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.

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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…”

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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.

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Kimmie TNLady
1 month ago

Congratulations Polly. I like your style now. You look great. went through that phase in my 20s and 30s showing lots of leg in those mini skirts. But I was the only one admiring my legs LOL! I do go out more often starting about ten years ago when my wife and I went to a charity Halloween party. I didn’t know there was going to be a secret contest and I was actually selected as best female. What a lift to my ego. I won an in home massage. When the masseuse came to our house she expected my… Read more »

Vecca Senn
1 month ago

For me, it’s a personal thing. It doesn’t meant I wouldn’t enjoy an accepting public outing, but this side of me is meant for me, my wife, and very select friends and family. This is MY time. MY expression. MY other side. It is a completely selfish journey that I am glad I only reveal to those I deem worthy. But,,,, You’re right, there is a certain draw to a public acceptance, or even better, an admiring passerby.

karley delaware
Active Member
1 month ago

Hi Polly, Thank You for sharing stories from your journey.  karley

Suzanne Martin
Active Member
1 month ago

Polly –
Thank you for sharing your story I am not at the point of wandering out of the house although I think it would be nice to do. I am content with what I am able to do now. Who knows what the future holds.

Twinkie Brashear
1 month ago

Polly! I always find it so thrilling to ‘go out’ on my own as Twinkie. And yet, afterwards it is a ‘relief’ if you will, when I return and become my male self. I love the way you speak of your respect for “a sense of balance". I totally agree, as it does bring balance to what I can only think of as my “alpha" side. I had always heard that the clothes make the person, or words to that effect, and I have found that to be quite true. When DRAG, I find I am quite passive and seem… Read more »

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Becky Acosta
1 month ago

Thanks for sharing! You are beautiful!

Jenna Monroe
1 month ago

Thanks for the story. Very helpful. You make a great femme. I’ve been retired for awhile and I am able to dress femme most of the time. I keep my self hairless and toes and nails painted. Learning makeup now. Finally have a decent wig. I live in an apartment and have invited neighbour lady in for tea. She has glimpsed me dresssed en femme so I thought I would come out to her. Was actually lovely. She was most accepting of my femme side. She described it as a fetish. I told her the story of how I got… Read more »

Donna O Lacey
30 days ago

What a lovely story. I too love to wear lovely ladies clothes and shoes and makeup etc but unfortunately I don’t have your courage. I hope your lovely article will encourage me and give me the confidence to go “out". Like you Polly Jocelyn I also want to keep my personality and my identity in balance but I think you will agree with me when I say,once you have disclosed your passion for crossdressing then you will be seen as a crossdresser and nothing else. I am a divorced father of 2 sons and I am grandfather of a beautiful… Read more »

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