Dressing Up, Girlis...
 
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Dressing Up, Girlish

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Posts: 35
Lady
Topic starter
(@polly)
Trusted Member     Brighton, East Sussex, United Kingdom
Joined: 4 years ago
wpf-cross-image

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.

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...”

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.

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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49 Replies
10 Replies
(@caroline2k)
Joined: 1 year ago

Honorable Member     Tyne and Wear, United Kingdom
Posts: 344

@polly 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 🙂

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Lady
(@polly)
Joined: 4 years ago

Trusted Member     Brighton, East Sussex, United Kingdom
Posts: 35

Thanks, Caroline, I appreciate what might well have been your sensible restraint. I will touch on my more disempowered times in a later piece. Appreciate 'fabulous' - writing an article is, oddly, a detached way of being a CD and reflecting on it.

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Lady
(@kimdl94)
Joined: 1 month ago

Estimable Member     Longview, Texas, United States of America
Posts: 47

@polly 

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

 

Kim

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Lady
(@polly)
Joined: 4 years ago

Trusted Member     Brighton, East Sussex, United Kingdom
Posts: 35

Thanks, Kim. Yes, balance is a kind of skill but could seem a dull aspiration if one really wants to let rip. I will cover this in a later piece.

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Lady
(@kimdl94)
Joined: 1 month ago

Estimable Member     Longview, Texas, United States of America
Posts: 47

I look forward to how you might let it rip!

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Lady
(@polly)
Joined: 4 years ago

Trusted Member     Brighton, East Sussex, United Kingdom
Posts: 35

Hope not literally, as I did catch a jacket pocket on a door handle the other day!

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Baroness
(@annaredhead)
Joined: 3 months ago

Honorable Member     Cornwall, United Kingdom
Posts: 304

@polly 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.

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Lady
(@polly)
Joined: 4 years ago

Trusted Member     Brighton, East Sussex, United Kingdom
Posts: 35

Thanks, Anna. Sometimes Brighton is so full of novelty, though, that more subtle experiences are drowned out. That is why I no longer bother with Pride, and will cover this in a later piece. Charity shops are aplenty here, great for stylish & vintage apparel.

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Lady
(@candycross)
Joined: 1 month ago

Estimable Member     Queensland, Australia
Posts: 127

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

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Lady
(@polly)
Joined: 4 years ago

Trusted Member     Brighton, East Sussex, United Kingdom
Posts: 35

Great your wife can help!

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Posts: 127
Lady
(@candycross)
Estimable Member     Queensland, Australia
Joined: 1 month ago

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

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3 Replies
Lady
(@polly)
Joined: 4 years ago

Trusted Member     Brighton, East Sussex, United Kingdom
Posts: 35

Thanks, Jane. This was my thought in telling the story this way, building up from early attempts into a reasonably blossoming babe.

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Lady
(@candycross)
Joined: 1 month ago

Estimable Member     Queensland, Australia
Posts: 127

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

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Lady
(@polly)
Joined: 4 years ago

Trusted Member     Brighton, East Sussex, United Kingdom
Posts: 35

There's no pressure, do what feels safe and right for you.

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Posts: 208
Duchess
(@juliarey)
Honorable Member     Somewhere between Milwaukee and Green Bay, Wisconsin, United States of America
Joined: 2 years ago

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

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1 Reply
Lady
(@polly)
Joined: 4 years ago

Trusted Member     Brighton, East Sussex, United Kingdom
Posts: 35

Thanks, Julia. Twenty shops but not all clothes shops - looked at books too, and didn't buy much from what I recall.

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Posts: 2652
Hostess
(@ab123)
Famed Member     Surrey, United Kingdom
Joined: 4 years 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.

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1 Reply
Lady
(@polly)
Joined: 4 years ago

Trusted Member     Brighton, East Sussex, United Kingdom
Posts: 35

Thanks, Angela. I have more recent stories to tell and will upload more articles in due course - some trivial, some deeper.

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Posts: 18
(@cornish-coffee)
Eminent Member     Cornwall, United Kingdom
Joined: 6 years 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 🙂

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5 Replies
Baroness
(@annaredhead)
Joined: 3 months ago

Honorable Member     Cornwall, United Kingdom
Posts: 304

@cornish-coffee I've been very tempted to walk round Brighton en femme. Not quite "there" yet.

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Lady
(@polly)
Joined: 4 years ago

Trusted Member     Brighton, East Sussex, United Kingdom
Posts: 35

Thanks, Anna. You do see quite a few cross-dressers, or perhaps transgender individuals, around Brighton so I don't think it is too bad even if you don't look perfect. But always best to do what is safe and comfortable for you. Even I get my nerves jangled after yonks of experience.

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Baroness
(@annaredhead)
Joined: 3 months ago

Honorable Member     Cornwall, United Kingdom
Posts: 304

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

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(@christineth)
Joined: 2 years ago

Prominent Member     Brussels, Brabant, Belgium
Posts: 534

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

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Lady
(@polly)
Joined: 4 years ago

Trusted Member     Brighton, East Sussex, United Kingdom
Posts: 35

Thanks, June. I'm only 5'4" so can get away with 4" heels and not look too large! Though of course, if clothing was freer in its choices for males, you would not need to pass.

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Posts: 262
Guest
(@Anonymous 95235)
Reputable Member
Joined: 4 months 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

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3 Replies
Lady
(@polly)
Joined: 4 years ago

Trusted Member     Brighton, East Sussex, United Kingdom
Posts: 35

Thanks, Samantha. I had a day out in London fully cross-dressed last year for the first time, and will relate this in a later article.

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Guest
(@Anonymous 95235)
Joined: 4 months ago

Reputable Member
Posts: 262

@polly will look.forward

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Lady
(@polly)
Joined: 4 years ago

Trusted Member     Brighton, East Sussex, United Kingdom
Posts: 35

I will tell some more memories before that, so they run in chronological order.

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Posts: 9
Lady
(@nataliegay)
Active Member     Tampa Bay area, Florida, United States of America
Joined: 8 months 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.

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2 Replies
Lady
(@polly)
Joined: 4 years ago

Trusted Member     Brighton, East Sussex, United Kingdom
Posts: 35

Thanks, Natalie - wow, purged the guy stuff! I have had thoughts like that but need to be a guy as well for family and work reasons (so I say to myself, anyway). I once considered moving to a new town and going girl full time, an unrealized fiction so far.

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Lady
(@nataliegay)
Joined: 8 months ago

Active Member     Tampa Bay area, Florida, United States of America
Posts: 9

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.

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Posts: 262
Guest
(@Anonymous 95235)
Reputable Member
Joined: 4 months ago

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

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Posts: 20
Lady
(@kimmiejo)
Eminent Member     Jackson, Tennessee, United States of America
Joined: 5 months 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 wife to be the winner and we set her straight and she asked what I was reused as and where I sat. After telling her I was the red headed witch sitting near the food tables she said no way that was you?

I am so looking forward to next weekend as my wife is taking me to a dinner show west of Chicago. It is quite a drive from Memphis but will be fun. I bought three new outfits for the three days and on Fabulous dress for the dinner show. My wife bought me a new bathing suit for the hot tub in the hotel. I wish one of y’all’s events would coincide with my wife’s schedule so we could attend and meet y’all. I’d really love to go on a en femme cruise and my wife would be down as she loves to cruise.

y’all keep smiling and making memories.

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1 Reply
Lady
(@polly)
Joined: 4 years ago

Trusted Member     Brighton, East Sussex, United Kingdom
Posts: 35

Thanks, Kimmie, Halloween can make some great memories. I will do a separate article about some Halloween experiences, though it is not such a big thing in the UK. Joyful that you won a contest!

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Posts: 370
Lady
(@vecca)
Reputable Member     Arizona, United States of America
Joined: 3 years 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.

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1 Reply
Lady
(@polly)
Joined: 4 years ago

Trusted Member     Brighton, East Sussex, United Kingdom
Posts: 35

Thanks, Vecca - none of this mini-biography was known to me as it happened, it's just the way it unfolded. And I've compressed 20 years into 1000 words or so, though will do an update or two soon...

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Posts: 539
Baroness Annual
(@delaware)
Honorable Member     los angeles, ca, United States of America
Joined: 7 years ago

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

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1 Reply
Lady
(@polly)
Joined: 4 years ago

Trusted Member     Brighton, East Sussex, United Kingdom
Posts: 35

Thanks, Karley - my wayward adventures rather than any great navigation!

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Posts: 1370
Hostess
(@cdsue)
Noble Member     Delaware, United States of America
Joined: 4 years 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.

XOXO
Suzanne

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1 Reply
Lady
(@polly)
Joined: 4 years ago

Trusted Member     Brighton, East Sussex, United Kingdom
Posts: 35

Thanks, Suzanne - we all do what we can or want, there was a lot of fear and trepidation before the empowered moments I tell here.

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Posts: 4
(@twinkieb)
Active Member     Raleigh, North Carolina, United States of America
Joined: 2 years 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 interested in men! But I also enjoy my "alter-ego" who is quite the macho guy. I can look attractive I have been told but I am 2m tall which makes it impossible to "pass" or I would dress more often. My wife knows both sides and actually has learned to appreciate both and is supportive which always is a plus. I am curious, I see no mention of a significant other from you. Do you ever have a desire for that kind of companionship? GOD BLESS girl! Enjoy life...

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1 Reply
Lady
(@polly)
Joined: 4 years ago

Trusted Member     Brighton, East Sussex, United Kingdom
Posts: 35

Thanks, Twinkie yes, DRAG is really an acronym for 'dressed as girl' though is often used to refer to exaggerated performance styles, not really my thing though they can be amazing. I think a lot of the release one feels when CD'ing is actually finding a spiritual side, so the gender thing might not really be such a literal element. I think few girls I am close to have known about Polly, to be honest - she seems to occupy a separate niche.

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Posts: 35
Lady
Topic starter
(@polly)
Trusted Member     Brighton, East Sussex, United Kingdom
Joined: 4 years ago

Thanks for all your great feedback. More articles in preparation!

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Posts: 262
Guest
(@Anonymous 95235)
Reputable Member
Joined: 4 months ago

Thanks for sharing! You are beautiful!

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1 Reply
Lady
(@polly)
Joined: 4 years ago

Trusted Member     Brighton, East Sussex, United Kingdom
Posts: 35

Thanks! Have more articles in the works, with images too.

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