My first time dressed in public.

To walk the streets freely amongst people whilst dressed as a woman is the Holy Grail for most crossdressers. It’s a chance to revel in that wonderful invigorating feeling of freedom and hear the small voice in the back of your head saying, “If only they knew!”

I’ve been crossdressing much of my adult life, but in private. As the years have gone by the urge to step out has grown but I’ve always held back.

Until about 14 months ago.

Generally, I’m pleased with how I look when dressed. I’m lucky in that I’m not overly tall (about 5’-9”) and I’m slim (at just over 10 stones) so women’s clothes hang fairly well on me. But makeup has always been a problem; try as I might (and I have tried, believe me) I can never do my makeup convincingly, and that has always held me back when it comes to venturing out.

When my wife went away for a for few days I did something on an impulse I’ve always wanted to do. I booked a three-hour session with a crossdressing service in a town about an hour’s drive from where I live.

It was a wonderful afternoon spent in the company of a lively, chatty, and understanding woman, who had no issues or hang-ups about crossdressing and who had a wardrobe of beautiful clothes to put at my disposal. The best part was that her spending an hour to give me a professional makeover. At the end of which, when I looked in the mirror, left me ecstatic. I hardly recognised myself. Where my attempts at makeup had always been ham-fisted and unconvincing, she succeeded in turning me into something that was really rather gorgeous!

My original plan had been to wash everything off and revert to my male clothes for the journey home (after taking dozens of photos of course!) I couldn’t bear to do so. I made the decision to stay en femme. I had fortunately brought a selection of my own feminine clothes with me, so this wasn’t a problem.

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I put on a dress, some tan hold-up stockings, knee-length boots with a small heel (which were easy to walk and drive in) and dark grey coat and scarf. I felt wonderfully feminine but at the same time not in the least outrageous or tarty. Nothing that would draw attention to myself.

About a 30 minute drive away was a smallish town and I decided to park there on the way home and see if I felt brave enough to venture out of the car. Even driving there felt deliciously daring and just a little wicked.

I parked up in fairly quiet car park I knew of. It was late afternoon in early October, so it wasn’t exactly dark yet, but the light was fading, and it was chilly. Me in a coat and scarf would be perfectly normal.

I must have sat in the car for 15 minutes or so, just plucking up the courage to walk to the ticket machine and buy a ticket! It sounds silly but this was a huge step for me, and my heart was pounding. Eventually, I stepped out of the car, enjoying the feel of a cool breeze blowing against my stockinged legs and walked – slowly – to the machine. I popped a pound in, and then back to the safety of the car. I’d done it! And it felt amazing.

After another five minutes or so of sitting in the car I decided that this sitting around was ridiculous, I had to get out there. I locked the car and began to walk towards the main street and the shops. I’d read previously about the important things to remember when “going public” such as walking like a woman with smaller steps, don’t rush, keep your head up, and look confident.

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As I walked a couple came towards me. I almost turned on my heel and fled but I carried on and we passed each other. I expected them to stare or snigger, but they didn’t bat an eyelid. I was simply a woman heading for a spot of late shopping. It felt glorious. Once on the main street there were many more people but by then my confidence had grown. I window shopped, I checked my phone, I strolled about, and I began to seek out other people just to walk past for the sheer thrill of it.

Crossdressers who have done this know exactly how I felt. You never forget your first public appearance. For those who haven’t yet done it, all I can say is that it was the most liberating, wonderful feeling ever.

I toyed with idea of going into one of the shops and buying something but chickened out as it would mean having to speak and I felt that would give me away. Looking back now, I regret that decision because I honestly don’t think anyone would have cared even if I had been clocked as a man.

Eventually, I drug myself back to the car and drove the rest of the way home. I spent all evening en femme, enjoying the look and feel of the makeup. Before bedtime I stepped into the shower and Jemma, almost literally disappeared down the plug hole.

What did I learn from my experience? I definitely want to do it again! Covid and lockdowns have made it impossible for now, but once things return to normal, I’ll be booking another visit ahead of having another stroll in the great outdoors. I’ve also decided I must become more adept at applying my own makeup. Once I can do it proficiently, it will open the doors for many more outdoor adventures.

I can’t wait.

 

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MelanieElizabeth
Member
2 months ago

Great story Jemma. So motivational! You were at the height of confidence after your makeover and you took advantage. So happy for you.

Sandy Jayson
Duchess
Active Member
2 months ago

Jemma, it is articles like this that helped me on my first outing in public. After reading stories like yours since joining CDH, I decided it was time for me to take the the next step. My birthday was early Sept. , so for a present to myself I decided to get my hair colored ( enough to color the gray). Because of the covid my hair was at that time nearly shoulder length. I called an Ulta store to make an appt. and told them at the time I was a cross dresser. On the day of the appt.… Read more »

Sandy Jayson
Duchess
Active Member
1 month ago
Reply to  Jemma Jones

Jemma, it just takes a little time and reading all the stories here on CDH. After reading soooo many others and their successes.and some times their failures I just worked up the courage and just said to myself what the he**, and just did it.
Sandy

Leonara
Ambassador
Active Member
1 month ago

Three inspirational experiences for stepping out for the first time… Lovely ladies, thank you for sharing…. as soon as the COVID restrictions are lifted… Leonara will be out and about for the first time too..

Natalie Elizabeth
Active Member
1 month ago

Jemma,
Thank you for sharing such an inspiring experience! It sounds like you had a wonderful day and showed the world your fabulous self.

Amy Myers
Baroness
Noble Member
1 month ago

Thank you for sharing that wonderful experience with us. I have been out a number of times, too many to count now, but that first mall trip for me was like you described. I sat in my car nearly afraid to get out! But I did it. So very scary, but wonderful and very addictive. Also, one of the best things I did for my presentation was book an hour long makeover at Mac Cosmetics. She was great and taught me a lot about makeup. I did intend to go back some months later, but we all know what has… Read more »

Samantha Moore
1 month ago

Lovely story Jemma……thank you.

Jasmine Honey
1 month ago

Honey that’s a beautiful story, I’m so happy for you. I can only dream of such a day unfortunately.
Lots of love and kisses Jasmine x x d

Jasmine Honey
1 month ago
Reply to  Jemma Jones

Due to being in the closet , as my wife doesn’t approve and won’t support me.

Valerie Knox
Baroness
Member
1 month ago

Love your story Jenna. I only dress in private now but your story gives me confidence that one day I’ll be able to go public. I shop for women’s clothes as a man so I think maybe I’ll be able to venture out as a woman someday. Thanks for your story.

Stephanie Kennedy
Princess
Active Member
1 month ago

Hi Jemma Enjoyed reading your story. I am happy for you. Its so nice to read that so many of us are getting the girl out of our head and showing how we really feel
Stephanie

Dani Grand
Member
1 month ago

That’s an awesome story! Keep at it! ❤️

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