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Alexandra’s Thoughts On Crossdressing

Another all-timer, revisited.

By, of course, Alexandra

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 [editorial comment: check her out, she’s beautiful], Cristy Garcia [editorial comment: LOVE HER as you can see here], 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.



*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?


11 Responses

  1. ALEX,

  2. Alexandra – wow, this really spoke to me, as we’re of a similar age. Thanks for sharing. I’ve become increasingly comfortable being out and about wearing whatever I want, incredibly. I decided to damn the torpedoes almost two years ago and just be openly genderfluid, and it’s been incredibly liberating.

    There’s still that piece in the back of my mind that wishes I could look good in hair and makeup, but I just haven’t found that “sweet spot” where I’m actually comfortable yet. I’m still waiting for that moment like you describe when you found the right wig. I’ll get there, though.

  3. Alexandra,
    Shortly I hope to right about my holiday with the National Trust . It was the first time I had been away with a group who only know me a Teresa . So What were my thoughts and inner feelings ? OK I admit I was hoping and praying the bubble wouldn’t burst on my lifestyle as a woman , it’s wonderfukl to say it didn’t in fact any thoughts or fears have totally evaporated . Personally I feel the moment you let the male side go and think entirely as a female most of your problems are over . Perhaps the obvious questions arise over the your voice and other telltale male signals , I gradually discovered that the first moments of interaction with other people establish your identified gender . That becomes the building block to build your full identity , this is why I don’t experiment too much with different wigs and my makeup , I am recognised and accepted as Teresa . To mix with the groups as I do wouldn’t be possible without that level of accpetance , otherwise after a while you would find in a social group people would gradually ignore you and isolate you , it’s wonderful to say I’ve never expereinced it .

  4. Alex, as always a great post that touched a few nerves (fortunately not the one about being discovered although I do shudder at the memory of a couple of near misses). All of the inspirational names you mentioned were on my list of role models too; I’ll also add Michelle Monroe but, sadly, she’s become rather too handy with FaceApp of late – such a shame as she was, and is, stunning in her own right.

    I’ve already answered your ‘discovery’ question but, as for the other two, I’m definitely getting better (not that I could have got any worse than my early attempts) but I think that self-acceptance has also had a lot to do with it – I accept and love who I am and no longer strive for the impossible with the guaranteed disappointment that that always brought. As for going out and about, restricted to a couple of short walks, I’m afraid, but both times, I’ve had a feeling of complete inner calm without any feeling that I’m either inappropriately dressed or that I shouldn’t be there at all.

    As I said at the outset, this was a great post and, as with all your posts, I think that many will identify with what you say. Realising that we have this need is scary but, particularly for those bewildered souls lurking in the shadows, knowing that those we look up to (i.e. those with, say, 8.1K Flickr followers – that’ll be you then!) have exactly the same highs and lows as the rest of us!

    Oh yes, I nearly forgot – for a guy, you look pretty darn good in a dress!

  5. Hi Alexandra, I’ve been an in/out of the closet for years. Prior to a local gay bar near me opening up and featuring drag shows I only used to get out of the closet around Halloween at work or with friends at a party where it was socially acceptable. The last place I worked before retiring they had come to expect me to be “Sara” every year, this came about after a dare was put forth because for a few years at work I never joined in wearing a costume of any kind. So 1 year I said Ok, I’ll “dress up” and did so to the nines and got to hang out in the office that day doing secretarial stuff instead of my regular factory job, it was a mixed bag of acceptance but no one really hated it. When I’m in a safe environment I’m really comfortable. As for parents finding my stash? As expected, not well! Almost became homeless after that. As far as improved looks? yes it got better to the point where not trying to “pass” during the pandemic I got ma’amed alot! face masks helped alot there. My hair is shoulder length because I can’t find head ware or wigs to fit the brain bucket, I’ve never liked short hair, and for a few hours after a fresh shave with hair down and a touch of lipstick is my no makeup look.

  6. As to my thoughts about being out, I tend to blab on and on about them every Sun-dee.

    No, no one ever found my stash while young because I didn’t have one (but I did have an older sister). Have I gotten better? Yes, I think so, but maybe I just have more confidence now.

    But the real reason I’m posting is because I clicked on your Flickr link (nice pics!) and the first four show that you have incredibly good taste in clothes, because I own the very same dress, which has previously made an appearance in these pages:

    Nicely done!

  7. Alex, thank you for this fantastic post! I checked out your flickr. You look amazing! We are practically the same age, but you look younger. I have been dressing on and off my whole life, I told my wife about two years ago and she is accepting. Her Christmas gift to me was a makeover service for girls like us, so only recently have I been able to take it as far as can.

    I feel like I’m just competent at VERY basic makeup, but would like to be lots better. I’ve been to a few crossdresser events via a local meet-up group. Been out shopping, thrift stores mostly, and to the movies once. I’ve not really spoken more than a few words to anyone while out as I don’t have much of a femme voice. Chatting with a stranger is my next hurdle.

    As for some of your questions; It’s exhilarating to be out en femme, and yet seems like the most natural thing in the world. The more I do it the more I WANT to do it.

    I was never discovered growing up as I never really kept a stash, I just “borrowed” things and put them back immediately.

  8. ditto Teresa. someone recently wrote that you are most passable if young or old and I agree being a member of the latter group.
    As I more and more got out there it required dealing with a HUGE fear factor. I also avoided any verbal interaction with others due to the voice. I now look at myself sort of outside myself and am amazed at the person I have become i.e. a confident elderly woman. Also I have discovered that we tend to make men uncomfortable but not women. I have a lot of female friends and do activities with them

  9. Alexandra, thank you for your post. I enjoy reading about other girls’ journey and expressions of self. Like many my only access to women’s clothing while growing up was my mother’s clothing; at least until I outgrew them. As a little kid all I heard from my mother was I was suppose to be a daughter. My mother’s ideal family was husband and wife, older son and younger daughter. My brother was eighteen months older than me. That ideal family probably was a reflection of what her family was while growing up, although her older brother by five years died of tuberculous when he 21. One evening I rebelled as much as a single digit could. I donned one of her nylon nightgowns and cried that she did not love me because I was not a girl. She consoled me, saying she loved me, and never told me that again. However, the discipline she doled out would qualify as child abuse; lots of red welts on the back of my legs. My older brother was the golden child. Whatever caused me to start delving into my mother’s clothes, I don’t know. First, it was her nylon full slips which led to her bras, panties, girdles, nylon nighties and a singular sundress. One day I snapped the strap of her sole black bra. Yikes! My mother and father tried to catch me in the act and almost did. I don’t know what would have happened if I would have been caught. My father died that year (1965) if cancer. They were homophobic. Back then, to be a crossdresser was to be thought of as a homosexual. I attended a “subway college” and graduated in 1969 and was drafted into the army. When I read of all the hate thrown out for the LGBTQ+ community it brings back my internal feelings of inadequacy I felt as a teenager. A man can check off all the approved boxes on the list of accomplishments but that lure of women’s attire can negate all of that. It’s inconceivable to me that society is slipping back to the 1960’s.

  10. You look fantastic for a man in dress. I enjoyed your pictures and video clips on Flickr too. My story of how I got started is similar although I’ve only been out to people online for only about 4 years now. No one in my personal life is aware of it. When I was about 12 years old I got caught wearing my mother’s clothes by my older brother when he unlocked my bedroom door and burst in. It was so embarrassing and I thought my life was over. But he just laughed maniacally at me and left. Never said a word about it to me or anyone else that I was aware of after that.

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