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.

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’m passionate about creating a safe space for everyone in the transgender community to find laughter and friendship on their journey. I completed my physical transition in 2011 and through it I lost everything, and gained everything. I am blessed that I was forced to gaze inward and embark on the journey to discover and live my authentic self. My deepest wish is that all who wander here may find peace, happiness and freedom.
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Daniella Bryn Denali

Dearest Vanessa,
What a magnificent site you’ve created…it is an honor and a privilege to belong here with all of you wonderful girls! My first outing en femme, was with an SO many years ago, and was liberating to say the least. She opened Pandora’s box, and I love dressing like a girl!
It takes balls to play golf; and, it takes courage to be a guy that loves to dress like a girl. Get out there Girls…you’ll be glad you did!

Tammy William
Tammy William
1 year ago

Hi Vanessa, thank you for this topic. I decided earlier this week I would go for a midnight walk through the neighbourhood. I have yet to get a wig and makeup so I made due with every thing else and put a work jacket on just in case. I really enjoyed that walk up until I had to pass through security to get back into my condo. I hope he didn’t notice my brand new breast forms I proudly bought earlier in the day. Saturday morning I decided that I would like to drive to the cottage in my new… Read more »

Jin Crocker
Active Member
1 year ago

Hi Vanessa, Isn’t it funny what our brain can invent to scare us?
I have been wearing girl clothes my entire life, but just knowing that I am different makes me aware of who is around me.
For me it is not crossdressing as much as simply dressing.
I appreciate the encouragement you are giving us all to be ourselves.

Mary Contrary
1 year ago

I had kind of a scary experience in one of my early ventures in public. I felt confident at this stage of dressing and thought I could pass. I went to a JC Penney store downtown and headed up an escalator. Half way up There was a group of teenage boys going down and one of them said, “That’s a guy”. Terrified as I stepped off the escalator and saw the boys turn toward and headed back up. Fortunately the Lingerie Department was directly ahead . Hoping the boys wouldn’t have the courage to enter this land of lace and… Read more »

Jessica Scarlett Ray

Leaving the confines of the home I feel so comfortable as my feminine self! So liberated. A lot of anxieties build up without reality and we are own worse enemy and judge.
We might not be the best looking female but are we trying to attract the opposite sex or are we trying to live with ourselves.. That’s the question!?
I am transgender and in the last 4 weeks I have not felt so comfortable in my skin; going out as female; in all my life.

Cara Mason
10 months ago

Hi vanessa I have been out dressed as cara a few times been to local supermarket today I go in ladies trousers and top not been out in a dress yet although I have been out in a skirt to local postbox

Darleene Evergeen
6 months ago

I have and LOVED it !! I was being hit on within minutes of entering the club. I declined his request, but it felt amazing !!

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