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Chapter 4: Dressing for Obedience

I had worn women's clothes. It was rudimentary and clumsy. Truly, crossdressing—not dressing like a woman, being a man wearing something that a lady might and even then, not well. The only research I did was to compare a size chart online so that I understood what a woman's shoe size was to a man's. I figured out what size to get so that the blouse and skirt I bought weren't too frumpy or too tight. The only easy parts were the stockings.

Straight up, I have always had a fetish for stockings. Even as an eighteen year old who hadn't come to terms with who I truly was, if I was going to jerk off, then stockings had to be involved. Either the person I was looking at was wearing them, the story talked about them or I had them on myself. When I pulled them on in my pathetic attempt to crossdress, that was the night I had the best orgasm of my life.

Despite looking like an idiot without makeup or anything special done to my hair or even much in the way of grooming, dressing up was what made me realize that there was more to dressing up than putting on clothes. Somewhere deep in my soul I felt right, even in the cheap department store crap that I picked up simply because it was cheap and fit. That's why I had such a powerful cum and that's why I knew that eventually, I had to do something about my gender.

...

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