Lady Ann's Holiday: Chapter 7

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From Head to Toe


Anne woke up with a stretch and a yawn. The hotel she’d slept in was the best she could find in the scummier end of the city of York. It was a bit shabby but the bed was fifty times more comfortable than her pallet back at Griply manor and there were no gaps in the walls and window. It was probably the best night’s sleep she’d had since becoming Burt.

Since becoming Burt…

Ann tossed the covers back. She’d slept naked and she looked down the length of her muscular male body; at the hair on her chest and stomach and legs and at her thick masculine cock nestled in its pubic hair.

She took it in her callused hand and gently massaged it as she thought back to night before – taking those two slappers into the toilets behind the pub and shagging them hard from behind, one after the other. The more she thought about it, the more aroused she became and the more relaxed.

I love being a man, she thought to herself. I love being Burt.

Her penis was huge now, the big vein along its lower length pressing outwards as it engorged itself on blood.

She thought about the hilarious show she’d seen and the drinks with her new mates and even the fight she’d ended up getting into. And all the time she stroked her cock, running her big hairy hand up and down the shaft.

“I am Burt,” she said, caressing her knackers with the stubby fingers of her other hand. “I’m Burt ‘Arper, the stable hand at Griply ‘all. I’m a big burly hairy man and I ‘ave been since the day I was born.”

Hearing the sound of her man’s voice, thick with its Yorkshire accent, made her even more aroused. She didn’t rush what she was doing though. She drew it out slowly, just really relaxing into the pleasure, finding it intensifying the more she visualized herself as she was now – as a salt-of-the-earth working man.

She wanted it to carry on though so she let her mind wander, continuing to intensify the identification with herself as Burt; needing it to overwhelm her.

“I don’t fit into those posh places,” she said. “Not no more. I only fit in with me own kind now – with working men like me. Me own kind ain’t stuck up like those snobs at the restaurant. Me own kind’d never let a man like me down.”

She let herself drift, loving the slow sensation – the fantasy of pretending to be Burt. And she knew that the more she kept saying it, the more her accent changed; the more she really sounded like she was Burt. And that turned her on even more.

She was getting close to a climax now and she started pumping harder, looking down her body at her cock and her hairy legs; at her muscles and her overriding masculinity. Nothing that she was seeing said woman. She was a man from head to toe.

“I’m Burt!” she gasped. “I’m Burt!

“I’m a worthless lower class oike!

“An idiot!

“A dozy twonk!

“A filthy working class pillock!”

Then she came, spurting semen up onto her chest as she rocked with the force of her orgasm.

She lay panting for several minutes, loving the complete sense of relaxation and calm.

Then she sat up and swung her bare legs onto the floor.

“Ooah,” she groaned. “That was reet chuffing greet that was. Reet champion. Reet chuffin greet.”

Her voice sounded exactly like Burt’s now. And her sloppy masculine posture was his too. There wasn’t anything in the slightest bit feminine about her. And she loved it! It was great to play the part so perfectly. She’d been right to immerse herself in it. Strutting about like a woman in a man’s body had been a waste of the whole experience. Now she was loving every second.

It made her wonder what it would be like going back into her body. Would she retain her clodhopper accent for a day or two and still walk like a man? That would be hilarious!

But it would go soon enough if she just kept telling herself she was Ann again. There was no risk of getting stuck this way. And she could still talk like a swell whenever she wanted to anyway.

“I say,” she said, doing it now. “Awfully good show, what!”

She gave a manly chuckle. This certainly was the best of both worlds.

She got to her feet, remembering her intention to maintain her standards of cleanliness while she was living Burt’s life. Here in the hotel she’d probably be able to pay for a bath to be drawn for her.

But it seemed a bit pointless to be perfectly honest. Why bother putting on airs? The whole point was that she enjoy being Burt – not pretend to be some jumped up pansy. And bathing took far too long. She wanted to get out and enjoy the city by day as a man!

So instead she pulled on her dirty trousers and shirt, and her waistcoat and boots. There was a musty smell of horse shit and stale beer on the clothes but Ann shrugged. If they wouldn’t let her into posh establishments or first class carriages anyway then what did it matter?


While Burt and the duchess sat at breakfast on the balcony in the sunshine overlooking the park, Gladys fussed about making sure everything was perfect – checking that they had everything they needed.

Burt watched her, smiling wryly, while grandmamma read her novel. It was very funny to see Gladys being servile around him when for years she had looked down her nose at him. She had always put on airs, making out that she was superior, just because she worked directly for the gentry inside the manor instead of doing the manual work out in the farm buildings.

This was a real turnabout and Burt relished it. He would have loved for her to know who he really was but obviously he couldn’t possible expose his secret.

Instead he settled for saying, “Go and fetch me a fresh cup of coffee Gladys. This one’s gone awfully cold.”

“Yes m’lady. Sorry m’lady.” Gladys took the cup.

“And be quick about it this time. It was your dawdling that let it go cold the first time.”

“Sorry m’lady. Right away.”

Gladys backed away from the table looking flustered and ashamed and Burt’s wry smile broadened.


Ann had always loved to visit York Minster as a child.

It was a beautiful old cathedral with ornate architecture and a staggeringly beautiful interior. It was there, as a girl, she’d longed one day to be married. For many an hour she’d whiled away the time, imagining a handsome and wealthy lord coming to whisk her away from the tedium of Griply Hall to a life of great opulence. It was always here that she envisioned the wedding, filled to bursting with only the most highly appointed guests. She would be wearing a gorgeous white wedding dress with a train that ran back down the aisle thirty feet or more, carried by a whole cluster of pretty bridesmaids. It was the perfect place of her dearest childhood dreams.

Now though she was finding it boring as shite.

It had seemed a good idea to walk over here and wander round as she’d always loved to do but it really did seem pointless now she was here. What was the point of looking at a few spiky bits on an old church. Church was dull enough at the best of times. Wasting a perfectly good day in York looking round one was just plain stupid.

Ann got away from there as quickly as possible, hands in her pockets, cap firmly on, eyes wandering for something else to fill the time that wasn’t so pretentious and dull. She sneered at the rich folk strolling round gazing up at the place like it was important. They were all just wasting their time while trying to make out they was cultured or something.

As she strolled on she mused over how she was seeing life differently now. She supposed the obvious thought was that spending time inside Burt’s body and brain was influencing her likes and dislikes but she didn’t think that was it.

Being Burt was just giving her a fresh perspective. She was seeing life how a man sees it. Having a comparison allowed her to see her former interests from a new angle. It was nothing to do with what body she was in. If she, as Lady Ann, had been able to do and see the things she had recently then she’d have reached all the same conclusions.

Shakespeare was boring and confusing. All that pretentious old fashioned language was just there to make people feel inferior if they didn’t waste hours trying to decipher it. She didn’t have hours to waste! Now she’d discovered them she’d take a good music hall show any day of the week and twice on Sundays.

Same with wandering round old buildings. Rich people only did that stuff because they didn’t know there were better things to be done. Now she’d seen life on both sides of the curtain, Ann knew there were plenty of more interesting activities she could be getting on with.

And she was heading toward one now…


Burt and the duchess took a turn around the park as grandmamma’s manservant and Gladys walked ten paces behind in case they required anything.

Burt was wearing a beautiful long dress and white lace gloves. He wore a delicate wide-brimmed hat and carried a pretty little sun umbrella. Grandmamma was wearing her typical black.

“I must say Ann, your English has certainly improved over the last two days. You’ve been working hard.”

“Why thank you grandmamma,” replied Burt, feeling very proud of himself. “I am doing my best.”

“Well I must be a good teacher,” said the duchess. “When you came here you were acting very much the country bumpkin. Now I think you’d pass as a lady anywhere. It’s been an incredible transformation.” She smiled thinly. “I might even suggest it to an acquaintance of mine named George. He’s been looking for the subject of a new play.”

They walked on quietly.

Burt was elated. He felt that he’d finally done something right – doing more than a passing job of impersonating his beloved Lady Ann. He would never have guessed that he could do it but he had. He felt every bit the cultured lady as he took one ladylike step after another.

It still felt startling to be out in public, not only dressed as and looking like a woman, but acting like one as well! But as everyone around him not only accepted it, but expected it, it was becoming easier to accept himslef.

And if he was this good at being a woman now after only four days, how much more womanly would he be behaving at the end of the fortnight?!


After another hour’s walk back to the seedier side of the city, Ann started to feel a lot more comfortable again. It was strange. After being brought up in fancy houses and well-appointed manors, now she felt out of place if there wasn’t trash on the floor and filth and rust everywhere.

It all came down, she supposed to how she had been treated lately.

Among the quality she was looked down on and sneered at. Amongst the lower orders she was just treated decently; respected even because of the cash she had and her willingness to throw it about a bit. Coupled with the freedom of speech and action she still felt, it wasn’t a contest. Being around other people of her class was definitely better.

But that made her stop and pause for a minute.

People of her class…

Did she really think of herself as lower class now?

Surely not.

But she did. Sort of. But only in a positive way. She just saw the stuck up people from the upper class more objectively now. She looked down on them! If anything she saw herself as above every class now as she had all the best of all the differing traits.

Eventually she found the kind of establishment she was looking for.

As a woman she’d never been to one of course – had never even seen one! Truth be told she hadn’t even heard about them until the night before at the pub after the show where one of the other blokes told her how good there was a time to be had there.

Well after that she had to try it out. So here she was.

The cathouse was a sleazy-looking building on a back street with shutters hanging loose and paint peeling. In her former days she’d have run screaming from a place like that but she wasn’t chicken no more. Now she wasn’t afraid of nothing.

Outside the front a couple of slags were standing to lure blokes in, dressed in skimpy dresses that showed off their legs and cleavage. They were shockingly shameless but Ann just loved to look at them, even though they were scrawny; their cheeks sunken.

“You look well ‘ung luv,” one of them said. “Fancy a bit o fun?”

Ann grinned proudly. “Aye. Don’t mind if I do. With you or some other bit of fluff inside?”

“Inside,” said the whore. “Go on in. They’re waitin’.”

Ann gave her a nod and went through the door. The interior was dark with candles the only lighting. Ann was led by a matronly madam into the back where she had the choice of a young girl with barely tits to speak of, an older wrinkle-faced bike or a chink.

She chose the chink and got led up the narrow staircase to a tiny room with barely space for a three quarter sized bed.

The Chinese girl barely spoke English but Ann didn’t mind. She liked not having to talk first. That always seemed like a waste of time.

“I suck you,” said the chink. “I suck you good.”

“No,” said Ann, pushing the skinny girl back on the bed. “Spread your legs. If I’m paying then I want to get me money’s worth.”

“I suck you rear good,” said the whore.

“No,” said Ann, forcing her legs apart and pinning her down. “I told you. If’n I’m payin’ then I wants me money’s worth.”

The girl grunted as Ann put her weight on her and let out a little sigh as she was penetrated. She smelled of cheap perfume and some other oriental foody smell she couldn’t identify.

“Oooh. That’s good mistah. That’s rear good!”

“Shut up,” said Ann. “I didn’t come here to chat.”


Burt had never been to see a production of Shakespeare in a theatre or anywhere else. He had never had an interest in serious theatre, though he’d always enjoyed the farces and musical productions put on in Griply square by travelling players when he got the chance.

This was something else entirely.

It was a lavishly expensive production with extraordinary sets and costumes. The actors carried themselves with such power and presence. When they had started talking in their slightly archaic language he had sighed, thinking that he’d never understand a word, but in fact he picked up the meaning very easily.

It was a greatly moving production of King Lear and he found himself responding at a deeply emotional level to the scenes played out. He wondered why he’d never bothered with real theatre before. He had missed so much from his pointless life before now. It had been a total waste. His life as Burt just seemed so shallow and pointless compared to this kind of intense experience.

And of course it was delightful to enjoy the production in the best seats in the house, a box very close to the stage, seated with grandmamma; the servants on hand, standing quietly back but ready to step forward if called for.

Being a woman – being Ann – had expanded Burt’s appreciation of life so much. He wondered how he could possibly have been happy missing out on these pleasures… and determined to continue enjoying them after he returned to his proper life.


At York City railway station, preparing for the return trip, Ann was starting to feel cross.

She had a timetable but for the life of her she couldn’t work out how to use the bloody thing! It was just a mass of numbers and names. She scanned through the pages trying to find Griply but she couldn’t even find that. She tried sounding out some of the words but none of it helped. She was just getting more and more frustrated.

“I know you,” said a woman’s voice.

Ann turned and looked right into the face of her little sister, Hattie, standing dressed in a brand new dress and hat. She was taken aback by the surprise but felt relief to see a familiar face.

“Yes, I do know you, don’t I? You’re the man who cleans up after the horses, aren’t you?”

Feeling embarrassed to be labeled like that Ann nodded. “Yes. Yes… m’lady.” Knowing it was expected of her she tipped her cap, then felt a flush of anger that she’d had to.

“What’s your name?” said Hattie.

“Er… Me name’s… Me name’s Burt. Burt ‘Arper.”

She found herself glancing down at Hattie’s chest and then flushed from embarrassment, knowing that her sister probably noticed, feeling humiliated that she was doing so anyway to her own flesh and blood.

“Well Burt,” said Hattie. “I don’t know what you’re doing so far from Griply but you look like a little lost puppy. What’s wrong?”

“Er…” Ann felt awful being stuck in this position, having to pretend to be Burt to the sister she’d always lorded herself over, but she did feel confused and in need of help. She found herself saying, “I’ve got a timetable but I can’t read it.”

“You can’t read?”

“I can read. I just can’t… I can’t work out ow to read that.”

Hattie took it from her. “It’s simple.” She turned back the pages. “Look. You just find the place you want to go to – it’s in alphabetical order – then cross reference here, like so. That tells you the list of times the train leaves in that direction and what platform you need to be on. See? A child could work it out.”

Ann blushed and took the timetable back.

“My mother and I are taking the train back now as a matter of fact,” said Hattie. “You can follow us if you like.”

Ann smiled, relieved. “Thank you… miss.”

“Do hurry Hattie!” Ann looked round to see her mother beckoning to her sister to come. “We’re going to miss our train! Don’t waste time talking to filthy men, please. I thought I raised you better than that.”

“Sorry mother.” Hattie walked off, leaving Ann stewing.

Ann hurried after her but realised quickly that it would be frowned upon for her to walk beside them, even though their destination was the same. Instead she walked a dozen paces behind, watching her mother and sister chatter about all their purchase and the fun they’d had at the theatre.

Both ladies were wearing the gorgeous outfits they’d bought and each also had on new jewelry that cost at least as much money per item as she’d allowed herself as pin money for the entire two weeks.

Ann looked down at her own threadbare outfit with its ingrained dirt and musty stench and felt her ears burning again. It was silly. She could afford to buy new clothes and keep clean. She didn’t know why she hadn’t done so far. She was determined to do so from now on. Then people would treat her with more respect.

When they reached the platform the train was waiting. Ann followed her family along its flank but came to an abrupt halt when a guard thrust a hand in her face.

“Third class, you,” he said and pointed far to the back of the train.

Ann looked that way then looked again at her mother and sister climbing excitedly into first class.

This time she didn’t argue. She just sullenly walked down to the cramped and noisy carriages at the rear and took a seat on the hard wooden benches inside.


At the interval, Burt and the duchess sipped wine while they discussed the intricacies of the production so far. It was very enjoyable to comment on the subtleties of the acting and direction. Burt had never understood how a play came together but now, with grandmamma’s help, he was really getting to grips with it.

Gladys was hanging about looking a little bored. With a little smile, Burt called her over.

“Gladys. Go and fetch me another glass of wine will you.”

“Yes m’lady. She scurried off through the crowd. Burt couldn’t get over the power he had over her now. He waited patiently for her to return.

Gladys appeared with a second glass of wine and held it out to him deferentially. “Ere you are m’lady.”

“Take it back,” replied Burt. “I’ve decided I don’t want it after all.”

“… Yes m’lady. Of course.” Gladys hurried off again, struggling to get through the milling audience members.

Burt allowed himself another little smile.

When she returned this time he said, “Gladys, where have you been?”

“Sorry m’lady. I was taking the wine back.”

“Taking it back? I’ve called after you until my voice became hoarse. I decided I want the wine after all.”

Gladys almost sighed in frustration but Burt could tell she caught herself. “Sorry m’lady. I won’t be a minute.” She set off again and this time Burt actually grinned.

“Are you tormenting that girl Ann?” asked grandmamma from where she sat.

Burt looked at her sweetly. “Me grandmamma?”


“Well, perhaps just a little.”

Grandmamma smiled. “It’s quite a diverting pastime, isn’t it? I do it all the time.”

They shared a secret and absolutely delightful grin with one another.


Ann got off the train in Griply after trying unsuccessfully several times to nod off. The third class carriage was crammed so tight with people that she’d been jostled continuously, and being lower class oikes, they’d been unable to sit still and just enjoy the countryside. Instead they’d all just chattered and made a hell of a racket throughout the journey.

By the time she got through the squeeze and out of the train, her sister and mother were ahead of her. When she emerged onto the street they were already being helped aboard the manor’s coach, their baggage and purchases being packed safely away for them at the back.

Ann was tired but she knew there was no point asking for a ride. She’d accepted that. She wasn’t good enough for that anymore. She started up the road on foot.

The coach passed her several minutes later almost knocking her into the ditch. The coach driver threw her a wink and a grin and she tipped her cap without thinking. She was angry she’d been left behind but she reminded herself that she was trying to experience Burt’s life in its entirety. She was a working class man now. She couldn’t expect to ride with the gentry in their coach. As far as they were concerned, she was inferior to all of them.

If she was going to enjoy being Burt – and she was determined to do so – then she had to accept that part of what being Burt was all about. Burt had no right to ride in the carriage and she was Burt for now.

As long as she was, she had no right to ride in it.

Instead she decided to go and see Mavis at the Dog & Pony.

When she got inside the pub she found out it was Mavis’s night off. She went upstairs to her room and found the slutty girl naked from the waist up, brushing her long dark hair.

“Na then Burt,” she said. “I wont expectin you till tomorrow.”

“Ey up darlin,” replied Ann. “I left you a note. Dint you get it?”

“Couldn’t read the chuffin thing. Your handwritin’s terrible.”

Ann shrugged, feeling slightly irritated. “Well I ad a reet grand time in York anyways. Reet grand.”

This was the first time she’d seen Mavis since she’d really cracked the clodhopper accent and Ann noticed the contrast with pleasure. It was magical that she was able to produce the Yorkshire brogue so naturally now without even thinking about it.

Mavis went on brushing her hair and Ann maneuvered to get a better view of her tits, feeling the stirring yet again in her nether regions.

“You look like a right bewer when you sit there like that our lass,” said Ann.

“I thought you was gonna say I looked like an ‘ore,” she replied, smiling lasciviously.

“Aye,” said Ann. “That too.”

“Well get ere and climb on board. I ain’t got all night.”

Ann threw off her clothes and clambered onto the bed, stripping the strumpet’s skirt off her and nuzzling in between her breasts, feeling her arousal spike and then spike again.

“Oooah Burt,” moaned Mavis. “That’s it. Oh I like that Burt.”

Hearing her name come from Mavis’s nasal voice turned Ann on all the more.

Her name…

She closed her eyes as she pushed her cock into the girl’s minge, knowing she wasn’t quite wet enough yet but not caring; enjoying the wince of pain she gave.

Almost immediately she got a flash of the same fantasy she’d had the other night: that she wasn’t fucking Mavis; she was fucking herself – Lady Ann.

This time it didn’t surprise her and she relished it instead, remembering what it was like to see her own naked body through Burt’s eyes when they’d first switched. She replayed that scene in her mind, this time taking the tender woman in her manly arms and pressing their lips together roughly. She imagined throwing this Lady Ann down on the sofa in the cottage and she imagined climbing on top of her – having her way with her.

And all the time she pumped into Mavis; imaging it was Ann underneath her; imagining that she was taking her virginity; fucking her as she’d fucked the slags and whore in York.

She imagined she was pummeling Lady Ann over and over again with her massive cock and that Lady Ann was screaming out in pleasure; begging her for more.

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