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.

EnFemme

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Sexiesherri814
Sexiesherri814
13 years ago

I’ve been crossdressing since I was fourteen. I must admit that I am very turned on allowing a woman know and see me dressed as a female and infact I really love to put a womans clothes on in front of them as they are taking them off. I have to admit I love to dress like a little whore and show off as much as possible. I have been doing this so long I have become very good at making myself passable as a female. I use to think I didn’t look good enough to play the part until… Read more »

mike
mike
12 years ago

need to know how to hide my penis and genitals between my legs so i look more natural

Tammy
Tammy
12 years ago

I just enjoy dressing up I’ve used wigs, I’ve put on makeup I still feel and look like me in a covered up way and I see it. So I have tried to change into that woman but to me it don’t work.

SHERRI
SHERRI
12 years ago

HELLO JUSTIN, I MUST AGREE WITH RAGINA,JUST GO FOR IT. I STARTED CROSSDRESSING WHEN I WAS FOURTEEN. THE MORE I DID IT THE MORE I WANTED TO ACTUALLY DRESS AS A TOTAL FEMALE AND LOOK LIKE I WAS REAL. AS I GOT OLDER AND OUT ON MY OWN I HAD MORE PRIVACY TO DRESS COMPLETELY. I WATCHED ALL MY GIRLFRIENDS PUTTING ON THERE MAKE UP AND PAID CLOSE ATTENTION TO THE CLOTHES THEY WOULD WEAR. HOW THEY FIXED THERE HAIR. LOTS OF TIME IN THE EVENING I’D DRESS AND TAKE A DRIVE TO THE PARK. JUST DARK ENOUGH THAT I… Read more »

Joseph Nolan
Joseph Nolan
12 years ago

I’m a 74 yr old married CD and have a Counselor who advises me on how to crossdress. She told me that most CDs do look like whores and are jailbait. My wife takes the same sizes as I so it works like a charm. Of course she has breasts & I don’t. Whe we do catalog shopping (Blair) we try to select fashions that complement each other. I’m planning to purchase a wig next. Being retired on a low income I can’t afford the Breast Form Store but wish I could. My makeup is purchased from Avon and my… Read more »

Roxy Rocks
Roxy Rocks
12 years ago

I have been dressing since I was 5 or 6. I now dress with my wife. We both love the glamour and fun it provides. I love being a woman. I pass very well and have no problem wearing just about anything anywhere. With 12 wigs I can be anyone I wish to be and my wife likes to pick out who she wants me to be so it a lot of fun. LOVE being fem!

babli
babli
12 years ago
Reply to  Roxy Rocks

hi

Ricky Morgan
Ricky Morgan
12 years ago

Okay since I was 4 years old I have always known that even though God is The Ultimate Creator that something went horribly wrong during my process of production! I ended up having a boy’s body but knew deep in my heart I was a girl and was dying to get out. I began dressing from that point on very cautiously mind you. I was raised in a very strict Christian home where this was unheard of and there was no explaination for it at all. Now I am nearly 30 and in the last year I have had a… Read more »

Tammy
Tammy
12 years ago

First of all I’m a crossdresser I’m 62 years old I ware a shot skirt but just above my knees. I dress in the fad. I dress just like the wemon of today. I think that all dressers should be that way. I think the dressers that dress in short skirts are looking for sex and they are like whores I would never dress like that.

Tammy

Matt
Matt
12 years ago

hey so i have always been gay and now want to be a woman. I’m in my twenties and good-looking enough to pull it off, and I am not that tall of a guy 5’8, I don’t grow much facial hair, and I am not fat. Considering these facts,I wish I had breasts and more hips and looked more fem. I want to start off by crossdressing and buying skirts and makeup and underwear and a wig and all other other stuff u need. I am so afraid to go into a store and buy this stuff cuz I don’t… Read more »

Ricky Morgan
Ricky Morgan
12 years ago
Reply to  Matt

Hi Matt !

Good question honey and I have the answer for you! Go to crossdresser.com and there you will find everything you are looking for congratulations on realizing you femininity! I am so happy for you!

SMITH
SMITH
12 years ago

i am a crossdresser, i woul like to take pics as nude, which i wants show big boobs, looks like original boobs,how to keep hips like a woman, pl send message to nail

Sara
Sara
11 years ago
Reply to  SMITH

hi smith
I have the same question…..I am living in a place where crossdressing is not acceptable but I love to CD.

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