Learn how to cross dress

The first time a man puts on a dress he looks like – a man in a dress. In our minds we picture ourselves as dainty, feminine and gorgeous, but we’re actually a man caught wearing girl’s clothes. Looking good as a woman is a hard thing to do – just ask any lady who has spent an hour doing her hair and makeup!

If you’re just looking for some quick tips on what to wear the first time you cross dress then my previous article is the right place for you to start. If you want to look fabulous, and pass as a genetic woman – then read on!

There are seven aspects to looking great and passing as a genetic woman every time:

  1. Wearing clothes that make you look good
  2. Making sure your curves are in the right places
  3. Feminine body movement
  4. Hairstyle that feminizes your face
  5. Natural makeup
  6. A feminine voice
  7. Loving who you are as a woman

Do we want to look like men wearing dresses?

NO! If you’re like me, the image you hold of yourself is as a beautiful movie star, not a guy in drag. The truth is that we can all look and feel beautiful – but it takes some work. Over the next few weeks I’m going to share with you some of the secrets to looking like the woman you see inside – to cross dress for success.

Learn how to crossdress

Learn how to crossdress

If you’re eager to look fabulous today, I highly recommend the World’s Best Cross Dressing Guide. You’ll get all the tips and tricks you need to be the woman you are, and complete your male to female transformation!

Before we get started though, I want to share with you the biggest mistake men make when they wear woman’s clothes. This is probably the number one reason why cross dressers fail to pass, and end up looking like a guy in drag instead of a passable woman.

Before I share it with you, think for a moment on how you picture yourself as a woman. Let me guess, high heels, short skirt, dramatic makeup and plunging neck line. Am I right?

The biggest mistake the transgendered make is that:

When men cross dress they try to look like a whore

Not many woman would be caught dead wearing 6″ heels and a mini-skirt that barely covers their panties. Yet cross dressers try to dress like this – they’re dressing as their own fantasy girl. Take a tip from genetic woman – most of the time they are dressing for their girl friend, or to impress other woman. They are trying to out do other woman, not fulfill a man’s sexual fantasy.

Even if you’re lucky enough to have all the other attributes of a woman, if you dress like a whore you will stand out.

In the first lesson (coming next week), I will teach you how to wear clothes that make you look good, so you can cross dress with confidence.

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About the Author

A woman living in Seattle, enjoying the freedom to be who she is every moment of her life!

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  1. 2 Crossdressing Mistakes We All Make | Crossdresser Heaven | September 2, 2010
  1. conniesissy says:

    any other cds horny enough to get interested in zoo sex like myself?

  2. raleanshot says:

    i feel like a woman traped in a mans body need help to start crosssressing

  3. Anonimus says:

    Hi,i would realy lik 2b name jessica am nt happy to be a man i always dream to b a beautiful cute grl with a big ass,as am from mauritius its hard to lived enclose am nt happy at all,if cn any1 help me am 24 am old ya but want to b a girl thats my dream can any1 help me i always crossdress at nite i even 1d invite my bestfriend to f*** me and it was amazing woah i rembered i always wear panties n bra whch i brought from ebay cn any1 help me please i want to go to usa and become a porn crossdress am i mad or what any help frm u wil be immensely a great help

  4. Lyndsey R says:

    have to have a new face to even pass anything and i have been on hormones for 4 years and am in hell lucky ones get to b ladies we like myself wind up luckily in a grave i gave up everything to b a miss miserable guy loaded on hormones that is trying to be female i will take so many one day i will die happlily ever after seriously dont do it if you are not good looking no matter what

  5. Kacie says:

    Ii have recently started CD and need more advice. Since I am younger than most and my actual nme is Kacie but spelled differently. I hoped to get support so I can talk more about my feelngs with this situation.

  6. Kacie says:

    Hi I want to say how much i love reading these comments, keep them coming.

  7. ilikecrossers says:

    hey conniesissy i am intrested email me at Nickcitrowske1988@hotmail.com

  8. nicole says:

    connie can we chat? i like zoo sex and crossdressing

  9. tiamarie says:


  10. John says:

    I like to get
    help in dressing up,,as a weman,,,where is there a place for me in Ca,,,thanks

  11. sophie doyle says:

    i crossdress to just fit in with my family as both my mums and my three sisters think i should have been a women and have always dressed me in girls clothes, and called me sophie.

  12. Vanessa Law says:

    Hey Sophie, thanks for stopping by – welcome. That’s an interesting way to start crossdressing, one I’ve rarely heard. Do you know why your mom and sisters thought you should’ve been a woman? Do you resent this, or has it been a blessing in your life so far?

  13. Jessy says:

    I started to crossdressing when i was 12 yrs. (now I’m 42) with my sister’s bra and panty. Now i buy my own woman’s clothing including Bra, panties, wig, cosmetics and shoes too. But im a secret CD never done in public. Every night I have been dressing in female clothes and sleep with it, for years and the feeling is fantastic. Now im very desire to going out but no company and shy. Im never been friends to other CD’s. I’m planning to A holiday to abroad, and going out to public as a woman, what sould i do. I need help.

  14. Justin says:

    Jerry I myself am like you I started when i was seven starting wearing my sisters clean bras and underwear they felt great and for a long time turned me on a great deal im 21 now and the urges to be a woman are even stronger ive always known i was meant to be a woman and have dreamed alot about it. I too am starting to look more into going out into public dressed as a female starting suttely by wearing womens clothes under my own or thick hoodies and pajama pants to cover my bra and longer tops as well as my yoga pants which i have quite a liking for. I neither have company to go out with nor really the support from any girls or guys in town and has become kind of lonely. In time though I can tell you we both will be able to go out happily dressed the way we want to feel and dress.
    Happy trails

  15. Ragina says:

    Hi Justin, I’m Ragina. Just a suggestion to you about going out dressed. Why not just go for it and go out all dressed up. I know that it can be a very scary thing to do at first, you need to build your confidence. Try to go out at night for a while when there are few people around and just walk around your neighborhood. If you have a dog that needs to walk, why not use that time to your advantage. Get dressed and go. then, after you get used to being out, move it up a bit. You’ll be surprised at what can happen. The biggest part of being out is to be confident in yourself. Stand strait, look like you belong there and don’t be afraid to meet people’s look and smile . You’ll feel better and more people will not bother you. And if someone does try to “out” you, be nice to them and not defensive. You never know, you may even make a new friend or two. Good luck. Stay safe, be pretty and be yourself. Let us know how it goes.

  16. Justin says:

    hey Ragina thanks for the advice and vote of confidence I just have a hard time building that confidence cause i know as soon as someone meets my eyes they will know im a man still and I cant do much about it until i get some facial features changed eyebrows waxed make up done right and so on and so fourth my shadow of my beard always shows and its just hard to really be a woman at this stage i need my ears pierced with some nice earings to go with. maybe some colored contacts or something idk im just worried about meeting peoples eyes i have gone out but not far just had enough courage to walk from my front door to the front of the house and into the garage but thats about it. I want to go out but i just know my facial loks right now arent to standard to even pass as a woman with a wig on and a full cute outfit its quite unnerving im working on telling my parents and seeing the doctors thursday about hormones to try and start growing breasts naturally and try to get some hips

  17. Ragina says:

    Hi again. I can relate about the confidence issue. The first time I went out dressed was several years ago. I worked in construction and the big boss would let me use his camper trailer at the yard when we were out of town as security. I’d be in bra and some makeup and would take my time checking the area. I loved it. Be patient dear and it will come to you soon enough.

  18. Steve says:

    I have been a secret crossdresser for 35 years – until I met my wife (8 years ago) – this had been between myself and my maker.
    To start with, my wife accepted my “hobby”, even buying me clothes – but soon after we were married – she threw everything out and left me bereft of any clothes – Recently, she has become more accepting and once more – I am “allowed” to wear female clothes as long as she doesn’t have to participate or even see me wearing them
    Any advice welcome

  19. redchaturtle says:

    Hi Steve. I'm currious why she would be OK with it and even buy you the clothes in the beginning then all of a sudden she didn't want anything to do with it. Did something happen? Was there more to your story than mentioned? I have a BF that was a secret CD for 34 years until he met me. I had bought him everything he needed to be a woman. From clothes and undergarments to makeup. Even down to scented lotions and womens deodorant. The only reason I would ever think his need for this was unaceptable is if he took it too far without my knowledge by going outside of our bedroom. Or by possibly competing with my femininity.

  20. why don t you meet other T girl s or cross dressers then you can go out with them ( see if you can get changed at there s)….have your night out then change back to male roll, that way your wife won t mind……..

  21. Naomi says:

    hi redchaturtle
    you dont say if your male or female and if your female then you really have no idea how your friend is feeling
    he should be able to compete with you as an equal and not to compete with you as a male dressed as a female against a female proper so to speak
    let him out of the bedroom it is his right to show as much of his femme side as he feels he needs to do otherwise he will you say he was a secret CD for 34 years he still is if you keep him trapped in his bedroom
    if you love someone let them fly if the love is true they will fly back to you
    teach him to dress and make up it will give him hope that you may repent and allow him to go out dressed
    try it with him one night and see how few people even give him a glance he will be a good age now so people tend to look less at older women that are dressed quite subtle
    be aware of his feelings and not just your own and dont be scared of him being more feminine than you are xx

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