Lady Ann's Holiday

By Emma Finn

Published on Apr 15, 2014

Transgender

Controls

Original Story by Eric – Expanded Edition by Emma

In which...wishing to avoid a dull visit to her grandmother, Lady Ann Neville takes drastic steps; giving her a holiday from herself and getting a little too much information on how the lower orders live.

Chapter One

Lady & Servant

1

England 1908.

It seemed to Burt that his life was always spent with his face pressed against the glass.

He worshipped Lady Ann Neville more than he did god in church, but Burt was only the stable hand at her father's vast estate, Griply Hall. His job was to muck out and groom the horses and perform manual labour around the estate. He was forbidden even from entering the manor house. He scraped an existence in the reflected light from this affluent and powerful family but he could never be one of them.

Still, he had his dreams – dreams that one day she would smile at him and say that - no it was too stupid for words. The distance between them was greater than it was to China. He might as well howl at the moon like a dumb animal. Lady Ann had hardly noticed him while they were growing up. Why would she notice him now? He was dirty and coarse; a big hairy man who couldn't even talk in a gentile way. She would never consider him as a friend, let alone a husband. He had no money, no education and no prospects. He could barely read or write. He had no proper manners and didn't know the first thing about how to be a gentleman.

Worst of all was the fact that he knew deep down in his heart that he really wasn't good enough for her. She was quality. He was a dirty great country bumpkin, not even fit to clean her shoes. He was thick as two short planks – enough people had told him so over the years – and she was a cultured lady, a distant part of the royal family. She could do anything and go anywhere. She had a life of riches and luxury before her. All he had was a drafty old hayloft he paid rent for and two suits of clothes.

Burt hurried away from the window of the manor. He couldn't see Lady Ann anyway and he might lose his place if he was caught. That would mean a life of destitution or worse: a job in the pit like his uncle, hammering at a coal face hundreds of feet below the ground, barely seeing sunlight and dying young. No. He couldn't possibly risk his position here. He was little more than a slave but anything was better than being down the mine. He didn't care about having to work some fourteen hours a day for only a pittance. At least he had a position and at least he was close enough to watch his beautiful Lady Ann from afar.

Burt went back to the stables and took care of the horses and cleaned the stalls. It was mucky smelly work but his strength made it easy. He was tall and very muscular, his shoulders broad and his arms thick. He took extra care of Lady Ann's fine filly, fondly imagining her taking the horse out next day while he stroked her down.

As he went to leave, he spotted a note that the groundkeeper, Harry, had left for him. He sighed, wishing he'd paid more attention in school and squinted at the letters on the scrap of soiled paper, sounding out the words.

"... Burt..." He paused. That word was easy. The rest weren't quite so simple. "Make... sh... make sure... that the..." He paused again, wishing the older man had simply told him what to do, looked round to see if anyone who could read was in sight, then sighed and went on.

"... pigs are... Make... sure... that the pigs... are... fed and... wartered."

Burt lowered the note and sighed again. He bet that Harry was already down the Dog & Pony getting the bevies in while he went on slaving! But he had to do as he was told so he went round to the back of the stables where the pig pen was and got to work. By the time he was done he was covered up to his knees and elbows in pig shit but that was nothing new. He only had one set of working clothes so he decided to let it dry on and then brush it clean in the morning. Likely as not he'd end up leaving it. He knew he smelled bad and there was no point in putting on airs like some pansy.

When Burt got up to the hay barn his busty girlfriend Mavis was already there, over from the pub where she lived and worked to play fun and games with him. She was showing off her legs and her cleavage and her smooth round shoulders and Burt felt his cock get suddenly erect. Mavis really enjoyed his virility and it helped him to forget for a moment his hopeless love for Lady Ann.

"Ey up Burt but you are you well endowed! Just like the stallions in the stables!" She giggled and then snorted like a pig, only illustrating how different she was from the refined lady of the manor in her voice, accent and ways.

Burt was pleased with the complement – he did feel proud to be her well hung man – and enjoyed himself as the night wore on, but Mavis was so common and crass – nothing like Lady Ann. He found himself imaging it was that beautiful gentlewoman underneath him instead of this uncouth girl, kissing him as he pumped into her; even loving him!

And he imagined what it would be like if she allowed him to love her back.

2

Next morning in the castle, Lady Ann was seething!

"Father you are impossible! You actually expect me to spend two boring weeks with dull old grandmama in London! There would be nothing to do there! No riding. No balls. Nothing worthwhile at all! She's an impossible old crone who does nothing but talk down to me and she's still in mourning for grandpapa!"

The Earl tried to keep calm. "Rail all you want, Ann, but you are going and that's that! I don't think a two week visit with your grandmother an unreasonable duty."

"That's because you don't have to go! Please father, it will be torture!"

"I've said my piece. I don't want to have a debate over it."

"I don't know why you don't just go and enjoy it," said Hattie, Ann's younger sister, from where she slouched on the chez longue. "I'd love to get away from here and go to London for a fortnight."

"Oh shut up you stupid girl," snapped Ann. "You're only saying that because they won't make you go." Hattie smiled to show Ann she was right. "We all know why they aren't sending you!"

Hattie started to speak.

"And don't think it's because you only twenty," cut in Ann. "It's not. It's because you don't have my interest in the arts. I'm actually being punished for my love of culture! Mother, can't you talk some sense into him?"

The countess smiled serenely from where she sat perfectly poised on the antique sofa and Ann's anger turned to a simmer. Her mother had always had a calming effect and never failed in her kindness and gentility. However angry and frustrated Ann could get (which was a lot), the countess was always able to still her tearing thoughts with her gentle love and patience. "I'm afraid you're going to have to go Ann," she said. "Grandmama is getting awfully old now and she needs someone near her who will understand her plays and will attend her high teas."

Feeling like she was coming to a dead end, Ann turned her anger on the earl again. "Damn it all, Father, you don't even like the old fossil! You are being most unreasonable!"

"I'm sorry Ann," he said. "You are going to London the day after tomorrow first thing and that is final."

Lady Ann huffed and stormed out of the room, irritated by the tightness of her long skirt which impeded the impact of her exit.

In the corridor, her maid, Gladys, was waiting. "Is everything alright m'lady?"

"Oh get out of my way you ignorant heffer!"

Ann stomped past to her room, ignoring the bewildered butler as she passed him too, becoming increasingly incensed on the way by her restraining garments and high heeled slippers slowed her progress. As soon as she slammed the door, shaking the house, she pulled off her shoes and hurled them at a vase, shattering it; then she snatched at her dress in a fury, trying to free herself. After several minutes of impotent but increasing rage she gave an angry cry and gave up, crashing onto the bed.

Life was so impossible! Constraints were all around her! She was so bored with being a lady! Why, if she'd been a man then her father could never have insisted on anything! She would have far more power than she had now! And anyway, if she wasn't a lady then grandmamma wouldn't be demanding she visit – the silly old harridan!

"God! I wish I could just cut loose and be slutty or vulgar!" she said with vehemence. "Being a lady – even being a woman is as confining as my corsets! Life is appallingly unfair! My entire summer is going to be ruined by having to do this! I'd do anything to get out of this ridiculous trip!"

For several minutes she seethed with anger, then she got to her feet and went to the door. "Gladys!" The maid didn't appear quite quickly enough. "Gladys!" she screeched.

The buxom maid came round the corridor looking harried "Sorry m'lady," she said in her idiot Yorkshire accent. "What can I do t'help?"

"You can do what you always do," snapped Ann. "Work half as hard as you should and do shoddy work." The attractive girl looked crestfallen, which made Ann feel slightly better at least. "Now get yourself in here and pack my things. I've been commanded to go to the capital and I will need all of my fanciest clothes."

"Yes m'lady," muttered Gladys. "Right away m'lady."

"Not that I'll get the chance to wear them!" cried Ann as she strode out, slamming the door behind her.

Thirty seconds later she strode imperiously back in. "I've decided to go riding. Perhaps that will cool me off; and for the next two weeks I'll be forbidden from enjoying the pursuit of it! Help me on with my riding habit!"

"Yes m'lady." Gladys said as she clumsily rushed to help.

"You idiot girl! Hurry up! You may not have anything better to do with your life but I do!"

"Sorry m'lady. I didn't mean nowt by it."

"And keep your mouth shut! Your crass dialect offends my ears. You need to mind your place. You're far beneath me on the social ladder for a reason. Just get on with your work and then get out of my sight!"

3

At the stables, Harry, the middle-aged groundkeeper, was looking over his record book making some notes, leaning on the edge of a cart. When he saw Ann coming he quickly stood upright and lowered the book, dipping his head in greeting. "Good morning m'lady," he said.

"Barely," she snapped. "It's almost time for luncheon."

"Can I `elp you at all?"

"Well what do you think?"

"Er..." the balding white haired man stuttered.

"This are jodpers I'm wearing aren't they?"

"Well, yes."

"Then I want to go riding, don't I, you twit!"

"Sorry m'lady. Quite right. I'll ave yer orse brought round."

"Don't bother you old fool, just get out of my way and do something useful. We don't pay you to sit around. We pay you to work!"

"Right you are m'lady." He leaned back and bellowed. "Burt! Get out ere you great wazock! Er ladyship wants to ride er orse!"

Burt appeared almost instantly from inside, flushing red from neck to ears. He took one look at Lady Ann and said, "Just a minute m'lady. I'll ave Rosebud out ere right quick and no mistake."

Ann turned her nose up at him as he disappeared back inside. Burt was dressed as always in his coarse threadbare clothes, striding through the muck without care. He probably didn't even notice. He spent his whole life in muck, just like one of the pigs in the field.

She was well aware of his hopeless love and worship for her. It amused her but there was no chance on God's green Earth that she would ever give him what he wanted. A man of his class was infinitely far beneath her; and if it wasn't for the filth she still wouldn't let him get close. He was clearly a simpleton with no decorum and little wit. Imagine the dinner conversation with such a dullard! Why, he could hardly discuss the finer points of Shakespeare; the subtleties of Madam Butterfly! Where she'd had an Oxford education, that dimwit probably hadn't finished even his first year of organized schooling – if he ever even attended any classes!

She had to admit though that there was something attractive about his huge muscular frame and broad shoulders. In her... very darkest fantasies she might wonder how it would feel to be taken up in those hard rough hands, to feel his thick moustache tickling her face as he kissed her... But only in a fantasy.

It was laughable really. The stink alone would negate all possibility of romance. He was nothing but a caveman compared to her and a far cry from the foppish and dull, but well-moneyed suitors who called on her from time to time.

Still it was nice to fantasize occasionally. Though if anything, it illustrated more the limitations of her position. She couldn't make love with anyone she chose, whenever she chose. She had to remain chaste until such time as a husband was chosen for her. It was oftentimes frustrating.

Even an ignoramus like Burt with less than a farthing to her name was far richer than she'd ever be in terms of personal freedom. An oaf like that had nothing to lose – he had so little already. He could sleep with anyone he chose, act anyway he liked, say whatever came into his head. Why, he could get falling-down drunk every night if he had the monies to do it. Lack of money was the only thing holding him back. If he had that then the sky would be the limit!

Yes, she enjoyed teasing Burt. It was gratifying to have men – especially burly strong men like Burt – so ruled by her. It was the only power and freedom she had, ultimately, in her frustrating cosseted life, where she couldn't even make a decision as simple as to whether to visit her grandmamma!

Burt bought her filly out and held the rein as she climbed up. "Hold her steady you philistine!" snapped Ann. "Come on you idiot, pip pip!" She sank into place on Rosebud's back and turned the horse to trot away, putting her back to the muscular young man. Then on an afterthought she looked back and smiled at Burt, toying with him. "Thank you Burt. That was wonderful. You're so strong and masculine... and sweet. A real treasure. I couldn't have held him steady myself."

Burt coloured from the attention, immediately ill at ease and confused, and Ann rode away grinning to herself at how diverting it was to have him and every other man she met so controlled by her whim.

As the dust settled behind her, Burt looked on giddily, then the mood broke as Harry rapped him round the back of the head with his pocketbook. "Stop gorping at what you can't `ave you dozy twonk! She's quality. She wouldn't look twice at someone like you. You're beneath her." He sighed. "We all are."

4

Ann came off the lane as soon as she could and set off over the fields. It was wonderful to be riding but going sidesaddle was such a bore and she quickly became irritated! She would have ridden astride if she could. But no - a lady never did anything comfortable! That would be too easy! A lady had to act with decorum at all times! She was sick of the rigid control her life was under, forced to act the lady without a second's break!

And she wouldn't even be allowed this simple pleasure in the capital. It made her blood boil to think of how unfair it was that she was being exiled to the dreariest house in Richmond.

She cantered as fast as she dared without sitting astride, heading to her favorite quiet spot by the stream. When she got there she dismounted and took a delicate seat on a grassy verge in the sunshine. She continued to fume about her predicament for several minutes... and then something caught her eye; a gleam at the stream's bank, just under the water line.

Curious, Ann crept down and saw that it was an amulet about the size of her palm, upon which was a faded engraving in the shape of an angel. She picked it up, turning it in the light, feeling its weight and staring at the odd design. As she did so, queer thoughts came into her mind that weren't her own.

She saw far off places and people in a rush of images and then obscure feelings rippled through her body and soul as she felt knowledge settle into her brain about what this trinket was and what it could do.

Lady Ann gaped at it incredulously. She had never believed that magic really existed but here in her hand she KNEW was an artifact of incredible power. She believed now in it utterly and somehow it had communicated to her exactly what its strange power was.

It could allow one person to exchange their very identity with another. All she had to do was wear it and embrace another human being and she would take on their body and life as they took on hers.

It was incredible! It was astounding! And it had to be fate!

The possibilities ran through her mind in an instant. With this trinket she could switch places with anyone she chose! It was her way out of this whole tedious trip she was to be forced into! She could trade lives with someone else for the fortnight and send them to London in her place! At the end of the tedious visit she could simply swap back using the same arcane device!

Was it really possible? It seemed unbelievable but she still knew without doubt that it was so.

The real question was who could she become?

Her father? That would be gratifying certainly. The thought of bullying him as she had been bullied was an exciting possibility, but she didn't want to be old and wrinkled and he would return the bullying with interest when she changed back! She shuddered at the thought of that.

For the same reason her mother was out. Though Ann was devoted to the elderly countess she couldn't rely on her keeping this a secret – especially if she had to suffer through the worst end of the deal – a tedious holiday at Grandmamma's! No, that was no good.

The third person who sprung to mind was her sister, Hattie, but again that would cause problems. The little sneak knew full well what an awful fright it would be going to visit the old dowager, and she certainly couldn't be relied upon to follow Ann's instructions. Even telling her about the amulet would invite disaster.

Ann started to feel frustrated. What had seemed a brilliant idea was quickly turning out to be untenable.

She needed someone who would follow her instructions without fault – do what she ordered them to from beginning to end. She needed someone so under her control or devoted to her that they would not only go through with the preposterous plan but put up with the down sides.

What about her maid? That was an idea... but Ann shook her head crossly. Hardly. The girl was almost as constrained as she was and not nearly as beautiful. Gladys was forever trying to fit into Ann's cultured household but never able to. And she was going to London as well anyway!

No. Swapping places with her would be the worst of all worlds.

Then suddenly Ann's lovely blue eyes gleamed. Of course!

Burt!

The clodhopper would do anything she asked and would keep his mouth shut. He was so servile and obsequious he wouldn't dare to not do exactly what he was told. He had no willpower of his own and his feeble uneducated brain would be incapable of doing anything but what she commanded him to. Why, he barely had the confidence in his own decisions to know when to eat or sleep and he really was moronic. If, in her place, he did something frightful at her grandmother's then it didn't matter! It would serve the old harpy right!

Ann's lovely mouth grinned full of mischief.

And Burt had a slutty girlfriend – Mavis; the barmaid in the village – attractive in a vulgar sort of way with prestigious breasts and a crude mouth. A good time was had by both according to Ann's maid who whispered how virile Burt was. Ann got the impression she'd been ridden by him herself in her earlier years.

Ann felt a rise of sexual excitement at the thought of really going through with it. She could have sex without fear of pregnancy or social status. She could ride astride, be vulgar, drink too much – even spit! It was too delightful – what a holiday she would have! It would be the most enjoyable two weeks of her cosseted life!

She thought of her grandmother and her stuffy friends dealing with the new 'Lady' Ann and actually giggled. Then she thought of herself: free and deliciously lower class and having sex whenever she wanted.

Sex as a man would be interesting, certainly. Just the thought of it almost made her faint.

Ann frowned. She was to leave first thing in the morning and it was already afternoon. It didn't give her much time.

She remounted her filly and rode back to Griply Hall as fast as she could.

5

Ann got changed in her bedroom, giggling to herself about how hilarious it was all going to be. She was on fire with excitement, her whole body buzzing at the idea of it! She hadn't felt this charged up and focused in a long time about anything. Finally! Something to make her relatively dull life interesting!

She couldn't get over how liberating it was going to be not having to mince round being cultivated, sipping delicately from teacups with her legs tightly together. Why, she'd be able to gulp from a pint glass instead! And get drunk! Why, she hadn't thought of that. She could get absolutely— What did the yokels call it? Squiffy? No. That wasn't lower class enough. It wasn't liquored up. Definitely not inebriated... She shook her head. It didn't matter. She was sure she'd hear all the colourful gauche language in the world soon enough. She laughed to think of it. Imagine! She'd never spoken an uncouth phrase in her life! Once she was Burt she'd be able to enunciate in as gutter a tone as she felt disposed to.

But that line of thinking made her pause for a moment.

Once she was Burt... That was an amply chilling thought. She shuddered. Then told herself not to be silly. She wasn't going to BECOME Burt. She'd still be herself. She'd just look like him. And it was only for a fortnight. That was all. Nothing could possibly go awry.

Still, she felt chilled for a moment.

But she shook her head and refused to lose her excitement. There were no down sides to this adventure! It was going to be fabulous!

She quickly got out of her riding clothes and contemplated for a moment what she wanted to wear while the swap took place.

She grinned and pulled out one of her most feminine outfits, a long sleeveless dress that showed off all her feminine charms... demurely of course. That was a given in her hideously restrained life! As she put it on she thought about how this would be the last time before her "holiday" that she would be a beautiful lady. She ran her slim fingers down her smooth arms and cupped her lovely face in her palms. What would it feel like to have stubble on her cheeks. She touched the yielding skin on her upper lip. To have a bushy moustache!

Why, surely it would tickle! She frowned good-naturedly. Perhaps that would have to go! She wanted to experience life as a man for a week or two but that was perhaps taking things too far!

Ann fingered her lovely soft hair. Burt had close cropped hair, barely more than fuzz at the sides and back. It was going to be hilarious! The silky material of her dress caressed her beautiful body... but it was still uncomfortable. Ann longed for the freedom of movement men's clothes were going to give her. Why, she'd be able to climbs trees if she so desired!

She took out some savings she'd secreted long ago from her hiding place and put them in a pouch ready to take with her and went to leave. Just before she did so, she took one last look at her lovely face in the mirror.

She was an elegant beauty.

A trapped and cosseted beauty forced to live the life her overbearing parents chose for her!

Well she was well and truly sick of it! For the next two weeks she'd have no one to tell her what to do! For the next two weeks she'd be a free man!

Rate this story

Liked this story?

Nifty is entirely volunteer-run and relies on people like you to keep the site running. Please support the Nifty Archive and keep this content available to all!

Donate to The Nifty Archive
Nifty

© 1992, 2024 Nifty Archive. All rights reserved

The Archive

About NiftyLinks❤️Donate