Gather the courage to crossdress for the first time

You’ve been telling yourself for weeks that you’re going to do this. Debating with yourself, arguing with yourself, justifying why you didn’t go this weekend. Every time it ends with a promise that next time, next week, next month will be different. Yet somehow things don’t seem to change. You find that wearing your feminine finery at home doesn’t seem to satisfy a deeper longing inside you anymore. For a brief moment you wonder, “Am I cured?” Of course, you already know the answer to that question.

What stops you from crossdressing?

I don’t mean just crossdressing within the safe confines of your own home. I mean going out crossdressed for the first time. I mean gathering up all your self confidence and strutting out the door looking the best you ever have. Boldly going where very few other men have gone before.

Today I’m going to share a few reasons why you might be putting off such an important step, and how you can overcome your barriers to crossdressing.

You have nowhere to go: This is probably the number one reason why people don’t go out crossdressed – because you don’t think that you have anywhere to go, somewhere that is safe, where you won’t be recognized, and someplace that you can enjoy. Just before my transition I used to spend every weekend in a park just round the corner from my house. It was my sanctuary. I was able to be myself for a few hours, enjoy the sunshine with little fear of being outed. It was a safe place for me, and helped me build my confidence to go other places. You might find a local transgender meeting group (also a safe place), or a transgender friendly club or restaurant (your local transgender organization will know of a few) or if you’re fortunate enough – with a group of your friends who are accepting.

What stops you from crossdressing?

What stops you from crossdressing?

You’re afraid: Fear comes in many forms. Fear that you’ll make a fool of yourself, fear that someone will recognize you, fear that you won’t pass and get into trouble. Since I have readers from all over the world it’s worth noting that you should take the time to understand local laws. Generally across the US, Europe and Australia it is not illegal to crossdress. The biggest antidote to fear is experience. Do it a few times and you’ll gain confidence. Spend a few hours en femme and you’ll build the habits and mannerisms that serve you well as you venture further out. Most importantly, start with a place that feels safe to you. Take baby steps.

You look horrific: Honestly sweetie, you don’t look that bad. This is a legitimate worry, since learning to be feminine takes time and practice. Even then many ladies aren’t blessed with the figure to pass there are still things you can do to improve your chances of passing in public. I’ve known many wonderful ladies who didn’t pass, but held their heads high and walked down the street like they belonged. Confidence is the difference between someone pointing and laughing, or someone coming over to chat with you because they find you generally intriguing.

So what stops you from crossdressing?

Hopefully with the few examples I’ve given you, you can see that it’s not the world that stops you from crossdressing, but yourself. Take a moment to think about what’s been holding you back, perhaps this weekend will be different…

Are there other reasons I missed? Please comment and let me know what has held you back, and how you overcame it. This will be a blessing to others just starting out!

P.S. Thank you to all the ladies who responded with their crossdressing success stories! I received them, I’ll reply individually soon. If you’d like to share, please submit your crossdressing success story.

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Dedicated to creating a safe, supportive and welcoming environment for everyone in the transgender community.

Latest posts by Vanessa Law (see all)

  1. Janet 6 years ago

    I was one of the afraid for going out dressed. Fear of being ridiculed or at the time didn’t know what the local laws were. It was 1981 before crossdressers were not out in the public view very often. Eventually dressed and worked up the courage to go to a movie. I know not a lot of exposure. Maybe a minute crossing the lobby into the screening area and back to go out of the theater. I was noticed and no one made any negative remarks. I didn’t attempt to use the women’s restroom until I had been out in public for over a year. I was checked on by the usher the first few times. The usher kept coming into the screening area to see if I was causing any trouble I guess?

    • Author
      Vanessa Law 6 years ago

      Bravo hon! What a brave step back then! I think you were wise to step slowly into the public feminine role!

  2. Johnny 6 years ago

    There are other reassons for being afraid to “go-out”. My personal reason, was being afraid of exposure, but for me it was part of my need for humiliation while being “forced to crossdress”.
    My wife was accepting, and would assist me while dressing as her “sissy”. It was sooo scary to be put out onto a rather dark and lonely residential street, and having to walk to catch up to the car that she would drive away in as soon as I would reach for the car door. I would be dressed up completely with makeup and a wig, but the walk had to be perfectly feminine or she would drive off and leave me there. (the threat of course.)

  3. Judy West 6 years ago

    I am still trying to get enough courage to go out in public and keep putting it off for the reason I might be noticed or get stopped by a cop or I just don’t know if I look good enough like a woman. I want to start out by taking a ride to mail some letters late at night when not too many people are out. I only want someone to look at some of my pictures and tell me what they think of me crossdressed. Please let me know if someone can look at my pictures and I will send some out. Judy West.

    • Janet Wyrock 6 years ago

      Also might check to see if there is a Tri-Ess chapter near you. This is a group for married heterosexual crossdressers. They also encourage wives to attend with their husbands. Most Tri-Ess chapter will also allow single crossdressers. I do not believe that is against the law to drive while appearing female. Obey the traffic laws, make a check that your vehicle is in operating shape, that is headlights, tail lights, turn signals, brake lights and license plate light are working. That will minimize the chance of getting pulled over by the police. Also do not drive after consuming alcohol. If your arrested for DWI you will be placed in the male section of the jail for holding to be bailed out even if you appear as a female. Use common sense in dressing and appearance and you should be able to have a successful outing dressed!
      Good luck.

    • Author
      Vanessa Law 6 years ago

      Good luck hon! There are many communities online that can help, the forum is a great place to start.

  4. Ronda 6 years ago

    Two months ago I started meeting a CD girlfriend at a bar in town that she been going to for about a year. I was very nervous until I had my first margarita and then a second, I finally calmed down. What a rush, after that it seemed that I was accepted by everyone in the bar.
    I am now a member of a TG support group in Sacramento California and attend their monthly social. So get out there and enjoy being the women you want to be, I know, I have.

    • Author
      Vanessa Law 6 years ago

      Congratulations hon! That’s a bold first step!

  5. John/Saundra 6 years ago

    Well like everyone else. I was just a very part time. But scared C/Dresser. I never really got to the full stage at home. I even got Balloon’s for Brest’s now you could Imagine what I must have looked like really some freak. Any way I was on the site called Gaydar one night and I spotted someone, who was to become a very good Friend and yes Later a very good Lover as well. Any way Yes I was invited down to Waterford. Now I come from Tipperary. Yes in Ireland. So I packed i think it was 2 Suite Cases. And a bad or 2 as well and my Vanity Box. Well eventually I finally got to The City of Waterford. And found the Train station.. I asked him how will I know you Well i really should not have Bothered in asking Him at all. I got out of my car and called yet again He said that he was in the station and that he would come out. I said that’s good Well what I really wanted to do was get back into my car and drive away as fast as I could But I was rooted to the Spot as this Mad person was approaching me with His hands Waving and dancing around the Place and There was me Desperately trying to Disappear. and i’m sure I was getting smaller by the second. Anyway he came up to me and wrapped his arms around me and gave me a big Kiss on my Cheek well I nearly Died. Me in Public And being kissed my a male No I thought. Well he got into my car and he was telling me how to get to his place. Well most of the Next House really was a daze to me and Still wanting to get the hell out of this situation that I got my self into.
    So it was now getting a little bit better as my cases was getting slowly strone around the Place. Now he started to explain that the club was on that night Well I think I peed my self with the stark reality of it all.. He could see that I was defnightly Worried about the Whole thing. He just came to me ads wrapped his arm’s around me and said I will look after my little Girl. Well I really don’t know but maybe it was the way that he had said Little Girl. For some reason I was beginning to relax a bit. now for the dressing well he had his own Ideas about that. Well when completed finished and with full makeup as well I was now beginning to look somewhat Like a female. Well now I had come to the Point of no Return. As I was step-in down his stairwell I had so many Mixed Feelings within me I was unable ti think straight at all.. Now as the BIG FRONT Door loomed closer I was looking at Him. Who was now also a very pretty Woman.
    I opened the door and closed it and opened it again Saying out aloud Here Goes Saundra You are now a Woman. As I’m typing this my eyes are blurred as the tears are flowing.
    I have to stop now but I will write another Post on my first Night as Saundra Many Kisses to all

  6. sindee J 6 years ago

    motly my wife’s not willing to accpet me as i do it and lie about it. Not to mention i really don’t ue make up well

  7. Maliika 6 years ago

    A good site!
    Thanks a lot!

  8. Katie 6 years ago

    Acceptance is definitely the primary fear along with the fact that I don’t have a girlish figure – though I do look better in a dress than the wife does (even if I say so myself). My parents were not supportive of my desire for interracial relationships, they would absolutely disown me for this transgression. Then, add the wife into it. I’m not sure how she’d react – then if anything happened between us, I can see the mud flying. So, as much as I’d like to admit to her at least, I can’t even bring just that one person into my secret. I’m sure someday she’ll stumble across my stash, and there will be some explaining to do – and it’s going to suck. But it’s not going to be any worse than if I brought it up another time of my chosing.

  9. Saundra/John 6 years ago

    Firstly as you know I had been out quite a few time but I was chatting to my G/Friend on the Internet and something Slipped out about cloths or something. Then out of the Blue. Carol said are a C/dresser or do you wear Female cloths. Well i was stuck to my chair and said I have to go now. But I Didn’t have to go any where but as I was crying at the fact that she knew. I was So shocked. Well Carol then Phoned me to ask the same question. said that yes I was a c/dresser and was more shocked to hear saying that she would love to see me fully Dressed as Fem. I said that I will get back on line and chat to her some more Which I did. any way Carol was going to visit me here in Ireland in November and wanted me to collect her from the Airport fully dressed. My reply was you must be Mad you don’t know just what you are asking of me. Well when it got to November the weather was very bad but I got a friend from the town which is near me and Francis helped me to get dressed as Yes I did want to look my best as Carol had not seen me dressed before. So all set and ready I set off for the AIRPORT. So FAR so good I was about ten miles from the Airport when I noticed that my fuel was a bit low so I pulled in at a Garage and to my horror I then noticed that I had forgotten my Handbag. But I saw my wallet in the door compartment so I was saved. I got my fuel and went in to pay. Then I was with another problem. I was dressed as w female and had a mans Credit card. So I just braved it out. The assistance Looked at my card and then looked at me. I think what was going through his mind She has a card bet it don’t go through. well you should have seen the Shock on his face when I entered my pin number and passed. I’m sure he is still looking at me. Yes I forgot to mention I had my Black patent 4″ heels on. Back into my car and was off again and got to the Airport safely. I had parked out side the Terminal where I had picked Carol up before. I parked up and went inside and by now Carol had text me saying I’m here but where are you. I replied saying to stay there I’m parked up. Well, inside I had an Idea where carol would have been standing so I went around her and now passed her twice and not a sign of recognition. Then I noticed that she had the phone in her had ready to text me again I stopped in front of her and she looked up and Said can I help you I moved my Glasses up and she nearly went crazy. Saying my God what happened to you. I said does that mean you had no Idea at all as to who I was in front of you. Carol just said you can say that again. My girlfriend Really Loves the way that I dress..



  10. Leah Lynn 6 years ago

    I live in a small town where everyone knows you or at least knows who you are. My wife is not supportive, other than Halloween. A few years ago I dressed for a friend’s birthday party as a prank, that his wife suggested, so I have been in public, but not really as a woman. Last Halloween I was dressed as a normal woman, and a friend thought it was great; he wants to see me as Leah again. I’m planning to attend his birthday party as Leah, and I’ll stay dressed, instead of changing back to male personna.

  11. Kevin 6 years ago

    This site is so helpful in so many ways . Keep up the the good work !!

  12. princess sissy penny 5 years ago

    thanks so much will do

  13. vicky mynx 5 years ago

    Hi there
    Think this is a brilliant page, keep up the good work. i am a part time transvestite/cross-dresser & do go out dressed, but choose where to do it. Also try to get to a tranny night as often as possible in a city not too far away, but can’t always get as is expensive when have to factor in hotel cost. Think Another reason that can hold people back from coming out of the tranny closet if family, worrying what they will think.
    I must admit since I came out of the tranny closet a couple of years ago, people have accepted the new part of me more than I can ever imagined, & I do not regret coming out one bit. I feel so proud to be a cross-dresser, & in actual fact, think in some circumstances people have warmed to me more, especially may be the ones that, thought I was a bit more serious, especially since I currently work in security & used to be a doorman. Granted though the women seem to accept this part of me more than the fellas, but even my male mates while shocked & surprised, they are ok even if still have a laugh every now 7 again which is OK!
    Keep up the good work, let us in this community keep educating the wider world of this life style/gender.

  14. vicky mynx 5 years ago

    To previous reply, we men who cross-dress do so primarily because we like women clothes, & there is usually a hook. for me the hook was High Heel shoes, which I discovered at around age 11 or 12, when looking threw my mums catalogue. I don’t feel that women should have anything to worry about, if their man reveals to be a cross-dresser/transvestite (different words for the same thing)as this does not mean that he is gay. If anything, I think that its makes us more Heterosexual in a way cus another part of this world, is that we tranny’s often admire women & not just their clothes. The way you women move walk & talk & look, so much so we want to emulate it. Its almost like for me anyway, getting up close & personal with your girlfriend/wife is not enough, & you want to experience what its like to be a woman for yourself with out having a sex change, cus thats a whole other board game, but at the same time they are some things you don’t want to experience as a cross-dresser, if you are straight anyway. Like in all other walks of life & sub cultures, you get a variety of different people, & while they may be a few from the rain mack brigade, most tranny’s from my experience are just regular guys, that like to dress up occasionally or some time full time. Remember there is a difference between Transsexual & Transvestite, as transvestite Is just another name for Cross-dresser & transsexual is some who has had sex change for various reasons & not always cus fee as though born in wrong body, as i know of a transsexual who just felt more at ease acting femme & always got treated as such so with his parents support he eventually had re-assignment surgery.

    So come on girls if your man tells you that he wishes to partake in this way of life, don’t be freaked out, cus some where down the line some female role model may be inspired him rather than Arnold Schwarzenegger, and that person who inspired him may even be you!

  15. Saundra P Ryan 5 years ago

    I was very Pleased to read your Story Leah And for one i would Love to meet up with you for Coffee and chat as i admire any one who can take that step very Strong Minded of you Love x x x I would love to chat On line with you as well babe please if yopu can Love and maybe swap some Pics as well babe x x


    Saundra P Ryan

  16. simone88 5 years ago

    This is amazing! this website is a dream come true for me. I have been shaving my legs, on and off, since I was old enough to have hair on my legs. I have had trouble admitting to myself that I’m different, and am only just recently free to explore my sexuality. I spent most of my life pretending to be a “macho man”, all the while, scared as a little girl. Still scared, probably will be for a long time to come, but with sites like this, I don’t feel so alone. THANKYOU!

  17. Mid 4 years ago

    Such a lovely website!
    At over 70, proud grandfather, devoted to ex-wife, living by myself I have had such joy over the last few years to wear pretty things, feel satin against my body, and strut around feeling sexy in heels, earrings, and necklaces.
    Coming out totally? No. My friends, my family and my business partners would never accept that.
    But daily, every day now, a little makeup, lipstick, eye, everyone seems cool with that.
    Androgynous women’s silk long trousers, taffeta shirts, that button up the wrong side. These seem to be OK.
    Short ladies shorts and big belts in summer, everyone but family hardly notices.

    I have got used to being a little feminine outside. Feels Great ! Somehow, the lipstick seems to be getting bolder, the low heels a little higher.

    Life is for the living, darlings !

  18. Sam victor rose 3 years ago

    Hi it is very difficult to travel in train or air where identification has to be shown when u r having identification for ur mslr name. How to overcome this ? Can railways deny entry if u book in my male name ?

    • Author
      Vanessa Law 3 years ago

      I can’t really comment on ID – I have never traveled without ID appropriate for my gender presentation. I am sure they have seen it all, though it would be unfortunate for a hateful individual to make trouble for you.

  19. Lolita Hope 3 years ago

    What scares me, is being raped and killed, en femme

    • Vanessa Law 3 years ago

      That’s not an unreasonable fear hon, as we’ve seen quite a bit of violence against our community in the past. I’d recommend finding a support group, and going out with friendly company.

  20. Sarah 2 years ago

    Very helpful the reason I’m not going out as much as I would like is my 19 year old son move back and he’s home when I’m home

  21. Joann 2 years ago

    I just started to go out dressed the first time was just like most of us but what a thrill it was now I can’t get out enough my wife knows but does not like me going out she is abraded I will get seen but hollowed not is coming up and I have just bought a sexy red dress and 5 inch heels I can’t Waite but for now I sit hear with my bra and panties on I wish I had some one to go out with any one in central Minnesota out their

  22. johngordon 2 years ago

    All of the above!

  23. Bronwyn 12 months ago

    Fear fear fear is what has kept me in the closet fo 30 years. Being a total introvert does not help at all. But thats my personality and at my age, wont change. Some can go outside thier front door, many cannot. Bronwyn

  24. Rebecca Smith 12 months ago

    I’ve driven home from drill dressed up twice now. Last weekend I wore make up. I still need to practice that aspect but I didn’t think it was too bad, tried to keep it minimal.

    Anyway, I made a point to make sure I was dressed femme to get my mid-point gas and to use the restroom. Honestly it took every bit of courage to walk in there. I’ve been in several dangerous situations and I think my heart rate was quicker walking to that stall.

    I don’t know that I could have done it without the awesome ladies on here and their encouraging stories and advice.

    I did learn that a longer dress would have been nice given the windy weather. I should have brought more than one outfit just in case.

  25. Susanna Monroe 8 months ago

    For me it’s fear that I’m not as good at this as I think and I’ll get called out, laughed at, chased with pitch forks, that kind of thing. I recently did my first outdoor trip but didn’t leave the car. Small steps and all that…

  26. Veronica Raines 5 months ago

    Don’t know, if this counts, as this is the first time, I’ve told anyone about how I feel, about wearing proper clothes. I sort of grew up, in a small town of 1,200 population. It was basically run, by the Italian mob. There were only 52 kids, in high school. One Halloween, I went to the party, at the high school, dressed like a woman. My mother helped me, get dressed in her clothes. A white bra, with falsies, under a white blouse. A pair of white panties, under a black skirt. She had some low heeled black shoes, and of course, I wore her nylon stockings. I also wore her black, little hat, which had a veil, with a pair of black gloves. Of course, she put makeup, on me. It was about six blocks, to the school, from our house, and I started off walking, carrying, a chocolate cake, for the party. She had taught me, to always walk with my head held high, and as I walked to the school, (it was dark) I felt so proud, that I walked with my shoulders back, and head held high. On the way there, a black car, with the two big shots, of the school, in their senior year, were in it. They made a U turn, and drove back by, whistling at me, and say, “Hey baby, where you going.” Of course, I said nothing. They made another u turn, and came up beside me, saying all kinds of things, kids back then, said to girls, when they were trying to pick them up. Then finally, one of them asked, if I was going to the party at the high school, and I nodded my head yes. It was a two door coup, and when they stopped, the most sought after senior in the school, with the nickname, Tiger, got out, and held the front seat, forward, so I could get in. However, he asked if he could hold the cake, while I did so. Handing me the cake, he got back in the car, and Bill, the other senior, started driving, very slowly, towards the school. Of course, Tiger kept trying to get me to say something, and then I couldn’t hold it back, any longer, and started laughing. Of course, everyone knew, everyone, and they both knew my laugh, and Tiger jumped over the front seat, saying, WTF, is that you Steven. I just nodded my head, and Bill stopped the car. I don’t remember, what all that was said, between us, but they made me get out of the car, and told me, if I ever told anyone, about this, they would beat the crap, out of me. As I walked the rest of the way to the school, I felt so damn proud, that they thought I was a girl. At the school, when I walked in, the lights were on, and everyone knew who I was. For the next couple weeks, I got ribbed about dressing like a girl. Plus, two guys that never did like me, tried to make something of it, and I had to kick their butts. That was the only time, I dressed up like a girl again, and left the house to be seen. Apparently, the head man of the mob, heard about it, and got word to my mom, not to let me do it again. Now, I’m starting all over, the way I should. You never grow to old.

  27. Maya Honey 3 months ago

    Lovely and inspiring. My problem is my best friend and lover for 17 years or more does not like my dressing. I am not man enough.
    (Shock! I have beard up to Xmas for her so dressing ain’t so good at the mo!) Love and admire you all. X

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