biggest season of races for the year. I could recount why in detail. But suffice to say that I am guilty of winning too much too often, which the organizing jockey clubs don’t like.
“A day at the Races” by Llongstaff

I had bought the lady’s race day outfit for my mother. It was a little matronly or old fashioned, but it included the hat and the bag, and it had cost good money, so I didn’t dispose of it even after she had to go into care and became indefinitely unable to attend and. I was rummaging through the back closet for an idea for a disguise when I happened upon it. It did get me wondering if I could pull off the ultimate masquerade but I pushed the idea away for an hour or two, until I realized that I had no other workable options.

I decided to make some enquiries of one of those feminization boutiques to see whether there was any chance of me being able to do this. The owner of the establishment, a woman (or I think she was a woman) called Odette, was very helpful.

“We really do this so that our clients can see themselves as women, but some make very convincing women and can function in society … it is just a question of place,” she said. “We always say that you can present as female to a point, and beyond that it is better to disclose that you are a transwoman. If you are not impersonating somebody and if you are in an environment accepting of diversity, then I don’t think you will have a problem. But as I say, only some can do it. We won’t know that until we have you dressed and we take you out in public to test your feminine behavior. Are you ready to do that?”

Like I said, there seemed to be no other way. It had to be me, and I couldn’t be the man who was banned, so I had to be the woman who wasn’t.

It was Odette who suggested that I use my own hair. It was long and quite thick. She said that it could be styled for body, but I couldn’t work out why I wouldn’t just wear a wig.

“Because if you can’t take it off it will make it all seem more real,” she said. “The most important thing about looking like a woman and acting like a woman is believing that you can be a woman. I also recommend a total shave down even if you are wearing clothes that cover most of you. The feeling of it will help you be her. I even suggest that you take some female hormones – they won’t have any substantial effect but they will make you feel differently.”

I decided that I would follow her advice, all of it. She also had useful tips about how I should carry myself, not just as a woman but as a lady – the kind of lady that might attend a horse race meeting on her own and want to get up close to the action.

She was right – I needed a background story. I decided to pretend to be a lady from England with a background in breeding horses, but perhaps equestrian ponies rather than thoroughbreds. I needed to work on a voice – English, educated, and high enough to be a woman of that type. I had only a short time to do it, but I had a solid fund of cash to play with, and “the form” for this meeting was starting to look interesting. The horses expected to win might not be right for the course. There was the potential to make good money.

But could I pass as a woman? Certainly, Odette did a great job with the makeup, even insisting on some hair removal to make sure that nothing emerged though it during the day. The hair looked great under the hat, and the dress and chunky heeled boots were great too. But I knew that I had passed the test when I was approached by Terry Killeen who was one of the course committee that had banned me, or the man I had been.

“You seem to be doing very well, so I thought that I should introduce myself,” he said.

“I am Penelope Dashington,” I said. “But call me Penny.” Perhaps I should have walked away but I seemed to be doing so well that I was ready to take him on for a while. There were more races on the card and he could be useful. “Is there any chance of getting down to the stables to have a closer look? I breed horses you see, but not for jockey racing, More for show jumping, cross country and polo.” He seemed impressed by my English accent.

There was not a single race that I did not win a bundle on, but I held some tickets back to cash in later. I did not want to seem to have made as much as I had. But even without everything I had earned being revealed, it was enough to impress Terry.

“Would you like to join me for dinner tonight?” he asked me. He wanted to learn more about me. It was the last thing that I wanted. So why did I say yes? It was like a moth being attracted to the flame that was sure to burn me, but I was flying, and I was loving life in the air. It was not just Terry but there were others who were looking at me and admiring me. I did look good, and in acting the part, I felt good too. I felt slightly superior, and in charge, and yet fragile and even a little emotional. It was a heady mixture.

“Can I see you again,” Terry said at the end the evening. It was a very nice meal, and a great bottle of wine, and he paid. “Would you allow me to kiss you?”

I offered him my hand for him to kiss. After appearing a little puzzled he smiled and took it and planted a kiss.

“Maybe next time I can offer a little more,” I said.

After all, I didn’t have anything more to offer him … then. Now it is a very different situation. But Terry is not the only man out there who desires me, as I have discovered.

With all of this, it just seemed foolish to even consider going back to who I was. He was a tawdry gambler who lived life in the shadows with his form book and betting forms, whereas I am a lady, who understands horses, stallions, mares and geldings.

The End
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© Maryanne Peters 2026

Author's Note: Another short piece inspired by an AI image. Thanks to Eric for the edit and correcting me on horse racing nomenclature.