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. Jessica 2 weeks ago

    That’s an awesome story Vanessa. I’ve been going back and forth on this. I don’t feel I’m able to go forward with surgery to make my dream life come true since i have a wife and 2 kids now but would really like to try cross dressing.
    Earlier this year i was got up the nerve to tell my wife. She was less than pleased and i felt i had no support. After telling her the truth i wanted to take it all back but knew i couldn’t.
    I hope to one day get up the money needed to get what i need to introduce the world to the real me.
    It’ll just be hard considering i have to sneak around to do it.
    Thanks again for the story

  2. Mitch aka Holly 2 months ago

    My first time out crossdressed in public I went to a halloween party and had a blast,I then won 25 dollars at that party.The next time I went out crossdressed I went to a dress shop in daylight and that was exciting………..

  3. Gary aka Ginger 2 months ago

    So envious of those brave enough to venture out into public. One of the reasons I hesitate is my naturally male look. I’d never come anywhere near passing and I’m afraid of being discovered.

    Despite my fear, I realize I’ll never find true girlie bliss until I strut my stuff.

    I need a support person (a wing girl). I’m hoping my gf will step up and be that person. She knows and accepts that part of me but has yet to find time for girl bonding.

    I’d love to take her to New Orleans on an all girl get away. I acceptance level there seems more forgiving.

  4. Davina Johnson 2 months ago

    I have been crossdressing for over 46 years, from the age of 12 years old. It wasn’t until the 1990’s that I took the plunge to go out dressed as a woman for the first time. I had contacted a very kind lady who owned a bridal wear shop to pay her a visit to try on a new evening dress. I had decided to dress for the occasion as my wife would be out at work all day and I had taken the day off. I was anxious and extremely excited at the same time. It was a feeling I would never forget. I made sure I looked as feminine as possible having had a lovely soak in the bath, shaved my legs, underarms, chest and of course my face before drying myself down then applying my makeup. By the time I had finished getting dressed I looked presentable and dare I say passable as a woman. I had had years of practice walking about the house in 4 in heels so felt fairly confident.
    I wore a simple black pencil skirt with a long sleeved cream satin blouse which had a cowl neck. With my choice in a pair of black 4 in pumps the look has not going to make me stand out. I grabbed my coat and purse and off I went to drive the twenty or so miles to the shop.

    Walking the two hundred metres from the car park to the shop was the most nerve racking but envigorating experiences I have ever had. Just the sound of my heels on the sidewalk, the restriction of my stride cause by the pencil skirt and the cool breeze wafting around my stockinged legs were energizing. Although I received some obvious looks nobody paid me any undue attention; people just went about their business.

    On entering the shop Wendy, the shop owner, greeted me and complimented me on my look and on on how courageous I was as she hadn’t expected me arriving en femme. We spent the next hour her selecting and me trying dresses on which eventually resulted in me buying a beautiful emerald green satin long sheath dress.

    All in all a day to remember for the rest of my life. As a result this was the experience that gave me the confidence to go out dressed many, many more times thereafter. I had to find a word to describe this experience and feeling it would be “exhilarating”.

  5. Donna March 2 months ago

    My first time was about 40 years ago when i was working as a young musician. My girlfriend asked me to help out her cousins band who needed a guitar player for one night when the regular player was sick. I said yes at first but when i was told i would have to wear a dress and heels i tried to back out with no luck. The show went on and me dressed in a satin dress and 4 inch like all the other girls i felt great. It was a wedding and i was shocked when one of the groomsman asked for my phone number after the affair. I politely gave him the number hoping never to be called. The experience overall is one i will always treasure.

  6. Kim Morgan 2 months ago

    When first come out a lot of preasure is off you are being honest to yourself.

  7. Tina 3 months ago

    I remember the first time. I went to crisscrossing store in the Detroit area for a total transformation and photo shoot. When we were finished, I took off in my car. It was around 2PM. I got hungry and stopped into a fast food restaurant. When I went in I got some looks from the people in there. Nothing nasty mind you,but I could tell some people were looking at me. The more they looked the more I didn’t care. I ate my lunch and walked out happy.

  8. Kim 3 months ago

    The first time I went out { after playing with girl’s clothes for years } was in the military. we were having a Mash party and I went as Klinger. Two weeks before I went to a store got a special dress made, a bra with breast forms and make up kit. It was a little difficult buying my high heels in the BX. The night of the party I got all dressed up and walked to ward the party. Walking in heels was so different. When I tried to cross the street I didn’t allow enough time and had to dash like a scarred little bunny. The party was just perfect! The guys hugged me and danced. The Col. even patted my butt. I spend most of my time out now but nothing can replace that first special Time. Keep having fun dear. Kim

  9. Shauna 3 months ago

    My first outing was in the 90s with jasmine(a cross dressing friend) and Gina(my 2cd wife) I was scared as all get out. It was Halloween and we figured what better time to go out in public, little did I know where we’d wind-up. I had a pink miniskirt, knee-high boots a wig and my make-up was perfect(my wife did it for me). I had a scarf to cover my Adams apple, and Shauna was ready to roll babies, we went to a novelty store, then dinner and dancing at 501. I was blown away,y fears were settled when I got more compliments and hit on more than them…. I felt,dressed,and looked beautiful…. It’s a feeling I never want to forget but also one I haven’t felt in a long time now that I have to do my own make-up and age has me as well. Thank you for letting me take a walk down memory lane and reminding me that I can do this again just put fear behind me and be confident that I can do it again.


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