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.

Transgender Heaven - Gender Journey

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. Patricia Marie Allen 12 hours ago

    Passing is over rated. “I Yam What I Yam & Dats What I Yam!.” Popeye the Sailor-man.

    I think we all have, at one time, struggled with the passing issue. We buy into the Hollywood image of what women should look like. You know, five foot two and eyes of blue. Beyond that one hundred twenty pounds, 36, 26, 36 and gorgeous hair, shapely calves, delicate hands, high cheekbones, arched eyebrows and plump, sexy lips. Well in the real world of genetic women, it just ain’t so. In my observation, most women come it two categories; those who think they are too skinny (and many really are) and don’t have any shape and those who are fighting the battle of the bulge. The fact is, most genetic women don’t measure up either. Many are to tall, to fat, to plain and yes, some are to masculine.

    Being pretty isn’t necessary to be feminine. Now there’s a goal that we can aspire to and achieve. As far as how we look to be feminine is a matter of simply taking the edge off the masculine look that nature gave us. I went to Merle Norman’s a couple of times to learn how to apply makeup. I did manage to get past that hungover raccoon image, but as my daughter pointed out, all I did was call attention to my face. The face shaped like a man’s face. The one with the hooded eyes and the square chin. Oh, the skin was flawless and the eye shadow was alluring… if you could get past that Neanderthal brow and the big nose. No, when it comes to make-up the adage is right, “Less is more.”

    These days, I settle for mascara and a nice light pink lipstick… that’s it. I am who I am… I have a thick middle; I have narrow hips (I wear a padded panty girdle to make up for that) and I have large hands and feet. However, I go out often. I’m fortunate, in that over the years my wife has become very tolerant but still not supportive. As a result, I have a bigger wardrobe of women’s clothes than she does, including shoes. (My big weakness. I dare not peruse the selections of a shoe store that carries my size. If I do, I’m hard put not to buy something.)

    I’ve found a loophole in my medical insurance that gets them to pay for electrolysis. So once a week, I’m at the electrologist. I go en femme. I don’t really have any men’s clothes any more, having a large women’s wardrobe doesn’t leave enough room. So when I must appear masculine, I simply wear pants and polo shirts or some other masculine cut woman’s clothing. But for the electrologist, I choose from my more feminine clothes, put on mascara and lipstick. I’m there an hour and a half. I’m under doctor’s orders to consume more than 60 ounces of liquid a day. In order to achieve that I drink a 20 ounce travel mug of water in the 45 minute drive to get to my treatment. So 45 minutes into the treatment, we take a break and I need to use the restroom. Dressed the way I am, I’m not likely to use the men’s room. It’s a large office building and it’s rare that there isn’t someone in the women’s room. I just go in, enter a stall, do my business (sitting of course, but then I never stand for such things, not even at home), wipe, go to the sink, wash and dry my hands. The other occupants of the restroom don’t even blink. Some even talk to me.

    OK, I’m 73, age helps. Women of my age often begin to take on masculine characteristics. I’ve grown my own hair out and wear it in a simplistic feminine style. Whether I actually pass or not, is unimportant. I act like a woman, dress like woman and the women I come in contact with in that woman’s sanctuary, accept me as a woman. I have no illusions that every one of them has no doubts. But the fact remains, none of them challenge me there, because I comport myself as a woman.

    Adopting a feminine nature and presenting it to the world will go a lot farther toward being accepted as a woman than looking good. If you were able to attain that perfect woman’s image and didn’t present a feminine persona, you’d find that no one would accept you, because they’d see you as a guy in a dress. Whereas, having imperfect looks, but projecting feminine in comportment, lets them see you as an average woman.

  2. Alison Elliott 2 days ago

    Hello Sarah,
    I can fully relate to what you have written. There is so much that is all about me.
    I am 75, but in my mind I am less than half that age! I have dressed a few times a week for the past 30 years, with many long breaks, including two purges and I only wish that I had kept going with it more than I have in the past.
    My Wife is fully understanding, so I am very lucky, so that is not a problem. We went along to a Trans Pride show last month and spoke to someone on a stall and they openly said “After all it is only clothes” It made me think.
    I do love the feel of nice silk, satin, leather and lace.
    Recently I did buy some outrageous stiletto shoes, black with 5 inch heels that I saw in a local charity shop, I felt like Cinderella when I tried them on and they fitted. I am not sure how I will cope with trying to walk in them ! As I do have a badly formed toe on one foot which raises the centre joint of the toe up to form an arch shape, this does make the choice of nice size 9 / 10 UK footwear a real problem as my toe rubs and I get blisters.
    I seem to love dressing in black, I think black suits me.

  3. Jack Straw 3 days ago

    Hit home good.piece

  4. Amanda Patrick 3 days ago

    Hi Sarah,

    Thankfully I never seemed to have High Expectations for myself. The first person that helped with my make up told me I had nice skin for a male person. And that I would be easy to do. I have 3 Items that I use. And Recently my wife gave me some blush to try also. I went with the advise I have been Given. And so far things have worked Out. Of course we will all have those Nerves . I was all so over weight at First but went out any ways. To Safe Spaces of Course. But yes we have to work with what we have been given. To me it just seemed I was determined to go out regardless.

  5. cdmelissalaquinta 4 days ago

    Wow! Your article touched so many nerves in me, and on so many levels. I, too, fantasize about looking runway-model gorgeous and going out clubbing, while being ogled and admired by men, women and other cd’s. But alas, having purged one too many times, I’m stuck at home with bras and panties, and cute sleepwear, that I can only share with my tolerant but not wholly supportive spouse. Oh to be dressed, made up and out! (Sigh)

  6. Sarah you have a great gift for writing! Id love to read more by you! Thanks for a great article that made great points!

  7. Rhonda Roe... 5 days ago

    Great read Sarah. So on point. Thanks for sharing.

  8. Rozalyne Richards 5 days ago

    Hi Sarah well what can i say i identify with your story what i see in the mirror is a man in drag and not a beautiful woman, I’ve tried putting makeup on and I’m not very good at it i would need a professional to help with my make-up to make me look anything resembling a woman, i know that i would need a lot of hormone and surgery to make a difference in my appearance, that’s why I’m still in the closet because i don’t think i would be able to really pass as a real woman outside off my bedroom, i do love to wear my female attire I’m not sure why but I’ve been c/dressing most of my life, hugs Rozalyne x

    • cdmelissalaquinta 4 days ago

      Hi Roz: Well, Ive seen your profile pic and I disagree that you look like a guy in drag. You look perfectly feminine. I’d love to be your friend, and we could dress and get made up together. XXOO

  9. Danielle Wayne 5 days ago

    Very inspirational. Thank you

  10. BillieJo55 Smith 6 days ago

    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.


  11. 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.

  12. Hannah Rogers 7 days ago

    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 me.. its also about how I look. I suffer from depression anyway, and when I can’t achieve a more feminine look, its not only disappointing, its depressing. Not only that, but I want to be able to go out without being threatened and ridiculed.

  13. 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 You Can Be”! Todays’ women (GG) are changing their format. Girls are getting into sports, body building, and business. Look around everyone….girls come in every shape that males do….I have seen 6 ft women, my neighbors wife is built like a linebacker but when she dresses up……..I would not hesitate to go anywhere with her! Realistically, women today can be anything, but runway models, very few fit the bill of what the fashion industry tries to tell us is “the way to be”. so…lumps of clay….experiment and get all dolled up. I think you will be surprised at what can be accomplished……are we all not artists, sculpting something beautiful???? It is amazing what make-up can do. I know a girl who has a Siberian husky dog….she also in a pro make-up person in the Media. She posted a picture of herself and her dogs face. Several images where the various stages of applying make-up to look like her dog. End result…..a photo of the two of them that you had to study for a while trying to figure out who is who, Fantastic! As to cross dressing……experiment with your outfits, use the various techniques of shaping garments, silicon and foam rubber and hairstyles/make-up. Practice, practice, practice with the make-up. Study the women in your little world, how do they dress, how do they behave, how do they go around looking like women? Look thru all the magazines and get an idea of what you want to be, but bear in mind the clay you have to work with. In time you will be able to sculpt that body into something that your dreams are made of. Make the most of your assets, hide those flaws as best you can. Truth be told…..a lot of Playboy bunnies and MS. Universe contestant have been pumped full of botox and silicon to look like that. We want to be realistic and remain healthy don’t we? Clint Eastwood said….”A man/woman has got to know their limitations”. Go ahead and become Icarus….but remember, know your limitations and don’t fly too close to the sun.

    Best of all things to all of you!

    Dame Veronica

  14. Jamies time 7 days ago

    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.

  15. Leonara 1 week ago

    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

  16. Liv 1 week ago

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

  17. Mitzi May 1 week ago

    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.

  18. Jasmine Jewel 1 week ago

    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 few of us will ever get a crack at and made the movie. ‘It is what it is’ for all of us like you say, and like Harry Potter said when training Dumbledore’s Army…’remember even the greatest wizards all started where we are at the beginning’. I still wanna set my sights high but only on the chassi (BMI body level…health bendfits as well) . After that money, time and opportunity will have to wave the Harry Potter magic wand and see what illusion can be created for a one time photo op…as I will not be transitioning and have to maintain my daily manly image for the world to see. Right now cross dressing keeps me motivated and feeling like I have something here at CDH I could not get elsewhere.

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