Learn to Crossdress in 19 Steps

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.

If you’re eager to look fabulous today, I highly recommend Lucille’s Stepping Out Secrets. You’ll get all the tips and tricks you need to be the woman you are, and complete your male to female transformation! I used Lucille’s resources when I completed my transition many years ago, and she is the real thing!

Learn How to Crossdress

Learn How to Crossdress and Step Out

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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Dedicated to creating a safe, supportive and welcoming environment for everyone in the transgender community.
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  1. Charles Watkins 3 weeks ago

    I’m 54 years old man and I have been wanting to dress up as a woman. Do not know how. I do have my shoe size. I Have been using natural breast enhancements since 2014. Not a quick way. I’m a 42/A bra size. I know nothing more. Makeup, dress size, pants, I’m 220 pounds and a belly and I am 5ft.11

  2. Denise 1 month ago

    I have been cd for2 years now mainly in doors with my fiancée approval and encouragement , she even buys me the clothes to wear, recently I have started to go for walks late at night and I have to say I find it a great turn on knowing people are watching me dressed in shortish skirt see through top and semi high heel boots, my latest venture was when we had a naughty night away I went to a club dressed up while my fiancée watched in the background, I’m 55 and she is 34, so if I can do it anyone can, basically what I’m saying is if you want to cd just go for it you won’t regret it.

  3. Meagan 6 months ago

    Ugh… When I read statements like this, “Not many woman would be caught dead wearing 6″ heels and a mini-skirt that barely covers their panties.” It does become quite apparent that our community is very divided and is the reason why we’ll always be the outcasts in the LGBTQ community, not to mention being outcasts within our own community. I can go out any weekday to the city and see 50-60 women dress just as scandalous if not more so within an hour and if it’s a Friday or Saturday than easily 100’s of women dressed like that. Since when has dressing sexy and to be a tease make you a whore? Tell any GG that they dress like a whore and see how fast you end up getting into a fight with them. If anything, it tends to be women who can’t pull off the look that refer to those that can as whores or sluts because of jealousy…

  4. Profile photo of michaela jane
    michaela jane 7 months ago

    As a closet and frustrated crossdresser, not able to indulge fully, I have to say that yes, I look like a man in a dress. I have never tried to look convincing but I certainly stay away from high heels and what they like to call “sissy” clothing. Apart from anything else, I know I would look stupid in that kind of attire. I am almost 70yrs old and certainly choose understated clothing such as a black dress, denim dress, feminine trousers or skirt and tops at home. Yes, I wear panties and tights (pantyhose) all the time under my normal male clothes, stockings with suspenders sometimes. The key to my enjoyment is the clothes themselves, not how I think I will look in them, and “can I get away with this in public?” If the answer is yes, then I wear it. some styles of jeans and other pants are ultimately wearable in public. If a person enjoys crossdressing, even a little bit, he/she should not be put off by being expected to be convincing.

  5. marcella 10 months ago

    i have read all comments on this site. i for one have been cross dressing for years behind closed doors and have never stepped outside as a woman. i feel as a woman trapped in a mans body. i want that experience too walk outside as a passable woman goto a club etc. i have been doing this since i was 7 years old but want too go out with confidence. my makeup skills are not the best i feel like i have 2 left hands lol..

  6. Profile photo of Patty Phose
    Patty Phose 1 year ago

    The first time I cross dressed fully when I was 18 for a Halloween Party. Yes I was dressed excessively sexy in a very short dress and very high heels but that’s the look I was seeking.

    Maybe I was trying to be my fantasy girl but I had a great time and won “sexiest costume” and “best legs”.

    Now many years later I have toned my look down somewhat especially when I go out.

  7. evette 1 year ago

    Hi I am evette

  8. Jack 2 years ago

    I want to crossdress but I’m scared to find out what others will think

  9. Lyndsey Rush 2 years ago

    You can try to look younger than 49 but I mean this stop fantisizing and act your age look how 40 year old women dress act and behave you want to blend in my friend not look like a clown— I am over 60 and stuff I wear are tunics tight shiny legging and my hair is naturally blond and long w/out extensions but if you must do the hair (its a bitch to keep up) and use common sense makeup or you will get comments from other women that will make you want to hide— believe me Ive been there and done that so observe observe and be stylish it looks and feels great and gets great compliments from other women and men too!!! a boob job may help too!

  10. Jennifer205 2 years ago

    HI Vanessa, I’m a 49yr. old male and new to this site. I am writing because i need some advice on crossdressing. I want to look and dress like a young girl of about 12 or 13. I have obtained some girls clothing from stores such as Macy’s, JC Penny, H&M, Sears, Old Navy, and Justice for girls. I do not have a problem shopping and purchasing girls clothing. I am having a slight problem purchasing girls panties and under shirts or bras. I am able to fit into a girls size 16, or size xl. The reason I’m writing is because I seem to have a problem with making myself look like a young girl. I mean applying make-up and getting a wig or putting hair extensions in my hair as it is short and I have grayish hair. I could use some real words of encouragement. I want to go through with this and maybe achieve my goal of going out in public looking like a young girl. Thank you for any help you could provide to me. I look forward to hearing from you soon. Thanks again.
    Jennifer205

  11. Patty Phose 2 years ago

    Years ago, when I dressed up, I wanted to look like a whore. I was young and it was my look. Now I want to look good and wear appropriate attire and makeup for what I’m doing.

  12. danny 2 years ago

    this site is brilliant my ex boyfriend put me down horrible relationship but am proud of who i am love lingerieand toys to

  13. John 3 years ago

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

  14. tiamarie 3 years ago

    LOOKING FOR A CROSSDRESSERS ON LONG ISLAND NEW YORK FOR A GIRL DAY OUT LOVE TO SHOP VICTORIAS SECERT HAS STORE IN CITY 2FLORRS THEN GO TO A CLUP DANCING AND WHAT EVER SHE WANTS TO DO

  15. Kacie 4 years ago

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

  16. Kacie 4 years ago

    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.

    • Profile photo of Tissy
      Tissy 1 year ago

      Join up and start chatting with us and we’ll do what we can to help.

  17. Lyndsey R 4 years ago

    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

    • James 1 year ago

      Ahh chin up bird, sucks to hear. Just meet the right cd and you’ll be right, thinking of you

  18. Anonimus 4 years ago

    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

  19. Christa 4 years ago

    Connie email me schris711gmail , let’s chat

  20. raleanshot 5 years ago

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

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