Alexandra’s Thoughts On Crossdressing

I started crossdressing in 1978 or 1979, when I was around 10 years old. I tried on a pair of my cousin’s opaque black tights. She is a year younger than me, and, interestingly enough because I made the ironic connection years later, her name is Alexandra. It fascinates me to wonder why I tried on those tights in the first place. It wasn’t because I wanted to be a girl. It was probably a proxy for sexual exploration. Needless to say, it gave me a thrill. Perhaps because the act was done in secret and had an element of danger about it, I felt a buzz. In that act, I had ventured into a strange and wondrous place. My life would never be the same. In many ways, I suppose, Alex began to stir on that day four decades ago.

Throughout my teen years, I would secretly try on various clothes belonging to my mother since she was the only female around (I rarely saw my cousin, and when I did there was no opportunity to try on her stuff). I never had the chance to dress “full up,” only parts at a time and I did not have access to a wig. My mom also wore very little makeup and her wardrobe was boring, especially for a European woman in the 1980s.

One day, I think it was in 1985 or so, my stash was found. I was deeply ashamed and humiliated, and I can only imagine what my parents thought. All I remember is they were not pleased, and I received the silent treatment for a long time. I shudder when I think of that time. It was the worst moment of my life; which is to say I have a good life because if that’s the worst of it thus far I should consider myself fortunate.

I eventually resumed dressing, of course, but it was very sporadic. In 1987, I found myself alone in the house for a few hours, so I dressed as “full up” as I could, which means everything but a wig. I tried to style my longish hair, and I wore my mom’s yellow dress. Wow! I felt awesome! And that was it. A few months later I left for the military. I never dressed up as Alexandra while in the military.

As the years ticked by, the seed that would become Alex grew a bit. Girlfriends came and went, college came and went, and jobs would come and go as I moved along in my career. In 2005, I lost about 40 pounds due to food poisoning. What a nightmare! On the other hand, the result meant I could wear a size 8 or even a size 6! So, in 2006, after I moved to a new location, I decided to go “full up.” I went all out and purchased all manner of girly goodness. I spent perhaps $1,000 online (thank goodness for the Internet). I bought several wigs, as I had not done that before and had no idea what would look good. I also bought breast forms. The combination of wigs and breast forms, for me the quintessential elements of femininity at the time, was almost too much for my heart to handle. I dressed up in some kind of skirt suit, because as my friends already know I have a penchant for the corporate look.

With clothes and makeup on, I put on my first wig. I was a redhead for the first time, kind of shoulder length with a slight wave. I thought I looked hot. So, I looked at myself in the mirror and wandered about the apartment. I practiced walking around in heels. The swishing sound created by my nyloned legs rubbing against each other was divine. I could even detect a slight bounce in my silicone bosoms. But then, I got bored. A bored crossdresser is a dangerous crossdresser. I decided to go for a drive, and thankfully I had an attached garage at the time, meaning the chances of being exposed to neighbors was low. What a thrill! I could not believe what I was doing.

But the red hair didn’t feel right. I felt “off” somehow. I tried on the other wigs until I settled on a sort of wavy bob. And there she was. Alex was born. Except at the time, I had no name for this startling new creature in my life. That would come later.

I realized I had a digital camera, and that with a tripod I could take photos of myself in an effort to evaluate my appearance and manner. At first, the photos were disappointing. I looked really idiotic. But the photos served their purpose because I now had references to help polish my look. Finally, I took a series of successful photos with me wearing a pink outfit (the first photo in my Flickr stream, for example). I was very happy. I didn’t look idiotic any more. I looked like a girl. Now, as far as walking and talking, forget about it!

I went online to see if other people did similar things, and to find out more. I was worried I had a mental illness and my initial search revealed all manner of horrid fetishy crap that didn’t help. Finally, I found several crossdressers who really knew what they were doing. They were elegantly dressed, and their makeup and hair were perfect. At this point, a competitive quality to the crossdressing emerged, and the idea that this thing I did was a hobby or craft became real. Whereas as a kid I dressed for sexual reasons, now I dressed for artistic pleasure. It was challenging and creative and fun and fascinating. All the things an artist likes to play with.

By going online, I discovered Yahoo and Flickr. The first folks I found were Laura Lenley, Cristy Garcia, KC Tyler, and Steph Yeats. There were others, of course, but I remember those four in particular, and they are my friends to this day. I recall being so impressed and intimidated by them, but they were gracious and kind to me. I was so happy to have found such people. I wanted to reach out to them for advice and acceptance. In order to do so, I needed a name so I could get an account and email address. Andrea Michelle Forbes came out of my head rather quickly (Andrea was my first girlfriend in high school). I later changed my name to Alex, since I’ve always liked that name.

Later in 2006, I even went to the Southern Comfort Conference down the street from my home (imagine the fortune). It was during that conference that I decided to go out in public for the first time (not counting buzzing around in my getaway car earlier in the year). Damn, that was exhilarating! I sat in my car in the hotel parking lot for 45 minutes before mustering the courage to get out and walk through the hotel to the conference rooms. I remember being slightly panicked because once in the hotel I didn’t see any obvious signage or directions for SCC. I kept walking, and found the signs pointing to the escalators. On the way down, I looked down at my gray skirt, smooth legs, gray pumps, and the grating of the escalator step. What a happy, unreal day that was!

In the years since, I’ve polished my appearance and developed a personal style. I usually feel sexy and confident as Alex, but just as often I don’t because I’m preoccupied that folks are staring at me in judgement. It is part of my character to not want to be the center of attention. I enjoy making presentations to groups, even groups of people high up the food chain. But mainly I prefer to lay below the radar, operating behind the scenes.

In my day-to-day affairs, I wear standard menswear, not trendy and certainly not flamboyant. I look rather average. So, when I don a frock, I am immediately far outside my comfort zone. I go from a reserved guy to a reasonably attractive “girl.” The truth is, I am already far outside my comfort zone when 1) dressed as a girl and 2) dressed as a girl and in public. To expect a person like me to easily frolic about in public while wearing a dress is asking for a tall order. It is notable that this uncomfortableness confirms a reality about me: I am most comfortable as the man I am, but apparently retain a desire to crossdress and tolerate the associated discomfort since the excitement is more powerful.

In the end, I have no delusions about passing as a woman. In fact, that would freak me out a little because I am not a woman and don’t actually want to be one. My aim is to pass with dignity, to be described as a guy who looks pretty damn good in a dress.

Thank you girls for taking the time to read my article. If you have a few moments to spare, please take the time to either send in a response to my article or to one or more of the questions I’ve posed to you below.

Sincerely, Alexandra

*If you have opportunities to be dressed as a girl while out in public, what internal feelings do you experience?

*Did any of your immediate family members ever discover your feminine items stash while you were still living at home and what was the result of their discovery?

*How have your cross dressing skills evolved over the past years or decades for the betterment of your overall look as a girl?