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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I have been cross dressing for nearly thirty some years and in the closet all of that time. My wife left to go see our daughter on the west coast of course as soon as she left I needed to get dressed and did so. Stayed dress all day in the house tho and it was really fun just to be dressed in those cloths. I had only about a month before gotten my first set of breast forms and I think that is what made it so special for me on that day. At any rate it was early… Read more »
beautiful story <3
to Diane,
Just be you and go out dressed and do the things you would be doing if not looking female…i do..i only have female clothes.
Just Do It ! ! ! you only have one life to live,so live it the way YOU want to,
Diane, I, and I am sure many other closet cases out here just loved and experienced empathy with your outing story. In my case I have visited a professional photographer who indeed was good to me, and I have done similar under the radar outings all dressed up. How exiting those outings were! But normally I am restricted to less than one hour ventures when I get that time alone. This means I am able to don the finery and strut around for a while and then it all comes off and goes back into storage. Today I worked on… Read more »
Like many others, I’ll never forget my first time dressed out in the real world. I had been dressing for so many years and never having the oppertunity to go out en femme. Then one day after a snowstorm, the snow was shoveled from the sidewalks, but there was still icy patches in spots, and needing money from the bank, I decided to go out and just do it! Dressed that is, so I donned a pink running suit, some subtle make-up, page boy wig, white sneakers with pink accents, and a white goose down vest jacket, I headed off… Read more »
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 ! ! !
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!
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… Read more »
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… Read more »
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… Read more »
You go girl! Yah Monique!!
I’m so proud that you were able to gather your courage and follow through – little steps one at a time is all it takes. Hugs.
My first time out in fem clothes I drove by myself in my truck. My destination was about 500 mile away. I was certainly not dressed conservatively, actually I was dressed pretty sluttty. I had on a see through blouse which revealed my black bra (with breast enhancers) and a miniskirt hiked up to reveal the top s of my stockings and garters.I can hardly describe the rush. But I know those of you who have dressed and gone out in public understand. I drew the attention of many semi truck drivers and occasionally one would honk. 🙂 I did… Read more »