My First Dress

Do you remember the first time you dressed as a girl? Jennifer Wilson, now a 55 years old London solicitor, looks back on her halcyon days at school:

Public school in the 1950’s was aimed at toughening up the “mummy’s little darlings” to become the leaders of tomorrow. It was a regime of stark dormitories, cold baths, early morning runs, corporal punishments, and supposedly for pleasure, boxing and rugby.

A friend of mine, Charles, is one of the most convincing cross dressers I have ever seen. When dressed as Charlene, he transforms himself from a good looking black guy into a ravishing, slender woman, with dusky looks and a curvy figure.

For me, all this was terrifying. I was a small, red headed kid in glasses who wasn’t cut out for physical activity like many of the other boys. My mother thought I was ‘artistic’, but my father looked on me as too sissy. Public school he believed would be the making of me. And so it was, but not in the way he thought!

I was a transvestite even before I went to the school in that I would dream of being dressed up, and would occasionally try on my mother’s petticoats during furtive sessions in the bathroom. But I never thought I would ever get the chance of acting like a girl. Thanks to the school, I did.

It was in the summer of 1953, which is perhaps why I remember the actual date so well. The Queen had taken the throne, Hilary had taken Everest, and I had taken the lead role in the school play – as Alice in Wonderland.

Looking back it seems a strange choice for a boy’s school, but the music master had written songs to go with it so perhaps it was all about indulging his little fantasy. I’m sure nobody knew it was also indulging mine.

I was 14 at the time, but my voice hadn’t broken and I was lead boy soprano in the school choir. I was small, as I say, and I suppose was the obvious choice to play Alice, but I still couldn’t believe my luck when I was asked, and really I still can’t. Not only being allowed to dress as a girl, but forced to, isn’t that every transvestite’s dream? It was certainly mine, and, I have to confess, still is.

I can even now remember the fast beating of my heart at the very first rehearsal. I was still in normal clothes of course, but it was the thrill of being dressed as Alice. As the weeks went on, it got curiouser and curiouser. I had to write to my mother and ask her if she would be willing to provide my costume. The school secretary gave me the list of clothing I would require, which I included with the letter after reading it over and over again – white headband, white pinafore, candy striped dress, white petticoat and long white socks. I could wear my plimsoll shoes, and the school would provide me with a long blonde wig.alicesdress

My mother treated all as a bit of a joke, but I think my father was furious with the school about it. When I went home for half-term, and my unforgettable first fitting, he just stayed out of the way.

We had two dress rehearsals before the real thing, and each time I was helped into my frock and pinafore I felt a tremendous exciting surge run through me.

But it was only on the night when itself when I also got to wear the wig and the stage lipstick, eyeliner and rouge that I got the most amazing experience of my life.

I cannot really describe my feelings of stepping onto the stage in front of all those people as Alice. How proud I felt of myself as I skipped and sang, laughed and cried, a girl for all to see. And how sad I was when I took my final curtsey to the polite clapping, blissfully aware that the audience hadn’t enjoyed it anywhere near as much as I had! Afterwards the cast was treated to tea with their parents, with chocolate cake we never saw any other time of the school year, iced buns and ginger beer. But the best bit for me that we were still in costume; Tweedle Dum and Tweedle Dee, with their cushions up their jumpers; the dormouse and the white rabbit with whiskers on their cheeks: and me, in the starched pinafore and sweet little dress my mother had made specially for me.



My Mother was terribly sweet about it, but I think she was worried inside about my enthusiasm. The play was over, but I was still acting as Alice. I didn’t want to stop being the little girl.

Eventually I had to go and get changed, and then a feeling of great embarrassment came over me. I knew I had pushed it too far, I had let down my guard, and the pangs of guilt stayed with me throughout the summer holidays

I never got the chance to do it again. My voice broke soon after and my days in the choir were gone. I don’t know if my father had said something to the school or not, but for some reason I was never chosen to play a girl again. I was in two other plays and a pageant, but each time I had to play male parts while other boys, who didn’t appreciate it, were forced into skirts. God, how I envied them!

Unfortunately I also couldn’t ever be Alice again. I tried in a roundabout way, to find out what happened to my costume but I think my Mother threw it away. I remember being invited to a fancy dress party the following year and suggesting, in a joking manner, about going as Alice. My mother just ignored it.

“Why don’t you go as a cowboy”, she said, and I did.

The End

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