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Over the years, I have encountered several different obsessions. The first of which was when I was very young and was exploring my strong need to wear feminine clothing. The more I snuck around and did it, the more I wanted to do. I have written in depth about saving my small allowance as well the money I made from a newspaper route so I could purchase my own make up and a few other items I could afford. The thrill of being able to buy my own pair of women’s shoes which fit still is a vibrant memory.
Photo Credit JJ Hart
From there, I developed a complete obsession with looking like a girl. I tried every second I could to be by myself to cross dress. I even found a hollowed out tree to hide a dress and panty hose in the woods next to our house so I could be alone with my obsession. I felt practice makes perfect so I thought I was progressing fairly well in the makeup department. Of course it was only the mirror and I doing the judging so winning the judging wasn’t so difficult. We lived in a semi rural area so my range of friends was very limited. Surprisingly though, I did find one acquaintance whose Mom let him dress in her clothes and makeup but he ended up moving several states away before I could communicate my desire to participate in the cross dressing with him.
The only thing I was having a difficult time learning was why the feelings I had after I participated in my obsession didn’t last. It was years later when I finally figured out I wanted more than the pretty clothes and makeup. I wanted to actually be a…
