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sissy's business trip away
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By (user no longer on site) OP
over a year ago
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Sissy was a middle aged man who pretty much kept to himself. He worked in an office though most of his co workers knew very little about him. Most considered him to be stand offish and a bit boring. He did not really like joining in any of their social nights and he did not drink. When he was at home he kept to himself as well and did not have many friends. Most of his time was spent online chatting with strangers about his dressing and needs to serve and be used.
One day at the office he was told that they needed him to go on a training course for a week. As the course was five hours away he would be put up in a hotel for the duration. He was not exactly happy about it but there was little he could do. Like many people he needed his job. He was allowed to leave early and pack for the trip as he had to catch a train that evening.
As he was getting his clothes ready for the trip he decided he may as well make the most of it and he packed some of his alternative wardrobe as well. Mainly some nice underwear for under his work clothes and one or two outfits. At the last minute he added in the skimpy maids uniform he had just purchased off eBay but was yet to wear.
After a tiring but uneventful journey he finally arrived at the hotel and checked in. After unpacking and hanging up his clothes he ran a hot bath and relaxed. He then decided to do something he rarely did which was to shave off all his body hair. When he was finished it felt a bit strange but also nice. He then put on a black bra and French panties with matching stockings. Rolling the stockings up his hairless legs gave him a little thrill. He then tried on the maid uniform and imagined cleaning his hotel room. Shortly after he undressed again and retired for the night.
The next morning he selected a black cami and knicker set to wear under his work clothes. The course was long but slightly interesting. He turned down the chance to go for a drink with some of the other participants and headed back to his room.
When he got there he was surprised to find that it had not been cleaned. He was about to ring reception and complain when he saw a note attached to the door of the wardrobe. It said that housekeeping had come to clean but decided that any man who brought a maids uniform away with him obviously liked cleaning. Someone from housekeeping would be at his room at 7 and expected him dressed and waiting to be shown how to clean. If not his company would be informed of his little secret. He was shocked and unsure what to do but realised he only had twenty minutes to decide. |
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By (user no longer on site) OP
over a year ago
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Twenty minutes later there was a knock on his door. Very nervously sissy opened the door a small bit and saw a young lady standing there with a housekeeping trolley. She was dressed in a pink stripped maid dress with an over the neck white apron. Her name badge said her name was Jane. She looked at him and asked if he was going to let her in or was he going to come out. He quickly opened the door so Jane and her trolley could enter the room.
She closed the door behind her and then addressed him, saying "Mr J***** who works for *****", please twirl and show me your uniform". Shocked by the amount of information she knew about him, he turned around so she could get a proper look at his uniform. She tutted as he did so , explaining how impractical his uniform was for doing any proper cleaning. She also admonished him for showing too much skin and for having his panties on show.
Jane then sat on edge of the bed and pointed for him to go over her knees. He did not think she was serious and he nothing. She looked sternly at him and explained if he was not over her knees in ten seconds an email would be sent to his work. Immediately he got into position and felt the skirt of his uniform being raised and his panties lowered. Jane then started to spank his ass, telling him off for daring to turn up for work in such a slutty uniform. She also asked what type of business man came on a training course with a maids uniform. "Obviously Mr J*** you are nothing but a little sissy bitch"
When she finished spanking him she told him to stand against the wall with his hands in his head. She went on to explain that shortly she would show him how to clean his room and he would be responsible for doing it each day of his stay. She would visit each evening and inspect his work and deal with any mistakes. |
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By (user no longer on site) OP
over a year ago
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Obviously this is fiction. If I was ever brave or silly enough to bring a maids uniform to a hotel, unfortunately I doubt it would be noticed or commented on. Housekeeping have a hard enough job as it is. |
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By (user no longer on site) OP
over a year ago
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When she had finished talking Jane went to her trolley and picked up cleaning products and wipes. She handed sissy a pair of pink rubber gloves and told him to follow her into the bathroom. Thankfully there was not much of a mess here. Ever since sissy was younger and without anyone telling him to, he always sat when he used the toilet. Maybe he did not feel manly enough to stand or was worried someone would notice his panties.
Jane handed him a cloth and cleaner and told him to get down on his knees and clean the toilet seat and lid. As he did so the bottom of his uniform rose up and showed off his panties, to which Jane just tutted. She then told him to take the toilet brush and scrub inside the toilet. Next they moved to the sink and he was handed another cloth and different cleaner and told to scrub it. When Jane saw the state sissy left the bath in, with his hairs all over she was furious. She bent him over the bath and walloped his already sore ass and then had him scrub the bath clean.
They then moved back to the bedroom where sissy was instructed on how to make his bed properly. Thankfully for him the rest of the room was ok. When he was finished he was exhausted but Jane just laughed. She explained that in the time it took him she would have done three rooms. He needed to speed up if he wanted to be a hotel maid. Looking aghast at this comment sissy was not sure what she meant.
Once the bed was made sissy was told to lie on it and spread his arms and legs. Going back to her trolley Jane collected some old tights and proceeded to tie sissy spread eagled to the bed. She removed her panties and using another pair of tights she gagged sissy with them. She said that she would be back at 6.30 am to release sissy before his course started and then she left. After struggling against the bonds sissy realised he was going nowhere. |
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By (user no longer on site) OP
over a year ago
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The next morning sissy woke up from a very uncomfortable night with little sleep. He had to lie there until Jane came to free him. When she finally did he headed to the bedroom to relieve himself. He then got dressed as male so he could head down for breakfast. Jane told him to come straight back up, change and clean his room before heading to his course. He would not have time later as Jane had something else planned.
He hurried down to breakfast, saying very little to any one else on his course. He then headed to the room, changed into his maid uniform and cleaned his room, hoping he did it to Jane's standard. He then got changed into work clothes, choosing pink panties to wear under. He found it difficult to concentrate on the course due to wondering what Jane had planned. At the end of the day he felt rude turning down the drink invite but knew Jane was waiting.
When he got back to the room he found a suit hanger on the back of his door, with an attached note telling him to get changed. He stripped off his current outfit and opened the bag. The first thing he found was a white bra and panties set, more practical than what he preferred to wear. Then there was a uniform like Jane's with a name badge reading "sissy" and a matching apron. Completely shocked by this and wondering how Jane had moved so quickly. He put on the uniform and apron and waited for Jane.
When she arrived she smiled and said that his uniform was much more suitable. She told him that he was going to help her clean two rooms on the floor. He argued back that he could not leave the room dressed as he was but Jane just replied that he had no choice. |
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By (user no longer on site) OP
over a year ago
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Jane further explained that normally all rooms were cleaned before 3pm but no one had booked these two rooms until tomorrow. She thought it was the perfect chance to train sissy some more. Also she felt sissy owed her some help after all the help she had given him. No one brings a maid uniform on a work training course unless deep down they wanted someone to find it.
She then opened the door and told sissy to follow, which he did nervously. Hoping they would not bump into anyone else and were not going far, sissy was relieved that the first room was right beside his. They entered and Jane told sissy to put on gloves and start in the bathroom. When sissy entered he realised that the previous occupiers were not as accurate as him and that there was piss stains all over the floor. He got down on to his knees and started to clean the floor and the toilet itself. That alone took him a good thirty minutes and the rest of the bathroom about the same amount of time. He then went back into the main room and helped Jane make the bed.
They moved on to the next room where Jane sat in a chair and let sissy do all the cleaning himself. Thankfully it was not as messy and did not take as long. By the time they made it to sissy's room he was knackered. Jane told him to strip to his white undies and to hang up his new uniform. She then proceeded to tie him up again and left him to try and sleep. |
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By (user no longer on site) OP
over a year ago
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The next day started off the same for sissy as Jane arrived just after six to release him. He hurried down to breakfast and then back to change into his uniform and cleaned his room before heading off for his course. Part of him was relieved that this was the second last day and this would soon be all behind him.
When he got back after the course he got changed and waited for Jane to show up, wondering how many rooms he would be cleaning. While he was in the bathroom he heard the door opening and assumed it was Jane coming in. However when he went into the bedroom there was an older lady standing there, dressed in the housekeeping uniform. Her name badge said that she was called Marta and she was head of housekeeping.
She looked at sissy in his uniform and told him to come and stand in front of her as she sat on the bed. She said that she had come to the room to see what was going on as rumours of a new maid had spread and she knew no one had been hired. Jane and sissy may have thought they were being discrete but hotels have ears and eyes every where.
A few minutes later Jane let herself in and was shocked to see Marta sitting there. She tried to explain what was going on and that she had meant no harm but Marta just told her to shut up and that she would be dealt with later. Marta got up and walked around thinking and then told Jane to sit on the bedroom chair. When she was in place Marta proceeded to tie her to the chair and gagged her.
She then left the room with sissy and headed off to the rooms that Jane had to clean. In each room sissy did all the work, supervised by Marta who was a much stronger boss than Jane. Often sissy would find himself bent over and being spanked for slovenly work. Eventually the five rooms were done to Marta's satisfaction and they returned to sissy's room.
When they got there Jane was untied and Marta told her that her training skills needed improvement. Marta then took a seat and told Jane to take off her shoes and give her a foot massage. She went to to say that Jane should have checked with her first before turning a guest, even a sissy one, into a free maid. The cleanliness of the hotel after all was Marta's responsibility and she would get in trouble if standards slipped. Jane apologised for not consulting Marta first when she found sissy's original uniform. |
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By (user no longer on site) OP
over a year ago
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Martha then beckoned sissy to go over her knees and receive a spanking for his bad cleaning. As she was spanking him she said "in future MrJxxx when you come to this hotel or any other in the chain I even expect you to let the head of housekeeping know and make sure you pack your uniform, is that understood?". Not knowing what to say sissy just nodded, thinking he could forget about it once he went home tomorrow.
When his ass was nice and red he was told to stand against the wall and for Jane to take his place over her knees. Once Jane had been punished sissy was ordered to strip to his underwear and lie on the bed. Under Martha's supervision Jane tied him tightly with the tights and gagged him. They then left him to sleep.
As he was trying to sleep sissy reflected on the past few days and figured it would all be over tomorrow. In the morning Jane came and released him and sent him to breakfast. When he came back to clean the room Jane informed him that Martha and her would be waiting in his room at three when his course ended and not to be late. |
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By (user no longer on site) OP
over a year ago
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When he arrived back at his room at three both Martha and Jane were waiting as he had been told. He was ordered to strip to his underwear, which today consisted of red panties and cami. When he had done so he was sat in a chair and tied to it. Martha looked at him and said "Mr Jxxx your time with us is not over just yet. We have a busy weekend's work ahead of us and your services are required. Before you think of arguing back think of what we can tell your bosses"
Totally taken back but knowing she was right, sissy just listened as they outlined the plan of action. Shortly sissy would get dressed as male and check out of the hotel as he was expected to. When he had done so Jane would meet him and take him to one of the staff bedrooms where he would spend the weekend. From six pm this evening until 2pm Sunday afternoon he was just another maid helping clean the hotel rooms. Martha and Jane would keep a strict eye on him and ensure he behaved.
They then untied him and let him back his bags and go check out. As arranged Jane was waiting for him and showed him to his new room. As soon as they got there she went through his luggage and took all his male clothes and his wallet, keys and id. She then told him to bathe and shave his body hair off and be ready for work at 17.45. Quietly he just obeyed |
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By (user no longer on site) OP
over a year ago
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Martha arrived on time to collect him from the staff bedroom and led him up the back stairs to the fourth floor. She explained that there were twenty rooms on this floor and Jane and sissy were responsible for cleaning them all. There was a gasp from sissy when he realised the task ahead. Jane was in the first room and sent sissy to clean the bathroom. With the task ahead there was little time for chat. They quickly moved from room to room, with Martha checking their work as they went. On two occasions sissy was called back to clean spots he had missed.
After about an hour and five rooms down Martha said they could have a five minute break. While they rested Jane tried to apologize for getting sissy into this. He just smiled and said it was his decision to bring the uniform. It reminded him of the saying about being careful what you wish for. After their break they were back working and it took them two hours to do the next five rooms. Martha agreed to call it a night and said they would finish the other ten in the morning.
She led them both back to the staff room, had them strip and tied both of them up with tights. Jane was expecting to go home but Martha felt she deserved the same treatment as she had put sissy through. Both were gagged with dirty panties and left for the night. |
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By (user no longer on site) OP
over a year ago
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The next morning at 7am Martha arrived in the staff room to release them. Neither of them had managed much sleep. They were told to dress and have breakfast and then hurry back to the third floor. There were still ten rooms to clean and Martha had plenty of other jobs for them. They were soon back in the rhythm with Jane doing the bedrooms and sissy the bathrooms. This meant sissy was spending a lot of his time on hands and knees around the toilet. Most rooms were in an awful state and took a lot of cleaning.
After two and a half hours they had finally finished the floor and were allowed a five minute break. Once that was over Martha led them down to the back of the kitchen. When they walked in and saw the mountains of dishes waiting to be cleaned, they wanted to scream. Jane looked at Martha and asked where the kitchen staff were, to which the reply was they were off sick. Martha had offered two maids as replacement and decided on Jane and sissy. The job involved filling the giant dishwashers, emptying them when washed and stacking the crockery for use in the morning. There was a separate machine for doing all the glasses.
After an hour they did not feel they had made much of a dent in the mountains of dishes. The dishwashers took about 15 minutes to run each time and there were five of them. It was very tiring work filling and emptying them and stacking the crockery. Soon both Jane and sissy felt tired and their legs and arms ached. Jane felt she was being punished for taking advantage of sissy's desires and not informing Martha immediately. Jane had never had to do the dishes before now. It took them a good seven hours to finish and then they had to clean down the kitchen area. By the time they were done their uniforms were filthy and they were sweating. Martha arrived back and scolded them for the state they were in, as if she had expected the work to be done with immaculate uniforms.
They were taken back to the staff room and told to strip. Jane was instructed to launder the uniforms ready for the morning. As all his male clothes had been taken from him sissy was given a smock to wear for now. He still had not decided if bringing his uniform had been a good idea but he knew he had never worked so hard as he had in the last few days. Hopefully there were just a few hours of this treatment left. |
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By (user no longer on site) OP
over a year ago
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Martha figured that Jane had learnt her lesson so she was allowed go home that evening. Martha took sissy to get some food and then back to the room. She then sat down and put sissy over her knees and gave him a thorough spanking. As she was doing this she reminded him of his instructions for when ever he uses this hotel chain in the future. Once his ass was nice and red Martha got some tights and tied him up for the night.
Early the following morning she released him and told him to have breakfast. She then had him dress in his cleaned uniform and took him to the laundry room. There she showed him how to fill and put on the large washing machines and work his way through the large amount of bed sheets. Martha said she would be back later to check on him and that Jane was not working today. After a couple of hours he was already sweating. Martha came back and allowed him a quick break. It was then back to work for another few hours.
When there was only an hour before his train was due to leave Martha took him back to the staff room and let him change into male clothes. His possessions were returned to him and a suit carrier given to him for his uniform. He was warned to take very good care of it and not to forget to bring it again. Once he was on the train home he finally felt he could relax and think about the week's ordeal. He did not remember much of the course which was the reason he had gone in the first place. At home he just collapsed into bed after putting the uniform right at the back of his wardrobe. |
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By (user no longer on site) OP
over a year ago
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A couple of months went by and sissy had almost forgotten all about the ordeal in the hotel. He kept his nose down at work and kept himself to himself. His evenings were spent quietly or out with friends on the odd occasion.
One day he was called into the boss's office and told they needed him to train a couple of people at an office in a different city. It was not normally his role but he was considered an expert on the system involved. He was informed that it was would take the rest of the week and he would be leaving tonight. One of the downfalls of known to be single was having work change plans at a moment's notice. The company would put him in a hotel and the boss's secretary had all the details and his ticket. When he realised it was the same hotel chain he inquired about another hotel but was told the company had a good deal with this chain. He went home to pack what he needed and seriously considered leaving the uniform behind. At the last minute he decided was not worth the risk and packed it.
The train journey was uneventful and when he got to the hotel he just wanted to check in and relax. He totally forgot about informing housekeeping he was here and offer to help. He got to his room, hung up his clothes and just crashed on the bed. He must have fallen asleep for a while. When he woke he noticed an envelope had been shoved under his door with the name "sissy" written on the front.
Shocked he opened it and read the note inside which said "Mr Jxxx or sissy, I am very disappointed that you did not check in with housekeeping when you arrived as you were supposed to. For your sake I hope you have your uniform as we have a lot of work for you to do during your stay. One of our maids, a young lady called Zoe, will call on you at 7pm and you better be dressed and ready for work. Signed Mary head of housekeeping"
Not knowing what to say or do sissy looked at his watch and realised that he only had fifteen minutes to get ready. He quickly stripped, washed and put on the practical underwear and uniform. He was just fixing the apron when there was a knock on the door. |
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By (user no longer on site) OP
over a year ago
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When he opened the door there was a young lady, aged about twenty standing there. She was dressed in the normal maid uniform and her name badge read "Zoe". He stepped aside and let her enter the room. She looked at him and said "sissy at least you are dressed properly, you are in enough trouble with Mary as it is. Now come along as we have a lot of work to do. I hope you remember how to clean". Standing there shocked at being spoken to in such a manner by such a young lady, sissy pulled himself together and followed her out of the room.
She led him to a room three doors down and gave him gloves and cleaning products. Without having to be told he headed straight to the bathroom, got down on his knees and started cleaning the toilet and around it, then moving to the sink. He was surprised as to how quickly it all came back to him. He finished off cleaning the bath and then went to help Zoe make the bed. Before they left she checked his work, pointed out a couple of spots he missed, but was mildly surprised. They moved next door and repeated the process, doing it slightly quicker. Even after two rooms sissy was tired considering his morning work and the train journey. Not having any sympathy as she had been working since 8am, Zoe hurried him along to the next room which was in quite a state. It took them about an hour to clean it, but then Zoe said they were done for the night.
They headed back to his room where they found Mary waiting for them, with a stern look on her face. She asked Zoe for a report to which the reply was "a bit slow but ok". Mary summoned sissy to stand in front of him and explain why he did not check in on arrival. Did he not think that Martha would have passed the word along about the new sissy maid. Totally lost for words he stood there saying nothing. Seeing this Mary grabbed his arm and pulled him over her knees and bared his ass. Picking up a ruler she had brought along just for this reason, she started to wallop his ass. She outlined that for the length of his stay, apart from when at his office, he would be working in the hotel helping Zoe. Any mistakes or hesitations would be severely dealt with.
When she was finished sissy was told to strip to his underwear and put his hands behind his back. As Mary held him in place Zoe quickly tied his hands with tights. He was pushed back onto the bed and his legs were tied. They were then pulled back and tied to his wrists, hogtying him. A gag was added and he was left for the night. |
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By (user no longer on site) OP
over a year ago
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The next morning Zoe came to the room to release sissy so he could go for breakfast and then to his day job. He was told to be back and changed by seven pm in order to clean the same rooms as last night. They needed to be done a lot quicker than last night. As expected sissy found it a bit difficult to concentrate at work but managed to get through the day. Rushing back to the hotel he grabbed a quick bite and then got changed. While he was waiting for Zoe his room phone rang and Zoe explained she was detained and he was to head to the first room. She had left some cleaning products there for him and the door left unlocked for him.
He nervously headed out into the corridor and to the room in question without being seen. He put on the gloves, got down on his knees and started cleaning all the stains around the base of the toilet. Who ever had occupied the room did not seem to be able to hit the target properly. He then stood to clean the sink and bath. Just as he was leaving the bathroom he heard the main door opening. He was expecting either Zoe or Mary but was shocked as a man entered the room. When he saw the maid uniform he initially thought nothing until he read the name tag of "sissy".
The room occupant just looked at sissy and asked what the hell was going on, was he a thief or what. Struggling to find something to say, sissy muttered that he was just cleaning and was under the impression the room was empty. The man just laughed and asked when the hotel starting hiring sissy boys as maids. He headed to the phone to ring security but sissy chased after him and begged him not to. As the man was standing there phone in hand, sissy got on his knees and offered to please him if the man would put down the phone. |
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By (user no longer on site) OP
over a year ago
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The man looked down on the little sissy on his knees, thought for a moment and put down the phone. He told sissy to open his flies and take out his cock. Never having done this before sissy nervously unzipped the man standing above him and let his cock flop out. Before he could start to suck it the man took off his tie and used it to tie sissy's hands behind his back. He then took sissy's head in his hands and started to face fuck him. He was shoving his cock in and out and sissy was trying not to gag. They soon got the rhythm right and the man sighed as he used sissy's mouth.
All of a sudden the door opened and in walked Zoe. She looked at what was happening and asked what on earth was going on. She had come looking for sissy as he was taking too long to clean the room. As his mouth was full of cock sissy could say nothing. The man explained that he had come back to his room, found sissy and thought he was a thief. He was about to ring security when sissy begged to pleasure him. He carried on face fucking sissy as he said this and then exploded down sissy's throat.
He cleaned his cock on sissy's face and untied his hands and sissy got off his knees. Zoe told sissy to clean his face and move on to the next room double quick. She then thanked the guest for his understanding and hoped sissy had pleased him well enough. She then left to help sissy clean. |
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By (user no longer on site) OP
over a year ago
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Zoe quickly caught up with sissy in the next room. He was busy cleaning the bathroom as if he was trying to forget what had just happened. It was the first time he had ever given oral to a male but could not have let security get involved. Zoe quickly cleaned up the bedroom and they moved on to the last three rooms of the night virtually in silence. They got the rooms cleaned without further hassle.
When they got back to his room sissy collapsed on the bed, still saying very little. Zoe tried to comfort him, saying he had done the right thing in difficult circumstances. Shortly later Mary arrived and asked if everything was ok. Zoe briefly explained what she had witnessed and sissy quietly explained the circumstances behind him been on his knees in front of a stranger. Mary thought about what she was told but figured they were lucky the guy was so willing to be pleased. If he had rung security it would not just have been sissy who would have been in trouble. She congratulated sissy on dealing with the situation. She explained what they were doing was a bit unusual so they needed to be more careful. She asked sissy what his first bj giving was like and if the man was satisfied. Not really knowing for sure sissy just replied that the man had shot a lot of cum down his throat and it tasted funny. Mary just smiled and said sissy would get used to the taste. She then had him strip to his underwear and tied him tightly to the bed. She removed her panties to use as a gag and then Zoe and her left the room so he could sleep, or at least try to. |
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By (user no longer on site) OP
over a year ago
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As sissy tried to sleep he reflected on what had happened over the last two nights. He was dreading on the next two nights of this trip especially if he bumped into any other male guests. A very restless sissy was released in the morning by Zoe and headed off to his training. Somehow he managed to make it through the day and grabbed a quick bite on the way back to the room. When he got there he saw yet another note from Zoe. He was to get dressed and head down the back stairs to the laundry room. Thankfully he did not meet anyone and Mary was waiting for him in the laundry.
Mary led him over to the ironing board, saying that there was little chance of anybody catching him here. There was a large pile of pillow cases waiting to be ironed. To ensure he did not wander too far she used a pair of tights to hobble his legs and left him to it. He started in on the pile and was soon sweating. It did not seem to him as if he was making much progress. Mary came back to check on him and was not overly impressed. Moving the iron out of the way and bent sissy over the board. Lifting the bottom of his uniform up she administered 20 hard spanks to each cheek. Letting him back up she warned he better get on with it as he was not getting to bed until the pile was done. That took him another three hours and he finally got to bed at one am. |
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By (user no longer on site) OP
over a year ago
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After managing a few hours sleep sissy headed down for breakfast and then to the office to finish training the new guys. He was somewhat relieved that he only had one night left in the hotel but also nervous about what Zoe and Mary may have planned. When he got back to his room there was a note telling him to be ready promptly at seven and that there was a long night ahead. He sighed to himself and yet again regretted bringing the cheap Ann summers maid uniform on his first trip. Look at all the trouble it had got him into.
He was sitting on the bed dressed at seven when Zoe opened his door with her pass key. With little more than a glance she told him to come along and led him to the master suite on the top floor. He had never seen a room so grand and in such a state. There were two bedrooms, two bathrooms and a living room. Taking up some gloves and cleaning products he headed for the first bathroom which was filthy. Obviously the more money guests had the more mess they felt they could make. There towels all over the floor and in the bath. He started by gathering them all together and putting them in a laundry bag. He then got down on all fours and scrubbed the floor around the toilet and then moved on to the toilet itself. Then it was time to tackle the sink and bath. He heard Zoe shouting at him to hurry up. Thinking this room was as clean as it could be he moved in to the other bathroom, which looked in a worse state. The two bathrooms took him almost an hour and a half to clean by which time Zoe had almost finished the other rooms. She told him to go and collect the hoover and give the whole place a thorough hoover. She was going to drop off the dirty laundry which he would be cleaning and ironing later. |
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By (user no longer on site) OP
over a year ago
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When he was finally finished the suite he had to head down to the laundry to wash and iron the dirty sheets and towels from the suite before he could retire for the night. He could tell it was going to be another long night and was glad he only had a half day at work tomorrow. It took him about three and half hours to finish off and leave the laundry ready for use again. He crawled into bed and collapsed. As he was heading home straight from the office in the morning he packed his bags and headed down to breakfast. When he returned both Mary and Zoe were waiting in his room for him. As soon as he entered Mary beckoned him over and told him to take down his trousers and go over her knees. He tried to protest that he had to get to the office but she was having none of it. Realising he had very little option he did as directed and the black French knickers he had decided to wear to work were on show. He went over her knees and the panties were pulled down. Mary started to administer 50 hard slaps to each cheek, reminding him that in future he checked in with housekeeping every time he checked into one of their chain, whether it was for work or for pleasure. Every head of housekeeping had his details and would be alerted as soon as a booking was made. If he did not notify them on arrival there would be severe consequences to pay. When she was finished with her slaps he was put over Zoe’s knees so she could administer some as well. When he was finally allowed to get dressed and sort himself his ass was stinging and it would be reminding him all day of his predicament. He finally got to the office, did his last bit of training and headed back home, hoping work would keep him at home for a long time to come. |
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By (user no longer on site)
over a year ago
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This is a beautifully written story and desiring to dress does not always have to be about sex. Though I understand that some, myself included, do like to dress, and submit, for sexual reasons |
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By (user no longer on site) OP
over a year ago
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After finally arriving home and unpacking, sissy relaxed in front of the TV and reflected on how his life had changed. He had planned to spend the weekend chilling out and preparing for work on Monday. About eight pm there was a knock on his door which surprised him as he rarely had unexpected visitors. He was even more surprised when he opened it and found Zoe standing there. She smiled at him and said "Hello Mr Jxxx and may I come in please?". Taken back it took him a minute to react and he stepped aside to let her in and closed the door. Wondering what on earth she was doing here and what she wanted, he followed her into the living room. When he came into the room she looked at him and said "this must be a bit of a shock to you but I can explain. However before I do I think you need to change". "I appreciate you are at home but we both know that you are a sissy so why don't you go along and put on that Ann summers maid uniform that started all this trouble".
Standing there with his mouth open sissy did not know how to react while deep down he wanted to ask Zoe to leave. He assumed she had got his address from the hotel system and did not know what other information she had. With a stern look from her he left the room and came back ten minutes later dressed as she instructed. She smiled and said that he looked much better and to sit down. She went on to explain that she had been offered a new opportunity in the chain's branch in his home town and was starting there on Monday. It was only when she was checking something out on the computer system did she discover the coincidence. She further explained that once she started work she would be calling on sissy maid's assistance from time to time. After hearing this sissy tried to object stating that it was too close to his work and his friends and he could not risk being discovered. She just laughed and told him that he really had little choice about it. He lost control the moment his maid uniform was found on his first hotel visit. In his local town he would kept behind the scenes and not interact with guests but he would be kept busy. She would pick him up at 11am the following morning to take him and introduce him to her new boss, Anne. |
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By (user no longer on site) OP
over a year ago
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When the next morning arrived sissy thought it would be the same as had been happening – he would meet the head of housekeeping and find out when she wanted him to help clean the hotel. Little did he know what was really going on and how set up he had been. Ever since Zoe had caught him sucking off the guest to avoid being caught, an idea had planted in her head and she had purposely sought this move. She knew Anne from old and knew that she would be up for the new venture. She arrived to collect sissy and bring him to the hotel. They went through the staff entrance to reduce being seen and went straight to Anne’s office. When Anne met sissy she smiled at Zoe and agreed that he would be perfect for what they had in mind. Having no idea what they meant sissy would just have to wait and see. Anne told him to meet Zoe at the staff entrance tomorrow night at seven pm and to bring his ann summers uniform with him. This last bit really surprised him as he had been told before it was not good enough for the hotel but Anne told him not to worry, just be on time.
Scared about what was going to happen sissy was nervous as he waited for Zoe the following evening. When she arrived they headed up the back stairs to a room on the top floor. Zoe told sissy to get changed while she prepared something. Once he was dressed, feeling more foolish than ever, he was led to a small closet in the back room. He was told to kneel down facing the door. When he did so Zoe used built in chains to lock around his wrists and ankles, hence keeping him in place. She finally added a collar and leash which was hooked to a bolt on the wall. The final piece was a ring gag which kept his mouth wide open. When the door was closed sissy saw that there was a hole in the door right at the level of his mouth. It finally dawned on sissy that he had been turned into a glory hole. Zoe smiled and just said that his lips were much better to use than his cleaning skills. Any time a cock came through the hole he was to suck it and swallow all the cum. The door would be locked so there was no escape and no one could get in to hurt sissy but he needed to do a good job.
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By (user no longer on site) OP
over a year ago
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A few minutes after she left Zoe came back into and removed the gag and changed the wrist chains so sissy could use hands to massage the cocks. When all was finally set the first cock came through the hole. It was quite thick but small. Sissy first licked the tip of the cock and then took in his sissy mouth and started to suck it. After a few minutes there was a sigh from the other side of the door which encouraged sissy to keep sucking. Shortly sissy got his first load down his throat. The cock was removed and a few minutes later another one took its place. This one was thicker and bigger. Sissy started to wank it and then took what he could in his mouth without gagging. With one hand he continued to wank as he sucked the big cock and felt it growing in his mouth. After a while the guy groaned and erupted down sissy's throat. |
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Sounds good I like to be used
