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.
More Articles by Vanessa Law
- 7 Essential Tips to Crossdressing
- Win a Free Makeup Prize Bundle from Jecca Blac
- A Few Changes in Our Family
- I Want to Live Like That
- Hope in Despair, Light through the Darkness
-480x270.jpg)
God I was nervous, didn’t get in a cab I caught the bus as I lived in London and only I could do it, I caught the wrong bus as I did not want to be recognized locally. I had a woman that proclaimed I was a man but this is London no one takes an issue about it. I walked from Piccadilly to Charing Cross Road in full heels in total safety. I went to a retro 80’s club and had the time of my life, photo shoots galore. Ended up leaving the club at 4 am and going… Read more »
hi ,I have not gone out in public yet but on the other hand I had just got my new dress that my wife brought me and as I was going to work I stopped and put on my 5 inch heels stockings nickers corsette bra forms and drove to work 50 kms country passed a few cars that was scary at first through town which is small and to work which I manage drove down to the back and changed back in to my work cloths.i have done this a few times and it was a great feeling I… Read more »
Actually I’ve been at this for many years. I do think we greatly overrate our pass ability. Kids and other women, spot us easily. In most cases , it simply doesn’t matter, as more and more, there are laws in place to protect us and give us rights. Though in fact, should you enter the legal systems, jails and prison can be very negative environments. I recall, being very nicely dressed in a white outfit, with my long dark hair red heels. I suppose that alone on a sunny afternoon made me stand out. I walked past guys in suits… Read more »
Hi I still wearing a collar dresses with back button and fitted bra .but I don’t afraid to go outside home. I wearing crossderssing only at home when I was alone.
Thanks
My first time out dressed was with my wife to a costume party. My sister did my makeup and wig. Everyone at the party thought I looked great. We went to a bar after and some guy who was drunk tried to kiss me. I hadn’t told my wife yet that I was a crossdresser. I tried to kiss her in the elevator and she was turned of. Years later I told her. I love going getting my hair done and going shopping. The key is dress approaitely in public if you want to blend in. I have been going… Read more »
Yesterday, I dressed up, put a light touch of makeup and drove around the area. I had done that before. The streets were deserted (this is a sea resort, and on a weekday in the evening, things are pretty tame). I drove to a beach access, parked the car, got out. OUT. There was no one. I walked across the sand dune to the sea. It was beautiful, the light was crystal clear, race horses were there with their trainers and galloped up an down the beach. I looked at this from a distance, feeling pretty, peaceful, fulfilled. I got… Read more »
My first outing was last Halloween. I don’t think it counts though. I went to a Casino that was very busy. I wore my black knee high boots with a short black dress and a blue sweater. I applied lots of makeup like I always do (I tend to go for the slutty look) and I wore a nice wig. Almost every man that saw me smiled back and I wondered if they figured me out. I just kept smiling at every one and staying off to the sides. One lady passed by and said “nice costume". Guess she knew,… Read more »
My very first time out dressed was one winters evening when I was about 16. My parents were out with my sister, who played in an orchestra. I didn’t have much clothing of my own but I was about the same size as my mum. I always wore my own bra, knickers and tights but otherwise all of her clothing. She had some beautiful clothes and I always took a while selecting my outfit. a touch of lippy and perfume then…….Panty corset first with a full slip over the top. A silky blouse with a bow collar (it was the… Read more »
SHOPPING MALL, BLACK PADDED BRA,PANTIES,BLACK PANTYHOSE,BLACK DANCE LEOTARD,TIGHT FIT BLUE JEAN SUSPENDER OVERALLS WITH BACK ZIPPER,MEDIUM HEEL LEATHER SANDAL SLIDES,LONG HAIR,MAKEUP,LIPSTICK,NECKLACE ,BRACELET, RINGS,PURSE,SHOPPING FOR LINGERIE,BRAS AND GARTERS, CROTCHLESS PANTIES,AND THEN OUT FOR FAST FOOD,DRIVE AND BACK HOME SAFE.THANKS.
Only wish I could find someone to help bring this girl in me out more as of now I only dress at home live in two family house upstairs appt.downstairs living room and there bedroom right buy my entrance so I have really no privacy only when they both go out I live on long island new York need to make new girlfriends like me and find new apartment thank you so so much love to all Tiamarie