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.

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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!

Crossdresser Superstore

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.

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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?

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Alexandra Forbes

I'm a guy. I like women. I like the company of women, I'm married to a woman, and I like to dress up like a woman now and then because it's fun. For me, crossdressing is an art form and an excuse to meet like-minded folks, not the expression of gender dysphoria. I should note that my photos are not doctored up with apps or significantly modified using Photoshop, though I do adjust color, contrast, and that sort of thing. It is important to me that my photos are genuine, with wrinkles, pores, and all. If they aren't genuine, I'm fooling myself and others. I take this art form pretty seriously, so if you don't have much of a profile, no photos, or your photos are obviously fake or heavily photoshopped, I will probably not respond to a friend request. I'm not here to indulge sexual fantasies, talk about fetishes, or discuss what sort of intimates I wear to work (I don't). My hope is to find people who are interested in discussing "The Craft," or the art of crossdressing. I'm also keen to ponder the nature of sexuality and gender, fashion, and makeup techniques. However, I always try to respond to correspondence - we should all help each other out. I enjoy engaging with anyone, frankly! My Flickr page can be found here: https://www.flickr.com/photos/andreaforbes/

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Kerri Smith' class='avatar avatar-64 photo' height='64' width='64' />
Kerri Smith
4 months ago

Hi Alexandra,
What a fascinating article you wrote. I can identify with many of your thoughts and feelings. I have been a crossdresser for many years. No one in my family ever caught me crossdressing but I did accidentally ought myself to my now ex wife when she snooped on my iPad and saw a picture of me dressed. I’m alone now so I can be Kerri whenever I want. Please keep posting. I love your photos and your comments, and would like to think of you as a friend.

Active Member
2 months ago

Great article Alexandra! I know exactly what you are talking about with being a guy who loves to dress up in the wrong clothes but feels better when doing so. One of your questions is what internal feeling do I have if dressed as a girl out in public? For me, I feel more complete, content and much happier. This is very real for me and I indulge in this daily. Your other question is about my stash of girl clothes being found while still at home. Yes they did get found and I got reprimanded for “stealing” those clothes.… Read more »

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