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!
Love,
Lucille
P.S. If you liked this article, you will love my FREE Unleash Your Inner Woman hypnosis mini session.
My first day out was earlier this month on my 21st birthday in fact. I decided to spoil my self on my birthday this year, earlier that morning I went to the mall and worked up the courage to get myself professionally fitted for a bra and left with my first, and currently only bra. It is a nude pushup bra and when I wear it underneath my clothing, it creates the illusion that I have breasts. After dropping the item off at home, I went over to Target to get my first pair of heels and some shaving cream. When I got home, I put everything, took a shower, shave my legs and face, and got dressed. Everything I wore that night except for the dress I wore was mine. While I wasn’t the prettiest woman in the restaurant, I felt like a million bucks, and pass better than I originally thought, on many occasions I was referred to with female pronouns and no one batted an eyelid when I was in the lady’s room. Quite possibly the best day of my life.
I’m transgender, and have crossdressed in public as often as circumstances will allow since I became aware of gender, around age 5 or 6 maybe. I have never been able to identify with the tag “male”.
I took a lot of flak from parents growing up in the 1960’s, with respect to hair and clothing, but I have always somehow been able to get away with wearing 3″ shorts. My mom still asks how I keep my skin so smooth and soft (Aveeno Positively Smooth, and a razor) 🙂
I’m kind of Tomboy Femme style wise, which means for me a bit androgynous, and reflects how I feel inside well;but it gives me some flexibility as well. I might be be more femme and wear a dress or short shorts and a T on one day or less the next when I might wear Boyfriend style jeans and a hoodie. My wardrobe now has very few clothes designed for “men” today, and my wife has been fine with that since we met.
I am one of the lucky CDs who has a totally supportive wife She encourages me to dress at home most of the time. We have been together for 15 years and she didnt find out until about year 5. She was pissed off at first but only because I had kept it a secret
I am a retired police officer and many years ago I was first on scene at an accident with injuries One of the injured was a CD and understanding his embarrassment I found a way to let him get changed before anyone else arrived. The other cars driver was so drunk he wouldn’t have known anything. Anyway, the guy I later found out was a very wealthy business owner and I let him know I was also a CD. We hit it off and one day he calls me and invites me to his home. When we arrived his wife answered the door of a house that had to be 8000 sq ft. She escorted us to the living room and and he was there wearing a very skimpy bikini. You could tell by the look on her face that she thought he was awesome and he really did look good.
Now whenever I wasnt at work I at least had panties under my cloths. Knowing that we were headed to a CDs home I also had put on a bra. I had been out in public a couple of times and with my wifes help I am smi passable, We sat around and had a drink and chatted and then he suggested we all go for a swim. I reminded him we didnt bring swimwear so he lead us to a room and there must have been 20 swin suits in all kinds and sizes, My wife picked me a stars and stripes thong bikini. She even found one for her. She is very tiny. We swam and played and had a great time.
About 2 months later he invites us to a big party at his house. Its a formal thing. He sends me to a shop he and his wife shop at with instructions to pick out evening gowns for both of us. He was buying. When we arrived at the srore they were expecting us and we got the royal treatment. We both had the dun of trying on several dresses. My wife chose a very short backless dress and she is very slim so she picked out a floor length gown. They even got us matching panties and bra. He even had a limo pick us up.
The night of the party we arrived and found there were 20 couples and all of them the man was a CD. We had a really great time . Since that night we have been to several parties and private time with him and his wife
Im 70. have been wearing ladies underwear then clothing at home for about 3-4 years. Wife has been supportive. Then I got the courage. Went to MAC cosmetics for a 90 minute make up training season with wife. I wore gender neutral top. No one said a thing about my makeup at the restaurant. This weekend going out in more female attire. I have been growing my hair out and growing breasts- 6months now. So far no dress worn in public. We will see how soon. I do that . I taking it one step at a time as I feel comfortable.
Several years ago I had a woman friend take me out fully dressed to a huge nightclub in Ft Lauderdale on Halloween. We had to park and walk 2 blocks to the entrance and I knew I was going to be arrested or have a heart attack in the street. IT WAS AWESOME night for me wearing a dress, heels, nails wig and full makeup. Then on the 3am strut back to the car I got lots of inviting stares from men and then 2 cuties walking behind us ran in front of us to turn and stare at me. Guess I am passable from the back. I still see her occasionally, no sex, Normally I dress and cook and have her over for dinner.
Hi, I am 62 years old. I cross dressed very sporadically from my childhood till my 40’s. but spend most of my life denying my feminine desires. I started cross dressing more in my 50’s and am now starting to feel that I am trans even though I present myself as a man. The woman that I am has been quietly persisting, begging and demanding expression in my life. I have come to love her, the heartache of Year’s of denial is fading as I am learning to embrace who I really am. I started to wear panties exclusively every day 9 months ago. 4 months ago I started taking pueraria mirifica and my body is beginning to feminize. My breasts are growing but are barely noticeable even under a t shirt and my bum is growing nicely it has some jiggle and is more rounded and I feel different mentally and emotionally.
This has all lead up to the first time that I stepped outside dressed as a woman. I have a new friend who is a trans woman. She invited me over to sit on her balcony and sip lattes. I got changed, dressed fully as a woman including a beautiful wig but no makeup. As she was making the lattes, I stepped outside into the sunshine and stood at the railing looking down from the second floor at the passers by and felt wonderfully feminine as I realized that this was the first time that I had ever stepped outside as the woman that I have wanted to be.
I know this sounds very tame and it barely qualifies as being in public but it was a milestone for me. Next she and a girlfriend of hers are going to help me to be presentable and take me for a walk, then to lunch, and then shoe shopping(gulp!) I am excited to be going outside and walking down the street, but just a little terrified to go for lunch and shopping.
I don’t believe that I will ever fully transition and although taking “PM” is feeling addicting, I will soon have to stop taking it before the changes become too noticeable. But I am so grateful for the opportunity to walk down the street as the person (woman) that I desire to be.
Thank You for reading about my experience,
Tetanya
I am sitting here wearing a very feminine bra (what bra isn’t feminine?), breast enhancers and a long pink gown. I will never, ever go out as a woman! I do occasionally wear hose and panties under my clothes and I have a few pairs of women’s jeans that I wear out but that is it.
I would so much enjoy going out to a beauty salon and getting made up….WOW! Just talking about it makes me flush with excitement!
Denise
Just do it. Go as you, not a woman, you. I dress every day and it’s wonderful. Don’t over do it or be slutty. Wear age appropreate clothes, nice make up and comfortable shoes. Study the ladies, watch what they wear and don’t over do it.
Have fun and enjoy yourself.
Hello everyone!
I have loved reading your stories! Brace and inspiring. I’ve been wanting to cross for a long time, and just recently my wife (of 6 months now) has completely accepted that I like cross dressing, loves helping me get dressed and everything.
Even a friend has been around and seen me. All very cool and understanding.
Thing is, I’m not really looking to be passable per say. I have a beard and don’t plan on loosing it, don’t have any desire to be a woman. Just want to be a confident man in women’s clothes.
Which I think scares me even more of going out publically. I won’t be in disguise as a woman so to say. I’d be waving a flag haha.
In my head I know I’d be exhilarating, just terrifying right now.
Not sure if I have questions or a real comment, I just haven’t noticed too many bearded CD’s.
I guess sort of feeling like an outsider in an outsiders world?
I sympathize with you and totally understand
My first time was when I was 14. I had been wearing my older sister’s clothes for a few years. It was early evening in the fall. I didn’t go far, just a walk around the block, but it was wonderful. Jeans, blouse, and a pullover sweater. My hair was almost shoulder length and could be styled to look more feminine. My sister combed it once and told me she liked it more that way. Inside, so did I. She knew what I was doing. Will always remember my first time!