The Beginning – When and Why.

The “when” is a lot easier to answer than the “why”.  I’m quite sure most of us already know this, but here is my take on it.


I remember as a very young kid, laying on the floor, getting in the way of my mother as she vacuumed, so she had to step over me. As she did so, I would look up her skirt, I guess to see what every young boy was curious about, but that doesn’t ring quite true. I seemed to have a different reason, but at the time I had no clue really what it was.

One evening, I came down stairs dressed only in my pajama shirt, carrying my pants as there was a knot in the draw string and I couldn’t get them on. The shirt was long and my dad said “look, you’re wearing a dress”. I was very embarrassed and hid behind a chair waiting for my pants to be fixed. My dad told me I should have played it up, shown off my dress, pranced around a bit. Did this start me off? Was this a planting of a seed? I don’t think so.

The first dozen years of my life I grew up in England. As kids, my sister and I one Christmas had  received dress-up a police uniform and my sister a nurses (no gender bias there..haha). Around the age of 9 or 10, I remember wanting to try on her nurses uniform and being disappointed that it was too small. Why I wanted to, I have no idea. Somehow though, I got the idea of wearing the police jacket, found and put on a pair of my moms nylons and wrapped the black cape from the nurses uniform around my waist as a skirt. I guess this was the beginning of my love of uniforms. Anyway, I headed out into the house to “direct traffic”. The feel of the nylons was something else. I played for a few minuets then was noticed through the window by my parents, who were outside. They laughed some and waved at me and I shrunk back into the corner. If only I had known then what I know now.

A couple of days later, I was very disappointed to find that the nylons that I had thrown under my bed, when I had gotten changed out of my “police womans” uniform, were no longer there. My mom had found them and taken them back. The next year or two I don’t recall any real big dressing occurrences, maybe a few trips into my sister’s room to try on a few things, but at that time, her stuff was too small for me so I could only partially get into them. There was also the “obligatory” browse through my mothers closet, but her stuff was too big, at that time.

WHY….why oh why?

This is not something I ever remember being given an option to do or not to do. No body forced me to try on or to wear girls clothing. But, while being quite comfortable with myself being a boy, I always liked the look of girls clothing. What was the trigger that made me what to look like a police woman? The only occasion I remember seeing other boys wearing girlish clothes was at a theatrical production by a troupe of Boy Scouts (I was in Cubs at the time), a number of them were dressed as fairies, I thought that look interesting.

Although I may have taken the first step to expose Michelle to the world through my photos on my Flickr account, I have remained quiet on the chat side of things. I have, however, done a lot of online reading, taking in everybodys take on crossdressing and transgender issues. I have, as many have, sought the answer to “why do we do this?”

There are as many degrees of crossdressing as there are theories as to why we do it. From the wearing of just one article of women’s clothing under your male clothes, to the 100% passable guy “on femme”. From the married professional father who does it once in a while, to the guy who is making a living from it. I’m not sure if we should be categorizing the degree of crossdressing or should we be plotting a point on a 4 section X, Y, chart. Thoughts?

Besides the old school way of thinking, (crossdressing is a mental disorder, meds and electric shocks will cure that), the vast majority of explanations out there are that it is a stress reliever, or a backlash at the establishment (women can were mens cloths but not the other way round), or a sexual fetish and that a crossdresser will almost always experience a sexual desire before, during and after the event. Funny thing though……at 9 years old, I had no stress, didn’t really care about the establishment and had no idea what sex was, let alone an orgasum! So then, why did I start? Not for these reasons. I believe there is something deeper in our psychological makeup that pushes us to do this. It’s not always there, sometimes remaining dormant for months, but could just as easily surface and remain with use for days, requiring us to dress or suppress as the situation dictates.

So, WHEN has been answered. WHY……anybody? All I have is more questions. Why are there so many of us? Why the different levels of crossdressing? Why me? As I said before, I didn’t choose to be a crossdresser (I don’t not want to be one either, I enjoy it), just as much as someone chose to be gay, why would anybody choose to make their life difficult? Maybe it is in our genes.

Sorry if I get a bit rambling, hope to improve with practice. I would appreciate any like-minded thoughts to this baffling phenomena.


ps. its Christmas Eve as I finish this blog. Away from my kids and wife for the second time in three years. Here is hoping that everybody enjoys their time with family and friends at this time of year. Merry Christmas. M.


  1. Welcome to blogging world, search the answer to “why” question and publish it in your posting maybe it can help the others including me. Merry Christmas Thank you.

    • Thanks Lulu.
      I don’t know if there is an answer the question “why”, but I hope to have fun exploring other questions as they surface.

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