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sissy and his cleaner
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By (user no longer on site) OP
over a year ago
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Sissy was a quiet shy guy who kept himself to himself. He went to work but hardly socialised with those he worked with, apart from the mandatory team building days. Most of his colleagues assumed he was boring and no fun, especially as he did not drink and would hardly join in with their fun and antics. The one thing he was known for at work was his quizzes, which could be quite challenging.
Outside of work sissy did not do much else. He had some close friends who knew that he was a sissy and liked to serve and please, but having friends that knew did not mean it made it easier to find someone to please. His other big passion was the cinema and he could often be found there at least once a week, it was one of his escapes from the world.
His dressing en femme and his female wardrobe was another of his escapes, though he did not indulge as much as he could. Some would say he was fortunate living alone in that he could dress when he liked but not having someone to dress for made it less enjoyable at times. So sissy spent a lot of time online chatting and reading about sissies and how they were used. He was particularly drawn to stories about sissies becoming maids or being made to do the housekeeping. Ever since sissy got interested in dressing he had always had a liking for maid uniforms. His time spent working as a waiter started this interest when he would look at the black and white outfits of the waitresses, though of course none of them were the formal maid uniforms he fancied.
In this situation you would have thought that a perfect answer was that sissy could come home from work, change into a maid uniform and do his own cleaning. But this rarely happened as sissy could be lazy and also having few guests there was little incentive at times to keep his place totally clean, though he did try and keep on top of it. Also even though he had lived alone for many years sissy was never sure if he knew how to clean properly. The idea of getting a cleaner seemed a bit ironic to him and he was also worried about what they may find when cleaning. No matter how much he managed to hide he was sure something would be left out.
Eventually he found a cleaner through his local laundrette, someone he felt could be discrete. They had never made any comments about his bags of laundry which contained the odd female clothing and lots of panties , but very few male undies. When she first started he thought all was well and that nothing too personal was left out. Now and then he would find toys in places that he could not remember leaving them but as he was quite forgetful it could all be down to him.
One day after being at the cinema he turned on his phone and found that he had a missed call from his cleaner. She explained that her daughter had a fancy dress do at work and wondered if sissy had an outfit she could borrow, as she thought they were the same size. Sissy was shocked to say the least as this meant that his cleaner knew his secret. This bit did not surprise him but the fact that she let him know that she knew did. He was not sure what was going to happen next.
A couple of days later he came home from work and found one of his maid uniforms laying on the bed with a note beside it. It read
“why am I doing the cleaning if you have the proper uniforms for it? Will be around tomorrow evening to talk”
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By (user no longer on site) OP
over a year ago
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Nervously the next day sissy waited for the visit of his cleaner. He had thought that maybe he should just let her go and maybe find a new one but was worried about what she may do, He decided to at least hear her out. When she arrived they sat down in the living room and she spoke:
“From doing your laundry all these years I knew that you liked to dress in some female clothes – the lack of male underwear and only the occasional female blouse or skirt told me that no couple lived here. It was none of my business so I said nothing about it. When you asked me about a cleaner I was glad of the extra few quid. Of course there were times when I found things that you maybe preferred I had not but again I said nothing. But then when I came across your maid uniform I wondered why you did not do your own cleaning. Why have the clothes and not put them to use?”
Sissy nervously replied:
“I appreciate your discretion, though did find it odd that you asked me to lend your daughter an outfit. As for not doing my own cleaning, it’s quite simple. I have never really done it apart from the odd hovering and sweeping the floor and never felt that I could do a good enough job. I know that I could learn from looking on youtube but without anyone seeing the results still could not be sure it was good enough. And with rarely having visitors the state of my place was of little consequence to me. “
She said:
“I can understand that but would have thought that it would be nice to keep your place clean even just for you. A clean place gives off a nice vibe and helps you relax better. As for not being able to do it properly we can fix that. I suggest that I change my hours to times where you are here and I will train you how to do it properly. You will still pay me but it will be for the training and the supervising, rather than doing the work itself. With my experience in cleaning I will soon have you up to standard. If you want I can build in a punishment routine for slovenly work, something I gather sissy maids sometimes like. Though to be fair it will be proper punishment and I won’t accept bad work just so you can be punished. I take my cleaning seriously and would expect you to as well. And I would of course expect you to be dressed properly for the role, though for now we can forgo wig and makeup. What do you say?”
This was not how sissy had been expecting the conversation to go and his idea of letting the cleaner go seemed to have gone out of his head from the first moment she arrived. Deep down he had always wanted to be trained how to clean and knew that part of his reasons for not doing so was pure laziness. Even though he was scared he decided to accept the offer. His cleaner then arranged to come back at 7pm the following evening for his first training. She told him to be dressed waiting for him and they would start in the kitchen.
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By (user no longer on site) OP
over a year ago
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When Angela arrived the next evening sissy was nervously waiting in his flat, not sure what was going to happen. The first thing Angela did was go through sissy’s cleaning products and tell him which additional ones he needed to buy. She then set out what to use on the sink and the work tops and told sissy to clean them. While he was working she sat down in the living room and relaxed.
After half an hour she came back into see how it was doing and was not impressed with his progress. She explained that when she came to do his place she had the whole kitchen done in under an hour, not just the two bits she had assigned him. She carried on by saying that she could see why he needed a cleaner. She led him to the living room and told him to get over her knee. Taking up a wooden hair brush that just happened to be on the nearby book shelve, she started to administer 20 whacks to sissy’s ass. As she did so she said:
“Sissy needs to work harder and do a better job or sissy is going to always end up with a very sore behind.”
After the spanking sissy was sent back to the kitchen to carry on. Eventually after another thirty minutes he was done. Angele came into inspect and this time felt that sissy had done an okay job, not perfect but better than she expected. She pointed out the couple of areas that he could improve. She then had him sweep the floor which was a task he could manage.
They went back into the living room to talk. Angela set out a rota that she expected sissy to follow. Once a week he was to spend an evening cleaning his kitchen, bathroom and then another evening was to be spent hovering. On her next visit Angela would show sissy how to clean the bathroom to her standards. She then put him over her knee again and administered another twenty whacks, this time by hand. She said that this was just a reminder on how sissy was to behave and react around her. Sissy then paid Angela her normal cleaning rate and she left for the evening, stating that she would return in two days for the bathroom lessons.
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By (user no longer on site) OP
over a year ago
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Over the next few weeks Angela came around twice a week. Each time sissy was waiting in his maid uniform. The visit started with a tour of the flat to see how well sissy had been keeping it, with any mistakes pointed out and punishment accumulated. Once that was finished Angela gave out instructions on what part was to be cleaned and how it was to be done. She sat and relaxed in the living room while sissy worked, going in every now and then to check up on the work. Each visit included at least one over the knee spanking, usually with the hair brush, leaving sissy’s ass red and sore. Eventually in time Angela felt that sissy was making some progress and his cleaning skills had improved slowly.
During one of her visits Angela and sissy had a chat about life and his background. Sissy explained that he was pretty much a loner, preferring his own company. He did not particularly like his job but it paid the bills and he felt that he was okay at it. He mentioned that his interest in maid/waitress uniforms started when he had worked in restaurants when he was younger. Though he rarely saw anyone in full maid uniform, even the look of white blouse, black skirt and white apron attracted him. Apart from difficult bosses he had enjoyed his time as a waiter.
Angela asked if he would ever consider going back to it, even on a part time basis. She explained that a good friend of hers owned a select restaurant in town and was always having difficulty in getting reliable staff, especially at the weekends. Her friend liked things done properly and always had her staff turned out properly so that they were presentable. Angela could have a word and see if her friend would consider taking on a sissy waitress, as long as they worked hard and were conscientious. The clientele were very open minded and would not cause sissy any trouble. Angela took out her phone and showed sissy a picture of the uniform, which was a black satin French maid outfit, with white lacing around the top, bottom and sleeves and matched with a white frilly apron. Sissy was not sure if he wanted that much exposure but the idea of being able to wear a proper waitress uniform was very tempting.
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By (user no longer on site) OP
over a year ago
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When sissy went along for a chat with Angela’s friend, he was introduced to a young lady called Mary. Mary looked like she was in her early 30’s and was dressed very respectfully in a nice skirt and blouse combination. She welcomed sissy and told him to sit down and ask if he knew what type of establishment she ran here. He replied that Angela had said that it was a restaurant for discerning clients and Mary liked her staff well turned out. Mary smiled and replied that was correct. She carried on to say that sissy was older than most of the staff she employed and would be their first sissy, if she took him on. She felt that this would be attractive to her clientele, but it was important that sissy could look and act the part. Sissy explained that he had a lot of experience as a waiter when he was younger. Mary asked if he would have any problems working for people younger than him. He replied that as long as he was treated fairly age did not matter and he would try his best to work hard. Mary decided to give him a try out. She summoned one of her staff, a young lady called Sophie.
When Sophie came into the office, she curtsied. Sissy could see that she was dressed in the uniform as per Angela’s picture but seeing it up close had more of an effect on sissy. The black satin uniform looked so well on Sophie and it came down to her thighs. It was matched with a perfectly tied white satin apron, black tights and black shoes with a small heel. Mary explained to Sophie that sissy was to be given a trial run and he would be helping Sophie out on her shift this evening. Her report back would help determine as to whether or not sissy would be hired on a part time basis. Sophie curtsied as way of acknowledging her understanding and told sissy to follow her.
When they got to the staff rooms, sissy was shown a locker and told to remove all his male clothes and place it in the locker. Fortunately the restaurant held a good stock of uniforms, which were made for them by a specific company. Sophie handed sissy a pair of panties and tights to put on. She then helped into a waitress uniform in his size. Sissy could not get over how it felt when the black satin fell onto his skin. Sophie tied the apron around his waist and then found a pair of shoes in his size. Fortunately the heel was not too high and sissy had some experience in walking in heels. Sophie had him parade up and down the staff room until she was happy with his walk.
She then led him out into the restaurant itself, where he could see that it was split into four sections, with five tables in each section. Sophie explained that normally they had four waitresses on each evening, one for each section. They also had two others who purely served drinks and two older women who acted as hostesses, greeting the guests and showing them to their tables. As would be expected in any restaurant the waitresses took the orders for the tables in their section, delivered the food and ensured the diners had all they needed. Diners were entitled to tip if they wish which was put into a pool and shared out amongst the staff working that particular night. It was against restaurant rules to try and keep any tips given to an individual and anyone caught doing this would be publicly punished. Sophie then told sissy to stand behind her at the head of their section as they waited their first diners of the evening. Sissy was quite nervous as he had not expected to be thrown in at the deep end so quickly.
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By (user no longer on site) OP
over a year ago
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When the first customers for their section arrived something came over sissy. He forgot what he was wearing and went straight into service mode. He greeted the couple and gave them menus and asked what drinks they would like. While the drink waitress was getting the preferred drinks, sissy stood to the side to allow the couple time to review the menu. In an instant he was transported back in time to when he first worked as a waiter. Obviously the uniform was different but everything else felt the same. Sissy got that same feeling of satisfaction he got from serving and pleasing others. Even though there were times he did not get on with his boss back then, he knew he was good at his job and would always have a role there. There were very few jobs in sissy’s life that gave him the satisfaction that being a waiter did. As he took their order and delivered it to the kitchen, Sophie just looked on in amazement. She could not get over the change that had come over sissy. Gone was the shy person who was worried about being seen dressed as he was and in its place was a smiling welcoming server, only too happy to please.
After a while a group of four ladies were shown to another table in their section. This time Sophie took the lead and got their orders in. When the food arrived sissy helped Sophie deliver it to the table. This was the first time that the ladies got a proper look and realised that sissy was a sissy. Sophie explained that tonight was his trial run and she hoped that his service would be up to par. After that the ladies paid little attention to sissy, apart from keeping him busy with small requests. The next table to arrive was a group of three business men and sissy was a bit more nervous about this one. He was expecting some comments from them, but he had under estimated the clientele in Mary’s restaurant. They knew the reputation of the place and how they expected their staff to be treated. Anything untoward would lead to a ban from the restaurant and none of the regular clients wanted to risk that. If sissy had known this from the off he may have been less nervous from the very start.
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By (user no longer on site) OP
over a year ago
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The rest of the evening went very smoothly and flew by as their section was quite busy. It seemed the addition of a sissy waitress had people asking to be sat in that section of the restaurant. At the end of the night Sophie and sissy were back in Mary’s office and Sophie was asked to give feedback. She admitted that she had been totally surprised as to how well sissy had done, he had taken to the role naturally and many customers complimented him on his service and found it hard to believe that it was his first time. There was also an increase in the tips generated which all staff would benefit from, so the rest of the staff were also happy with sissy’s performance. Mary asked sissy how he felt the night had gone, to which he replied:
“At the beginning I was so nervous. It is different being dressed like a sissy in my own place compared to being in front of others, especially a group of strangers like tonight. However once the work started it brought back memories of my previous times as a waiter. The satin outfit just became the required uniform for the job and people don’t always like the clothes they have to wear for work. As the night went on I began to enjoy the feel of the satin on my legs and was trying to make sure that the apron was properly tied and centred. It felt right and Sophie was a great help. I can honestly say I loved the experience.”
Mary and Sophie smiled at each other and Mary congratulated them both. She told sissy that if he wanted there was a job here for him every Friday and Saturday night and maybe even Sunday afternoons. She also explained that sometimes the restaurant was booked out for private parties that he may be required to serve at. His uniform would be kept at the restaurant and would be cleaned by the in house laundry service. He would always be expected to be dressed immaculately and to behave as well as he did tonight.
Sissy had to think about it for a few moments. With his current day job and the two nights he was committed to undertaking his cleaning training with Angela, working here would not give him much free time. He did realise that it would be better than sitting at home dreaming and remembered that previously when his sissy life was somewhat engaged, it helped him deal with the stresses and strains of normal life much better. If he had an outlet for sissy minor issues at work did not rile him so much, so he told Mary that he would be happy to accept the role and hoped that he could always work with Sophie. This was accepted and Sophie was more than happy to have sissy as part of her section team.
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By (user no longer on site) OP
over a year ago
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The next evening sissy was due to meet Angela at his as arranged. This time however they did no cleaning or training as Angela wanted a full report on the night in the restaurant. As sissy was outlining how it went his enjoyment and delight in the night was so obvious to see. Like Sophie, Angela was surprised as to how much sissy enjoyed the night and was delighted when she heard that he had been taken on there. Angela also said that she was impressed as to how sissy’s cleaning skills were coming on and that his place was looking a lot neater than when she first came to clean. She jokingly wished that she could meet other sissies on her job as would make life easier but there was only one.
Angela asked if sissy would in time consider cleaning other places as she was sure that she knew a couple of people who would like the idea of having a maid and not having to worry about housekeeping. Sissy said that he would consider it when Angela felt his skills were good enough and as long as it did not interfere with his day job or his new weekend job. Angela then left and sissy tried to get some sleep. He would need his rest as tomorrow was Friday so it would be his first three day stint at the restaurant.
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By (user no longer on site) OP
over a year ago
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Sissy could not wait for clock off time from his day job to come on Friday. Normally he had nothing to look forward to for the weekend but this would be so different. He knew that he may be tired on Monday but would be so worth it. As soon as he could he left work, dashed home for a quick shower and then headed to the restaurant. Due to his day job Mary had given him some leeway on his start time on a Friday. When he came in Sophie greeted him with a smile and helped him get changed. Once the uniform was on all his day to day stress seemed to vanish and he went into service mode. Sophie told him that they were going to be quite busy tonight as there were a few groups booked in, including a group of local business women.
Once out in the restaurant Sophie and sissy were busy looking after their guests. Soon it was time for the business women to arrive and as they approached, sissy saw that it was a group of four women, all dressed in professional business suits. They were chatting and laughing together as they approached their table. Just as sissy was going to give them menus and ask for their drinks orders, he caught a glance of one of the women close up and his heart stopped. He did not know if she had recognised him but they had known each other when they were younger. They had never dated though he had always wished he had the nerve to ask her out. Pulling himself together he gave out the menus and passed the order for drinks to the waitress. He walked away from the area to give them a couple of minutes to view the menus and to get some composure. He would have to deal with it if his former friend recognised him. He briefly told Sophie what was happening.
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By (user no longer on site) OP
over a year ago
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When sissy went back to take the orders, he was looking at each woman as they spoke to him. His former friend was the last one to order as she did, a flash of recognition passed through her eyes. She said nothing out loud but smiled at sissy. As he went away to pass the order to the kitchen, he was imagining her telling her colleagues how she knew the sissy who was serving them. Of course he had no idea what if anything was being said. He put it out of his mind as other groups arrived and Sophie and he got quite busy. He was glad that his heels were not that high as his feet would have been killing him. It reminded him of why all the waitresses he knew from the past had always worn low heeled shoes. They had learnt their lesson from when they had worked a night in high heels, which may make their legs look great but were so sore on the feet.
Later on in the evening his former friend got up to go to the bathroom. On her way back to the table she stopped by where he was standing to have a quiet word. She asked how he was and that it was a nice surprise to see him again, though the surroundings and circumstances were a bit unexpected. He replied that he was fine and was sorry that they had lost touch. At times he found it difficult being around people who did know the real him as he had to watch what he said and often felt that he was lying to them, even though most people had parts of their lives that they kept private. He had always admired the way she dressed and on occasions had coveted a couple of her outfits. She told him that he looked very cute and seemed quite happy working here. She asked if they could meet for a coffee for a proper chat and catch up. Nervously he replied that he was free after his Sunday lunch time shift if she wanted to meet then.
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By (user no longer on site) OP
over a year ago
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The rest of the night went well and when sissy got home he was knackered. However he had no trouble sleeping which was unusual for him. Often work issues would go through his mind all night and he would hardly sleep. The new job was giving him so much enjoyment and fulfilment that it allowed him to relax. If he had found it earlier in life things may have been much easier for him and he may not have suffered as much stress and anxiety as he did.
His shifts for Saturday evening and Sunday lunch passed without much incident, though sissy was getting a lot of praise and compliments from the guests and from Sophie and Mary.
Soon it was time for his catch up with Julia. They arranged to meet at the restaurant after his shift where Mary had told him they could have a discrete quiet table for their chat. He got changed out of his uniform and was in slacks and a shirt but with nice panties on under. Julia arrived wearing a very nice dress and heels and he could just see the hint of stockings, which he always loved. They greeted each other, sat down and ordered some drinks. Julia reiterated how much of a surprise it was to see him at the restaurant but she was delighted. She was always sorry that they had lost touch and apologised for not making more of an effort to stay friends. He explained that it was fine and they could make up for it now.
Julia smiled and asked if he had ever worn panties or anything else when he was around him. He nervously admitted that he had often been in panties and the odd time suspenders and stockings. She smiled at this and admitted there was the odd occasion when she thought she had seen a suspender belt outline through his slacks but was too afraid to say anything. He admitted that he had often wondered what would have happened if someone had noticed, but was always too scared to push it. You could never tell how people were going to react. Julia asked how he ended up working in the restaurant and not wanting to keep secrets any more, he explained the story about his cleaner, her training him to clean and introducing him to Mary. Julia said that when she had seen him on Friday night, after the shock, she could not get over how happy and relaxed he was and her friends complimented his service throughout the night. This made sissy blush.
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What lovely journey sissy is having getting to do things he’s wanted to do deep down for years. How many of us have had that ‘should have done it earlier’ moment, when we realise how good doing some things feels.  |
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By (user no longer on site) OP
over a year ago
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Sissy decided that it was time for no secrets and to tell Julia everything. So he told her about how he started dressing when he was younger by borrowing family clothes, until he was caught. How he struggled with this new side of him and did not know how serious he was about it. How he went to a dressing service and saw his femme side all made up for the first time. There was no surprise that he had decided to be dressed as a waitress and how it felt natural. How he loved the pictures until he destroyed them after a bad reaction from a friend, but managed to rescue part of one. How he got involved in the bdsm scene when he moved for work, though did not immediately introduce his femme side. How he explored and had fun and learnt a lot, and how he did things en femme that he never felt he would have the nerve to do online.
He explained about the hidden angst inside about keeping this side separate and the stress and anxiety it caused him, as he did not know how people would react. Those who knew were great about it but not all of them could help him explore in the way he wanted to. How he started using online forums and ads to find men that he could try and satisfy orally. How he had never done anal with a man but had been pegged by a few different women and loved it. And finally how much this new part time job meant to him and that it gave him more satisfaction and enjoyment than his day job, which was needed to pay the bills.
Julia sat quiet throughout all that and just let sissy speak. She guessed that he had needed to say that for a long while and did not want to stop his flow, though it was a lot to take in. When he was finished she had some questions for him, not all of which he could answer.
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By (user no longer on site) OP
over a year ago
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The first question Julia asked was what type of clothes sissy liked to wear. Sissy explained that it varied and depended on whether he was going for the full en femme look or the sissy look. Most of his en femme clothes were bought from normal high street stores and consisted of blouses, skirts and dresses. These were clothes he could walk down the street in and when he was braver he had in the past. Due to his interest in BDSM he had some kinky outfits like PVC and leather which only came out on club nights. He reiterated that his en femme side had not seen the light of day in quite some time. Sissy’s outfits were more simple, consisted of maid uniforms, cheerleader and the like. Things that may get men excited or prove his subservient side.
Julia’s next question was whether sissy was gay and did he fancy men sexually. Sissy replied that he honestly did not know. He enjoyed giving men oral pleasure partly because he believed that was what a sissy was supposed to do. It did not turn him on but it gave him some form of pleasure in his head. Maybe through stories or online research he had trained his mind to believe that sissies should not get sexual pleasure and it was all about others sexual pleasure. A sissy was to be used and be of use. Julia then surprised sissy by saying that she would love to see him pleasure a cock, as she had always liked the idea of watching a sissy in service. Sissy was a bit surprised that Julia would know much about sissies but guessed he never really knew what she was into or what interested her, especially since they had lost touch.
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By (user no longer on site) OP
over a year ago
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They agreed that sissy would go around to Julia’s after his day job on Wednesday so they could continue the chat and explore a bit more. Monday and Tuesday at work passed with no issues. A couple of his colleagues noticed he seemed to be in a better mood but none of them could understand why and he was not letting on. After work on Tuesday he was looking forward to his cleaning with Angela. He was unsure at first but deep down he knew that he was learning a good skill and even though he had few visitors, it was nicer to be living in a cleaner place. When Angela arrived he was set the task of cleaning the bathroom and kitchen while she relaxed. After an hour Angela checked up and was impressed with the progress but noticed that sissy had missed some dust behind the toilet in the bathroom. She summoned him to the living room where she had positioned a chair. She sat down and sissy went over her lap. Pulling up his skirt she raised the hair brush and gave him twenty hard smacks, telling him not to undo the great progress and ensure his work remained to standard.
The next day after work sissy arrived at the address Julia had given him and found it was a nice apartment block. When he was let in he found out that Julia had the top floor. He could tell from the layout that Julia was doing well for herself. She was dressed in a very nice black satin skirt and a white blouse, with 5 inch heels on. Julia noticed sissy looking at her outfit and wondered if he wished he was dressed the same. She led him to the living room and poured them both some drinks. Julia explained that she worked as a lawyer and was quite high up in her firm and was proud of her job and what she had achieved. She explained that she never married but had dabbled with experiences of both sexes and was quite open in her desires and her needs. Hence her idea of sissy sucking cock for her. It was something she had always wanted to see but never thought she would know someone willing to do it. As they spoke Julia told sissy to feel the satin skirt she was wearing. Julia had seen how much sissy liked his satin waitress uniform and figured that satin had an effect on him. She then told him to wait there while she got something. She came back with a dress hanger and when she undid the cover, inside was a very formal pink satin mini dress. Sissy’s eyes almost dropped when he saw it.
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By (user no longer on site) OP
over a year ago
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Julia spoke:
“Sissy you have a decision to make. I did not say anything about it before because I remember how much you like to procrastinate and over think things and was sure you would talk yourself out of it. Of course you have the right to say no which is fine but I think deep down you want to please me and you want to try things. If so please take this dress and go into the bedroom and put on what is there and come back out. I asked Sophie what size your uniform was so think I got the right sizes.”
Sissy said nothing but took the dress and walked into the room that was pointed out to him. On the bed was a set of pink satin lingerie and by the bed were three inch pink heels. He took off his male clothes and put on the pink panties and bra, loving the feeling against his skin. He then carefully took out the dress and slipped it over his head which felt divine on him. Finally he added the white tights and the heels, all of which fitted perfectly. The last thing left on the bed was a collar that said “sissy”. A little curious but not stopping now he put it on and returned to Julia.
Julia gasped as he walked back into the room and said how great he looked. She told him to do a twirl so she could get a proper look. After that she told him to come and kneel in the centre of the room with his hands facing upwards placed on his lap. When he was in position she approached him with a white scarf which she used to blindfold him. Just then there was a ring at the door. Julia told sissy to stay where he was as her other guest had just arrived. Sissy could hear her welcoming someone in and the two of them approach.
Sissy then heard a zipper being pulled down and Julia asking if he was ready to please her. A bit confused but excited, sissy just nodded his head. Julia told him to open his mouth. When he did he felt a man’s cock being placed in it, pushing past his lips and down his throat. Soon he was gagging on it. Julia knew that this was not the first cock sissy had sucked but maybe was the first one while blindfolded (or maybe not). The unknown guy took hold of sissy’s head and using his hands he started to face fuck sissy.
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"Question is will sissy know the person he is sucking to please Julia and if he does, will he like them"
Or will it matter if he likes them or not as Julia takes on the role of his mistress and makes him obey her wishes   |
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By (user no longer on site) OP
over a year ago
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As sissy was sucking the cock he could not help but wonder if he knew the person who owned it. In some ways he doubted it as Julia and he did not have many friends in common and like him, she may not have kept in touch with many of them. It was not the first time he had sucked an unknown cock. Some of his previous meets preferred the idea of sissy not knowing and had requested that sissy be kneeling blindfolded when they arrived. It added a bit of something to the meet though also made sissy a bit more nervous. He had to be careful who he arranged to do such things with as he had no idea who they were or what they may do to him. Some of his meets had been called off because of gut reaction, with others maybe he was either lucky or
a good judge of character.
As the cock grew more in his mouth sissy was glad of the dildo training he had done to try and stop having a gag reflex, though sometimes the cocks were so big that he could not help but gag. There were even occasions where the cock made his eyes water and he could imagine if he had worn makeup, it would be all over his face by the end. Even though the current cock in his mouth was big and girthy the guy was not being too forceful. Sissy assumed he was under orders from Julia not to hurt sissy too much. Sissy also assumed that if this went well it may not be the last cock he sucked for Julia but of course he had no idea what she may have planned. After about 20 minutes of face fucking sissy could feel the cock twitch and soon his throat was being filled with cum. He tried to swallow it all down and not waste any. Eventually the cock stopped and his mouth was used to clean the cock off and then it was removed. Julia patted him on the head and said:
“Well done sissy, now stay there while I see my guest out”
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By (user no longer on site) OP
over a year ago
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When Julia came back in she found sissy kneeling where she had left him, like a good pet. She walked over and asked if he enjoyed that and if he wondered who it was. Sissy replied yes to both questions but said the latter one was not that important as he did it to please Julia, not necessarily to please the male. Julia smiled and then reached down to raise the bottom part of the dress and have a look at sissy’s privates. She said:
“I was thinking that maybe we need to lock this little thing up. I was reading that sissies are better behaved if they are in chastity and have no control over when they cum. Seeing what you have there I can see why you are a sissy but also that may need a special device to keep you out of trouble. Maybe a cage with chains on it that goes around the waist? How would you feel about that?
Sissy took a moment and replied that he had often dreamt of chastity but had difficulty in finding a device that suited him. He had gone through periods of denial by word but that took a particular kind of trust and was not the same as seeing a woman play with the key in front of him. Julia told him to leave it with her. She then suggested that he got changed and went home and she would be in touch soon. As may be imagined sissy had a lot of thoughts going through his head while he tried to sleep that evening, but this time they were all pleasant rather than worrisome.
On Thursday when Angela came for his cleaning training her daughter was with her. Angela introduced her as Sam and explained that Sam was getting quite busy at her work and was falling behind in her housework. Angela thought that sissy could spare an evening to help her out and yet again would be some extra money for him. It turned out that Sam lived just up the road so would be easy for sissy to get to. Sam was here to see how good a cleaner sissy was and if he could cope with her needs. Fortunately her flat was about the same size as sissy’s so a couple of hours a week should help keep it under control. Sam explained that she would provide a uniform and had high standards. After seeing how well sissy was doing with his training, Sam conferred with her mother and told sissy to be at hers the following evening to be shown around and for a private chat.
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By (user no longer on site) OP
over a year ago
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Sissy reminded Sam that Friday evening was one of his nights to work in the restaurant but if she was as close as Angela said he could call in briefly on his way to work. When sissy arrived at Sam’s place the following evening he was shocked how close it was, way closer than Angela had led him to believe. He was let in and shown around. It was a two bedroom flat like his, with a small kitchen and bathroom and a decent size living room. Sam told him that one of the bedrooms was off limits and she would not need him to clean there. This of course made sissy curious as to what went on in there. Sam showed him the uniform she had picked out for him, which was similar to what he wore in the restaurant but was in pink rather than black. Sam felt that pink suited a sissy better. At this comment sissy was wondering how all these women seemed to know a lot about sissies, where he had always thought not many people were interested in what he considered a niche interest. Sam explained that she would expect the bathroom and kitchen cleaned once a week, the bed made and living room tidied up. Once every two weeks the living room and bedroom were to be vacuumed. With the training he had received from Angela it should take no longer than two hours. Sam told sissy to be at hers next Thursday for his first shift. Sissy then left to get to the restaurant.
When he arrived he got told off by Sophie for being late and quickly got changed and headed out to the dining area to prepare. It took a while for the restaurant to get busy so sissy had time to think about the changes in his life and how he felt about them. It had been a whirlwind but he had to admit that he was possibly happiest than he had been for a while. Having too much time on his hands often led to wasteful experiences and bad thoughts. Being kept busy in the service of others may be tiring but it was good for him. For the first time in ages he felt useful and as if he had a purpose in life. The restaurant started to pick up and Sophie and he were rushed off their feet for the rest of the evening.
Just before he was about to change and head home Sophie told him that Mary wanted to see him in her office. When he arrived there she was looking quite stern. She reminded him that she had given him a bit of leeway about his arrival time on a Friday but she felt that tonight he had taken that to the extreme. She told him to bend over the desk and raise his uniform. When he was in position she pulled down his panties and took up a wooden ruler. She administered twenty hard smacks with it, reminding sissy that punishment for tardiness or mistakes were discussed at the interview. Trying not to cry sissy just took his punishment and stayed silent. He was let go to change and went home with a sore butt, determined to do better in future. He did not want to mess up these new opportunities.
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By (user no longer on site) OP
over a year ago
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Saturday and Sunday shifts at the restaurant passed without any issues. They were busy and many of the clients were complimentary about sissy’s service. As the amount of tips also increased the rest of the staff were also happy with the new addition. On Sunday Julia was there when he finished work and said that she had something for him. They went back to her place where sissy was told to strip.
Julia got two scarves and used one to tie sissy’s hands behind his back and the other to blindfold him. He could then hear her getting something out and suddenly he felt cold steel against his little clit. A cage of some sort was fitted and then chains were wrapped around his waist keeping it in place. Julia took off the blindfold and positioned sissy in front of a mirror so that he could. A small steel cage was now sitting on his clit and the chains ensured that it stayed tight. There was a hole at the end of the cage so that sissy could still use the toilet, but would have to do so sitting down. This would not be an issue as it had become natural for him to use the facilities this way, so much so it often caused issues when out If he could not find a spare cubicle. Julia explained that she had taken sissy’s special needs into consideration when deciding on the device. She then knelt in front of sissy and locked the device on. The key was on a chain which went around her neck.
Having dreamt of this moment for so long it took sissy a few moments to get used to the fact that his little clit was now locked up. He never thought that he or anyone would have found an affordable device that worked. He wondered how long he would be locked for but knew now was not the time to ask. Julia undid his hands and told him to get dressed and head home and that she would be in touch.
Tuesday’s cleaning with Angela was extra strict as she did not want sissy letting her down with his first proper visit to Sam on Thursday. When that fateful evening came around, sissy arrived at Sam’s after work. Hanging from a hanger in the bathroom was his uniform which Sam told him to get into. She had left out the cleaning products and tools he would need to do his chores. She sat and relaxed in the living room as sissy cleaned the kitchen and bathroom. The kitchen sink was over flowing as if Sam had not washed anything for almost a week. It took sissy about an hour to clean the kitchen and about the same time to do the bathroom. He was then told to kneel in the living room while Sam inspected his work. She came back and said that it was adequate but he would need to speed up as it should not have taken so long. This was something sissy had been told before by a friend when he tried maiding for her. Sissy was told to get changed and leave. He headed home with a few thoughts on his mind, especially about how he was adjusting to his chastity. He always knew that there was a huge difference between fantasy and reality and he was suffering the reality at the moment.
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By (user no longer on site) OP
over a year ago
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Over the next few days sissy got used to wearing his device. He did not see Julia during this time but she would text him and got him to provide photos to prove the device was still on. She seemed to like teasing him about it The work at the weekend was quite busy, with mixed crowds in. The restaurant had a good reputation but not many families came in as it was not really set up to cater for them. It was mainly couples, groups of women or groups of men or business dinners that seemed to attend. It was easy to spot someone new to the restaurant as they had a look of amazement about them, especially when they saw the uniforms and when they saw sissy, but they did not say much. Sophie explained that anyone who brought someone new was held responsible for their behaviour and that if they misbehaved, both the guest and the person who invited them would be banned.
The next major incident to occur in sissy’s new life was when he was back around at Sam’s place the following Thursday. When he got there and had changed she explained that she had to pop out for a few minutes but would be back to check on his work. She was wearing a full length coat but sissy could see that she was wearing boots, which tweaked his interest and made him feel the cage a bit more. He set about the tasks he had been set, not wanting to upset or annoy Sam. When he was hovering the bedroom, he noticed that the door to the second bedroom was open slightly. Normally this room was locked and Sam had warned him to stay away from it. The question was now did sissy want to risk trouble by finding out what was in that room and if he did would Sam find out. Just as he was about to approach the door to close it properly, Sam reappeared and asked him what he was doing. She reminded him that the room was out of bounds for him. He explained that he knew that and was just going to close the door properly but she did not seem to believe him. He wondered if he had been set up.
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By (user no longer on site) OP
over a year ago
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Sam approached and opened the door and took sissy inside. Whatever he was expecting to in the room would never have matched what was there. There was bdsm equipment in the room including a kneeling bench, a St Andrews cross and a cage. There were also racks on the wall which held various bits of kit and toys and a couple of wardrobes, which could have held anything. Sissy was led over to the cage, told to get on all fours and crawl in. When he did so, Sam locked the cage behind him. She then went to the wardrobe and took off the coat she was wearing. Under sissy could see that she was wearing a leather corset, leather skirt and the boots that he had caught a glimpse of earlier. Sam hung up the coat and them came back to the cage and sat on a chair just in front of. She then said:
“My mother knows nothing about this room and what goes on in here and that is the way I want it kept. If you want to keep cleaning for me you need to keep quiet about this or else we will part ways and you will have to explain to her why you messed up. When she first mentioned the idea of you cleaning for me I was worried but when I heard that you were a sissy I thought that if you found out, you may be able to keep it to yourself. If that is the case I am sure that I can think of some fun we can have in this room from time to time. My mother thinks I need a cleaner due to being busy at work, which is partly true. It is just that I have two jobs and this one does keep me rather occupied outside of the day job. Now you would have thought that doing this job it would be easy to find someone who would be willing to clean for me. But as am sure you know there is a big difference between people wanting to clean in fantasy world and those who can actually do it. Knowing that my mother had trained you to her standards made me realise that you would actually do the work and not just prance around in your satin uniform waiting to be punished. Though as you can see I am well capable of dishing out punishment if needs be. Do you have any questions?”
A thousand questions were going through sissy’s mind at this stage but he did not know where to start. He had read about and seen pictures of such rooms online during his research but never known anyone who had one in their homes. He thought such equipment only was found in dungeons or clubs, where he was fortunate to visit from time to time. To find such a room on his doorstep was a surprise, but a nice one. He asked Sam how she got started in this line of work.
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By (user no longer on site) OP
over a year ago
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Sam said:
“I started exploring for fun with an ex boyfriend, just simple things like using scarves for bondage etc and a bit of spanking. I soon realised that I preferred to be the one in charge rather on the bottom. After that I did some research online and found there were many interested and some would happily pay to get the experiences they were after. I contacted a local pro domme and went to train under her for a few months to gain my experience and knowledge. Then I slowly started up my own client list and took my time building up here. I don’t do it often and prefer repeat clients so can get to know them better and know how their body reacts. It is a nice distraction from the day job and I enjoy it as well. It is not always you get to work at something you enjoy.”
Having his new experiences sissy could agree with that statement. He then asked why Angela did not know and Sam felt that she would not understand. Hopefully some day she will be able to tell her but did not ruin the relationship that they had. Again from his own experience sissy could understand that and agreed to not say anything to Angela. He was let out of the cage and strapped down to the cross. Sam came behind and lifted the bottom of his uniform and lowered his panties. She then used her hand to give sissy a nice red backside, which he strangely found enjoyable.
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By (user no longer on site) OP
over a year ago
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All of a sudden Sam asked how good sissy was at oral. Sissy explained that he had not given many bjs but he did enjoy doing it. Sam then asked if he was happy to help out with a client who was due soon. Both sissy and the client would be hooded so would not see each other. Sissy thought about it for a moment and agreed to help. Sam smiled and unstrapped him from the cross and led back over to the cage. Before he was put back in Sam placed an isolation hood over his face, blinding him. The mouth was left open and Sam added an ring gag to keep sissy’s mouth open. She told him to stay quiet. Sissy could hear Sam leave the room.
About fifteen minutes later he heard the front door bell go and assumed that Sam’s client was here. He could hear little else until he heard Sam’s boots on the floor in the room. Sam later told him that her client was naked and hooded and led into the room and bent over the kneeling bench and strapped down. Sam then put on strap on and fed it into the client’s mouth for him to lubricate. She then withdrew and walked to the back of the bench and started to peg the client, which was one of his favourite activities. After a few minutes she withdrew, let sissy out of the cage and told him to crawl under the bench. There was a hole in the bench through which the client’s cock was sticking out. As he liked being pegged his cock was rather engorged but he never expected Sam to do anything with it, no matter how much he begged. All of a sudden Sam entered the client’s ass again and at the same time sissy’s wet mouth wrapped itself around the client’s cock. The client was totally surprised as he was being penetrated and sucked at the same time. As Sam pushed in an out the client’s cock was being licked and then sissy took as much of it as he could in his mouth. Himself and Sam built up a good rhythm and it was not long before the client exploded into sissy’s mouth. Sam carried on pegging the client and told him not to expect this treat every time.
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