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sissy meets a domme for lunch
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By (user no longer on site) OP
over a year ago
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It started off quite innocently and simply. He had been following her on twitter for a while, just liking some of her comments and pictures, with very little one to one interaction. He knew that she was younger than him and more than likely had no interest in him but even twitter interaction was better than none. Then it changed.
She posted some innocent comment about liking pizza and wanting to go out for one over the next couple of days. When he saw this an idea came to mind and he messaged her and asked if she would consider meeting for lunch. He wanted nothing else but the chance to chat and would be happy to cover the cost of lunch if she was agreeable to this.
They swapped a few messages and then finally came the dreaded question “why would he offer to buy a complete stranger lunch”
He could lie and make up some reason but decided honesty was the best policy and admitted that he was a sissy and he found most women, especially younger women intimidating. She asked a few questions about this as she had never heard the term before but seemed to be getting more and more interested.
She mentioned that if she did agree to meet she would insist that he was dressed as much as a sissy as he dared do in public. This idea scared him as he had kept this side private for so long and was worried about the reaction. They came to a compromise that he would wear pink panties, female jeans, tights and a neutral top. Before he set out for the lunch he had to send a picture of the panties and tights and he was not allowed to wear socks over the tights. He was worried that he was getting in over his head but he agreed. She also stipulated that she would be ordering for both of them and that he of course was picking up the bill. They arranged to meet outside a local pizza restaurant the next day at 2pm. He was hoping the restaurant would not be too busy.
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looking forward to reading this . |
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By (user no longer on site)
over a year ago
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Oh love this idea |
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By (user no longer on site) OP
over a year ago
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The next morning he awoke nervous and excited. After doing a few things around the house it was time to get ready. First went on the pink panties and tights and proof picture sent as agreed. The jeans, shoes and teeshirt followed and he was both glad and sorry she had not suggested a bra. He got to the pizza restaurant early as he hates keeping people waiting. He was wondering whether she would show or not as he had a couple of non shows in the past.
It had just gone past two pm when a young lady walked up to him, wearing a blouse, short skirt and ankle boots. He smiled and told her it was nice to meet her and thanked her for coming. Before they went into the restaurant she told him to lift up the leg of his jeans so she could see the tights and prove he had not worn socks over them.
Slightly embarrassed he did as requested and then held the door open and followed her into the restaurant.
A waitress approached to seat them and handed them two menus. Once the waitress had left, she took his menu stating that he would not be needing it. Unsure what was happening he just sat quietly as she perused the menu and made her choice.
When the waitress came back she ordered one large Hawaiian pizza and two salads, one large and a water. The waitress checked if that was all and with a quick look at his companion, he just nodded. When they were alone she looked over at him and told him that he was a good sissy for not making a fuss. He did not need lunch. It should be enough that he was in her company. There was little he could say to disagree even if he was quite hungry and hated salad.
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By (user no longer on site)
over a year ago
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Such a good start and the possibilities endless  |
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By (user no longer on site)
over a year ago
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By (user no longer on site) OP
over a year ago
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While they waited for lunch Jane (as he found out her name was) asked him a few questions about being a sissy and how long etc. He gave some information but tried to hold some back due to the humiliation he was feeling, but she kept pushing for more.
Eventually the waitress arrived with the food and she placed the large lovely pizza in front of Jane along with a salad and a . The glass of water and other salad was placed in front of him. After checking all was ok the waitress walked away and left them to. He looked lovingly at Jane’s pizza but knew there was no chance she was going to share it.
Jane quickly looked around the quiet restaurant and seeing her chance, she took up his salad bowl and spat in it, saying that it looked a bit dry. She then placed it back down and told him to tuck in and make sure he ate it all as she started on the pizza. There was a huge difference in the look on their faces, hers being full of glee and his being full of horror. He hated what he was eating but realised he had little choice and had brought this on himself.
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By (user no longer on site)
over a year ago
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By (user no longer on site)
over a year ago
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By (user no longer on site)
over a year ago
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Keep it coming |
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By (user no longer on site)
over a year ago
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Mmmm this could be fun |
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By (user no longer on site)
over a year ago
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By (user no longer on site)
over a year ago
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Looking forward to more of this story. |
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By (user no longer on site)
over a year ago
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More please,mmmmmmmmmm  |
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By (user no longer on site)
over a year ago
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This is a very very good story xxxx please continue xx |
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By (user no longer on site) OP
over a year ago
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As he tried to eat the salad Jane started on the lovely pizza and made sure he knew how much she was enjoying it. As they ate she asked him more questions about being a sissy and why he was doing this lunch with her. He had to admit that he enjoyed the subtle humiliation of it and it had been something he had wanted to for a long time but always lost the nerve. She grinned at that comment and stated that she would be happy to do this again, and she would always choose his clothes and his food. He wanted to say no but deep down knew that was what he wanted so he just nodded.
The waitress came back to check all was ok and Jane replied that it was grand and the pizza was lovely. He had a small hope that she would not be able to finish the pizza and he may get the leftovers. Near the end of the lunch there were three slices left but Jane asked for a takeaway box.
When the waitress came with the bill Jane just pointed to him and stated that he was paying and told him to give the waitress a decent tip. He did so silently and slightly embarrassed. As they left he picked up the takeaway box and followed Jane out of the door. She led him to a secluded spot and told him to hand over the box, thank her for lunch and to kiss her shoes. All of which he did as if it was an out of body experience. |
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By (user no longer on site) OP
over a year ago
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Over the next few weeks similar lunches were arranged. For each one Jane decided what he wore under his male clothes (to pretend he was a real man) and he sent photo proof. At every restaurant she ordered something lovely for herself and usually a salad and water for him. He had to sit there and watch her enjoy her lunch while he ate a dry salad. Every time he was told to give the waitress a good tip.
Over the lunches Jane quizzed him and learnt a lot more about his secret passions and secret life and was deciding whether she wanted more out of this than just the chance to humiliate him over lunches. The one thing she did decide on was that he was to remain chaste unless she gave permission. Any time he wanted to cum he had to text her and beg permission which he was warned would rarely be given. If he got a hard on he had to dink it in cold water or ice to get rid of it as sissies did not deserve hard ons. |
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By (user no longer on site)
over a year ago
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By (user no longer on site)
over a year ago
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Wow |
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By (user no longer on site) OP
over a year ago
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The next meet was going to be slightly different. He was told to meet Jane at Merry Hill as they were going shopping for clothes for both of them, to show their new position. He was to be dressed male but in pink panties, he was not to say a word and just carry her bags for her. She turned up wearing a short denim skirt, ankle boots and a teeshirt.
The first shop they went to was a young women fashion store where Jane bought some light summer dresses, short enough to show off her assets. They then went to a ladies shoe store where Jane got some 5 inch high heels and a pair of knee high leather boots, He almost fainted when he saw the boots, a secret passion of his.
They then went to a fancy dress store, though he was not sure why. Jane went up to one of the assistants and asked if they had any maid uniforms. The assistant nodded and showed them where they were and asked Jane her size. Without blinking Jane smiled and said it was not for her, it was for me as I had lost a bet with her. Going red in the face I stayed quiet as the assistant looked at me, smirked and then hunted out a uniform in my size. It was a traditional black and white one, with an over the neck full length apron. Jane loved it and told the assistant that we would take it. |
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By (user no longer on site)
over a year ago
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nice start, I look forward to reading more |
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By (user no longer on site) OP
over a year ago
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A few days later Jane got in touch and said that she was having a little party at hers for two close friends and that she needed a maid to serve. He was not sure if he wanted to attend but was not really given much option. He was told to be at Jane’s at 7 the following evening, to be properly shaved and to bring the maids uniform.
When he got there he was shown to a small bedroom to change into. Already on the bed were some breast forms. He was told to put on the white lingerie he had brought, insert the breast forms and then the uniform. Jane would be in to check on him shortly. As he waited for her inspection he wondered what he was getting into and what her friends would think. Apart from Jane this would be the first time anyone else saw him dressed as a sissy and he was nervous.
Jane came in and smiled as she saw him properly uniformed waiting for her. She handed him some five inch shoes to put on, which she then locked in place. She added a collar around his neck and declared him ready. His duties were to answer the door, greet the ladies with a curtsey and serve drinks and snacks. He was not to talk unless spoken to, everyone was to be greeted as Miss and he was not to drop or spill anything. Any errors would be punished in front of everyone.
Before he could react to all this the door bell rang and he was sent off to answer it. When he answered there was a young red headed lady in her mid twenties standing there. She looked at him with a shock that soon became a smile. He stood to one side, dropped a curtsey and said “Welcome Miss may I take your coat”. When the coat came off he could see that the red head was dressed in a white blouse, leather skirt and ankle boots. He led her into the living room and after finding out what drink she wanted, he prepared and served it. Just then the bell went again and this time the guest was an older lady with black hair. When her coat was removed she was wearing a black leather dress and knee high boots. He led her to the living room, served her a drink and then stood in the corner quietly as they all waited for Jane to arrive.
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oooh I like this story! cant wait! xx |
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I'm liking this story even more |
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By (user no longer on site)
over a year ago
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Great story |
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By (user no longer on site)
over a year ago
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By (user no longer on site)
over a year ago
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By (user no longer on site)
over a year ago
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getting good |
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By (user no longer on site) OP
over a year ago
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When Jane walked into the room she was dressed in riding boots, white jodhpurs and a white blouse and she carried a riding crop. The look on his face told her he was taken aback by her clothes and not what he expected for a social night in with some friends. She introduced her two friends, the redhead was Ann and the older lady was Simone, but of course to him they were Miss Ann and Miss Simone. She sent him off to get her a drink and then set out to explain what was going on.
Miss Ann and Miss Simone were very good friends of Jane and they often got together in the evening for drinks and a chat at one of their respective houses. There was little they did not tell each other and during one of these chats they discovered a shared interest in female domination and service with the added twist of humiliation and age difference. When he messaged her on twitter and they arranged the lunch, Jane had of course informed her close friends and they had been monitoring her progress with him ever since. Tonight was a chance for them to meet him, size him up and see if they wanted to be involved in her training of him and have him serve them. If he passed their tests he would be shared between the three of them. He did not know what to say but was tempted to run but knew that Jane held his clothes and the key to the shoes and the collar. |
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I’ve been to a similar social gathering x the poor maid is in for a surprise! |
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By (user no longer on site) OP
over a year ago
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Before the evening started properly Jane asked him to come stand in front of her with his hands on his head. When he had obeyed, she lifted the skirt part of his uniform and pulled down his panties. He was embarrassed as his cock was exposed to the other two ladies. Jane just smiled and then took a box that was handed to her by Simone. She explained to him that the first part of a sissy to control was his cock and even though she had ordered him not to cum she needed to be sure. She then fitted a chastity device around his cock and locked it securely. She showed him that there were three keys to it and each of the ladies would have one. She then pulled up his panties and corrected his uniform. He was told to get down on all fours and kiss the boots of each of the women in turn to signify that he accepted their control and power over him. Having followed the instructions he was then sent to the corner and told to face the wall with his hands on his head. He could only get snippets of the conversation as the women spoke quietly but figured they were talking about his training and how to progress it. |
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By (user no longer on site)
over a year ago
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thats horny |
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By (user no longer on site)
over a year ago
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By (user no longer on site)
over a year ago
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Good stuff |
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Fantastic .... can’t wait for more !! |
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By (user no longer on site) OP
over a year ago
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After about an hour he was summoned from the corner and led into the kitchen. When there he was handed some rubber gloves and told to wash, dry and put away the dirty dishes in the sink. This was a bit new to him as he used minimal stuff at home and not the mountain of stuff that was here. He figured it was going to take him a couple of hours and he was already tired and done in from the evening’s activities. He asked if he could be excused and let go home as he had to prepare for work tomorrow. Jane just looked at him and then walked over, grabbed him by an ear and led him to the kitchen table. She bent him over one end of it, lifted up his skirt and pulled down his panties. When he was in position she took the crop from her boots and started to whip his ass with it. She carried on for a good few minutes, making the ass red and sore. As she whipped she called him an ungrateful little sissy and how could he want to duck out now especially after the trouble the three of them had gone to and the pleasant evening they had. It may have not been the evening he was expecting but he turned up so somewhere deep down he must have been curious as to where it was going to go and what they were going to do with him.
Earlier in the evening before her friends had arrived, they had discussed what he could say if it was all getting too much for him. Rather than doing what was he agreed, he behaved like a spoilt brat and hence was being treated like one. When she had finished he was crying and his ass was very sore. He apologised and asked to be let up so he could get on with the work. Instead Jane removed the collar and the locks on the shoes. She told him to go get changed and go home. While there he was to think long and hard if he wanted what they were offering or if it was too much. Either way Jane and her friends would accept his decision as they much preferred doing this with someone who wanted it rather than someone who was being forced. She would contact him in three days for his decision.
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By *atexpvcTV/TS
over a year ago
chester/Merseyside |
Great story hope you accept??? |
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By (user no longer on site) OP
over a year ago
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He went home and tried to sleep but had a lot going through his mind, He went online to watch some porn but had forgotten about the chastity device and it became a bit uncomfortable so he gave up. Over the next couple of days he spent time pondering and wondering what to do, He was worried that it was all a bit much but he also knew that it could be some fun, as long as limits were discussed. When Jane contacted him for lunch in the same place they had first met, he still had not made his mind up but agreed to go talk to her. At first they had a normal conversation but as the food was served, Jane steered it around to why they were there. She apologised if they had gone too far the night at hers but she had thought this was what he wanted, especially with some of the stories he had told her. He did agree on that but reminded her that there was a difference between reality and fantasy and sometimes fantasies don’t work out well. He went on to say that he was intrigued though but needed to agree some conditions first. They carried on the discussion and agreed terms of the training. While they were waiting for coffee Jane placed a small box on the table, She said that it contained the key for the chastity device. If he did not want to continue just take the box with him when he left and there was no hard feelings. If he left the box he was to be Jane’s place at 7 pm the following evening. |
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By (user no longer on site)
over a year ago
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interesting |
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I like this .... Real experience shines through... |
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By *atexpvcTV/TS
over a year ago
chester/Merseyside |
Great keep it going |
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By (user no longer on site) OP
over a year ago
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After their chat and splitting the bill he left first with the box still on the table. He was unsure about it all but felt better after the discussions and was willing to give it a try. The following evening he was at Jane’s at 7 promptly. She answered the door dressed in a skirt and blouse and small heels and led him into the living room. She had agreed that for the first couple of weeks of training it would just be her, though she could keep the others informed as to how things were going. After a quick chat he was told to strip off and stand in front of her with his hands on his head. When he was ready she walked around him examining his body. She said that his body hair would have to go and she would undo the chastity device so that he could get rid of any hairs there. For the training period he was not allowed any male underwear unless there was an emergency, which he had to get permission for up front. At home he was to sleep in a negligee and had to sit when using the toilet. Twice a week he was to attend Jane’s house and do her dishes and vacuum for her. He would be provided with an apron for doing this rather than the full uniform. That was for special occasions when he was serving her and others. Any mistakes would be added to a demerit log and dealt with once a week.
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By (user no longer on site)
over a year ago
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Slow and hott |
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By (user no longer on site) OP
over a year ago
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The first couple of weeks training went well. He turned up on time, stripped down to just the chastity device and wore the apron over. On the first day he was shown how Jane expected things to be done, which was fairly new to him. As he lived alone and rarely had guests cleaning was not high on his priority so he was almost learning from scratch. The first couple of days earned him a few demerits as he was either too slow, did not clean well enough or made too much noise. Jane explained that one of the benefits of having a maid was being able to leave them get on with the work and not have to stand over them at all times and watch. This is where she wanted to get to but knew it would take time. At the end of the first week he was told to position himself over the end of the kitchen table, with his upper body resting on the table and his ass on show. Jane reminded him of his mistakes and caned his ass twenty times for them. This left him with a marked reminder to do better. By the end of the second week he had only earned fifteen strokes, which was a slight improvement. There then came an unexpected hurdle which at first Jane was not sure how to deal with. One evening she had a phone call from her sister asking if her twenty year old niece could stay for a few days as she looked into universities in the city. Jane wanted to help but was not sure about having sissy around while the niece was there, but she did not want to have a gap in the training as she was afraid that progress would be lost. |
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By (user no longer on site)
over a year ago
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Sexy student ????? |
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By (user no longer on site) OP
over a year ago
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The dilemma that Jane faced regarding the visit of her niece was complicated. She could annoy her sister by trying to put off the visit. She could stop the training of sissy for the couple of weeks. She could try and arrange the training around times she knew that her niece would not be in the house. She could be open and explain all to her niece when she arrived. It had been a few years since Jane had spoken to her niece so was not sure what type of young lady she had become and what her reaction may be. She may be horrified; she may accept it or may have no interest at all. Would it be better to tell her up front or run the risk of her discovering for herself? If it was the latter would her niece keep her secret or would she tell her sister about her freaky aunt. Jane had two days to decide before she had to let her sister know if Amy could come to visit. |
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By (user no longer on site) OP
over a year ago
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After a lot of thinking Jane decided that she could not give a good enough reason for Amy not to visit but she also decided not to say anything to sissy about the visit. She would just hope that they never met. So a couple of days later Amy arrived and was settled into Jane’s spare room. She had changed a lot since Jane had last seen her and grown into a very lovely looking young lady, who had an air of confidence around her. Over the next two days she was out most days looking at universities and getting to know the local area. She did not even attempt to make an effort to make her bed or help with the dishes, which normally would have annoyed Jane. Of course now it just meant more work for sissy to do who was sneaked into the house for a couple of hours while Amy was out. It was after the fourth day that Amy asked if she could have a word with Jane. They sat at the kitchen table and Amy asked about her bedroom and how every couple of days it was cleaned. She was surprised especially as she did not expect Jane to be cleaning up after her. She also mentioned how tidy the kitchen was though she knew that she often left it in a mess. Jane did not know what to say but just made some excuse about always been happy to do house work and the additional bits were only for a couple of weeks.
Amy said nothing else but did not seem convinced by her aunt’s answers and decided to keep an eye out over the next couple of days. On Friday as she was coming back earlier than expected she saw a man going into the house. At first there was nothing strange about this as she assumed it was just a friend of Jane’s. Rather than going in and disturbing them she headed back to the pub for a couple of hours. When she finally did arrive home the man was gone but she immediately noticed how tidy her room was and how clean the kitchen was. She started to wonder what was really going on. Did her aunt employ a male cleaner or was there something else?
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By (user no longer on site)
over a year ago
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Good stuff |
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Oh this is getting interesting  |
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By *iM4kinkMan
over a year ago
San Antonio |
"While they waited for lunch Jane (as he found out her name was) asked him a few questions about being a sissy and how long etc. He gave some information but tried to hold some back due to the humiliation he was feeling, but she kept pushing for more.
Eventually the waitress arrived with the food and she placed the large lovely pizza in front of Jane along with a salad and a . The glass of water and other salad was placed in front of him. After checking all was ok the waitress walked away and left them to. He looked lovingly at Jane’s pizza but knew there was no chance she was going to share it.
Jane quickly looked around the quiet restaurant and seeing her chance, she took up his salad bowl and spat in it, saying that it looked a bit dry. She then placed it back down and told him to tuck in and make sure he ate it all as she started on the pizza. There was a huge difference in the look on their faces, hers being full of glee and his being full of horror. He hated what he was eating but realised he had little choice and had brought this on himself.
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By (user no longer on site) OP
over a year ago
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It took a while but the inevitable was bound to happen. Coming home one day when she was not expected Amy walked into the house and heard someone in the kitchen. Expecting it to be her aunt she walked in to say hello and got a shock. Standing in front of the sink wearing what looked like panties and an apron was a male, who was busy washing the dishes. He was so caught up in his work he had not heard her come in but jumped and when she coughed and he turned around. When he did she could see that he was in his late forties and had suddenly gone very red in the face. She just looked straight at him and asked who he was and what he was doing there. He stammered and stuttered and did not what to say. She looked at him sternly again and repeated her questions – who was he and what was he doing in her aunt’s house. Just then as if by magic Jane arrived in from the back garden and took in the sight in front of her. She calmed sissy down and told him to go to the bedroom until she called.
She asked Amy to sit at the table and she would answer any questions that she had. Amy started off by asking who the man was and what was going on. Jane sighed and said that she had hoped not to have to have this discussion, especially as Amy was leaving in two days time. She quietly explained how she had met him and that she was training him on how to do housework and be of use to women. It may come as a shock to Amy but some men liked being under the control of a woman from time to time. Amy was a bit surprised but not necessarily shocked – she knew some people who were into kinky things, just never expected her aunt would be one. Amy asked how long it had been going on and when her aunt explained that it all started about six weeks ago, she was intrigued and wanted to know more. Before she continued her aunt begged her to keep this information to herself and not tell her mother. Jane explained that what she was doing was not hurting anyone and it was her private business.
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Oh this is getting interesting
So manny way it can go |
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By (user no longer on site)
over a year ago
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Love this |
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Think it could get very interesting |
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By (user no longer on site) OP
over a year ago
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Amy said very little as her aunt explained. When Jane was finished she turned to her and said that she guessed it was time for family secrets to come out. Amy explained she was not as naive as Jane thought she may be and that she was aware of the fetish world and what some people got up to in their private lives. She even had dappled herself from time to time. One of her reasons for choosing a university away from where her parents lived was so she could explore a bit more and find her place in the world. This did come as a bit of a shock to Jane as she had always been told that her niece was a goody two shoes and very innocent in the way of the world. Amy just laughed and said that is the impression she gave her parents but as the saying goes, “one should never judge a book by its cover”. If Amy had known how open Jane was she would have brought some of her outfits and toys with her on this trip. She agreed to keep Jane’s secret if Jane kept hers and if Amy was allowed to use sissy from time to time. While a bit scared at what may happen, Jane agreed as long as sissy did.
Jane summoned sissy back into the kitchen and told him to kneel in front of her. He was reluctant to do this in front of Amy but soon obeyed. Jane summarised their conversation and gave sissy two options. He could leave and never come back or he could accept Amy as his superior and she would have use of him when she visited. He looked at Jane and then at Amy and then decided. He bent down and kissed the feet of Jane and then kissed the feet of Amy, hereby signalling his acceptance of his place. Amy smiled and petted his head and told him from now on he was to address her as Miss Amy. He shivered a bit and replied “Yes Miss Amy”. Miss Amy then told him to take off her shoes and socks and to give her feet a massage. As he did this Amy and Jane discussed the universities she had visited and what would best suit her needs. It was as if sissy was not in the room.
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Love the thickening plot .... sissy’s Miss and Mistresses are going to have some fun !!!! |
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By *usie4uTV/TS
over a year ago
Havant |
"Amy said very little as her aunt explained. When Jane was finished she turned to her and said that she guessed it was time for family secrets to come out. Amy explained she was not as naive as Jane thought she may be and that she was aware of the fetish world and what some people got up to in their private lives. She even had dappled herself from time to time. One of her reasons for choosing a university away from where her parents lived was so she could explore a bit more and find her place in the world. This did come as a bit of a shock to Jane as she had always been told that her niece was a goody two shoes and very innocent in the way of the world. Amy just laughed and said that is the impression she gave her parents but as the saying goes, “one should never judge a book by its cover”. If Amy had known how open Jane was she would have brought some of her outfits and toys with her on this trip. She agreed to keep Jane’s secret if Jane kept hers and if Amy was allowed to use sissy from time to time. While a bit scared at what may happen, Jane agreed as long as sissy did.
Jane summoned sissy back into the kitchen and told him to kneel in front of her. He was reluctant to do this in front of Amy but soon obeyed. Jane summarised their conversation and gave sissy two options. He could leave and never come back or he could accept Amy as his superior and she would have use of him when she visited. He looked at Jane and then at Amy and then decided. He bent down and kissed the feet of Jane and then kissed the feet of Amy, hereby signalling his acceptance of his place. Amy smiled and petted his head and told him from now on he was to address her as Miss Amy. He shivered a bit and replied “Yes Miss Amy”. Miss Amy then told him to take off her shoes and socks and to give her feet a massage. As he did this Amy and Jane discussed the universities she had visited and what would best suit her needs. It was as if sissy was not in the room.
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Keep going please x |
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By (user no longer on site)
over a year ago
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Good stuff |
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By *atexpvcTV/TS
over a year ago
chester/Merseyside |
Mmmm woukd love this done to me.. |
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By (user no longer on site) OP
over a year ago
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While sissy was massaging her feet Amy started to ask Jane a few more detailed questions about the training. Was it just to train sissy how to clean or was it to involve any sexual and pleasure giving training as well. Amy was pleased to hear that sissy was kept chaste. She asked if Jane had started to train sissy’s ass yet, to which Jane replied no. She had thought about it but had not implemented the idea yet. Amy suggested that they start with a small plug and build up and that sissy should get used to having his ass filled at all times. Amy then asked Jane if she owned a strap on. Jane went a bit red in the face with this question from her niece but laughed and said that she did indeed, one that had not been broken in yet. Amy grinned and said no time like the present so why did Jane not go and put it on. Unsure for a moment, Jane went off and when she came back she was wearing the harness with a black 7 inch dildo sticking out the end of it. Amy told Jane to position herself in front of sissy and then told sissy to open wide and start licking the strap on. It was a bit embarrassing for sissy to be doing this in front of Amy, which was part of the fun for her. He took the end of the strap on in his mouth and started to roll his tongue around the end of it. Amy looked at him and exclaimed that it looked like sissy had some experience in O and she was looking forward to increasing this experience. |
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By (user no longer on site)
over a year ago
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So hot |
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By (user no longer on site)
over a year ago
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mmmmmm just what i'm looking for to brill story more please ?? |
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By *ubsteffTV/TS
over a year ago
Portsmouth |
Now the strap on is out, this is getting better! |
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By (user no longer on site)
over a year ago
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getting hott |
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By (user no longer on site)
over a year ago
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Carry on |
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By *atexpvcTV/TS
over a year ago
chester/Merseyside |
Do carry on as i want to be just like this person.. |
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By (user no longer on site) OP
over a year ago
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As Amy was due back home tomorrow evening she asked if she could borrow sissy for the day tomorrow to properly train him to her liking. Jane checked with sissy if he could get the free time and when he agreed she told him to be at the house at 11am. He would be left alone with Amy but would expect to be on good behaviour or else Jane would deal with him. Jane explained to Amy that sissy had a safe word and he was entitled to use it. Amy was fine with this and said she was looking forward to having sissy to herself tomorrow. 11am the following day sissy nervously arrived at the house and rang the bell. Amy opened the door dressed in trainers, tee shirt and denim skirt. She noticed a slight look of disappointment on sissy’s face and explained that it was important sissy knew his place, no matter what his superiors were wearing. He was ordered down on all fours and told to kiss Amy’s trainers and then crawl after her into the kitchen. Once there he was told to strip down to his chastity device and stand with his hands on his head. Amy positioned a chair in the middle of the floor and sat on it. She pointed to her knees and indicated that sissy should place himself over them. When he was in position Amy explained that punishment could be at any time and was a good reminder of the hierarchy. She told sissy to count and thank her for each spank and then applied the first spank. “One thank you Miss Amy”. The next one was applied to the other cheek, “Two thank you Miss Amy”. This carried on until Amy had applied fifty hard spanks to sissy’s cheeks which were now red. Amy told him to get up and bend over the table. She then approached and added some lube to her fingers which she applied to his asshole. When it was lubed she shoved a butt plug up his ass, making him squirm as it went in. “A sissy’s ass should always be full” explained Amy and “make sure you don’t lose it”. She then put a collar around his neck and attaching a leash she led him to the sink. |
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By (user no longer on site) OP
over a year ago
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Sissy was left to clean the dishes and put them away as Amy lounged around and relaxed. When they were all done he was told to stay there while Amy went to get changed. When she came back he gasped at the difference in her – gone were the denim and teeshirt and trainers and in their place were knee high boots, riding jodhpurs and a white blouse. Amy pointed to the floor and sissy immediately crawled over and kissed the top of each boot. Taking the leash Amy led sissy on all fours back into the living room. She sat on the settee and positioned sissy on his knees in front of her. She reached behind her and got out a new gag, which when fitted in sissy’s mouth it had a small steel tube sticking out. To this Amy attached an ashtray, immediately turning sissy into an imamate object. As the gag stopped all speech he just had to kneel there while Amy relaxed and smoked, dropping her ash into the ashtray. Even though the tube was hollow it did not allow the ash to travel into sissy’s mouth but the smoke got in his eyes and up his nose. Amy spent an hour relaxing on the couch and in this time went through three cigarettes, which meant the ashtray was full of ash and butts. She told sissy to hold out his hands as she detached the ashtray and placed it in his hands. She warned him not to spill any as he crawled to the bin to empty it and then clean the ashtray out. Luckily for him no ash hit the floor. She then called him back in front of her and removing the other part of the gag, she told him to spend time worshipping and cleaning her boots. This was something that he needed to get used and not just for her, but maybe for her friends as well, especially if she did move to this city for university. Having a local sissy bitch would definitely factor in her decision. |
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....hope she chooses Leeds University |
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By (user no longer on site)
over a year ago
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By (user no longer on site) OP
over a year ago
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When she was finished relaxing Amy figured that sissy needed some more oral training so she told him to crawl to her room and bring back her strap on. When he returned she put on the harness and positioned him between her legs. She set up some sissy porn on the laptop so they both could watch and told him to learn from what was happening on screen and practice on her strap on. After about thirty minutes his mouth was getting sore but there was no let up from Amy. She kept him at it for a good hour and a half, shoving the strap on further and further down his throat, often making him gag. She giggled at his attempts and derided him for not being as good as the sissy in the porn video they were watching. Eventually she stopped and released his mouth. He was immediately told to worship her boots again as a way of thanks for her training. This was the position Jane found them in when she arrived home, Amy dressed for riding and sissy licking boots. Jane asked Amy if sissy had been good and was disappointed when she was told that sissy had acted up. Sissy wanted to correct Amy on this but knew better to do so. He was ordered to get up and bend over the table with his ass in the air. Jane got some ropes and tied his wrists to the far end of the table which pulled him flat onto the table. She then collected one of the canes and stood behind him and administered twenty hard strokes. Due to their severity there was some stripes left across sissy’s ass and both Jane and Amy admired them and felt that sissy’s ass should always show marks of his punishment and training. This did not bode well for sissy. He was left tied to the table as Amy and Jane had a drink and then Jane helped Amy to gather her things and head home. Time will tell if Amy moves back to the city for university or if sissy would be left just trying to please Jane and her two friends. |
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By (user no longer on site)
over a year ago
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By *ogue78Man
over a year ago
Edinburgh |
Didn't think I'd like this... But a domme could be interesting.... |
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By (user no longer on site)
over a year ago
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getting hott |
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Time will tell very soon I hope |
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By (user no longer on site) OP
over a year ago
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Over the next couple of weeks Jane continued the training but also built on what Amy had started. She increased the size of the plug sissy wore and every couple of days she bent sissy over her table and used a strap on. Soon enough sissy was getting used to having his hole filled and it felt strange when it was empty. Jane also decided to make the cleaning a bit more challenging by adding linked wrist and ankle chains to sissy’s uniform. There was enough leeway to do the work but sissy struggled at times. If his results slipped Jane was not afraid to administer the cane and most visits ended with sissy having a striped ass. During this time there was no word from Amy and sissy was too afraid to ask if she was coming back, though deep down he hoped that she would be. The idea of serving Amy at university had got into his head and it made his poor little clit sore and hard in the chastity device. |
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Looking forward to more a always |
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By (user no longer on site) OP
over a year ago
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As this thread is almost full going to leave this story here.
May come back to Amy's use of sissy at uni another time |
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By (user no longer on site)
over a year ago
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Great story x |
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