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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Dedicated to creating a safe, supportive and welcoming environment for everyone in the transgender community.
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  1. Susan 4 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!!!

  2. Profile photo of Stephanie Archambault
    Stephanie Archambault 4 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.

  3. Profile photo of Terrim
    Terrim 4 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.

  4. Acsde 4 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.

  5. Brenda 4 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.

  6. cassandra 5 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.

  7. Roberta 7 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.

  8. Jamie 7 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.

  9. Bobby 8 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.

  10. suesy 8 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

  11. Robert Eres 8 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.


  12. Profile photo of Rosaliy Lynne
    Rosaliy Lynne 8 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 8 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!).

  13. Shelly 10 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.

  14. Alexis W 10 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!

  15. Profile photo of Grace
    Grace 10 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.

  16. millie de colchon 10 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.

  17. Sissy Minister Pope 10 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.

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