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.

EnFemme

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Aileen' class='avatar avatar-64 photo' height='64' width='64' />
Aileen
8 years ago

Similarly to others I’ve been staying inside our home when dressed en femme. Recently I went on travel. I took along my lady things intending to spend the evenings in my motel room practicing wardrobe and makeup. I worked up some courage, grabbed my room key, and stepped out into the hallway. No one was there, so I walked down the hallway intending to do an about face and return to my room if anyone appeared. No one! I went to the lobby, still no one around. I got a cup of decaf and returned to the room. I was… Read more »

Ashleigh Parker
Ashleigh Parker
8 years ago

Funny you should mention about the police. We are our own worst enemy when it comes to worrying about being “found out". We always assume people are more observant than they really are. My first real experience was similar. I, like most everyone else, had/have been dressing in the privacy of my own home since I can remember. I did venture out once in my early twenties with a very short skirt, sweater type jacket, bra stuffed with socks, and panty hose that did not fit well (all my wife’s things). I had a scarf wrapped around my head and… Read more »

Maxine' class='avatar avatar-64 photo' height='64' width='64' />
Maxine
8 years ago

My story is a little different in that I hadn’t been dressing all that long but with the full support and encouragement of my (new) partner. At the beginning of a 6 week holiday to New Zealand, we decided to remove all my body hair which we did with great success. We practiced the makeup & wig, getting the clothes right & walking for a while before venturing out the first time so by the time it happened, my confidence was reasonable. Although still mindfull of many things that could go wrong, I had the opinion that we should aim… Read more »

Erin
Erin
8 years ago

The first time I went out dressed was last August to go a friends birthday, it was at a bar, and it was going to be like 80+ people. One of my friends convinced me to go dressed, I was scared I said no like 10 times but eventually I said yes, I know how to do make up and had alot of clothes and shoes but I just never wore them outside, I was always scared. But after that night I never wanted to dress in male attire anymore. I thought the whole room was going to get awkwardly… Read more »

Christine Charland
Christine Charland
8 years ago

There was a time when going out en femme scared the hell out of me. I try to see why I was so afraid back then and there were many reasons but most of them go back to how I was brought up. Sound familiar? Dad and boys and all that macho stuff that just doesn’t look good on your sleeve. I’m not going to write a book here about how i got beyond everything because……well it’s different for everyone. It does help to have some support and that I can do. I came out to family over 20 years… Read more »

Caroline' class='avatar avatar-64 photo' height='64' width='64' />
Caroline
8 years ago

What a lovely piece, Vanessa, and how identical a story to many of ours’. As I live on a small island, it was always difficult for me and the situation was made worse by two facts: 1. my wife did not know anything in the first few years and 2. my work is in the public forefront, so it is always a risk being identified. My first outing was in the UK during one of my frequent visits there. Girlfriends and sisters within the Beaumont Society helped me prepare but I was still terrified. My first public “appearance” was for… Read more »

Caroline' class='avatar avatar-64 photo' height='64' width='64' />
Caroline
8 years ago
Reply to  Vanessa Law

Of course, please go ahead, Vanessa. Unfortunately I cannot submit a picture due mainly to the reasons referred to in my short piece. Love and peace.

Charllotte Kerr-Scott
Charllotte Kerr-Scott
8 years ago

For most of my life, from the time I was about 8 years old, I just so wanted to look like a girl and to walk about wearing girly things. This was in the late 1950s so you can imagine that it was a fantasy dream in those days. Gradually, attitudes and opportunities have changed. Around 10 years ago I went to a cross-dressing agency, in London, I had found in a magazine. They had me out, fully made-up, dressed in high heeled boots, smart skirt and jacket, checking into my hotel and walking down Oxford Street in London doing… Read more »

krnharris
krnharris
8 years ago

I am so afraid of telling everyone of my first time out because it was so many, many years ago. My wife was going to be gone on business for a week so I decided to take that same week as a vacation week. I was so excited and scared at the same time. I planned each day and what I was HOPING I could do but of course this did not entirely work out. What with my wife calling and a couple of friends coming over un-expected it was not quite how I had envisioned it. At any rate,… Read more »

Amanda Trane
Amanda Trane
8 years ago

That oh so scary, yet oh so exciting first time out. For me it was scarier to stay inside as my GF’s daughter had woken up and come out to get a glass of water after I had gotten dressed, done my face, and sprayed my hair into submission to relax for a few hours ‘enfemme’ as after a few days of babysitting for her I knew the kids never woke up. I bolted out the patio doors of the apartment and rushed around the side of the building hoping she hadn’t been awake enough to notice me standing there… Read more »

jessica humphrey
jessica humphrey
8 years ago

I have been out for a long time.I first went out dressed as a young girl at the young age of 5 .I guest I always knew I was meant to do this and have since then wore womens clothing,makeup and the whole nine yards. I love myself and know that there are some of us who are affraid yet to come out but in time and when you can love yourself ,you to will be able to come out.

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