Icarus was a Cross Dresser.

Yes, a random statement but let me explain.

Icarus set himself the goal of flying like a bird and, as the story goes, was able to achieve that dressed in a suit of feathers. He was able to soar with the birds, become one of them if you will, but he then set his aspirations much higher. He wanted to get even closer to the sun. It was an aim which he was unable to achieve without his suit of feathers being scorched.  Then he fell back to earth and… well, let’s just say it wasn’t good for our formerly feathered friend.

Makeup Magic

By now most of you are staring at this and wondering if I’m drunk or on some solvent or maybe I should be on some meds while I write this, but I’m getting there.

There have been mutterings around the closet doors forever about not being presentable or pretty enough or photogenic enough to pass, or even to be on CDH. Now, I’m here to tell you that is BS and explain why.

In our perfect fantasy worlds, we are able to come home from work, shower, slide into fabulous outfits, post wonderful pictures of ourselves, and even go on outings without anyone batting an eyelid in our direction, except maybe to admire our shoes or our fashion style. But I’m sorry, for most of us, that is an unobtainable standard. Those of us who are closeted are destined to struggle in this area. That doesn’t mean it isn’t possible, but its tough. Real tough.

Firstly, we can’t commit fully to feminizing without triggering off questions from our workmates and family. Shaved bodies and plucked eyebrows will probably get noticed by most women and some men too. A skin care regime will make the wife notice at least and, if she doesn’t know, trigger her into wondering what’s going on (but that’s a whole different article). Sure we can talk about aging and the sun ruining our skin or we are cycling so need to shave our legs but those excuses only work for some.

Secondly, if you are new to this whole “dressing up thing”, your wardrobe will be limited to what you can cobble together.  So, putting together a perfect ensemble suitable for the catwalks of Milan, let alone Walmart, will be difficult. And then we have the makeup fiasco…. Oh dear God help!!!! How many of us have watched the videos online and thought, “piece of cake”? But when we are finished, it’s not a beautiful lady with delicate features and highlights looking back at us but rather someone resembling a raccoon after a 3-day booze bender with a few brawls thrown in for good measure that is staring back. I put my hand up for this being my signature look if I try to go for the sophisticated, night-out, smoky-eyed, feminine appearance….sigh.

Thirdly and maybe the most difficult is that we are dealing with the bone structure and musculature of men. Sorry, but some of us are doomed not to be delicate flowers. Of course, we can try diet and exercise that will shrink us a bit but if you are 6’5” and have shoulders of a linebacker then that little black dress with killer 5-inch stilettos might never be the best look.

And you know what. Who cares? Yes, I’d love to manage to be able to sneak out in public and not be seen, to blend in if you like. But to what end?. I’m closeted and my only outings have been to a friend’s place who knows me as both male and female. So she’s not going to be a good judge of whether I blend in. She has an image of who I am as a dude, so that image will always be the one she puts against my fem side.

Okay back to the pics.

We all see pictures here of ladies who we think are gorgeous. Yes, let’s use that word. They’d turn heads anywhere they went dressed as they do in their pictures. And we secretly hate them…No… I’m kidding. We are envious and we want to be like them, but we don’t hate them. We hate ourselves for not being able to attain that look ourselves. We hold their images up to the standard that we must meet to be considered worthy of the title Cross Dresser. Of course what we don’t see are the hours of practice that went into perfecting just one aspect of their look. Or the time spent looking through clothes and getting things that matched perfectly. Or the time they spent with someone whose job was to make them look fabulous for that one photo.

Yes, some of those shots aren’t pics of people who’ve just got home and slipped into something straight out of the shower. They aren’t generally closeted. Some of those people are further along the spectrum than just being a CD. They may be in the process of transitioning and as such have had years of time to work out their look. To figure out the best angles (let’s face it we all need help in this area) and perhaps the bodies they are presenting aren’t quite what they used to be. HRT, supplements, diet and exercise regimes, as well as possibly surgery, play a big part in where they are today.

The important thing to remember is that at some stage they were where you are. They had that raccoon looking at them. They had the dude in a dress look as well and had “picture envy” of some gorgeous woman they held up as their standard. And also if you can’t attain that standard because of the stuff life throws at us, then why set the bar that high? If you love the feel of silky undergarments or the swish of a skirt against your nylon clad legs, does it matter if you don’t have the same portfolio of gorgeous photos? Those photos shouldn’t be what you allow to define the you that you want to be.

Be true to who you are. Enjoy what it is that you enjoy. Don’t listen to others, setting your goals based on their goals, set your own. Our lives are all different, our situations are different and as such we can only succeed where we control the journey.

Lofty goals are great but if you reach too far, the price may be too much and it could cost you far more than you ever thought.

Okay, Icarus probably wasn’t a CD, but he tried to overreach and in the end he went too far. Besides, someone with that much of a liking for feathers has to at least be a drag queen.

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Sarah Daniels

Im a Wannabe writer. Short stories so far but I want more. Like everyone I think I have a novel in me somewhere, but not sure what it is yet. Have a few things on the slow boil and a couple of cold cases tucked away for another time.

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Jasmine Jewel

Like this article. I will never be pretty…except pretty ugly…and I noted Dustin in Tootsie had a conditional contract for making the movie. He spent a year on the streets trying to pass as a woman but he had a team of makeup artists…and spent six hours for the makeover. He had some holly wood star girlfriends taught him how to pop in and out of feminine sounding voice. And in the end he was disappointed because he was hoping he could be made into a beautiful sexy looking woman. At least he could pass after massive efforts and resources… Read more »

Mitzi May

That is do beautiful and thank you for writing that. I’m at the start of this journey and what you said is both comforting and aspirational.


Wonderful article Sarah! “Be true to who you are”
Hugs, Liv

Active Member

What a great article… a must read for anyone in their journey crossdressing.. I always adhere to
the philosophy “practice , practice makes permanent” and enjoy the process.
thanksSarah for sharing looking forward to more articles , regards. Leonara

Jamies time

That is a very true story I myself may not ever be a beautiful girl but I don’t care i will do all I can but the main thing I am happy. I know since I have started living my femmine side it helps with job stress and life as a whole I am not going to give up.

Dame Veronica Graunwolf
Active Member

Hello there Sarah. I must admit you write a terrific article. I envy you. Yes, I think everyone who cross dresses or is new to the game must look in the mirror, take a good look at themselves and examine what that hunk of clay really is and what we have to work with. One can always take oneself’s off to the plastic surgeon and have it carved into something smashing. But…Dolly Parton with Hulk shoulders and giant guns??? Naw….can’t be realistic. It is painful and expensive and sometimes the results are worse than before. As the Marines said……”Be All… Read more »


This is me. I want to be pretty, feminine and sexy. It is not my desire to appear as simply “a guy in drag”. I enjoy being a guy because that’s who I really am. However, when I dress, I want to pass as pretty, feminine and sexy. Yes, I do enjoy wearing silky things, feeling the swish of my skirt against my hose.. wearing pretty three inch heels.. I do hate the wig though.. but if I could just master the make up. I know, I know.. its more about how you feel than how you look. But for… Read more »


Hi Hannah I just read your post and you’re not alone in the way that you want to look. I’m the same way. If I can’t look like a girl dose and look sexy and cute then there’s no need for me to go out dressed en.femme. I have a lot of feminine clothes that I’ve spent hundreds of dollars on. This is half the battle for me to get the look I’m trying to get. The other half is makeup and hair. Again I’ve spent a lot of money on getting a perfect wig that doesn’t look like a… Read more »


Thanks Janine… I had bought my first dress a few days ago. I’ve always been wearing a skirt and top, but this is my very first dress. So excited! Perfect match with my new wig and heels. Just need to try make up. A couple of years ago I had a very nice pair of slingbacks, lost them in a purge. Looking for another pair. They’d fit me perfectly. 2-inch heel. I have several pair of pumps now that are 3-inch. Very pretty, but make my feet hurt.


Persephone Androgynous
Persephone Androgynous

Great article Sarah. It’s easy to forget that this is not a competition and that this is really about expressing who we are. Some of my favorite photos on here are the ones smiling and laughing. Especially the ones laughing, that is so cute and sexy to me.

BillieJo55 Smith

Wonderful article Sarah, a wise friend once told me that passable is in me. That I shouldn’t try to please anyone else, just myself. It has helped me dress & go out enfemme with her & others. Loving myself & I have the motto “I Don’t Care” what anyone thinks. Just be me.


Danielle Wayne

Very inspirational. Thank you

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