Crossdresser Heaven

Going Out Crossdressed For The First Time

Were you nervous the first time you crossdressed?

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! She blogs about the transgender journey at Please comment below and tell me what you think!

133 Enlightened Replies

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  1. Amanda Trane says:

    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.

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