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
- A Few Changes in Our Family
- I Want to Live Like That
- Hope in Despair, Light through the Darkness
- Scholar Program – Transwomen’s Social Support for Medication Adherence
Vanessa Law
Latest posts by Vanessa Law (see all)
- 7 Essential Tips to Crossdressing - January 4, 2024
- A Few Changes in Our Family - April 15, 2021
- I Want to Live Like That - August 29, 2020
- Hope in Despair, Light through the Darkness - March 22, 2020
- Scholar Program – Transwomen’s Social Support for Medication Adherence - April 6, 2019
I would need a lot of help and support. But I would be willing to go out. X
Joanne, I feel the same way. I would need a lot encouragement, help, and support, to go out.
Sandie.
I always tell people that the hardest thing to do is take that first step out the door. I remember my first time walking out the door. I was nervous and then the further I walked to more confident I felt.
I joined a local CD club and went to my first 2 meetings in drab but could stand it no longer so my third one I went all dolled up, er, sans makeup. I just had to drive there by myself. I have never looked back since. It did take courage as I was scared, fearful, full of trepidation, etc, for what might happen. Nothing happened. They just welcomed me as a sister. I had fun right from the start. Since that fateful night I have gone out in public with the other girls and also in solo. Both have… Read more »
@fatima I’m so proud of you Fatima. I hope one day I’ll have the courage to go out. My biggest fear is I’m 6 foot one and with heels I’m 6’3 or 4. Jennifer
@Jennifer Rogers Yes in the words of Helen Boyd the authoress, CD girls are often giant women. I’m 6ft and I wear cowgirls or pumps with say 1.5 to 2 inch heels, so 6ft2 when I’m out on the town. Also my shoulders are broad. I shoulda played football (played hockey instead). Upon closer inspection others will think I’m a guy in women’s frock. I guess that is ok I can still look nice doing it. But I’m not passing for Shania Twain anytime soon. Way too tall for her!!!
In the end it is all about self confidence and just having fun. When we are out and about we do get noticed but in a nice way I think.
@Jennifer Rogers Always remember you can wear flats or kitten heels, they still look and feel good and attract less attention.
@chanel
Thank you for the advice. I did find a pair of flats that my wife no linger wears. They’re summer shows so I’ll have to order me a new pair . Jennifer
I received an order from Amazon yesterday. I had ordered a new wig and some mascara. My surprise when someone at Amazon threw in a pair of fake eye lashes as well. Jennifer
⁹
I’m replying to my own post. It posted without me writing anything yet? Lol. Oh well, here goes something…I am in agreement with Joanne, I would be willing to go out all dressed 👗 up, but it would take a lot of support and encouragement from the other cd ladies who have already done it. I would need some convincing to do it. My main worry is the other neighbors in the building seeing me and passing judgment on me ? Well, this is what I think.
Sandie.