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Long before I ever heard of, or knew there was such a thing as cross-dressing fiction I was writing it. Probably before I even heard of such a thing as “cross-dressing”. I don’t know how it got started but I remember it was something I would routinely do at night as a child if I couldn’t sleep.

I’d make up stories about how, through a chain of unavoidable circumstances, I would wind up dressed as a girl. They were silly and absurd but not really any worse than some of the stories I’ve seen published on-line. Being cold was a common excuse for needing to put on women’s clothing. Years later I would see a similar scenario played out by Chevy Chase in the movie “Christmas Vacation”. In the movie Chevy, as Clark Griswold, gets locked in his attic as the family goes out shopping. As it gets increasingly colder he is compelled to put on women’s clothing items he finds in a storage trunk in order to keep warm. By the end he is wearing long pink gloves, a green hat and a mink stole. Of course, in my stories, fate had much better taste.

Sometimes my boy clothes would become destroyed somehow or I’d get locked out of my house for some reason. Most of the details of the stories I have forgotten but there is one I remember in which I am shopping with my Mom and sisters and I get bored, find a chair and fall asleep. They forget about me or think I went home with friends and I get locked in the department store. Either I spill something on my clothes or the heat goes out and I am forced to wear women’s clothing. For some reason I never find the t-shirts and sweat pants. I guess this store only sold lacey dresses and high heeled shoes. I still think it would be fun to spend the night in a store and have all of the styles at my disposal without having to be self-conscious.

As the stories evolved, I would find myself in situations that included my appearing completely as a woman including hair and makeup. Maybe, I was undercover or forced to present as a female to survive. Again, the ideas were replayed to me in pop-culture. Bosom Buddies and Tootsie were the best known of the gender swap movies and tv shows that were popular in the late 70’s and early 80’s.

Another theme was being forced by another person to cross-dress. At first it might have been my mom who makes me put on my sister’s dress so that she could hem it. Or a babysitter who preferred to babysit girls and would make me into one. Later it might have been a girlfriend who cajoled me into wearing her clothes and makeup. Sometimes in the stories I might even be blackmailed into looking like a female by some bad people.

In some stories I would somehow become transformed physically into a female. The transformation might be the work of some mad scientist whose house I happened upon after my car broke down; a magical potion that I stumbled upon thinking I had found the Fountain of Youth; a curse for wronging a sorcerer; etc.

It was hard to find realistic excuses for having to appear female but I would keep trying, tweeking the stories to be as plausible as possible. Most of the fiction stories I’ve read on-line have holes in the logic as well. Many of them seem to result in some kind of “romantic” experience with a man. That never happened in my stories but as the stories became more developed there would be some kind of task or outing that I needed to partake in. As a girl I might be required to go to a prom, walk down a crowded street, or take my sister’s place as a cheerleader.

Maybe in some way I am now trying to live out some of those fantasy fiction stories. I still think about things I can wear and things I can do enfemm when I can’t sleep. I don’t think it ever resulted in falling asleep faster but insomnia is much more fun.

Fantasy/Fiction Stories

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