Stepping out publicly as a woman is a powerful way to validate your female self.
In fact, I recently published a poll asking “How often do you go out in public as a woman?”
I was happy to see that the majority of my readers (transgender women and crossdressers) go out at least occasionally.
No matter how often you do it, I’m sure you can remember your first time presenting as a woman or crossdressing in public.
Since this is such an important gender-affirming step, I’d love to hear about it!
When was it? Where did you go? And what was your experience?
Please share with us in the comments below!
And if you’ve never been en femme in public, I’m sure you’ll find lots of inspiration in these stories.
As always, thank you for reading and participating!
P.S. If you liked this article, you will love my FREE Unleash Your Inner Woman hypnosis mini session.
My first time was about thirty-five years ago. It was Halloween and my then wife and her girlfriend and I were going to a costume party at a bar. They dressed me all up in one of the wifes long dresses, heels and wig along with a bra. they did my make up and I was looking hot. We went to the bar but didn’t win any prizes so we left and went to get something to eat at a resturant. We went in and everyone started looking at me. The waitress asked for our oders and when she asked me and I started to talk she about fell over and she swore that I was really a girl. Then everyone in the place got in on it. Fast forward about tenty yaers or so and that’s when I started dressing every chance I got. If I was off work and the wife was at work I would dress and go driving around town and drive to the mall. There I ould get out and walk to the ATM at the bank and then off to home. It was exciting.
The first time was over thirty years ago in a bar on Chicago’s north side named The Lite Factory. It was CD friendly. (It’s no longer that accepting of us). It was a weekday and there was only one other cross-dresser in the place. We bonded immediately and spoke with each other the entire evening. One of the other patrons, whom I later found out to be interested in CDs, bought me a beer. I thanked him politely and showed him my wedding rings.
I really enjoyed being treated as “just one of the girls”. But my biggest thrill came after I left and was walking toward my car. The street light cast a shadow in front of me of a woman in a dress (my wife’s) and heels. I realized with each step that woman was me. It was a divine feeling! I also noticed that the hair style of the woman in the shadow was too short and out of proportion to my body. Something I had never noticed in my mirror at home. Also, in one of the mirrors in the bar I saw that the blond hair color tended to “wash out” my facial colors. So I quickly bought a wig in a larger style in color 27 and I’ve been a red head ever since.
There have been many other times since then but you can see the memory of that first time is still vivid in my mind. It was the first time, but not the last time, that I’ve been respected as a woman and treated like a lady. It’s always been exciting!
August 1960 a few days after escaping from borstal in Liverpool aged fourteen. Stole some washing from a line and found a frock that I used as a disguise and to prostitute myself in Manchester and Liverpool as a transvestite child prostitute. Survived for three months living on the streets and eating out of food bins before getting picked up by a third engineer off a ship in Manchester and I got a job illegally and under age as a cabin boy. I became the plaything of a paedophile ring on the ship until they were caught.
Hello, well i dont remember when i uses girl clothes first time, i remember that i uses skirt in kinder garden, in teenage i try to uses unisex clothes but it was very hard for me, later i have great fear because i didnt know why i feel it, why i feel woman if i have boy body, mmm i hate born this way, today i fixed my papers and reestudy high school and practice ballet, i’m happy now
My first time out was about 1 yr ago. I went alone to the local drive-in. I was way early and sat in my car that was second from the front…easy view from the ticket lady. All went fine with getting the ticket when they opened the gate. Parking my car in the ‘audience’, I sat patiently, reading, when a lady from to drive-in approached my car. She said, “Mam? Would you like to buy a raffle ticket?” My mouth was full of a swig of coffee so I just nodded no and she left. I was thrilled about the ‘Mam’. A pickup parked next to me. There was a young man, probably late teens, practicing his guitar. I stared and listened to him play. When he noticed me, he smiled and said Hi. I said hi back. I didn’t catch any notice that he suspected anything. He did peek over a couple times but I think that was just a young man staring at a pretty lady. After the drive-in, I went to Walmart. Hardly anyone was there [It was about 1:30 am]. I walked around the store just practicing my walk and being fem. By now I had to pee. I made the decision that it would be less odd for me to go to the Womens’ Room since I was, after all, dressed for the part. The Womens’ room was right next to the only register that was open. There were 3 or 4 ‘kids’ [Walmart workers] hanging around like kids do. I walked right by, ears tuned for anything that may be said, but everything was perfectly fine. The only problem I had all night was leaving Walmart. As I was walking towards the exit, 2 teen girls and a guy were coming in. One of the girls saw me and said, “Oh My God…” to her friends as she stared at me. She had a rather startled look on her face. I stared back at her, smiled and kept on walking. All in all, it was a Great Night for the first time out.
“Maam, would you like to buy a raffle ticket?”
Enchanting moment, with (or without) coffee.
Thank you for sharing your story!
I remember back in December 17,1995 going shopping my clothes and I was a nervous wreck. I wore a black sweater, black skirt, black pantyhose, and black heels. I was a blonde and my makeup was terrible. I couldn’t talk like a woman but I can now. The clothing I bought a quarter of it was the wrong size for me. After that experience, I learned to do my homework on how women dressed, wore makeup, and acted.
As a kid, I would take about a two-block walk at dusk. When I could drive, I’d go to places that were easy to zip in and out of, like the ATM, free newspaper machines, self-service gas stations, cemeteries, and soft drink vending machines. I haven’t thought about those days in a long time because they were filled with fear, yet completely uneventful. So much of transition happens in baby steps.
The first time I really remember, where I was actually seen by people, I went to the mall with my mom and sister in law. I still needed to shop for clothes and get my ears pierced, which I picked up some clothes and holes in my ears. I was, of course, terrified. I was slightly upset at questions shouted in a busy hallway about whether that was my real hair, it wasn’t, but was told that’s normal for a woman to be asked, so I didn’t let it bother me. I didn’t have any bad experiences that day. The salon I go to for electrolysis, when I have money, is always super friendly and I haven’t had a single problem there even dressed up and unshaven.
Your mom and your sister-in-law with you dressed at a mall!
How special! ❤️ I imagine that more outings followed of
the three ladies.