Not Pretty Enough?

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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  1. Viola 2 months ago

    I understand what is said about accepting you as you but I have not found me yet so I will be my own worst enemy on my acceptance of appearance as viola

  2. Iam a 58 year old man 25 lbs overweight [199 lbs] and 6ft tall but I have nice legs and and adopt feminine mannerisms easily I turn a lot of heads at distances of 20-50 ft mostly men but I plan on being able to pass easily in a couple of monthes after all I just came out on my b-day Oct 4 2018 and have recieved positive comments after leaving various establishments I have been told by other people later and these compliments were unsolicited!

  3. Freddy Walnuts 2 months ago

    Nice article! I feel a bit better now… I know I’m one lf those raccoons you mention in your article…

  4. Tracii Greene 3 months ago

    I am happy being me and see the girl in the mirror with a hint of the guy that resides there as well.
    Not what I would call attractive but ok at best or maybe look ok from a distance LOL.

  5. Stephanie Drescher 3 months ago

    Great article Sarah. So much truth and wisdom. It is always good to have the right perspective and to have a realistic expectation – without this you are always going to be disappointed. I would love to be slimmer, look like Audrey Hepburn and have smaller feet, but it’s not going to happen and I won’t cry into my martini about it.

  6. June Richards Jewell 3 months ago

    So true. Good article Sarah 🙂

  7. Talhia Swey 3 months ago

    Nothing could be far from the true, the one thing that remains is and it should rule; is not what others think,want,decide,choose, like,feel,live by, be what You feel, I tried and fail miserable to let everybody know that self-confidence, self-esteem , the love and like of one-self is the most important accessory One always must wear, but lets be honest to Ourselves, trying a little bit harder (when possible) will never hurt, Oneself will always be the worst critic, and one sometimes should try to ignore, the journey is not a raceis the journey itself, be yoursexyself!

  8. Samantha G..... 3 months ago

    Loved the article Sarah !!!

  9. Mikki Barnes 3 months ago

    I loved your article and agree with you in regard to knowing limits to goal setting. I’ve taken stock in the reality of looking as good as I want to, and what I think is the limit of me. I realize that I do not necessarily dress age appropriate, but more for how it all makes me feel. I’d love nothing more than to be 30 years younger but I’m not. Thank you for your article, it gives me an affirming feeling. Hugs, Mikki

  10. Jasmine Fletcher 3 months ago

    True words. I’ve probably taken well over 1000 photos so far. I have a favourites folder of those that I like which contains only 23 photos: most of which are slightly blurred (which helps!) I’ve only dared share 7 of those on line so far (but people are very kind and encouraging). I’ve put make-up on that works in a photo at a distance but looks dreadful close up. Wardrobe malfunctions happen frequently. Body hair manages to poke out. I stand awkwardly. Attempts to look sexy make me look constipated.

    But, it has been fun trying so far. And I might yet do better. So on I go.

  11. Michelle Wuvey 4 months ago

    One thing I learned right away, was that there’s not enough make up in the world to make my manly face look feminine. At least nothing short of having a surgeon add/remove bone. Which I wasn’t about to do. Especially at my age (late 40’s). At first, with the help of the wife, I got better looking, in a fem way. But my god, it took over and hour to get that way. And since I was still in the closet to everyone except the wife, plus I live in redneckville, I went through all of that, just to stay at home.
    I don’t mean to sound like a downer, but realizing the truth, that I was getting older and had a mans face, was my reality. With that said, my limits were set, and I’m OK with that. In fact, i was more than OK with it. Simply because I knew I shouldn’t waste my time and money trying to achieve the unreachable. There’s comfort in the truth. Regardless of what the truth is.
    Now, I don’t spend an hour on the perfect make up. I don’t spend hundreds on clothes, wigs and jewelry. I’m happy with the small amount of things I have. My favorite morning things are a cute little short dress I usually sleep in (because it’s sooo soft). D cup sports bra with my breast forms. Comfy heals. And some lip stick. The lip stick I only apply so that I can see the imprints on my coffee cup and cigarettes.

    My only regret is that I did do this when I was younger and more slim. Back when I could’ve been a knock out. “I could’ve been a contender” as the man says. he he he he.

    “That’s the thing about honesty. Sometimes it stinks. Sometimes it sets you free.” Pat Green (From the song “Without You”)

  12. Tricia Lynn 4 months ago

    Love this article! First one I read after a hiatus from CDH. I personally think I could kind of pass if I got out (I am six feet tall and weigh almost 200 pounds, so there’s that) except if I had to speak. It’s tough to feminize a voice that sounds like the “Oom papa mow mow” guy from the Oak Ridge Boys (showing my age here). So even though I feel that I can get myself to look reasonably decent when I don a dress and makeup, I would have to pretend that I have laryngitis or something if I ever had the courage to get out there, which is unfortunately not too likely since I am still deeply closeted.

  13. Brianna Slat 4 months ago

    Great article! Thank you. It really puts things in perspective.

  14. Jenna Salgo 4 months ago

    Thank you for this article. As someone with strong male features, I find the article quite inspirational. Although I’m a bit short (definitely not 6’5″), my bone structure and musculature, including broad shoulders, as well as my inability to shave and pluck without raising questions, doesn’t help my cause. Yet, your analogy of Icarus and trying to overreach helps me put things on perspective. I should focus more on enjoying the little time I get to dress and less on trying to look perfect.

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