By Alexandra
As with all things, there is a beginning. In terms of my crossdressing, the seeds were sowed during puberty. From about 1982 to 2006, curious but relevant behavior would emerge. Moments of semi-crossdressing would take place during rare opportunities as a teenager. Some crossdressing, on a few occasions, did take place during my military career, which astonishes me today because had it been discovered I would have been drummed out in a very embarrassing way.
Then there was the era of buy-and-purge, from about 1999 to 2005, whereby items were purchased, worn around the apartment, then disposed of. I did take several photos of myself during that time, but these were deleted. How I wish I hadn’t done that!
In April 2006 Alex was born while I was living in Atlanta. I fondly recall the crossdressing that took place in the months just before, with some instances involving brief road trips en femme to a mall parking garage where I could step out of the car and do the most scandalous of things like…walk to a wall and back when no one is around. It was a big deal because I would be well outside my comfort zone. Still, my hair was not quite right. My style was a bit clunky and details were ignored. Things didn’t fit altogether well. My makeup was problematic. But in April of that year, I nailed my look. Everything came together.
More than likely, since 1982, the essence of Alexandra was coming together, albeit slowly and so far below the radar that I was not conscious of it. Obviously, the right ingredients all came together in 2006. But what exactly did those ingredients produce? Why did the result “hit the mark,” so to speak?
As you might gather, I have a theory. I discovered crossdressing as a byproduct of puberty. I was a heterosexual boy discovering my interest in girls, and articles of femininity served as proxies for the real thing. After all, there was little to no chance a dork like me would actually hook up with a girl during that time. Since my mom was the only woman in the house, her clothes were all I had access to, and even then, it had to be items she would not immediately notice being absent, like hosiery.
The process of half-ass crossdressing during those formative years imprinted upon me a habit, which has remained to this day, although in a more sophisticated way. That which I now call, with tongue firmly in cheek, The Craft.
As my crossdressing evolved, I experimented with different looks. We all go through this process, I imagine. In the beginning, it really isn’t about a look; rather, it is about getting your hands on something, almost anything, that constitutes female clothing. Underwear and hosiery are among the easiest to nab because inevitably at least one woman or girl is in the house and there are usually multiple offerings.
Another is shoes. Combine hosiery with shoes and oh my goodness! After a while, this gets old, and one “escalates” to a skirt or dress. If one is especially fortunate, a full ensemble. This, too, is not quite enough. Makeup and hair become needed additions to the repertoire. The hair thing was complicated for me because I had a short style typical of boys; a wig was necessary. Alas, most of us did not have ready access to these items, especially wigs.
I dabbled with my mom’s makeup in the bathroom, which was fine, but sometimes I didn’t scrub up very well and mom noticed a little dark around my eyes. Whoa! A stupid oversight I never made that mistake again, and my mom apparently didn’t seem inclined to follow up (“surely, my son wouldn’t dare to try on girl stuff. Not my son.”) Eventually, high school and the military got in the way and crossdressing was effectively stalled.
Flash forward about 15 years.
For some reason, in early 2006, I developed the urge to go “full throttle” on crossdressing. I purchased underwear, dresses, shoes, and makeup. I even went so far as to order silicone breast forms, false nails, and, of course, a wig. But what style? At first, I had no idea where to start. I browsed online and selected a few styles I liked. Everything was delivered at my front door during the winter months of 2005-2006. I remember well the weekend when I put the whole thing together; the anticipation during the week prior almost killed me. On that weekend in mid-April, Alexandra came together.
In the blurry excitement of getting my act together that month, a process was taking place that I only came to understand many years later. I was modeling Alexandra based on an archetype, a kind of template. This archetype was informed by images from my life experience, combining girls I was attracted to in school and the military, women I saw in television and film, the old Sears catalogs (some of you know what I mean here!), and so forth. The traits I found attractive all came together to form this physical archetype of an ideal woman. I was using this to select clothing, makeup, and wigs. The photo above, taken in June 2006, is probably the earliest successful manifestation of this archetype.
There is another, a Freudian aspect that exemplifies this archetype theory; I found the result I produced to be attractive. At first, the initial version of Alexandra was a bit awkward. But I quickly got my act together. Looking in the mirror I found myself attractive from a heterosexual perspective. WTF? How could this be? What sort of perverted personality trait is this? In the end, I stopped worrying about this perspective because it eventually made sense to me. I was using my body to reproduce an image of my ideal woman from a physical perspective. In a strange way, Alex became a sort of ideal girlfriend. I could summon her whenever I wanted. She never complained. She dressed the way I liked. And, of course, she was smart and liked me 😀
I’m being a little flippant, but one has to admit it is amusing. Especially so given that relationships can be deep and fulfilling beyond my expectations, as I have since learned: I met my wife in 2015 and have been very happy ever since. I have not told her about my crossdressing, and the reason for that will be explained in a future article. As a result, the opportunities to crossdress have diminished significantly; I can only bring Alex to life twice per year. As it happens, that’s plenty. My life is fulfilling without crossdressing… but it is such lovely icing to put on the cake now and then.
So, there you have it – Alexandra is a superficial archetype of my feminine ideal.
Who do you model your look after? Your first girlfriend? Your spouse? Someone you admire? A combination of people you’ve met through the years?
Until we talk again,
Alex
13 Responses
You’ve nailed it once again for me Alexandra! As a late bloomer who did not have the concern of shame or guilt hanging over his head, I had the advantage of putting together my persona fairly quickly and methodically. I could not put it into words or philosophy (as you have so well) but even at the time I was aware that creating, as best as I could, a physical image of the kind of woman I would want to be with, or even be if I were female. When I finally had my act together well enough to purchase my first outfits and wig, and apply makeup without making a big mess, it was easy to see the image I was going after…none other than my wife. My clothing choices are the kind she would make for herself, the makeup the understated approach she prefers, the wig style and color much like hers, when it could have been anything else. I know i don’t look like her – she is pretty and I am not – but it is at this point my imagination takes over and I become that person, if only in my mind. My goal now is not to become that person, but like yours it is to refine that image of femininity to the best of my ability – a high learning curve to be sure, but a very fulfilling and exciting one to undertake.
Kris,
This made me laugh.
My style is very different from my ex-wife. For example I like more make-up than she wore, and I think I’m better at it too.
I think we all have an idea how a women might look like and try to achieve that. For you, it was you wife.
I think there’s an air of inevitability in trying to become the type of woman we find attractive, at least when opportunities to cross the gender divide are limited. After all, we are looking at ‘her’ through an otherwise normal (whatever that means) male lens. I can only speak for myself, of course, but being able to become someone who, under any other circumstances, I’d want to get to know as a minimum and possibly date is what took me from a mindless crossdresser getting kicks from putting on hosiery ‘n’ heels to a more complete person that feels able to interact with others as ‘her’. We often talk about validation but, in the end, the only person who really matters is ourself and if we can look in the mirror or at a photo and think ‘yesss!’, that’s really all we’ll ever need.
But it has a strange consequence. Again, I can only speak for myself but as I’ve become more accepting of this side of myself, I’ve experienced an increasing desire to tone everything down – lower heels, trousers & tops instead of skirts & dresses and so on – because that’s what ‘real’ women do for much of the time. It’s perhaps a case of adding a third dimension to what was previously just a two dimensional existence, based as it was on mirror reflections and photos. I still like the ultra-feminine look but with self-acceptance came the realisation that it’s not the be all and end all.
Amanda – thanks for your perspective. In fact, the subtle angle you provide on this archetypal approach is not one I considered before; that is, to complete the picture, to take it beyond the ephemeral to the more substantial. I like that and it is how I feel – all up or nothing at all!
On the second point, I think I understand this sense of “dressing down,” too. I love casual outfits that make one blend in with the world, but not so much so that the sense of what I’m accomplishing vanishes. Part of what I like about crossdressing in public is the “scandalous” nature of the experience. I am pushing the envelop in my own way, an introvert who nevertheless puts on a frock and wig and ventures forth. It occurred to me some years ago that to do this is very much outside my comfort zone, that to do anything more would be going beyond (say, singing in a drag bar, which one friend of mine loves to do).
Alexandra,
I don’t think I had a role model , looking back I feel my look evolved by gradually getting more proficient in makeup and clothes I felt looked right for my body shape . I guess I’m jus ME !
One turning point was a visit to a retail wig shop , trying on a selection of wigs in differnt styles and colours , it was an Aha moment when both the SA and I both sighed knowing the right choice had been made . I admit I never expected to go blond but it worked for me , I soon realised makeup is dictated by the choice of wig , blond hair does not compete so much with makeup so the whole look beacme more natural . Once those choices were made I haven’t varied very much from them , I knew I could go out with confidence because I had built my identity and that I beleive is the important point , once you have discovered that look stick with it because people need to become use to your look , too much experimenting can be confusing . Lets face it it had to work for me because I took the step as a transgender to come out full time , now I’m gradually building a lovely life around that .
Teresa – thanks for reading my article. And you are quite right to pursue that which makes you comfortable. Social media has confused this for a lot of people, especially the younger generations, when looking the same seems to be in vogue (in an odd twist – that which is considered “different” is not so different at all).
In any event, transgender and crossdressing are two very different things, even if there is an overlap. For the latter, which is the part I am qualified to weigh in on, the experience is akin to an artistic hobby and as such benefits, thrives, in fact, on experimentation. So, sometimes my look changes radically.
Alexandra, this article really hits home for me. The manifestation of the archetype that you describe is about 100% how it evolved with me. Like you, started in puberty. Also a dork that wanted female companionship, was awkward and introverted and coped with feminine clothes. Things evolved. I am not much into “fashion” as much as I am into “style.” And that style is 1980s (and 50’s retro to some aspect). My formative years were the ’80s though, and I was heavily influenced by women on TV (those skirt suits and soft big blouses!) and yes those infamous Sears catalogs. Was even influenced by my school teachers. I WANTED that look! Every chance I got I would sneak my mom’s clothes.
So I dress to the archetype that I personally appreciate from the feminine perspective. And that isn’t “sexy” per se but more a demure modest woman. And interestingly enough my wife, when dressed up in a skirt & blouse, has some similar traits (although I am more girly girl at heart and she is more tomboy at heart). I am thankful when she gets fancy she gets fancy even if she is more jeans and tshirt on the daily. And also my wife knows of my feminine self. I came out to myself (and then to her) 2 years ago and into a 20yr marriage. She loves me unconditionally and for that I am grateful.
I kinda hate using the term AGP with this manifestation but there is some aspect to this to be honest. But also, I identify past CD and am more gender fluid to transgender as I have found after years of “repressing” my femininity there are things about me that go beyond just clothes.
Anyway, just a really great article Alexandra! I am looking forward to your future articles.
One question, if you don’t mind, did you get into the Military to help repress your feminine feelings?
-Christina
Hi Christina! Thank you for the thoughtful comments about your experience. This blog is so great because of the meaningful dialogue it inspires!
As to your question, the answer is no. I joined the military for a combination of vague reasons: 1) Not interested in college (I ultimately did go and earned a graduate degree), 2) not sure what the hell to do with my life, and 3) because it’s the family business!
I am a wannabe crossdresser who did do the early puberty thing wearing of mom’s and sister’s stuff, purged and thought it was behind me mostly. I would have cross dressing dreams that I liked while they happened but annoyed after waking up.
I’m in my fifties, married with older children and jealousy of trans-women wearing fem clothes has erupted. I wish I could have a gender “rumspringa” where I can shave my body and explore without judgement and I would like to “get it out of system”. I don’t think my female side is particularly strong, but it would be nice to indulge “her”. I’m stuck in a closet with this for now.
Tina, you might find that you wouldn’t “get it out of your system” but the inverse happens and you would crave more. In terms of repressing the feminine self inside, if she gets loose, a lot of times she wants to stay out.
-Christina
I read this earlier today but did not comment preferring to ponder it a while. Alexandra’s description is spot on for me and probably the best explanation of my thoughts on the motivation to crossdress. Over the years I have heard many explanations usually laced with words most likely borrowed from a therapist but this one obviously comes from the heart.
Thanks for posting it.
I would also like to comment on not telling the wife which is very dangerous. I have 1st hand knowledge of friends getting caught by the spouse with tragic repercussions. The longer the marriage the worse the hurt when she finds out she was deceived foe her entire marriage. In my experience is far better to be in a position to control when and how she is made aware of your crossdressing. If she gets suspicious and starts doing research on her own without guidance she can read things that don’t apply forming inaccurate conclusions about you. Its far better for you to explain exactly who you are and most importantly where you are taking it.
I don’t mean to preach its just that she will eventually find out one way or the other.
I agree and, in fact I managed to eke out a five part series here on KL doing a deep dive into the whole issues of coming clean to spouses. What I completely overlooked when I came out to my wife was how she’d feel when she found out she’d been deceived for over two decades of marriage. That particular wound can take a lot longer to heal than the one caused purely be the CDing.
Every marriage has its secrets and in some cases keeping secrets can be beneficial. At one time or another we all make errors of judgement and, in the cold light of day, realise that we have overstepped the mark. Much though we’d like to relieve our conscience by confessing, we have to make a value judgement on whether the other party would benefit by knowing. The problem with CDing, though, is that it tends to be sustained and is often an intrinsic part of who we are. It’s also an issue which many wives say that if they’d known about it prior to marriage, they would have walked away from the relationship which heightens the feeling of having been deceived when they finally get to know about it.
This is an extremely complex issue and there’s no right or wrong answer. In the end, if we do decided to function under the marital radar, all we can realistically do is to have a compelling explanation rehearsed in preparation for the day when the proverbial hits the fan.
Alex,
I’ll be honest. I’m quite jealous of how completely amazing you are at your craft, to use your term. And I am glad you have been able to build a complete and satisfying life. My one disappointment, and this is NOT a criticism, was that (if I read correctly) your wife isn’t aware of Alex’s existence. And I’ll admit that I hope someday she will be introduced to Alexandra and embrace her fully.
This is, perhaps, wishful thinking and projection on my part. Things went badly when I finally introduced my (ex) wife to my female side in person, (she knew I liked wearing womens clothes). I always hope that others might have better outcomes.
At any rate, you’re gorgeous!
Kim