7 Essential Tips to Crossdressing

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.

91 comments

  1. Troy 24 April, 2015 at 11:21 Reply

    I want to meet other crossdressers lick me I want to understand myself more ples if thaers anyone that wants to maybe met echother and make friends kind a like a support group ples call me my # is 518 727 7855 my nam is Troy I live in Voorheesville New York 16 Pine St. just outside of Guilderland I jost won’t to mack some frends that are going through the same thing as me !!!!! I don’t get much of a chance to cross dress in public but I like married life too I like my masculine and feminine side but ples i’m trying to put a crossdresing support group together call me 518 727 7855

  2. Lyndsey Rush 23 April, 2015 at 10:18 Reply

    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!

  3. Jennifer205 22 April, 2015 at 17:53 Reply

    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

  4. Patty Phose 12 April, 2015 at 13:34 Reply

    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.

  5. danny 6 April, 2015 at 17:58 Reply

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

  6. tiamarie 4 May, 2014 at 12:05 Reply

    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

  7. Kacie 11 April, 2013 at 19:05 Reply

    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.

  8. Lyndsey R 6 April, 2013 at 20:12 Reply

    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

  9. Anonimus 6 April, 2013 at 01:05 Reply

    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

  10. maya 24 November, 2012 at 21:49 Reply

    am a student in college, i feel like a girl more than a boy, i want to crossdress in puplic but my culture prevents me doing this , i use yahoo massenger to express my attitude being a crossdresser,

  11. divya 17 September, 2012 at 19:50 Reply

    I, myself Divya is a secrare crossdresser. My problem is that I donot get time to make progress to be female becouse every time my family members around me. I always dream about this . Please help me.

  12. mdlrchambers 16 September, 2012 at 11:24 Reply

    I live in milwaukee wisconson and i whant to finde a like minded friend so that i can be myself around them and not be judged if anyone knows whear i can go to meet another person like myself pleas let me know mdlrchambers@live.com

  13. steve 16 September, 2012 at 03:26 Reply

    I have allways wanted to crossdress ever since i was fourteen looking at those older teen girls in a sears catalog all dressed up in short skirts nude hosery and heels as tme went by going to work on the bus feeling shitty wishing i could go home and sleep reading the news paper nothing but bad news skipping to the sports my favourete teams are losing every thing is bad news i go to the comics and even they don’t make me laugh when i get to the blondie comic strip and see mrs. blondie bumstead all dolled up in a short skirt and heels and i think well at least blondie looks pretty today. Wishing now on halloween night i could be a beautiful woman all dolled up in a short lined skirt nude hosery and heels clicking down the street feeling femenie as my breasts jiggle a little until i meet a beautiful lesbian who knows i’m only a woman for one night and knowing only a woman knows how too be pleased makes me climax and when we depart as i click away i say thank you and she says you will be thanking me tomorow bye… and i go home and pass out waking up the next day thinking i’m back to my normal self when i wake up feeling femenine noticing thease bumps on my chest are still there flinging my bed sheet to one side swinging over standing in heels looking down thinking shit! i’m still a chick i walk into bathroom looking in the mirror up and down with my hands on my hips saying in my girly voice that lesbian played a dirty trick on me now i’m stuck this way for twentyfour hours if i climax it’s forever then i go back to my bedroom open the closet and see a hole new wordrobe of womens clothing thinking well i could dress up a little and step out when i ….

  14. mdlrchambers 15 September, 2012 at 17:02 Reply

    I am a 26 year old and i whant to be a girl whean i was 6 i knew i whanted to be a girl and whean i was a teen i had everything i needed to be a girl whean i was in my room at nite by myself whean my dad found my stuff he beet me and told me he would not have a fag in the family i turned to drugs becus of this just so i would have a excuse to dress up and be me that lead to a 5year incarseration and now that im free im terafied to be who i whant to be i live in a unfriendly inviroment and i am terafied i just whant to be me and i have no friends or suport to stand behinde me i fill so alone and afraed i hate my life becus of this all ive ever whanted is to me and i alwayes have to hide the true me

  15. Lyndsey R 29 July, 2012 at 06:24 Reply

    I have to get rid of my deep voice my belly fat and have been on hormones for 4 years. I am afraid to go out in public in a dress but I really want to express myself sometimes. I wear women’s underwear, jeans and tops and have real long hair and little makeup but still feel like i am in drag. I absolutely hate men’s clothing and their attitudes and won’t do them. For me it’s not about the dress its about the way i feel and boy do I get talked to like go back the way you were and forget about it and so on I am 57 and would rather die than live a life of a man which i could never do in the first place. I am just afraid of this damn real life test crap and want to be my own female not someone else s version of one. I am an individual and am not some gal who fits the mold. I am going to get ffs and maybe then can chuck this face and pass as a female which I already do in jeans. I have a real battle on my hands and a therapist may just add fuel to the fire, I am still looking for answers and would really not mind living in my house for the rest of my life if that is what it took to wear what I want and act the way I am a transsexual female that does not fit the pigeonhole.

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  17. zythe 9 April, 2012 at 00:31 Reply

    umm.. hey. i am 13 and i dont know about stuff so… im just going through puberty and im having bits of urges to put on nail polishes and female clothing but im not sure. i want to stay a guy but i have conflicting emotions. i dont know what i should do. so far ive stayed away from the clothing but i wanna know. shoud i CD or stay like this. i want an answer that isnt bias ex. “yes! ive had lots of pleasure and its soo fun!you shoud CD!” i want a proper anser!

    • Chuck Cargo 10 June, 2012 at 13:25 Reply

      You need to talk to a professional—guidance counselor or close family member. Stay off the web at your age, a lot of nuts looking for victims…GOOD LUCK!

    • Anita 22 October, 2012 at 17:57 Reply

      Crossdressing doesn’t necessarily mean you don’t want to be a guy. There are a lot of straight men comfortable in their own bodies who just want to wear women’s clothing. My boyfriend’s one example. He loves dresses and skirts and wants to wear them, but it’s an urge that has nothing to do with his sexuality. I agree with Chuck, you should talk to someone about it. It’s best to look for someone who’s had these urges before. Good luck with everything. =)

  18. SMITH 5 April, 2012 at 09:57 Reply

    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 20 May, 2012 at 14:51 Reply

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

  19. Matt 29 March, 2012 at 02:15 Reply

    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 know how it would look. Any suggestions? And where can u get a good wig?

    • Ricky Morgan 29 March, 2012 at 08:14 Reply

      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!

  20. Tammy 23 March, 2012 at 10:28 Reply

    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

  21. Ricky Morgan 1 March, 2012 at 01:47 Reply

    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 rough go with things. I first came out as being a gay drag queen simply because I was not savvy to this whole new world I am in. BTW Im still stuck in this crap body! I hate being a male and hate having male attributes such as a deep voice and male parts! I lost my job as a Corrections Officer due to my posting of my sexuality on facebook where some of my co-workers began making comments and eventually within a few days rumors that ultimately led to my dismissal. I did not realise that it wasn’t that I was a gay male (even though I had been involved with me previously as well as women) but that I was in fact transgendered and didn’t know the terminology. Now am I a gay female inside? Yes I fully know that and am very comfortable saying that. However not many women are comfortable with that knowledge and tend to look at me as though I’m a bit of a freak. Let me explain what happened. While being produced my biological mother did her best to rid herself of me while still in the whomb. She did any drug she could and drank like a fish. She even at one point tried removing me with a coathanger through means of self insertion into the birth canal but ultimately failed! However due to all the chemical toxins now seeping into my unborn self some of the cells that make up physical characteristics got jumbled up and ended up making a boy! However God had intended for me to be a female and gave me the spirit and energy of one, but of course as always man screwed that up too! Anyway long story short I’m sick of this life and I need to know what I can do to change this about me. People see me as a man and I am not a man I am a woman and I will be seen and heard and loved by someone. I just to need to know where to start cos I look a little goofy when girlfriends try doing my makeup or when I dress when I’m alone I am uncomfortable because I don’t think the clothes look good on me. Any suggestions?

  22. Roxy Rocks 24 February, 2012 at 16:28 Reply

    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!

  23. Joseph Nolan 13 January, 2012 at 21:21 Reply

    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.

  24. SHERRI 7 January, 2012 at 07:41 Reply

    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

  25. Tammy 21 December, 2011 at 14:06 Reply

    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.

  26. Sexiesherri814 29 December, 2010 at 02:50 Reply

    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

  27. Sexiesherri814 29 December, 2010 at 09:50 Reply

    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

  28. Vanessa L 2 May, 2010 at 05:27 Reply

    Carol,

    I don’t think your characterization of crossdressers is fair or warranted. It’s true that many crossdressers dress inappropriately – perhaps fueled by a mistaken male perception of what makes a woman look good. However we are all on our own journey, and would do well not to judge others too harshly.

    I’m sorry that your experience of being transsexual is difficult. For many it is a hard road.

    Perhaps by being more accepting of others you’ll find that others are more accepting of you.

    • Carol 2 May, 2010 at 12:12 Reply

      If you read my comments they reflect upon crossdressers who look like whores. NOT all crossdressers, as the fetishists and deviates are the culprits. Not all crossdressers. Not all crossdressers, is that clear?!!! I was screener for several years of a crossdressing support group back years ago. It was my job to direct peoples inquire, and weed out undesireables from our meetings. I thought I did a pretty good job, until I noticed some members dressed like trash, wearing provotive attire, obvious fetishists, who didnt hide the fact in their actions or in their subject of conversation. We had comments about THEM, and frankly I thought I had done a good job screening, but was fooled. It turns out that they were having orgies in the motel back of our support group meeting place. If it looks like a whore, if it talks like a whore, its likely a fetishist, or pervert, as this is not mainstream crossdresser behavior. These folks are not crossdressers, but perverts who use their bizarre desire for erotic clothing for their own satisfaction. This is not satisfying their desire to wear what a woman would wear to look good, but to wear that gets them their thrills. Only a few do this, but people strike an opinion easily, so not only first, but all impressions are important. I discourage these fetishists being caloled cross dressers, as theyre a different mold. If anyone mis understood, so sorry. Carol

  29. Carol 2 May, 2010 at 01:30 Reply

    Having re read my post above about why crossdressers look like whores, is what I feel to be essentially true. Those of us who are living the hellish existance of a TS night find the slutty exhibitionists offensive. I wouldnt wish being a TS on my worst enemy. Life is tough enough without having to watch the circus of whores come to town. Now lets get on with it.

    • Carol 2 May, 2010 at 08:42 Reply

      Hi Van: I did not put that paragraph in perspective. I was referring to the statement on the site asking why SOME crossdressers want to look like whores. I was out of line if you or anyone else thought I had all crossdressers dumped into that lewd catagory. With the road of a TS being a hard road, your dam sure it is. hasent it been for you? I wouldnt wish such a thing on anyone. I missed the potential of my youth when I couldnt live in my true gender. That was unhappy, along with other defeats, that go with life. Now that Im in transition, I frankly have been joyous and never felt better about myself. Different strokes for different folks is fine, but Ive always been offended by those who obviously dress like a slut for the sex and turn ons associated with it by a very few. I was screener for a support group years ago, and though I tried my best to weed the garden so to say of who got to go to meetings, I thought i was a pretty good judge of callers. only to find out later that several of the members, the eroticly dressed ones, were having orgies in the motel room in back after the meetings. That hasent worn off. If I offended anyone, thats my fault and it was not intentional. I did not proof read my note before putting it on. Now someone help me up out of the mud! Love Carol

      • Vanessa L 2 May, 2010 at 15:23 Reply

        Yikes, that’s quite a story – it’s hard to believe that things like that would go on. No worries love, we all say things which can be interpreted differently by others.

        I’m just at the beginning of my ts road. You could say I’m still packing the car for the trip, so I don’t think my perspective is… rich enough yet to comment with authority about the road to womanhood.

        Hugs,
        Vanessa

  30. Carol 1 May, 2010 at 16:20 Reply

    Hexiva. Having known a number of TS female to male types, Id say just dress like the guys do, jeans, and a loose t shirt, to cover your hips if you can get away with it. Cut your nails short. Wear short hair, dont over do it, but if you do get read, nobody cares, as there a lot of girls that cannot pass for their own gender, save their voice!

  31. lakshmi 3 April, 2010 at 10:19 Reply

    im a college going student i cant express my fem side since i dont have any sisters to try their clothes. i have bought only a bra and panty with my pocket money …. im so upset by this and what shall i do. . .

    • Eli Quin (TG) 20 July, 2010 at 01:50 Reply

      go to Goodwill store (try anything you find right there, the personal are friendly to all CDs), or go to Salvation Army store. Used is as good as new, but way cheaper!

      For boobs, just buy nylons, cut them off, put bird seed (or rice, but classic advice is bird seed) into it, and then make a big knot (that's your nippie!). Try it on, if there's to much, remove some. Don't overdo it! Go for B or C size (choose B). Measure you breast with the bra on and waist, go to JCPenney or Target and see their fit chart. See that you match to a normal size (if not, you probably want to remove some more of that seed, or maybe add a bit)?

      Come out early, while at college – you can achieve much better looks when young and college kids are generally accept queer easier than older folks. Make friends with people who accept you. If unready, seek transgender/lgbt support group (there're in every campus these days). Be truthful to yourself, don't think you'll ever be able to 'stop it'. Otherwise, you'll meet a girl, make babies and 10 years from there, you decide to come out and break the family.

  32. Ragina 27 February, 2010 at 13:48 Reply

    Justin, I’m so happy that you now have the support that you need to begin your transformation. Hang in there, I’m sure that your Dad will come around if you talk to him in a positive way. It’s a real shock to a father when a son has to make such a drastic change in his life such as what you are doing. I don’t have any suggestions as to what to say to your Dad to help him understand why you are doing this, so unless someone else out there can give you some advice…
    Otherwize, My prayers are with you as you start your transition.
    Stay safe, stay beautiful, and be happy. Ragina

    • Vanessa Law 3 April, 2010 at 11:56 Reply

      Hi Lakshmi, The best place to start is to learn a bit more about what you’re feeling, and to find resources either online or at a local library. The books I’ve linked to on Crossdresser Heaven are a great place to start, there are also many other blogs from teenage crossdressers who may give you a more insightful look from their perspective.

      I recommend starting with this article: http://www.crossdresserheaven.com/a-teenage-crossdresser/

  33. Justin 25 February, 2010 at 00:18 Reply

    How did you get to the point that u were confident in looking enough like a woman that u could go out in the day time and still be able to meet peoples eyes and smile as u walk a busy street and deal with all the eyes u know are on you or think are on you? What do you do for work now? Have you grown breasts or had implants? Are you pre-op? I know I do want the reassignment surgery but in time. I dontw ant to get implants id rather grow them but im worried about the dangers of taking estrogen….

    • Ragina 25 February, 2010 at 17:36 Reply

      Hi! As far as the confidence issue goes, that wasn’t much of a problem as I’m rather outgoing to begin with. The looks came courtesy of my wonderful wife. From the time that she accepted me she has made it her job to see that I know what I’m doing so that I look acceptable.
      Now for me personally. I’m 55 yo, and retired on disability. I am married for 20 years and have 5 children, the youngest is 8 yo. I spent 22 years in the military, including a tour in Iraq.
      As far as your questions, the answer is no to all. I’m just a crossdresser, and plan to keep it at that. I still have to keep a male presence as my youngest just wouldn’t understand, so I keep it on the downlow.
      I hope that this has helped a bit. I don’t really know what else to say other than to take things at your own pace. The confidence will come with practice, especially the makeup and the look. Develop a look that is completly you and work to perfect it. Don’t expect to be a beauty queen the first time out. A suggestion to you. Adopt a ‘good enough’ approach. Get to a place where you like how you look, then work on the details to perfect the look.All of this will also build the confidence you need to step out as the woman you want to be. I hope this will help. keep me posted as to your progress. Stay safe, stay beautiful and love yourself.

      • Justin 27 February, 2010 at 02:30 Reply

        so i told my parents today and my step sisters my dad is heart broken cause i felt i couldnt go to him about as I was afraid to tell him that he would pop a vein. My step mom is very supportive i hugged her twice tonight and told her i loved her and she loved me she had to fight back the tears each time. My step sisters are so supportive its amazing despite how distant we have been for so many years and todl my step mom hey like we have to support him and my step mom agreed. my step mom and dad talk about it for atleast two hours a night and it’s dad who brings it up each night. I’m gonna talk to dad in person for the first time about it this weekend and im extremely nervous. I need to leave town though to be successfully a woman as the city I live in will not accept this change and I will be in a lot of trouble if I get caught this city is not a nice place for our kind. I am greatly relieved and starting to be more reassured about my endeavor with the feminine life.
        thoughts and advice support????

      • Carol 1 May, 2010 at 16:28 Reply

        The heading of the reason crossdressers dressing to look like a whore, isnt accurate I think anyway. These are fetishists and bizarros who are in a sexual existantial fantasy land. No decent woman would dress like that, and neither would any crossdresser with any scruples. You ARE what you look like. Dont give the rest of the community a bad reputation. You can leave by the back door….. just slide under it on the way out. You get the picture.

  34. nikki 26 October, 2009 at 02:38 Reply

    I love to dress the way the young actresses and models dress,very stylish and sexy outfits and i love the dark makeup,although as i get older i’m getting better with it so i do tone it down a little.I know i would stand out like a sore thumb if i wore this in a shopping centre on a wet Tuesday afternoon,especially with my 5inch high heels on,but as i never leave the house dressed or want to,i’m so happy as i am.My wife is ok with my dressing as long as it dosen’t rule my life,so over the years i’ve settled into a pattern of just once a week,she calls it my little hobby,but she shops with me for my makeup and clothes.

    Hugs
    Nikki

    • Vanessa L 1 November, 2009 at 12:35 Reply

      Nikki, it seems like you’ve settled into a good routine with your wife. I’m happy for you. It’s sometimes hard to find the right balance in a relationship between what the crossdresser wants and what the wife wants.

  35. Sandra 8 September, 2009 at 05:16 Reply

    Hi all. I am relatively new to this, but I have a suggestion for anyone who wants to be able to shave their arms, but like LiSa feels that people will notice the change.
    You could claim to be getting heavily into cycling- cyclists shave for safety reasons. If they fall at speed the hair would otherwise melt with the friction, and remove large patches of skin. It leaves very large scars, so they avoid this by shaving arms and legs. Whether you actually get around to riding is irrelevant.
    Also I have started keeping an eye on women who have broad shoulders, like swimmers, to see what outfits I could get away with wearing.

    • Eli Quin (TG) 20 July, 2010 at 01:53 Reply

      Trust me, no one cares. Don't ask, don't tell. If anyone (usually 'best friend') asks, just tell him you like it this way (or wanted to see how it goes).

  36. LiSa 3 September, 2009 at 06:48 Reply

    hi. i am sorta new to cd. i have always been a closet cd and have never done it in public. i do have very hairy arms and legs (which i cant shave, because i deal with to many people at work). i have finally worked up the nerve to do it in public, what do u suggest to cover up my arms and legs (noting that it is summer and hot out). thank you~lisa

    • Vanessa L 3 September, 2009 at 15:02 Reply

      Phew, you’re in a bit of a bind there hon. In winter there are all sorts of tricks to use (stockings for the legs, long tops for the arms). There are many men who don’t have very much leg or arm hair, and I’m willing to bet many men at your workplace won’t even notice if you didn’t have arm hair. Even more so if you removed the hair gradually. Either way, you need to commit. Don’t let your hair grow half out after shaving – people are more likely to notice this.

      Hugs,
      Vanessa

  37. leona 8 August, 2009 at 10:30 Reply

    Greetings to all.you have said to watch woman my age and style.I do and have learned so much.rihgt now for me the gresatest joy is allowing my dominate fem side to take from my male side those things that can make me undrestanding of who Leona is.slow prosess but one worth the wait.untill next time.Peace to all

  38. Leona 4 August, 2009 at 11:07 Reply

    Greetings to all I’m new to CDH and have read with joy all that I can. I have CD most of my life but tge demands of family and society it was always in private.but now that I’m 56 yrs.old and those demands are mostly gone I desire to become who I have always been on the outside.within has always been there.so can any one please help me with age appropriet tips on fashion and makeup.thanx all. Leona

    • Vanessa L 8 August, 2009 at 09:20 Reply

      Welcome Leona, it’s great that you could join us at Crossdresser Heaven! The best place to start is to watch woman your age. See what they wear. Look at woman who are roughly the same build as you and see what suites them. Some tips apply to woman of any age (such as sunscreen!), check back here often for makeup tips.

  39. Rachel 21 May, 2009 at 20:30 Reply

    You got that one wrong. :-) For one thing, like someone mentioned previously, some of us don’t dress to pass, just because we like the clothes. Nevertheless, when I pictured myself as a woman, I was wearing a bridesmaid gown, bridal gown, or prom dress, or a knee length pleated skirt with modest heels (just a couple of inches), and a pretty blouse — and no stubble, pretty hair, etc.

    Don’t get me wrong, I like your blog, thanks. If anyone out there wants to read my blog, I wouldn’t mind a visitor or two either, LOL.

    MaidMichelle.blogspot.com

  40. Justina 22 January, 2009 at 03:04 Reply

    Do you have any tips for a guy thats 31 years young 6ft 4in weighs 225lbs and has a lot of tatoos. I embrace my manly side as well as my fem side. I already have my style down for my manly side. Now I gotta find a style that best suits me for my fem side. I like the Amy Winehouse look. What do you fabulous people think? Someone please help!

  41. Priscilla Aguirre 20 January, 2009 at 15:24 Reply

    Thanks for the fine advice. Sofisticated, well explained and useful.
    I can´t wait to go in public but have no company. Love to look younger than 60, but…
    I can´t pierce my ears either and love big earrings.
    First time at your website. I´ts fantastic
    Thanks. Keep it up.

    • Vanessa L 21 January, 2009 at 22:11 Reply

      Hey Priscilla, thanks for stopping by, I’m glad you found the website valuable. There are many great clubs all over the country that cater to crossdressers of all ages. I’m staring down at 30 (less than a month to go!), so I guess I can empathize somewhat. I’d love to be 14 and discovering who I was. there are probably things I would have done differently. But I’ve had a blessed journey as who I am, even if I’ve got more wrinkles than I’d like :)

      Hope to see you back soon.

      Hugs,
      Vanessa

  42. Kelly Stevens 29 November, 2008 at 23:06 Reply

    You asked for tips on passing as a woman:
    1. Dress your age. If you aren’t a junior, don’t buy your clothing in the juniors department.
    2. Dress appropriately for the situation. A cocktail dress at the mall isn’t optimum. Make up needs to be appropriate.
    3. Crossdressing is an illusion. A genetic woman can go out without any make up and can look a mess but not look like a man. You can do the same as a man and not look like a woman. You need to constantly preserve the illusion and this involves diverting attention away from your flaws and using clothing and most importantly accessories to preserve the illusion. I do not need glasses but found they feminize me so I bought some (in the women’s section of an eyeglass store). wearing men’s glasses simply is not good enough in 99% of the people I know. I wear a hair band, diamond engagement ring, chain bracelet, necklace, earrings that dangle, and red lipstick because many people have critiqued me and said these things feminize me. The red lipstick and nail polish divert the eyes away from other parts of me.
    4. Choose a wig wisely, This may be among the most important things you do. Length, color, style all matter. (If it is too perfect, it will look fake.)
    5. Hair removal is always an issue. You think nothing of spending a great deal of money on clothing and cosmetics so spend some on a quality razor. Consider hair removal on your face if necessary. I had laser hair removal and it was the best thing I ever did. Use the right foundation to cover the beard but shave it off first! covering is not as good as removing. Shave closely and several times.
    6. Apply make up skillfully.
    7. Cover your arms if you need to. My arms are larger than a woman’s so I wear some type of top. This means I never get to wear sexy cocktail gowns and expect to pass but I can usually find something nice with sleeves. Cover your Navy tatoo!
    8. Keep your skirt length appropriate. In fact, keep everything appropriate. Anything that looks out of the ordinary will be noticed and once you are noticed you will not pass. Much of the time if others really noticed me i would not pass yet somehow I pass extremely well. Why? Because I blend in and fly under their radar.
    9. Avoid direct confrontation with anyone and when it i necessary to interface with a waiter, store clerk, etc. be prepared. When i go to the grocery store i know they will inevitably ask me paper or plastic so I am ready and reach for a plastic bag. I know I will be asked cash or credit so I have my cash or credit card in my hand where they can see it before they ask. But if I have to speak, I speak softly and quietly and smile.In a restaurant, point to the menu item as you order. This reduces the need to fully speak in detail.
    10. Choose where you go in public carefully to minimize problems. If you don’t really pass, stay out of the ladies’ room. I go out at any time of the day or night in Times Square and pass but I avoid groups of teenagers like the plague. They will notice and if they notice they will not notice quietly.
    11. Walk like a woman not a caveman.
    12. Relax. If you are afraid, you will walk like you are afraid. Have confidence.
    13. I’ve seen many men who do not prepare themselves to pass. One CD friends is an auto mechanic and he shows up at support group meetings with black grease on his hands.
    14. Eat and drink like a lady. I love beer but more women drink wine so i drink wine. Men stuff their faces. Women are much more, well, feminine in how they eat. Study female behavior so you can emulate it properly. A word about smoking. I personally feel that smoking is one of the easiest means to tell if someone is a CD or a real woman. Few men can smoke like a woman. You think you can, but you can’t.
    15. Carry a mirror and use it. Men don’t need much attention but women need constant attention. Walking from the parking lot to the Mall can result in blown hair. Eating can alter make up. Be prepared.
    16. Smell like a woman.
    17. Pay attention to detail. You may not be into make up and real women don’t need it to look like a woman but it will really help you. Curl your lashes. (No, don’t use artificial lashes). Keep your clothing stylish. No, that man’s coat isn’t going to pass as a woman’s coat. Details! If you have a huge Adam’s Apple, wear turtle necks. Learn to adapt.
    18. We all want to have our own set of 52 DD tits but if you wear 52DD tits you are going to attract attention and you will therefore be noticed.
    19. Be self aware. Know your limitations. Unless you have practiced dancing like a girl you probably won’t do it like a girl.

    I hope these will help you.
    Kelly Stevens

  43. Vanessa L 29 November, 2008 at 17:00 Reply

    Hi Wendy, thanks for writing. It’s tough when those we love don’t accept this part of us, but I’m happy that you’ve taken some time to express yourself as well. Without this I think we die a slow death inside.

    Hugs,
    Vanessa

  44. Wendy 28 November, 2008 at 11:22 Reply

    Hi

    I have been dressing in female clothes for years and the feeling is fantastic, a nice little black dress, tights, panties, bra, and heels, it is just a pity my wife does not like agree and join in my fun, woman are so lucky in the way they can dress, us men are so bloody drab, I am new to your site and it looks very helpfull will be back.

    Love Wendy

  45. Lynn Jones 26 March, 2008 at 13:51 Reply

    > Am I right?

    One out of four isn’t bad. :-) You got me on the heels, but my feet look like boats in flatties. While I may wear heels, they’re not that high – not those “FMSs” that people keep for the bedroom.

    For what it’s worth, I think you can do a lot worse that taking note of women your age are wearing….

    Note, this won’t work if a) you live on a filmset or b) hang out near a strip joint. Those looks are for the professionals only :)

  46. Anonymous 11 April, 2008 at 17:26 Reply

    You wrote, “think for a moment on how you picture yourself as a woman” but….

    I think you’re forgetting that for some people “cross dressing” just means wearing clothes typically associated with the gender opposite to their own. I don’t dress to pass as a woman, I dress because I enjoy wearing women’s clothes. There’s a big difference between dressing in women’s clothes and trying to look like a woman. But they can both be considered ‘cross dressing’.

    You seem to also be overlooking women crossdressing in men’s clothing. One of my partners does that sometimes, but she does it for a more theatrical effect, not a fetish and not to pass as a man.

    It’s too bad that your outlook on crossdressing is so narrowly focused. You seem to have some good advice, but you seem to be assuming that everyone is just like you. And though I don’t know much about this big ‘ol world, I do know that we’re not all alike.

    Kind regards,
    A

  47. Leah Gray aka creativeblogger 17 April, 2008 at 08:38 Reply

    It’s a funny world we live in when you think of it. I am surrounded by very badly dressed WOMEN every single day. I am thinking that you chaps should be giving them tips 😉

    If you see those programs (in the UK) called ‘what to wear and what not wear’ you’ll get an idea!

    I suppose therefore who you emulate is very important. Emulating the women out and about might actually NOT be a great idea.

    Perhaps find a role model celeb who might match you in build ……….ok forget that, these days those women don’t even look like real women!

    Who to model yourself on?

    Somehow somewhere you need to find a female that matches your build, one with good taste in clothes and try to learn her secret.

    I am thinking these resources might be helpful:

    Catalogs for

    plus size women
    tall women
    petite women

    might actually be fairly helpful?

    Meanwhile here’s an important tip ( I shall use this tip on my blog if you don’t mind Vanessa!!)

    If you are tall and you wear a short skirt with panty hose (tights) they tend to creep down at the gusset and so when seated or even standing the pantyhose come down lower at the crotch than the skirt!! This is not attractive on either sex!

    So my advice

    Keep those skirts nearer the knee than the crotch to avoid this ‘crotch hang’ effect.

    Leah x

  48. sophie doyle 27 December, 2008 at 03:21 Reply

    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.

  49. Vanessa L 28 December, 2008 at 16:19 Reply

    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?

  50. Jessy 4 December, 2009 at 09:48 Reply

    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.

  51. Justin 22 February, 2010 at 14:08 Reply

    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

  52. Ragina 23 February, 2010 at 15:04 Reply

    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.

  53. Justin 24 February, 2010 at 01:03 Reply

    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

  54. Ragina 24 February, 2010 at 22:54 Reply

    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.

  55. Steve 14 April, 2010 at 01:05 Reply

    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

  56. redchaturtle 6 July, 2010 at 22:54 Reply

    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.

  57. Jane Christine 18 March, 2012 at 03:22 Reply

    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……..

  58. Naomi 16 January, 2012 at 00:45 Reply

    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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