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caught 3
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By (user no longer on site) OP
over a year ago
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If I may I am going to take you back in time and give you a bit of history about Miss Anna and how she became who she is. Believe me she was not born that way and most who knew her then would not recognise her now.
She had what could be considered a typical chav childhood. She grew up on a council estate with two brothers and her mother. Her father had long disappeared by the time she was five. Life was tough for them all, money being very scarce and the estate was not the safest place to live. Her mother did what she could but had her own struggles.
Cherry as she was known as back then did not have many friends, most girls around her did not want anything to do with her. By the time she reached her teens she was used to fending for herself and spending time alone. She used to hang out on the streets smoking and watching the world go by.
Then one day something strange happened. She had just turned 18 and was sitting on a wall having a cigarette. She was wearing a tee shirt and a denim skirt and ankle boots. All of a sudden she felt that she was been watched but could not figure out from where. Suddenly she saw an older guy dressed in a business suit leaning against a wall and all he seemed to be doing was watching her. If ever she looked at him he quickly looked away. She was in no way scared but she was intrigued. She tried to figure out the look on his face and finally realised that it was fear. He was scared of her.
As no one else was around she beckoned him over. He tried to resist but he could not and he slowly walked over to her. When he was beside her she asked
"Why are you staring at me? Is there something you want from me?"
He blushed and stammered that he meant no offence or no harm. For some time he had been fascinated by chavs but never had the nerve to approach one, especially one who smoked. His reply intrigued her and she wondered how far she could go. She looked him squarely in the eye and told him to kiss her boots. He went to walk away from was drawn back and did as directed. She all of a sudden felt more powerful than she ever had before. She told him to go to the corner shop and get her twenty cigarettes, which he did.
As she smoked they talked and he admitted that chavs like her scared him but he often desired to please them, to do what they said or get beaten up by them. This was not a total surprise to her as she saw how people reacted around her brothers. But to have a business man want to please her was something else. She wondered if there were others and was it just males. She thought that sometimes females may like a bit of rough as well.
Over the next few days they met and talked. He explained a bit more about his feeling and she became more convinced that he was not the only one. What she felt always held her back could actually be an advantage. A few weeks later he offered her a job as a cleaner, just a couple of days a week. She saw it as a starting point.
She was good at it and got a good reputation and soon built up a good list of clients. It just took someone to see past her ubringing and give her a chance. Over the next couple of years business flourished and she was able to buy herself a nice house. On her time off she researched more about kink and fetish. She also realised that people trusted their cleaners, told them things they may not tell close friends. This where the second business came from.
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Good back story sissy. Well done. Hope when you write these you are plugged and locked like the sissy whose story you document |
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By (user no longer on site) OP
over a year ago
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"Good back story sissy. Well done. Hope when you write these you are plugged and locked like the sissy whose story you document "
If only |
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By (user no longer on site)
over a year ago
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Wow xx |
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By (user no longer on site)
over a year ago
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By (user no longer on site)
over a year ago
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Wanting more |
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By (user no longer on site) OP
over a year ago
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The second business started slowly. It took time for Cherry to get to know her cleaning clients, their hidden secrets and what she could help them with. It started with males like the one who started it off. They were scared of her but also respectful. Now and then along with the cleaning fee some would add in some cigarettes making sure to know what her favourite brand was.
Then one day when cleaning a room she found a maid uniform in one of the rooms. At first she said nothing but eventually built up trust with Sam, the client. He eventually admitted that rather than having a maid he wished he was the maid but knew nothing about cleaning. Cherry then offered to teach Sam how to clean for the same fee he gave her to clean. She would come as normal but he would do the work and she would inspect. It did not take Sam long to agree.
Over the next few weeks Cherry thought Sam how to clean to her high standards. He was always dressed properly and took her notes very well and proved a loyal student. The time with Sam helped Cherry to spot other submissives and sissies she could control.
Her first female bitch came out of the blue. She had started cleaning for Helen, a posh lady who lived alone in a very nice house. There were other staff but Cherry was asked to go in once a week and do some clothes washing and ironing. Nothing untoward happened at first but then one day Cherry arrived a bit early. As she approached the laundry room she heard a sound coming from the living room. It sounded that Helen had guests. Suddenly Cherry heard
"Please don't hit me again Miss Cherry I will do as you say"
Intrigued Cherry sneaked closer and looked in. She found Helen lying on the couch, dressed in a white blouse and leather skirt. Her skirt was bunched up around her waist and one of her hands was between her legs and was rubbing her pussy. Not realising she was being watches she continued to say
"Please please Miss Cherry show mercy".
Taking this moment Cherry stormed into the room and said
"Why should I show you mercy Helen?"
Shocked Helen stopped what she was doing and looked at Cherry, not knowing what to say. Cherry spoke
"Imagine me finding my posh client playing with her pussy dreaming of being my bitch. Well I never. Now unless you want everyone to know get on your knees right now"
Knowing she was caught Helen got off the couch and knelt. She begged Cherry to keep this to themselves. It was just a little fantasy she had from when she was younger and people thought she was too good for her boots.
"Well let's make sure you don't feel better than me. Crawl over here, kiss my feet and agree to be my bitch. Or else every knows what you are."
That led to a few fun months with Helen and a huge learning curve for Cherry. She reinvented herself, changed her name and looks and never looked back. Anyone who saw Miss Anna sitting in the pub waiting for sissy would never recognise her as the chav estate Cherry.
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By (user no longer on site)
over a year ago
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By (user no longer on site) OP
over a year ago
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When sissy arrived at the pub the following evening, Miss Anna was already waiting for him. She was dressed in a very elegant short black dress, high heels and black leather jacket. She looked way too classy for the pub. She explained, not that she needed to that she had a business meeting afterwards.
She sent sissy for drinks and then debriefed him on the weekend,the two cleaning shifts and the visit to the adult store. He was relieved to hear that Miss Marie, Miss Jane and Princess Sara had given good accounts of his behaviour and service. She said that she expects requests from Miss Marie to use sissy again.
"It's just as well you don't have many friends or hobbies sissy with the demands I have on your services. Speaking of demands John is waiting for you so go pleasure him with your sissy mouth"
As if on automation sissy headed to the toilet, discretely entered the disabled one where John was. There was no talking, just down on knees and straight to work. The dildo practice was working and it did not take long for sissy to have a mouthful of cum. As he left John slapped sissy's ass and said that he couldn't wait to use that hole.
On his way back to Miss Anna, he accidentally bumped into a woman standing at the bar. Like Miss Anna she was dressed way too elegantly for this pub. As he apologized, she said not to worry and asked how he knew Cherry. As he was about to ask who Cherry was she had vanished. He was not sure if he should say anything to Miss Anna about it.
When he got back to the table she was on her phone. Motioning for him to sit and be quiet, she carried on talking for a few minutes. All he could hear was
"That sounds fun...........will make sure sissy is ready........you have full control"
No idea what was going on but would know whenever Miss Anna felt he needed to.
She finished the call and put her phone away. She looked at sissy and said:
"Your outside work rota is as follows
Every Tuesday evening you clean for Miss Jane
Every Wednesday evening you clean for Princess Sara
Every Thursday evening you visit John at his and provide him oral pleasure until your ass is ready
Every Friday evening you clean your own flat
Weekends are yours unless I need you for something special
Understand sissy?"
Sissy just nodded.
"As for the phone call Miss Marie wants to take Amy to a BDSM party and she wants gimp's help with the bags etc. She will meet you at the shop at 6 on Saturday to prepare you."
Miss Anna then got ready to leave for her meeting. Just as she was about to go sissy asked if he could ask a quick question. When she agreed he asked
Who is Cherry? |
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By (user no longer on site)
over a year ago
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How dare he ask that |
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By (user no longer on site) OP
over a year ago
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Trying not to show her shock at that name again, Miss Anna looked at sissy and why he asked. He explained bumping into someone who asked how he knew Cherry and then just vanished.
"Nothing for you to worry about sissy. Now you almost let me go before giving me bitch's chastity keys. Next time we are alone I will deal with that error. Give me the keys and go home and practice your dildo sucking."
Sissy quickly handed over the keys and watched Miss Anna leave. He could see that she was worried but had no idea why. He decided not to worry about it, went home, ate and practiced his dildo skill and went for an early night.
As she left the pub Miss Anna tried to pull herself together. She had done as much as possible to move away from her old life and thought she had succeeded. So who was the woman who had spoke to sissy and what did she want.
Shortly afterwards she arrived at her business meeting. It was a get together for local entrepreneurs to network, swap experiences and get tips on how to move forward. Her cleaning business was going well but things could always improve. She was also on the look out for new clients for both sides of her business. There were quite a few people already in attendance, all dressed professionally and some waiters/waitresses walking around with trays of drink. She took a glass of water and said hello to a few people she knew and spoke to a few new contacts.
As she circulated around she spotted a very well dressed woman, in her early fifties. She looked very in charge and dominant, characteristics that Anna could appreciate and recognise. She wondered who the woman was and how to be introduced. Surprisingly the woman noticed her looking and made her way over to her. She offered her hand and said:
#Hello my name is Ms Jones and I am in property management. I believe you run a successful cleaning company and thought we may be able to be of use to each other"
Anna replied that it was nice to meet her and she was always happy to discuss business opportunities. They swapped cards and arranged a meeting at Ms Jones office for tomorrow at 10am. They then parted to continue circulating.
A couple of hours later Anna left, feeling the meeting had been worth while. She had almost managed to forget the upsetting news of earlier. Even though it was ten pm she picked up her phone, rang a number and said
"bitch I expect you naked at mine in an hour" |
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By (user no longer on site)
over a year ago
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By (user no longer on site) OP
over a year ago
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As she arrived back at hers forty five minutes later she was impressed to see bitch's car there. As Miss Anna got out of the taxi, bitch got out of her car, wearing a coat and heels. As Miss Anna opened the apartment door bitch took off her coat to show she was naked apart from her chastity belt and heels. She got down on all fours and crawled in after Miss Anna.
"Good bitch now head to the basement and I will meet you there. Bitch crawled off and Miss Anna went to get changed. When she arrived in the basement bitch was kneeling. When bitch looked up she gasped Miss Anna was naked apart from a strap on. Firstly Miss Anna undid the belt and then told bitch to get over the kneeling bench and strapped her in.
"You may not enjoy this bitch but I will and that's what counts."
She walked away and picked up a cane, came back and without warning gave bitch ten hard strokes across her ass. This made bitch jump against her restraints and left marks. They were followed by another ten harder ones. The dildo was lubed and harshly entered bitch's very wet pussy. This was not about getting bitch off, it was about letting out Miss Anna's frustration as she fucked bitch hard and fast. This went on for a good fifteen minutes as bitch fought against her restraints.
Finally Miss Anna withdrew, took off the strap on and walked around to the front of bitch. There were tears in her eyes.
"You have a choice bitch, go home now or spend the night with me and go home in the morning. The belt is going back on and this is just sleeping."
"Understand Miss Anna and please I take the second option."
Bitch was unstrapped, salve was placed on her ass and the belt was locked back on. She was helped upstairs to Miss Anna's bedroom, given a negligee to wear. They cuddled in bed as they fell asleep.
The alarm went off too early it seemed but bitch had to have time to get home, change and head to work. Miss Anna relaxed for a while and then got ready for her meeting. She dressed in a black business skirt suit with white blouse and knee high boots.
When she arrived at the address given she was greeted by a young female receptionist who told her that Ms Jones was waiting for her. She was shown up to the office and shown in. Weirdly she heard the door being locked behind her.
When she turned around she was stunned at what she saw. Expecting to see Ms Jones sitting at her desk waiting for her, she saw her naked, kneeling with her legs open, hands on knees and head bowed.
Before she could say anything Ms Jones spoke:
"You have no idea how long it has taken me to track you down Miss Cherry. Even without you nearby I have tried to remain your loyal bitch" |
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By (user no longer on site)
over a year ago
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By (user no longer on site)
over a year ago
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Not much of a surprise you told us about her at the top of the forum ?? |
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By (user no longer on site) OP
over a year ago
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"Not much of a surprise you told us about her at the top of the forum ??"
you are free to not read if you dont like the twists and turns |
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By *hil911Man
over a year ago
Solihull |
"Not much of a surprise you told us about her at the top of the forum ??
Maybe you should write a story then??
you are free to not read if you dont like the twists and turns"
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Fantastic stuff, keep it up sissy! |
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By (user no longer on site)
over a year ago
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Love it |
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By (user no longer on site) OP
over a year ago
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Helen, it suddenly clicked with Anna. That's who was on the floor on her knees, that's who remembered Cherry. She had forgotten that when someone releases their inner selves for the first time it can be a powerful moment and can be hard to put it away again.
She looked at the woman in front of her, not a bad body for her age, she had obviously looked after herself. She walked over, put the tip of her boots between Helen's legs and pressed down on her pussy lips. Helen just sighed. Anna walked over and took a seat. She said
"I was expecting to come here and discuss a business contract for cleaning properties managed by your company. Instead I see an old whore practically offering herself to me, for me to do with what I want. Do you really want to go back there, do you remember how cruel I was to you, how much of your dignity I took from you? Do you expect me to still be interested or to be any less gentle now if I decide to abuse you again?"
Helen looked over at Anna, though she would always think of her as Cherry. She spoke softly:
"The contract is real and is on my desk. You can get it checked over and believe you will find it very fair and profitable. What you see here is something extra, which as always you have the right to accept or refuse. I don't think you fully realise the impact those few months had on me. From the moment you walked in and caught me masturbating while calling out your name, my life changed fit ever. Those months of being your bitch were some of the most exciting of my life, even with what you put me through. I was so lost when you broke off contact but knew I could not go back to what I was. On one side I became a very successful property developer, very well off and respected. On the other side I sought out young ladies like you, to use me, abuse me. But of course none were like you, none had your built in natural skill. Some tried, some just took my money and ran. But I carried on and eventually found one who came close to you. You met her as she is now my trusted receptionist and knows in what state I was waiting for you today"
This honesty and deep desire took Anna by surprise and she had to admit to being impressed. She asked how Helen tracked her down. Helen explained that she hired private detectives and they eventually came good. She arranged the bumping into sissy and being at the network meeting. She meant no harm to Anna but had a deep need to see her again, maybe serve her again if Anna and Julie, her receptionist could come to some arrangement.
"Call Julie in here right now"
Helen did as directed and a couple of minutes later the door unlocked, Julie came in and locked the door behind her. She ignored Helen, walked over to Anna, shook her hand and said that it was an absolute honour to meet her properly.
Anna looked at her, a young lady, maybe just nineteen, dressed in a simple skirt and blouse and heels. She asked Julie how she had met Helen and how she had found herself in charge of her.
Julie explained that she had started here on work experience, firstly just delivering mail. She came from a tough background but was trying to make her life better. It did not take long for Helen to notice her and pay attention to her. Maybe she saw a new Cherry in her. Over time and some private chats and learning they were where they were today. Though Julie was no where as tough on Helen as Cherry had been. |
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Great story, keep it going. I hear that some people are complaining, I truly fail to understand the mentality of some people |
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Please do continue, you write so well. Ignore the doubters. |
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By (user no longer on site)
over a year ago
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By (user no longer on site)
over a year ago
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By (user no longer on site)
over a year ago
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"Not much of a surprise you told us about her at the top of the forum ??
you are free to not read if you dont like the twists and turns"
what twists every one going to be the sub and he's going to suck cock and be fucked.and the Dom is going to Dom every one.its just a repeat of over and over we know he cleans and doesn't matter how much he cleans he gets punished. So there's really no twists. It's just the matter of how many more people you can add to fuck the sub.because he's running out of cleaning days |
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By (user no longer on site) OP
over a year ago
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"Not much of a surprise you told us about her at the top of the forum ??
you are free to not read if you dont like the twists and turns what twists every one going to be the sub and he's going to suck cock and be fucked.and the Dom is going to Dom every one.its just a repeat of over and over we know he cleans and doesn't matter how much he cleans he gets punished. So there's really no twists. It's just the matter of how many more people you can add to fuck the sub.because he's running out of cleaning days"
Then if it annoys you so much why are you reading. And if you read it is not all about sissy. |
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Like you said if you dont like then dont read end of ...
By the way I'm still hooked love it x |
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By (user no longer on site) OP
over a year ago
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Anna and Julie carried on talking as if Helen was not in the room, though she was still there naked and kneeling. Anna asked how much control Julie had and how it worked on a daily basis. Julie said:
"The company pretty much runs itself, there is little need for her to be here often, apart from the odd import client meeting and the monthly boardroom meetings. I am here every day as point of contact and to run interference. If she is not here she is kept naked chained at home. I moved in with her six months ago, after she begged me to. At home I pretty much have full control, though for the sake of work we are discrete. She does all the housework and has dinner ready for me when I come home. I was thinking of getting her a maid uniform but enjoy seeing the impact of her being naked around me has on her. Especially if I am dressed in denim skirt and doc martens, that makes her extra submissive. She has grown to be quite the pain slut and recently started training her to be my toilet "
Anna smiled and admitted that she was impressed and that Helen had obviously grown more comfortable and deeper in her submission. The question she had was what did they expect from her, why had Helen tracked her down and reached out? It seems Helen needed more and also felt that Anna could teach Julie a few things about domination and control, to help her understand Helen's base needs more. They were hoping Anna would act as a mentor to Julie. If she decided it was not for her they would part ways but the cleaning contract was still Anna's if she wanted it.
Anna was quiet for a few moments considering. She looked at both Julie and Helen and said:
"How far are you willing to go? If I agree to this I will want to push you both way out of your comfort zones and make sure there was no way back for either one of you. When I am finished Helen will belong lock stock to Julie and will have no say in what happens. Julie will respect me and take my advice. Is that acceptable?"
Helen moved from where she was and kissed the shoes of Julie and Anna to signify her acceptance. Julie just nodded.
Some ground rules:
"Never call me Cherry again, the name is Anna or Miss Anna depending on your stature
I have a bitch so from now on Helen is will be known as whore
Now as a sign of a sincerity and to seal the deal. Julie do you know of a local piercer and tattooist?"
When Julie confirmed that she did Anna went on:
" I want you to take whore there now. You are to get four rings inserted in her pussy lips, two either side. I want a chain connecting them and it locked so she has no access to her pussy. I want her nipples pierced. Also just above her pussy I want tattooed "whore to a chav goddess". Is that understood?"
Even just hearing Anna saying those words made whore so very wet. She pleadingly looked at Julie to agree. Julie told whore to get dressed as they had an errand to run.
Anna said she would stay and look through the contract. She told them not to be too long. |
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By (user no longer on site)
over a year ago
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This is excellent !! |
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By (user no longer on site) OP
over a year ago
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While Anna went through the contract, which was very profitable indeed and may require taking on more staff, Julie and whore arrived at the tattoo shop. Fortunately they were not very busy and a young male tattooist was able to see them straight away. When they were in his room he asked what they wanted.
Julie pointed to whore and said
"I need her nipples pierced. Also two rings either side of her pussy lips with a linking chain. I also want some words tattooed above her pussy lips. When he heard the words to be put there, he was a bit surprised. He thought he had cone across most things in his line of work. He checked that this was all agreed and whore simply stated that she was fully on board. He told her to strip and lie down on the bench.
Preparing his tools he first took hold of her right nipple and quickly pierced it and placed a silver ring through it. He then did the same with the left. He then moved down between her legs and placed the four required rings. He linked them with a chain and locked it, handing Julie the key. He finally busied himself with the tattoo. While all this was happening whore moaned quietly to herself with the pain and the knowledge that she was being permanently marked. When he was done and explained the cleaning and maintenance of the piercings and tattoo, Julie asked for something else. She asked for "Chav Goddess" to be tattooed above her own pussy lips.
When all was done Julie asked if he wanted a bonus. When he agreed and told whore to kneel and prove what a whore she was. Imagine anyone who knew her seeing the respectful Ms Jones on her knees sucking off a mid twenties tattooist. Her skills were good and did not take long for him to spurt down her mouth. Whore cleaned him off and got dressed.
When they arrived back at the office Anna was waiting. Without being told to whore stripped off to show that she had obeyed. Julie also showed Anna her tattoo, which Anna approved of. The key was given to Anna who added it to the other two on her necklace. Anna said
"I will enjoy knowing that you will give whore all the pain she needs and you will make her very wet indeed but she won't be able to do anything about it. I can only imagine how desperate she will get and what she will do to be allowed to cum."
Anna told whore to worship her boots as she discussed the finer points of the contract with Julie. Soon it was all agreed and signed. As she got ready to go she asked Julie if she kept her doc martens at work. Julie explained that she had a pair at work and at home. She was asked to put them on. When she did so whore was told to lie down on the floor and Julie placed the sole of her boot on whore's face. Anna smiled and said
"This is where you belong always, under the boot of a Chav Goddess. Don't ever forget that or try and act like you are better than us. If it was not for the piercings I would have Julie kick you on your pussy."
Whore just moaned with pleasure.
Meanwhile it had been a normal day for sissy and Princess Sara. Work matters had kept them separate for most of the day until just before leaving time. Princess Sara came into sissy's office and shut the door
"I have had a long day and need a foot massage before I head home sissy, so get to it"
As sissy was massaging her feet Princess Sara related the events of the night before and her realisation that sometimes Miss Anna would cause her pain purely because she wanted to. Based on his own limited experience and reading sissy understood that not all pain administered to him was punishment for sloppy work. Some was just to remind him of his place and for the enjoyment of his superiors. He would know when it was punishment as he would be informed as to why he was being punished. They then left for their respective weekends. |
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By (user no longer on site)
over a year ago
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Please ignore the nay sayers and continue with a well written multi strand adventure. |
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By (user no longer on site)
over a year ago
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Nice |
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great story,please keep it going and dont mind those that complain and keep reading ur great story |
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By (user no longer on site)
over a year ago
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loving this, im hooked |
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Love it. Can’t wait for the next instalment x |
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By (user no longer on site) OP
over a year ago
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While all this was going on we cannot forget about the other parties to our little story, sissy's neighbors, Jane and Jim and John.
John had been single for quite a while, having been married when younger, without kids. It was a good life but he and his wife just drifted apart and they had an almost non existent sex life. He lived in the neighborhood for 20 years and was happily retired. His first experience of using a sissy was in his twenties. By pure chance he came across a glory hole in a public toilet near him and decided to try it. After a couple of visits he met a guy in his fifties who liked to wear panties while he sucked cock. John considered himself pretty much straight but at times a mouth was a mouth and the old sissy could suck well.
Even during his marriage he would continue to seek out sissy bois to use. Their age did not matter, just their desire to kneel and suck. He got to understand that some liked to be humiliated while doing it and he was too happy to oblige. When his marriage ended he decided to stay single and fully explore using sissies. The first time he got to fuck a sissy was a very fond memory.
He was pretty aufait with online mediums, chat rooms and web sites. He answered an ad taken out by a local sissy who loved being used. After a few messages they arranged a meet. The sissy did not mind that John was new to fucking, in fact it added to the spice. On the arranged day the boi turned up at John's and was let in. As soon as the door was closed, boi dropped his coat and was wearing a black PVC shift dress. He got down on his knees and took out John's cock and started sucking it. When it was nice and hard the boi asked where the living room was. When shown in he took out some lube and a condom. Putting the condom on John, he lubed it and his ass. Bending over the couch he simply said:
"Fuck me".
Not needing a second invitation John lined up his cock with boi's hole and shoved it straight in. Thanks to the lube and the well used ass he soon slipped in balls deep and started fucking boi hard. It did not look like it was his first time but he didn't last long and was soon filling boi's ass with cum. He then collapsed on top of boi. His first but not last experience.
He first met Anna when she came to clean for him. When he found out that she owned the company he was surprised that she still did cleaning jobs herself. She explained that she often did the first one and sometimes others for special clients. He found her easy to talk to and soon was telling her about his interest in sissies and their use.
So imagine his delight when Anna asked for his help in training a local sissy. If only John had known earlier,maybe he would have got there before her.
As for Jane and Jim, they were in their late twenties, had known eachother most of their lives and thought they were settled and happy. Jim had a good job which gave them a good life but he travelled a lot with work. Jane had given up her work when they moved into the neighborhood and did not have many friends. Maybe that's why she found it easy to talk to Anna and ended up confiding in her.
The main reason for their move was that she had found out that Jim was having an affair with an office intern. A mutual friend saw Jim and the intern out one night getting rather pally and told Jane. When confronted Jim tried to deny but eventually confessed. His head had been turned by the young intern and he was lost. He promised to end it immediately and would never do it again. Jane insisted on a new job and move to a new area. She did not know when or if she would trust Jim again, especially with all his travelling but she did not want the marriage to end.
When she was talking it over with Anna she was a bit surprised when Anna first mention the idea of her taking more control. The more they talked the more she liked the idea. A while later she had a sit down with Jim and laid out new rules:
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By (user no longer on site) OP
over a year ago
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"if you want to stay married you need to earn back my trust, especially with all your travelling. I am taking more control.
I will control all the finances and credit cards
I will be controlling your social life and who you meet
Either I will be getting a maid or you will be doing more around the house
If I need to I will discipline you
Most importantly you will never leave this house without your cock being locked up.
Agree to these and we may have a chance, disagree and it's all over."
Jim was aghast at what he had heard but knew he had brought this upon himself. That stupid error with the intern would follow him for the rest of his life. He told Jane that he agreed. She told him to strip and stand in front of her.
When he was ready she knelt down and held his cock. She smacked it slightly to get it to go soft. She reached behind her and took out the package Anna had got her. She placed the ring at the base of the cock, behind the balls. She positioned the cage over the cock and locked it in place.
She then positioned a chair, sat down and pulled Jim over her knee. She then picked up her hair brush and administered a hard spanking to her errant husband.
The next time she spoke to Anna she brought her up to date. Over the next while things improved between Jane and Jim but also things changed between Anna and Jane. Jane found herself feeling submissive towards Anna and wanted to please her. Being able to recognise the feelings it did not take Anna long to go from Anna to Miss Anna and have Jane as her bitch.
When Anna surprised her by announcing that she had found a sissy maid to help Jane around the house, someone who lived next door, Jane could not believe it. It gave her an outlet for her anger at Jim that she could not bring herself to take out on him. She had less feeling for the sissy but took care not to overdo as sissy was Miss Anna's property.
Jane was happier but needed a new challenge, a new outlet. |
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By (user no longer on site) OP
over a year ago
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Saturday morning Miss Anna contacted bitch and told her to meet her at a local restaurant at one. Bitch was told to wear a nice dress and heels but no underwear. When she arrived Miss Anna was already there, dressed similar so it gave the impression of two ladies out for lunch. They had a nice meal and some general chat. Miss Anna told bitch about the new contract and about her first bitch tracking her down. This just demonstrated Miss Anna's power to bitch even more.
When they were finished lunch bitch was told they had an appointment at the tattooist. The idea scared bitch but even in this short space of time she was too far gone to back down. When they arrived they were seen by a female assistant. Miss Anna removed the chastity belt and asked for six rings to be inserted in bitch's pussy, three either side. Having seen the look on whore she much preferred this as as form of chastity. Three padlocks were placed between the rings locking them together. She also asked for the words "Anna's bitch" to be tattooed just above the pussy lips.
When the tattooist was done and bitch was wrapped up they headed back to Miss Anna's. In the basement bitch was stripped and strapped face up to the spanking bench. Miss Anna undid the padlocks and got out the magic wand. She strapped it in place so the head was right on bitch's pussy lips, which were a bit tender. She put the wand on a medium setting so it would give bitch pleasure but not enough to get her off. She left bitch like that for an hour just teasing her.
Miss Anna then took off her dress and put on her strap on and inserted a dildo into the harness. She unstrapped bitch's legs and placed herself between them. Being a lot more gentler than the last time she fucked bitch, she pushed the dildo into bitch's pussy and started to rock forwards and backwards. The hour's teasing had the desired impact and bitch was primed and on edge. Miss Anna would take bitch so far and then withdraw, let her cool down and start all over again. Bitch was crying with frustration and was begging Miss Anna to let her cum.
"Please please please let me cum Miss Anna please. Stop teasing"
Miss Anna replied
"Who is me, who are you, who owns you"
"I am your bitch, you own me and I am here to please you. Please let your bitch cum"
Miss Anna upped the tempo and finally took bitch over the edge, letting out a gutteral scream as she squirted all over the bench.
"You will be cleaning that later bitch"
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By (user no longer on site) OP
over a year ago
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Later that evening sissy arrived at the adult store to prepare for his night out. This would be his first visit to a BDSM event and remembered Princess Sara's tales of her visits. Miss Marie let him in and told him to strip completely. She removed the plug from his ass and replaced it with a bigger one, but one that also vibrated. She also added a vibrating cock ring at the base behind the cock cage. Looks like sissy was in for another torturous night. Miss Marie then dressed him in the catsuit again, covering his whole body and face. She added chains between the ankles and knees. Finally she placed a large ring gag in sissy's mouth. She leashed him in the shop while they waited for Amy to arrive.
When she did get to the store Miss Marie told her to strip. Using lube she placed a vibrating butt plug in Amy's ass and a remote control egg in her pussy. These were kept in place locked between her legs. Amy was then given a slave harness to wear, which was basically straps across her body, with her tits and pussy on show. Her arms were placed in a single leather glove that was strapped behind her back. The outfit was finished with a posture collar and leash and a ring gag. Amy was leashed beside sissy while Miss Marie went to get ready. When she came back she was dressed in a leather catsuit and leather boots. She put cloaks around Amy and sissy and gave sissy a bag to carry. Taking up the leashes Miss Marie led her two toys to her car for the drive to the club.
When they got there she gathered the leashes and led the toys into the club. There were plenty of people dressed in PVC, leather and latex. A good mix of dominants and submissives, of both sexes. Inside the club itself there were waitresses in full PVC french maid uniforms walking around with trays of drinks and snacks. Both Amy and sissy were gob smacked by what they were seeing. As Miss Marie led them around they could see various areas cordoned off for different types of play, some for boot and foot worship, some for impact play, some for sex play. As if she knew where she was going Miss Marie headed for one particular area.
When she got there it was a small alcove with two inserts in the walls. She placed Amy in one and sissy in the other. Chains were added to their collars to keep them in place. Taking the bag she took out two funnels and placed one in each of the ring gags. Turning to the crowd she announced:
"Ladies and gentlemen I am pleased to announce that the public human urinals are now open for business. They are available for use by men, women or in-between, for liquid release only. To make it more enjoyable this is a first for the toilets. Their previous experiences have only been on a one to one basis. They will be in place for two hours and I hope they get a lot of use."
Neither Amy or sissy were expecting to be used in this way but knew it was within the limits they had agreed with Miss Marie. Before they could think much about it a male and female couple took their places to use the toilets. Soon piss was spilling down the funnels. |
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By (user no longer on site)
over a year ago
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This is great mmmm |
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By (user no longer on site)
over a year ago
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By (user no longer on site) OP
over a year ago
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For those who may be new to the story a quick intro to the main characters so far:
Sissy a mid 50 yr old guy who lives alone and works in an office. Keeps to him self and has been a hidden sissy for many years. Recently caught in a compromising situation and initially forced to be more of s sissy and undergo training. Has come to enjoy the freedom to explore his true self.
Anna a mid 20s ex chav previously known as Cherry. After realising the power she had over people turned her life around and runs a successful cleaning business, with special services for special clients. She is enjoying taking sissy deeper into his submission.
Jane and Jim, late twenties married couple, neighbors of sissy and clients of both of Anna's services. Jim is in chastity and Jane uses sissy as a maid once a week and sometimes to take out her anger at men. She is also one of Anna's bitch toys.
John a 70 yr old neighbor of sissy and user of Anna's cleaning services. Long term sissy user and currently helping in sissy's oral training.
Sara an early 30s co worker of sissy who discovered his sissy side by chance. After talking with Anna, to sissy she is now Princess Sara who keeps an eye in sissy at work and uses him as a maid once a week. To Anna she is her tattooed pierced bitch toy.
Marie a late twenties woman who works at the local adult store. Helps Anna with supplies and enjoys helping train and use Anna's various bitches.
Amy and Lucy two young friends of Marie. They have briefly explored kink and Amy is the more adventurous of the two.
Ms Jones a mid 60s very successful business woman who was Cherry's first female bitch. Tracked Anna down to engage with her again and ask her to help mentor Julie, her new chav Goddess. Now tattooed and pierced but is there more to her. Now known as whore.
Julie a mid 20s chav who started work experience in Ms Jones company and soon grew into being her new owner. Being mentored by Anna or does she have other plans.
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By (user no longer on site) OP
over a year ago
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Miss Anna got up walked to a drawer and took out some string. Being careful not to be too harsh she attached some to each of the rings in bitch's pussy. She then tied off the other end to the sides of the bench, forcing the pussy lips to stay open. She positioned the wand in place again and put it on the top setting.
"Enjoy yourself bitch while I go have a bath. Will be back at some stage."
As bitch was rather tender it did not take long for the wand to get frustrating rather than pleasurable. Strapped as she was there was nothing she could do to stop it, just hoped that Miss Anna did not take too long.
Miss Anna went upstairs, ran a hot bath and relaxed in it for over an hour. As she soaked she wondered how sissy and Amy were getting on. She did not know the full details of what Marie had planned, just that the toys would be well used. She got out of the bath, dried off and dressed in a silk negligee and nightgown and went back down to the basement.
When she arrived bitch was struggling against the straps trying to dislodge the wand. By doing this she pulled on the strings attached to her piercings which added to the torture. By the mess under her she had obviously cum a couple more times. Miss Anna approached, turned off the wand and put it to one side. She undid the straps and string and helped bitch up. She put a collar and leash on her and forced her to her knees.
"Look at the mess you have made of my bench. Lick it clean and let me tell you if you don't do a good job I will flay your skin like never before".
In the post orgasmic bliss she was in the last thing bitch wanted to do was clean her mess off the bench. However she was in no mood to be beaten so she stuck out her tongue and started to lick. She had never tasted her own juices before and was not sure she liked it. It took her a good half an hour to clean to Miss Anna's standards and her knees and tongue were sore.
When she was finally done Miss Anna led her over to the standing cage and placed her inside. Using chains she attached bitch's arms and legs to the bars of the cage. She then went to a nearby telephone and rang someone.
"Julie hey there it's Anna I was wondering if you and whore were free if you wanted to come over for a chat and some lessons. If so I will see you about 9. Here is the address" |
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By (user no longer on site) OP
over a year ago
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Back at the club Miss Marie was enjoying watching the two toilets being used. Since they were opened fit business they had a constant queue of people wanting to use their mouths. To make it more interesting Miss Marie was randomly setting off the vibrators in the toys holes, sometimes making them jump.
She had previously used Amy as her toilet as part of their exploring. She knew that Amy had a fantasy about being used by multiple people, especially those who did not know her and only saw her as a toy. Miss Marie could only imagine how wet Amy's pussy was at this use especially with the use of the egg. As for sissy he could be used in any way Miss Marie wanted as long as it did not go against the limits agreed with Anna. With the use of the plug and cock ring she could only imagine how sore sissy's cock was in his cock cage.
All two soon the two hours was up. Miss Marie let the last two finish and then she removed the funnels and unchained the toys. Gathering the leashes and the bag she led the toys to a social area so they could sit and relax. She removed the ring gags and fed the two toys some water.
"I appreciate that was unexpected but I have to say I am proud of you both. You both performed very well and the people using you were very pleased."
Miss Marie called over two of the PVC clad waitresses and whispered something to them. Each one of them took a leash of each of the toys and led them off somewhere. When they arrived the toys were relieved that they had been taken to the toilets, proper toilets. They were taken into the respective cubicles and the maids helped them relieve themselves. The maids tidied up the toys and led them back to Miss Marie.
When they were reunited Miss Marie led the toys to a cordoned off area that held a St Andrew's Cross. She leashed sissy to the side of it and placed the bag in his hands. She undid the sleeve holding Amy's arms and let her get some feeling back. She then strapped Amy face down to the cross. She took a flogger out of the bag and started to flog Amy's back and ass. After she warned up she replaced the flogger and took out a paddle. Concentrating on the ass she started paddling hard. At the same time she hit the remotes on the toys in Amy's pussy and ass. As Amy's ass got redder and redder she was moaning with a mixture of pleasure and pain. Miss Marie took a break for a moment to set off the toys in sissy, putting them at the highest level possible. It was amusing to see him twitch.
Finally Miss Marie put away the paddle. She massaged Amy's red ass and whispered "well done" in her ear. She unstrapped her and helped her down. Taking a towel from the bag she placed it over Amy and led her back to the social area. She asked one of the passing maids to collect sissy and bring him along. The maid dropped a curtsey and said it would be her pleasure. |
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By (user no longer on site) OP
over a year ago
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Julie asked if there was any salt. When the answer was there was in the kitchen she politely asked Miss Anna if she could get her some. Not being used to ask to fetch things in her own house Miss Anna was taken aback but said nothing. When she returned with the salt Julie took some and rubbed it on whore's ass, making whore sting.
She then stepped back and delivered the next ten strokes in rapid fashion, making sure to land as many on the same spot as possible. Asking how many were left, whore replied
"Five more thank you Goddess Julie"
Miss Anna was surprised at this form of address but considering the phrase she had whore get tattooed on herself she guessed it made sense. For some reason it made her shiver.
Taking her time Goddess Julie administered the last five strokes, taking time with them and making each one count. When she was finished whore was flat against the cross and shaking. Goddess Julie walked around the front, held up the cane and made whore kiss it. This action made Miss Anna wonder how inexperienced Julie was (she would never call her Goddess).
Miss Anna walked over and released bitch from the cage and told her to make coffee. She led Julie up to the living room where they could relax and talk. After coffee was delivered Miss Anna told bitch to get on all fours so she could use her as a foot rest. As she relaxed she asked Julie about her kink experience.
Julie smiled and said that she had done some exploring and reading especially since been introduced to Anna. She knew that whore got off on the difference in their public standing and was maximising that difference. Her choice of outfit for tonight was most deliberate and if she could she would wear it to work to continually remind whore. |
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Loving the story with it's many scenarios and characters. Is there a piece missing between Miss Anna inviting Julie over and Julie asking for salt? Just wondering |
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By (user no longer on site) OP
over a year ago
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"Loving the story with it's many scenarios and characters. Is there a piece missing between Miss Anna inviting Julie over and Julie asking for salt? Just wondering "
Well spotted. Unfortunately last cut and paste did not work properly. Will see if can recreate |
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By (user no longer on site) OP
over a year ago
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revised latest update
Promptly at nine there was a ring at the door and when Miss Anna answered she found Julie standing there, dressed like a complete chav. She was wearing a teeshirt, denim skirt and doc martens. Behind her on her knees was whore dressed in a very expensive silk dress and high heels. The difference in their outfits helped to emphasis the difference in standings between them. As Miss Anna let them in she could not help but look Julie up and down, hoping no one noticed the impact her outfit had on her. She led Julie down to the basement with whore following behind on all fours.
Julie was amazed at the array of equipment and toys in the basement and at seeing bitch chained naked in the cage. She ordered whore to crawl over and kiss her martens which was immediately done. She then asked for a scissors and told whore to stand. Without warning she started to cut the dress off which led to a gasp from whore as she remembered how much it had cost. Soon it was in pieces at her feet and she was told to get on all fours and using her mouth crawl and deposit the dress in the bin. This took her six trips.
When she was finished Miss Anna told whore to lay against the cross and she showed Julie how to strap her down, making sure to check they were not too tight. Knowing what a pain slut whore was Miss Anna walked over and picked up a thick cane. She showed Julie where to hit and how to stand to get the best effect. Before she started Julie asked whore how many she should get. Wanting to impress both Julie and Miss Anna whore replied “30 strokes”.
Surprised at the reply but happy to oblige Julie walked behind and administered the first five strokes very rapidly. They found their mark and left stripes across whore’s ass and made her gasp. Before carrying on she walked over and ran her fingers down whore’s pussy lips and was not all surprised to find them soaking. Taking a step further back Julie administered the next ten as hard as she could, trying to get accurate and hit in the same place. Bitch could only look on at amazement at the beating whore was taking.
Julie asked if there was any salt. When the answer was there was in the kitchen she politely asked Miss Anna if she could get her some. Not being used to ask to fetch things in her own house Miss Anna was taken aback but said nothing. When she returned with the salt Julie took some and rubbed it on whore's ass, making whore sting.
She then stepped back and delivered the next ten strokes in rapid fashion, making sure to land as many on the same spot as possible. Asking how many were left, whore replied
"Five more thank you Goddess Julie"
Miss Anna was surprised at this form of address but considering the phrase she had whore get tattooed on herself she guessed it made sense. For some reason it made her shiver.
Taking her time Goddess Julie administered the last five strokes, taking time with them and making each one count. When she was finished whore was flat against the cross and shaking. Goddess Julie walked around the front, held up the cane and made whore kiss it. This action made Miss Anna wonder how inexperienced Julie was (she would never call her Goddess).
Miss Anna walked over and released bitch from the cage and told her to make coffee. She led Julie up to the living room where they could relax and talk. After coffee was delivered Miss Anna told bitch to get on all fours so she could use her as a foot rest. As she relaxed she asked Julie about her kink experience.
Julie smiled and said that she had done some exploring and reading especially since been introduced to Anna. She knew that whore got off on the difference in their public standing and was maximising that difference. Her choice of outfit for tonight was most deliberate and if she could she would wear it to work to continually remind whore.
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By (user no longer on site) OP
over a year ago
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At the club Miss Marie decided there was time for one last bit of fun before they left. She reattached the two ring gags and put Amy's arms back into the single sleeve. Taking up the leashes she led the two toys to another cordoned off area. Having them kneel and attaching chains to keep them in place. She upped the four vibrating toys to their highest levels. The ring gags held their mouths level with the glory holes in front of them. Soon a cock appeared in each hole and they were encouraged to suck. As with the toilet use they quickly had a queue of cocks waiting to use their mouths.
Not wanting to be left out Miss Marie summoned a young maid and whispered something in her ear. With a smile the maid knelt down in front of Miss Marie, undid the dual zip on her catsuit and started to lick her pussy and clit. It was torture for Amy to see someone else pleasure Miss Marie as she herself was being regularly face fucked. She was more fortunate than sissy as her private parts were not trapped behind a chastity device. Sissy's cock had been in absolute torture all night especially with the addition of the vibrating cock ring.
After losing count of the number of cocks sucked and a few most enjoyable orgasms for herself, Miss Marie called an end to the proceedings. She thanked the maid, released the two toys and led them back to her car. Considering how late it was she decided to bring the toys back to hers for a few hours sleep. When they got to her place, she placed sissy in a dog cage in her garage. She did remove the ring gag before leaving him to rest.
Amy was taken to Miss Marie's bedroom. The ring gag and sleeve were removed and a chain linked to the posture collar. After Miss Marie had stripped out of the catsuit, they collapsed in the bed together and slept.
When they eventually woke they spoke about the night's experience and how much Amy loved it. She told Miss Marie about being jealous of the maid who had licked her to orgasm. Miss Marie smiled and said
"You will have plenty of chances to do that slut"
She then left Amy chained to the bed so she could go release sissy and let him get changed and leave. Herself and Amy spent what was left of Sunday having more fun. |
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By (user no longer on site)
over a year ago
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Really great read !!! |
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By (user no longer on site)
over a year ago
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Stunning |
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By (user no longer on site) OP
over a year ago
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As the two ladies chatted from her position as foot stool bitch could pick up the tension in the room. She did not know why but she got the impression that Miss Anna did not like Julie, maybe was even a bit scared of her. But that could not be the case as bitch could not imagine Miss Anna scared of anyone. If bitch knew more about Miss Anna's background maybe she would understand.
The chat came to an end and Julie went downstairs to fetch whore. As Julie had destroyed her dress whore was given a cheap coat to wear home. When they went bitch was told to get dressed and leave as well. Miss Anna needed some time alone.
On the drive back home Julie and whore talked about how the night went and Julie's impressions of Anna. Unknown to Anna Julie was fully aware of her upbringing and changes in her circumstances. The chav outfit Julie had worn did have a dual purpose and Julie had noticed the effect it had on Anna when they first arrived.
Over the next month everyone went about their normal routine. Sissy spent every Tuesday at Miss Jane's, every Wednesday at Princess Sara's and every Thursday at John's. His cleaning improved but was still subject to pain from the two ladies if they wanted to. In the privacy of his place and with more time and room John often face fucked sissy three times before letting him leave.
Work was busy for sissy and Princess Sara and they did not get much time together. Sissy did arrive each morning with coffee for Princess Sara and she always checked he was caged, plugged and pantied. On the odd occasion she managed to get a foot massage off him. Both were finding it difficult having to keep their inner sides hidden.
There had not been much contact with Miss Anna who had said that preparing for the new contract was going to keep her busy for a while. Twice during the month bitch got a late night summons. On both occasions the sessions entailed bitch enduring a hard impact session and a hard strap on fucking. Miss Anna did reveal to bitch that in the near future she was going to take her anal cherry.
Miss Marie was kept busy in the shop and with training Amy. They had paid another visit to the club, where Miss Marie called in a favour. This allowed Amy to spend the night as one of the PVC french maids. She spent the time serving drinks and snacks, helping bound guests to the toilet and giving the odd blow job. She ended it on her knees licking out Miss Marie as she had seen the maid do on her first visit.
As for the new members of the story, Julie and whore. They were, like Miss Anna busy preparing for the new contract. A day did not go by that whore was not wearing some stripes or bruises from pain lovingly inflicted by Julie. She had also become very adept at drinking Julie's piss without spilling any.
At the end of the month an invite went out to a get together at Miss Anna's. She had something important to discuss. She requested that sissy, Amy and whore were to serve as maids for the night, in uniform. She also requested that Julie, Sara, Marie and Jane wore an outfit suiting a professional preferably in black and white. |
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By (user no longer on site) OP
over a year ago
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The day of the meeting arrived. Miss Anna dressed in a white silk blouse, black leather skirt and knee high boots. First to arrive were the three maids. As sissy and Amy had never been before Miss Anna gave them a quick tour and noted their reaction to the basement. She then showed all three where the drinks and food stuff was and the glasses and trays. She took them to the spare room and told them to strip. As a uniform whore was given just an apron and high heels. Sissy was given a cheap Ann Summers uniform that just about covered his caged cock. Amy was given a proper English maid uniform with an over the head apron. They were then set to work.
Next to arrive was Sara, dressed in a black business suit with white blouse and heels. Next was Jane in a simple black dress. When Marie arrived she was wearing latex trousers and a latex blouse. Last to arrive was Julie, who took the easy option with the dress code, white tee shirt and black denim skirt and her doc martens.
When they all had drinks and the maids were standing against the wall, Miss Anna got up to speak.
"Thank you all for coming and mostly making an effort with the dress code, looking at Julie. I appreciate that you don't all know each other but I do so will quickly introduce:
The lady in latex is Marie who works in the local adult store and has been of immeasurable assistance to me with one of my businesses and the young maid in the full uniform is her pet Amy.
The lady in the dress is Jane one of my clients and the lady in the business suit is Sara. Both of them are helping me in training sissy (it's obvious which one is sissy lol) and both of them are also my bitches (this was no surprise to Jane or Sara as they knew Miss Anna was not exclusive.
As for the other two they are partly the reason we are all here today. The maid in the apron is whore and while she may not look it she is a very successful property management company owner. Our last guest is Julie her receptionist and owner."
This last bit brought a gasp from everyone else in the room.
"Whore was my first female bitch when I started off as a cleaner. She was wealthy even back then but I caught her masturbating to the idea of me mistreating her. For a while I gave her what she wanted. Recently for reasons of her own she tracked me down and made a suggestion. At a recent business meeting she presented two proposals to me. One was to mentor Julie and the other is why we are here.
As most of you know I have two businesses, a successful cleaning business and special services for certain clients. Through these I got to meet all of you. I now want to combine these in a new way and need your help.
Once I have outlined my idea you can keep our reliable as it currently is with no hard feelings or you can join me in the venture"
Miss Anna then ordered the maids to refresh drinks before carrying on. |
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By (user no longer on site) OP
over a year ago
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The next proper installment of this story will take it over 30000 words. I wanted to say thanks to those who have stuck with it and commented.
Apologies for the odd spelling error- normally typed on phone when have spare moment and copied and pasted over |
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By (user no longer on site) OP
over a year ago
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[Removed by poster at 27/02/20 17:55:28] |
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By (user no longer on site) OP
over a year ago
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"And the big surprise Miss Anna turns submissive "
Are you just jealous or something? Your last forum posts got less than five replies so you like spoiling things for others?
Sad life |
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By (user no longer on site)
over a year ago
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"And the big surprise Miss Anna turns submissive
Are you just jealous or something? Your last forum posts got less than five replies so you like spoiling things for others?
Sad life"
 |
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Stacy, I challenge you to put down your donut and write a story yourself |
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By *ubsteffTV/TS
over a year ago
Portsmouth |
[Removed by poster at 27/02/20 20:52:32] |
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By *ubsteffTV/TS
over a year ago
Portsmouth |
This is a quality story & I’m loving it! |
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By (user no longer on site) OP
over a year ago
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When the drinks were replenished Miss Anna continued:
"Thanks to whore my company has been offered a very large and profitable cleaning contract for the properties her company owns. This is going to require more staff so I had the idea of setting up a maid/cleaning recruitment and training company. Why pay someone else to do what I believe we can do in house. When the idea came to me I thought of you and how you may play a role in this.
I appreciate that you may worry that our current relationships may make working together difficult but I think it will just enhance them. If you decide to accept there will be fully separate legal contracts in place guaranteeing your salaries, rights etc and to make sure any kink adventures cannot be used against you.
Sara I thought you may like the role of head of customer relations, I know how professional you are and how good you are with people. I also thought you could manage the finance department as well.
Jane I thought you may like head of training. I know you enjoy training sissy and his skills have improved, though you may have to limit your discipline methods.
For you sissy I had the role of Sara's assistant in mind. You would make a great PA and you would be a role model for the new maids, some of whom may well be sissies like you. Of course the role would come with appropriate uniforms more befitting your status.
Marie I would like to use you and your contacts for our uniforms and accessories that may be needed for any new special clients we may acquire.
Amy you seem like a nice young lady with a good head on your shoulders and a good work ethic. I thought you may like to come aboard as one of our new maids.
The new company will have a board of directors made up of me, Sara, Jane and Julie.
What does everyone think? I appreciate it is a lot to take in."
Suddenly there was a lot of chatter and questions as every one took in what had been said. |
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By *ed01Man
over a year ago
happy ville |
Need my house cleaned !!@ |
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By (user no longer on site) OP
over a year ago
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Miss Anna addressed the gathering again:
"Enough serious business talk. I don't need your answers just now. I will give you a few days to think about it all and let me know. Now let's have some fun. As you all know though not all of you have experienced it, I have a very nice dungeon kitted out below. Give me a few minutes to set something up and please join me down there."
As she left she took sissy with her. When they reached the dungeon sissy was ordered to strip and lay across the spanking bench. He was securely strapped down and a blindfold put in place. A large ring gag was also added and his butt plug was removed. When she was happy Miss Anna donned a strap on with a large dildo in it. She had other harnesses and dildos laid out.
When the others joined them she explained what was going to happen.
"Ever since I took over sissy's life I have been training his ass to prepare it for my dildo and eventually real cock, like a proper sissy should take. I have decided that tonight is the night to take his anal cherry. I thought you may like to join me so have laid in extra harnesses and dildos for anyone to use. That includes Amy and whore to remind sissy that he is under all women."
At these words sissy struggled against his restraints but knew of course he was going nowhere. He knew this day would come but had not expected it tonight. Maybe that's a good thing as less time to worry about it.
Miss Anna walked around to the front of sissy and stuck her dildo through the ring gag.
"Let's see if those hours of training and pleasing John have worked sissy. Better suck well as you know where it is going"
Sissy started to suck on the dildo, quite surprised at the size of it though he could not see it. Suddenly it was withdrawn and Miss Anna applied some lube. She positioned herself at the back of sissy, held his hole open and in one shove pushed the head of the dildo in. Through the ring gag sissy let out a scream. Pushing harder Miss Anna got as much of the dildo in the sissy ass as she could. Once happy she withdrew and shoved it back in harder. She soon built up speed and was fucking as hard as she could. Before sissy could scream again another dildo had entered his mouth, this time worn by Princess Sara.
For the next hour and half sissy's mouth and ass were spit roasted by a succession of women wearing strap ons. As soon as one left a hole it was replaced by another. Not knowing if they were going to get a chance again even Amy and whore took up the option to fuck sissy. By the end of it his hole was totally and utterly broken in.
Miss Anna replaced his butt plug when the last dildo withdrew.
"Thank you ladies for helping me show sissy his place and hope you enjoyed. Let's leave him to recover. But the fun does not have to stop". |
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great story thank you for telling,xx |
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"great story thank you for telling,xx"
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By (user no longer on site)
over a year ago
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By (user no longer on site) OP
over a year ago
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As sissy recovered on the bench Miss Anna told whore and bitch Sara to strip and stand facing eachother. When they were in position she got some small links of chain. Using them she linked the piercings on the pussy lips. This meant if one moved they pulled the rings of the other. She picked up two canes, handed one to Julie and went to stand behind bitch. Julie got the idea and took her place behind whore. In tandem they started striking the respective asses in front of them, making whore and bitch jump and pull on the rings.
Not to be left out Miss Marie told Amy to strip and strapped her down to the cross. She offered to use Amy to demonstrate various tools to Jane, who was happy to accept. Miss Marie started off with floggers on the back,ass and legs. She then passed it over to Jane to try. While the flogging continued Miss Marie picked up some nipple clamps and placed them on Amy's nipples, making her wince. She then walked back and picked up a paddle, something Jane was well used to using and having used. She picked one up as well and the two of them went tandem on Amy's ass, taking one cheek each.
As sissy tried to recover on the bench all he could hear was the sound of various implements hitting skin and various screams and winches. His caged cock was tight and in torture with the sounds and the treatment he had received earlier. He wondered how long it would take for his ass to recover.
Meanwhile Miss Anna and Julie decided to swap places and carried on caning each others bitches. They decided that they could get harsher and soon welts were appearing on the asses of whore and bitch. Neither Miss Anna or Julie wanted to be outdone by the other.
Miss Marie asked Miss Anna if she could use bitch Jane to which permission was given. Jane was ordered to strip and get down on her back. She was told to position herself between Miss Marie's legs and take down the zip in her trousers (Miss Marie always had dual zips built into trousers and catsuits for easy access). As Miss Marie carried on torturing Amy Jane was to lick her pussy. This was not easy as there was constant movement but Jane tried her best. |
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By (user no longer on site)
over a year ago
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Mmmmm |
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By (user no longer on site) OP
over a year ago
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Shortly after that Miss Anna brought the evening to an end. She left sissy strapped to the bench but put a blanket over him. The others gathered their clothes and made their way upstairs. Everyone thanked Miss Anna for the evening and promised to think over what she proposed. When alone Miss Anna quickly crashed in bed.
Over the next few days most people had a lot to think about and whether or not they wanted to change their lives around, in particular Princess Sara and sissy. They currently had well paid jobs though both agreed it would be nice to be able to be more open about their new selves at work and Princess Sara in particular liked the idea of having more control over sissy as her assistant.
Amy was not sure what to do either. She felt that people were misjudging her and not taking her for as clever as she was. She felt that she was capable of being more than just a cleaner. She had long discussions with Miss Marie before reaching her decision.
Jane discussed the options with Jim though these days he had little say over what she did especially as he was not around much. She needed something to do but was not sure whether this was it or not.
Before anyone made their mind up they got an update from Miss Anna. The new company was not being set up but instead there would be a training department within her existing company. This meant changes to the offers to Sara, Jane and sissy. Sara would come on board Miss Anna's personal assistant and help with customer relations. Jane would join the existing training department as a new trainer. Sissy would still be Sara's assistant and also cover reception duties. There would be no new seats on the board of directors.
At the end of the week all concerned parties contacted Miss Anna and let her know of their decisions.
Amy declined the offer, explaining that she had felt undervalued by it though she knew it was a starting step. She had decided to work at the adult store with Miss Marie with the aim of one day running it together. This also gave her a chance to continue her training as Miss Marie's pet. Both would still be happy to help Miss Anna when they could.
Next was Princess Sara who agreed as long as sissy did. She knew by doing so she would be more under Miss Anna's control but having released her bitch side she did not want to hide it. Thankfully for both of them sissy also agreed. He knew that this would be pushing him further down the sissy route and more people would know but it is what he wanted. With taking leave they were due they both had two weeks notice to serve before they could start.
Finally there was Jane who also agreed but had what may be considered a strange request. She wanted to start as a cleaner and go through the current training programme so she could see what changes were needed.
With all this agreed Miss Anna suggested that herself, Sara , Jane and sissy go out to celebrate over dinner, at a private club she knew.
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By (user no longer on site) OP
over a year ago
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It was Amy's first day at the shop and she was nervous. She had no idea what to expect but was looking forward to het first proper job and knew that she would have Miss Marie to look after her. She was told to arrive early to get ready before the customers arrived.
When she got there Miss Marie introduced her to the owner who welcomed her on board. She was then taken through the normal staff rules and given a proper tour including the glory hole and video booths. Then Miss Marie took her to get ready.
First she was told to strip completely and was then given a remote control egg to insert in her pussy. Vibrating nipple clamps were then attached. Without any underwear she was helped into an all in one PVC catsuit, which covered her from head to toe. Ballet boots were added to her feet and bondage mittens added to her hands. Finally another hood was placed over the hood of the catsuit which only had two small holes under the nose and a gauze over the eyes, meaning very little could be seen.
Miss Marie helped her to the window at the front of the shop where there was a vertical pole in place. She was placed against the pole and chains attached to the boots and mittens keeping her in place. The last thing was a strap which went around her forehead and forced her head straight against the pole. She had been turned into a human mannequin on display for all who walked by.
When she was in place Miss Marie opened the shop and they were soon busy. As the shop allowed a bit more than other similar shops in the area they were always quite popular. Not that Amy could see much from her position in the window. She could make out some noise but not much. Every now and then Miss Marie would set off the egg and the clamps, making Amy jump slightly. She tried to keep the noise down as did not want people to know she was human.
Miss Marie wondered how Amy would feel if she knew one of the customers in the shop that morning was Lucy, but not as Amy woukd remember her. Lucy was dressed in a short black leather dress and was wearing knee high leather boots. Following her around like a lost puppy was a guy in his forties, in a business suit. He seemed very embarrassed to be there but kept a respectful distance behind Lucy and listened carefully to what she said and took whatever she told him to hold. When they got to the till Miss Marie was not at all surprised to see the guy pay for everything without a word of complaint. Pulling Lucy aside for a moment Miss Marie asked what was going on. Lucy smiled and just said that she had found herself a little pet who liked to treat her well and worship her. Miss Marie wished her luck. |
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By (user no longer on site) OP
over a year ago
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"All good fun thank you"
Glad you enjoy |
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By (user no longer on site)
over a year ago
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Shop mannequin mmmmmm |
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By (user no longer on site) OP
over a year ago
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The night of the meal out came and the four met at the address given to them by Miss Anna. Both Miss Anna and Jane were dressed in white blouse, white jodhpurs, black riding boots and black riding jacket whereas Sara and sissy were dressed more casually. Before they went in Miss Anna explained that this was an exclusive club that only entertained couples, who had to consist of one dominant and one submissive. They also had a very strict dress code and protocols in place.
When they got in they were met by a burly looking bouncer in a dinner jacket. He greeted Miss Anna like an old friend and asked who her companions were.
"This is Miss Jane, the other lady is bitch who will serve as Miss Jane's submissive for tonight and finally we have sissy who is my submissive for the night. "
This came as a surprise to bitch and sissy, especially bitch who was not sure about being under the control of Miss Jane. The bouncer looked at bitch and sissy and explained that they did not meet the dress code. He told them both to strip immediately. One look from Miss Anna and they obeyed. When they were naked the bouncer approached with a linked chain set. Cuffs went around the ankles, wrist and neck and they were all linked together. Sissy and bitch were told to get down on all fours and leashes were handed to Miss Anna and Miss Jane. The bouncer said
"In here pets don't walk or talk or they get punished".
The inner doors were opened and they went in. There were many people inside, the dominants all dressed up and the pets all naked and chained. Dominats and submissives were of all different sexes. There were also club staff walking around serving, wearing nothing but collars and aprons.
One of the staff led the ladies and their pets to a booth where they could see out what was going on around them. The two ladies sat and the two pets were leashed to pegs under the table. The ladies ordered drinks and dog bowls of water were placed in front of the pets. This was not what bitch or sissy expected as a celebration meal out. But nothing was ever really normal since Miss Anna came into their lives. |
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By (user no longer on site)
over a year ago
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Gets better and better |
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By (user no longer on site)
over a year ago
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Great story  |
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By (user no longer on site) OP
over a year ago
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Meanwhile back at the shop they closed for half an hour for lunch which gave Miss Marie time to release Amy from the window. She was taken to the staff room, stripped and given some refreshments. She explained that it was quite a weird experience, been able to hear but not really see or speak. She was surprised when Miss Marie told her about bumping into Lucy and Amy thought that they needed a catch up.
When refreshed Amy was given a PVC skater dress to wear with ankle boots and collar and cuffs. Her job for the afternoon was to help out in the shop, tidy up and if Miss Marie needed her to demonstrate any toys for customers. The shop prided itself on its extra customer services. Amy enjoyed walking around and seeing who came in and what they looked at and bought. The shop attracted a whole range of people, some nervous, some joking, some confident and range of ages. A lot of it was eye opening to Amy.
At this time of the day it was mainly old men who came in looking at the porn videos so Amy was just tidying stock. Then a young couple came and nervously looked around. Miss Marie approached and asked if she could help. They explained that this was their first visit and wanted some simple bondage toys but not sure what was available. Miss Marie led them to the bondage section and explained various things to them, from leather to metal. She called Amy over to demonstrate. She said
"As you can see my pet is wearing a simple leather collar and wrist cuffs. If you want to restrict further you can use links or chains."
Miss Marie took up a double ended snap hook and linked Amy's wrists behind her back. Taking another one she linked the wrist cuffs to the d ring at the back of the collar. This lifted Amy's arms out of use but also pushed out her tits under the dress. The couple were impressed and then asked about things to add a mixture of pain pleasure. They were led over to the BDSM section where first Miss Marie picked up some nipple clamps on s chain. She attached one to Amy's left nipple under the dress, brought the chain up through the d ring on the collar and then attached it to the right nipple. The amount of pressure Amy felt on her tits depended on how still she kept her head.
Miss Marie then bent her over and lifted the bottom of the dress to reveal her ass. She picked up a toy called a slappy hand. One side was furry and the other hard. She rubbed the furry side along Amy's ass and then turned it over and administered five swats on each cheek. The couple gasped slightly at the sound and the marks. They thanked Miss Marie and Amy for their assistance. They decided as a starter kit to buy collar, cuffs, snap links, clamps and slappy hand. A well invested period of time for the two shop workers. When the couple left Miss Marie released Amy and sent her off to take a break. The rest of the day passed fairly quickly. At the end of the day the owner congratulated Amy on a good first day and felt that she would fit in well. |
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"Great story and good writing"
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By (user no longer on site) OP
over a year ago
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As the pets drank from the bowls the the ladies discussed what the uniforms should be going forward. For the female cleaners it would be traditional English maid uniform in black, with white collar and end of sleeves. This would be matched with a waist white apron and flat shoes. If there were any other sissy maids hired the uniform would be pink with white edging. The company logo would be sewn onto the breast pocket of the uniforms.
As for bitch when she was in professional Sara mode it would be black skirts, just below the knee, white blouse. Underwear would be various colours with matching sets of bra, panties, stockings and suspenders. Heels would be five inches minimum.
Sissy's assistant uniform would be a lovely pink dress with frilly sleeves and a big white sash across the middle. Like with bitch his underwear would match and be finished off by white Mary Jane shoes with a three inch heel. There would be no need to hide his sissy side at work anymore so why not fully celebrate it.
Under the table neither bitch or sissy were too enamoured with the sound of these new work uniforms.
Just before dinner was served Miss Anna asked Miss Jane to take the two pets for a quick walk, which she was happy to do. Truth be told she enjoyed strutting around dressed as she was with two naked pets at her feet. When she returned there was a sumptuous meal waiting her and of course two dog bowls for the pets. Luckily for them it was proper food in the bowls and not actual dog food. Miss Anna saw the look on their faces and said
"Do not be so ungrateful. Eat up or I will have the meal replaced with something you will not want to eat. Don't test my patience."
Heeding her warning and knowing not to push things the pets ate up while the two ladies enjoyed their meal and some wine.
When they were finished dining Miss Anna took the leashes and positioned the pets over the table, with the leashes tied off under the other side of the table. This left the pets flat on the table with their asses in the air. Miss Anna positioned herself behind bitch and Miss Jane behind sissy. Considering how the ladies were dressed the most appropriate item of pain was a riding crop. Soon the two ladies were laying into the asses in front of them with crops, making sure to be accurate and to leave welts.
After this was administered Miss Anna called an end to the celebration. The pets were led red assed through the club to the front door before they were finally allowed to dress. Miss Anna asked Miss Jane to ensure that sissy got home safely and she took bitch back home with her. |
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[Removed by poster at 02/03/20 09:13:49] |
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By (user no longer on site) OP
over a year ago
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The next couple of weeks were intense for most people in this story of ours. Sara and sissy worked out their notice in their current jobs and prepared to go work for Miss Anna. Jane underwent the two week maid training course to get a proper understanding and see where it could be improved. She thought that she knew how to clean though of course sissy did it for her now, but she learnt some new tricks and had some ideas on how to improve the course. Miss Anna had spoken with Marie and arranged to get the new uniforms made through her contacts. They had scaled back in sissy's and went for a pink shift dress instead.
Meanwhile Julie and whore were strengthening their relationship, with Julie pretty much having almost 100 percent control over whore. Decisions over what whore are, drank, wore, when she slept were all made by Julie. And even though it was still whore's company any personal money that came from it like salary, bonuses or dividends were controlled by Julie. Whore was given an allowance to live by.
To prove her control over whore and taking an idea from Miss Anna of all people, Julie arranged for whore to be gangbanged by five chav lads in their twenties. She took whore to an old building, dressed like the successful business woman she was ( or at least portrayed herself to be). The only sign that this may not be the case was the leash around whore's neck.
When they arrived at the building whore was led to the basement, where her leash was attached to a pipe in the ceiling. The five guys were waiting for them. Julie looked at them and said
"As agreed here she is. Any hole can be used and I want her sore by the time you are finished."
The first guy approached, took out his cock and unceremoniously shoved it in whore's mouth, almost making her gag. Another approached and without much fuss ripped off whore's skirt and shoved his cock straight into her pussy. While this was happening the other three stood around and wanked their cocks as they egged on their friends:
"Use her good, show her she is nothing but a cum receptacle for our chav cocks, no matter how high and mighty she thinks she is. Pity we are not doing this in her board room"
The two built up a tempo and were fucking their respective holes hard and fast. It did not take long for either one to cum. When they withdrew two others took their place immediately and whore's holes were in use again. After the next two had cum there was only one guy left and his was the biggest cock there. He spat on it and walked around the back of whore. Bending her over he spat on her ass and took the one hole that had not been used. Whore let out a scream as his cock entered her ass and continued screaming as he fucked her hard. When he came he emptied his cum into her asshole, leaving her with three holes full of cum.
The five chavs then stood in a circle around whore, calling her names and wanking their cocks. When they were ready to cum they positioned themselves to cover as much of her face and body as they could. They were soon spurting cum all over her. When they were finished they left. Julie had stood there watching the whole thing in silence. She approached, undid the leash and led the cum covered whore out to the car. When they got home whore was put in a dog cage in the garage and left to wallow in her cum state.
Meanwhile Amy was enjoying working in the store. No two days were the same. Some were quiet some were busy. She had spent more time displaying outfits in the window or being used to demonstrate toys for customers. On her first afternoon off she arranged to meet Lucy for a coffee and catch up. She had been intrigued by what Miss Marie had told her and wanted to know how it came about. |
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By (user no longer on site)
over a year ago
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Best ever |
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By (user no longer on site) OP
over a year ago
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Amy arrived at the coffee shop first, got herself a drink and found a discrete booth to wait for Lucy. Herself and Lucy had been friends since school and had hit it off immediately. They spent a lot of time together and as the episode with gimp in the shop showed they have experimented from time to time. Due to Amy being busy it's a while since they had properly caught up and Amy was looking forward to it. Shortly after that Lucy walked in, dressed in knee high boots, leather skirt and white top. She got a drink and headed over to greet Amy. To be fair Amy was a wee bit intimidated by how Lucy looked and was curious about the charge in her friend.
When Lucy approached she saw the look on Amy's face and smiled. She looked at Amy and asked jokingly:
"Are you ok ? You look a bit nervous, are you wishing you were on your knees kissing my boots?"
Amy blushed and stammered that she was fine though her heart was racing. What was happening to her?
They started to catch up from the night of Amy's party. Amy told about her visit to the BDSM event, her time working in the shop. Lucy giggled when she heard Amy was a mannequin at the time she was in the shop. Then Amy asked Lucy about her experiences. Lucy said
"Your party in the store was fun and it opened my eyes. I did some research and realised that I preferred to be in control rather than be controlled. As part of my research I came across the fact that certain men liked the idea of someone like me in charge. They did not feel like they were worthy to talk to me so they would spend money to be in my presence. They would adopt my bills, take me shopping, take me out to dinner etc. They expected very little in return, just the pleasure of spending their hard earned cash on me. Some had loads to spend, others had to sacrifice.
The pig I was in the shop with that day is married but in a sexless up one. He came across me online and messaged me. He has taken me shopping in couple of occasions, this outfit is from him. The trip to the store was for some toys that may be used on him or may be used on others, he does not have any say in that."
Amy looked on gobsmacked at what her friend was saying. She could not get over the changes, the increase in confidence. Lucy used to be rather shy, especially around men. Then all of a sudden Lucy spoke again
"You never answered my question when I first got here Amy. Do you wish you could crawl under the table and kiss my boots or are you too scared to admit it!"
Amy did not know what to say but eventually said
"Even if I did I would not do it in public and I would have to check with someone first"
Lucy laughed and said that answer told it's own story. She asked who Amy needed to check with and in fact dared her to.
Curious about what may happen Amy got out her phone and texted Miss Marie, saying :
"Miss Marie I am having coffee with Lucy, who is dressed as when You last saw her. She dared me to ask your permission to serve her for a short time"
She showed the text to Lucy while they waited a reply. Then her phone pinged
"Serve Miss Lucy well, no major bruises, no orgasms for you and I want full details"
Amy gasped at the reply, Lucy grinned and said
"Finish your drink slut, I need service". |
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By (user no longer on site) OP
over a year ago
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Over a coffee break at work the next day Amy brought Miss Marie up to speed.
"We finished our drinks and headed out. Goddess Lucy (as she wanted to be addressed) told me that her flat mate was away for a few days so they were heading to hers.
When we got there Goddess Lucy ordered me to my knees and told me to worship her boots, knowing I had wanted to do it since she walked into the coffee shop. She then told me to strip and wait on my knees. When she came back she had a collar and leash in her hands which were soon around my neck. When she locked it shut she said"
" When I bought these the other day I did not think I would be breaking them in on one of my best friends"
Amy continued:
"She led me into the living room and when she sat down, she told me to go back to worshipping her boots. It felt strange been naked in her presence, considering how long I had known her. As I licked her boots she patted my head. She then told me to get over her knees."
"Miss Marie said no bruises but she never said I could not warm up your ass slut"
"At that point she started to spank my ass getting harder and harder. She said that deep down she always knew that I was a slut and needed control. Her spanks got harder and my ass felt very warm. Suddenly she stopped and put me back on my knees. She stood up, removed her panties and placed them in my mouth. She took up some tape and taped over the panties. She then told me to crawl to the corner, stand with my nose to the wall and hands on head. I think she knew how humiliating this was for me. She left me there for thirty minutes while she made a drink and got something else to use.
When she returned she told me to turn around and I could see that she was now naked apart from the boots and a strap on. Taking the leash she led me to the back of the couch and bent me over. Lubing the strap on she pushed it into my pussy. I have to admit that it felt so good. She started to fuck me hard, calling me names like
Slut
Bitch
Whore
As she continued to fuck she reminded me that I was forbidden to orgasm but she would take me to the edge. She carried on for thirty minutes and it was torture for me not to cum.
The strap on withdrew and I was given a few minutes to recover. The tape and panties were removed and I was put back on all fours. Goddess Lucy sat on the couch and spread her legs. She told me to clean the strap on and then remove it from her. I was then ordered to lick her to orgasm. She taunted me about what if our mutual friends could see us now.
After giving her three orgasms I was finally allowed to leave. She told me that she would be in touch with you about using me again and that from now on she would always be Goddess Lucy to me"
Miss Marie smiled and remarked that Lucy had come a long way in a short time. |
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[Removed by poster at 04/03/20 10:06:55] |
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By (user no longer on site) OP
over a year ago
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Finally the leaving day came for Sara and sissy. They went out for a few drinks on the Friday night though sissy rarely drank. During the night they both got separate messages telling them of appointments they had the next day.
Sissy was told to wear his maid uniform, highest heels and be sure to be plugged. He had to be at John's at 1pm but no idea what for. When he arrived John led him into the living room where a table had been set out for four people. Another table at the side held drinks and snacks. John was holding up a chain configuration. There were holes for neck, wrists and ankles. When in it sissy could only crawl slowly. He was told to stay in the corner.
Shortly after three other guys arrived, all around the same age as John. The look on their faces let sissy know they were not expecting to see him there. John welcomed them and explained:
"As you know we're here for our regular poker day. I thought I would make it a bit more interesting. After each hand the winner gets to use sissy in what ever way they want. That can be as your
Toilet
Ashtray
Cum receptacle
Or you can use your belt on him.
The overall winner gets to take sissy's ass. He has been broken in by plug and strap on but never cock. This was supposed to be my honour but I am throwing it open as a bonus prize."
The other men applauded at this while sissy shook in his captivity. The game started and the betting was fierce. Maybe luckily for sissy John won the first hand with two pair. While the others cheered, sissy crawled over and gave John a blow job while the next hand was being played.
The next winner was a smoker so sissy crawled around and stayed on all fours beside him, mouth open. The guy commented that it was the first time he had used a human ashtray as he placed his ash on sissy's tongue. When he was done the butt was put in sissy's mouth for him to eat. The next winner needed a piss which could be said to wash out the taste of the cigarette.
This carried on for a few hours with sissy crawling between the winners serving them as they wanted. By the time a break was called he had given everyone a BJ, twice used as an ashtray and three times as a toilet.
It then came down to the last hand and they were all going for it. Bets were being raised and raised until only John and one other were left in. After the final round of raises hands were shown and John lost to a full house. He was frustrated but kept to his word. He positioned sissy on all fours, removed his plug. He handed his friend a condom and some lube. The guy took down his trousers and took out his small but thick cock. He covered and lubed it and then lubed sissy's ass.
At this stage sissy was not sure if he rather it was John, someone he at least knew a bit who was taking his virginity rather than a complete stranger. All of a sudden he felt the guy's cock at the entrance to his hole. He was glad for the plug and strap on training but it was still sore as the cock entered. The guy grunted as his cock broke past sissy's anal muscles and was soon fully inserted. Holding on to sissy's hips he started to fuck as he was cheered on by the others. It did not take long for him to spurt his cum in sissy's ass.
As he felt the cum drip sissy tried to gather his thoughts and how he felt. Being fucked by a man had been something he had thought about a lot. In his fantasies there may have been a bit more roughness and force involved, but fantasies don't always play out. When he came here today he was not expecting to be fucked but knew it would happen at some stage. The desire to please Miss Anna had helped overcome his nerves and reluctance. She had not forced, she had encouraged.
After a short break John took his turn in using sissy's hole and hoped that Anna would allow him many more chances. Eventually sissy was un chained and sent home. |
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By (user no longer on site) OP
over a year ago
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For those that read this and engage (rather than just make silly comments) I have a question for you
If there was a fight for control between Anna a chav trying to hide her upbringing and Julie a chav embracing her upbringing, who would you like to see win |
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We think Miss Anna would be able to deal with Julie but it would be a close run thing. |
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By (user no longer on site)
over a year ago
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Agree on Miss A as the victor. If it was between Marie and Lucy not so sure
But wherever you take the story is good with me. It's most enjoyable |
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I agree with a previous post, this would make a much More interesting film than 50 shades. |
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By (user no longer on site) OP
over a year ago
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Meanwhile story continues in part 4 |
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Anna will overpower the chav and reclaim what’s hers and banish her |
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