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Housekeeper From Hell
  • Author - Anne Gray  
  • Rating -   
  • Site Rank - 59 of 2706
  • Unique Views - 31362
  • Story Codes - F-f, non-consensual, bondage, kidnapping, latex, slavery, toys
  • Post Date - 11/2/2008
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I glanced to the left of my computer screen checking the monitor for the dungeon camera. The hi-tech equipment picked up the slow, if somewhat strained, rise and fall of her chest against the tight leather of the straight jacket. Her legs were encased in a double leg boot; a skintight kid leather helmet covered her head and the extremely large gag that had taken a fair amount of work to install. A butt plug and dildo were held firmly inside her by a crotch strap attached to the jacket. Wide, heavy leather straps held her down starting at the forehead then every 12” or so down to the last one that crossed the toe of the boot forcing her feet into an even more incredible arch.

The sensual world of BDSM

Sure it was a bit of bondage over kill but Sheryl wasn’t in any position to complain and the image satisfied my leather Domme persona.

Sheryl was a study in contrasts and that was a real shame. On the one hand she was a raven-haired beauty in her early twenties who turned heads wherever she went. On the other hand she drank too much and then got a garbage mouth that cancelled out her attractiveness.

She was extremely wealthy with the inheritance plus the insurance money from the accident that killed her parents and I thought, wrongly as it turned out, that the memories of that terrible night might be why she drank so much. Instead of getting any semblance of relief from the booze it just made her antagonistic until the few friends she had wanted nothing to do with her. There was no family left so she drank more.

Living alone in a huge house didn’t help. She rattled around in it and had lost any purpose or direction.

The only other person in the home was me - the housekeeper. Well, for the moment, that’s what I was. It had not taken much to see the opportunity and she was drunk when I applied for the job.

“Just keep the f…king place clean and the bar stocked if you want to stay.” Those were her only instructions.

I had handed her another very smooth Tom Collins and asked when I could move in!

Two weeks before that conversation I had stopped for a late lunch before finishing the trip to my home about another hour away. It was an upscale spot and partway through my meal I had watched and listened as the maitre ‘d quietly advised the young lady at a nearby table that they would, unfortunately, be unable to serve her any more alcohol.

During the ensuing scene, when she exploded with a string of unprintable expletives, I looked around the room and noticed several diners just shaking their heads or grinning at each other.

My antenna went up and they were rarely wrong.

A quiet question to my waitress and I got the basics of the story before she said, “She’ll stay away now for about two weeks before she forgets that we cut her off and comes in again.” Then, with a bit of motherly concern she continued, “What Sheryl really needs is someone to look after her but she can’t even keep a housekeeper for more than a couple of weeks.”

During the rest of the drive to my beachfront condo I thought about what I had seen and heard. Several very lucrative deals over the last couple of years meant that I no longer had to practice the legal profession on a day-to-day basis; in fact, I could lead a life of leisure if I was so inclined. But I always kept an eye open for opportunity knocking again.

A week of research to confirm and expand on the details and I was convinced it really was opportunity. I got to work.

The manager/concierge of my building was very efficient, very good looking and very much my sub’. We enjoyed many sessions in my 25th floor penthouse condo ‘playing’ together when I was in my ‘leather Domme mood’ and I knew I could depend on her to follow instructions.

“I have a chance to pull off a major coup Janice and I might be gone a few days, a couple of weeks or six months depending on how things go. All possible expenses here have been covered and I’ll give you a cell phone number to be used only if there is an extreme emergency. Make sure the cleaners come in regularly and, if I’m not back in two weeks, I want you to call the dealer and have them look after my Jag’. Any questions?”

There weren’t.

At the local thrift store I put together a suitable wardrobe. Then, from a theatrical supply outlet, bought a mousy brown wig and two thin appliances that, when fitted over my teeth not only dulled them but also changed the features of my lower face and affected the way I spoke. It was a simple but effective disguise.

A visit to a used car lot, dressed in housekeeper mode, and $500 had me driving away in an overpriced ‘mechanic’s special’.

Two days later Ms. Sheryl Kerr hired me.

The first week or so settled into a pattern with few variations. Sheryl came down from her master suite around mid-day impeccably dressed and polite to her dowdy housekeeper.

If she was going out for lunch she poured a stiff one or two before leaving. If she was staying in to eat then I poured and served the drinks with the meal. In either case by early evening she was drunk.

And then it was yell at the housekeeper, criticize the food, the state of the house, what I had done or what I hadn’t done. It took her a couple of weeks before she seemed to understand I wasn’t leaving and then she tried another trick. Make the dowdy housekeeper her drinking partner.

On these evenings she would get maudlin and often drank straight shots of vodka with ice water chasers. And, of course, I matched her drink for drink except mine were straight shots of water.

Then I would get her upstairs, tidy her up and let the pattern start again.

After one particularly heavy session I made my move.

“I remember signing some papers last night, what the f...k’s going on?”

“Yes Miss here it is, you decided to open a small bank account for me to handle the household accounts without bothering you all the time.”

I showed her a paper that did exactly that and she backed off with a “Oh yeah, that was a good idea.” I didn’t show her the two others she had signed. They were Power of Attorney documents covering health care and financial matters. The executor was me!

When she left to drink her lunch at the golf club I went online and accessed the bank statements. The numbers blew my mind. Even though she was spending money like water, or should that be booze, it would be 20 years before there was even a dent in the principle.

I started a regular transfer to the household account; it was hefty but would not be noticeable among the other huge figures.

Another few weeks, during which ‘the housekeeper’ let drop hints, when doing the grocery shopping or chatting with the dry cleaner, that Ms Kerr had talked about maybe entering a clinic. This laid the groundwork of my plan.

I, of course, had the run of the mansion and found just what was needed in the basement. Sometime in the past there had been a fully stocked wine cellar down there. The fair sized room still had full climate controls, a large sink against one wall and a heavy lockable door. The racks were dusty and empty. When Sheryl was out of the house one day I slipped the gardener/handyman, who came by once a week, a few extra dollars and had him move the racks down to a back corner of the basement.

Over the next week I cleaned the room thoroughly, visited a hardware store in another town and picked up one of the new, odorless chemical toilets that I moved in after pouring Sheryl in to bed one evening.

The heavy cot took some planning but was eventually bolted in place.

I called Janice and instructed her to pack a couple of boxes with the supplies I needed and Fed Ex them to the post office in the next town.

Once I was satisfied with my arrangements a very drunk Ms. Sheryl Kerr visited her wine cellar for the first time in years assisted by the person she would come to think of as her housekeeper from hell!

The next two or three weeks were indeed hell for both of us as she went through withdrawal.

One day, once she had fallen into an exhausted sleep after another session with the DT’s, I drove the old rattletrap to town and since I had drained most of the oil, it seized up and died, as planned, in the middle of the main street.

The mechanic just shook his head over it and offered me a ride home during which I wondered aloud if, since Ms Kerr had checked into a clinic somewhere and left me to look after the house, would she mind if I used one of her cars?

I was going to anyway but the service station was gossip central and I knew it would be all over town in a very short time span.

After a month in the ‘dungeon’ she had lost a lot of weight and was hollow eyed but dry. I had been using sets of hospital restraints and found that a rubber covered ring gag was ideal since it took away the possibility of her choking.

Now I started to bring her back to a healthy state and gave her a choice. I could use the ring gag and a funnel down her throat to force-feed her pap or she could sit and eat normally at the table I had moved down to the room. Normally that is if you ignored the chain padlocked around her waist and the chair back, the cuffs holding each ankle to the chair legs and the short chains from the wrist cuffs to the tabletop.

She still chose ‘normally’ most of the time!

Similar restraints, except the ankle cuffs but with the addition of a very effective ball gag, were used when I took her up to the exercise room for half an hour in the morning and again in the afternoon.

While all this was going on the household account grew rapidly but not fast enough for me so I stepped up the pace. The ‘housekeeper’ was getting very fed up with the dowdy look and yellow teeth. So I let it drop around town that Ms. Kerr was coming along nicely and had decided that when she left the clinic in a few weeks she was going to charter a private ‘dry’ around the world cruise to make sure she didn’t have the opportunity to have a relapse. Then she was going to move somewhere that nobody knew her and start to live a normal life.

Another call to Janice confirmed that the unit next to my penthouse was still up for sale and I set things in motion to buy it.

Aroused by my thoughts I went back down to the dungeon and started taking the bondage gear off her head until I could get the gag out. Peeling off the shapeless dress I straddled her and pulled her head up until she could reach me with her tongue.

The first time I had tried this she was surprised to see that her housekeeper had a much trimmer and younger body than she thought; then she started swearing at me. Ten minutes later there was a large gag in her mouth, her legs were strapped wide apart and I came back down from the kitchen.

From the freezer I had retrieved two molds and I let her watch as I cracked them open to reveal penis shaped ice forms.

“You must learn not to do things to upset me Sheryl. I thought we had cured your garbage mouth but I guess you’re just a spoiled brat who likes to drink. It will probably take these quite a while to melt and that will give you time to think about things.”

One of the frozen toys slipped easily into her rear passage; the other inside her vagina. I strapped a pad of cloth over them and left to the sound of her muffled shrieks.

Since then she had become quite the expert with her tongue.

Satisfied for the moment I slipped a ball gag between her teeth, tightened the strap at the back of her neck and went upstairs to continue the necessary arrangements for completing my plans.

So now the house had been sold and, on closing, the proceeds would be held ‘in trust’ for Sheryl by her new lawyer - me. There are so many ways around that I’m laughing. Her accounts and all other assets joined the seven figure number for the house. The housekeeping account had been closed by ‘the housekeeper’ but actually was used to buy and re-design the other penthouse suite at my condo building. I now owned the whole top level.

The housekeeper had left town supposedly with a large thank you settlement. God I was so happy to dump the dowdy look, clean my own teeth and let down my hair.

All of Sheryl’s clothes and personal possessions had been shipped to storage and would stay there for a few months until things settled down and were forgotten. Then I would retrieve anything useful.

All that remained was to ship Sheryl to her new home. It would be so simple to just bundle her up and throw her in the trunk but that was not my style. I wanted something a bit more original that would make the journey interesting but not too comfortable for her.

I noticed that the Lexus SUV in the garage had a trailer hitch – hummm!



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Making sure that the cords holding Sheryl in a somewhat vicious hogtie were nice and tight I removed the plug from the ring gag. The wine cellar was almost soundproof and, anyway, there would be nobody else in the house to hear her grunts. Leaving her completely gagged while I was out would be stupid; the last thing I wanted was to come home and find her nose had plugged up and I had a body on my hands. Besides, now she was healthy, she was extremely attractive again and I had long term plans for us.

After a visit to the local trailer rental agency I returned to the house with exactly what I was looking for hooked up to the SUV. The box was 8’ long and just under 4’ wide. The sides were also 4’ high and the whole thing rested on a single central axle. Just behind the wheel on the right side there was a hinged loading door. A heavy tarpaulin, currently stored along the top front edge, could be unrolled and laced to rings all around the outside of the box about 12” from the top.

Since I would be making a few minor modifications to the trailer I had just bought it instead of renting and now pulled inside the huge garage where there was plenty of room. I had sold the three other cars.

The next morning I dressed in comfortable leather slacks, a light cotton top and ankle boots with sensible heels. Gathering everything needed I left some of it in a room next to the garage and carried the rest down to the dungeon.

The first move was to padlock a leather head harness, with a built in gag and blindfold, on Sheryl. That made her a lot easier to handle as I stripped off the few clothes she wore, threw a blanket down, and spread-eagled her to the floor rings.

Any resistance was minimal because, after I released her right arm and started working on the specially designed kid leather shoulder length glove, she just let it go limp. I put my knee on the wrist and leaned down to whisper in her ear.

“That’s one Sheryl; co-operate because you only have two nostrils.” Then I pushed a plug in the left side of her nose.

Now straining to get enough air she knew enough to straighten her fingers and arm once I removed my knee. That allowed me to slide the glove in place and lace it tightly. The left arm went just as smoothly. I felt she had learned her lesson so I pulled out the nose plug.

While I had her left arm I tied the wrist to another ring at waist level and then did the same to the right. This stopped her rather impressive breasts from being somewhat flattened, as they were when her arms were stretched above her head.

All I had to do was blow lightly across her nipple to get it ready to receive the flanged clamp. The pod of the clamp covered her nipple and was held in place with a small rubber tipped screw. The metal flange spread against the flesh to just past the areola and had small holes around its edge. When they were both in place I gathered up two 1” wide leather straps and tightened them around the base of each breast.

The top edge of the straps had small metal rings that lay flat against the bulging skin. If anyone took the time to count the rings they would find the number matched the number of holes in the nipple clamps. But that was for later in the process.

I re-arranged Sheryl so she was lying on her stomach with her arms under my knees at her sides. I wrapped a piece of cord around each wrist and ran the ends to a couple more floor rings just above her shoulders. It needed several hard pulls on the cord to get her arms up between her shoulder blades but once that was done the special feature of the gloves came into play.

A reinforced seam along each forearm held a small D ring every inch or so and I pulled on the wet rawhide as I threaded it through them. I used my knees to squeeze against her elbows as I played the hair dryer up and down the rawhide.

As I was doing this I took the time to dig my fingers in to her neck and shoulder muscles. Gradually her forearms came together and then touched in a classic reverse prayer.

The groans were understandable but I was not about to stop now.

She made a very tempting sight but I kept telling myself to wait until I got her home.

The boots took quite some time but eventually they were laced up to her thighs. They had no heels and just ended in a 2” round metal toecap. Fashioned in the ballet boot style they forced her feet to an angle where her toes were in line with her shins.

Now it was time to complete the breast bondage. Using a large blunt needle and more of the wet rawhide I wove a web of tight thongs between the straps around the base of her breasts and the holes in the flanges of the nipple clamps. I didn’t bother with the dryer; they would dry naturally from her body heat and would provide a uniquely constant squeezing pressure but do no damage. She didn’t know that!

I mentally stopped to review the rest of my idea for transporting Sheryl. The gagged and blindfolded girl didn’t stand a chance as I worked in the butt plug and then the dildo. Another small clamp went on her clit then I taped the fine wires from them up until I could join them to the other two whose contacts I snapped into the tips of the nipple pods.

That made just one control wire that I draped over her shoulder. Oh boy, it was going to be an interesting journey for this young lady.

The crotch strap to hold everything in place attached to a waist belt I slipped under her locked elbows. Now we were ready to move upstairs so I took off the blindfold. She just stared up at me shaking her head but then the tears started because I, again, leaned into her ear and said, “We’ve only just begun my pet. Wait until you see the rest of your traveling outfit.”

Pulling her to her feet I had to support her as she toe walked to the service elevator. The metal toes clicked, her chest was forced forward by the stringent position of her arms and I could see the wet rawhide was starting to embed itself into the flesh of her breasts.

One floor up and over to the room by the garage where she saw what awaited and tried to pull back. Fat chance.

Janice and Sheryl were very close in height and while Sheryl was just a little more voluptuous I was sure that, given a bit of effort, I could fit her into Janice’s full body corset. So I had asked her to ship it with the other ‘toys’.

The heavily boned gleaming black leather garment had cost a small fortune but it was worth it.

I let Sheryl lean back against the wall and her eyes never left what I was doing as she teetered on the toe boots. All the laces were undone and the corset was opened resting on a blanket on the floor. I had the sudden picture of someone trying to put a lobster back in its shell. Well, that wasn’t too far off what I was going to do.

With her arms useless and unable to balance in the boots without help it was easy to lead Sheryl over to the blanket and then, a simple tap against one of her toes and I guided her body down on to the leather prison. When she was down I strapped her ankles together and then got to work.

And work it was. The heavy leather started well below her knees, pinched in at the waist, had a tight pouch for her arms and ended with a neck corset that had a throat protector embedded. There were openings allowing her breasts to bulge through with the boned leather fitting closely around the straps trapping their bases.

I had to re-work the laces several times until I was satisfied that they were as tight as possible then I rolled Sheryl over and left her to adjust while I went back down to the wine cellar. The cot soon joined the old racks at the back of the basement along with a cleaned and disinfected portable toilet, the floor and ceiling hooks went in the garbage and the old wine cellar became, again, an old wine cellar.

Stopping by the kitchen for a bottle of water and the bar for something a little stronger I returned to the helpless heiress.

She was just about completely rigid from toes to neck and I knelt down beside my ‘lobster’ in her leather carapace to remove the gag and rest of the head harness.

“I’m just going to dribble this water in your mouth so you don’t choke. I’d advise you drink it because it will be the last liquid you get for a few hours.”

Obviously she was completely helpless with the bondage already in place but I would probably be faced with a bout of hysterics if she knew what was yet to come!

Once the water bottle was empty and I was refreshed with my own drink it was time to continue and that meant Sheryl’s head needed work.

The neck corset held her head steady as I rolled her first to one side and then the other so I could fit the miniature speakers in each ear. With the system turned off they would make her deaf, with it on I could conduct a one way chat to let her know what was going on or just torment her with word pictures of what I had planned for the future.

She tried to resist the gag but I just pinched her lower lip between two fingers and started to twist as I pulled down. More tears and then her teeth parted and I forced the hard rubber in behind them. There were channels in the top and bottom of the gag that, after a little bit of effort to get her jaws wide enough, her teeth settled into.

Even though her mouth was filled to capacity there was a 1” diameter hole through the middle of the gag and a hard hollow tube protruded past her stretched lips. I was not going to rely on her getting enough air just through her nose during this journey.

I pulled a rubber cap over her head, tucked in her hair, and then started to fit the leather helmet. I had been straddling Sheryl’s stomach to get the gag in and now fitted the breathing pipe through the mouth hole of the helmet, inserted the two short hollow rubber tubes attached to the inside up into her nostrils then stretched the leather up over the forehead.

Framed by the openings in the black leather her eyes stared up at me until I rolled the stiff form over on her stomach and started closing the helmet down the back of her head. The neck of the helmet extended down over the throat protector and I was able to tighten the laces enough to bring the two edges of the leather together.

Not satisfied, I fitted the metal ring of a gag strap over the tube protruding from her mouth and tightened the strap behind her head.

I clicked on the small microphone clipped to my collar and rolled her over to her back so I could look down in her eyes.

“Well little Miss Garbage Mouth now we have you nicely tucked up in all that lovely leather we need to hook this up.” I pulled the control wire down between her breasts, noting that the rawhide was still damp, and plugged it in to a small battery pack. Checking that I had a green light on the hand control I immediately shut it off.

“I think now that we had better do something to protect your outfit for our trip; hadn’t we?”

If looks could kill I would have dropped dead right then and there. But they don’t and I unpacked the body bag.

Starting at her booted feet I worked the stiff form inside the form fitting heavy rubber, stretched it to pop her shoulders inside and then pulled up the oversized zipper from her ankles, over her tormented breasts, up to the neck. Several half straps closed over the zipper pulling it even more tightly against the curves of her body.

There was a helmet attached but I first took a pair of rubber framed swimming goggles and settled them over her eyes, tightening the strap at the back of her head.

Now the hood came up and over her leather covered face. It had openings for the lenses of the goggles, under her nose and to allow the gag tube to protrude. I pulled the straps tightly under her chin and around her neck to seal the bag.

She had gone from a statuesque form in horrendously tight black leather to the same form but covered in shiny black rubber. In either case she was helpless; she was a vision of the bondage art and she was mine.

I was still not finished.

The net was just over 6’ by 10’ and made of heavy cord in a 3” mesh and I stretched it out on the floor close to the trailer. There was a mechanic’s trolley handy in the garage, the ones they use to slide under cars and I positioned it next to Sheryl’s body so I could roll her up on her side then back down on the platform.

That done it was a simple matter to wheel her over to the edge of the net. Rolling her off I wrapped the net along the length of her form and started her rolling again.

After three turns I used some twist ties to attach the other edge of the net to the layers wrapped around her body. Gathering the edges of the net at the top of her head I fed them in to a metal swivel clamp. Another one gathered up the edges just past her toes. I checked that the net was not obstructing her breathing or covering the lenses of the goggles.



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Believe it or not I got this idea from television. Flipping through the countless channels to take my mind off the downside of acting as her housekeeper, I had watched some idiot take a running jump at a hammock strung between two trees. He landed on the hammock then it twisted round and round until it had made him a prisoner.

It did take some effort to drag my prize into the trailer and hook the swivel clamp at the top of her head to the heavy turnbuckle I had attached to the forward edge of the trailer. I got a grip around her legs and lifted enough to guide the foot clamp into a turnbuckle at the other end of the trailer.

Using a short metal bar as a lever I worked back and forth between the two turnbuckles until, gradually the slight sag came out of Sheryl’s form and she was held horizontally face down about 2’ off the floor of the trailer between the two ends.

Now I needed a break, she wasn’t going anywhere and I pushed in an earplug to make sure I would hear if she got in trouble.

The shower felt marvelous after all my work and I pushed the earplug back in to hear Sheryl’s steady breathing. My dark blue leather skirt came just slightly below the knees, brushing against the top of the boots with easily handled 4” heels. I chose a white satin blouse to go under the leather waistcoat that matched the skirt.

As I walked around the mansion to make sure there was nothing unusual left for the new owners to wonder about, I worked on my kid leather driving gloves then, satisfied that all was in order, picked up the belted leather jacket to complete my outfit, locked all the doors and headed for the garage.

Standing in the trailer I easily twisted Sheryl’s form around on the swivels so I could smile down at her then let go so her heavily confined body flopped over until she was face down again.

I latched the door of the trailer and rolled the tarpaulin down to the end then laced the sides in place. More than enough airflow would get inside during the drive.

I flipped the microphone switch again.

“OK Sheryl my pet, we are going for a lovely drive now. I will try to avoid too many bumps that might make you twist in those swivel buckles but I can’t promise anything.

Pulling the SUV out of the garage I thumbed the switch on the hand control to the battery box activating the vibrators in the butt plug and dildo plus the butterflies resting against her clit and the nipple clamps. I set them at low to begin with planning to gradually make things more interesting for her as the trip progressed.

“Enjoy Sheryl, I’m going to take the long way around so you have about three hours before I really introduce you to life with a leather Domme.”


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Monday, November 16, 2009  

I have just now found the Anne Gray stories. Wow read two so far and as the others have commented great stories and I to wish that I could be the submissive

Sunday, October 25, 2009  

As asubmissive male I would love to be put in the same position.Is thre going to be more chapters?

Tuesday, December 30, 2008  

Are you going to continue this story? I certainly hope so; what you've written so far is wonderfully engaging, and it seems natural for subsequent chapters to unfold from this.

Tuesday, November 11, 2008  

I read and enjoy anything Ann Gray writes. Please keep up the good work

Monday, November 10, 2008  

Not Bad, but a force feeding device would have been a nice touch so the slave can remain hydrated. A enema ans urine collector would make her trim interesting too!

Sunday, November 09, 2008  

I have always loved Anne Grays stories
and this is no exception!Outstanding!!!

Saturday, November 08, 2008  

This is fantastic! I can't wait till the next chapter!!!

Friday, November 07, 2008  

wonderfull story, woman of my dreams

Tuesday, November 04, 2008  

WOW!!! great story. Love the bondage descriptions. I'd like to be in Sheryl's place. I hope you will continue this story. I want to know what is going on in Sheryl's mind. Woes she become a willing sub or a defiant rebellious one who neeeds instruction, discipline and punishment to change....or perhaps not. Maybe she is really relentlessly stubborn and proud.

Tuesday, November 04, 2008  

I want to experience this as well, awesome

Monday, November 03, 2008  

Nicely done. Excellent strict bondage. Will be looking for more.

Sunday, November 02, 2008  

Absolutely! Keep It coming! Greta STory!!!!

Sunday, November 02, 2008  

It was nice to read a new story from You Anne. I've always enjoyed Your strict bondage stories, always imagining myself in Your hands *giggles*

Sunday, November 02, 2008  

Great Job, Looking forward to the further misadventures of Sheryl.

Sunday, November 02, 2008  

Very good, well writen with good descriptive passages. MORE PLEASE.

Sunday, November 02, 2008  

Wow, glad to have you back, Anne! Great story, I want to see more from you! Perhaps a continuation?


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