He had Ten Thousand Men

The Duke may have had that many men, but the pub where I worked, of the same name, would only fit a few dozen of them in the front bar, if they were friendly. There was a lot more room over the three floors and the beer garden. We catered to a very wide range of drinkers, from social groups, office after-hours groups, shoppers from along Oxford Street, and tourists drawn in by its eighteenth-century ambience.

I worked there in the evenings to make money to fund my room in a shared flat, a walk away on Princes Street, over an empty shop that nobody seems to want to lease. It’s a good location for me. A five-minute tube ride from Bond Street to Holborn on the Central Line and I’m only a short walk down Kingsway to the London School of Economics, where I’m in the second year of my course. There was an Italian restaurant next door, Indian down the road, and a Starbucks opposite. What more could a student want!

My parents had funded my course, but I needed to fund my living. The LSE accommodation was solidly booked, so I found where I now live through the internet. The other guys in the flat were both at Kings College doing Arts Degrees, so we often get the tube together. We did have a system where they wake me up so that I can head for the LSE, seeing that I’m often out until the early hours.

I grew up in a family that owned a pub. Actually, a few of them. My weekends, as I got old enough, had been spent tidying the bar and public areas, sorting out bottles and preparing bar snacks. The business had been started by my few times great grandfather, who opened a roadside tavern beside the London to Birmingham stagecoach route in seventeen-ninety. As the family grew, into the middle eighteen hundreds, more sites were obtained to give the growing number of sons work.

Nearly every son through the years had a pub to run, but I was different. I had a head for maths, and had five ‘A’ levels, including Maths and Further Maths. It was decided that I would be sent to the LSE to study finance, in order to replace the expensive accountants that the group now used at tax time. For me, I wasn’t sure that I would be able to replace that business, unless the family also funded a full suite of computerised accounting from every site. That would be a problem for the future, though.

Having grown up in a pub and spending a lot of my high-school years pulling pints in the bar in the evenings, I was welcomed at the Duke of York when I applied there. I worked Mondays, Wednesdays and Thursdays from six to closing time, starting on Saturdays and Sundays at four in the afternoon, and the other days I left at ten-thirty to go to my second job,

My second job started at eleven and was in the Tape Nightclub. On the weekends, we were always busy until three-thirty in the morning, so needing my back-up alarm clock on Monday morning. Friday and Saturday were well into the early hours.

One of the perks of working at The Duke was that I was able to get fed with things left over from the previous day, or specials that I could afford. Lunches, during the week, was usually from the LSE café. I didn’t really need to eat cheaply, as I was getting a decent wage from the two venues and a good share of tips from both of them as well. I was trying to build my bank balance, so that I could get a nice car, without going into debt when I graduated. With everything so close, I didn’t need one for the moment.

It was a busy life, with very little time for socialising, although I did get friendly with regulars from both places, with the nightclub crowd being rather more upper class, seeing that it cost a hundred pounds to get past the door. I also made friends among the people I worked with. The Duke was about fifty-fifty, with barmen and waitresses. Tape was about thirty-seventy, with barmen, waiters and hostesses. The girls were all beautiful, friendly, and mainly married. There were a few that would stop for a chat with me when things were quiet, as sitting at the bar was the usual resting place, not that we had many quiet times.

So far, things had worked out well. My first year into Finance had included the compulsory LSE100 course, where I took the ‘How can we Control AI’ option. It was worthwhile, as I expected that it would need AI to do all the finances, seeing that all the pubs bought and sold similar things, and anomalies were perfect fodder for AI reporting. I had worked at the Duke in my first year, only starting at Tape during the summer holidays. My parents didn’t mind that I didn’t go home, as I was learning another facet of hospitality. The flatmates didn’t mind, either, as I was able to keep the flat tidy while they were back home, shooting grouse, or whatever they got up to. They also popped in on the odd weekend to go to the shows.

We got through towards the last part of the year, were on track towards Christmas, and everything was working well. That was until the festive season started to throw up parties. I’d worked through a few at the Duke, last year, but this was the first year for me at Tape.

The Duke was all fairly normal. We put up some tinsel, had a tree and encouraged patrons to leave money or gifts for the Sick Childrens’ Trust in Guildford Street, just a little way away at St. Pancras. We had a Christmas party, with all of us workers decked out in red and green, with bells on our hats. The girls looked really nice, but I thought that I looked like a gnome.

Tape was different. It was, through the year, a place where celebrities and the well-off went to dance to DJs, drink, have fun, and make contacts. It was a haven for TV and film people, music and fashion icons, overseas visitors and touring entertainers. I’d met more big names in my time there than I could ever have imagined. My job was varied. I’d work the various bars and wait on tables, remove empty plates and glasses. You know, the usual watering-hole work. Friday and Saturday nights were the busiest, and we often went through to half-past five, which let me get some sleep the next days before I started at four.

Usually, what I had been wearing at the Duke was good enough, as I always tried to look presentable, but some nights things were different. With the Tuesday themed nights, they usually had a costume for me to wear. I’d been several superheroes, monsters, apes and dead movie stars. We’d gone overboard for Halloween, with all the staff done out as zombies. Some of the sights I’d seen that night gave me bad dreams for days after. Mind you, with what a lot of the girls wore, I had some very nice dreams as well.

Mid-November, I was given a week to prepare myself for a special theme the Tuesday after. One of the local fashion designers had a singing star decked out in one of their designs on a TV spectacular, and it had been snapped up by fans. It was a shift dress, with a lot of sequins, not quite a mini, but close. They wanted to host a celebration night, and a notice went up on the entrance telling the patrons that nobody would be admitted unless they were wearing one of the dresses. It was available in the shops, in a range of colours and sizes, so it was expected to be a glittering affair.

There were a few who were allowed to dress more normally. There wasn’t a size that fitted our bouncers, and the few guys with beards were allowed to wear jackets and pants that the designer had made up, with plenty of sequins, of course. Me, and the rest of the younger men, were told that we’d wear the dress. On the Sunday, I was given a garment bag with a blue dress, underwear, shoes, and a wig to be wearing on Tuesday, when I arrived.

With me going there from the Duke made it difficult, so, on Monday I asked the manager if I could leave a lot earlier on Tuesday. He wanted to know why, so I told him. He laughed and then told me that I could work my Tuesday shift in the dress and be the barmaid for the evening. Now, I have to tell the truth here. I was no stranger to wearing odd outfits. You don’t grow up in a social pub atmosphere without seeing your share of themed nights, including such weird events as Drag Bingo. I had worn sequins and tassels, wigs and masks, bodysuits and bikinis. If that’s what he wanted me to wear, then I’d follow orders. After all my years in hospitality, there was one thing I had lost forever, and that was being embarrassed in fancy dress.

This dress was really fancy, though. Far more professionally made than anything I’d worn before. The garment bag had included everything to transform me from Gene to Jean. There was even a new name-badge to wear, as well as a small bag of cosmetics. When I got home from the LSE, I got into the shower and thoroughly washed and shaved everywhere. I had previous experience in wearing a filled bra and didn’t have a lot to tuck when I pulled up the panties. Tights and heels on, I slid the dress over my head and looked in the mirror.

It fitted me as if I was a genuine girl, making any previous appearance in a dress look as if I had been in drag, and not succeeding. With my usual long hair, I looked almost right. I put the wig on, which blended with my own hair, making it a lot longer. I sat on the bed, with a mirror propped on the chest of drawers, and applied the minimal make-up. Just some rouge, powder, lipstick and work around the eyes.

When I left my room, the others had got home and just stared at me, mouths open.

“What’s the matter, boys. Haven’t you seen someone in a dress before?”

“Not like that, Gene. You’re a stunner!”

“It does look good. It’s for a special event at the club, tonight, and I wouldn’t have had time to change, so I’m the barmaid at the Duke tonight.”

“Save a table for us, we’re going there for dinner.”

“As long as you’re good boys, I’ll shout you a drink. See you there.”

I had a raincoat that I slipped on, with my wallet and Tape ID in one pocket, and the cosmetic bag in the other. I walked along Princes Street, trying to take shorter steps and getting into character. It was, for me, something very new. Yes, I’d worn a lot of costumes in my life, but never in the open air, in full view of ordinary people going about their daily life. The clicking of heels on the pavement was new, the feeling of the late afternoon breeze on my legs was new, the flutter of my hair around my face was new. The wolf-whistle I got from the driver of a taxi in Hanover Square was totally unexpected.

He Marched them up to the top of the Hill

When I arrived at the Duke, I took off the raincoat as I walked in, heading for the staff cloakroom to hang it up.

“Excuse me, miss. You’re not allowed in there, staff only!”

“It’s me, Gene. You’re the one who told me that I had to wear the dress and work as a barmaid tonight.”

“Bloody hell, Gene! You look good. You can do the dining room bar, tonight.”

“Thank you, boss. Just try to make sure that the guys down here keep their eyes to themselves when I go up the spiral staircase.”

“Just another worry to a sweet girl, like yourself. I see that you even have a gender correct name badge. Very professional.”

“That’s so I can be distinguished from all the others at the club. If you go home through Hanover Square, you’ll see the line-up of patrons dressed in something similar for tonights’ event. I’ll hang up my coat and I’ll head for the dining room.”

I hung my coat and took the cosmetic bag with me when I left. I smiled at the guys I knew in the saloon bar, knowing that they didn’t recognise me. As I was going up the spiral stairs, I could hear the hubbub of comments. The boss called out.

“Eyes down Billie.”

“If my missus had legs like that, guv’nor, I wouldn’t be sitting here with a pint in front of me.”

Charlie called out.

“It wouldn’t matter if she did have legs like that, Billie, you wouldn’t be able to do anything about it nowadays.”

As I arrived at the top, I could hear the laughter below. Angie, the main waitress in the dining room, saw me walk in.

“Table for one, miss, or are you waiting for someone.”

“Not you as well, Angie. The guv’nor didn’t recognise me either. I’m Gene, and tonight I’ll be working the bar up here until ten thirty. Then I’m off to the club where there’ll be a few hundred that are all dressed the same. It’s a celebration of that singer wearing a similar dress. Even the blokes have to be in a dress to get through the door. Can you save a table for Grant and Howard, please. They’re coming tonight, because they want to gaze on my exquisite beauty.”

She looked at my badge and grinned.

“All right, Jean. Welcome to the world of womanhood. You’d best use our toilets if you need to go. I’ll let the others know. How was your climb up the stairs?”

“Comments about my legs and Billies’ wife. At least I’ve given some dirty old men a laugh.”

I went behind the bar and checked the glasses and bottles. The taps would have been connected to new kegs in the basement during the day. My bag went under the counter, and I waited for my first customer. The dining room was a good gig, as the bulk of the orders were brought to me in written notes by the waitresses. I just had to fill the glasses and put them all on a tray for them. The only ones that would be at the bar, otherwise, were the fast drinkers and the odd ones who wandered in from the function rooms, looking for something other than the beer, wines, or soft drink supplied.

When Grant and Howard arrived, Angie showed them to the table and took their order. She brought the paper to me.

“They said that it’s your shout.”

“That’s right, as long as they’re good boys. It looks like they’ve had a shower and changed since I left.”

“Did they see you like this?”

“Yes, they were home before I left.”

“That’s your answer, then. They’ve both seen you in a totally new light. You’re not the workaholic guy that you’ve always been, now a good-looking babe. If you never wear a dress again, they’re going to remember this day for a long time, hoping that you walk out of your room looking sexy.”

“That’s a bit fanciful!”

“Look past me. Is Howard looking our way?”

“He is, and he’s looking at your bum, I think.”

“Go along to the end of the bar and pick up a bottle, take a peek and then tell me who he’s looking at.”

I did as she said, and when I looked up, he was looking at me and smiled.

I went back to Angie with the bottle.

“Now, that’s creepy! You’re right. He must be ill or something.”

“Or something, Jean. He looks like a guy in love, or it could be lust, there’s very little between the two looks. Either way, lock your door when you get home in the morning. You would know what a morning glory makes you want to do.”

“I don’t, actually. I’ve heard about it, but I haven’t had to deal with it, yet.”

“No wonder you make such a girl, Jean. Take a tip from me and go and talk to your doctor. Now, give me their drinks and don’t bother to put anything in the till. The guv’nor can wear this one.”

Before my flatmates left, Howard came over and sat on a stool to talk to me as I worked. As Grant was standing with his credit card in his hand, Howard put his glass down.

“What time do you finish at the club, tonight?”

“Three-thirty, why?”

“Because I’m going to set my alarm and come to escort you home.”

“I’ve walked that way four mornings a week for months now.”

“But never in a dress and looking like jailbait.”

“That’s true. What do you want out your chivalrous act.”

“Your company, as you look now, for the time it takes to get to the flat. If you never look like this again, it will be something for me to remember. Don’t get me wrong, I’m not gay, or not much, anyway. It’s just that you captured my heart when I saw you.”

“I’ll give it back to you when we get back to the flat. Thank you for the offer. I didn’t think through what looking like this could bring.”

Grant paid their account, and I gave them a smile as they left. Angie came over with the next drinks order.

“Time for the serious work, Jean. How was loves young dreamer?”

“He said that he’s going to set his alarm to come to the club and escort me home. That’s rather sweet of him, even though I’ve done that trip hundreds of times. He told me that I looked like jailbait.”

“Ha! That’s a new one. I’ll total up the tips and save your share for tomorrow. With how we’ve done, tonight, the guv’nor may want you to be Jean more often.”

“He’ll have to give me a clothing allowance, then.”

“As if, Jean. As if!”

I worked through to just before ten-thirty, going into the toilet with Angie looking out for me, taking my bag with me to touch up my face. She hugged me before I left the dining room and whispered in my ear.

“If all the girls were as good as you, Jean, we would rule the world.”

Then he Marched them down again.

The spiral staircase was not so easy to go down in heels as it was to go up. Especially as I could almost feel the eyes on my legs as I took each step as carefully as I could. It was a full bar and it fell silent as I descended. I waved to the boss and went to get my coat. Putting it on and putting my bag in the pocket, I walked through the crowd to the door, with several asking me if I needed a companion.

I strolled around the corner into the Square, seeing a big line of people in dresses like mine. It was a true sight to see, and there were a few photographers, probably from the Pink News, taking pictures. I strolled past them all and looped my ID lanyard over my head, going up to Big Joe, the doorman.

“Evening Joe. Big crowd of Wierdo’s tonight. Should be a giggle.”

“Evening Gene. You look fine, not like some of them out there, and that’s just the girls.”

“As long as they have a booking and the money, Joe, then we’ll all be happy come payday.”

“You’ve got it right, Gene. Have a busy night.”

I went in and made my way to the staff cloakroom, taking off my coat and hanging it up. Then I went to find the bar manager to find out where I was based. He took one look at me and sent me to the bar nearest the DJ station.

“Keep them hydrated, Gene, and try to move with the music. You have a full set of girls with you, tonight. I’ve put the rest of the lads towards the back of the club. Most of them look embarrassed to be in a dress but you totally own it, girl.”

I went to check my station and slipped a pair of small earplugs in. I’ve been here before and knew how loud it could get. Once again, I mainly worked with the waitresses, as it was strictly table service with a dance floor. The biggest difference with this bar was that we also did a line of cocktails, which I would have to make without the flashy moves as time was more important than show, unless a celebrity wanted to watch.

With the music going, the people dancing, and the drink orders coming thick and fast, the night went quite quickly. Finally, at closing time, I shut the bar down. All the takings were through electronic tablets that the waitresses held, which sent the drink orders to my monitor, and the meal orders to the kitchen. Any tips went through the same system and was allocated weekly.

I used the staff unisex toilet and got my coat, checking my face and putting the plugs in my bag to wipe when I got home. As I went towards the exit, in a stream of departing customers, the boss called me over.

“Gene. Don’t worry about bringing the outfit back. The fashion designer was really happy about the way the night went, and even pointed you out as someone she wants to see in her designs. She’ll be in touch and give me contact details for you to follow up. We’ll see you Friday night.”

“OK, boss, see you then.”

I followed the stream of happy drunkards outside, looking around for Howard. He was standing a few yards away with the most amazed expression on his face. I walked up to him.

“Howard. You really are a sweetheart. You look stunned.”

“All these people, all dressed alike but in different colours. It must have been bedlam in there.”

“This was a usual sort of night, except that the guys were all quieter than usual. It must have been the effect of wearing a dress. Thank you for coming.”

“I promised, Jean. I just didn’t expect to see all these couples hugging and kissing with them all in dresses. Does it get any stranger than this?”

“We did have one night, during summer, when everyone in the place was wearing a silk nightie. That was hilarious. Now, are we going home?”

He held his hand out to me, and I looked him in the eyes as I took it.

“This doesn’t mean we’re engaged.”

He laughed.

“Do you realise, Jean, that we’ve spoken to each other, today, for longer than we usually do in a week. How was your shift?”

“Non-stop, noisy, and my feet hurt in these heels. Walk a bit slower, please.”

“OK, if it takes longer to get to the flat, I’m good with that. Anybody special there, tonight?”

“In my area by the DJ, there were three girl singers who you would recognise, two film stars, no less than five fashion models and a princess. Fairly normal night, actually.”

“Wow! Is it like that every time it opens?”

“Usually. Saturday nights we get more music types in, and they sometimes do karaoke to the records. I don’t do the DJ bar every time, sometimes I’m up the back of the place, where the lights are low, and the settees are soft. It’s a lot quieter there. Oh! By the way. I was told to keep this outfit, so I could wear it again, for you. Maybe on your birthday.”

“In that case, my birthday is the fifteenth.”

“Which month?”

“All of them.”

We arrived at our door. I laughed.

“Do you want to come up, for a coffee, maybe?”

“Jean, you do know I live here as well.”

“Just having fun, Howard, Thank you for walking me home.”

I gave him a hug, as I had received a few in the last few hours, and he held me close as our lips met. I didn’t want to upset him, so didn’t pull away, and then his hand was on my butt, and I felt something between us. That’s when I pulled back.

“Hey, big boy. Thanks for the complement, but I really need my shuteye, I’ve got a lecture at eleven.”

He opened the door and followed me up the stairs, no doubt watching by butt all the way. In the flat, I gave him a kiss on the cheek and went to my room to get undressed and into bed after a very strange evening.

Marianne Gregory © 2026