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
I have been to Fantasia Fair 2014 where you can walk around all week as a lady and everybody is CD friendly even the Police. I have also been to a cross dressers night club in Va from 2000-2007 until it went out of business. I have not been out since 2014 but I think I will get back into my feminine side again. I miss being Portia and being out and about.
The first time I openly went outside totally en femme is summarised in my profile and will soon be published in more detail in the story about my whole journey until today. But I hadidn’t been out in female clothing several times before that. Typically I would dress in a dress or blouse and skirt at a hotel room on a work trip and cover the clothes with trousers and a coat, either putting the skirt inside the trousers or bunched up around my waist. I would then venture outside late in the evening with my heels in a bag.… Read more »
I’m happy for you g.f. my first time was I went to a corner store to get a few things I was dressed felling my self I be darned my car had trouble walk down the street wearing with outfit got honks, whilst, mind you I was wearing ,a Mico mini red 10in leather skirt,6 in heels of course matching. . . After I got that I know I felt myself..
Hay g.f. love to go out feeling my self . . .I wear skimpy outfits. . .6 inch heels 10 inch micoy mini,, tight fitting.. with a long wig . . The look’s from the guys . . . Makes me switch better. .
Just got back. . . Omg went to a new store too get a few things… Dress skimpy , short, tight, the eyes I felt made me wet … I’m going back….Got Feld up ….. I know now the
feeling and looks we Get..mmm
i have been going to fast food drive throughs and noticed that i dont get a 2nd look it feels real nice even had a young gentlemen give me my food and said here you go mam have a wonderful day and that made me feel so wonderful and me and my wife went to janits closet in detroit we drve 2 and 1/2 hrs to get there nd i had my first facial and even got to try on some dresses .what a wonderful experience ,even the girls in there said that she would like to try on these… Read more »
I love this ,my persona,Zarina Starinova,loves going out fully dressed,wearing outrageous outfits,hoping for reaction for those that see me.I’ve been out in zentai, wedding garb,formal gothic apparel ,and other eccentric apparel
I constantly under dress i put make -up and no one notices i luv you for having strength to go as you feel
The first time I went out dressed was just 6 weeks ago, Halloween 2017. I had already had a wonderful makeover session and knew that I could look fairly passable, but only with professional help. A few weeks later I was in Philly for work, the week of Halloween. I asked my makeup artist for a contact in the area and she gladly put me in touch with a wonderful woman who invited to the Henri David Ball, a very big costume ball among the gay/TG community in Philly. I figured that would be safe since who doesn’t get all… Read more »
My dear Vanesser, your letter touched me deeply, and bourght back so many memorries, so many of us girls worrie about what myte be, even if you are experienced and you get clocked just keep going, and act like nothing happened. The first time I went out fem I went to a small clothing store in Dandenong, and was escorted out the door by security gaurds stating that my pressence was not appreciated, that was many years ago now, my point is never give up, be true to yourself and enjoy your life the way you want.
Regards Sharlett.
I am a maternity crossdresser,I go out to eat other pregnant mom’s,they know about me.We go maternity shopping,I love it.