Maid to Surrender

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Entering service can sometimes prove dangerous!
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CarrieQ
CarrieQ
159 Followers

When Mr Hastings first phoned me, I had no reason to think he was anything other than an ordinary client. I mean, so what if he asked me to turn up dressed as a chambermaid? That was one of the options mentioned on my business card. Transvestite maids have always been popular...

My maid's outfit was the flimsiest kind; really just a cheap black mini-dress worn beneath a white pinny. The hemline was so short that practically all my frilly red knickers were on view, along with most of my suspender belt and every last, square inch of my black, seamed stockings.

On the bus ride over to his place, I avoided unwanted attention by hiding my kinky attire beneath a stylish raincoat I'd bought from Harvey Nick's – just as I'd have done if Mr Hastings had asked me to turn up dressed as a nurse or a schoolgirl - the other options I offered back in those days!

I arrived at his doorstep in sensible sandals, but changed into a pair of black, four-inch heeled court shoes before ringing the bell. At the same time, I put on the frilly bonnet that went with the maid's uniform.

As I stood waiting for someone to let me in, I realized there was one thing about Mr Hastings' large, Victorian house that was quite unusual – it was still a large, Victorian house! See, every other property in that neighbourhood had been converted into an apartment block ages ago.

The man who came and let me in was so staid and serious, I half expected to see cobwebs dangling from his bow tie! And upon stepping over the threshold, my nose reeled so much from the smell of stale cabbage, that I began to wonder who these guys needed more - me or a real maid?!

"Follow me Missy," this white-haired dinosaur intoned stuffily. "Mr Hastings will interview you in the downstairs rear drawing room."

An interview? In the rear drawing room! I smirked a little, struggling to suppress a strong urge to ask what century this old duffer thought we were living in? And to add that I'd been booked for a minimum of two hours, which was to be paid up front in modern, decimal currency! But then I checked myself, figuring this was maybe all just part of an elaborate game?

After all, some folk really enjoy their role play...

I followed this strange old footman down a long, gloomy corridor. The floor was uncarpeted, so as my stiletto heels clip-clopped along the wooden floorboards, sharp echoes rang around the house...

It sounded a bit like somebody was getting whipped down in the basement!

Towards the end of the corridor, at the point when it was getting so dark I was contemplating asking the footman to light a candle, he paused to open a large door, before waving me inside a room that turned out to be surprisingly bright and airy.

It had elaborate white, ceramic architraves running up the walls, whilst the centre piece was a large, marble-topped table that money couldn't even think to buy. And sitting at the far end of this stone colossus was a dark-haired, beady-eyed man in his sixties.

The footman pulled out a chair for me, inviting me to sit down opposite this erudite-looking chap. To say I felt intimidated would be an understatement; the guy kept gazing at me like I was an object, rather than a person. It seemed like he was sniffing a piece of cheese – only my name's not Gorgonzola!

"Thank you for coming, Carrie," he said at length, breaking a silence that was beginning to make me sweat in strange places. "My name is Mr Hastings, though I hope you will eventually agree to call me Master. But in the meantime, you may address me as Mr Hastings, Sir! Is that clear?"

"Yes, Mr Hastings – Sir!" I replied, feeling foolish, intimidated – and thoroughly mesmerised.

Mr Hastings was never the kind of gentleman who wastes time before cutting to the chase; he explained concisely what he wanted from me. He wished to turn his home into a guest house for transvestites, who would spend their holidays living and working as chambermaids.

He was looking to employ a head maid who, along with his faithful footman Pooley, would run this enterprise to his precise instructions. The position was a live-in one, and would be extremely generously remunerated.

The only catch was, I would need to prove myself capable of absolute, unquestioning loyalty and obedience...

Having agreed to a trial, I almost fell at the first hurdle, when Mr Hastings ordered me to stand in front of him, pull down my knickers and masturbate. But as he stared at my sad and pathetic boy-bits, his eyes quickly glazed over, and I felt obliged to offer an explanation.

I was forced to confess how, as a teenager, I'd been punished for crossdressing by a gang of thugs. They'd grabbed my limbs, spread-eagled me, then swung me crotch first into a metal post, time and again, until I'd passed out.

Ever since that day, I've been warm where I should be chilled, cold where I should be hot – and floppy as a gelatine dildo...

For a long, worrying moment, I thought he was going to tell me it wouldn't do – that he would need to find another gurl. But after ruminating for a while, an idea seemed to cross his mind. "Pooley?" he called out to his footman, "Fetch Miss Carrie a pair of tights!"

At his command, I removed my stockings and sussies and put on a pair of black tights presented to me by the old footman, who then escorted me back along the long, gloomy corridor and up an interminably long flight of stairs.

Those stairs were so long and steep, we were forced to pause more than once just so that Pooley could catch his breath! You see, the house had high ceilings and large rooms, of a kind no normal folks can afford these days. Most of the other houses in the same road had been converted into blocks of six or eight apartments years ago...

When we finally reached the landing, Pooley instructed me to climb onto the banister as though it was a wooden horse, and then slide all the way down. Furthermore, I was to hold out my arms and legs rigidly for the entire descent, proving I was making no attempt to slow my progress.

By then, Mr Hastings, had ambled to the bottom of the staircase, from where he planned to watch closely as my crotch smashed forcefully into the solid oak finial topping off that sturdy old Victorian newel.

When I said I didn't think I could do any such thing, cos of the terrible memories it might rekindle, Pooley chuckled wryly, and said that was the whole point! In obeying, I would prove my worth and loyalty, and secure the job...

It wasn't an easy decision; in fact, I very nearly walked away. But a strange chemistry had already begun between me and Mr Hastings, who was proving capable of making me do things I'd never do for anyone else. And so, after a moment's hesitation, I took a deep breath and mounted the banister..

Closing my eyes, I spread my arms and legs wide apart, and trusted my fate to gravity. Of course, I was soon cascading rapidly downhill, with my boy-bits heating up as the nylon gusset – the only thing preventing them from being torn off – began sorely frying my tenderest skin...

With the burning becoming hotter by the second, the temptation to grasp the handrail grew and grew, until it threatened to overwhelm me. But even when tears started blurring my eyes I knew that, should I give in, then Mr Hastings would withdraw his job offer – and bizarrely, that seemed an even more horrible prospect than having my boy-bits burnt to cinders!

After several overly long seconds, my journey ended abruptly, with the sharp crunch of ancient oak pummelling my tender butt-cheeks.

As a visceral throb stretched down each leg from my burning crotch, I made no attempt to hide my tears. But my waterworks weren't caused simply by my painful, throbbing bum – I also felt thoroughly humiliated!

And yet... this was an agony laced with ecstasy! Cos to my utter surprise, I found my puny, useless boy-bits showing unusual signs of life! They were spewing out a wild cascade of cream, which was fast turning that hot gusset into a sticky morass of warm, steaming cum.

Patting me on the back, I'm sure I saw a smile flit across Mr Hastings's lips; but of course, I could have been dreaming. Keeping his demeanour rigidly intact, he told me sternly to climb down from the banister and remove my tights.

Taking them from me, he wrapped them thoughtfully into a ball before placing them under his nose, where he coiffed them, after the fashion of the judge at a flower show inspecting a prize-winning rose! And as he did so, I'd swear once again I caught the flicker of a smile – but I can't be certain...

Cos even if I'm right, he sure didn't let it linger!

Handing the tights back to me, he offered me the job, and asked me to start by waxing the banisters with those sticky nylons. He explained he wanted his house to stop smelling of stale cabbage, and to smell instead of juices squeezed from the loins of his new head gurl!

Needless to say, I decided to take the job...

Like I've already intimated, there was an element to my relationship with Mr Hastings which, right from the start, was reminiscent of Trilby and Svengali.

But with all my rent arrears and countless other debts, his offer was simply too good for me to refuse. See, I figured I could hide out in his mansion for long enough for all my creditors to forget about me!

Once I got home later that afternoon, I packed my bags as discreetly as I could, and when I left, it was creeping down the outside fire escape wearing ballet pumps, while my landlord was busy watching Coronation Street!

As arranged, Pooley picked me up around the corner, driving Mr Hastings' 1965 Model Two Jag.

At first, I was miffed when Pooley insisted on storing my suitcases down in the basement, but he was adamant; Mr Hastings would supply me with absolutely everything I needed during my stay. And, when I saw my bedroom in the attic, I was forced to stop grumbling.

The wardrobe was packed with dresses, skirts, blouses and pinafores – all tailor-made for a head chambermaid. Likewise, the drawers were stacked with panties, bras, corsets, stockings and every other kind of lingerie I could possibly want.

Upon the dresser, surrounding the large, illuminated mirror was a selection of wigs, short and long, bobbed and flowing, and in every shade from jet black through to platinum. And the table-top was simply crammed with all the make-up a gurl like me could ever wish for.

Then there was the shoe rack, which stretched so far up the wall you needed a stepladder to reach the top! It was filled with the most thorough selection of stylish black shoes I've ever seen. The only problem was, they were all black – like Mr Hastings had suffered a Henry Ford moment!

And what's more, I couldn't see a single pair with sensible heels, which got me wondering what I was supposed to wear on my day off? Naively, I decided to leave that question for another day...

There was one really freaky fact about all the booty in this glorious Aladdin's Cave – every single item was individually numbered and colour-coded!

Pinned on the wall was a rota – telling me exactly what I should be wearing, at each and every time of the day. Which wig, which panties, what shade of lipstick – everything!

"Pay good heed to this," Pooley told me, tapping the rota solemnly before he left me to settle in. "Think of it as your bible, and we'll all get along just fine – goodnight!"

"Goodnight, Pooley!" I replied, adding "You old freak!" once he'd safely left the room...

Glancing at the very first page, I was surprised to see it even included nightwear! That very evening, I was expected to go to bed wearing a red, silken nightie over a pink camisole with matching hold-up stockings! This seemed a bit extreme, but I decided, as it was only my first evening, I'd best play along...

After all, any little misunderstandings could be ironed out once I'd settled in - right?

I quickly fell into a deep slumber, but it wasn't a happy one! My dreams revolved around my landlord (and part-time pimp!) going on the rampage, searching all my old hangouts for me while threatening to hurt my friends...

When I woke up in the early hours, an ageing cock was pointing into my face, while a wrinkled hand was stroking my forehead. At first, I wasn't surprised – I'd been expecting Mr Hastings to come for his manorial rights sooner or later – but then, with a dreadful start, I realized it wasn't him!

"That's it, wake up, you dirty fucking sissy faggot!" Pooley hissed, the fumes from his roll-up cigarette making me choke and splutter. "I'm going to explain a few extra rules to you, and while I do, you might as well suck my dick!"

Bleary eyed and breathless, he really had me at a disadvantage as he grabbed my hair and pulled me out of bed. I was soon on my knees with his cock prodding firmly against my cheek, and there seemed no reasonable alternative other than to comply with his wishes...

So after briefly lapping his quivering cherry, I popped his hard, angry penis into my mouth, and began blowing and slurping. In no time at all, a trickle of salty pre-cum was dribbling steadily down my throat, and Pooley had composed himself into a somewhat less aggressive frame of mind.

"Ah, that's better, sissy!" he exclaimed, stroking my hair with surprising gentleness as he forced his manhood ever deeper past my lips. "We'll get on fine, you and me – now you know who's really in charge!"

As I sucked meekly on the old footman's respectable six inches of masculinity, he told me something of his life story...

He'd been Mr Hastings' loyal servant for over 30 years, during which time, the old man had bought and sold a property empire worth millions. But now, nothing remained - except of course for the house we were all living in.

All throughout this time, Mr Hastings had displayed a penchant for transvestites, which Pooley had frequently been required to help him indulge. And so his plan to open a specialist guest house had hardly come as a great surprise...

But when he'd proposed hiring a head maid, Pooley had baulked. And when Mr Hastings had made it clear that this creature would enjoy equality with him in terms of pay and status, he'd decided enough was enough...

Surely, his decades of loyal service should count for something?!

"Such betrayal – after I've given him my whole life!" Pooley thundered, but I was unable to answer. For as he spoke, he began ejaculating down my throat - pumping his salty cum straight inside me, whilst showing blissful indifference to my turgid struggles for breath.

As I lapped the wicked old footman clean, he began dictating my revised terms of employment through a malign sneer...

These changes would be strictly between ourselves; should Mr Hastings ever find out, I would suffer immensely! Firstly, we were not equals, and as such, he was retaining half my wages.

He was adding an extra item to the rota – a butt-plug – which I would wear whenever he decreed. And lastly and most importantly, I was going to help him obtain sexual favours from whichever of the guests happened to take his fancy.

Upon demand, I would make sure that pleasuring Mr Pooley was added to their list of duties!

Once Pooley left my room, I tried getting back to sleep, but it was no good. Whenever I closed my eyes, horrid thoughts would cross my mind, till eventually the only way I could get any slumber was by resolving to tell Mr Hastings everything about this unpleasant encounter, first thing in the morning.

I honestly believed he would deal with the vile old footman; that he would put my happiness and the safety of his transvestite guests before the dubious loyalty of a man who was clearly dishonest and dangerous...

But I was wrong!

Immediately after breakfast, I went to see Mr Hastings in the front living room, where he took his morning tea. He was reading a newspaper beside a roaring coal fire, while enjoying the view across the front lawn, where a sharp ground frost was gradually burning away beneath the gentle rays of a low, intensely yellow morning sun.

I was wearing a platinum bobbed wig, a white chiffon blouse, black knee-length skirt, seamed black tights together with black, peep-toe stilettos – all, naturally, in compliance with the rota.

"How may I help you, Carrie?" he enquired, casting a suspicious eye towards me. He didn't seem hostile, yet there was a coldness about him which I found profoundly unnerving. I feared I was irritating him!

"It's about Mr Pooley..," I began nervously, before my tongue ground suddenly to a halt. I wanted to go on, to spill the beans, to rat that rotten old footman out; but there was something about Mr Hastings' demeanour that stopped me in my tracks.

"If it concerns Mr Pooley, then take it up with him, not me!" the old man intoned, sounding bitterly betrayed and disappointed. "I rely on my staff to co-operate – do you not understand that?"

"Yes Mr Hastings, Sir! I'm terribly sorry!"

I curtsied, before hurriedly leaving the room in a dreadful fluster. On my way out, I bumped headlong into Pooley, causing him to nearly drop a tray. Needless to say, he gave me a thunderous glance.

Turning bright crimson, I fled as competently as I could – painfully aware that everyone watching me would guess my stride was being hindered less by my high heels, and more by the butt-plug I'd pushed up my anus, on Pooley's insistence!

As I spent the rest of that morning dusting and making beds, I wondered what I could possibly do to foil the evil old footman before he ruined everything – not just for me, but for the guests as well?

The first transvestites weren't expected till the start of the following week, which gave me several days to expose Pooley for what he truly was. If I was smart, then surely I could find a way of tricking him into betraying his true colours to Mr Hastings, long before then?

Of course if I failed, I realized it wouldn't just be me who suffered – paying guests; innocent folk simply trying to better understand their own true natures, would be cruelly, even criminally exploited by that sordid beast! And was there anything I could do to stop that?

I shivered, realizing the truth was, I simply didn't know...

CarrieQ
CarrieQ
159 Followers
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AnonymousAnonymous4 months ago
New Sissy

I now dress as a woman but now i am going out for the first time as a woman.I went in to the movie hard to see in the dark.Soon i could see three man having sex.I walked around and heard a voice telling me to come over and sit and talk to me.It was a nice black man and his friend.We talked for some time but soon i found my self on my knees sucking on his and friends black cocks.My first cock and i loved it i sucked both and swallowed their loads of sweet cum.Later that night i sucked off six hard cocks with four of them fucking me.

AnonymousAnonymousabout 8 years ago
nice story

ye I was made to surrender one day a man I work for call me in his office I went in and ask what he want he yell at me you are a no good bitch the work you do is alfull the only thing you should be doing is women work I told his if that what you want me to do then he said yes then he got up and walk over he told me to remove my clothes I did as told that when he saw my panties well what lovey panties you have on he ask how long you been in girly panties I told him a long time he ask if I was gay I told him no but the lady I use to room with but me in panties just then I felt his hand on my panties then he said yes you will make a good house bitch he bend my over a chair and pull my panties down I felt a finger go in my ass hole he work it in and out I move my legs a bit now my ass open he could get more of now two finger was in then he pull out his finger and unzip his pants and he pullout his cock he shove his cock in my ass hole it hurt as he pound my ass he told me that I have a tight pussy just then he shoot his hot load of cum in my ass after he pull out he turn me around and I lick his cock clean then I was told to put this coat on and come with him he toke me home with him throw some cream at me and go shower as I was in the shower he came in and start to wash me he did a good job as he dry me off I was told to do the same when I was at his cock he told me with your lips girly I toke his cock and shove his cock in my mouth well after that night I was in his bed and soon I was begging him to make me a girly bitch he told me as long you know who the man around here I said yes master I am your bitch and you own me now after a year I only wear girly clothes then it happen one day a lady came over and he told me she here to help you be more girly then he left I was turn around and I had my clothes remove she look at my breasts yes I think you should have 40 c cups breasts but first we will use these fake breasts for now she glue them on me and left some pills to take when my master came home she ask him well how she look she look lovey with them now girly show the lady how you thank her she just open her skirt and I saw her big man hard cock that right bitch this my first bitch and suck her cock I did and next thing I knew my dress was off and panties and he shove is cock in my pussy ass just then they both came my master shove his cock in my mouth and I suck him clean now after a year I became there house bitch

seasidesub01seasidesub01about 9 years ago
More please

Hi carrieQ, i would love to hear more from this story. It has been set up well. I look forward to hearing more.

Seasidesub.

AnonymousAnonymousover 9 years ago

Please make more to this story, I really enjoyed reading it and would love to read more.

AnonymousAnonymousover 9 years ago

Came a few times to this story, hoping to read and cum some more

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