Learn to Crossdress in 19 Steps

Here is a Blast from the past from our site owner, Vanessa. Published originally on March 3, 2008


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:

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  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.


More Articles by Vanessa Law

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Lyndsey Rush
Lyndsey Rush
9 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… Read more »

Woodworking Project Plans
Woodworking Project Plans
13 years ago

Those of us who are living the hellish existance of a TS night find the slutty exhibitionists offensive.

8 years ago

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

8 years ago

Hi I am evette

Patty Phose
Famed Member
8 years 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 years 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..

Michaela Jane
Active Member
7 years 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… Read more »

7 years 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… Read more »

7 years 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… Read more »

Charles Watkins
Charles Watkins
7 years 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

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