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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My first time out happened about 5 years ago.I found a cross dresser entertainer who did make overs and I brought my own cloths.She did a wonderful job with the makeup and I felt great until I stepped out of her appartment. I thought every eye was rivited on me and even in her car I felt nervous. We went to a cross dressing show and even got a free meal on the house as we were cross dressed. The night finally ended but I didnt want to take off my make up or cloths. I felt wonderful and now… Read more »
I’ve done it….
Went out as Emily today, enjoyed every minute of it. I was a little bit nervous at first but after a few minutes had passed, I’d got into the flow of things and just enjoyed the day.
have a great new year
Kind Regards
Emily
Congrats dear! So wonderful to hear 🙂
Congradulations and way to go, girl!
wonderful to hear, Emily. I hope to do the same soon myself. I’ll keep you posted as to what happens.Lots of love, Ragina
well i am fairly new to cross dressing and io want to tell people but i find i cant. i mean i am only 15 and i should tell my mum but i’m not sure about it . should i tell her becuase i am not sure wot she will think of me. she has always been proud of me but will me telling her this make her think differently of me need some help here any advice
You never know how anyone will react. I am lucky that I have only lost one friends since I came out to my friends. Many that I thought were going to not take it well have been some of my best supporters. I have been very lucky. Many others I have talked to say that some of the most open minded people that they have told that they expected would support them turn them away and those they didn’t expect to supported them. You really just never know. I am now 42, and working on telling my Mom, who doesn’t… Read more »
The one thing I have going in my favor is that I know my mother already knows at least part of it, because when I woke up in the hospital after my car accident, They had taken my jeans off, so I was in the hospital in my shirt and panties. I did have a blamket over me, but I know that everyone knew. When they came to take me for a cat scan, I heard my Mom ask the nurse if she could give me two hospital gowns because she didn’t want me to be ambarrassed by amyone seeing… Read more »
I use to crossdress all the time starting in middleschool. My first time being seen was dressing at home (mostly mom’s clothes) and having a pizza delivered to the house. I opened door totally en-femme and paid the driver… my knees were shaking so bad as I waited for him to count out change…I just wanted to tell him keep it… but I was in school and money was in short supply. The driver never paid me or my attire any notice. I remember being so nervous I couldn’t even eat the pizza..hahaha.. After that I was hooked.. the rush… Read more »
Hello Sophie, I’m Ragina. Yes I think that you should tell Mom about your crossdressing as soon as you feel comfortable to do so. I speak from experience that it is better to tell her than to have her find out in an uncontroled way, such as catching you en femme without any warning. It can really lead to a very unpleasant confrontation that you just do not want. My Mom found out that way and it got ugly real fast. Fortunatly, after a while, cooler heads did prevail and we had a good chat about it later, after things… Read more »
thanks for the advice it was really helpful i have told her and she was shocked or suprised att first but things have been sorted out now and i think its all goin well now
Hi Sophie, Ragina here again. I’m glad to hear that the talk with your Mother went well. Remember to keep things on the up and up so as not to betray the trust that has started to build. This is a positive start. Always be truthful in answers to questions, and if you don’t have an answer, get on the web and get the information you need. Don’t try to BS your way around. Always be well informed and I feel that you will be fine. Best of all to you. Ragina.
Sophie: I came out to my wife recently. I was frightened to death of what she might think of me. She must have known something was up, because I suddenly became all lovely-dovey, hugging and kissing her every time I saw her, not sexually, but in a sad way. The truth was that I thought there was a chance that she might never want to look at or speak to me again. But I couldn’t keep it from her anymore. It was tearing me up inside. So one night I broke the news. She took it well. She’s a very… Read more »
i been out in public before and i found it liberating i found tht it gave my confidence and i enjoyed it yet i still havent told my family i dont no wot to do but i made a step in the right direction but any advice?
thanks for the advice it is really helpful and i wish u luck as well
I have been crossdressing for about 10 years now but have only been out in public 3 times , I did get a few comments on one occasion but I felt so empowered I didnt care , the reason I havent done it I think is because I will reach a point where I cant be anything but female and I am not sure what will happen then
This is the site I’ve been desperate for! You seem to have many answers that I’ve been asking for; only I’ve been asking empty space, not knowing where to look. Thank you for being here. Leah
I have to say I love the feeling of putting on a pair of panties and a bra, Ive beem a crossdress of 9 yrs.and I love slipping on a mini skirt and a blouse with nylons and heels. You might ask how I got started my sister when I was 13I went and told her that I want to try on cloths and she.Took me into her room and made me into her sister I dont think she realize that .I lovedbeing dresses has a girl. But over the next year she show me how to wear makeup do… Read more »
I just saw this article today, which is coincidentally the first time I’ve ever really been out while crossdressed, so I thought I’d share my experience. When I say “really been out" I mean out in a crowded area during the day. I have gone walking near my home at night while dressed, and even driven to a mall after hours and walked around the parking lot, but today I took a much bigger leap. I went to the store in the morning and bought a bunch of make-up, then I came home and set to work applying it, which… Read more »
You don’t have to appologize for a long post. ( At least I hope not, or I have a lot of appologizing to do myself! lol) Congradulations on your accomplishment today. The more you go out, the easier it gets. Once you start getting used to being yourself in public, you tend to stand out less because your confidence raises up as you enjoy yourself more and more and you get relaxed, then your don’t have that look on your face that screams “Oh my God do they all know?" Once you get to the point that you do not… Read more »
Ummmm, the first time was in Manhattan many years ago. I had been dressing and mking dresses with a friend at her apartment and mine. We would go to cross dressing groups but I would not dress to go. Then a couple invited us to their apartment for dinner and we accepted only after they accepted to come to my apartment. We had a lovely time and I cooked with my girlfriend for them and we talked and got to know each other as couples. The wife to the other couple wwas very open with me about my dressing adn… Read more »
the first time…it was bad and good. just not good at makeup, but a couple gg asked me were a local beauty shop was at. my voice croked out a ‘no’. getting out in daylight, all dressed up…..O how can one put it into words. if you long to dress and walk out the door. do it before you get too old. it is great. the excitment, fear, you are scared to death. but nothing happens and you have been addicted to being your self. it’s great fun. been some time back, had to lock up loni for a couple… Read more »