Going Out Crossdressed For The First Time


Were you nervous the first time you crossdressed?

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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About the Author

Vanessa Law is a women enjoying the freedom to be who she is every moment of her life!

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  1. Monique says:

    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!

  2. Gabriela Almeida says:

    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

  3. charlotte says:

    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!

  4. stephanie says:

    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!

  5. Blake says:

    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 ! ! !

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