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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The first time was so exciting! I was in my yellow shorts and my pantyhose and high heels. I made sure that my hair was perfect and the makeup was just so gorgeous. I had a little bit of trouble driving in my high heels though. The experience of being able to be myself and wearing my pretty sexy attire was just too much. But I don’t care about what some people think about what I was wearing.
I ventured out about 8 years ago for the first and only time. So far. My body shape and looks don’t allow me to pass as female. So I venture out on Halloween. As I was hiding my clothes from my wife, I didn’t have that much to work with. I had fallen in love with this LBD, which was skin tight on me, and very short. I went all out. Wig, make up, breast forms, sexy lingerie and stockings and garter belt. I ended up looking like a hooker. I drove around for an hour before I got the… Read more »
I’ve been crossdressing all my life and love it. Now I’m trying to transition to a woman. But the first time I went out in public was very nerve wracking. Now I’m two years out in public dressed and its got a lot easier for me. So if its what you need to feel whole please do it for yourself.
My first time out in public was bit nerve wracking itself I to was born wondering if someone would notice but they didn’t know because my feminine clothes we’re hidden underneath my male clothes even though part’s still seeking out from my male clothes no body said anything to me bout it) my second time is kinda differnt got somewhat more daring] zena
Iv been out for 10 years I don’t have any male clothing I remember the first time tho .It was terrifying but I don’t give it any thought nowadays
The first time I went out dress up I walk around the on a summer day in the mall in,Phoenix it was a big thrill I think only a few girls look funny at me then I went home and felt great about my first time out.
I am 63 and i have not come out, but your story and others helps me to accept myself. it has been a difficult journey, and still is. But I hope to find the support I need on this site.
My first time I went out dress up I walk around the block it was not easy Iam a little tall could not find the right shoes but I walk the whole block.now I drive my car fully dress up and it fell great.
The first time I went out, I was wearing a short black dress, matching heels and a black satin bolero jacket. I felt great about how I looked but I had to park my car two blocks from the CD friendly club I was going to. I must have sat in the car for 30 minutes working up the courage to get out and each time I started to someone would walk by and make me pause. Finally I took a deep breath and got out and started walking. I will never forget the feeling of the wind blowing my… Read more »
The first time I went out was such a long time ago that I don’t remember many details. Like everyone, I was very nervous and worried that my outfit was not appropriate. (Do not remember what I wore but it probably included a very short skirt.)
Over the years, I have realized an important rule: Act like you belong and don’t really care what anybody thinks. Suddenly, you fit in perfectly. It is a great feeling.