Going Out Crossdressed For The First Time

Nervous about going out crossdressed for the first time

I’ll never forget my first time going out crossdressed, even though it’s almost eight years ago now. I had been dressing at home for many, many years and underdressing as often as I could, but I had never been out ‘en-femme’ before. A few weeks earlier I had joined a local crossdressing group and  had finally plucked up the courage to attend a Tri-Ess meeting.

In my infinite wisdom I thought it would be a good idea to go out crossdressed for the first time. I was conservative in my femininity – I wore a blue blouse over some slightly feminine jeans with a bra for my breastforms and just a dash of makeup. With trepidation I exited my apartment, eager to quickly make the trip down two flights of stairs to my car without being seen. Then as I step foot into the parking lot I’m confronted by

Cops, everywhere – and they’re after crossdressers!

And I’m dressed. They’ll notice my boobs and my feminine blouse. Oh God! Now I’ve gone and done it I knew I shouldn’t have dared to venture out crossdressed. I almost died of embarrassment right there. I knew I was going to get into trouble, or at least a stern rebuke.

As it turns out, the police officer wasn’t outside my apartment waiting for crossdressers and he didn’t pay me much mind. I got into my car without any problems, and was off to my first Tri-Ess meeting.

Over exaggerated fear of what will likely never happen. That’s what I experienced the first time I went out crossdressed, and I have a hunch that I’m not alone. Our worst fears rarely come to pass yet we spend so long dwelling on them. It’s only when we’re out in the moment that the fear can be replaced with the joy of expressing one’s feminine self.

Going Out Crossdressed For the First Time

A few weeks ago I was blessed to take my good friend Vicki on her first crossdressing expedition into the cisgender world. She had visited the Emerald City (a local transgender club in Seattle) before, but leaving the safety of an understanding transgender group was new for her. We started out the afternoon with lunch at Chinese restaurant that we had all to ourselves, and despite some interesting smiles from our hosts it was a great way to ease into crossdressing in public.

Vicki truly showed mastery of her nerves when she suggested a quick trip to the mall together. Dining in a deserted restaurant is one thing, walking through a crowded mall is quite another. It was wonderful to see the sense of joy and accomplishment in her face as she took a proud step forward into the world as her feminine persona.

What was you first time going out crossdressed like? Was it nerve wracking, exciting, joyous, liberating or something else entirely? I’d love to hear, comment and let me know.

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  1. kelli anne Busey 7 years ago

    Hi Vanessa,
    your article brought back many memories. I was historical. I knew I had to step out dressed and I walked towards that door literally 100 times before actually stepped outside. I was so paranoid I had rented a motel room in a nearby town to make m first foray and I knew, just absolutely knew that ALL the people in he motel looked out of there Roms at that moment and where laughing hysterically.
    That day was the first step. I am now legaly female and work as a cashier at a major retailer in a conservative southern state. I have the highest regard for our Tri-ess chapter. The president of that chapter was one of three transgender people to speak infront of the Fort Worth Council before the passage of its gender inclusive city ordinance.

  2. Profile photo of Vanessa Law
    Vanessa Law 7 years ago

    Hi Kelli Anne,
    Hehe – it’s amazing how everyone has perfect tranny radar, and know just where to look isn’t it 🙂

    Congrats on your successful transition dear, it must seem like so many years and memories away from the first time you ventured out crossdressed.


    • Carolyn 7 years ago

      I practiced for about 1 year before I first went out. And even that first time out was at about midnight so that no one could really see me.

      After a few times out in dark of the night, I started to go to a transsexual / gay club. I would change in my car and spend the night as Carolyn. It was an accepting and supportive atmosphere and I needed that. However, I am really not into the gay scene.

      Now I’m fulltime and will be having SRS in March 2010.

      Go girls!

      • Profile photo of Vanessa Law
        Vanessa Law 7 years ago

        Congrats Carolyn – phew, that must have been a long year or trepidation for you dear.

  3. Racquel Lynn 7 years ago

    I guess my first time was as a kid, but it was halloween. I said I wanted to go as a girl and my mom threw everything together on me and made it comical. I still had alot of fun, but it wasn’t the outfit I would have picked out or the look I was after. It made for a fun night trick or treating but did not do so much for reaching into the real me.
    As I got older, as most crossdressers do, I dressed up as myself for halloween, or at least as a female character. Many times I just went as my female self and usually passed really well for the most part, even alot of people I talked to every day did not realize it was me until I started speaking. Other times I would go as a female character. I tried being Morticia from the Adams Family (the old TV version), which was okay, but wasn’t the best. A couple of years later, I went as the Angelica Houston version of Morticia, from the Adams Family movie and everyone thought I made the perfect Angelica version of Morticia.
    I had gone out occasionally as a female in my late teens/early 20’s with a few girlfriends that would like to have fun playing with my hair because I have always had my own long hair, plus being in bands in the 80’s I never went out without eyeliner on at the least. So girls always loved taking turns fixing my hair for gigs or just for fun other times. Many times they would also want to put make up on me and, of course, I would let them. They often would tell me they thought I would make a good looking girl and would ask if they could fix me up sometime and do my hair and make-up more feminine instead of rock n’ roll/glam rock, but to intentionally make me up to look female just so they could see what I would look like. You never heard me refuse! lol I actually loved it and was wanting that look before they even asked.
    (The great thing about the 80’s is that you could be crossdressing in plain sight and no one would know! lol unless you had a skirt, high heals or a bra on that was stuffed, no one thought much of it, you were just another cool rocker or a poser! lol)
    Girls would do my hair up, put make-up on me and then let me riad their wardrobes or they would pick things out for me, (Sometimes they let me wear their clothes for band gigs, other times they would let me wear other clothes to see what I would look like as a girl.
    Although I was not actually out to anyone back then that I actually identified as being a female and wanting to have a sex change, or that I even liked to cross dress, I was comfortable going out with friends after the girls made me up as one of them. I wasn’t really considering it as crossdressing at that point as much as just being silly and having fun with my by best female friends. We all did have so much fun together.
    So even though I was dressed female and going out, I wasn’t really trying to pass myself off as female, but loved it when I was passing.
    I think that is why when I started going out crossdressed later in life, intentionally trying to pass as female when it wasn’t halloween, I realized pretty quicky that when you are comfortable with who you are and not worried about what others think and just live your life and having fun that you are more passable and more accepted by others than when you are nervous and scared and worried about being outed.
    You can look your best and be outed faster when you are afraid of being found out than when you don’t look as perfect, but you feel confident and just don’t care if anyone knows.
    I guess my first time that I went out intentionally trying to pass I was pretty nervous at first. Getting out of the car to go into a store was the longest walk I think I had ever taken. I did get a few looks once I got inside (6’1″ tall woman, it’s bound to happen. lol) but people are actually great in most places. I went shopping and then went to work that night for the first time as Racquel. I thought I would be more nervous about work than the general public, but a few people there already knew about me and the rest that found out that night were very supportive. The more places you go, the easier it gets, at least in my experience. The first time is the hardest, and I think you should make a day out of it and have someone close to you who supports you to be with you. I think it’s much harder to get ready and then go out to only one or two places for just a short time and then rush back home where you know it’s safe because you have let the fear, nervousness or everyone staring at you get to you.
    The longer you stay out and around other people, especially crowds of people that you don’t know, or may run into someone that you know, is actually better for you in the long run. You will get more relaxed as the day goes on and start acting more naturally and start learning to ignore the stares and the talking. Then it starts feeling easier.
    I have had a few jobs that had absolutley no problem with me coming to work as Racquel. Even during times when I wasn’t doing it full time.
    I am looking forward to soon being able to live full time as Racquel again. It really sucks that we live in a world that just to survive, we have to not be ourselves. But my day is coming and when it does, I will never go back to living as a male again.

  4. kimberly 7 years ago

    hi im a new crossdresser out of the closet . i live in a small town hear in cal and i try to go out but i git so far and i git nerves and go back home thar is no one hear for me to help me git me over the shaking nevis that i have is thar eny one out thar close to me to help me out i live in orland calafona . help plees

  5. Suzypier 7 years ago

    Hi, I am still in the closet but use all the opportunity I could get to crossdressed. My wife is going away for vacation in a few weeks and i am looking forward to crossdressed during that time. I am also looking this time to try to go out for the first time, just hope I will be able to do it. Have a Merry Chrismas to all.


    • Joann 1 year ago

      Suzanne I would like to go out with you I
      Have only gone out dressed up three times and would like some one to go out with

      • Joann 1 year ago

        Suzanne I left a reply but have not heard from you lets go out some place looking good and feeling better dressed up like beautfull women

      • Joann 1 year ago

        Suzanne lets do it e mail me frank an 1947@gmail.com

    • Alex 7 years ago

      Going out for that first time when you are married is definitely scary. I have gone out a few times when my wife is out of town, always worried I would see someone I know. Or worse, they would see me! Last time, I convinced myself that I would just go out and have a great time. I got a massage from a wonderful therapist who turned out to be very supportive and sweet. (She had a boyfriend, though. Otherwise, she said she would have loved to go out with me!) Then I went out for a late dinner at a Chinese restaurant. (I have found that Chinese women are more comfortable than American women are with crossdressers.) Exhilarated after my positive experience, I went home and culminated what turned out to be a very romantic evening : ) ! I was so satisfied with the experience that I got up the next morning, dressed up again, took the train downtown and went shopping…en femme! Again, it was so wonderful! I just didn’t worry or allow myself to be too self-conscious. And no one gave me the evil eye. I even got to try on a wedding gown!
      So, just be comfortable with how you look. You may even schedule a makeover for the morning of your day out at a local department store, like Macy’s. Make sure she knows ahead of time what you are doing so she can help you plan it all out.

      • Profile photo of Vanessa Law
        Vanessa Law 7 years ago

        Wonderful advice Alex!
        Suzanne, good luck as you venture out. Make those butterflies fly in formation 🙂

  6. Emily 7 years ago

    hiya Suzanne,
    Same here I’m still in the closet where going out is concerned, the only people I’ve come out to is my friends and family.

    However as a male I do amateur photography and going out with professional grade equipment was something quite nerve wracking at first, people looking and commenting on the size of my camera, but now when I go out I don’t even notice the comments anymore, just focus on great photographs (landscapes and macro).

    Hopefully it will be the same if I decide to go out crossdressed as Emily, like the photographic side, over time it would become more second nature.

    • Profile photo of Vanessa Law
      Vanessa Law 7 years ago

      What a great analogy Emily. Anything we do that is different can draw comments from people. Most of them are probably just curious – we shouldn’t let other people’s interest stop us from doing what we know we should be doing. Let your crossdressing muse make artistry in your life 😉

  7. Sylvia 7 years ago

    I attend a group based in Blackpool, UK, at an small hotel. Please visit the website, by putting renaissance blackpool in the search engine.

    A couple of weeks ago I was able to get to Gynway (the Hotel), and dressed about 10.am. Petra went out shopping, but I was able to chat with a rather poorly Lynda. I then decided that I would brave the big wide world for the first time!

    I walked down to the Prom’ (ie sea front), (grey pleated M&S skirt, pink top with cardigan. I thought the front, being deserted, was not a place for a woman on her own, unless walking a dog, or accompanied.

    So I headed up to Dicson Road. Near to this road, a family were getting into their car, and the small daughter waved to me, smiling. I waved back, and exchanged an understanding smile with mum. I am sure she did not “read” me. I walked Dicson Road, passing quite a few people, without anyone, that I could see, giving me a second glance.

    I came across a shop selling second hand goods,including clothes. I found a skirt, and some boots, both unworn. There were two ladies serving (actually playing cardsmainly!) and I asked if I might try the skirt on. The older lady replied that there was nowhere to do this, but that if I returned it, they would credit me. I was probably “read” because of my voice (I am working on this!), but no comment was made.

    Returned to Gynway, and tried the skirt on. At size 16 it seems slightly large, but it is so pretty, with two front splits, that I will probably keep it.

    My shoes (size 6 black courts) seem to be getting larger, so it could just be that my efforts to lose weight are paying off.

    This was originally written as a blog entry – I hope my English is not to confusing to our transatlantic sisters. Date was middle of October. I have since been out (shopping esp.) several times. My blog can be read on the renaissance website.

    Love to all, and a Merry Chrismas and Happy New Year!

    • Profile photo of Vanessa Law
      Vanessa Law 7 years ago

      Wonderful Sylvia, thanks for sharing! Even if you were read, it’s great that the shop assistant was still polite. I find that even when I’m read people are generally courteous – very rarely will someone make a scene.

      For any ladies looking for a support group, you can find the web link to Renaissance and others here https://www.crossdresserheaven.com/about/crossdresser-support-groups/

  8. Sylvia 7 years ago

    I attend a group based in Blackpool, UK, at an small hotel. Please visit the website, by putting renaissance blackpool in the search engine.

    A couple of weeks ago I was able to get to Gynway (the Hotel), and dressed about 10.am. Petra went out shopping, but I was able to chat with a rather poorly Lynda. I then decided that I would brave the big wide world for the first time!

    I walked down to the Prom’ (ie sea front), (grey pleated M&S skirt, pink top with cardigan. I thought the front, being deserted, was not a place for a woman on her own, unless walking a dog, or accompanied.

    So I headed up to Dicson Road. Near to this road, a family were getting into their car, and the small daughter waved to me, smiling. I waved back, and exchanged an understanding smile with mum. I am sure she did not “read” me. I walked Dicson Road, passing quite a few people, without anyone, that I could see, giving me a second glance.

    I came across a shop selling second hand goods,including clothes. I found a skirt, and some boots, both unworn. There were two ladies serving (actually playing cardsmainly!) and I asked if I might try the skirt on. The older lady replied that there was nowhere to do this, but that if I returned it, they would credit me. I was probably “read” because of my voice (I am working on this!), but no comment was made.

    Returned to Gynway, and tried the skirt on. At size 16 it seems slightly large, but it is so pretty, with two front splits, that I will probably keep it.

    My shoes (size 6 black courts) seem to be getting larger, so it could just be that my efforts to lose weight are paying off.

    This was originally written as a blog entry – I hope my English is not to confusing to our transatlantic sisters. Date was middle of October. I have since been out (shopping esp.) several times. My blog can be read on the renaissance website.

    Love to all, and a Merry Chrismas and Happy New Year!


    • Sylvia 7 years ago

      Further to my entry above – I have been out shopping “en femme” several times since. I have again been to the shop I mentioned, and they are friendly.

      I am trying to push the boundaries out, (ie using a restaurant for coffee, using the Ladies’ room, public transport etc) and taking every opportunity to interact with other people. Having a lot of fun, too! I hope my “english” isn’t confusing,

      • Ragina 7 years ago

        Hi Sylvia, I’m Ragina. Congratulations on your explorations. You are Breaking new ground for all of us. I only wish that there were more here in the states as bold as you. Perhaps then more of the “strait” world would not be as judgemental and condemning of the transgendered community, if they could see that we are just people, perhaps different in some ways, but people nonetheless. Good luck in what you are doing, and please, keep us all posted as to your progress. Love, Ragina

    • Maddy 7 years ago

      Hi all, I too am from the UK, but am currently ‘closeted’. My wife is supportive and a few close friends know too, but I doubt to whether I could ever pass as a woman on the street, which makes me feel quite sad. I also have young children too and don’t want to cause them any distress either.

      I am however trying to find the confidence to go out crossdressed for the first time (other than to a fancy dress party – how I love those), but I live in a small town in which I would no doubt bump into someone I know. Has anyone got any tips, or places where you can be eased into it gently?
      Sylvia, your hotel sounds interesting, and I will look into that next.

      Anyway, got to get back in my male attire before the family get home (sigh). Seasons greetings and much love to you all! Maddy x

  9. Profile photo of Vanessa Law
    Vanessa Law 7 years ago

    Hey Maddy,

    Support groups are always a great place to start. If there isn’t one close by, perhaps going for a drive in your car would be a good way to be ‘out’ without the fear that you’ll run into someone you know.

    • Maddy 7 years ago

      Thanks for the advice Vanessa, I think a car drive ‘en femme’ is very much on the cards! Your site offers an invaluable lifeline, despite being the other side of the Atlantic.

      If you’d indulge me, I’ll let you know how I get on – I know it’s a comparatively small step to what many have gone through, but it probably has some relevance in this thread. I think 2010 could be very exciting!!!

      Love to all, it’s been a genuine boost reading everyone’s experiences regarding their first time out. xxx

      • Donatella 6 years ago

        I'm glad I came across this post. I had to meet up with my business partner a few days ago. I also needed to stop in my cross dresser's store because I needed a few things. Well, he was early, and the store closes early, so we met and I kind of rushed him so I could get back to the store and change into my girl clothes! I got there just prior to closing, but they were kind enough to let me changed. I had to put make-up on in the car, tho! What a challenge. Then began the 175 mile drive back home! I am petrified of being in public in girl clothes, so I figured that in the car, is kind of like being at home. I really enjoyed the wind in my hair (wig as I only get a really bad afro when I grow my hair long 🙂 ) The drive was pretty uneventful, but it was beautiful out and I had to pass near the cemetery where my dad is buried, so I stopped by there. Hope he didn't see me!

        The reason for my fear is that many years ago, before I even thought about x-dressing, my wife & I lived in a predominately gay neighborhood, in a beautiful loft. I was walking home from dinner one night when a gang that was out gay-bashing jumped me and left me for dead in the gutter. So, my fear was palpable even in the car. I didn't stop for anything, except for the cemetery since it was late and no one was there. I'm glad I did this, but I'm still very, very afraid. I mean, if that happened to me and I wasn't in girl clothes, what can happen when I am in girl clothes?

    • Carol 7 years ago

      Back in the mid 70’s was when i first started going out. i remember it well, i wore a short black skirt, red blouse, and suntan stockings. Had penny loafers on my feet . I threw my purse over my shoulder and out the door I went. still remember my heels clicking on the sidewalk. Now Im old, but went out last night, and guess what. I was wearing a skirt and blouse, suntan stockings, and my Mary Janes, and when I put my purse strap over my shoulder and went out the door….. the door, it was yesterday once more. Carol Ann

  10. Carol 7 years ago

    When I first went out back in 1975 I wore a black skirt, red blouse, and penny loafer flats. I wore plain suntan stockings, and a brown page. I swung my purse over my shoulder and out the door I went. I got to thinking that the other night I had on my gray skirt, suntan hose, purple sweater, and Black Mary janes. My hair style is longer now but I look near to what I did 35 years ago. when I swing my purse up over my shoulder its yesterday once more. carol

  11. Leslee 7 years ago

    My first time out happened about 5 years ago.I found a cross dresser entertainer who did make overs and I brought my own cloths.She did a wonderful job with the makeup and I felt great until I stepped out of her appartment. I thought every eye was rivited on me and even in her car I felt nervous. We went to a cross dressing show and even got a free meal on the house as we were cross dressed. The night finally ended but I didnt want to take off my make up or cloths. I felt wonderful and now feel absolutely at ease when dressed up.If my wife was more understanding I would dress every day.

  12. Emily 7 years ago

    I’ve done it….
    Went out as Emily today, enjoyed every minute of it. I was a little bit nervous at first but after a few minutes had passed, I’d got into the flow of things and just enjoyed the day.

    have a great new year

    Kind Regards


    • Ragina 7 years ago

      wonderful to hear, Emily. I hope to do the same soon myself. I’ll keep you posted as to what happens.Lots of love, Ragina

    • Racquel Lynn 7 years ago

      Congradulations and way to go, girl!

    • Profile photo of Vanessa Law
      Vanessa Law 7 years ago

      Congrats dear! So wonderful to hear 🙂

  13. sophie 7 years ago

    well i am fairly new to cross dressing and io want to tell people but i find i cant. i mean i am only 15 and i should tell my mum but i’m not sure about it . should i tell her becuase i am not sure wot she will think of me. she has always been proud of me but will me telling her this make her think differently of me need some help here any advice

    • Leslie 4 years ago


      I came out to my wife recently. I was frightened to death of what she might think of me. She must have known something was up, because I suddenly became all lovely-dovey, hugging and kissing her every time I saw her, not sexually, but in a sad way. The truth was that I thought there was a chance that she might never want to look at or speak to me again. But I couldn’t keep it from her anymore. It was tearing me up inside.

      So one night I broke the news. She took it well. She’s a very strong woman. And despite reasonable reactions, fear, anger, grieving, we’re working through it together. We’re determined to stay together if at all possible. In fact, through the crisis we’ve become closer than we ever were before, emotionally and physically. I never expected it to happen this way.

      Of course, we have a long way to go, but so far so good. Not that I’m trying to sugar-coat anything for you. Often times, people don’t understand and don’t react well. But you never know until you open up to them. Just be cautious. Hint around the issue some first.

      Good luck!

    • Ragina 7 years ago

      Hello Sophie, I’m Ragina. Yes I think that you should tell Mom about your crossdressing as soon as you feel comfortable to do so. I speak from experience that it is better to tell her than to have her find out in an uncontroled way, such as catching you en femme without any warning. It can really lead to a very unpleasant confrontation that you just do not want. My Mom found out that way and it got ugly real fast. Fortunatly, after a while, cooler heads did prevail and we had a good chat about it later, after things calmed down. It took a while, but the aceptance did come. I only wish that I had access to this wonderful thing called the internet back then and all the great sites that are there.Take your time and make sure that you have plenty of positive information to share with her. Be ready to answer a ton of questions and be geady for a bit of guilt” where did I go wrong” type of comments. She did nothing wrong, and neither did you. Above all let love and understanding prevail. I will pray for you that all may go well.
      Sincerly, Ragina

      • sophie 7 years ago

        thanks for the advice it was really helpful i have told her and she was shocked or suprised att first but things have been sorted out now and i think its all goin well now

      • Ragina 7 years ago

        Hi Sophie, Ragina here again. I’m glad to hear that the talk with your Mother went well. Remember to keep things on the up and up so as not to betray the trust that has started to build. This is a positive start. Always be truthful in answers to questions, and if you don’t have an answer, get on the web and get the information you need. Don’t try to BS your way around. Always be well informed and I feel that you will be fine. Best of all to you. Ragina.

    • Racquel Lynn 7 years ago

      You never know how anyone will react. I am lucky that I have only lost one friends since I came out to my friends. Many that I thought were going to not take it well have been some of my best supporters. I have been very lucky. Many others I have talked to say that some of the most open minded people that they have told that they expected would support them turn them away and those they didn’t expect to supported them. You really just never know.
      I am now 42, and working on telling my Mom, who doesn’t know yet. Only very few in my family know about me, or at least they don’t know the whole story. Actually today looks like a rare opportunity to have that talk with her while everyone else is out of the house. So I am planning to finally do this after breakfast. (Wish me luck!)
      But from my own experience, I would say that if you feel that you rfemale side is more than just a phase, but rather is a part of who you are as a person, you should tell your mother as soon as possible. The sooner, the better. It will make things easier later, not that it is ever easy being transgendered, but it is better than hiding your true self. You only get one chance at this life and you have to live it as you and do what makes you happy. Evenif your mother doesn’t take it well at first, give her time. Find any good educational material on the subject that will help her undertsand and find a support group if you have one available in your area. There is also a wealth of information, support and resources right here on the ineternet.
      I bought my Mom a copy of “True Selves” by Mildred Brown and Chloe Roundsley. It is by far the best book for information on crossdressing and transsexualism to help family, friends, coworkers, etc. to better understand things from our perspective. I am hoping to give that to her today.
      The main reason I have not been completely out before now is because of my Dad, who is the next big obstacle. He is the reason I stayed in the closet as long as I did because when I mentioned as a kid that I wanted to have surgery to be a girl, he made me feel like the worst thing in the world. I don’t hold that against him, but it did hurt. Now I am not worried if he accepts it or not, but he has a bad heart and I don’t want to kill him by telling him. I was actually transitioning to female in my public life when his heart got in bad shape, so that is the only reason I put it off further. I do regret not just being myself from the get go and then everyone would just be used to me and accept it more. Those who may not have, well, who cares about them if they are not going to care enough to try to understand.
      I think the younger you let people know, the better off you are later in life, even if it is hard for a while.

      Good luck in what ever you decide!

      • Racquel Lynn 7 years ago

        The one thing I have going in my favor is that I know my mother already knows at least part of it, because when I woke up in the hospital after my car accident, They had taken my jeans off, so I was in the hospital in my shirt and panties. I did have a blamket over me, but I know that everyone knew. When they came to take me for a cat scan, I heard my Mom ask the nurse if she could give me two hospital gowns because she didn’t want me to be ambarrassed by amyone seeing my panties as my rear hung out of the one gown. So they put one on backwards before they put the other one on. lol

        Anyway, although it has never been brought up, I know that she knows that I at least crossdress, but she doesn’t know (as far as I know, unless someone else has told her) that I plan to become full female.

        Once again, my opportunity to talk to her was interrupted by others coming in before I could bring it up. I think tomorrow I am just going to take her for a drive and talk to her that way.

      • chrissie 7 years ago

        I use to crossdress all the time starting in middleschool. My first time being seen was dressing at home (mostly mom’s clothes) and having a pizza delivered to the house. I opened door totally en-femme and paid the driver… my knees were shaking so bad as I waited for him to count out change…I just wanted to tell him keep it… but I was in school and money was in short supply. The driver never paid me or my attire any notice. I remember being so nervous I couldn’t even eat the pizza..hahaha..

        After that I was hooked.. the rush of going out was such a exciting event.. first just driving around, then late night walks at night, runnin g into store for cigarettes(didn’t smoke) to going to movies or walking in mall on other side of town.. each new adventure was more and more exciting

  14. sophie 7 years ago

    i been out in public before and i found it liberating i found tht it gave my confidence and i enjoyed it yet i still havent told my family i dont no wot to do but i made a step in the right direction but any advice?

  15. sophie 7 years ago

    thanks for the advice it is really helpful and i wish u luck as well

  16. emma williams 7 years ago

    I have been crossdressing for about 10 years now but have only been out in public 3 times , I did get a few comments on one occasion but I felt so empowered I didnt care , the reason I havent done it I think is because I will reach a point where I cant be anything but female and I am not sure what will happen then

    • Leah Marie Lynn 5 years ago

      This is the site I’ve been desperate for! You seem to have many answers that I’ve been asking for; only I’ve been asking empty space, not knowing where to look. Thank you for being here. Leah

  17. becky 7 years ago

    I have to say I love the feeling of putting on a pair of panties and a bra, Ive beem a crossdress of 9 yrs.and I love slipping on a mini skirt and a blouse with nylons and heels. You might ask how I got started my sister when I was 13I went and told her that I want to try on cloths and she.Took me into her room and made me into her sister I dont think she realize that .I lovedbeing dresses has a girl. But over the next year she show me how to wear makeup do my hairwalk in heels.So i could go out in public.And I have done that and will always be in her debt .

  18. Ashley 7 years ago

    I just saw this article today, which is coincidentally the first time I’ve ever really been out while crossdressed, so I thought I’d share my experience.

    When I say “really been out” I mean out in a crowded area during the day. I have gone walking near my home at night while dressed, and even driven to a mall after hours and walked around the parking lot, but today I took a much bigger leap.

    I went to the store in the morning and bought a bunch of make-up, then I came home and set to work applying it, which took a long time and many attempts where I just wiped it all off and started over. Once I was satisfied with my overall look, I walked to the front door and…stood there. For about 10 minutes. Finally, I pushed the nervousness aside and walked outside to my car. I kept putting my hand near my face to prevent other drivers from seeing it, or pulling my hair down to cover up.

    Finally, I got to the mall and…sat in my car. I was so, SO nervous. Instead of getting out, I stared into the mirror and talked to myself: “You are feminine, you are pretty, you look great, no one will know.” After about five minutes of this, I slowly opened my door, got out, and began the walk to the mall. I felt like I was on a stage, despite the fact that none of the people I saw even spared me a second glance. It was going well, but it got even better once I got to the door of the mall. The gentleman I was walking behind pulled the door open, gestured to the entrance, looked me full in the face, and said with a smile and nod “Ma’am.” I smile shyly back at him, and my stomach dropped like I was riding a roller-coaster.

    I went straight to the women’s restroom, where I passed two older women coming out who said “Excuse us, dear.” After touching up my make-up a bit (unnecessarily, but I needed something to do) I went back into the crowded mall and walked down to the end, then back to where I came in. As I was walking by the Electronics Boutique, I passed a family near the window. The little boy pointed at the display I was walking by and said to his mom “That one, the one the girl in the black shirt just passed.” I wanted to just run over and give him a hug!

    After that, I became very self-conscious again out of the blue, so I just bee-lined it right to the door and walked to the car. I’ve been crossdressing for about 14 years, and I finally found myself with the courage and opportunity to head out in public. For my first experience out, I really couldn’t ask for anything more, and after such an encouraging adventure it will most definitely not be my last!

    Now I realize I’ve written a LOT, and I apologize for that, but I was so excited about the day that I had to tell someone.

    • Racquel Lynn 7 years ago

      You don’t have to appologize for a long post. ( At least I hope not, or I have a lot of appologizing to do myself! lol)
      Congradulations on your accomplishment today. The more you go out, the easier it gets. Once you start getting used to being yourself in public, you tend to stand out less because your confidence raises up as you enjoy yourself more and more and you get relaxed, then your don’t have that look on your face that screams “Oh my God do they all know?” Once you get to the point that you do not care what people think or if they are looking, or you just don’t notice them anymore, then you start becoming more passable because you’re no longer trying to notice if you’re getting noticed. It all comes with time.
      It’s also a great thing if you have someone to go out with and just spend time out in the open with a friend, wife, girlfriend, family member….anyone that is supportive and accepting of you.

      Keep it up and keep posting!

  19. Molly O'Lani 7 years ago

    Ummmm, the first time was in Manhattan many years ago. I had been dressing and mking dresses with a friend at her apartment and mine. We would go to cross dressing groups but I would not dress to go. Then a couple invited us to their apartment for dinner and we accepted only after they accepted to come to my apartment. We had a lovely time and I cooked with my girlfriend for them and we talked and got to know each other as couples. The wife to the other couple wwas very open with me about my dressing adn complimentary adding to the night’s pleasure. It was so fun being dressed adn having guest over for the whole evening. When they left my girlfriend said to me “Now do you envy him leaving dressed to go home wouldn’t you like to dotht?”I quivered and said yes. A few weeks later we crossed town in my car with her driving with me dressed for dinner. I was terrified leaving the apartment to the car adn even in the car. We were stopped by a cop for making a wrong turn and we talked our way out of a ticket. As we continued our drive my girlfriend said to me “That cop couldn’t take his eyes off you, I’m jealous!’ I answerred, “He was checking me out to see if I was a guy in a dress adn I think he was confused.” “Oh he wasn’t confused, he liked what he saw, he saw how pretty you are.” I blushed crimson with her remark. When she asked me if I thought the cop was cute I refused to answer.
    Leaving the car and walking several blocks to our host’s apartmetn was a continuing shaking at the nylon kness experience. I am 6′ 8″ in heels and everyone we passed on the New York City streets turned heads. No one said a thing. Just looked. I couldn’t wait to get inside. Once there it took me ages to calm down and enjoy dinner and dreings adn dance a bit. Then I had to tread going home. I was so excited i almost fainted. Once home I did what every red blooded girl does. I ripped off my bra and heels and fell to the coach and cried running my mascara all over my cheeks.
    Years went by before I did it again. And I learned a great thing by waiting. It isn’t scarey now. Oh when I went out the first time I was again very self conscious. But then I noticed nobocy in Manhattan gave a damn. I hailed taxis, went to restaurants and events with so much more ease.
    I loved it. It’s a lot of work even when I dress down and casual for an afternoon shopping tour. I get kids now an then giggling but I understand I’m an an unusual sight for them as they are looking so intently for thier own identity at that age. Most adults and all store keepers love my money adn me coming into their place.
    Being with other girls is the secret to enjoying yourself. Hearing “yes dear, that’s looks lovely on you. or Oh no sweetie never on you” is so fun and girlie.
    I can get up tight from time to time and think twice before I go through the work of looking nice, but I’m always thinking when I see a dress or skirt or demin slacks on a girl how i would look in it.

  20. loni 7 years ago

    the first time…it was bad and good. just not good at makeup, but a couple gg asked me were a local beauty shop was at. my voice croked out a ‘no’.

    getting out in daylight, all dressed up…..O how can one put it into words. if you long to dress and walk out the door. do it before you get too old. it is great.
    the excitment, fear, you are scared to death. but nothing happens and you have been addicted to being your self. it’s great fun.

    been some time back, had to lock up loni for a couple years…but this year she is back. and kicking up her heels….still need makeup help, but now i know of a couple places.


  21. Jane 7 years ago

    Hi Girls.
    I have been out quite a few times I have also been in work as Jane and had a great time everyone was so good the girls were best and offered so much advice. I also started when I was 9 with my sisters clothes but now I am 60 I have my own stuff which is so much better. I love mini skirts and everything fem. My wife knows about Jane and even buys me stuff but she dont like me going out or seeing me dressed.
    Jane xx

  22. Julia 7 years ago

    I started crossdressing when I was young, but I didn’t go out dressed up as a girl until I was 13 & I dressed as a girl for my boy scout Halloween party. My mom said she didn’t have time to get me a costume, then she said if I’d dress-up as a girl I could wear her old school uniform, my sister’s cheerleader uniform or my mom’s white tennis dress. Little did my mom know that I had started dressing up in her clothes earlier that year & now she said I should dress-up as a girl, this was a dream come true. I wore mom’s white tennis dress (it was very short & tight), plus a bra (well padded, stuffed), panties, pantyhose (I shaved my legs too) & a pair of white go-go boots with 4″ heels. Then a curly brown wig, make-up, nails, jewelry, perfume & then I was off to the Halloween party. That was my first time going out dressed as a girl & my beginning of going out crossdressed.

    • avalana 6 years ago

      hi julia! sounds familiar except my sisters were the ones who liked me better dressed as a girl. i've continued it for over 52 years now cause it felt so right the first time why stop? it (i) just got better!

    • Warren 7 years ago

      Hi. I’m a tri-athlete and I love going out wearing micro race shorts to show off my legs and sports bra to show off my midriff. I have a slim but very trim body and shave my legs as other cyclists do so I think I look really good. I just came back from a solo ride and got whistled at and honked at so it was really exciting! I like this feeling of being feminine but at the same time I feel more sexually potent.

  23. Mardina 7 years ago

    Dear Julia sounds your very lucky When I was young I lived on Lake My parents renter cabins helping my ma. clean them I found a girls 2pice. I couldent wait to try it on later I did Then sliped a tee on over and down to beach Igrue up in the 60s I had long hair, there was a beach down the rd.when I got there I looked around to see if I new aynone. Then took off the Tee and played on the beach it was the best.

  24. penny 7 years ago

    Hi all i had to comment on first tip out . I was introduced to dressing at a halloween party , like so many of us. well i was 12 yo old and did not realize then that I wanted to be more fem than male type. As the years passed I started dressing more and more but never realy thought I could ever pass. A couple of years ago I happened to meet a dom cd on line, we made a date to meet up in her part of the state. I was ordered to arrive dressed , and not to bring any thing male with me. I drove across the state dressed enfem, and so scared that i was trembling non stop. Once I arrived at her home she took me shopping at a local fetish store she went to. I was tarrified as she told me to get out and go with her, once in side I acted as her personal servant, i was to serve customers in their friendship cafe area , coffee ect. After about an hour I was starting to reaalize that few people realy cared how i looked. Once I was feeling a little less scared , I was instructed to go find some new out fitts and try them on , a kind of fashion show for any one there . I ended up with a stunning pvc chambermaid out fit , which I still love to wear lol. Well my New domm friend took me out in puclic dressed of course and i found that noo one except me seemed to realize that I was not dressed the propper way for my gender . Now i dress more pften and try to go out as penny , god it is such a wonderful feeling dressing in the fem styles that I love . Thanks Penny

  25. Kevin 7 years ago

    I need help with this , come on girls give me some help how to dress hot!!

    • Tammy 5 years ago

      At this time I went to meet a friend crossdresser. I had to travel on the toll roads and yes the blood was running . I became more at ease when I went through a few booths . It was a diffrent way of life. would I go out again. Yes but I would like people to see there are people out there that are not trying to do anything wrong we just want to blend in too. Help us if you wish. Or leave us alone let us live are lifes are way as long as it isent getting into your life.

    • Lacey 6 years ago

      I'm wondering if dressing HOT by women is any different from a man dressing HOT. Opinions or ideas? As a qualification I have underdressed for 30 years.

    • sophie 7 years ago

      hi kevin sophie here i think tht it is upto you if u think something is hot then where it i have okay maybe it is slightly strange to see someone walking down the streets of corby in the middle of winter wearing a mini skirt but if u think it makes u look hot then why not? it also helps if u have someone hu can help u suck as a friend or girlfriend ect. so just really be yourself and where wot u think makes u hot

      • Racquel Lynn 7 years ago

        No doubt that is the right attitude to have. Just do what makes you happy and what you are comfortable with.
        I used to work at a bar and was always amazed at how little so many women would wear in the middle of winter just because they want to look like the hottest girl in the bar. They will totally risk Pneumonia for the sake of vanity.
        So if a genetic female can do it, why not us? Personally, I bundle up when it’s cold. 😉

  26. Patty 7 years ago

    am older and look silly but love it

  27. Mike 7 years ago

    My first time, I was 35 married in a boring marriage. I had connected with a woman who was a professional call girl. We connected on a non-sexual level and dated for over a year. She had a closet full of female clothing for her clients to wear. I had no idea other men like to cross-dress too. One evening she told me she was going to take me out. I was nervous, no I was scared. I’m 6’6”, and at the time had a 32 “ waste and 54” chest, not exactly the female looking type. She bought me a pair of woman’s jenas jeans, a beautiful blouse, wig, bra and she had already ordered a pair of 4” heels in my size. She dressed me, made me up, stuffed the bra she had for me and off we went in her car. We stopped at a gas station and she made me go in a pay. It was 10 pm at night but where she lived was still a fair amount of traffic, not to mention other folks pumping gas. Well off I went, strutting my stuff. I guess I was too big for the clerk to laugh at, he just stared. It was fairly dark, even under the station canopy, so you had to get pretty close to see my features. I did get a couple of double takes from passer bys. It was exciting. Later she worked on my walk, mannerisms, posture etc. She took me out several times fully dressed, a few in daylight. I became more and more used to it and felt very comfortable dressed, aside from my towering stature. We broke up, she moved on and I haven’t had the experience since. But it was wonderful, exciting and liberating.

  28. Sarah Rose LAMONT 7 years ago

    After fifty years as a closet crossdresser, two of my friends manged to coerce me into going out in public. Went to the beach and walked in the sand. Each time someone came toward us I looked away in case they spoke to me. I was frightened yet excited, when we returned home I was so pleased with myself.
    Next time was a month later and the same friend took me to a casual restaurant. I gave her the money as I did not want to speak.
    We sat down and had our meal quietly, then I held both her hands and
    cried and cried. That was when I realised that living full time was possible. Two years later I go everywhere, frequently I go to
    Karaoke bars and sing, yes I have a male voice, but nobody has yet
    treated me any differently from the other singers.
    I am fortunate to have a high level of confidence, I choose carefully what I wear when going out to ensure that I present as a convincing female of my age. Being part of a support group helps immensely.
    Thank you for reading my story.


    • Lost 6 years ago

      You are an inspiration to me. I am just finding myself, but it scares me to death. When I done my female self, I feel so inadequate and awkward. None of the womens clothing fits me right. I still have yet to go out in public. I'm too althelticaly built to pass it off properly. Reading your post has reminded me that careful wardrobe planning is ever more essential for us than a biological woman, Any tips or advice is appreciated. I posted below under "scared"

    • Vanessa Law 7 years ago

      Wonderful Sarah – that’s quite a testament to your courage. I’m so glad you found happiness in being who you are!

  29. Terri 6 years ago


    I can only dream of going dressed as a woman because i am trapped because I am handicaped and I have no way to get to any place, or to go to. I would love to get some help but whare is my question?

    If I could get the help that I need I would go to it?

    I would love to go out dreess as a woman the very first time but cannot. what are we to do?

    Thank you


    • J 5 years ago

      I’m really wanting to be turned into a cute girl, I’m 24, 6′ 3″, 160, long legs, cute face, long hair. I have been having this fantasy for the past few months and i really want to act on it! I live in Atlanta, GA. so if you are close and can turn me into a girl, please reply! thanks J.

    • jon 6 years ago

      im a crossdresser in bangladesh. i like women dress so much. i like to wear panty bra and other women dress. i want to meet other crossdresser

  30. jon 6 years ago

    im done

  31. Scared 6 years ago

    I struggle daily with my need to crossdress. I have always felt the feminie urge. Luckily I have a bi wife who is fine with it (took 2 years for me to tell her) and now that she's helping me with it I'm terrified. I in no way resemble a woman. I am just shy of 6', well muscled, but not overly so. I could maybe pull it off in a dark room but my chest and face…oh god, its so embarrasing. I have never told her how insecure I feel but seeing some of everyone else's stories gives me a little faith. I have tried dressing in sexy lingerie for her, but it never seems to do it for her. I feel so hopeless in this. I fell as if I should go back to just supressing the feelings. Any advice, be it fashoin, psychological, or otherwise would be greatly appreciated. I don't know what else to do….

  32. guesty guest 6 years ago

    I have a slightly more unique experience, I'm colby. I am a genderfluid, so when I dress contrary to my masculine body it's not cross dressing, it's simply expressing that which I am, a genderfluid, neither male nor female yet both. Anyhow. When I go out dressed, which used to be rather normal…every other day or so, I had no problem with it, except now which it's been a while since I did, mostly I've been forced to live with less accepting people. I go out and have to steel myself to be myself, and when i finally do if a car comes driving by I am afraid it's someone I know, or someone my family knows, so on and so forth. Writing this maybe it's not so different. My reasoning may be different but the effects are the same in general.

  33. jeanie 6 years ago

    ive gone out twice crossdressed onece for hollwen and once to adrive in move hollewen was no big deal the drive inmove was a lot more different i was nerve racking once i got too the city i was ok cause nobody new me i had a great time with my wife

  34. Ashlea 6 years ago

    My first time was 3 years ago. My wife took me to an inner city street full of pubs. Getting out of the car the first time terrifying but exciting at the same time. I was wearing a black net sleeved top, breast forms, jeans, boots, make up and a wig.

    Anyway, we walked past 4 pubs with groups of blokes standing around. I had to walk right through the middle of them!
    Scared to death I was, just waiting to get caught. Incredibly, I didn't get one double take!

    The feeling I got from passing was the best thing out! : )

  35. Elizabeth 6 years ago

    I made my first foray into the world, while dressed this morning at 1 AM. I was sitting at home, dressed (as is my usual wont in the privacy of my own home) and was out of cigarettes. I thought, "This craving will pass – I will wait until morning, and go out dressed in male clothing to get more." Finally, at about 1 o'clock, I could stand it no longer. I was craving nicotine in the worst way, and really did not want to cahnge, just to make a short run to the local convenience store. So, girdling my loins, in a manner of speaking – though I was wearing a four pad girdle at the time, so I suppose it was literal, as well – I walked out of the house and got in the car, and drove to WAWA for my fix.

    • Eizabeth 6 years ago

      I was not dressed "over the top" by any stretch. I was wearing black leggings, and a rust-colored jersey knit long sleeved dress, with a wide black stretchy belt. Conservative black 2" pumps on my feet, and a simple silver pendant completed the look. I had on very little makeup; just normal daytime concealer, mascara, eyebrow pencil, and lipstick in a subdued rust color that matched the dress. I carried a classic Coach shoulder bag. I thought the young lady at the counter had "clocked" me, but wasn't sure, because she said nothing while she was waiting on me. But as I was leaving, she said, quietly, "Have a nice evening, and remember to keep your shoulders down and back more, and loosen your arms a bit, Honey." It was so gratifying to have someone who was obviously "mainstream" be so accepting. So, my first "outing" was mostly uneventful, but I am certain I will always remember it, as long as I live.

  36. Jade 6 years ago

    Hello, I was born female and I saw this website advertised, I just want to say that I'm very supportive of men who cross-dress, a lot of people actually find it very attractive!! Don't ever be afraid to show who you are, if people mock you it's only because they're so ignorant, probrably from cultural views and follow what they've been brought up on, they haven't ever really made a decision based on their own heartfelt opinion.
    But yes, I would just like to add that I'm supportive of any men who crossdress as you should never, ever feel you have to be someone you're not 🙂

    • rya 6 years ago


  37. deepak 6 years ago

    hi i'm from india
    i want to be cross dresser
    is any one in chennai

    • Michelle 5 years ago

      Thank you, this article has helped me to go out in public for my first time. What an outstanding experience. Every woman I met at the hotel I was staying at, with helped me or some how encouraged me to dress up as a woman. I am in heaven. Thank you, Michelle

  38. Kerrie 6 years ago

    My first evening out came after a wonderful makeover at Janna's in Chicago.
    She did a remarkable job on my makeup and set me up with a new wig. I had picked out clothes for the past months in preparation for this night. Two other girls were made up at the same time and off we went to Hunters in Chicago. The evening was uneventful, chatting and drinks, but being totally enfemme was such a rush. I was totally hooked.

  39. Polly 6 years ago

    I’ve cr0ss-dressed since I was 13, but didn’t go ‘out’ until over 50. Yes, I was scared, but it was exciting & fun !
    Thanks for the article. Yours is the BEST c-d site in cyberspace

    • Vanessa Law 6 years ago

      Thanks Polly! Great to hear you finally made it out 🙂
      Feel free to tell others about Crossdresser Heaven if you feel it can provide some insight or encouragement to them.


  40. Polly 6 years ago

    I’ve cr0ss-dressed since I was 13, but didn’t go ‘out’ until over 50. Yes, I was scared, but it was exciting & fun !
    Thanks for the article. Yours is the BEST c-d site in cyberspace

    • Vanessa Law 6 years ago

      Thanks Polly! Great to hear you finally made it out 🙂
      Feel free to tell others about Crossdresser Heaven if you feel it can provide some insight or encouragement to them.


  41. Topdog1 5 years ago

    Hi I’m Paula, and I’ve been cross dressing most of my life. I never went out until I was 56 and I waited until Halloween, and I went out. I drove to a casino which I had planned on going inside to gamble. I arrived in the parking lot and I wanted to go inside so badly I could taste it but I just couldn’t. I ended up driving back home. Disappointed. Once again I’m going to try it again this Halloween, to see what happens. Thanks and still trying Paula.

    • Vanessa Law 5 years ago

      Good luck hon! Halloween is just around the corner. Remember, everyone will be wearing crazy costumes 🙂

  42. Cathy38c 5 years ago

    I go out everyday in a subtle way. I of course wear my bra and panties, but as outer wear, I wear women’s blue jeans, and a button down blouse, or a tee shirt. Foot wear in the summer can be sandals which do expose my painted toes. In the evening, if I go out for some adult entertainment, I might wear a cami, with a skirt.   

  43. Stephanie Kiss 5 years ago

    I have been dressing since I was twelve. But after college, I had the urge to do more than be by myself. So I checked into a hotel outside Pittsburgh, PA. I was so nervous! But in downtown I made an illegal right turn and got pulled over by a policeman. I always assumed that there were laws against crossdressing but there aren’t! He gave me a warning but then let me go. I was relieved! My soul was satisfied when as I was driving back into the hotel parking lot, a man gave me the “look.”

  44. Miriam 5 years ago

    Wow, the first time out, I do remember it well. I was 14 and how thrilling it was. Like most of us I started playing around with girls clothes and shoes at 11. I would try on my mom’s high heels and walk around the house. That sound that they make is so exciting. At 12 I was invited to a costume party by my cousin, She asked me to come as a girl. I told my mom and she went out to get me what I needed. It was a simple outfit, a blue party dress, white stockings and black maryjane flats. A little makeup and I was set. It was fun and it started to sink in that I really liked looking like a girl. My mom who always wanted a little girl was more then pleased. A little time went by and I would continue to wear her high heels at home, but the feelings were getting stronger. I told my mom that I wanted to do this more and she said she would help me.

    For my 14th. birthday to my surprise my mom bought me my first total all girl outfit. What a thrill it was. A red and green pleated skirt, a red wool vee neck sweater, a pair of 2 inch black pumps, light tan hose and a beige bra and panty set, a pair of gold earrings and a pearl necklace. My hair was pretty long so she added a false ponytail. now comes the best part, becoming a young girl. We planned on going out Saturday night as mother and daughter. She did my nails in red, made forms for me using beanbags so it looked like I had real breasts.I got into the panties and bra put on the stockings and heels then the skirt and sweater. She did my hair and put on just the little makeup I needed with some red lipstick. We added the jewelry and got set to go out. I looked in the mirror and thought, wow, this is really me.

    We got into the car a drove to a local diner for dinner, I was a little scared, but, my mom was with me and she said no one will know that your not a girl. Nobody at the diner knew and we had a great time. We drove to the movie, and by this time I was feeling very confident about myself. As we waited in line to get our seats two older boys came by and whistled at me, wow, what a thrill, if they had only known. it was a great night that I will always remember. By the time I was 16 I was buying all my own outfits and dressing everyday after school and almost every weekend. I am now 95% girl and 5% boy. I really hope and pray that they never stop making high heels, what would I ever do if that happened.


  45. pippa white 4 years ago

    The first time I ventured out as Pippa was while on holiday just outside the coastal town of Ilfracombe.
    My wife is well aware that I dress and in fact it is when we’re on holiday that we are most relaxed about it, as there is no fear of being disturbed by any family members. I had already mentioned to her that I wanted to try and capture a nice sunset and as a keen photographer it raised no suspicions of wanting to be on my own for an hour or so.
    I showered and put on my undies and a short dress before covering them with my jeans and shirt. I was worried that it looked too bulky but she didn’t notice. After packing a few other things into my camera bag I set off down the road to a discreet pull-in that I had noticed earlier that day. It was on a steep hill leading down into the town. A couple were walking up the hill towards the pull-in but it was a fairly steep climb so I knew it would take them some time to get near me.
    Swiftly removing my jeans and shirt I smoothed down my dress and put on a pair of heels I checked my wig making sure it was straight and added a bit of light makeup and my necklace and earrings, the couple were less than 20 metres from where I was parked when I drove away, although they would have still been able to see me as I drove past,
    I carried on down the road and took the first turning into the town and was went along feeling really happy to be out driving as Pippa. What I should have realised is that like most towns there are road narrowing places and humps to slow down speeding motorists which meant that I was constantly stopping or going at a crawl giving other drivers and pedestrians time to look in and see me, and I couldn’t believe how busy that sleepy little town had become when the sun began to set. As it was a one-way system I had no option other than go with the flow and I have to say that my excitement did give way to being a bit scared but I have no idea why I was so scared. I eventually emerged at the other end of town and drove back towards our holiday home. By now it was very dark, there were no street lights around and I managed to find somewhere to pull in and change back into my drab clothes and remove me makeup.
    I didn’t get any sunsets pictures and made some pathetic excuse about the light being all wrong. I have probably been out driving en-femme thirty times or more since that day and its always a mix of excitement and trepidation. Not quite certain as to why I have this need to expose myself in this way and of course the more we do things the greater the risk of being caught. Pippa

  46. Danielle True 4 years ago

    First Time out.
    I resolved a long time ago that I was a crossdresser. I had tried, and failed many times to quit. I had accumulated and purged complete wardrobes. I had prayed many many rimes that God take this need away, and each time He answered that His Grace was sufficient. So I finally accepted that I am, and always will be, a crossdresser, and that God loves me just as I am. I have forgiven myself, and now even love myself. So I shopped. As a guy, I would shop the smaller boutiques and clothing stores. Always as a guy. I would always ask if they had a problem with a guy looking, buying, and perhaps even trying on dresses, maybe bras, lingerie. After a while, after I had established a rapport, I would bring breast forms and heels in a bag, and wear panties, bra, garter belt and stockings under my boy clothes. I would arrive just before closing, and they would lock up and let me shop and model what I tried on. I did this at Lane Bryant, Dress Barn, Fashion Bug and some other independent shops. Then I started to frequent the makeup counters at Nordstrom. Still as a guy. I learned my colors and had mini makeovers. Finally it was time. I was invited to a New Years Eve party at a community church which accepts gay and trans people with open arms. I made an appointment at the MAC counter at Nordstrom for a full makeover and an appointment at a nail salon for a manicure and pedicure. I wore a white satin blouse and a black print skirt, long brown wig, light makeup to Nordstroms for my makeover. I arrived at about 3pm. Middle of the day. BRIGHT sunshine. I actually had to step out of the car dressed as a woman! I was terrified. I managed to get into the store and had my makeover. I felt so much better with evening makeup on. I then went to the nail salon where I had been many times before as a guy. When I walked in, the owner asked if she could help me from her station across the room. Then she paused, recognized me, and shouted my boy name across the salon excitedly. I was seated next to a woman I had seen before. She was very impressed and complementary. I finished, went home and changed into my gown. I had to drive 40 miles en femme, wearing 3 inch heels to get to the party. It was fabulous!! There was only one other CD there.
    I have other adventures to share.
    Danielle True

  47. kim pappas 4 years ago

    I am new to crossdressing need help

  48. kaylee 4 years ago

    my first time out was on halloween. I drove an hour to our state capitol city. I parked in a downtown parking ramp with a suit case filled with my favorite outfit, makeup, wig and heels.I wore a grey sweater with flare leg jeans and matte black 5 inch heels. A blonde wig with a black beanie hat, and a black purse. my makeup turned out great and I knew I was very passable.I left my vehicle, walked down the stairs and onto the sidewalk. My heart was pounding a million miles an hour.I walked around the capitol buiding where the farmers market was going on. no one suspected a thing. I was so excited and nervous at the same time.It was like being in a hazy dream. The only feeling I can compare it to. is the first time I had sex. The capitol building was open to vistiors so decided to get away from the large crowd of people. I walked down the marble floor hallways of the capitol and my heels sounded AWESOME. I spent about an hour in the building admiring its beauty. I was on the second floor balcony looking up at the massive dome about eight stories above me, when two men in their 30s passed me. They were givng me a good look up and down. I really got nervous. After they passed, I heard one of them say ” WOW,SHE’S HOT”. I knew then, that I had nailed it. I left and went to a lgbt bar I had heard about and enjoyed a few stiff drinks. The rest of the day, I just enjoyed being kaylee. The only bad part of the day was that I got a huge blister on my big toe from my stilettoes.

  49. Michelle Hart 4 years ago

    My first time was in my teens. I had moved and was living with my Father and step-mother. I was given the chores that normally she would do but because they used to get home late almost every day, I became the housewife and Mother to my three step-brothers. While doing the laundry, I discovered that she was my size and I started wearing her clothes (mostly her jeans and blouses). I already had my own undies but I did wear the sexy lace bras and panties I knew she never did.

    It was a girl at my school that became my best friend and confidaunt. The first time I met her, she informed me that my bra showed through my tee shirt. After school that day, we sat down and I opened up for the first time in my life to someone else. I was like the flood gates were opened and I was never going to allow them to close. We used to go shopping together, would talk about all the things that a normal teeaged girl would talk about. Yes that also meant talking about dating boys and guys.

    It was my friend that convinced me to go out with a guy that we knew from school. I went over to her house, the night of my date and she helped me get ready. I borrowed a cute dress and she helped me with my makeup and hair. It was so wonderful to finally be the true me. It was magical on my date. He treated my like a true woman. All the way up to the good night kiss at the door. I was in heaven.

  50. kris 4 years ago

    for some time i have been getting dressed up in my shop after hours and i will jump in the car fast because im still scared, love riding around in the car with a skirt or dress, i have teenagers @ home so i’m not sure yet about going home but the time riding around in public helps, its very exciting ! one of these days i’ll run into a friend to go out with and make it easier>

  51. Melody Grace 4 years ago

    The first time I cross dressed outside was at high school on break up day. It was sort of a traditional thing that happened every year. I wore a friends catholic school girl uniform. So Awesome! Have a bunch of my own now!

    Melody ♥

  52. Joyce 4 years ago

    The first time I went out I went to the crosdresser friendly store where I bought all my stuff at the time. I was nervous. and when I asked if I was passing she said “No” I totally lost my confidence and changed my clothes in her dressing room. Gosh!!! I am going out today and it is the first time in 7 years and I am starting to get cold feet. Help me please.

  53. Jamee 4 years ago

    I have been dressing for a long time, but I still find at times that are uncomfortable stares. I also found that one of the best places to ‘get out of the closet’ for the first time is a casino like in Alantic City they don’t pay much attention to you, they are more interested in their gambleing – but you get confidence

  54. Joyce 4 years ago

    I have been out as myself 4 times now since I wrote the paragraph on October 9th. The first time I was awake for half the night thinking about it. And I got in my mind that I wanted to go to Dots where I bought my boots. I was wearing my new sweater dress. My new boots and various under clothes including breast forms and smoothing shape wear. Well I gave them a call from the parking lot and when I talked to Robin. She said sure You’re fine. I felt so good.Robin was her usual bubbly self and treated me so nice that I felt like a real girl. I will never forget that and I frequently shop there as a man and as a woman. Every time I think of it i could burst with pride.

  55. Abbeygirl 4 years ago

    MY wife and i went out i was dressd enfemme we snuck out the door at nite to go for a ride to go see my brother he is gay and he knows my fetish but hasnt seem me yet dressed anyway my wife is drving my van and im in passdnges seat in a pretty 1 pc flower print dress when a deer runs out in frnt of us needless to say it died and we had to cal the police and im stil dressed SO EXCITING wow!

    • kris 4 years ago

      thats my type of luck, makes me nervous when i ride around dressed, but its the only way i can dress up. thats a funning story, good luck

  56. Abbeygirl 4 years ago

    Would love t o have a cd to chat with and try on clothes with

    • kris 4 years ago

      i understand what you are asking, i have been looking too, all the people i find want money for services and i not looking for that i love dressing and it would be nice to have a friend not a service

  57. Alicia 4 years ago

    i was wondering i been going out dressed as a female the only problem i have my Boobs they stick out really good hard to miss when we are driving i am fine but when i get to the store or where ever i get scared some one will notices my breast my breast are real not forms can anybody help me to get over that anything you can tell me will help thank you

    • Michelle 4 years ago

      Alicia, if you are dressed as woman act like one and be proud of what you have naturally. I know quite a few others than would envy not having to wear forms or padded bras to accomplish the look of breasts.
      I understand what you are saying about the difference between driving and being out in the open. In the car you have that feeling of safety but when in a public place you become frightened. Don’t be! Be proud to let others see you as the woman you are. Straighten your posture, shoulders back and show them off like any woman would.

  58. Barb 4 years ago

    My first time out was to visit a professional photographer.
    I posed very amateurishly but learned a lot about myself and my appearance.
    The photographer was great and I was allowed to take my time and pose in various outfits.
    It confirmed that I am passable even without any makeup.
    I need to learn good makeup as that would really make the total package.
    It was a very exciting experience, especially when guys peeked with obvious interest….
    I would love to go to a CD friendly bar or nightclub.

    • Nyssa Marie 4 years ago

      Hi Vanessa! I just linked this article onto my website. I was so nervous the first time I actually got up the courage to walk out of my house!

      It wasn’t far, and I was dressed horribly. It was raining outside and I needed to bring in a trashcan. I was wearing a sports bra, pantyhose and a pair of green shorts. I went running out to get the bin, and realized I was actually outside! I stood still for a couple of seconds, enjoying the feeling of being out. Then I heard a sound from one of the neighbor’s houses and ran as fast as I could to get back in. 🙂

  59. Barb 4 years ago

    I was recently trying out my very sexy new 4 inch heel thigh highs and managed to twinge something in my ankle or foot to cause major pain and swelling.
    Of course I could not tell everyone how it happened……
    I had always worn 3 inch heels so yesterday I purchased new four inch high heels to get accustomed.
    Indeed they feel very nice and walked around in them for about a half hour with no ill effect.

  60. Blake 4 years ago

    You can face the fear of it and to just do it.Get it done.Its not really that bad of thing to do.It’s fun really.I get alot women complimenting me on the skirts i wear,or the boot and so on.I have always dressed on the feminine side.But for me,it feels like this is the way it should be.I do not feel that “weirdness” or “uncomfortable” feeling that im sure guys get when they go into the public view.I had one person ask me “where do you go dressed like that” ? I then said, “where do you go when you are wearing jeans and tennis shoes”? Do you
    see my point ? Just BE yourself when dressed as you are when dressed feminine.And personally hate that word ‘cross dressing’.
    Its sounds degrading,and freakish,like NON of us are.Its the way are DNA make is like i always say


  61. Diane 3 years ago

    I have been cross dressing for nearly thirty some years and in the closet all of that time. My wife left to go see our daughter on the west coast of course as soon as she left I needed to get dressed and did so. Stayed dress all day in the house tho and it was really fun just to be dressed in those cloths. I had only about a month before gotten my first set of breast forms and I think that is what made it so special for me on that day. At any rate it was early spring and the days still were kind a short. So toward evening. I took off my the dress and underthings, took a bath and shave my legs. Got redressed in some new lingerie and had gotten along with those breasts forms. I sat down at my wife’ make up table and redid it ( I had been doing make up for a number of years and am pretty good at getting the look I wanted). I got done with that and went to my stash which was somewhat limited but got a black skirt and a cream colored blouse and sweater put it on feeling very much a lady, I put on my three inch black heels and just felt so good. I walked around the living room for a while thinking about what I was about to do made, a couple of trips to the door but didn’t open it. Just stood there wondering if I should venture out sort getting myself primed up I guess. Finally I got a light jacket and a black purse out of the closet and put it on open the garage door and got in the car, sat there for another couple of minutes deciding just what I wanted to do, started the engine and back out, drove down the driveway. Our home sits back off the main road so we do have a pretty long driveway. Got to the street and turned going toward town. Now I hadn’t eaten much all day and it seemed to have caught up with me. Just driving and feeling all those nice cloths on my body has sort of relax me and the feeling of hunger grew stronger I thought I could go someplace and get something to eat. The next thing I knew I had turned into the Mc Donald’s and got into the drive thru lane and ordered a hamberger baskets and a cola. When the girl said pull forward I sort a panic what would she think of me dressed like this and those thoughts ran ramped until I got near the window. I stop got my purse from the seat next to me and got out my billfold she said the price I turned toward her she smiled and I gave her the money she said something about needing some ones and disappeared, came back shortly handed me the food which I took and was about to go when she said, miss you have change. I was almost ready to leave she smiled again and gave me what I had coming, then said thank you and have a nice evening. I drove out of there and went to the park eat my burger and fries. When I finished I repair my lipstick in the car, got out and walked around the park it was early evening and mild, it felt so good just to feel so nice. I just about got to my car when a couple came along and stopped right next to drivers side door and when I got to the curb and stepped off between the cars the girl started to open her passenger side door then look up at me and held in close until I got in she then step out and smiled at me and sort a waved like she knew me. I smile back and started my car and back out of the parking place. When I put in drive I looked back at her she was looking at me smiled, I really don’t know if she had read me or just being friendly. I then went to the mall thinking that I would like to go inside and go to a movie Just to see if I could pull that off too, I sat there for about a half hour. Knowing what time the movie I wanted to see was going to end and the next one would start and wondering just how to go about buying the ticket, not do a lot of talking. Well the time came and I felt pretty confinedent got out pulled my jacket a bit tighter and walked into the mall entrance, from there to the ticket booth seemed to me at least a mile and a half away and the crowd was coming out past me. Listening to the click of my high heels, I just smile and kept my head up looking at all those folks. All the time wondering if I was pulling off the woman I felt I was, Anyway I got to the ticket counter and asked of one adult to, Mission Impossible, the girl didn’t look up just gave me my ticket and change and told me which theater it was playing in, smile and look right passed me to the next couple in line. I walked to the theater and found a seat and sat down, with the feeling of everyone who came in look right at me but after a few minutes the feeling of them looking gave way, to feeling so good about just being there. The movie started and it was very intense and about half way thru of course the drink I had gotten from Mc Donalds had to come out. I got up now what to do I really needed to pee and the lobby was empty so I guess dressed as I was I would use the ladies room so entered and did my business and washed my hands redid my lips again and went back the the movie. Setting down again as I did I notice the couple that had parked next to me at the park were two rows back of me. Wow now this will be interesting, if she remembers me. The movie ended kind of abruptly and sort of surprise me. I got to my feet and as I leaving my isle, when she came down the step and just smiled again when she went by her friend sort of waited for me and I justured for him to go ahead he smile and said nice to see you again this evening, so he surely had either talk to her about me during the movie or had seem me when he parked next to me as well. At any rate that was all that was to that. I walked out of the mall which seemed much shorter got into my car and went home. Much to my surprise everything had gone so great I dressed on Sunday again and every day during my wife’s absence the next two weeks. I did go out several times after that evening twice during the day which was way more of a challenge for me but seemed to be OK events too. Diane

    • belinda smith 2 years ago

      beautiful story <3

  62. Blake 3 years ago

    to Diane,
    Just be you and go out dressed and do the things you would be doing if not looking female…i do..i only have female clothes.
    Just Do It ! ! ! you only have one life to live,so live it the way YOU want to,

  63. Barb 3 years ago


    I, and I am sure many other closet cases out here just loved and experienced empathy with your outing story.

    In my case I have visited a professional photographer who indeed was good to me, and I have done similar under the radar outings all dressed up.

    How exiting those outings were!

    But normally I am restricted to less than one hour ventures when I get that time alone.

    This means I am able to don the finery and strut around for a while and then it all comes off and goes back into storage.

    Today I worked on rebuilding the pool pump in my workshop wearing just a pair of shorts and very sexy satin four inch high heels.

    I enjoy every moment I can…..


  64. Karen 3 years ago

    Like many others, I’ll never forget my first time dressed out in the real world. I had been dressing for so many years and never having the oppertunity to go out en femme. Then one day after a snowstorm, the snow was shoveled from the sidewalks, but there was still icy patches in spots, and needing money from the bank, I decided to go out and just do it! Dressed that is, so I donned a pink running suit, some subtle make-up, page boy wig, white sneakers with pink accents, and a white goose down vest jacket, I headed off to the bank. After parking the car about a half block away (no parking lots, just street parking in this area)I sat there debating whether I should get out or just go back home. Well, I decided to go for it, and got out. Walking to the bank, passing people, I was a nervous wreck, but nobody paid me any attention so my confidence grew and I relaxed a bit. Walking to the front door of the bank, a man got ther just ahead of me and then…..Lo and behold!, he held the door for me and allowed me to enter first!!, I smiled at him and nodded my thanks and he returned the smile. I went to the ATM and he entered the bank proper. Now I was on cloud nine, nerves just about gone and replaced by elation! After leaving the bank and walking back to my car. though most of the sidewalk was clear of snow, there were patches that the sidewalk was narrow and icy, and this where my second moment of elation occured, a man coming the opposite direction, stepped into the snow and held out his hand to assist me through the narrow and icy path!…I was so excited, I thought I would orgasm right there! (I didn’t though). This little adventure was the start for me in going out in public en femme, though they are infrequent, they are still exciting and enjoyable.

  65. Blake 3 years ago

    to Karen,
    What a great feeling that is uh Karen ?!Do that everyday and it wont become difficult to out dressed……I do,EVERYWHERE i go,normal part of life for me.. Way to go Karen ! ! !

  66. stephanie 3 years ago

    Just went out for the first time today. Put on my makeup and hair. Got dressed. Sat around for hours imagining what could go wrong, then said “to heck with it!” and did it! SUCCESS! Why did I wait till I was 59?! God, I had fun!

  67. charlotte 3 years ago

    Also had been dressing for years and years, never felt confident enough to go out. 6 years ago I started looking at some pictures of myself and realized I could pull it off if I dressed conservative and low key. So I planned everything out. Worst part was I live in an apartment with a doorman and I had to get in and out past him! Luckily if you come and go with a key, they don’t ask questions. So I get all shaved and dressed, not too much makeup popped a xanax and out I went and it was surreal. I was watching to see if anybody looked at me funny but no, I was doing OK. Finally I got up the nerve to go into a store and buy something, and someone referred to me as “she” – then I figured for sure all was well. Since then I go out every weekend, and I’ve gotten more and more daring – different fashions, long hair, heavier makeup – but never a problem except once, when I was careless and got read a few times – so I head home quick!

  68. Gabriela Almeida 3 years ago

    I have read the post and the comments with pleasure and sympathy. In my case in take refuge in my car(rather late at night) but in my way to it I felt the exhilarate experience of the wind in my legs(I was wearing knee high dress) , that give my the courage to keep going, after drive for a while, fearing to by stopped by the police, I parked in a popular street and walk around the block…guess what?, I don’t know if I was figure out, or not… but nobody cared…an exhilarating feeling. I only regret non having enough practice with high heels. Not having an excuse to stay there I went to a convenience store and bought a bottle of water, very nervous about facing the cashier…again, no reaction.
    Conclusion: get out, be your self, you are going to be noticed by the ones that are attracted by you

  69. Monique 2 years ago

    I had been planning to go out as a woman for some time but it never got psst the thinking and reading stage. But last week while driving alone in camp clothes I bought lipstick and put it on for the first time. It was easy and beautiful. Then I screwedup my courage, put on sunglasses and a floppy camp hat to cover my male head of hair and parked in a casino lot. I got out strode into the casino in the best girl walk I could manage, wandered around a bit and went back. I don’t think anyone gave me a glance, let alone wonder what Mix Hot Lips here was up to. Can’t wait to try it again, this time in a skirt! Its easy girls!

    • Profile photo of Vanessa Law Author
      Vanessa Law 2 years ago

      You go girl! Yah Monique!!
      I’m so proud that you were able to gather your courage and follow through – little steps one at a time is all it takes. Hugs.

  70. Terri 1 year ago

    My first time out in fem clothes I drove by myself in my truck. My destination was about 500 mile away. I was certainly not dressed conservatively, actually I was dressed pretty sluttty. I had on a see through blouse which revealed my black bra (with breast enhancers) and a miniskirt hiked up to reveal the top s of my stockings and garters.I can hardly describe the rush. But I know those of you who have dressed and gone out in public understand. I drew the attention of many semi truck drivers and occasionally one would honk. 🙂 I did stop at a gas station to fill up the tank. Again I felt anxious and hoped I would not draw too much attention. But dressed like I was what should I expect. I eventually reached my destination. Once since that time I did go out at night dressed and went to a gay bar. Had hoped to get picked up, but was not very lucky.

  71. Aileen 1 year ago

    Similarly to others I’ve been staying inside our home when dressed en femme. Recently I went on travel. I took along my lady things intending to spend the evenings in my motel room practicing wardrobe and makeup. I worked up some courage, grabbed my room key, and stepped out into the hallway. No one was there, so I walked down the hallway intending to do an about face and return to my room if anyone appeared. No one! I went to the lobby, still no one around. I got a cup of decaf and returned to the room. I was exhilarated! I went back out the door and took the stairs to the second floor. I walked down that hallway and met the first person other than my wife to see me as Aileen. She was one of the housekeeping staff and gave me a big smile and hello. I smiled and hello’ed back. I took the stairs up a flight and walked the third floor hallway, back to the second, back to the first. Along the way I met several other people who either greeted me with a smile and hello, or ignored me. I stopped poolside for a few minutes and watched the kids splashing. Several of the parents made eye contact but no one pointed, laughed or screamed. It felt so incredibly good.

  72. Ashleigh Parker 1 year ago

    Funny you should mention about the police. We are our own worst enemy when it comes to worrying about being “found out”. We always assume people are more observant than they really are.
    My first real experience was similar. I, like most everyone else, had/have been dressing in the privacy of my own home since I can remember. I did venture out once in my early twenties with a very short skirt, sweater type jacket, bra stuffed with socks, and panty hose that did not fit well (all my wife’s things). I had a scarf wrapped around my head and face as I still sported a full beard. I laughed when I read the part about hurrying out of the apartment building as quickly as possible, exact same scenario for me. I took a rather brisk walk around the block and nearly ran back up 3 flights of stairs to my apartment. However, during my walk, I passed a couple young men standing on the sidewalk. Low and behold, nobody laughed, in fact one of them whistled at me! Loved that attention.
    The first real time out was only a little over 1 year ago. I too had gotten hooked up with a trans-lady group. They were to have their Spring Soiree on the same weekend that my wife was going to be out of town. I made arrangements to attend not only the Soiree, but dinner with another lady from the group. She was very patient and kind knowing this was to be my debut, so to speak. I got fully dressed, wig, makeup, stockings, heels, everything. Things have changed a bit since that very scary time nearly 30 years ago. I now have all my own clothes, wigs, breast forms, makeup, etc. Anyway, into my car I go in broad daylight through my very crowded subdivision on a Saturday afternoon in May. Lots of people out in their yards. Nobody gave me a second look, and they all know both me and my wife!
    75 miles north to Washington DC. The longer I drove in the stop and go traffic, the more confident I became in the fact that nobody knew, nor did they care that I was not a woman. I was absolutely convinced at first that everybody was staring and laughing, so refused to make eye contact. As my confidence grew, I began to make eye contact and even smile at other drivers.
    Now, my greatest fear was a car accident. To make matters worse in that respect, in the lane next to mine, a car almost identical to mine was rear ended by someone not paying attention! I had not even thought to bring any male clothes to change into in case of emergency. I pictured myself in the back of a police car trying to explain myself and my attire. Talk about paranoia setting in.
    Long story (not so) short, I made it safely to the restaurant, parked my car, walked to the self service pay station for the parking lot, and then down the street with my new friend Julie to the restaurant where we had a lovely dinner and then on to the soiree. Scariest and most fun experience of my life.
    I have ventured out a few times since, but no experience will match that first real time. I learned soooooo much about myself and the self absorbed attitude of most of the people we come into contact with.

    • Profile photo of Vanessa Law Author
      Vanessa Law 1 year ago

      It’s heartening to hear I’m not alone in my first time fears Ashleigh 🙂 What a crazy awesome story, thanks for sharing!

  73. Maxine 1 year ago

    My story is a little different in that I hadn’t been dressing all that long but with the full support and encouragement of my (new) partner.
    At the beginning of a 6 week holiday to New Zealand, we decided to remove all my body hair which we did with great success. We practiced the makeup & wig, getting the clothes right & walking for a while before venturing out the first time so by the time it happened, my confidence was reasonable. Although still mindfull of many things that could go wrong, I had the opinion that we should aim for me to be “passable” from a distance in low light. To this end, we ventured out around dusk and walked around the local lake, passing a few people walking in the other direction. Nothing untoward occurred and my confidence grew. It felt great! I was actually smiling. My partner, on the other hand, was so nervous that we had to make a pit stop back where we were staying so she could “relieve the tension” before going on to a slightly more populated area where we again walked a bit before returning home.
    Thinking back now, the whole episode was quite ametuerish and I now have a much more appropriate wardrobe, a far better wig and have developed the makeup & walking skills to blend in better, however, that first expedition was invaluable in giving us confidence to venture out again,something we now do on a semi-regular basis. We are looking forward to a planned road trip in the next few weeks. So exciting!
    Just a note on Police. On a subsequent outing back home in Australia (perhaps the 3rd or 4th) we were driving to a public area we intended to walk around. On the way there we encountered a random breath testing station. Whist this was unexpected and very daunting initially, I had no choice but to pull over, wind down my window and blow in the bag as required. The young (female) police officer was totally professional and said nothing. She may have said something to her colleagues after we left. Who knows? Who cares? It showed me that we are way more sensitive to our situation than most of the people around us and even if someone becomes aware, more often than not, they are ambivalent about it.

    • Profile photo of Vanessa Law Author
      Vanessa Law 1 year ago

      A beautiful memory Maxine! Thanks for sharing – phew, I know all about cops and first times 🙂 Glad you got through it!

  74. Erin 1 year ago

    The first time I went out dressed was last August to go a friends birthday, it was at a bar, and it was going to be like 80+ people. One of my friends convinced me to go dressed, I was scared I said no like 10 times but eventually I said yes, I know how to do make up and had alot of clothes and shoes but I just never wore them outside, I was always scared. But after that night I never wanted to dress in male attire anymore. I thought the whole room was going to get awkwardly silent, but it wasn’t anything like that. A few people I knew looked shocked but not in a bad way, they thought I looked cute. But the thing that really made me feel good was that nobody was being rude staring or laughing at me, everybody was just being normal having a good time and I certainly did that night. After that I made up my mind, I’m going to dress how I want to from then on. After going out a few times to a few clubs and bars I decided, one day to go out during the daytime hours. So I went to the local shopping center during noon to run errands, it was a hot day, I was wearing a white top capri jeans and like more then half of the people I saw down the isles couldn’t tell or didn’t care which is good.
    After that I kept on pushing myself to go out into the world and not worry what people think, and eveytime I did I felt more positive,
    It’s been 9 months already and ive been dressing everyday living my life the way I want to.

    • Profile photo of Vanessa Law Author
      Vanessa Law 1 year ago

      Erin that’s wonderful to hear! I’m delighted with how you’ve embraced your inner woman!

  75. Christine Charland 1 year ago

    There was a time when going out en femme scared the hell out of me. I try to see why I was so afraid back then and there were many reasons but most of them go back to how I was brought up. Sound familiar?

    Dad and boys and all that macho stuff that just doesn’t look good on your sleeve. I’m not going to write a book here about how i got beyond everything because……well it’s different for everyone. It does help to have some support and that I can do.

    I came out to family over 20 years ago. Tough thing to do but it was so worth it. A lot has changed since then. I want to make it clear that no one else changed since then. I did though. How I dressed and identified wasn’t quite as important as I sometimes made it out to be. It’s still a hard thing to take home every night and maybe it always will be. But you have to know that it’s not the end of the world. Don’t mean to sound cliche about that but girls you have more already than you think.

    So today, I don’t have a friend that doesn’t know I’m transgender. I still work in drab. Not sure why. Everyone I work with knows I’m transgender.

    It’s a great time to be transgender.

    Live to Love…..Love to Live

    Christine Charland
    Transgender Insight

    • Profile photo of Vanessa Law Author
      Vanessa Law 1 year ago

      Thanks for sharing Christine – it’s a blessing that we have people like you in our community!

  76. Caroline 1 year ago

    What a lovely piece, Vanessa, and how identical a story to many of ours’. As I live on a small island, it was always difficult for me and the situation was made worse by two facts: 1. my wife did not know anything in the first few years and 2. my work is in the public forefront, so it is always a risk being identified.

    My first outing was in the UK during one of my frequent visits there. Girlfriends and sisters within the Beaumont Society helped me prepare but I was still terrified. My first public “appearance” was for dinner at a tv-friendly restaurant where for the first time I was addressed as “madame” and had doors opened for me as I walked past in my high heels and evening dress. From then on, my stays in the UK have always been en femme and today I find it easy going into department stores, boutiques and and trying and buying things.

    But the misery back home persisted, until one night my wife jokingly asked me to put on the bra she had just taken off and it was obvious to both of us that very instant I wouldn’t take it off. We had the best loving session ever, followed by a confession of my feminine self. It wasn’t easy for my wife, but she eventually began to understand how important it is to me and to our relationship. That is when we started shopping for things together and I became Caroline indoors – at least when our two daughters were not in. We promised each other not to tell them to avoid further complications.
    But the urge to go out and to mix with the people in the street was too strong, and finally I begged my better half to let me do it. We finally agreed. I was lucky to have her helping me with the make-up and the things to wear, particularly shoes as while I wanted to storm out in three-inch-high stilettos, she advised me to go for a two-inch heel and be just a six-foot lady out and about! Of course she won and I have never regretted it.
    But to say I was terrified on my first going out in our neighbourhood is an understatement. My wife was going through the same turmoil back home, praying I do not get into any ugly situation. I did not and have never had any problems going out. The fears and trepidations still remain every time I go out, but it helps for me to avoid going into exaggerations such as going into pubs and restaurants on my own.
    I’d like to use this forum to thank my wife for accepting this other woman in her home and you for providing us with this opportunity to talk and discuss things that are important to all of us women and those who feel to be women despite Nature’s cruel jokes…..

    • Profile photo of Vanessa Law Author
      Vanessa Law 1 year ago

      What a beautiful story Caroline! Would you mind if I featured it more prominently on Crossdresser Heaven? If you have a photo you’d like to share as well that would be wonderful – you can submit your photo here.

      • Caroline 1 year ago

        Of course, please go ahead, Vanessa. Unfortunately I cannot submit a picture due mainly to the reasons referred to in my short piece. Love and peace.

  77. Charllotte Kerr-Scott 1 year ago

    For most of my life, from the time I was about 8 years old, I just so wanted to look like a girl and to walk about wearing girly things. This was in the late 1950s so you can imagine that it was a fantasy dream in those days. Gradually, attitudes and opportunities have changed. Around 10 years ago I went to a cross-dressing agency, in London, I had found in a magazine. They had me out, fully made-up, dressed in high heeled boots, smart skirt and jacket, checking into my hotel and walking down Oxford Street in London doing Christmas shopping that very day! I have hardly ever have looked back. I did have a day, about three years ago, when I went out and it just didn’t feel as good – no comments or anything but something didn’t feel right.

    A Tgirl friend suggested I go to a very upmarket and expensive cross- dressing agency in Windsor (sadly no longer operating) – One of the owners had been a fashion model – she stripped my body language back and made me concentrate on walking, mannerisms, voice and, most importantly, attitude! I went out that night a new girl! For me, getting those items right makes me feel more girly than I have ever done. I can walk in the highest of heels; I wear short skirts; I wear jeans; business suits or just slop around in leggings but those lessons are the most important I think I have learnt.

    To those who say to you, ‘ just go and do it’ I would say that is good advice but make sure that you prepare properly. Always when going out have a plan (and a Plan B and a Plan C etc. etc.) don’t just walk about and then walk back. Dress appropriately; look people straight in the eye and, most importantly of all, SMILE and enjoy yourself!

    I sat on a high stool in a local pub the other night, dressed in a skimpy top, black short skirt, 5inch black high heels, hair in an upsweep and big gold earrings; showing my legs off and chatting to the locals. All of a sudden I remembered those days when I was young and so wanted to exactly what I was doing! It seemed right to say a silent ‘thank you’ to all those who have helped me get here. Its been a fabulous journey.

  78. krnharris 1 year ago

    I am so afraid of telling everyone of my first time out because it was so many, many years ago.
    My wife was going to be gone on business for a week so I decided to take that same week as a vacation week. I was so excited and scared at the same time. I planned each day and what I was HOPING I could do but of course this did not entirely work out. What with my wife calling and a couple of friends coming over un-expected it was not quite how I had envisioned it.
    At any rate, lets get on to the good stuff. I started going out in the evening in my car driving around my home city. I was scared, but I drove the speed limit and obeyed the driving laws so as not to be pulled over. The first time I went out this way, I was so excited. I was dressed in a dress, pantyhose, shoes, make-up (light with lipstick) and a wig that my wife had. I drove around and had no problem, got home and was SO EXCITED!!!! This went on a couple more evenings and was very excited, nervous and did I mention EXCITED??
    This was so much fun. I spent some time writing a note to my wife explaining as much as I could about my being a Cross Dresser and what it meant to me and telling her that I still loved her etc., etc.
    The last night before she was to return, I got dressed a little earlier and was determined that I was going all the way and go to a to a shopping mall and walk around. I went to a mall a distance from my home, got out of my car (still light outside) and proceeded to head for the mall doorway. I got there and a “gentleman” held the door for me (SO COOL) and I walked in to JC Penny’s store and proceeded to go over to the dresses and women’s clothes are which by blind luck was the first department I entered. I glanced around and no one was paying any attention to me so getting up a little more courage, I proceeded to look at some of the ladies clothes. This was working perfect until a little girl about 10 or 11 came up to me and started to point and laugh at me. Let’s face it, she could spot me for a man dressed as a woman a mile away. (those darn little girls) Ha!Ha! That ended my “shopping trip” and I left before any more commotion could be created by this girl.
    I returned home and for some reason I could not get SUPER excited like before and my wife was coming home the next day and it all seemed so hopeless.
    This was MANY years ago and I am now 72 years old and I am in my last few years of life.
    Vanessa, if you would like me to go on I will, but the rest is sort of DRY.

    Karen Marie

  79. Amanda Trane 1 year ago

    That oh so scary, yet oh so exciting first time out. For me it was scarier to stay inside as my GF’s daughter had woken up and come out to get a glass of water after I had gotten dressed, done my face, and sprayed my hair into submission to relax for a few hours ‘enfemme’ as after a few days of babysitting for her I knew the kids never woke up.
    I bolted out the patio doors of the apartment and rushed around the side of the building hoping she hadn’t been awake enough to notice me standing there looking out and wondering if I’d ever have the courage to go for a walk while dressed! While here I was doing it whether I wanted to or not. I walked to the front door hoping to get back in that way not realizing or thinking about the fact that I didn’t have my keys and couldn’t get back in that way.
    I stood there for a minute and thought about what to do, knowing that the only way back in was the way I’d come out. That was halfway between the two buildings and on the way out I’d noticed several people on their balconies; which was why I’d rushed around the side of the building in the first place. I peeked between the buildings and they were still there and now there was a small group heading my way from another apartment. Scared I walked the other way and started around the block.
    Still relatively early there were quite a few people out and about that could see me from a distance. Too far away to see me clearly they merely glanced at me and looked away or watched me the way young men would any real girl walking along before them. None were pointing, laughing or calling me out. In fact some even seemed to be mildly interested in me as a girl. Not at all what I’d expected or thought would happen. Somehow I’d always thought there would be a big sign I couldn’t remove proclaiming I was a crossdresser hanging around my neck.
    Calmed down somewhat I managed to concentrate on making myself hold myself more femininely, to walk more femininely and to quit shaking so much. By the time I was rounding the third corner I felt so much more confident and assured only to have it all evaporate away when I nearly bumped into a man getting out of a car. He grabbed me by the shoulders to stop me and stared at my face for a second then let go and moved to the side. I blushed and on suddenly wobbly knees continued walking as he called out that I was cute and had great legs. I couldn.t help but smile back at him.
    When I finally made it back into the apartment it all felt both surreal and real at the same time. After that I started going out for a quick walk every night till my GF found herself another babysitter.

  80. jessica humphrey 1 year ago

    I have been out for a long time.I first went out dressed as a young girl at the young age of 5 .I guest I always knew I was meant to do this and have since then wore womens clothing,makeup and the whole nine yards. I love myself and know that there are some of us who are affraid yet to come out but in time and when you can love yourself ,you to will be able to come out.

    • Profile photo of Vanessa Law Author
      Vanessa Law 1 year ago

      Thanks for sharing your inspiration with us Jessica! I hope that we can all come to love ourselves – there is no step more powerful than this!

  81. Katielyn Novak 1 year ago

    My first experience was walking into a Cumberland Farms store, a convenience store in New Jersey. It was around 12am and the store was only down the street from where I lived, but I didn’t frequent the place. I knew there wouldn’t be many people out at this time, so I walked in wearing a short dress, a pretty pair of red open toe 3″ heels. The first thing the girl behind the counter said, “be careful the floors are wet.” she had just moped the floors. But she was so kind, she complimented me on my dress, “saying I love your dress it’s very pretty.” and complimented me on the way I walked in my heels. She had said most girls can’t walk in heels as good as I do, meaning me.

    I’m so happy to be a part of this group. Thank you for having a place were I can come to and be myself, and feel comfortable.

    • Profile photo of Vanessa Law Author
      Vanessa Law 1 year ago

      Welcome Katielyn! It’s great to have you as part of the community!
      What a wonderful first time out! A happy memory to treasure for sure.

      • Katielyn Novak 1 year ago

        Thank you so much Vanessa, I love being a part of this group, and I have many more stories if the other girls would like to hear them as well.

  82. Katielyn Novak 1 year ago

    Hi Vanessa, I loved your story. I would have died if I seen the police while I was dressed I could only imagine.
    The police are looking for cross dressers. great sense of humor I love it, and thank you from the bottom of my heart.

  83. Dianne (David) 1 year ago

    I’m still in the closet but I did venture out dressed I flowered blouse and short mean shorts for a drive and I walk on the beach. It went well but was where I won’t be know

  84. Charlotte Kerr-Scot 1 year ago

    Hi – Further to my last post I thought I would share a recent experience. I have been out a lot just of late – day shopping in supermarkets/clubbing/eating in restaurants.

    I try to read other peoples faces/reactions (particularly when I am wearing sunglasses); I think I am reasonably passable; UK size 14/16, and I try choose appropriate clothes – although I generally will wear pretty high heels (4 inch plus).

    I went into a pub that I often visit at night, for a glass of wine at about 2 o’clock in the afternoon. I said hello to a man who is often in this particular bar; he tends to be a bit derogatory about cross-dressers/Transvestites and Gays. That said he has never been nasty or hurtful just very outspoken. He was, on this occasion, with a young girl who had a baby with her and I assumed it was his daughter and grand daughter. I felt that the assumed daughter was looking at me in a way which I took to be a bit disdainful about a man being dressed as a woman but I just passed it off – I just kept talking to the girl behind the bar and her companion who was sat by me.

    A couple of nights later I was in the same bar and saw the man and asked ‘was that his daughter and grand daughter?’ – He said ‘yes it was’. I replied how nice to see them out together and how pretty the girl was! He replied how proud he was of them both and thanked me for the compliment about his daughter. He then said, “I suppose I shouldn’t tell you this but I had quite a time convincing her that you were not a real girl!’

    Obviously I was very pleased that a 23 year girl hadn’t twigged that I was a bloke but the other message was that my assumption about they way she was looking at me was wrong! She simply was trying to convince herself (and her dad) that I was a girl!! So do not read in to the looks you get anything at all – you may well be wrong.

    • Profile photo of Vanessa Law Author
      Vanessa Law 1 year ago

      What a lovely story Charlotte! Thank you for sharing, and… WOOHOO!! 🙂

  85. Vanna 1 year ago

    OMG! These could be my stories! I thought I was alone… Or at least not one of many!

    • Vanessa Law 1 year ago

      Vanna dear, you are part of a beautiful community – welcome!

  86. Vanna 1 year ago

    Also, I have to say… I love these clothing links! I’m 48, have been dressing for 30 years, and only been in public once.

    • Stephine 1 year ago

      I have been cross-dressing all my life. Part of my problem was my mom dressed me as a girl for the first 4 years of my life to hide me from my dad. I have felt safe and secure when I’m dress as a female. Always have. But going out in public has been my biggest fear. I mean, I have went out in public a few times as a female but only on halloween. That way (in my own mind) I know won’t think twice about it. It’s hard, at least, for me. I praise the brave ones who can.

      • susan jones 12 months ago

        I feel the same way, no courage, but I love dresszing up. I walk in public safe areas only.

    • Vanessa Law 1 year ago

      Hi hon, it’s a pleasure! And kudos on going out in public! Many don’t ever get the courage to do that. Keep living as who you are!

  87. Vanna 1 year ago

    I had a girlfriend that strongly encouraged me to wear her clothes. She bought me panties and bras, but liked me to wear her clothes. No shoes though because her feet were smaller.

    • Chrisrltina 1 year ago

      I had the same thing with my girlfriend she even paid for me to get breast implants that were her size so we could wear the same lingerie

    • Vanessa Law 1 year ago

      You’re a lucky girl – you both are 🙂

  88. Amanda Claire Jones 1 year ago

    As I say to people nowadays… You will find that nobody dies and the world does not stop turning! People have too much going on in their own lives to really notice others all the time

  89. Louise 1 year ago

    It is a great experience to go out dressed if you can blend in fairly well. I first did it many years ago when I did not have many clothes and certainly not any really good, fashionable clothes. I wore a dress that I had found abandoned somewhere and some shoes that were a bit too high for easy walking. I borrowed a coat from a relative without asking her. I looked in the mirror for a long time trying to decide whether I looked good enough to go out and then I decided to go for it. I walked to the bus stop and got a bus into the city centre for a shopping trip. When I stood up from my seat on the top deck of the bus I nearly dislodged my wig, forgetting that I was taller with heels. I had good experiences on that first outing and if anyone read me they were too polite to say anything about it. Buying things such as clothes and make-up in a couple of shops was the most daunting part.

    Since then I have been out dressed a number of times in various towns and cities and I once had a holiday in France when I was dressed for a week. (It was at the time of Mardi Gras!) I still find it a bit scary but when things go well my confidence builds and it is wonderful to be accepted as a woman.

  90. Julie Shaw 1 year ago

    My first time out was as a 16 year old. Very late one summer night, I gathered up the courage to step out the door and walk around the block. The “around the block” quickly became 6 or 7 blocks in my lovely suburban neighborhood, mostly because I didn’t want it to end. However, as I turned back onto my street, a police car pulled up beside me. The officer leaned out the window and asked, “Is everything alright, Miss?” I responded quickly, and rather quietly,that I was fine, just getting some air. He drove on, I rushed home, and took about an hour to come down from the high!

  91. Kandi 1 year ago

    My first time was this past February, I went to a town about 3 hours away and had a makeover at a CD store. I was so pleased with the results, but in hindsight, I was terribly dressed. I am in my 50s (closeted all my life) and was wearing a dress more appropriate for a 20 year old. But I did it! Since then I have filled my closet and lingerie drawer with many beautiful pieces, all age appropriate and I go out regularly. I even have a weekly volunteer office job that I do totally en femme! What a thrill every week to be called Kandi by everyone, no one giving me a second thought, just happy that I am there to help. The best part are the complements on my outfit for the week and the click of my heels as I walk down the hall. Best year of my life!

  92. Profile photo of Nora
    Nora 1 year ago

    My first time was when I was in college (about 2.7 billion years ago), and living in a studio apartment about 3/4 as big as my ex’s walk in closet. Although I have been dressing all my life, I had just bought my first bra that day (using a GF as an excuse) and was super-excited.

    I stuffed my bra with socks (this was _way_ before the internet, and as far as I knew there were no crossdressing shops in Albuquerque at the time) put on a pair of jeans that looked almost feminine, and a generic tshirt.

    I went to the park near my apartment, and went to sit under my meditation tree; I ran all the way there, and kept out of the streetlights, and when I got there, I sat down and started to relax. Then the couple making out on the _other_ side of the tree (it’s a big tree), said “Um… hi?” and I took off like a shot!

    I found another dark spot to catch my breath, and suddenly I was giggling! Couldn’t stop!

    I actually managed to walk back home, no one saw me….

    I have not really stepped out much since then (that is going to change, I am quitting men’s clothes cold turkey in about a month!), just kept it at home, but the thrill of going out, even for just a few minutes, I will always remember!

    • susan jones 12 months ago

      The thrill is fantastic only better thing is to find a man to chat with amiably and flirty.

  93. Profile photo of
    Ana Claudia 1 year ago

    first tima two years ago at NYC.
    I wear my black heels and a wrap animal blue pirnted dress, my wig and a sweater.
    It was a light drizzle so i get no umbrela.
    Was late in the noght so elevator was empty, i passed my first obstacle, but at the main entrance, i found a groop of spring breakers, so i move as fast as i could but one of them watch me and began to shout i don´t remembre what, i started to walk all the 34st to broadway, changing continusly for sidewalk to the other one exach time i sa people coming, or simply turning my face to look the store windows at macys.
    I took some selfis in some importanta places.
    While walking by Bradway to times i got a bigger trouble, a group of young men looked at me and someone said; hey he´s a dud and they began to follow me shouting and making noices. i tried to keep calm, change the side of the sidewalk and continu as if nothing happend, but some damage was made, so i have several people looking at me directly, but for my biggest surprise, they didn´t bother me or make things bigger.
    I could se they will not accept me but also i could detect they will not harm me at all.
    I was very nervous, i finished my photo session and try to leave behind those kids, so, i began to alk as fast as i could, but i step a crack in the floor and broke one of my heels.
    so i removed my shoes and get to the hotlel with no one on my feet.
    next proble, security check at the entrance, i was ready and expecting that, so i had my room key in my hand, and i remeberd the face of the security guy looking at me. i´ll never forget that incredulous face.
    I can say or write: while things happend i was really nervous but after that i think i was lucky, because i get mor auto confidence, and i understand that many people will not hurt me but i also understand that many people can do it, but most important i remember that with happiness.
    After this expeience i have a couple more adventures that in the future i will share you

    • susan jones 12 months ago

      Good story

  94. Ashley Lim 1 year ago

    Now I am nearly 68 years old. I have been a closet CD since I was 16 years old 1962. I only started to dress out in public in 2010 after I came across some CD friends in the Facebook. During the first few outings I was quite embarrassed but not really scare. But after 5 years I can blend into the crowd with proper dressing of course. We started the group gathering 5 years ago with two times a year (Marchs and Septembers). Our group grew from 15 people to over few hundreds now, but each gathering we can manage 40 people. That was fun meeting all those LGBT friends.

  95. Julie 1 year ago

    I loved reading your story. It excited me, but at the time made me a little sad. You see, I am 64 years old, a little wrinkled, grey hair, and a little turkey neck coming on. I don’t believe there is any way for me to look female, and I love so much to underwear, but can’t go out in a dress or skirt. I would be the ugliest girl ever. Wishing….

    • paula 8 months ago

      you stop right their. every one is different ,but as you say that about your self, your making life harder , relax , i dont know your circumstances , but what ever they are,you can still be a lovely lady. it starts with your head &heart, we all have those, so believe in your self, ill start you off, your lovely .xx

    • susan jones 12 months ago

      I am so afraid too,but lucky me in NYC there is the village so I go out at night and I mean from 1 to 5 a.m. and walk around and I get to meet a lot man,surprisingly most are younger!! Like in late 20 to mid 40,s and of course they all want a piece of me, but now I know what a woman has always been careful to do,and that I’d chose your man. But I feel so sexy and pretty I’m in my late 50’s but I dress sexy enough to attract man.

  96. Louise 12 months ago

    I have been out dressed late at night and on dates but I still fear it.I am 64 and have been dressing since I was 8 or 9.I am married with a very understanding wife.She is my soulmate but it takes a CD to understand another.
    I live in a small town and I would love to go out on weekends with other girls like me and even meet for weekends or, even better for a weeks holidays with girls like me.
    We should be able to meet girls anywhere at anytime.
    It is getting late in life for me but, the kids todays should benefit from our experiences.


  97. Janine 12 months ago

    I just got through reading about all of the first time out.
    I recently had my first time out and it’s true. Dress so that you can blend in walk like a lady dose. Try to keep from speaking as little as you can. Always look at whoever you are looking at in the eyes and most of all smile.
    I noticed that if you smile people just seem to look past you. Some smile back others don’t. Last night I went out dressed in a skirt and turtle neck long sleeve top with 3 inch heels. I went to a local Walmart and bought a new dress and a blouse. Afterwards I went to a sports bar and grill where I got a light snack after I had to use the ladies room which I did without any problem.
    Driving back to my motel I got caught in a traffic jam stop and go but by being patient I didn’t have any issues.
    Looking forward to going back out again today wearing my new dress

  98. Profile photo of Toni Ginamaria
    Toni Ginamaria 11 months ago

    My first outings back in 1990 were to gay bars hair dressers and shops out of town. I would go out Dressed As a Boy DRAB first and later in the day in DRAG. My spidey sense was off the charts, but as nothing bad happen and what did I could handle, I became more relaxed. I got drinks bought for me doors opened and cigarettes lit propositioned by some, other times I would attract admirers that would hang around and look down at their feet and talk awkwardly till I would take the lead and flirt and reassure them. I would smile look them in their eyes play with my hair and brush against their arm or touch them on the thigh. Eventually I would go shopping ask for advice and try on in the dressing room before purchasing. I wore 4″ heels around the house and packed flat slippers in my purse. I practiced my make-up skills, went for applications at the hair stylist and department stores. The advice I got was to prep my skin shave clean tone moisturize. As for make-up less is more. My girlfriend would tell me that department stores work on commission drug stores are more affordable and you can return anything that doesn’t work. Note I have never before returned anything, ever. Go easy on the eye make-up, less slutty/ clownish rather more natural, better appearance to blend in with natural women. Watch how other women dress in the places you are going. No leather outfits short skirts and high heels at the grocery store. Try to copy to blend in and not to stand out. Sweater if you don’t yet shave your chest & arms tank top cardigan or blazer if you do, jeans and mid-heel boots or flat unisex shoe. My mom advice: go easy on the perfume to always stand up straight look people in the eye, ask for things in the form of a question smile often and say thank you. And finally don’t worry about what other people think unless they pay your bills. Get dressed put on your make-up and a touch of perfume grab your purse and go out stay safe and have fun.

  99. sunita 11 months ago

    i am wearing every day saree and blouse indian dress and with light make-up but i dont store courage to out of home it may be i will be prepare to go outside as female thanks for yours initiation –sunita

  100. Profile photo of LadyCDJennifer
    LadyCDJennifer 11 months ago

    I’d be too scared of going out en femme. as I fear winding up like the late Gwen Araujo, a young trans-woman, who was raped and beaten to death at 17.

  101. Sissy Minister Pope 11 months ago

    The first time I went out cross dresser I was 21.

    I had a cute little dress on with huge breast that I cut off a sex blow up doll & stuffed in a bra that was way to small.
    They were so big they almost would not stay in the dress I was in.
    The dress was my moms and so was the black wig that was long.

    To this day I can not believe I fit in her stuff.
    Gosh even the shoes were way to small she being a size 6. 1/2.
    I’m a size 8 1/2 men and have found that a female size 8 1/2 fits well.
    Wow right.

    It was night time & I was doing my usual drive.

    There was at the time 2 stores because I was 21 & am now 38 & now there not there.

    I would go to 2 adult porn store & the rest area of a I-94.

    Then had to get gas & was like oh no I have to walk in to a gas station.
    Oh fear came across me so hard.

    What will this guy say?

    Will he laugh?

    Ah my heart beating so hard.

    But he was just like ahhh.

    Probley like gosh what big breast or something.

    I was ducking my head.

    Then got out of the store & to the car walk ing fast.

    Well that’s my first time.

  102. millie de colchon 11 months ago

    unsure of my age at the time,think i was 8 or 9,and i was being punished (and trained),at the time.Gran(curtsey),had decided that “horrid and elly little bois”,would not be allowed back in Her house……,so if She(curtsey),required me to be Her grand-daughter or “sissymaid”,then that’s what i had to be.took me until i was 27,before i realised that Her(curtsey) reasons were obvious……,thank you,for everything Gran(curtsey).love,hugs and sissygurl maid kisses,millie(c.d.maid) de c.

  103. Profile photo of Grace
    Grace 11 months ago

    I had met a freind on line at the DC Transgenedered Ladies Site, she liked the picture of my legs! She was renting a time share on the beach where I live and invited me over to talk, drink champagne and to bring a few different outfits so we could play adult dress up. She also suggested that I arrive in my male persona but I thought that if I were to be true to myself I would arrive as the woman I intended to be that night. So. I dressed, packed a few different outfits and wigs and sent off for the resort hotel. I parked and then the thought hit me, I needed to go to the front desk, then to the elevator and up to the room. Of course it being a Friday night the hotel was quite busy. My freind did meet me in the lobby but the event was both terrifying yet excilerarting. I was dressed in a black wig ( I am a natural blonde), black leather mini skirt with a black leather jacket over a black teddy and of course four inch heels. Quite the hooker look I suspect but being 6’2″ I wasn’t too worried about any response besides I was too excited to notice. We road an elavator loaded with people who again were very accepting.
    The evening was great, good talk, many different dress and wig changes and did I mention Champagne! My first time in public with another that was just like me. All in all one of the best nights of my life.

  104. Alexis W 11 months ago

    A Very Important thing that everyone must know, is that once you’ve been out a few times, it’s hard to put the genie back in the bottle.
    Press yourself to take that walk around the block…walk to the park…wherever.
    One good place…drive thrus…and place will do. Going through the drive thru will let you feel the exposure of being seem femme and interacting in a limited way at the same time.
    Move up to convenience stores…then department stores.
    Gay…or trans friendly bars are a given, and provide a safe environment…but they are too shielded.
    Go grocery shopping!!
    Getting yourself out into the real world is so very liberating and such a telling tale of how you appear to others.
    Dress appropriately for where you are going…walk like a lady..
    Smile…be polite.
    I will suggest that the third or fourth time will bring a feeling of calm where once was unrealistic fear.
    That is how I got myself out…
    and now shopping or errands are nothing special…just natural.
    Go out….go…go!

  105. Shelly 11 months ago

    The first time I went out dressed I went to a Halloween party dressed as a hooker . Most of the people at the party knew me but no body reconised me. I did my own makeup wig, false nails, False breast, woman’s cloths and looked great and won second prize $50. There is the short version of my first time out.

  106. Profile photo of Rosaliy Lynne
    Rosaliy Lynne 9 months ago

    Many good stories and much good advice. Nearly all mirror my own experiences going out in public for the first time as a woman. My first time was also the first time I used my girl name in public. The whole experience was FABulous. My smile lit up, my heart skipped beats.

    Makeup – I am a minimalist in that regard – use enough to look good but avoid looking like a clown or a slut. Unless you are going to a slut party that look won’t work well and might get you the very worst kind of attention.

    Smile – the best defense is a good offense and the best offense is to smile and look like you belong where you are. Remember most people see what they EXPECT to see and seldom look more closely. When they do, and some may frown or look disapproving, a smile disarms them and bolsters your confidence. Smile, maybe wave slightly and move on.

    • Profile photo of Maxine Doos
      Maxine Doos 9 months ago

      Wonderful advice, Rosaliy,
      The makeup “less is more” is so true.
      Act as if you belong and smile (because you’re enjoying it!).

  107. Robert Eres 9 months ago

    The first time I crossdressed in public was about 18 years ago. I was living alone in small apartment. I had a day off from work, so I had shaved my body. Next, I spent some time applying my makeup, picked out a nice dress. The dress length was about three inches above the knees, so not too short. I put on pantyhose and a wig and looked at myself in the mirror. I was beautiful and was very nervous. I had no car, I walked everywhere I went. I put on a pair of flats, packed a small purse and went out. I nervously looked around to see if people were staring. It turned out, no one really noticed me and that gave me a boost in my confidence. I walked all over for about two hours and I felt very comfortable.

    When I got home, there were two of my neighbors sitting outside, both of them male. They looked at me and whistled. I gave them a quick smile and disappeared into my apartment. I thought for sure they were going to come after me and beat me up. They never bothered me and I began to venture out more and more since then. Now, I just go around dressed up and feeling free. However, I work a full time job and I dress in my man clothes. Sometimes, I will have on underneath a nice pair of panties and pantyhose. I just love bringing out my girly side.


  108. suesy 9 months ago

    im scared of going out dress as a female in public i tried it at the last place i lived now i moved out west have a girlfreind and her and her family think im gay for dressing as a female

  109. Bobby 9 months ago

    I started dressing around 9 or 10 after mom had me help with the laundry and I found out how nice and silky panties felt. Stayed closeted till about 30 when I had cover a night shift at work for a while. I was the last to leave around 10pm each night and I thought it would be a great chance to practice walking in my heels. Started with just the shoes but soon changed completely after work and would walk around in the building all dressed up. But when spring hit it was nice to step outside and soon I was walking around outside more and more. Getting braver as time went on I started to walk the sidewalk the industrial park was on. It was scary but exciting when cars would drive by till one night it was a police car that drove by and then pulled over and stopped. I was terrified but kept walking because my car was in the lot just beyond the cruiser. I walked on past and got in my car and drove away with my heart pounding in my chest. But I was back out the next night for my nightly stroll feeling braver but still nervous. Still need to go somewhere dressed but I’ll get there eventually.

  110. Jamie 8 months ago

    I have been going out more feminine and shopping for women’s clothing when I can I wear panties all the time and wear women’s jeans and blouses with my boots.I shop for womens clothing at stores and no one cares about me.I am happy to be able to be the woman I want to be.It gets better and easeyer each time .Don’t hold out to long and enjoy the wonderful times.

  111. Roberta 8 months ago

    God I was nervous, didn’t get in a cab I caught the bus as I lived in London and only I could do it, I caught the wrong bus as I did not want to be recognized locally. I had a woman that proclaimed I was a man but this is London no one takes an issue about it. I walked from Piccadilly to Charing Cross Road in full heels in total safety. I went to a retro 80’s club and had the time of my life, photo shoots galore. Ended up leaving the club at 4 am and going back. And this was the most embarrassing moment. I was at the time living in a place where the kitchen is shared and was having a glass of water and Stuart (the local romeo) decided to caress my butt until I turned around, god he got a shock. That was last year. This year it is my 50th and I have been blessed with a taut body and no wrinkles. All my friends know about it and I am doing the circle line cross dressed.

  112. cassandra 6 months ago

    hi ,I have not gone out in public yet but on the other hand I had just got my new dress that my wife brought me and as I was going to work I stopped and put on my 5 inch heels stockings nickers corsette bra forms and drove to work 50 kms country passed a few cars that was scary at first through town which is small and to work which I manage drove down to the back and changed back in to my work cloths.i have done this a few times and it was a great feeling I cant wait to get out there .congratulations to all you girls who have been there .when I do I will tell the story.

  113. Brenda 5 months ago

    Actually I’ve been at this for many years.
    I do think we greatly overrate our pass ability.

    Kids and other women, spot us easily.
    In most cases , it simply doesn’t matter,
    as more and more, there are laws in place to protect us and give us rights.
    Though in fact,
    should you enter the legal systems, jails and prison can be very negative environments.

    I recall, being very nicely dressed in a white outfit, with my long dark hair red heels.
    I suppose that alone on a sunny afternoon made me stand out.
    I walked past guys in suits making their way from a luncheon, to their vehicles in the parking lot. across the square, a guy seem to be intent on staring,
    before, entering the local pub.
    yes, everything was going just fine.

    I walked confidently into the theatre,
    the attractive ticket attendant smiles and asks.
    “Can I help you”

    “one adult for Hedwig and the angry inch” says I.

    She quickly turns to the other …much older female attendant…
    “Sorry, it’s all sold out” and I think she actually put up her closed sign.

    Well that’s fine, I’m use to disappointments.
    It was a polite way of saying,
    we don’t want your kind in the theatre.

    No harm done, I enjoyed my day, just walking to and from the theatre.

    It was a few hours later, I discovered, that, in fact,
    the movie wasn’t even showing that day.

    This had been a panic over reaction, by an untrained staff.

    I’m quite sure, as the years have past and the community has progressed,
    they wouldn’t be allowed, to so readily, turn away, a paying patron.


    In sort, there are still reasons to be careful and fearful.
    There are still many unsafe places to be out and about alone.
    But then that is the lot of all females as well.
    They live with fear, for their safety, all their lives.

  114. Acsde 5 months ago

    Hi I still wearing a collar dresses with back button and fitted bra .but I don’t afraid to go outside home. I wearing crossderssing only at home when I was alone.

  115. Profile photo of Terrim
    Terrim 5 months ago

    My first time out dressed was with my wife to a costume party. My sister did my makeup and wig. Everyone at the party thought I looked great. We went to a bar after and some guy who was drunk tried to kiss me. I hadn’t told my wife yet that I was a crossdresser. I tried to kiss her in the elevator and she was turned of. Years later I told her.
    I love going getting my hair done and going shopping. The key is dress approaitely in public if you want to blend in. I have been going out over 30 yrs.

  116. Profile photo of Stephanie Archambault
    Stephanie Archambault 5 months ago

    Yesterday, I dressed up, put a light touch of makeup and drove around the area. I had done that before. The streets were deserted (this is a sea resort, and on a weekday in the evening, things are pretty tame). I drove to a beach access, parked the car, got out. OUT. There was no one. I walked across the sand dune to the sea. It was beautiful, the light was crystal clear, race horses were there with their trainers and galloped up an down the beach. I looked at this from a distance, feeling pretty, peaceful, fulfilled. I got a little more confident, and decided to drive around the busier streets of the resort. People were going to the restaurants and bars, or merely enjoyed their evening walk. The sun was still up, and nobody even gave a second look, although I was at times a few feet away from them. Was I proud!
    But I was in my car.
    I decided to park on a street close to the beachfront, and to take a walk on the promenade. Obviously, I would come across other people, and my heart began racing a little. But hey, I was feeling really into it, and was confident.
    On the promenade, a couple was walking with their kids. The man did not pay attention. The woman looked at me briefly. She called to her husband, who was a few feet ahead of her, and asked “Have you seen the…” My confidence just crumbled. I turned back, as if remembering something, and never heard what she said. Was it about me? Was it some other thing?

    I drove home, still on a high from the earlier part of the outing, but the woman’s words, or at least the meaning I gave them, got to me, and I was pretty deflated when I arrived.
    It was urgent to check if my sentiment of feeling passable, let alone pretty, was in fact founded. Forget about dinner: I took pictures, turned my head just so, then smiled this way and that. Contrary to earlier experiences, I could not find one picture of a reasonably good looking lady: all I saw was a guy wearing makeup, with a clumsy smile. And an older guy at that, with a sagging jawline, pockets under the eyes and an exceedingly red lipstick. Yet, when I looked at myself in the mirror, it thought I didn’t look so terrible. Perhaps a little too prepped up for a stroll on the beachfront, but not overly so.
    Either the lights were really lousy and the pictures unduly terrible, or my brain reprocesses my reflection into what I want to see. A bit of both, I guess. And I am an older guy wearing makeup too… There’s no escaping that.
    So here I am, wanting to go out again, but only if I am dead certain I am passable. And how could I ever know that for sure? How can I even think I can pull this off?
    I don’t just want to crossdress in my closet. I want to live as a woman. A W O M A N ! Not a guy in drag.
    Talk about dysphoria.

  117. Susan 5 months ago

    My first outing was last Halloween. I don’t think it counts though. I went to a Casino that was very busy. I wore my black knee high boots with a short black dress and a blue sweater. I applied lots of makeup like I always do (I tend to go for the slutty look) and I wore a nice wig.

    Almost every man that saw me smiled back and I wondered if they figured me out. I just kept smiling at every one and staying off to the sides. One lady passed by and said “nice costume”. Guess she knew, but shortly after that a nice man approached me and offered me a drink. We talked and exchanged contact info. I told him I was trans and he said he liked that!

    We hung out for a little while, but then he had to leave so I gave him a very nervous kiss on the cheek and asked him to keep in touch. He didn’t. Oh well. Most of the women were returning mean looks when I smiled at them, but almost every guy adored me!

    Then I was propositioned. Some very well dressed guy offered me $200 to spend an hour in his room. He was very nice and I was tempted (since I am Bi-Curious) but I declined by saying I had to go home. I had to use the rest room. That was scary.

    I decided to try my luck in the ladies room. There was a line, of course. While waiting a very nice lady spoke with me. She could tell and asked if I was transitioning. I replied that I hadn’t taken hormones yet and then she advised me against them. She told me that I was pretty without the pills. She was nice.

    Once inside the rest room I noticed a few mean glares, but no one hassled me. By this point I was exhausted so I headed for my car. I felt victorious as I proudly walked through the parking lot!! Oh what a night!!!

  118. Sam Scott 4 weeks ago

    My very first time out dressed was one winters evening when I was about 16. My parents were out with my sister, who played in an orchestra. I didn’t have much clothing of my own but I was about the same size as my mum.

    I always wore my own bra, knickers and tights but otherwise all of her clothing. She had some beautiful clothes and I always took a while selecting my outfit. a touch of lippy and perfume then…….Panty corset first with a full slip over the top. A silky blouse with a bow collar (it was the seventies) a gorgeous A line skirt that she wore for work , which just reached my knees. To top it all off as I didn’t have a wig at that time, just longish hair, I picked a nice sheepskin coat, hat ,gloves and scarf.well disguised. For footwear I borrowed her knee high brown leather boots which had medium heels, about 2 inches and finished the outfit with a nice shoulder bag. I must be honest, I fancied me lol.

    The dog we had didn’t know what had hit him. we walked the streets for well over an hour. I loved it, I could barely contain myself. The feel of my skirt against my legs and the feeling of nylon encased legs in the winter cold. putting my door keys and a few tissues into my shoulder bag and zipping it up. I was absolutely devastated when I got home , with about 1/2 hour to spare and changed back to boy drab. Carefully re arranging evertything where it had come from.

    Did you take the dog out my dad asked when they all got in. ……..oh yes !

    I love dressing and its a habit that’s stuck for nearly 40 years but this outing is still vivid in my memory. It was the change from wearing tights and a bra in my bedroom to becoming Sam.

  119. DANIELLE 2 weeks ago


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