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:
- Wearing clothes that make you look good
- Making sure your curves are in the right places
- Feminine body movement
- Hairstyle that feminizes your face
- Natural makeup
- A feminine voice
- 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 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.
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 I started to take pictures of myself crossdressing. Seeing myself as a female I thought I looked sexy and myself I would try to pick up a girl like that. I put up several profiles and did I ever get the comments. I love to stand out but to attract men. I love woman to look at me and find there are a lot of woman do and envy me because they can’t look as sexy as me
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 I started to take pictures of myself crossdressing. Seeing myself as a female I thought I looked sexy and myself I would try to pick up a girl like that. I put up several profiles and did I ever get the comments. I love to stand out but to attract men. I love woman to look at me and find there are a lot of woman do and envy me because they can’t look as sexy as me
need to know how to hide my penis and genitals between my legs so i look more natural
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.
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.
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 BLENDED IN AS A GIRL TAKING A WALK. I NEVER THOUGHT THAT I WAS VERY PASSABLE BUT NOBODY PAID ANY MORE ATTENTION THAN IF I WERE A GUY TAKING A WALK IN THE PARK.. THE MORE I DID THIS THE MORE RELAXED I BECAME WITH MYSELF, MORE OR LESS I DIDN’T CARE WHAT OTHERS THOUGHT. I PRETTY MUCH DRESS ENFEM ALL THE TIME NOW AND THINK NOTHING OF DRIVING TO THE STORE AS A WOMAN. NOW I DON’T GO TO PLACES WHO KNOW ME OR MY VEHICLE WHEN I’M DRESSED. I LOVE IT WALKING THROUGH STORES SHOPPING AND BEING MY FEMININE SELF. HECK I SEE WOMAN WHO DON’T COME CLOSE TO LOOKING AS SEXY AS I DO. I EVEN SEE WOMAN STARING AT ME. NOT AS THERE SEEING A MAN DRESSED IN DRAG. WHEN I CATCH THEM AND EYES MEET. THEY USUALLY SMILE. SOME EVEN SAY I LOVE YOUR OUT FIT OR YOU LOOK VERY PRETTY. I’VE EVEN HAD COMPLIMENTS ON MY SEXY LEGS. A WOMAN SAID I WISH I HAD LEGS & AN ASS LIKE THAT TO WEAR SHORT SKIRTS LIKE YOUR WEARING….. JUST GO FOR IT JUSTIN AND GOOD LUCK
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 Rep is very cooperative as she has both my wife & I as patrons.
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.
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?
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.
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
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.
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
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.
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
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.
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