Transgender Obsession

 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 me and the mirror 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 girl. The difference in my mind between a cross dresser and a transgender woman. 

Of course, my early obsession didn't turn out to be the last I would experience. In fact, I almost fell victim to another persons' obsession many years later. Which I will get to in a second. Before I do, I developed a real obsession with getting out in the world and seeing how well I presented myself as a woman. These were the years I was married to my second wife. Somehow we made it through twenty five years before she passed away. I kept making promises to her I would not go out in public unless I had a motel room to get ready in. So I wouldn't risk being seen leaving the house as my feminine self. Perhaps, as you may have figured out, I couldn't stick to the plan. Which led to lies and huge fights. The hardest part of the whole obsession was me being dishonest with her. I finally was able to grow a beard and forced myself to stop everything for the last eight months of her life.

As I promised, another's person's obsession almost harmed me one night at a party my wife and I went to. I will refer to him as a transgender "admirer". Or a man who has an obsession with being with a transgender woman or cross dresser sexually. This person towered over me and outweighed me too and on the night in question, I was wearing an ultra short mini dress. Highly disapproved by my wife. As it turned out he got me cornered in a narrow hallway where I couldn't escape. For the first time in my life I felt threatened and nearly helpless. About the time I didn't know what to do my wife appeared and defused the whole situation. After the evening was over she had some unkind words for me becoming someone else's obsession. 

I guess in many ways human obsession's are different critters. In some ways they drive us forward into new frontiers and in others they can endanger us. Crossing the gender border can provide us with many opportunities to explore wonderful new adventures. We just have to be careful when we do it.