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?


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.

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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,





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Kendra Woods
Active Member
7 days ago


Wow! Do I ever identify with so much of what you have written. The timeline and progression, etc. Great article.



Kendra Woods
Active Member
15 hours ago

You are most welcome. I was looking at your Flickr pics and saw Heidi Phox, who I admire greatly. Where did you have “high tea” together? I would love to go to an event like that.

Dorothy Brinson
Active Member
4 days ago

Great story Alex. First things first. I want to thank you for your service to our country. I started cross dressing at an early age. Playing dress up with my sisters. My mom did not like it. I would borrow things or buy things and try to hide them. My mom always seemed to find them and take my cloths away. I kept my life secretive when I served in the military. I met a women who I fell deeply in love with. I opened up to her. She in turned called the ship I was on and told them… Read more »

Jayne Mansfeel
4 days ago

Alex, the look you settled on is fabulous! And thanks for including your Flickr — I really enjoyed those photos, too, they have a certain kind of “chemistry” … Also, nice legs!


4 days ago

OMG thank you Kendra!

That was so well spoken & expressed! Very artful! A lot of that sounds so similar to my life with high school & the military.

I recently went all in tho CD & I’m loving every minute of it. Still learning of course.

Thank you so much for sharing!

Hugs & Kisses Hun!

4 days ago

It was my pleasure. Thank you I really appreciate it!

Winter Clark
4 days ago


That was a wonderfully written and well paced, I can see the processed as I followed it as well. I have since identified as Trans and remember those days fondly and excitingly for the adrenaline rush and the fear of being caught. It brings back fond memories.

Thank you so very much.


Petra Jonson
2 days ago

Alex, without question, this is one of the best written and most insightful articles that I have ever read on this wonderful site. Yes, our female alter egos are our archetypal, dream girlfriends. Without a doubt, my interactions with women I have dated IRL has influenced and shaped my dress, style, carriage and comportment as Giselle, making her the ideal girlfriend. I can’t wait for future essays from you. You “get” and “see” me. Thank you.

Clarissa Cross
1 day ago

Mostly I try to model my SO since she is very feminine and really likes swearing foundation, often we buy the same clothes though in different sizes.
Great article.

Kelli Marlowe
Active Member
1 day ago

Looks like I’m far from the only one for whom your thoughtful and extremely well written article hit home.Consciously or not, I think we all create our illusion from a variety of our past, be it ex-girlfriends, schoolmates, entertainment personalities,or other gurls.Thanks!

Marie Chandler
Trusted Member
1 day ago

Thank you for sharing, Alex. I’ve been processing your article for days. Hoping to come up with a worthy comment, but the more I think about it, the deeper I go and the further I get from being able to write something succinct enough to work in this format. Suffice it to say, many of your experiences and revelations mirror my own. I’m also able to see how crossdressing has developed in stages in my life. The period where Alex first crystalized for you is the stage I call my Great Femme Awakening. It was a point in my life where I… Read more »

Bree Heath
Active Member
23 hours ago

What an interesting idea. I had never thought to question the origin of Bree. Bree didn’t exist before I found CDH. Well, obviously she was in there somewhere but didn’t have a name. I will be thinking about your question for a while. I would have to say I am attracted to Bree. Few people have seen Bree in public and I am the only one who has seen her in private. On the path to enlightenment I have been a little slow in my progression. I do long for some insight into why she exists. I just told my… Read more »

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