Glamorous Times

On the night of the winter solstice in 2014, there was to be a parade of lanterns from the town centre and along the seafront, followed by a bonfire on the beach, and fireworks.  I decided to go along cross-dressed, not in a fancy costume, but in something respectable.  So I chose a grey jacket and skirt, black opaque tights and my chunky pink Mary-Jane shoes.  With a long coat and a hat, I felt snug and secure as I stepped into the winter night.

Blending with the crowds, I followed the fiery torches and watched the fireworks from a seafront bench, away from the main throng.  Then I wandered further to a nearby bar, daring to enter for a drink – a half pint of ale, which I often have when cross-dressed.  A pint looks a bit excessive!  Someone asked what it was, I said it was nice and I think they bought the same.  Someone else said I looked stylish.

Heading home, I saw a figure wandering towards me.  It was an old man, in a state of confusion, who asked where he could buy some slippers.  Given that this was late at night in a residential area, the request was both strange and impossible to satisfy.  Concerned, I decided to see him home.

The old man lived nearby, though he barely recognized his front door.  I asked him to try the key and thank goodness, it opened!  I went inside, seeing him upstairs into his flat.  Relieved, I stayed for a chat.  The man clearly had some kind of dementia, though his brain was clear at times.  He said he had been a press photographer, and there were fine prints on the wall of foreign locales.  I advised him to have a cup of tea and get some well-needed rest.

Not once did the man question my looks or the truth of my femininity.  In his eyes, he had been helped home by a well-dressed, concerned woman.  Thinking back, would I have dressed that way if I had known the incident would occur?  Perhaps not – though I was proud to have dealt with a crisis and kept, at all times, in character as ‘Polly Jocelyn’.

As I drifted away from Brighton’s Pride events, a smaller version called Trans Pride had begun.  This offered a calmer experience for anyone who identified as ‘trans’ in any of its myriad forms, although it was not particularly aimed at cross-dressers.

The first couple were modest occasions, with just a few stalls on a grassed area, but it began to grow in size.  One year, I went as a man during the day, speaking to one of the stallholders – a transgender woman called Natasha, whom I knew from a trans group that I attended occasionally.  Feeling dull at my own presentation, I arrived at the evening disco rather better prepared.  This was held at an arts club, once a venue called The Harlequinade, in an unfashionable back-street.

“Just look at you now!” said Natasha, as I bopped around in the black & white dress bought in 2011.  It became stained with spilt beer, sadly – a worthy ‘battle scar’.

I threw myself fully into Trans Pride in 2017, wearing a short lace dress and chunky heels by day.  It was good to meet my old cross-dressing friend Sam, an infrequent but welcome occurrence.  The event was held with the misplaced optimism that characterises the English summer.  Alas, the rain started to pour and a gale-force wind whipped around the tents.  One gazebo was literally raised off the ground.  We retreated to Sam’s hotel, having a long chat about cross-dressing over cups of tea.

I popped home before the evening event, though this was held in a hyper-crowded bar and was no fun at all.  I spent the whole time jammed up against a wall, and ended up minding coats.  I never even reached the dance floor and missed Sam entirely.  Luckily, there was a chill-out session at another pub next day, where we were able to meet again.  One of Sam’s friends, another cross-dresser, said how they had come by train.  They had an ‘A’ plan and ‘B’ plan for getting back safely, very sound advice.

Next year, 2018, I donned my blonde wig again for an event called Traumfrau.  One of a series of club nights in different venues, it was held in an old church that was now a centre for the arts.  I wore a pink blouse with a short black dress, carrying a small velvet shoulder bag.  I also had small-mesh fishnet tights layered over grey opaques, with four-inch black stiletto heels.

The venue was wonderfully Gothic, though the girls running the show yelled into a microphone in what was already an echoing venue, making for an ear-piercing time.  Still, I had a nice chat with a trans girl from America and a bit of a dance, before slipping quietly away.

Wanting to round out the evening, I lolled on some white sheets at home, and snapped myself in my glamorous outfit.  Indeed, these were some of my best-ever girl-self portraits.

Around Midsummer, a friend was having a birthday picnic in some ornamental gardens in a country village.  Taking the bus there, I arrived in a purple pencil skirt and white blouse, with opaque grey tights and chunky heels. A pink hat completed the ensemble, as I was determined to cross-dress despite a heat wave that had dried the grass to dust.  Though she had not known of my other self, my friend accepted it perfectly.  One of her other guests was a transgender woman, in any case.

On the way home, an unexpected gust of wind whipped the hat from my head.  I groaned as it flew into the private gardens of a smart apartment building.  There was no way I could climb over the fence in a pencil skirt.  Would I have to return as a male and risk it in jeans?  Wandering along, though, I found an open gate and decided on the civilized approach.  I simply walked in and picked up my hat.  Then my eyes met those of an observer, enjoying the sun from his back door. 

What could I say?  “Had to get my hat!”, I chirped.  He smiled, not suspecting the true nature of this glamorous trespasser.

That was almost it, as I had a large art commission to work on that summer and I was already behind schedule.  ‘Polly’ would have to rest for a while, but first I needed to have my fill.  So I dolled up the next day too, went wandering round town in a ra-ra skirt, and loved every minute. 

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Polly Jocelyn

Have been cross-dressing for over twenty years. I particularly like female office attire, fairy tale dresses and gothic looks.

Latest posts by Polly Jocelyn (see all)

• As the Days Unfold - June 13, 2025
• Sublime Sensations - May 17, 2025
• The Feeling Returns - February 28, 2025
• Glamorous Times - January 11, 2025
• Dressed Till Dawn - December 6, 2024

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