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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Hi Vanessa, your article brought back many memories. I was historical. I knew I had to step out dressed and I walked towards that door literally 100 times before actually stepped outside. I was so paranoid I had rented a motel room in a nearby town to make m first foray and I knew, just absolutely knew that ALL the people in he motel looked out of there Roms at that moment and where laughing hysterically. That day was the first step. I am now legaly female and work as a cashier at a major retailer in a conservative southern… Read more »
Hi Kelli Anne,
Hehe – it’s amazing how everyone has perfect tranny radar, and know just where to look isn’t it 🙂
Congrats on your successful transition dear, it must seem like so many years and memories away from the first time you ventured out crossdressed.
Hugs,
Vanessa
I practiced for about 1 year before I first went out. And even that first time out was at about midnight so that no one could really see me.
After a few times out in dark of the night, I started to go to a transsexual / gay club. I would change in my car and spend the night as Carolyn. It was an accepting and supportive atmosphere and I needed that. However, I am really not into the gay scene.
Now I’m fulltime and will be having SRS in March 2010.
Go girls!
Congrats Carolyn – phew, that must have been a long year or trepidation for you dear.
I guess my first time was as a kid, but it was halloween. I said I wanted to go as a girl and my mom threw everything together on me and made it comical. I still had alot of fun, but it wasn’t the outfit I would have picked out or the look I was after. It made for a fun night trick or treating but did not do so much for reaching into the real me. As I got older, as most crossdressers do, I dressed up as myself for halloween, or at least as a female character. Many… Read more »
hi im a new crossdresser out of the closet . i live in a small town hear in cal and i try to go out but i git so far and i git nerves and go back home thar is no one hear for me to help me git me over the shaking nevis that i have is thar eny one out thar close to me to help me out i live in orland calafona . help plees
Hi Kimberly, the best advice is to take it slow, and to try and find a local crossdressing support group https://www.crossdresserheaven.com/about/crossdresser-support-groups/
Hi, I am still in the closet but use all the opportunity I could get to crossdressed. My wife is going away for vacation in a few weeks and i am looking forward to crossdressed during that time. I am also looking this time to try to go out for the first time, just hope I will be able to do it. Have a Merry Chrismas to all.
Suzanne
Suzanne, Going out for that first time when you are married is definitely scary. I have gone out a few times when my wife is out of town, always worried I would see someone I know. Or worse, they would see me! Last time, I convinced myself that I would just go out and have a great time. I got a massage from a wonderful therapist who turned out to be very supportive and sweet. (She had a boyfriend, though. Otherwise, she said she would have loved to go out with me!) Then I went out for a late dinner… Read more »
Wonderful advice Alex!
Suzanne, good luck as you venture out. Make those butterflies fly in formation 🙂
Suzanne I would like to go out with you I
Have only gone out dressed up three times and would like some one to go out with
Suzanne lets do it e mail me frank an 1947@gmail.com
Suzanne I left a reply but have not heard from you lets go out some place looking good and feeling better dressed up like beautfull women
hiya Suzanne, Same here I’m still in the closet where going out is concerned, the only people I’ve come out to is my friends and family. However as a male I do amateur photography and going out with professional grade equipment was something quite nerve wracking at first, people looking and commenting on the size of my camera, but now when I go out I don’t even notice the comments anymore, just focus on great photographs (landscapes and macro). Hopefully it will be the same if I decide to go out crossdressed as Emily, like the photographic side, over time… Read more »
What a great analogy Emily. Anything we do that is different can draw comments from people. Most of them are probably just curious – we shouldn’t let other people’s interest stop us from doing what we know we should be doing. Let your crossdressing muse make artistry in your life 😉
I attend a group based in Blackpool, UK, at an small hotel. Please visit the website, by putting renaissance blackpool in the search engine. A couple of weeks ago I was able to get to Gynway (the Hotel), and dressed about 10.am. Petra went out shopping, but I was able to chat with a rather poorly Lynda. I then decided that I would brave the big wide world for the first time! I walked down to the Prom’ (ie sea front), (grey pleated M&S skirt, pink top with cardigan. I thought the front, being deserted, was not a place for… Read more »
Wonderful Sylvia, thanks for sharing! Even if you were read, it’s great that the shop assistant was still polite. I find that even when I’m read people are generally courteous – very rarely will someone make a scene.
For any ladies looking for a support group, you can find the web link to Renaissance and others here https://www.crossdresserheaven.com/about/crossdresser-support-groups/
I attend a group based in Blackpool, UK, at an small hotel. Please visit the website, by putting renaissance blackpool in the search engine. A couple of weeks ago I was able to get to Gynway (the Hotel), and dressed about 10.am. Petra went out shopping, but I was able to chat with a rather poorly Lynda. I then decided that I would brave the big wide world for the first time! I walked down to the Prom’ (ie sea front), (grey pleated M&S skirt, pink top with cardigan. I thought the front, being deserted, was not a place for… Read more »
Hi all, I too am from the UK, but am currently ‘closeted’. My wife is supportive and a few close friends know too, but I doubt to whether I could ever pass as a woman on the street, which makes me feel quite sad. I also have young children too and don’t want to cause them any distress either. I am however trying to find the confidence to go out crossdressed for the first time (other than to a fancy dress party – how I love those), but I live in a small town in which I would no doubt… Read more »
Further to my entry above – I have been out shopping “en femme" several times since. I have again been to the shop I mentioned, and they are friendly.
I am trying to push the boundaries out, (ie using a restaurant for coffee, using the Ladies’ room, public transport etc) and taking every opportunity to interact with other people. Having a lot of fun, too! I hope my “english" isn’t confusing,
Hi Sylvia, I’m Ragina. Congratulations on your explorations. You are Breaking new ground for all of us. I only wish that there were more here in the states as bold as you. Perhaps then more of the “strait" world would not be as judgemental and condemning of the transgendered community, if they could see that we are just people, perhaps different in some ways, but people nonetheless. Good luck in what you are doing, and please, keep us all posted as to your progress. Love, Ragina
Hey Maddy,
Support groups are always a great place to start. If there isn’t one close by, perhaps going for a drive in your car would be a good way to be ‘out’ without the fear that you’ll run into someone you know.
Back in the mid 70’s was when i first started going out. i remember it well, i wore a short black skirt, red blouse, and suntan stockings. Had penny loafers on my feet . I threw my purse over my shoulder and out the door I went. still remember my heels clicking on the sidewalk. Now Im old, but went out last night, and guess what. I was wearing a skirt and blouse, suntan stockings, and my Mary Janes, and when I put my purse strap over my shoulder and went out the door….. the door, it was yesterday once… Read more »
Thanks for the advice Vanessa, I think a car drive ‘en femme’ is very much on the cards! Your site offers an invaluable lifeline, despite being the other side of the Atlantic.
If you’d indulge me, I’ll let you know how I get on – I know it’s a comparatively small step to what many have gone through, but it probably has some relevance in this thread. I think 2010 could be very exciting!!!
Love to all, it’s been a genuine boost reading everyone’s experiences regarding their first time out. xxx
I'm glad I came across this post. I had to meet up with my business partner a few days ago. I also needed to stop in my cross dresser's store because I needed a few things. Well, he was early, and the store closes early, so we met and I kind of rushed him so I could get back to the store and change into my girl clothes! I got there just prior to closing, but they were kind enough to let me changed. I had to put make-up on in the car, tho! What a challenge. Then began the… Read more »
When I first went out back in 1975 I wore a black skirt, red blouse, and penny loafer flats. I wore plain suntan stockings, and a brown page. I swung my purse over my shoulder and out the door I went. I got to thinking that the other night I had on my gray skirt, suntan hose, purple sweater, and Black Mary janes. My hair style is longer now but I look near to what I did 35 years ago. when I swing my purse up over my shoulder its yesterday once more. carol