I had worked as a buyer for a medium sized company with all the benefits one would expect that went along with an important position; such as a company car, expense account and all the rest one would normally expect. As it was taken for granted and everyone else had their little fiddles in such positions and so not to be different I also took advantage and I went along with it. These small but dishonest anomalies went on for some time and then one day I went too far in my greed, I actual sold some goods on that belonged to the company to an outlet I had found.
The MD of our company was Ms Jenkins. She had a reputation of not being approachable and had always kept herself to herself and even at our Christmas office parties which had become legendary she never came along. She was an extremely attractive and fit Lady around forty five with a good shapely body; always immaculately dressed but she was known as being a no nonsense bitch who always played the rules straight when it came to the workplace.
One Monday morning a week or two after I had sold on the “stolen goods” and thought I had got away with it I received an internal email to report to Ms Jenkins office at 10am sharp. I had no idea what was to happen and knocked on her door at the given time.
“Come” she beckoned me in. I entered and she was deeply engrossed in some paperwork. She didn’t look up but told me to sit which I did in front of her desk.
Finally she looked at me over her spectacles and spoke in a quiet serious voice. “You know I have uncovered a serious problem here in my company. Someone has taken some of the company’s goods and sold them on pocketing the money himself. Do you have anything to say about it?” She showed me the paperwork relating to the missing goods and then let me know she could prove my crime.
I flustered for a moment as the seriousness of it struck home. I shook my head and owned up. “What can I say Ms Jenkins, you know I have taken the goods and I can only say how foolish and greedy I was. I sincerely apologise for my error. I will pay it all back if that is any consolation”
She replied “Your apology is neither here nor there as this is your only choice now I have uncovered your grubby crime and yes you will be made to pay it all back one way or another.” She paused for a moment and continued, “Now I have considered what is to happen here; I am quite within my rights to fire you and to get the police involved aren’t I?”
I saw a glimmer of hope in her words and agreed with her adding that I would do anything she wished.
She leaned back in her leather chair and stared at me for a moment before continuing, “I had already considered what to do and this is what I propose. I don’t really wish to make this official and have the Police here and as you are I have to say very good at your job and with your useful contacts so I propose to discipline you another way. I will keep you on here for the time being to see how it goes in future and you will be watched like a hawk, believe me. You will pay all the money back which I daresay I will not get back if the police are involved and so I will stop it out of your salary so much every month”.
“Finally I do believe in punishment for crimes such as this and so you will report to me at an address I will nominate shortly at 7pm sharp on Friday where I will mete out what I consider something fitting. You will arrive freshly showered and clean, that is all I have to say take it or leave it, if you do not turn up then I will take it that you wish me to phone the police and also to fire you on the spot.”
She now got me to write down an address before saying. “Now go and get on with your job before I change my mind.”
I left quickly and felt extremely relieved at not being fired but I was puzzled at what she had in mind and was this her home address she was to carry out the “discipline” and what had she in mind?
I checked it out on my laptop when I found the time and decided it was not a place anyone in her position would be living as it was mostly old housing in an industrial area of the city.
I kept my head down all week and made a good effort at work but I did keep on thinking about Friday evening and what was in store for me there at the address I had been given.
As ordered on Friday at 7pm I knocked on the door with trepidation at the only detached house in this run down street. It was dark now at this time and soon the door opened with her standing behind it.
“Come” she said in a cold voice. I stepped inside, it was quite dark in the wide hall way and she closed the door and bolted it. She was wearing a long black leather coat and matching military hat. She showed me the cloak room. “You had better use the toilet and then come straight through to the red room.” She pointed to a side room further on down the corridor.
I used the toilet as she advised my mind wondering what was in store for me. I stepped inside the red room which was marked as such on the door. There was a low light in there and the whole room was decorated with red walls. Set in the centre was a low leather covered bench with heavy straps attached. On the wall in front of it was a full length mirror. There were other leather covered devices in here including a large cross; all fitted with heavy straps. My stomach turned over at the dungeon setting I had walked into.
She now stepped from behind the door and closed it as I turned to her in disbelief; she gave me a cruel smile. “Welcome to my dungeon” she said. “This place is especially for bad boys who need to be taught a lesson!”
She continued, “This is my alter ego; by day I am Ms Jenkins, by night I am The “Lady Bitch”. I am a professional sadistic dominatrix who enjoys breaking pathetic men who pay me very good money to do so and tonight it is your turn to be broken.”
“Oh my god!” I exclaimed, “what are you going to do?”
She returned “I am to teach you a lesson you will never forget, this evening will stick in your mind forever and you will refer to me as mistress whilst you are here, do you understand?”
She waited for my reply then repeated herself, her voice raised and agitated this time, “I said do you understand who I am to you right now.”
“Yes mistress,” I said foolishly and added, “what are you going to do to me?”
She closed in to me and spoke quietly, “I have reserved this whole evening for your humiliation and your degradation; I am also going to thoroughly scare you and to punish you here tonight for your dishonesty. I am also very expensive to session with as I am the best of mistresses and so you will also be charged for my time and effort.”
“I don’t know if I can go through with this?” I said as I was really filled with apprehension now.
She came back, “Well this is your final chance, stay here with me now and see what I have in store for you this evening or, if you decide to leave before I have finished then I will begin procedures on Monday.”
“This is blackmail!” I said.
“This is Justice and I am losing my patience here so make up your mind now!” she replied angrily.
She also now made it clear that I had nothing on her as she was a paid dominatrix and she could easily make it appear that I had volunteered to be here with her so I agreed, “Very well but please go steady with me, I cannot handle too much pain.”
By now her very closeness and the aroma of expensive perfume and warm leather of this very attractive lady and as she now stood only inches away peering into my eyes searching me was causing my cock to swell.
To my surprise she reached down and gripped my growing cock through my trousers tightly. “I see that I am getting you excited already so there is
one more rule, if you happen to lose control and squirt your filthy mess from this pathetic so called cock of yours without my permission then I shall force feed your slime back to you, won't that be a nice treat.”
I took a deep breath at her threat and she now said, “Come with me”, and still holding on to my erection she dragged me into another side room.
This place was full of ladies clothing and wigs and there was also a dressing table with make up and a large mirror.
“This is my TV room,” she said, “this is where filthy male perverts get their rocks off and are able to dress up and pretend to be ladies before they are punished and its your turn now so strip off all your clothes and let me see what you are hiding in those macho pants.”
My head was spinning with all of this and I obediently took off my clothes as slowly as I could folding them neatly killing time. “Don’t fuck about” she snarled, “you will get naked for me now!”
I finally removed all of my clothes and naturally covered my genitals. “Put your hands on your head slave,” she hissed, my head spinning even more I did as she said.
She now slowly walked around slowly inspecting me; my cock sticking out now, throbbing and oozing pre cum. She looked directly at it, smiled and now began to unbutton her leather coat where she now removed it.
She took my breath with her beauty now standing confidently, legs apart in a skin tight laced leather corset and a pair of skin tight leather shorts. With short fetish patent ankle boots, her porcelain beauty dressed so, made my cock even stiffer.
“You will not find a better view than this slave so make the best of it as the rest of the time with me will not be so good for you,” she said.
She now turned and began to select some rubber clothing including a pair of very feminine frilly knickers in pink latex. “Put these on to start with.”
she ordered. I looked at her incredulously. “Do I have to keep repeating myself, do as I say first time in future, now put these on now as firstly I am going to humiliate you,” she said.
Shaking with adrenalin I slipped them on and up my thighs; their coolness was very erotic and they now bulged bizarrely with my hard cock. She walked around me now grinning and making remarks; I was mortified with embarrassment.
“You need a bra too,” she said and slipped a rubber one onto my chest strapping it in place and then sliding breast prosthetics into the latex cups. I was then made to slip on high heel shoes and she followed this by placing a long blonde wig onto my head. “Nearly done,” she said and applied lipstick very messily on my lips and then added two cheek marks where she rubbed it in.
“Take a look in the mirror,” she said, “now see how good you look.” She laughed sadistically at my humiliation and now ordered me to follow her.
We entered a lounge area where she sat on a large leather chair and she now said, “Stand there slave I wish to see how ridiculous and pathetic you look.” The next few minutes I was made to turn and show myself off to her in the most humiliating manner and all I wanted was this to end as she poked more and more fun and belittled me to the core and began taking pictures on her phone.
She put on some music and said, ”Now dance for me like the silly twat you are!” I moved badly in the high heels so she criticised that too calling me all the useless names she could think of.
I still had an erection though despite my ordeal and after some time she tired of what she was doing, stood and collected something. She approached me, “I am in need of some refreshments but you are not dressed correctly.” She slipped a frilly latex maid headband around my wig and a tiny frilly apron around my waist before sitting down again and then calling me over to her.
She slipped my knickers down as far as my knees exposing my dripping cock. Looking up she gave a wicked grin, shook her head and said, “What is this?”
“Its my cock mistress,” I replied.
“A cock, you may call it a cock but I don’t,” she answered, “how on Earth do you satisfy any woman with that pathetic dripping tiny piece of flesh!” She shook her head to reinforce her statement and took more photos.
I was proud of my manhood but she made me feel inadequate now. She further humiliated it by producing a length of pink ribbon and continuing, “I think it needs something nice and feminine tied on it for now just to remind you how un-masculine you are.”
She proceeded to wrap the ribbon around my cock just behind my knob and then tied a bow tightly in it. “There that looks a lot better now!” she exclaimed pleased with her continuing humiliation of me.
“Now step out of your knickers and fetch me a large whisky,” she ordered.
I removed the knickers and hobbled over to the bottles of sprits pouring her a large one. The tiny rubber apron just rested on top of my jutting cock as I returned with her drink. She made me stand in front of her holding the silver tray while she slowly sipped it, all the time watching me and thinking up some more devilish ideas to carry out on me no doubt.
By now my calves were beginning to hurt due to wearing the high heels so I shuffled a little. “Keep still cretin!” she hissed.
“I'm sorry Mistress I am getting cramps in my legs,” I replied
“That is what you are here for, this is part of your punishment and do not
address me unless I ask in future,” she explained. I stood in agony now for
another half hour until finally she realised I could take no more and allowed me to remove my heels and sit until the cramps had receded.
Her clock showed I had been here for one and a half hours at this point and she now allowed me to remove my sissy clothes and clean up a little but I still had to keep the ribbon attached to my cock.
Naked I had to follow her downstairs now to the cellar area which had been converted into a prison area with chains, cages and steel devices. There was a winch in the high ceiling and on the floor lay a long leather bag with many straps attached.
“Lie down in that,” she said; I did this and found myself being zipped into the heavy hide bag like a mummy. She then proceeded to apply the straps very tightly until I was truly trussed up from my neck to my toes.
She lowered the winch which had a spreader bar hanging from it which she clipped to heavy D rings set on my shoulder area. I was hauled up until my feet were just clear of the ground. My feet area was now fixed to the floor via some straps to prevent me moving about too much.
She unzipped and opened the front of the bag exposing my cock and balls which she pulled out. With a long soft rope she now wound this around and around my cock and balls tightly and along my shaft covering it for its full length leaving just my knob exposed. Now tying it off I felt as if it was in a vice but it was also very erotic at the same time.
I now hung there totally helpless wondering what she was next to do; my heart beating with fear and anticipation. She had an array of rubber and leather hoods hanging on the wall and she selected a full head black rubber gas mask hood with a long trailing intake pipe for me. Soon it was slipped over and fitted my head with an air tight seal, the corrugated pipe hanging down.
“I do hope you are not claustrophobic but frankly I don’t care if you are,” she said with a shrug, “and so now for a special treat to complete your
next hour or so in here.” With that she collected a plastic jug and bizarrely and unashamed she unzipped the crotch of her leather shorts. She stood legs apart, held the jug in place and soon began to piss into it.
When finished she transferred her steaming contents into a plastic bottle that had an intake and outlet on its top. This she now hung on a hook hanging near to my left shoulder. Puzzled I now realised what she was doing when she now attached my intake hose to its outlet so that when I breathed, it sucked my life giving air in through her piss causing a bubbling sound thus forcing me to smell her waste.
Satisfied she said, “I will leave you down here now for the next hour in complete darkness. It will be quite scary in the darkness and you may panic as each minute will seem like sixty, but I will not return until your time is up so try to remain as calm as possible and this also gives you time also reflect on your deeds and as to why you are here.”
She left me, climbed the stairs and after the door was closed the lights were extinguished. Here now I was in total darkness with only the sounds of my leather bag creaking under my weight and my breathing intake permeating through her waste. As she had promised the darkness closed in on me as if a blanket had been put over my head and the claustrophobic feeling of the gas mask hood made matters worse as it became hotter in here.
After a while I started counting in my head to give me some sense of time and to try to remain calm while I was incarcerated. The time dragged by but thankfully the light came back on as she returned after an hour which seemed like a week.
This time she had changed into a gleaming skin tight latex catsuit which fitted her fabulous body like a second skin. Wow was she a sexy bitch.
I was now released from my gas mask and thankfully sucked in fresh air for the first time in an hour. She lowered me down now and soon I was free of the body bag but she made me keep my cock and balls roped up.
My body stiff from not moving followed her sexy rubber clad body up the stairs and we entered the Red Room again. She allowed me a few minutes to exercise my stiffness away before ordering me to straddle the kneeling bench.
She set about strapping me down very tightly over this frame so until I was helpless with my legs forced apart in a kneeling position facing the mirror. Satisfied she now stood in front of me and explained her next torment.
“You men are all macho pigs” she said “always talking about your conquests and how much pleasure you give your women. You are all ways making casual remarks about women like they are some sort of sex object put here just for male carnal desires, and you also make comments such as does she take it up the arse. Well tonight my slave I am going to show you what it is like to take it up the arse. It will hurt you physically as I fuck you, but it will hurt your mind even more to think that you have been fucked and raped by a mere female, and I will video it too for my own pleasure and keep to use if you do not do what I ask of you in the future.”
She now collected a leather harness which she strapped to her waist and thighs. This had a steel ring set at the front and she now opened a case where I could see inside which contained all sizes of rubber dildos.
My heart beating fast as to what I was about to endure I begged her not to go ahead. “Shut the fuck up!” was her reply and she pushed a dentist steel ratchet gag into my mouth and forced my mouth to stay open with it.
Now she selected a medium sized dildo and slipped it into the harness ring. “Time for a blow job from you”, she laughed and she poked it into my open mouth until I retched. “Lube it up!” she said, “you don’t want me to shove it up you dry do you?” as she continued to slide it to and fro.
My spittle covered the rubber cock and dripped onto the floor for the next few minutes. Having had enough at my mouth she now positioned herself at my rear where I could see her in the mirror applying oil to her cock and rubbing it in until it shone and dripped off. She squirted some of this oil inside of me too.
I felt her push the cock against my opening and naturally clenched my buttocks, “Do not try to stop me or you will be damaged and I will fuck you anyway,” she said, “relax and take it like a big girl!” With that she slid it into me slowly to get be used to it.
Yes it did hurt me and I squealed with pain and yes it degraded me too but there was something very erotic as I watched her pounding me through the mirror. Soon there were beads of sweat on her forehead as she moved her hips against me like a dancer. My cock still bound in the rope was throbbing wildly with all this attention and I just hoped I could control myself as I knew she would go through with her promise and feed it back to me.
She continued her assault on my rear and by now she was closing her eyes with pleasure as she was clearly enjoying my humiliation and pain. Suddenly she dropped her weight over my back, lay over me, shuddered and let out a low groan. I felt her body shaking all over for a minute as she by all accounts had an intense orgasm.
She stayed there lying on me for a while breathing heavily and when finally she stood up, her eyes still glassy she disappeared away into the TV room for a a little while.
Returning minus the dildo and harness she was quiet for a few seconds and then said after releasing my gag, “Did you enjoy the fucking I gave you?” I made a big mistake and said, “Not half as much as you did!”
Her eyes flashed with anger at my off the cuff remark “You cretin!” she hissed, “I intended to let you go after I fucked you but now I shall extend the session; you will feel the wrath of my temper with a good beating now for your insolence, your ass is mine and I will prove it.”
This was the thing I had dreaded the most since I had arrived here and through my own stupidity I was now to suffer even more.
She said, “Let me check your cock now to see if you have taken the forbidden pleasure before I beat you.” she released the rope from my cock and balls and this hurt me somewhat as the fresh air and a new supply of blood entered it
“There’s a lot of dribble on the floor here,” she said and wiped some onto her fingers before transferring it to my mouth. I retched a little at this and she now left for a moment and returned with a long large tube out of which poked several canes and whips. She placed this down in front of me and announced, “You will now determine how much of a beating you will be given as this will be in your hands shortly.”
Puzzled at her remark she placed a bowl underneath me on the floor and then she selected a clear plastic jug with a long thin rubber tube that was attached to an outlet on its base. There was a clip along the tubing that would contain its contents.
“Your mouth is dry is it not?” she quizzed me. I felt I was being set up and just nodded slightly. “We will have to fix that then won't we” she said sarcastically and now unzipped her catsuit crotch. She held the jug in place and proceeded to empty her bladder into it until there was a good half pint of her steaming piss in there. She held it up, admired it and remarked, “Hmmm delicious.”
I realised to my horror now that she intended me to drink it but how would this effect my beating? I soon found out now she explained as she hung the jug a couple of feet above me.
“I am very skilled at beating my clients; I can maximise their pain but leave very few marks as I slowly but severely lay my canes and whips across their pathetic bodies. When I am asked to present a judicial beating then all their screams of mercy just spur me on and I only stop when I am ready. I deliver just two or three strokes a minute to allow the slaves agony to reach its climax before I deliver the next one and you my slave are very lucky tonight as you can control when I finish your beating”.
“All you have to do is drink my delicious nectar where you will be timed doing so. I will then beat you for the same amount of time so if you finish it off inside a minute then you will only receive around two or three strokes and if you take ten minutes then around twenty five to thirty strokes will be your sentence. One more thing if you attempt to waste my nectar by spilling it into the bowl then it will be added back into the jug slowly.”
She let this terrible information sink in for a few moments as she now placed a stop clock on a low table in front of me and then attached the free end of the tube to a mouth gag with retaining straps.
“Please Mistress I can't do this, I cant drink your waste its disgusting!”
“Well I suggest you do drink it,” she answered, “because if you refuse then I you will take a judicial caning from me and only I will decide when to stop, you will probably be unconscious by then so what is it to be?” With that she offered the connected up gag to my mouth now. I allowed her to strap it on and found the tube now just inside my mouth could be controlled by compressing it with my teeth.
“Now I will open the valve and start the clock,” she said and she did just that. Her acrid liquid hit my mouth a second later and I clamped the tubing. I gingerly swallowed more of her waste slowly but this was to take some time, and time was not on my side.
I retched but had no choice so I tried to gulp it but this only increased the foul taste. Finally after some time and much to my disgust I managed to finish and she then stopped the clock; it had taken me six and a half minutes.
She removed the gag, cleared away the bowl and said, “There that wasn’t so bad and you did quite well for the first time.” She now unrolled a thin hide of leather around twelve inches wide with Velcro straps at each side and placed this across covering my buttocks; fastening it in place with the Velcro.
“This will help to prevent your skin splitting and also to reduce the long term marks,” she explained, “but it does not reduce the agony too much and I am to see that you are now punished for six and a half minutes, so I suggest you bite onto this,” and she put a solid leather bit into my mouth strapping it into place.
She selected a thin whippy cane after testing several by swishing them through the air with a frightening sound in front of me.
“I am ready to dispense your caning now,” she said and started the clock before moving behind me to my left. She took aim and brought the cane down sharply with a crack across the thin material covering my buttocks.
The pain exploded a split second later and it just seemed to increase for the next twenty or thirty seconds where a second one struck me. A third followed and this took my breath as I gasped through the gag. I was in agony by now as she continued with mechanical efficiency and I screamed for her to stop but she continued her onslaught and it was relentless. She paid no heed to my squeals and now my tears ran as the extreme pain continued until I thought I would pass out.
Finally it was over and I was left to sob as she now donned some surgical gloves. Approaching my rear with a small jar of ointment she removed the leather cover from my stinging buttocks. It was beginning to split where the cane had landed and she showed me this adding, “You did quite well here.”
She continued, “This is an anaesthetic for your wounds. It will reduce the pain considerably over the next few minutes and I will release you when I have applied it, so just lie there until you feel better”.
Her gentle hands were sweet relief and indeed I waited for around a half hour during which time the pain receded somewhat. I stood up now with my senses returned and exercised myself a little to return to as normal as possible.
Meanwhile she left and returned with what can only be described as a female torso made from rubber or plastic and strapped it on to top of the bench I had been lying across in reverse to my original position.
She smiled and said, “I am pleased with the way you have taken my torments and tortures and for your final task I order you to take pleasure now and rid yourself of that lust you’ve had all evening. I want you to fuck Rubber Rita here in front of me. You will then be allow to leave here.”
This was a final humiliation from her, my cock had diminished due to my beating and I was not really in the mood for an orgasm at this point. She squirted some slippery gel into Rubber Rita’s vagina and then onto my cock and gave it a few gentle strokes. I gasped at her touch and my cock immediately sprung into life.
“Come on,” she said, “now get your cock inside there, I want to see your best technique.”
Completely embarrassed I slid my throbbing shaft into the slippery rubber opening. It wasn’t as good as the real thing but it was very good just the same. I slid in and out a little faster in order to get it over with but she ordered me to slow down so that she could observe my humiliation. I did as she said as she stood in front of me in her erotic latex garb just smiling.
Five minutes of this and I needed release; she sensed it and now stood at my side leaning her hot rubbered body pressed against my naked skin. She spoke quietly and erotically in my ear, “Let me see your pleasure now, let it go, come on shoot your load into rubber Rita, come on fuck her harder now!”
At this I lost my control and my cock began to pump its steaming hot load, “Fucking Jeeeesus its coming ooooooooh Jeeeeesus” I cried as it left me in a jet of boiling lust. During my orgasm she uttered base profanities into my ear increasing my orgasm intensity until I was drained. I collapsed over Rubber Rita completely satiated at this point.
I was in another place for a few minutes before regaining my senses. “Come now,” she said in her controlling manner, “your time here is over and you may get dressed and leave”. I looked at the clock; I had been here for over four hours.
When ready to go she saw me to the door still clad from head to foot in her gleaming catsuit. “I do hope you have learned your lesson here tonight,” she said in her normal superior attitude, “now I will see you at ten sharp on Monday in my office where I will discuss your repayments.” She closed the door and I left for home.
That whole weekend my mind kept wandering back to what “Lady Bitch” had done to me. I had suffered every emotion from extreme lust to total humiliation and degradation in her hands and as she said I would never forget that evening for the rest of my life. Besides that I was remind by my backside being very sore for the next couple of days.
Monday arrived and I knocked on her door at ten. She opened it and invited me in; I heard the lock close. I sat as she ordered and I also admired her shapely backside as she passed me in her tight knee length skirt. As I sat waiting for her to open the conversation I still couldn’t believe what this creature had put me through less than three days earlier.
“So” she finally spoke looking over her spectacles, “I have worked out that you owe the company two thousand pounds for the goods you sold on and my fee for last Friday is five hundred pounds. I will not take my personal fee from your wages as this will raise suspicion and I have no intention of getting into trouble so I will stop two hundred and fifty pounds every month from your wages to clear your company debt. My fee of five hundred you will hand over in cash.” She hesitated for a few seconds and then hit me with her demand.
“You made a remark during your session regarding me enjoying myself. Well I have to admit that I never tortured anyone before who had not volunteered and it certainly gave me a great deal of pleasure torturing you so you will bring the five hundred pounds along on Friday night at eight in cash where you will again be invited to undergo another two hour session this time. This one will cost you just three hundred pounds. This three hundred will be owed to me and brought along at the following session which I will then determine. You will then come along with the owed cash for the previous session and so on until I have finished with you”.
I was flabbergasted and protested, “You didn’t say anything about repeat visits and its just not on, no I won't do it”
“Oh I think you will” she said, “I would hate for these to circulate on the internet wouldn’t you.” She turned her laptop around for me to see pictures of myself dressed as a woman taken last Friday.
“You fucking bitch!” I said in temper realising I was being blackmailed and there was nothing I could do to stop it.
“Yes I am a fucking bitch,” she replied triumphantly, “and when you visit me on Friday night you will find that I certainly live up to it as you are undergoing your invasive medical procedures while strapped down and helpless in my strict special clinic. This is run I may say by a sadistic rubber clad nurse who will give you a very hard time in there for at least two hours. I will see you at eight on Friday, do not be late!”
THE END – or is it?
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25.07.15 | updated - 07.05.17