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 time was aged around 16, I was staying at my sisters looking after her house for the week, As soon as her and her young husband they left in the rented car I raided her wardrobe. A wonderful two days and a pile of beautiful clothes later at breakfast I realised that I had run out of food, of course I was already fully made up and dressed and had little alternative but to go shopping. It was about 8.30am luckily I had toned my make up down my day wear remembered what my sister wore on a local shopping trip, applied extra mascara, did my hair in a short pony tail and stepped out in a mini, sweatshirt and ballet pumps, preening at every window along the street. I did the shop, had a coffee, the ‘whistles’ and shouts from a group of builders and the ‘good morning lovely’ from a few older guys (which I loved) the ‘what do you want sweetheart’ and small chat from the shop lady just made my heart sing and I moved my hips and pushed out my ass out further. God I was so in love with being young and female that I nearly danced and sang my way up that sun filled street in Manchester and so wanted it to last forever. Three weeks later my sister had been told by all the neighbours of the pretty young thing looking after her house and who was she and challenged me … I left in tears with her ridicule and cynical snide comments ringing in my ears…Forty years later looking back through the hell of acting male whilst being a loving woman inside for many years…I have to say how lucky young trans-genders can be today and how much equality was worth fighting for.. and what a turning point it would have meant in my life if my sister had shown understanding and support. She is about 5 years older than I and had encouraged my girly dressing when I was aged from 5-10 years of age as part of our childhood play time. I discovered much later how my father in the 70’s and 80’s had shared similar traits to myself and how his gender issues had nearly cost him his marriage and had gone a long way to causing him a breakdown and mental health problems…its a mixed up world when you have gender dystrophy…things are a lot better now…. love to you all Vikky
With a frame size of 6’4″ and then at hefty 220 lb, I am not the
shape, to pass as a woman in southern Chile, as the descendants of the original Patagonians and of the Latins were of much smaller size.
I was engineer on a motor yacht and on my day off, I had a shopping spree of all new sorts. Inspired by a transgender forum in the Internet this was the set day, I spent lots of time in various
boutiques, ladies departments in clothing shops and sports fashion
outfitters. the salesladies made fun of me, I played along and got
very useful advice, my appearance changed substantially. First buy was a jeans skirt, which I put on right away, a fitting jacket I found in a 2nd hand shop.
People in the streets were turning and looking or was I only more
aware of this? Finally i had changed completely and carried the ‘man’
in my shopping bags plus more blouses and skirts, tights and even
shoes, althogh difficult to find, as supply was very limited at size
16.
I opened my Hair, which i wore long in a pony tail, I felt great, and
enjoyed all day in the city.
When I returned to the ship, i passed through the village with the
Fishermen looking up from their work at the nets, ropes and other
gear. They were always looking up from their boring work but now it
seemed more intense. Boarding the ship the captain gasped for air,
seeing his engineer changed to a girl, unable to say anything, the
cook bursted out in loughter but found my appearence not bad at all, his wife agreed, advised me on details and offered to join me on my next shopping spree.
In all, nobody cut my head off, but the captain advised me, not to
appear like this in presence of the owner family. Ok, fair enough, as
we were to wear uniforms anyway when they were here. only, that I
replaced the shorts, which came with the uniform with a skirt of the
same colour, not to be spotted at first glance.
Did anybody notice? Certainly, but no one said a thing…
Greetings, Charlotta
I have been dressing for a number of years, mainly in the privacy of my own home. I met a nice guy online from Minneapolis on one of the crossdressing sites. We chatted with one another regularly for a few years, and finally decided we wanted to meet one another in person. He only dates crossdressers and really wanted to meet me. We set a date, a long fourth of July weekend in 2012, and I flew to Minneapolis to meet him. He picked me up at the airport, I was not enfemme, but he did not care. He paid for a nice suite at a very nice hotel near the Mall of America. The first evening, he wanted to take me to a local club in St. Paul. I showered, shaved and got all dolled up. I wore a nice blouse, and short black skirt, black thigh highs with garters, red heels, bra and panties. He was so excited when I asked him if he would hook the straps on my heels.
As we prepared to leave the room, he kissed me and told me how wonderful I looked. He also thanked me for getting dolled up for him. He knew I was very nervous, so instinct kicked in and he grabbed my hand. That really put me at ease. We arrived at the club in St. Paul and a few gurls were outside at the entrance. They smiled and said hi to me as we walked in the door. A show was going on, so we sat at a table near the stage to watch. Another gurl I knew from Minneapolis met us at the club, and introduced me to other gurls. My date made me feel so at ease. It was probably the most liberating I have felt as a woman!!
The next day, he had plans to take me to a very nice restaurant in Minneapolis for dinner. It’s one of those fondue restaurants. We first went to the Mall of America to find him a nice tie for his suit. I was dressed in a tan, suede skirt with a light tan blouse. Since I was so comfortable the night before, I did not think I would have any problem being at the Mall of America. Boy was I wrong! I was not prepared for all the families with young kids, groups of teens and other couples. My date could see how nervous I was, so he put his arm around my waist and pulled me close to him. He said “relax, things will be okay. No one will say anything to you.” As we walked thru the mall, I felt like all eyes were on me! I could not wait until he bought his tie and we left. He took me to a quaint restaurant for lunch, and when the waiter said “ma’am, what would you like”, all nervousness left me! He was calling me ma’am and I felt like I was accepted as a woman! That evening I got all dolled up in a new burgundy dress I bought for the occasion. We arrived at the restaurant and had the most wonderful dinner! The waiter kept calling me “miss” which made me feel really at ease. I think he knew my story, but he was still more than accommodating and attentive to us.
The weekend ended much too quickly! We parted ways with a kiss, and still chat when we can. We are making plans for a long weekend in Las Vegas in 2015, with me as Teri the entire time. I found a store that will do complete makeovers. I mentioned it to my friend and he told me he wants to pay for it and anything else I want! I think 2015 is going to be a very good year for Teri. I am hoping to go to some of the local clubs in the Chicago area and let the woman in me out completely!
A special “thank-you” to Lucille for this great website and for all the tips on becoming a total and better woman!!
“Teri”…”Sweetie”…”Fantastic Story”…”I Remember My First Date With My New Cute, Sexy Boyfriend” !!!
“Trri”…I Forgot To Say How Pretty & Sexy You Look !!!
When I finally went out fully dressed for the first time I met a classmate from my college at a local gay bar. They had a drag show that evening. I had on a very nice flowered dress and impeccable makeup. My friend didn’t recognize me at first. She was very surprised by my presentation and was quite complimentary. I was introduced around and most people didn’t realize that I wasn’t a woman. That was twenty years ago, now I am living what I could only dream of back then.
Hi Lucille: Want to thank-you first for all your help!! I know I don’t get to respond back that often. I was about 25 their was a Halloween party at a local bar. I asked my gf if she would help me pick out all I needed to get complete we went shopping got my pink pantie and bra set a pink cami and garter, stockings from the mall. Then we went to goodwill found a blond wig a little black dress 3″ heels. That next Saturday used the whole day to get ready my wife did my makeup and my nails. when we got their no one reconized me not even my brother. Had a blast 4 girls dragged me into the womens bathroom hiked up my dress they wanted to know if I went all the way with the lingerie they were exstatic that they were pink and they were all their! I was loving every minute of the whole day and night! When they gave out the prizes for the contest I got second place will never forget that rush.
I had dressed up for my partner and my combined “Over The Top” themed birthday party, I felt awesome, but still wanted to go out in public. So a few months later we both got dressed up to go out to a bar. I shaved my legs, put on new sheer stockings, a new black sequined dress, white diamante 6″ pumps, and did my makeup, and put on a wig. We drove out, and it felt wonderful. We arrived at our destination, parked, and I got out. I felt like :wow, this is it!” We couldn’t find the walkway to the bar, so asked a couple of men walking along the street. They indicated it was down a flight of stairs, and one of the gentlemen took my arm and helped escort me down the stairs!! Wow, I felt a million dollars, I had obviously passed without any problem! We walked into the quiet little bar, and sat there drinking, listening to the music and talking with the barman. My partner took several photos. I then went to go off to the bathroom, and walked straight to the Womens door. This also felt wonderful, just to be in a different realm.
We left several hours later, and driving home I felt fantastic. Later I looked at the photos, and the smile and glow in my face shows that I was just so relaxed, and happy.
My first time??? Oh, God please don’t let me get there it was awesome I was 13 years old, I was alone in my grandma’s house and I was so in to it because I was going to “guard” the house since she was going on a short trip and I was going to be alone… with my aunt’s clothing oh my… she dressed so nice so I started first by taking a bath, shaving my legs and my armpits, then I put my make up and my lipstick then went into my aunts bedroom and opened her bedroom and ran over the closet I didn’t see anything wrong and started to go to her drawers get her lingerie, It was 1967 so she had beautiful lace underwear so I tried one and another and was so into it that I thought I’m in paradise, she just got married so it was the perfect day to be all day dressed, to get out and walk over the neighborhood I kept trying one thing and another that I didn’t noticed that my aunt got home and she was staring at me how I was changing until she said I like how that pink garter belt but you can’t have it with my sky blue panties so she stood up and went to the drawer and started to pick up the underwear to match and the stocking goes nude said her while I was ICE COLD and with this dress she kept saying you will look beautiful and I couldn’t believe what she was saying it was like she was enjoying this with me so she picked me some high heels then she asked me if I wanted to go for a walk and I said of course so we hop into the car since she had some things to do in downtown, so we parked the car and started walking getting in and out the store and suddenly some friends of my aunt that was 21 years when she got married and I looked older since I was tall but skinny so she presented me as her cousin from out of town and I guess I was about to blow out I have never and I mean NEVER up to these days NEVER been so happy in my entire life so they proposed to hang out with us and this guy was with hitting on me that I was like in cloud 9 I couldn’t do anything or say anything I just smiled at him, wave my head and there was a park my aunt said she was going to sit and said that I could walk with Sam so we started walking to the park and I was totally out of this world that was awesome because I dressed a lot of times but I was always at home the touch of my legs in the outside feeling those silk stocking and a dress hitting the wind there is nothing that could make me feel better than that since I was 13 my voice was like a kids voice but my aunt told him that I was 17 so everything was perfect it was a perfect night but as always all dreams have to end he was a gentleman so they took us to the car and he kissed me on the cheek so we hug and said goodbye… when we where going back to the house she asked me since when I started doing this and asked me how did I feel dressed and everything she was very surprised since I managed the hi heels like an expert so we went to her place but her husband was not there so she said to wait in the car, when she came back she got a package and gave it to me, it was some nice lingerie from the bridal collection and gave me a chemise to sleep with it and she said to be ready tomorrow so we could go to church dressed when we got home, she picked what I was going to wear the next day for church she was exited to see me so happy so when I went to church the next day the dream ended because when I saw my Mom and Dad I was dressed and with makeup and I remember that I even jumped in front of them saying HI!!! and they stared at me, at first they smiled because they didn’t recognize me but when my dad recognized me he hit me with his fist and I went down to the floor and I woke up in a bed with my mom rubbing my face to take the makeup off my dad yelling to my aunt and then at me he told me a lot of things but what I can remember most is that he said ” your uncle Balt might have queer sons but non of mine will be, I will kill him do you understand?” I was so afraid, it was a disaster but he might taken that Sunday off from me but that Saturday has been the best day of my life
I’m so happy for you that you had such a fun time with your aunt, but I am truly sorry about your father… I hope that you’re okay, and I hope he comes around, and learns to accept you for who you are. I wish you all the best of luck.
I am sorry to hear about your dad, I am glad you had such a great time with your aunt. I wish I could have that with my aunt.
Christina, I am sorry to hear of your life, I am glad that you did not jump out of the window. I don’t see why having only one leg would stop you from dressing up. If nothing else get a bag and do what I do, dress up at the game store while I am working on my writing. you might not write but there are always places that we can be who we really are.
Love
Chantel
Thanks Chantel…it’s hard for me to loose the valor to turn the other cheek and tell my father that I felt much better as a woman rather than a man the only thing is that my family was a very conservative and all this happened in Mexico so you know how MACHO’S we supposed to be so all I did was cope with the idea that I have to be a man but now that I have grown I lost my first marriage because she caught me with her clothes and makeup so when my parents knew why she wanted to divorce me, they made a big deal out of it sent me to a shrink and was intern in a cockoo’s nest on those days, still was not very disclosed about the Harry Benjamin HBIGDA so the shrink said to him that I was a woman but for my sake I needed to be what my dad had conceived A MAN so my dad kept saying to “fix” me so in order to leave the cockoo’s nest. They found me a wife I didn’t want to have children but we had one almost 5 years later no sex life maybe once every 3 months I mean a very dull life now that I live here in the US but married and had a girl at a very grown age I gave up, 3 years later I lost a leg in an accident and couldn’t dress anymore so everything went wrong and now here I am watching beautiful TG woman and I remained as a “WANNABE” and I can understand you since I am in the same boat as you I wanted so bad to repeat that day every single day in my life go thru all those sacrifices that we need to do to get our breasts and vagina and have a very colorful closet with a lot of dresses and heels and purses with all those fine and silky fabrics and all the hairdos you can do and you play with colors in your hair… 5 months ago, I was going to end jumping from this hotel 12th floor balcony but I couldn’t leave my little princess but really If I had another chance to do it all again, I really wish so, I could do things right but that happens only in Fairy tales not in real life so I have to finish what I started (I hope it ends soon) and maybe in another life…
The first time I went out in public was Halloween 1983. I got dressed up and a girl help me put on make up and went to a party at a local bar which the bar maid did not know I was not what I appeared. I would go to a lake on weekend as a woman and never had any problems.