It’s a thrill for me to dress in women’s clothing. I’m not a drag queen, as I don’t generally perform, or exaggerate the look for effect. I just like wearing my clothing in a glamorous, stylish, or pretty way. I restrained the urge a lot in my 20s, occupied by artistic projects and the green movement. But in the mid-1990s, the urges were let loose!

I owned few female clothes before that. I bought my first pair of stilettos in 1989, meekly purchasing them as a male in the guise of Christmas shopping. Annoyingly, they were half a size too small. I later acquired a black woollen skirt and Basque with suspenders – both quality items I still wear decades on, along with a pair of cute pink Mary-Jane shoes. I remember the delight of donning stockings and suspenders in my first bedsit and gazing at my mirrored reflection. However, I had no other female items of dress so I made do with male shirts and jackets when putting an outfit together.

It’s one thing to dress up at home, spending hours looking sultry in the mirror. Going out is a real test and a serious commitment. Years of bedsits and shared houses offered limited freedom. However, moving to a self-contained flat in late 1995, on the edge of a country village, at a time when I was already wishing to cross-dress more offered more opportunities. By then, I had bought a long flowery dress that I loved, along with a red velvet jacket from Camden Market in London. These made a cute outfit with the pink shoes.

I also visited a bargain store selling three items for £5, purchasing a black cocktail dress, pinafore, and blue jacket, plus a red dress in crushed velvet for £7. “Confused?” asked the assistant as I juggled the items at the till, as a male, though I was unsure of his exact meaning. Did he think I was struggling to choose or that I had an identity crisis? But there was no confusion in my head – I wanted to wear them.

Herbal_breast_enlargement_naturedaycom (1)

One winter night, I decided to risk a walk through the village in the cutest combination I could muster. I donned the flowery dress and pink shoes, white woollen tights and red velvet jacket. I frizzed up my hair, and put on make-up plus a broad woman’s hat. I looked incredibly vintage and twee, which made it all the more exciting.

Moving through the night, I passed a cash machine where a teenage lad gazed upon me, then turned to speak to his friend. What would he say? Something derogatory or abusive? I kept on without batting an eyelid but heard some thrilling words.

“There’s the girl for you, mate. She’s gorgeous!”

No irony, he believed it and meant it. I was glowing inside.

In the spring, I could no longer hold back in terms of visible cross-dressing. I had always made short, night-time trips round the block – but I wanted far, far more. I had to feel that sunlight on the back of my nylons. Resembling an air hostess in the blue jacket, cocktail dress, and hat I hovered on the threshold and dared myself to go out. Whenever I approached the door, I quaked in fear until I finally stepped into the sun.

Perhaps living in a village was not ideal for this kind of thing. But it was great walking as a posh woman down to the village green. I sat on the grass in ecstasy. I heard the words of a man, “Excuse me, love…”

EnFemme

The guy asked for directions to a nearby garden, which I squeaked out in a girlish way. He thanked me, unfazed. I’d gotten away with it! My heart beat vividly with another barrier broken. It was hard to deal with the giddy knowledge that I could pass as a girl!

Thus began a typical pattern: waiting till the urge could no longer be denied, then overcoming sheer terror and going out. Sometimes, my looks were a bit dodgy as I practiced my craft. At best, I was highly convincing. Even so, I worried my actions would become compulsive and kept my cross-dressing on a fairly tight lead – perhaps tighter, in truth, than was fair given the joy it brought me.

Three years later, I had a flat in town. A similar rebirth happened one sunny day, in January 1999, when I marched to the local shops as a woman. I had seen some gorgeous high-heeled shoes for sale previously. I timidly entered, my dry throat affecting a ‘female’ voice. At the time, I found it hard to keep it consistently high-pitched and convincing. As shop assistants deal with all sorts they did not appear ruffled. Maybe I passed okay, or they had a giggle afterwards. I also bought a charity shop skirt for a pound and was so pleased back home that I pushed myself further. I wore the clothes around town all afternoon, visiting over twenty shops!

Later that year, a female friend met me by chance and invited me to a Christmas Eve party at her shared house. “Come as smart as you like,” she said, not knowing of my cross-dressing. I thought, what a chance – and arrived in a very gothic black velvet dress. It was a real hit, and the lady was inspired to hold a drag-themed party when she left the house.

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I also had a blonde wig and a lovely Alice in Wonderland dress purchased years before but never worn socially. I love the look of Alice, and delight in portraying an adult version at various parties – along with appearances in my gothic dress!

I use the name ‘Polly’ when dressing this way, with the middle name ‘Jocelyn,’ which makes it easier to identify myself. I’ve gotten used to it in that it equals my real, male name in grabbing my attention. Before, I’d had odd moments when I’d been chatted up or asked questions and not even had a female name in mind. It was like the old TV programme Quantum Leap, suddenly being thrust into a different body or persona of which one knows nothing.

I had always avoided Pride despite living near one of the bigger events, Brighton in the UK, but eventually thought – “What the hell?” I attended in girly gear in 2001, in my gothic dress. I met a nice cross-dresser from London in 2002, who recognized me two years later in my ‘Alice’ gear. He even called me Polly! I was photographed a dozen times, often with a grinning stranger. It’s fun to think of those scattered images in various snapshot collections. Then a local rap artist, a girl with dreadlocks, dragged me to a bonfire on the beach like a trophy doll. It was fun – but I was alarmed when a charming man with a big moustache kissed me on the nose. Did I want company for the night? Polly slipped away around four in the morning, thus eluding him!

I took it as a compliment. As a creative person, I’d hate to go out as a girl looking anything but enticing. Polly, though, was an honest lass. I wasn’t looking for a boyfriend, and couldn’t lead him on.

So there’s a quick spin through my girlish escapades. I’ve enjoyed each one, and generally the more confident I’ve been, the more the “Missions” have been successful. A guy at a Halloween party in 1998 said, “You look ravishing.” At the drag-themed party in the shared house, a cartoonist friend said, “You were born to be a woman.”

The most amazing stuff said to me was at a party when a girl looked deep into my soul. “You’re androgynous,” she said. “You’re feminine, but not effeminate. You’ve got a very young spirit. It’s the real you coming through.”

I’ve often felt cross-dressing helps me push on with more manly tasks. When the make-up’s washed off and the dresses put away, at least I’ve had the thrill and know what I’m capable of. I know I would like to do it more, or even all the time. But I respect a sense of balance.

EnFemme

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Caroline Davidson
Lady
Active Member
1 month ago

@Polly Jocelyn I can so relate to so many aspects of your story Polly, thank you for sharing 🙂
I really wish I’d had your nerve, and grasp the nettle more than I did when I was younger, and not spend so much time skulking in the closet. Oh well 🙂
You look fabulous by the way 🙂

Kim Hanson
Lady
Active Member
1 month ago

@polly 
I enjoyed reading about your emergence.  Also glad you have managed to find a comfortable balance.
 
Kim

Kim Hanson
Lady
Active Member
1 month ago
Reply to  Polly Jocelyn

I look forward to how you might let it rip!

Jane Millane
Lady
Active Member
1 month ago

I enjoyed your story it helps others who are not yet out of the closet

Jane Millane
Lady
Active Member
1 month ago
Reply to  Polly Jocelyn

I want to eventually go out , however l am currently building up on my wardrobe and hope to purchase a breast form soon and also the courage

Julia Reynolds
Duchess
Active Member
1 month ago

You look beautiful, I can tell you’re well practiced. Loved the story, 20 shops in one day?

Anna Redhead
Baroness
Trusted Member
1 month ago

@Polly Jocelyn a very enjoyable and interesting read. I lived in Sussex for many years and worked for a time in Brighton. It is a great place to be yourself and good to hear that you were able to embrace that. I do love shopping round Brighton and was there a couple of months ago and came away with a good haul of treats for Anna. You look great in your photo.

Jane Millane
Lady
Active Member
1 month ago
Reply to  Anna Redhead

Thankyou very much, the make-up was done by my wife. She buys all my clothes we go shopping for them together

Angela Booth
Member
Trusted Member
1 month ago

It’s a nerve jangling time when you finally succumb to the desire to dress and move outdoors. Once done there is that elation being incognito among the public and being accepted as the woman you are. Thankyou for the wonderful success story.

June Richards Jewell
Lady
Member
1 month ago

That was a good read, Polly. You come across as happy in yourself. I wish that attitudes had been different in the 1970s, I’d have been down to Brighton in my skirt, top and tights, no doubt. Been too tall to ‘pass’ since my teens but at least I was slender and not bad-looking back then. All the best 🙂

Anna Redhead
Baroness
Trusted Member
1 month ago

@June Richards Jewell I’ve been very tempted to walk round Brighton en femme. Not quite “there" yet.

Anna Redhead
Baroness
Trusted Member
1 month ago
Reply to  Polly Jocelyn

The issue for me is being over 6 foot before I put a pair of shoes on. I do like wearing heels but being a very tall redhead is never going to blend easily

Christine Thomas
Lady
Trusted Member
1 month ago
Reply to  Anna Redhead

@Anna Redhead Anna, there are quite a few tall redhead fashion models around…so celebrate your height…be a fashion model and be proud!

Samantha Marie
Member
Samantha Marie
1 month ago

Lovely story Polly, I’m.still at the at home stage except for a few walks and a couple of night tube trips when most people are asleep or worse for wear to notice ! As others have said you look amazing!! X

Samantha Marie
Member
Samantha Marie
1 month ago
Reply to  Polly Jocelyn

@Polly Jocelyn will look.forward

Natalie Gay
Lady
Member
1 month ago

You look great in your pic. I wish you all the joy in the world. There’s nothing quite like crossdressing. I love it so much, I’ve done it fulltime for 20 years. I purged all my guy clothes many years ago.

Natalie Gay
Lady
Member
18 days ago
Reply to  Polly Jocelyn

Polly, that’s sort of what I did, I changed careers. Being a nurse was a perfect fit for me as a woman. I was just one of the gals from nursing school on. I wasn’t prepared for some of the loses I incurred, like losing my kids and a brother. Everyone else stood by me. I have at least 2 dozen girlfriends. Only one of them is Trans,and she isn’t much different from the others.

Vera
Member
Vera
1 month ago

Thank you for this wonderful story and I really like your choice of all your dressing .

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