Nervous about going out crossdressed for the first time

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.

Crossdresser Heaven - Find Your Tribe

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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  1. MINI 3 days ago

    Wow great….i am closet CD and wanna go out. But I am looking for admirer who can take me out and treat me like woman. Unfortunately I have not come across any site where CDs and admirers can exchange mails/photos/likes/dislikes etc and then meet in real. All sites I have seen are paid. Its frustrating

  2. Daviva 2 weeks ago

    I love to dress up I went to my friends party dressed for the first time things was going really well I got talking to this lovely man we got on really well chatting way then he started to rub his hand up and down my leg I was gettingreally excited but when he got a bit higher up my leg I just froze I did not know what to do I was frightened as I have never been with a man how can I get over this he stopped said sorry and walked away I felt like a idiot I was so nervous how can I manage my nerves and go all the way Davina

  3. Zarina Starinova 2 months ago

    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

  4. jennifer 2 months ago

    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 dresses i kow its been a while since i posted things but i was trying to build up my courage and now think my next thing is to go to a store thank you all will wright more later

  5. Bon bon 4 months ago

    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. .

    • Bon bon 4 months ago

      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

  6. Bon bon 4 months ago

    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..

  7. Marianne Tornander 4 months ago

    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. If the skirt was long enough, I would roll up the legs of my trousers to the knees and let down the skirt in a secluded corner of a park or such. Otherwise I would finish the change in my car. After a short walk in the empty streets I would redress and return to the hotel.

    The differences that first real time were mainly the following:

    1. I wore full makeup and a wig
    2. I didn’t hide my clothes when leaving and had no means to hide them when returning.
    3. I mixed and interacted with other people in a local store.

    Off course I was nervous but at the same time determined not to bail out. And everything went totally fine.

  8. Portia 5 months ago

    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.

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