Bringing the superficial feminine ideal to life through crossdressing

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!


As you recall from an earlier article, 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?

EnFemme Style


As you might gather, I have a theory. I pointed out in my first article on CDH that 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.

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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,





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Jamie Taal
Active Member
1 year ago

This is exactly me “to a T” without the obvious successful “passing” that you obviously achieve. You look fabulous! My first “looks” were too gathered from your afore mentioned catalogues and also television. For me in my adulthood, I now try to emulate the amazing women in my design profession. I’m jealous of the “ease” with which they can present themselves. I look to them for fashion cues, successes and the occasional failure. For that reason I seek out specific styles and not just rely on what i can get quickly or cheaply. In the past I’ve spent too much… Read more »

Active Member
1 year ago

Hi Alex, your post is amazing, and impacted me on multiple levels! Thanks for sharing it!! I went through almost identical patterns, although I started younger, way before puberty. I did not do military, but spent my HS years at a private religious boarding school in the South (most of us would recognize it for a variety of reasons). It was basically the equivalent to a military-style environment, without the 20-mile hikes. 🙂 I really identify with your approach to crossdressing as a craft. I just came out to my wife recently and borrowed some of your thoughts from your… Read more »

1 year ago

I showed my wife your picture and said how lovely you are. She said ‘yes she is’. I was hoping for a more enthusiastic response. Oh well.

You are lovely.

Sybilla Valesian
Sybilla Valesian
1 year ago

Hi Alex, What a great article thanks . I read your article and then went for a walk to consider the points you make. I have to admit to being ashamed of my dressing and no matter how many times I tell myself to stop being silly, it doesn’t go away. Syb got out last year and in so many ways has been very good for me, in allowing me to finally empty the box of all the negative emotions that have were buried in there with her. I love the line “After all, there was little to no chance… Read more »

Last edited 1 year ago by Sybilla Valesian
Sybilla Valesian
Sybilla Valesian
1 year ago

Yes, I’m aiming for a better person, kinder, more honest, more understanding and less reactive

Jenn (Jennifer) Scarlet

Hi Alex. An excellent post that resonates with me. It reflects my own development and, more recently, my own thoughts and reasoning about why I cross dress and what I gain from it.

You didn’t say, specifically, who you model your look after other than to achieve some female archetype. My wife is aware I cross dress but I’m not sure how she’d react to the idea that I am dressing to be my own ideal woman!

Jenn (Jennifer) Scarlet

That is a fair list indeed Alexandra. Like you, I am also 52. And finding that my dressing has been maturing into those feminine styles which would be described as sensual, stylish and elegant as opposed to overtly sexualised. I am increasingly dressing my age rather than my shoe size!

And, if I may say, you have not changed that much from your 2006 picture. Quite gorgeous.

Sybilla Valesian
Sybilla Valesian
1 year ago

I do wonder if greater understanding will help me become a whole single person, a better dressed, elegant guy ( I take that’s what you mean by hang it up for good)

Tiffany W
1 year ago

You look amazing Alex. I know first hand how easily the military can make you feel like shit sometimes. Also how the people doesn’t like to keep their mouths shut if you confide in them about something and turn around and everyone knows. Now those people are giving you hell about it. Anyways, I actually started crossdressing during my time in the military. But I’ve always found women’s clothes more appealing then guys clothes. Why is kinda funny is that one of my coworkers thought I wear makeup when we were on rotation I’m Germany. And that was before a… Read more »

Trusted Member
1 year ago

Really great article Alex – thank you for sharing it. Your evolution as a CD sounds almost identical to my own and, I believe, a great many others of us. “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?” Not sure if you’re familiar with Blanchard’s theory of autogynephilia – basically a man’s propensity to be aroused by the thought or image of himself as a woman. This idea that almost all MtF CDing is rooted in the erotic is quite controversial because it… Read more »

Jane MacLeod
1 year ago

Can relate to much of what you have covered in the excellent article Alex.
Although was wearing pantyhose from a very early age the step into crossdressing was gradual around puberty.
Had the frustration of getting access to clothing and wigs etc. The part about not cleaning makeup from your face properly is so true for me.
Do find myself sexually attracted to myself when fully dressed whatever that means!
Unfortunately never had ability to perfect my makeup and style so far. Hopefully will some day.

Claudia Newday
Active Member
1 year ago

I was surprised that I I had this Samantha Stevens (Elizabeth Montgomery) thing going on with my look. Now I realize I was channeling her. I had a big crush as a boy. She would have been considered an ideal woman for me at the time – and still is: confident, sexy, and beautiful.

Peggy Sue Williams
Noble Member
1 year ago

Excellent well-written article, Alexandra! At times, I was reading about some of my own behaviors on this fantastic journey of being a CD. Much to my surprise, I model my look after a combination of people I have met through the years.

Peggy Sue

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