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.


More Articles by Vanessa Law

View all articles by Vanessa LawTags:
4.5 4 votes
Article Rating
Notify of
Inline Feedbacks
View all comments
Mia West
5 years ago

I found a link to this older post in my email I thought I would reply. Over the last year I have been going out and exploring mostly to friends houses, a few walks, and even to a couple corner stores. Last week I took a really big step and went out to a Lorde concert with some friends. I had an exhilarating time and it seemed magical. Walking around so many people all the fear had melted and I was not nervous I felt comfortable in my own skin as my self and that was so liberating. Every time… Read more »

Stella' class='avatar avatar-64 photo' height='64' width='64' />
5 years ago

It has been a dream of mine since the mid eighties but as yet unfulfilled. It is tough living on a fixed income and having to buy to separate wardrobes. these days all my clothing comes from thrift stores except for under things. Three years ago I bought some lingerie from HerRoom.

PY Marshall
5 years ago
Reply to  Stella

Stella I would think about 75% of my wardrobe contents are from carboot sales and charity shops and ebay the rest is new . And my wigs are bought on line. PY.

Joanna Knight
5 years ago

Never have in the day time yet I’m not sure I can! I have been out many times at night to smoke a cigarette at night when I know no one can see me dressed as my feme side I have come to enjoy going out at night to smoke a cigarette ! Where I live we cant smoke inside so I have to go out my front door to do so ! I love being me in feme ! I just bought me 2 new High-Waisted Bikini’s that will be in this week so I can see what I… Read more »

PY Marshall
5 years ago

Hi Vanessa and the other ladies. the first time I ventured out in daylight hours was just after making a pair of longline leg shapers with a bum enhancer combined. I had been watching a drag queen making a pair on Youtube and thought that would do me perfectly. They were just so successful. to be able to ware them I purchased a electric carveing knife £8 an elasticated body girdle which when on goes from the knee to over the tummy the same as the drag queen used . I think under a tenner. £10 My wife made me… Read more »

Deni Hale
5 years ago

I have been dressing and sneaking out under cover of darkness mostly. You know, getting dressed in your car and cruising ateas to meet guys. I recently joined Trans Ladies of Baltimore and after reading crossdresser heaven stuff, I decided I’m going to for it .

A meet and greet at a local bar, full of young lesbians btw, me in my split front little black dress, I showed up and had a wonderful time. There is quite a bit more to tell, but heck it’s my bucket list begining to fill.

Deborah Jennings
Deborah Jennings
5 years ago

I well and “truly” came out on the Saturday 29th September. The time was just after dark when I knew that people would still be out and about around where I live either on foot or driving so I would definitely be seen. Since I was coming out I had bought my outfit on line all in pink. So I was dressed and made up under a black Bob wig and with a slave chain padlocked around my neck, a tight pink long sleeve top stretched over and showing of the d d silicon breasts that were jutting out in… Read more »

Catarina' class='avatar avatar-64 photo' height='64' width='64' />
5 years ago

I said before that I didn’t go out en femme yet. That is true and untrue. Looking the way I do as a man (somewhat broad shouldered and bearded…), it is far from evident to transform in a totally convincing way. Maybe some day I’ll try that. But some 10 or 15 years ago, I found a way to satisfy my oh so strong longing to dress up and go step sipmly out in the world as a woman. I had bought a pantyhose of a very thick Den number, and not the most convenient colour for women (something brownish… Read more »

Jennifer Love
5 years ago

I like some many of us was deep in the closet, only dressing when the coast was clear at home. I was lucky enough to have a couple of on line girl friends who I could chat with about my desire to go out en femme. They told me to start slow, maybe go out side my door, which I did when it was dark, then I took a drive at night, it was scary especially when I would come to a red light. I just knew the car next to me would ID me. Finally I found a gay… Read more »

Alysson Manson
4 years ago

I am full time and the looks and hate that comes my way ,it takes some strength to pull this off ,old farmers and church haters are my biggest threats in public, with freaky people I am a hit , I live in a rural town of 10k in Missouri ,this has been eye opening to me ,now I know how it feels to be on the outside being laughed at ,the stares ,fingers pointing , I cant even carry my purse without hate coming back my way , nothing can get you ready but a strong skin and some… Read more »

Dani Daniels
4 years ago

my vencher out was anti climatic my first time i spent the whole day in annarbor michigan then went to a LGBT bar. no one even gave me a second look just some smiles mostly women. and i talked to a guy for about 20 minuits. i dont know what i was afread of. there still was a bit of an bathroom issue the secound time i went out.


Would love your thoughts, please comment.x
Subscribe To Our Newsletter

Subscribe To Our Newsletter

Join our mailing list to receive the latest news and updates from Crossdresser Heaven.

You have Successfully Subscribed!

Log in with your credentials


Forgot your details?

Create Account

If you don't see the captcha above please disable ad and tracking blockers and reload the page.