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The shop

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By (user no longer on site) OP   
over a year ago

Peter had given up his job to follow his dream of owning a second hand book store. After searching around he found the perfect location in a small shopping centre and started to arrange the shop and get the books in. From when he was small Peter had always enjoyed reading and sharing that experience with others, swapping books and ideas.

The shop took off and Peter was relatively busy in there and building up a number of regular clients. One day a new customer came into the shop for a look around, and Peter noticed her immediately, mainly due to the boots she was wearing (another major interest from a young age). She looked in her late 20’s and was wearing a nice business suit. Peter assumed she worked in one of the offices near by.

He would have liked to have spoken to her but did not have the nerve. Thankfully the decision was taken out of his hand when she approached and asked if he had certain books. He was able to point her in the right direction and she found what she wanted.

She became a bit of a regular after that and Peter found out he was correct about his assumption of where she worked. He started to find it easy to talk with her, though always slightly flustered if she came in wearing boots.

One day she approached and asked if he had a certain book – for some private research she was doing. He did not have it in stock but said he could try and get it for her – she was grateful and gave him her mobile number in case he laid his hands on the book. A few days later he managed to track down the book and decided to have a look at it before handing it over. He was surprised at the contents as it was not the book he would have expected his customer to be reading – it was all about unusual sexual practices.

A day or so later she popped in to collect the book, after he had contacted her. He said nothing about reading the book but had taken the chance to slip a little note between the pages regarding his own interest in certain unusual practices.

Later that same day she popped back nearer closing time and asked if he had time for a coffee. Taken a little by surprise he agreed to close up early and go for a drink with her, not knowing what she wanted to talk about. Before they left, she handed him a bag and said to go put the contents on. Looking in the bag he was amazed to find a pair of pink lacy panties – he looked at her as if to ask what she meant, but she only said Do It – you know you want to.

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By (user no longer on site)
over a year ago

Love where this is going

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By *oventry4biTV/TS
over a year ago

coventry

Looking forward to hearing more

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By (user no longer on site)
over a year ago

Tell us more

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By *cotFit4funMan
over a year ago

Kettering

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By (user no longer on site)
over a year ago

Very interesting start

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By (user no longer on site)
over a year ago

Very good start.

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By (user no longer on site)
over a year ago

Looking forward to more.

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By (user no longer on site)
over a year ago

Go on please do continue.

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By *r 007Man
over a year ago

harrogate

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By (user no longer on site)
over a year ago

Yes.........

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By (user no longer on site) OP   
over a year ago

Realising that she had found his note and taken his passion to heart, he could either tell her she had made a mistake or follow her instructions – he decided to do the latter and see where it led. Shortly later they were sitting in a secluded bar drinking and chatting. To be fair she was doing most of the talking as he was too nervous to talk. She explained how she had found his note and was intrigued so had done some further research online and came up with a plan. She also explained that she knew how he got flustered whenever she wore boots into the shop and now understood why. She then blatantly said that she had always wanted a submissive sissy and it was her idea to turn Peter into her new play thing – whether he wanted to or not………..

The one thought that entered Peter’s head was the warning he had heard many times before “be careful what you wish for”. He had often dreamt of this moment but now that it was staring him in the face, he did not know what to do at all. Even though he thinks it was too late to do anything but agree, after all he was sitting here in lacy panties just because she had told him to.

She looked at him and smiled and said “ Don;t be too scared – you know you want this to happen and if you behave yourself, both of us will learn a lot and may actually enjoy it”. She went on to explain that she was taking Peter shopping tomorrow for a range of panties and female under garments- from now on he would be wearing them every day and she would be checking. When they were in public he could call her Jean, but in private it was always to be Miss Jean. Peter just nodded, not knowing what else to do or say. Maybe she would soon tire of this and it would all be a bad dream. If not what is the worst that can happen.

Jean tells him to pay for the coffees and that she would be around at the shop at lunch time tomorrow to take him shopping. He better be there and better be wearing the panties he has on now or he will not like the consequences. She also told him that he was not allowed to pleasure himself that evening, in fact he was not allowed to do so again unless she permitted it, which would not be very often.

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By *ree guyMan
over a year ago

Fleetwood

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By *cotFit4funMan
over a year ago

Kettering

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By *hrissy TvTV/TS
over a year ago

birmingham

Love it can’t wait for more

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By *r 007Man
over a year ago

harrogate

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By (user no longer on site)
over a year ago

my cock is starting to twitch

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By *100Man
over a year ago

Essex

I love a dominant woman tell me more please

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By *dsindyTV/TS
over a year ago

East Lancashire

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By (user no longer on site) OP   
over a year ago

After a very restless night with not much sleep, Peter arrived to open up as normal, still wondering what to do. Being too scared to do otherwise, he was dressed as ordered and also he wanted to see how things would pan out. He had often ran from opportunities like this in the past and needed to see how far this could go. Promptly at one, Jean arrived, dressed in a very sophisticated business suit with black knee high boots. She smiled at the impact her outfit had on Peter and told him to close the shop and follow her.

She led him to her car and told him to get in and after about a 15 minute drive, they had arrived at an out of town shopping mall. There were a few shops around, including a very exotic lingerie shop and an adult toy shop, the type of shop Peter had walked past from time to time but never had the nerve to go in. First stop was the lingerie stop. When they entered, a young female sales assistant came up and asked if she could be of assistance. Peter stood open mouthed as Jean explained that she needed several pairs of matching under garments and stockings for him. The assistant did a double glance at him and looked back at Jean. Realising she was being completely serious, she stifled a giggle and asked what size. Peter stammered that he was not sure as it was not something he bought very often. The assistant took them to a changing room and asked Peter to remove his outer clothes so she could measure him. He looked at Jean and baulked at the idea – no one else had ever seen him in female underwear and he was embarrassed. Jean just stared at him and did not have to say a word, but slowly he started to take off his shirt and trousers. The assistant could not help but giggle at the pair of pink lacy panties he was wearing. Returning to her professional mode, she got a measuring tape and took the measurements needed. Peter was going to dress again when Jean said he may as well leave them off – he was going to model some new lingerie for her and the assistant.

A few minutes later the shop assistant came back into the room, her hands full of bras, panties, slips and garter belts. Handing a set in white to Peter, she suggested he try them on. As Jean saw a moment’s hesitation in him, she walked over and quickly slapped him soundly across the face. “You are a sissy and a sissy obeys all women, got it sissy? She almost shouted at him. The assistant’s face was almost as red as the mark left on Peter’s face, but deep down this was money for the shop and would make an interesting tale to tell her friends. With her help, Peter got dressed in the lingerie and the stockings and stood and modelled them for Jean and the assistant. They were both impressed with the fit, though Jean said that the body hair would have to go. Peter was told to put his shirt and trousers back on top and go and pay for all the nice new underwear.

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By *hrissy TvTV/TS
over a year ago

birmingham

Love it can’t wait for the next part

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By (user no longer on site)
over a year ago

All my sissy dreams in this story. So looking forward to the next instalment.

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By *r 007Man
over a year ago

harrogate

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By (user no longer on site)
over a year ago

Fantastic.

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By (user no longer on site)
over a year ago

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By *atehantsTV/TS
over a year ago

Petersfield

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By (user no longer on site) OP   
over a year ago

While he went to do this, Jean and the assistant had a little private chat which Peter may find out about another time. Once finished, Jean then took Peter to the adult store next door for some further supplies, and perhaps some more humiliation for Peter.

Peter’s eyes opened wide when he first set foot in the adult store and found it full of toys, clothes and equipment to satisfy all types of fetish needs. Jean, seemingly knowing where she was going, led him to an area at the back, which seemed to be full of bondage toys like collars and cuffs. As they got there, they were approached by a shop assistant (was it coincidence that they were all young females), who asked if she could be of assistance. Knowing not to say anything, Peter waited for Jean to speak. When she did, she explained that she wanted a full steel set of collar, wrist and ankle cuffs for her little sissy and that she wanted them all lockable. As if this was a normal day in the shop for her, the assistant took some measurements and went off and quickly came back with what she thought Jean wanted.

Jean asked the assistant to place the collar and cuffs on so she could check the sizing, and Peter just stood there and let it happen. They were a perfect fit and Jean asked also for a leash, a gag and a hood. While these were being retrieved, Jean took Peter over to another area of the shop that had various sex toys and plugs. Peter also saw some chastity devices, never having seen them real life before had come across enough pictures online while researching what up to now had been his secret hobby. When the assistant reached them, Jean calmly said that she wanted a chastity device. She looked at Peter and he knew what was expected – he took down his trousers, even though it meant displaying the stockings and panties under. The assistant tried to stifle a giggle at the sight, but failed. She had a look and then went behind the counter and showed Jean a chastity device she thought would be appropriate. Jean nodded and suddenly the device was locked around Peter’s cock and the key, of course, was given to Jean.

Once Peter had rearranged his clothing, Jean headed to another part of the store and picked up some toys that she felt may be needed in the training, but these she kept hidden from Peter for now. After paying for everything and leaving the shop with a few bags, they returned to the car and put everything in the boot. Jean then suggested they go for a coffee and discuss what was going to happen now and what she expected. Peter just looked at her and really wanted to say something, but bit back and just followed her to a cafe. After their order was taken, Jean smiled at Peter and mentioned that he must be a bit shocked as to what had just taken place. She said that he may not have expected it but deep down, must have wanted it as he had not put up much of an objection.

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By *r 007Man
over a year ago

harrogate

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By (user no longer on site)
over a year ago

Very good.

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By *ondon258963Man
over a year ago

Bishops Cleeve

Very nice

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By (user no longer on site)
over a year ago

Think I'll stick with 'Fly Fishing' by J R Hartley for the moment....

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By (user no longer on site)
over a year ago

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By *ilberryMan
over a year ago

Scarborough

Book Marked!

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By *exysurferMan
over a year ago

Bromley

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By (user no longer on site)
over a year ago

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By *arriedfun51Man
over a year ago

Northern Ireland

keep going pls,am rock hard here

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By *vhazelMan
over a year ago

Ely

Fab

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By (user no longer on site)
over a year ago

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By *hloe kinkyslutTV/TS
over a year ago

colchester & London

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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

Thanks for the mostly positive comments

First time trying anything like this so will see how it goes

There is a bit more but in no way a finished story

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By *r 007Man
over a year ago

harrogate

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By (user no longer on site) OP   
over a year ago

Peter was not sure as to how to reply to this but just said that he was curious as to how far Jean was going to take things. Jean smiled and stated that when she was finished, Peter would be a well trained little sissy bitch and maybe even would have learnt how to please men as well as women. This totally shocked Peter as due to his upbringing and beliefs, he had never considered doing anything sexual with men, but knew that it formed a large part of many of the stories he had read. Jean outlined for now that she would expect Peter to wear full female underwear under his male clothes every day and he was to sleep in a nightie. The chastity cage would stay on for the foreseeable future as a form of control and to ensure Peter learnt his new role quickly.

The next couple of weeks continued to feel like a dream for Peter. He had kept this side of him hidden for so long and now all of a sudden, three young ladies knew he liked to be controlled and wear female undies and clothes. He continued to dress in matching bra and panties each day as he never knew when Jean would drop by to check. She had warned him of very severe consequences if she ever caught him without the proper undergarments and though he was curious what she meant, he was not sure if he wanted to find out.

About two weeks after the shop visits, Peter was at work, dressed in pink bra and panties under male clothes, He had picked a dark shirt to wear, hoping the bra would not show through. Business was quiet in the shop, with a couple of people browsing around. One of the ladies looked familiar but Peter could not remember where he knew her from. She kept throwing glances at him as if she wanted to approach and say something but did not. Eventually it was only the two of them in the shop and she came up and asked how the bra was feeling. Taken aback and worried she had noticed he went red in the face. The young lady introduced herself as Laura and told him that she had sold him the underwear he was wearing. It then clicked that Jean must have told Laura where he worked.

Laura smirked at the realisation and told him that indeed Jean had and suggested Laura drop in any time she was nearby to check up on the sissy Peter was told to lift his shirt so Laura could inspect the bra and she said the colour was quite appropriate. Just as she was leaving, she told Peter to keep tomorrow lunch time free as they had an appointment, but said nothing more about it. Peter did not know what to think but there was little he could do apart from wait until the next day.

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By (user no longer on site)
over a year ago

Fantastic xx

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By (user no longer on site) OP   
over a year ago

Promptly at one the next day Laura showed up and told him to close the shop and follow her. After a walk they ended up in a beauty salon, which of course was the first time Peter had ever been near such a place. They walked in and Laura said to the receptionist that they had an appointment set up for an all over waxing. Peter had been shaving his hair as Jean had instructed but obviously they did not think this was enough. They were led into a separate room and Peter was ordered to strip and lay on the bed. Shortly the technician walked in, had a quick chat with Laura and then started to apply wax to Peter’s chest and legs. After they were done, with some pain, Peter was told to turn over and the back and back of legs were done. That only left the private areas but they were not going to escape. The technician could not help but giggle as Peter had to ask Laura to remove the chastity device so that area could be worked on. She also giggled at the size of Peter’s cock as she removed all the hair around it and his backside. Soon they were done and Peter was as hairless as the day he was born. Laura explained that a monthly appointment had been set up to keep this up to date and that Peter was to be respectful to which ever technician looked after him.

A couple of days later Jean called by the shop and asked Peter to meet her for a coffee when he closed up. She wanted to discuss what had happened so far and her future plans. Peter nervously awaited the chat and wondered if he would be brave enough to raise any of his own concerns, knowing that as soon as Jean looked at him a certain way he would clam up. Later at a nearby coffee shop, Jean said that fortunately for him she had a favourable report back from Laura about the visit to the salon. She went on to explain that it would be her decision who was let in on Peter’s little secret as she would need help in the training. She would do her best not to affect his business in any way but outside of that all his time was to be spent developing his sissy and sub sides and learning his place. As a consequence of this, she asked him to write down his normal movements so she could see what free time he had.

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By *r 007Man
over a year ago

harrogate


"Fantastic xx"

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By *opsterMan
over a year ago

bicester

Well done, keep going. Very enjoyable!!

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By *teviem40Man
over a year ago

stoke

More please

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By *hicsterMan
over a year ago

ayrshire

Great reading keep it up pls

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By (user no longer on site)
over a year ago

A great story, so looking forward to more. Xx

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By (user no longer on site)
over a year ago

This is great

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By *d funMan
over a year ago

Telford

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By (user no longer on site)
over a year ago

Great story

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By (user no longer on site) OP   
over a year ago

Due to his secret life, Peter did not have many friends and apart from the odd social with close friends and the odd cinema trip, he spent most of his time by himself. This sounded perfect to Jean, even if she did think it was a waste of his time and energy. There was so much more productive things he could be doing than sitting home alone watching television and day dreaming of a sissy life. He should be out there living it instead. She ended the chat by telling him to be ready for another shop visit by someone else who would be helping, but Jean gave no further information. She also informed him that he would be visiting her at her home on Saturday for some more lessons. He mentioned that he had a lunch arranged with a friend, but Jean just looked at him and told him to cancel it. She wrote down her address and told him to be there promptly at 12 noon.

Promptly at 12 noon Peter rang the bell at Jean’s house, not wanting to incur her wrath for being late. He nervously looked around while he waited but saw no one. He was dressed in a smart trousers and shirt set, with the required lingerie on underneath.

A couple of minutes later the door opened and Jean was there, dressed in boots and a smart black dress. She beckoned him in and closed the door. Immediately she told him to strip to his lingerie and get down on all fours. A bit surprised at the order, he hesitated and that earned him a slap on the side of the face. He shuddered and then obeyed the order. She reached into a drawer and took out a collar and leash which was soon around his neck and she started to walk away, pulling on the leash. He had to chase to keep up.

After a few minutes they reached a sitting room where Jean took a seat and pointed at a spot on the floor near her feet for him to kneel. Jean looked at him slightly shaking and smiled. She loved the fact that he was nervous in her presence. She asked him how he was feeling and did he regret leaving that note in the book. He admitted that it had all being a whirlwind but deep down it was what he wanted and he would not have changed a thing. He was a bit perturbed when she let others into his secret like Laura and the shop assistant at the adult shop, but there was little he could do about it. He was both nervous and curious about what she had planned. She smiled and thanked him for his honesty and told him it was right that he should be nervous.

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By (user no longer on site)
over a year ago

Keep going.

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By (user no longer on site) OP   
over a year ago

Reaching behind her she took up a book and started to flick through it until she found what she was after. She showed him a picture of a very frilly french maid uniform in black and white, with frills on the edge of the sleeves and around the collar. It was complimented with an around the waist white frilly apron. Jean asked Peter what he thought about it but the look on his face and the stir in his cage told her all she needed to know. She grinned and informed Peter that one of these uniforms was being made in his size and once it was ready, he would be serving her at her home as a maid. Full training would be provided, but with punishment included if necessary for sloppy work. All going well in time she would lend him out to other chosen friends to clean their places as well, stating that a busy sissy is a happy sissy. Peter was not sure if he agreed but kept silent.

Jean then stood up and taking the leash told Peter to crawl behind as she gave him a tour of the house. In a room near the back the only thing in the room was a wooden chair and a chest of drawers beside it. Jean walked towards the chair, sat down and told Peter to go over her knee. She then asked if he was ever spanked when he was a child and he replied that his parents did not believe in corporal punishment. Also as he was considered a teacher’s pet in school (another reason for few friends) he was rarely sent to the head master’s office for discipline.

Jean smiled and informed him that she was a strong believer in corporal punishment and the power it had to keep a sissy on the right track. From now on she would be noting down any errors or hesitations that Peter made in training or in following orders and it would be rectified in this very room. He therefore knew that any time he was summoned to this room, it was going to be a painful time for him. Jean opened the chest of drawers beside the chair and let Peter have a look at the array of implements that were in there. They ranged from paddles to wooden hairbrushes all the way up to canes. Having never felt any of these before he was quite worried as to how they would feel.

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By *r 007Man
over a year ago

harrogate

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By *d funMan
over a year ago

Telford

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By *dsindyTV/TS
over a year ago

East Lancashire

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By *i015Man
over a year ago

Millbrook, Southampton

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By (user no longer on site) OP   
over a year ago

Jean picked up the hair brush and took down Peter’s panties. She started by rubbing the bristles side against his ass cheeks, which made him giggle a wee bit as it tickled. She stated that she was going to give him a taste of what was to come when he misbehaved (no point saying if as it was bound to happen at some stage). She told him to count each one. He took a short breath and then all of a sudden the wooden side of the brush landed on his right cheek with a wallop. It almost took his breath away and he struggled to say anything let alone utter the word “One”. Then it was the turn of his left cheek as Jean spanked it with the brush. Though he thought he knew what was coming, again it almost took his breath away. He just about managed to utter the word “two”. This carried on for the next ten minutes or so, with blows raining down on his cheeks in turn. If he forgot to count, the stroke was rejected and taken again. Soon his ass was very red, almost as red as his face. Thankfully Jean put down the brush and told him to go stand in the corner with his hands on his head. She told him that after every punishment he would display his red ass in this style while he reflected on his errors and how he could improve.

After half an hour standing in the corner, he was summoned back to kneel at Jean’s feet. She examined his ass which was still quite red and had a little giggle. Ever since she had read his note she had wanted to do this to him. Jean walked to a nearby table and took up a small box that was there and brought it back. She opened it and showed Peter that it contained three butt plugs of different sizes and some lube. She explained that it was time his ass got some training as it would need to accept what she had planned for the future. Peter whimpered a bit at this thought as nothing had ever been up his hole, not even his own finger. She told him to bend over the chair and hold his cheeks open. Luckily for him she applied a decent amount of lube to the plug and to his ass and gently eased it into place. After a bit of squirming and wriggling the plug was in place. Jean informed Peter that he was to leave it in all the time, only to be removed when he needed the toilet, but then immediately replaced. Within a few weeks she expected that he had moved up the sizes and was comfortably taking the largest one in his ass. Peter was not sure how he felt about this idea but as usual said nothing. He was then sent home.

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By *d funMan
over a year ago

Telford

i want this

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By *obbly2000Man
over a year ago

Doncaster

Me too please

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By *r 007Man
over a year ago

harrogate

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By (user no longer on site)
over a year ago

Good story

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By *vhazelMan
over a year ago

Ely

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By (user no longer on site) OP   
over a year ago

About a week later he got a phone call at the bookstore from another female he did not remember, someone called Amy. It turned out Amy was the young lady who served him and Jean in the adult store and of course was aware of his little secret, She told him that he needed to call by the store at six that evening, The store would be closed to everyone else but she was waiting behind for him. Tentatively he arrived on time and rang the bell. When Amy opened the door, she was dressed in a leather mini skirt, white blouse and black boots, a wee bit different to the first time he had seen her in the store. She ushered him in, closed the door behind him and ordered him to strip completely. Not wanting to suffer any further punishment, he did as was directed and soon the only thing he had on was the ever present chastity cage.

Amy led him over to a mirror with a chair beside it, on which was placed various clothes. Unsure of what was happening, he waited till Amy explained. She said nothing but handed him some white stockings and suspenders to put on, followed by matching bra and panties. She then held open a black dress for him to put on and she zipped it up at the back and all of a sudden he heard a click, which made him realise the dress was locked on. Looking in the mirror he soon realised it was not just a dress but it was the French maid uniform Jean had told him about. Amy finished off the look with the apron and some heels, which were also locked on. Amy smiled at the finished look and said that he looked the perfect picture of a male sissy maid. In time he would earn wig and makeup to complete the look, but only after some serious training.

Peter was about to say something at this stage, thinking that this was all going a bit too far and enough was enough, However Amy must have noticed something as she quickly approached with a ball gag, When inserted and locked on, Peter could hardly say a word. Amy commented that the best sissy maids were silent while they were working. She added a posture collar and wrist cuffs with a linking chain and declared Peter’s uniform was complete. She positioned him against a wall and took some pictures, which she immediately sent to both Jean and Laura. Adding a leash to the collar she took Peter for a walk around the shop to get him used to walking in the heels. The posture collar kept his head up so he could only look straight ahead.

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By *us man1957Man
over a year ago

Guildford

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By *ndrea54TV/TS
over a year ago

cambridge

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By *imale38Man
over a year ago

Barnsley

Wow. LOVE this story.

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By *dsindyTV/TS
over a year ago

East Lancashire

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By *r 007Man
over a year ago

harrogate

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By *vhazelMan
over a year ago

Ely

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By *arriedfun51Man
over a year ago

Northern Ireland

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By (user no longer on site) OP   
over a year ago

At the end of the walk they approached a large straight back chair, upon which Amy took a seat and she pointed at her feet for Peter to kneel. She looked at him and smiled and then announced she was going to remove the gag, When it was free he was immediately to lower his head and kiss her boots as a way of saying thank you for the outfit and the time and effort she had put into getting it ready. Any fight or hesitation on his part would result in a punishment worse than the spanking he had got from Jean. Peter went slightly red in the face when he realised that Amy knew about the spanking and therefore assumed Laura did. Little did he know that they had a regular chat group where they were keeping each other up to date on the progress of their little sissy. As soon as the gag was taken out, Peter wet his lips and then bent down to kiss Amy’s boots and lick them all over. Any thought of fight had left him for now as boot worship was one of his favourite things and it gave him some peace, Peter was left worshipping the boots for about fifteen minutes. While he enjoyed it mostly it did cause some discomfort in his cage as his cock was trying to get hard unsuccessfully.

Even though she was lost in thought as the boot worship went on, Amy called it to a halt and led Peter back to the changing area. She undid all the locks and stripped him back to the cage and told him to get dressed in the clothes he arrived in. She packed the uniform and accessories away carefully and gave him the bags to take with him. She warned him to take very good care of them as there would be hell to pay if any dirt or damage happened to the uniform. Her last words as she let him out of the shop was that Jean would be in touch to arrange his first cleaning lessons and she looked forward to having her own maid on the days the three ladies had arranged.

The next couple of weeks went by with very little interaction with any of the ladies. Peter was still going to work dressed, caged and plugged as never sure when he may have a visit to check up on him. After this time he had trained his ass up to the medium plug. After going through all he had he was now a bit worried that the ladies had forgotten about him and it had all being a huge joke on their part. He was so used to hearing from them and following their rules that the lack of contact felt out of character. It just shows you how quickly a life can change.

A couple of days later Jean popped in and told him they were going for lunch. She asked how the visit with Amy had gone, even though she had got a full report from Amy of course. She knew it was humiliating for Peter to reveal all in his own words, as if it was making him live through the experience all over again. When he had finished telling the tale, she smiled and congratulated him on not leaving out any detail. He realised yet again he needed to always be honest with her as obviously both Laura and Amy were keeping her well informed. After lunch Jean informed him that she would collect him when the shop closed that evening as she had some tasks for him.

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By (user no longer on site)
over a year ago

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By *imale38Man
over a year ago

Barnsley

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By *eighbiMan
over a year ago

Leigh

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By *r 007Man
over a year ago

harrogate

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By *d funMan
over a year ago

Telford

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By (user no longer on site) OP   
over a year ago

Later that evening when they arrived back at her place, as soon as he walked in the door he was ordered to strip to his underwear. Jean declared that apart from the small hallway he was forbidden to wear male clothes in her house. She would leave a hanger there for him to hang them up and on another hanger would be whatever she wanted him to wear. For this evening all that was on the other hanger was a white frilly maid’s apron. Thinking back to the uniform he wondered why just an apron but just put it on. Jean added the necessary accessories of collar, gag, wrist cuffs with chains and leash. Beckoning him to get down on all fours, she led him to the kitchen where he could see a pile of dirty dishes. Jean explained that she had been saving them up for the last couple of days in preparation for his first lesson. She undid the wrist cuffs but added an ankle cuff with a long chain attached. This gave Peter the movement he needed to wash the dishes and put them away, but he could not move very far from the sink. Jean set a timer and told him she would be back in an hour to inspect the progress.

Not being able to do anything else, Peter set about cleaning the dishes. There was a lot of work to do to get all the built in food and dirt off them and make them presentable. He carefully stacked them up to dry, not wanting to know what would happen if he broke any of Jean’s dishes. When the hour was up, Jean walked back in and did not look happy at all. She appreciated that this was his first lesson but she felt that he was very slow at it and not made the progress she expected. She took him by the leash and bent him over the kitchen counter. Taking up a nearby cane (implements were readily available around her house as Peter would find out) she pulled down his knickers and gave him fifteen quick strokes with the cane. When she was finished and Peter was in tears, she explained that she expected her maids to work quickly as there was a lot to do around the house. Peter would stay chained to the sink until all the dishes and glasses were properly cleaned and put away, no matter how long it took. It was about nine that evening before the job was finally finished to her satisfaction and Peter was released from the chain. Jean sent him home to sleep which was not going to be an issue.

Over the next two weeks Peter’s new life settled down to a different schedule. Each day he worked in the shop dressed as required. Every couple of evenings he went around to Jean’s, stripped at the door and put on his sissy apron. He crawled into the kitchen and attached himself to the sink if Jean was not there to do it. He then spent the next couple of hours cleaning the dishes and putting them away. His cleaning time was getting faster and faster but he still suffered some more cane strokes for still being slow.

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By *r 007Man
over a year ago

harrogate

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By *d funMan
over a year ago

Telford

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By (user no longer on site) OP   
over a year ago

Any interest in any more?

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By *orgotten22Woman
over a year ago

out in the sticks in the north east england

Yes please x

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By (user no longer on site) OP   
over a year ago


"Yes please x"

Which female would you be like

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By *dsindyTV/TS
over a year ago

East Lancashire

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By (user no longer on site)
over a year ago

Keep going

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By (user no longer on site) OP   
over a year ago

One evening when he got there, he got a shock as all three women were present which was the first time that had happened. He was told to carry on with the dishes while they chilled out and drank and had fun. He felt he was part of the topic of conversation but could not hear what they were saying. After about an hour of cleaning, Amy came in and undid the chain. She ordered him down on all fours and told him to follow her into the living room. He was positioned near the table and a new gag was put in his mouth. This gag had various extensions that could be attached to make the gag very versatile. The one he got to try out this time was an ashtray, As the ladies carried on chatting and drinking, every now and then Amy and Laura would drop their ash in the gag in his mouth. As the tube was not hollow it did not go into his actual mouth, but he got the smell and the smoke in his eyes. Apart from using him in this way the ladies completely ignored him as if he was not even there. He guessed this was just another use for a sissy and he would have to get used to it. After about an hour on his knees he was taken back to finish the dishes and then eventually dismissed for the evening.

About a week later Peter got a visit from Amy at the shop and she informed him that his training was going up a level that evening and she would be waiting for him after work. She reminded him that at the very beginning of this adventure he had given Jean a list of his limits and things he wanted to try but was never brave enough. One of these would be tried out tonight. She left, reminding him to be ready at six when the shop closed. He spent the rest of the day trying to remember what was on the list and what may be in store for him tonight but could not come up with anything.

Promptly at six Amy was waiting outside and led Peter to her apartment, which was the first time he had been there. It was a small well decorated apartment and looked well looked after. As per normal he was told to strip to his lingerie and cage on the door and get on all fours. This is how he toured the apartment following Amy without the use of a collar and leash. He had learnt well how to heel and follow like a pet. The final room they entered was the bathroom and this is where Peter shivered briefly as he remembered a very hard fantasy he had outlined to Jean. Amy looked around and picked up a new gag and inserted it into Peter’s mouth. It consisted of a ring gag that kept his mouth open but also had a funnel attachment of which the tapered end went down his throat. Once it was buckled in place, Amy took off her dress and positioned herself over the funnel. She smiled and said she had been saving this all day and very soon a large quantity of her pee entered the funnel and went down his throat. He tried not to gag at the taste or smell of it. He was warned not to spill a drop or he would be licking it up from the floor. Amy went on to explain that Jean felt it would be more humiliating if she or Laura used him this way first before she did. Jean wanted to be sure he was properly trained in drinking pee before he was honoured with her golden nectar.

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By *r 007Man
over a year ago

harrogate

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By *d funMan
over a year ago

Telford

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By *arriedfun51Man
over a year ago

Northern Ireland

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By *i015Man
over a year ago

Millbrook, Southampton

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By *i015Man
over a year ago

Millbrook, Southampton

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By (user no longer on site)
over a year ago

Really good story

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By (user no longer on site)
over a year ago

What a great story. Looking forward to the next instalment.

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By (user no longer on site) OP   
over a year ago

Peter was not sure how he felt about this new development but realised he only had himself to blame. He was too honest in explaining his desires and needs; no matter how humiliating and the ladies were only giving him what he asked for. He definitely had a lot to think about when he left Amy’s that evening and tried to sleep. The fact that he had been locked in chastity all this time did not help matters either and there had been no mention of if or when he may get release.

A few days later Jean messaged and told him that as a treat the three ladies were taking him to a bdsm club at the weekend. He was warned to be on best behaviour as this would be his first public outing as their sissy and did not want to be let down or embarrassed. As preparation for it he was told to pay a visit to the beauty salon to make sure all hair was gone and that he was looking his best for his mistresses. As usual there were some giggles when he arrived as everyone had got used to his visits and often the trainees were sent in to watch his treatment as part of their learning. This of course was all in order to add to his embarrassment. This time, apart from the normal waxing and dehairing, his toe and finger nails were treated and painted a deep pink.

He had been told to report to Jean’s place at five pm on Saturday so he could be prepared for the trip. When he arrived he stripped as normal and got down on all fours and was led into the spare bedroom. On the bed was a dress bag with what he assumed was his outfit for the evening but as of yet he could not see what it was. He was led into the en suite and told to have a quick shower and then wait there. When he was ready Amy walked in, placed his hands behind his back and cuffed them. She then raised them above his head and attached them to a hook so he was bent at the waist. The ever present butt plug was removed and Amy proceeded to give Peter yet another new experience as he was given a very thorough enema. The process was repeated three times until Amy was happy he was totally clean inside and out. After that was finished he was led back out to the bedroom.

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By *imale38Man
over a year ago

Barnsley

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By *r 007Man
over a year ago

harrogate

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By *ndrea54TV/TS
over a year ago

cambridge

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By *d funMan
over a year ago

Telford

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By *rodigalMan
over a year ago

sunderland

Wow

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By (user no longer on site)
over a year ago

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By *es for funMan
over a year ago

port talbot

horney as fuck

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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

After sitting down in a chair, he was handed some white stockings to put on, along with matching suspenders, panties and bra. The whiteness of the underwear showed off the pinkness of his chastity device even more. He was then told to stand and hold his hands straight up over his head. Amy then walked behind him and lowered the dress over his head. It was zipped up and of course locked so he could not remove it. Something was adjusted around the waist and finally he was handed a pair of 4 inch pink heels to put on. Apart from his nails the only makeup he was allowed was pink lipstick. When he was positioned in front of the mirror he finally got a look at the dress. It was a very frilly pink dress, with white frills around the collar and the end of the sleeves. There was a big white bow that had been properly tied around his waist. The end of the dress came down to just before his knees so the edge of his suspenders were on show. He looked like a total sissy.

Amy walked over the a chest of drawers and took out some accessories. The first was a white posture collar like the one he had tried on in her shop with the maid uniform. His arms were positioned behind his back and strapped into a single white arm sleeve which kept them tight to his back. Amy bent down and added straps around the heels which locked on and had a connecting chain between them, making sure he would have to take very small steps. The final addition for now was a very big white ball gag.

Now that Peter was ready for his first outing as a sissy Amy went off to get changed and to gather the other two ladies. When they all came back Peter could not believe how they were dressed and his cage let him know how he felt. Amy was dressed in a black latex cat suit which covered her whole body and included a hood which only left her face uncovered. On her feet were a pair of six inch knee high leather boots and to go along with the outfit she carried a whip. Laura was dressed in a latex dress that just about came down to the end of her ass. Under it she was in rubber stockings and suspenders and six inch heel stilettos. Jean was dressed almost like the first time Peter saw her, in a black skirt and white blouse, though this time they were both made of latex. On her feet were thigh high leather boots. They all looked stunning and Peter was not sure what he was in for. Jean attached a leash to the posture collar and Peter followed the ladies out to the waiting car as they headed to the club.

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By (user no longer on site)
over a year ago

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By *dsindyTV/TS
over a year ago

East Lancashire

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By *r 007Man
over a year ago

harrogate

wow love the sound of all the sexy outfits

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By *d funMan
over a year ago

Telford

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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

Peter had never been in a club like this before, He of course had read about them and dreamt of them but never thought he would attend one, especially not at the end of a leash. When they arrived he expected to be ordered down on all fours as was normal but was informed that he could walk this night as the ladies wanted to show him off. Any bad behaviour would be dealt with sternly and immediately no matter who else was there. The three ladies were greeted as old friends by the staff who looked the sissy up and down and just smiled. Then they went into the main part of the lounge and Peter’s mind almost went. Where ever he looked he saw people in latex and pvc or sissy outfits like his. There was a mixture of all ages and sexes and both men and women in some forms of bondage as other members of both sexes held their leashes. There was some equipment around the edges of the dance floor which looked like was there to punish disobedient subs or just let people have fun. He also saw some cages at the back where subs could be housed while their owners discussed private business or had fun without them.

The party of four were led to a booth near the centre of the club, with the three ladies being stopped every now and then to be greeted by old friends. Every time they stopped Peter had to do a twirl so their new sissy could be shown off. Many complimentary comments were made about the progress they had made with him and people wishing to borrow him at some stage. Finally the three ladies were seated looking out on the main floor. Peter was positioned with his back to the main floor, on all fours under the table with the leash attached to a hook there. The ladies ordered drinks and settled in for a chat. When the drinks were delivered he assumed it was by a lovely young lady dressed in a short French maids dress and chains between the wrists and ankles. He had seen some of them serving other tables on the walk to the booth. Peter was not sure if anything had been ordered for him and of course he was gagged so could not ask. But a dog bowl of water was placed on the floor near him. Amy undid the gag and told him to lap it up but not to spill any on his lovely dress.

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By *ucky78Woman
over a year ago

liverpool

Interesting x

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By *i015Man
over a year ago

Millbrook, Southampton

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By *us man1957Man
over a year ago

Guildford

Been reading this wonderful story very good insight to this type of scene thank you

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By *d funMan
over a year ago

Telford

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By (user no longer on site)
over a year ago

mmmmmmmmmm

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By (user no longer on site)
over a year ago

Loving this a little too much

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By (user no longer on site) OP   
over a year ago

For about an hour or so the ladies carried on chatting and watching what was going on in the club. From his position under the table Peter could see nothing and could hear very little as well so had no idea what was going on. All of a sudden he felt the leash being unattached from the hook and he was summoned out from under the table. It turned out that Laura had a hold of the leash and beckoned for him to follow her. Due to the position of the posture collar Peter could only keep his eyes forward and high so had to trust Laura was leading him safely. They arrived at a door at the back of the club and when pushed open, Peter could see they were in a private dungeon room. There was one couple in the room, a female domme and a male slave who was strapped to a cross as he was being paddled. The paddle was hitting various parts of his body from his back to the top of his thighs and everywhere in between. Obviously it had been going on for some while as the back of his body and his ass were quite red and welted in some areas.

Laura stopped to watch a while and whispered to Peter that she was getting some tips on how to ensure a good all round paddling for when she got to try it with him. This made him shiver slightly. They then carried on to the very back of the dungeon where there was a cubicle. Peter was not sure what happened here but had a feeling he would soon find out. When they stopped Laura undid the arm sleeve and the ankle chains. She told Peter to carefully remove the dress and hang it up on the rack nearby. When he was just in his ever present lingerie he was led into the cubicle and the use immediately became clear. Obviously the ladies had decided to take his toilet training to a whole new level. He was positioned on the floor with his arms chained to the wall either side of his head. Chains also went around his legs so he could not get off his knees. The final attachment was the large ring gag and the toilet funnel that Amy and Laura had broken him in with. It seems he was going to be the urinal for anyone who wanted to use him that night. Laura left him there and told him they would be back when they wanted to go home.

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By *d funMan
over a year ago

Telford

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By *r 007Man
over a year ago

harrogate

lucky boy

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By (user no longer on site) OP   
over a year ago

After about three hours Amy came back to collect the poor bedraggled sissy who had been well used. He was not allowed to put on the dress but was told to crawl behind Amy on all fours back to the front door. She kindly carried his dress for him. The three ladies laughed at the sissy and then headed home. In the car it was explained that tonight was a reminder that the sissy was theirs to do with what they wished and he could be lent out to anyone or any group whenever they felt like it. Of course Jean, Amy and Laura were his main owners and would ensure all his limits were agreed to, but they did intend to keep enforcing in him what his position was. When they arrived back at Jean’s Peter was led to a dog cage in the back room and was told that was his bed for the night. He crawled in and the leash was attached to the front of the cage and he heard the door being locked shut. So he was going nowhere and did not expect much sleep in the cramped cage but also had a lot of thoughts going through his mind.

After a few hours of restless sleep, the cage was unlocked and he was told to crawl to the shower, undress and clean himself up. He still smelt of all the piss from the night before. After that he crawled naked apart from the chastity cage to the kitchen and was fed some breakfast and water from dog bowls on the floor. The girls decided to go a bit easier on him today and give him some time to rest. This of course would not be as straightforward as he may hope. Out of the ever growing kit of accessories the ladies had access to, special foot and arm cuffs were placed on him, which meant he could only move around on all fours. A hood in the shape of a dog mask was put on his face and he was led out to the secluded back garden to spend some time as their pet.

He had to play fetch whenever they threw something for him to catch or else he was allowed to spend time just resting like a dog in the cool weather. Any time he needed a drink he had to beg like a puppy and he would be led over to a dog bowl to drink. When it came time for him to go to the toilet Amy led him to a tree at the back of the garden and told him to go there. It was difficult for him to go in this situation especially with Amy looking on but knew he had little option. At the moment he was nothing but a dog and had to act like one until the ladies would let him return to human form.

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By *us man1957Man
over a year ago

Guildford

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By *untimes6969Man
over a year ago

Newcastle upon Tyne

More!

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By *i015Man
over a year ago

Millbrook, Southampton

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By *d funMan
over a year ago

Telford

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By *r 007Man
over a year ago

harrogate

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By (user no longer on site) OP   
over a year ago

A couple of weeks went by with little interaction from any of the ladies. Peter had almost forgotten what his life was like before that fateful meeting with Jean in his shop. He was so used to wearing lingerie, the plug and cage it felt like he had been doing it all his life. At the end of the second week he had a visit from Jean and was informed he was coming to hers after work for a meeting with all the ladies and deciding how to proceed. He was collected at six and as usual stripped as soon as he got there and crawled on all fours to the living room where everyone was gathered.

The ladies all looked at him and told him to reply honestly to their questions. He was asked how he felt about everything that happened so far, was there anything he would change and did he want to continue. He had to think for a while before answering but honestly replied it was still a bit of a shock, but none of the ladies had gone outside agreed limits and they definitely had made his life a bit more interesting. As to continuing could he have some time to think about it.

They all thanked him for his honesty and granted him time to think, but as usual under their conditions. He was taken to the dungeon and the big cage at the back. A hood that took away his sense of sight and hearing was placed on his head. A ball gag was added to keep him silent and he was placed in the cage. He was told that he would have twelve hours of isolation in the cage to decide how he wanted to proceed, if he did. If he agreed to proceed things would be seriously ramped up.

When the twelve hours were up, Peter was let out of the cage by Laura and told to go have a shower and meet them in the kitchen. For the serious discussion that was about to happen he was allowed to sit in their presence and enjoy breakfast and some general chat. He found that he did enjoy their company and found it very easy to talk to them, even about things he had kept hidden for many years. When the meal was finished and the dishes were stacked up to be cleaned later, Jean addressed the group.

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By *es for funMan
over a year ago

port talbot

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By *d funMan
over a year ago

Telford

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By *r 007Man
over a year ago

harrogate

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By *us man1957Man
over a year ago

Guildford

More please

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By *ndrea54TV/TS
over a year ago

cambridge

Loving this

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By (user no longer on site) OP   
over a year ago

She said that she and the other two ladies had really enjoyed the adventures with Peter, though a lot of it had come as a surprise and they even shocked themselves as to how far they went and how much they enjoyed it. They appreciate that it was a very brave thing for Peter to put that note in the book for Jean especially as he did not know how she would react. She could have been disgusted and walked out of the shop never to return. Maybe it was fate or he was just fortunate that she had a similar interest and had been looking for someone to explore it with. In the same way it was fate or fortunate that they met Amy and Laura on the way and that they were also open to exploring. The three of them had fed off each other’s ideas and done some more research on the scene to give Peter what they believed he wanted, while understanding that their pleasure was what really counted. They hoped he would agree that they may have pushed him but have not gone past any limits he had disclosed. The question was where they went from here. They could continue but take it to the next level or they go their separate ways. It had to be an unanimous decision as they did not want any one taking part who was not fully into the journey.

Amy and Laura agreed with Jean’s summary and said that while unexpected they had enjoyed and wished to continue. They did have other things they wanted to try as well. So the final decision was down to Peter – did he continue as their sissy or did they part ways. Before he made his decision, the ladies laid out what the future entailed as their sissy. He would carry on in the shop and have some time to himself, but most of his spare time would be spent serving as maid to the three ladies. They would agree a rota for him to clean their houses and do their dishes. They would continue to train his ass and in time they would each take it with a strap on. Eventually they would also like to train him to please cocks like all good sissies should.

The end

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By *eviantDelightsMan
over a year ago

London/Cambridgeshire

Oh no, the cliff hanger ending

What would Peter have chosen... guess we will have to leave it to our imaginations, but I suspect we can all guess.

He was definitely brave with the note. Not sure if I would have been able to do the same in his place but I sincerely hope I would if the opportunity presented itself.

Thanks for such a great and well written story!

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By *us man1957Man
over a year ago

Guildford


"Oh no, the cliff hanger ending

What would Peter have chosen... guess we will have to leave it to our imaginations, but I suspect we can all guess.

0 wholeheartedly agree with this statement He was definitely brave with the note. Not sure if I would have been able to do the same in his place but I sincerely hope I would if the opportunity presented itself.

Thanks for such a great and well written story!"

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By *r 007Man
over a year ago

harrogate

next one please

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By (user no longer on site)
over a year ago

Yummy

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By *vanabeusedTV/TS
over a year ago

somewhere

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By (user no longer on site)
over a year ago

Wow. What a great story. Can’t wait for the movie.

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By *hil911Man
over a year ago

Solihull

Just found this.

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By *tephens11Man
over a year ago

Leeds

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By *ub Male ExhibitionistMan
over a year ago

bromsgrove

Great story!

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By *uetv2TV/TS
over a year ago

Poole

Wonderful story xc

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By *stwo80Couple
over a year ago

yorkshire

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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


" "

Glad you liked

Nice cage

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