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caught
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By (user no longer on site) OP
over a year ago
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He had a stressful day and just wanted to relax when he finally made it home. However when he arrived back he realised the place was a mess and needed tidying up.
He then hit on an idea to make it a bit more fun. He stripped off all his clothes and went to his sissy wardrobe. He took out the very skimpy maid uniform, tights and a pair of pink panties.
Soon he had changed and then went to his toy chest and took out his thick collar that restricted the movement of his head. Finally he put on heels and locked a chain between them.
Slowly moving to the kitchen he ran the hot water and washed the dishes, a task he normally hated. But doing it in his sissy maid uniform made it more enjoyable. He could imagine he was cleaning the house for a visitor, knowing they would inspect the place and dish out punishment. If only he thought.
Once the kitchen was done he moved on to the bedroom and living room. He tidied them up and gave both rooms a hoover. This had taken him a couple of hours and he was tired . He relaxed in front to the computer, reading some sissy erotica.
After carefully hanging up the uniform he went to bed, wearing his pink nightie and dreamt of service. Little did he know his dreams may soon become his nightmare.
When he got back the following day and opened his door, there was a small brown envelope on the mat, with just a single S on it, no address or stamp. He picked it up and stared at it, not daring to open it.
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By (user no longer on site) OP
over a year ago
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He walked into the living room and sat down, just staring at the envelope. He had read stories about things like this but reality and fantasy are so different.
He thought he was so careful. He lived high enough up that was difficult to see directly into his place and most rooms had curtains. Most of his serious sissy adventures had been done on holiday, places no one knew him or would care what he wore in private.
Finally he opened the envelope. Inside was just one photo, nothing else and nothing written on it. He turned it over and dropped it on the table. It was a picture of him last night, taken through the kitchen window. His face, collar and maid's uniform were clearly seen. If this got out he would be instantly recognisable. But he thought "there is a blind in the kitchen, how did they get the picture". Then he remembered that he had lifted the blind to let light in as he washed the dishes.
But who took the picture? Which of his neighbours knew his secret and what did they want? Only time would tell. |
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By (user no longer on site)
over a year ago
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Great start. Look forward to the next part. |
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By (user no longer on site) OP
over a year ago
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Over the next couple of days he was terrified. Not knowing who knew or was it more than one person. He lived in a small close and his neighbours included a young couple, a single woman and a couple of single men, one young, one in their 70s. He did not really know any of them as he kept to himself, mainly due to his secret life. Looks like this was about to be exposed.
A couple of days later he came back to a small package on his doorstep, with the S on the cover again. He looked around but saw no one. He took the parcel inside, sat down and opened it.
Firstly there was another picture and then there was a small bag and a note. He read the note first :
"I have always wanted my own sissy maid and little did I know there was one living right beside me all this time. If you don't want everyone knowing, meet me in the local pub tomorrow night, 7pm. Under your male clothes wear what's in the bag and your pink knickers."
He looked at the note for a while and then opened the bag. Inside was something he had seen online but never in real life, a male chastity device. There was a lock but of course the key was missing. |
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By (user no longer on site)
over a year ago
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Go on please do continue |
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Please more. Well developing story |
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By (user no longer on site) OP
over a year ago
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So six o'clock the next day it was decision time. Was he going to let his secret be told or was he going to the pub as directed. Maybe if he went he could reason with whoever it was before this went too far.
He stripped off his trousers and panties (always female panties, just not always sissy) and took up the chastity device. Having gone on line to see how it was put on, it was soon in place and just the lock to close. With a huge sigh he clicked it shut and sealed his fate. He then put on the pink panties and replaced his trousers. Hoping that the bulge of the chastity device did not show.
Seeing it was now 18.45 and knowong he could not afford to be late, he grabbed his coat and set off on the short walk to the pub. Fortunately he did not bump into anyone he knew.
When he entered the pub was quite busy. He had a look around as was not sure where he was supposed to be going. As he did he noticed the couple who lived beside him at one table,deep in conversation. At another table was John the 70 yr old who lived opposite him. As he was standing there watching, he noticed a young lady looking straight at him. He did not recognize her at all. She was dressed in a white blouse, black skirt and ankle boots.
Nice outfit he thought but what drew his attention was the key on a chain around her neck that she was twirling in her hands. He stared at this key thinking "it can't be her, I don't know her, how did she find out".
Just then she beckoned him over. |
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and so sissy begins to know her place   |
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By (user no longer on site) OP
over a year ago
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Very nervously he walked over and stood in front of her. She pointed at the chair and indicated for him to sit. When he did she spoke "I wondered if you would show or not and now I know. Unless you want the whole pub to know that you are a sissy, I suggest that you get us some drinks and then listen quietly to what I have to say. Nod if you understand and my name is Anna, but you will call me Miss Anna". When he nodded she said that she was drinking white wine. He headed to the bar and quickly returned with her wine and a . This was not the night to try alcohol.
When he resumed his seat, she smiled and said "you don't know me and upto a few days ago I did not know you, but we are going to get to know each other very well. I have a couple of occupations, one of which may seem beneath me but acts as a good cover. I work as a cleaner for the flats opposite you, mainly the communal areas. Over time I have got to know the residents and some have become clients of my main occupation. You may say that I help people spice up their sex lives, or give them one if they don't have one". He looked shocked at this revelation but was taken back by her confidence.
"Imagine my surprise the other day looking out the window on a break from cleaning, only to see an old sissy maid doing his dishes in an uniform, expecting that no one would notice. What a lucky day that turned out to be for me. It only took me a short while to find out who you were and which flat was yours. And that leads us to here".
As she finished she placed her foot under the table and pressed it into his crotch. She grinned and said "I see you got and are wearing my present. That's a good start sissy and this will go all the easier for you if you just continue to obey" |
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Oh yes this is great. More more  |
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By (user no longer on site) OP
over a year ago
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Miss Anna smiled and then told sissy to tell her all about himself. He explained that he lived alone, never married, not many friends apart from the odd work colleague. He kept to himself and explored his kinks in private and went on holiday. All was well till now.
Miss Anna smiled and said "that's all good to know. As am sure you have figured out by now your life has changed and is now mine to control". "As a way of proving that I have a task for you. I want you to go to the disabled toilet, pull down your trousers and kneel down. When there is a knock on the door open it and give the man a bj. Swallow everything and come back to me. Here is a hood for you to wear" "Get up and do it now or I send your pictures to the net with your name"
He was absolutely shocked but had no choice. He took the hood and headed to the toilet. Shortly after getting in position there was a knock on the door. He opened and someone came in. They took his head in their hands and shoved their cock through the hole into his mouth. Using their hands they begin to face fuck sissy. |
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By *eajayTV/TS
over a year ago
Tamar Valley |
I so like Miss Anna x |
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By (user no longer on site) OP
over a year ago
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The face fucking continued for ten minutes with nothing being said. Suddenly the man shook and sissy's mouth was soon full of cum. The man told sissy that Miss Anna said to swallow all, tidy up and go back to her. He then left.
Sissy spent a few minutes to tidy up and make sure no cum was showing and sheepishly went back to the table and sat down.
Miss Anna smiled as he sat down and congratulated sissy on doing a good job. She said that it may amuse sissy to know that he knew who just used his mouth, even if the other person did not know it was sissy. Looking around he realised that John and the young couple were still here so it had to be one of them but he did not know which.
Miss Anna pointed to the couple and explained that they had become clients of hers. They were called Jane and Jim and she was helping in Jane's training. Jane had wanted to have more control over Jim. She pointed out the necklace around Jane's neck and how similar it was to hers. So sissy was not the only one in chastity in the bar that night. |
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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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Miss Anna outlined what was going to happen next.
Sissy will get her a copy of keys to his flat
Sissy will get rid of any male underwear, including vests and pyjamas
Sissy will buy new panties, Camis and nighties
Sissy will never stand to use the toilet again, not that the device will let him
If sissy does not already own some sissy is to purchase some butt plugs and start wearing them
Miss Anna will visit sissy at 7pm tomorrow to inspect his flat, his wardrobe and his toy collection
She looked at sissy and says "just nod if you understand all these and accept". Sissy just nodded, not having much choice.
Just then it looked like a light bulb went off over sissy's head. If Jim was in chastity it must have been his old neighbor John who face fucked him in the toilets. Miss Anna realised the penny had dropped and just laughed. "It won't be the last time John uses you sissy, just get used to it. Now go home and do your tasks and I will see you at 7 tomorrow". |
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By *abrina59TV/TS
over a year ago
moved to cuckold land |
Loving miss Anna already |
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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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i love miss ann and would love this too happen to me i would love a superior couple to own me mmmm x |
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Id love to be enslaved to someone. |
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By (user no longer on site) OP
over a year ago
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On his way back from the pub sissy was trying to understand all that had happened and was going to happen. He never felt what he was doing was wrong but know other people could not accept it so could not afford to be outed- he may lose his job.
As soon as he arrived home he got a black bag and put all male vests and pyjamas in it and two pairs of emergency male undies he kept. For years he had worn female but kep male for doctor visits etc. He thought he had enough camis. panties and nighties - he just moved them from their hiding place to his main drawers and hoped they would do for Miss Anna.
He then prepared a table in his living room upon which he laid out all his toys. They were mainly bondage related, like cuffs, hoods, gags, leashes and a couple of pain implements. He had thrown out his butt plugs as rarely used them so knew that he would have to shopping tomorrow after work.
He finally had a look at his wardrobe - mostly normal female clothes, apart from a couple of maid uniforms, a cheerleader outfit, a school girl uniform and a couple of pieces of PVC wear. As he was tired he headed off the bed though he did not sleep well at all.
On his way back from work he popped into the sex shop that he knew about but had never been brave enough to go in. Looking a bit lost a young female shop assistant approached and asked if he was ok. He quietly explained that he needed some new butt plugs of different sizes. She smiled and led him over to where they were. There was a pack of five there, going up in size which she recommended, along with some lube. She also suggested a belt that went around the waist that could be locked to keep the plugs in. He followed her advice and the shopping was rung up at the till. As he left she told him her name was Marie and if he needed anything else to ask for her next time.
He quickly left and got home and added the new toys to the collection on the table and then sat down to await Miss Anna. |
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This is the sort of thing I dream of. |
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By (user no longer on site)
over a year ago
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Wow, love this |
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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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Promptly at seven there was a ring at his door. He opened the communal door and waited for Miss Anna to climb the stairs. He stood aside to let her enter and then closed the door. She had obviously come straight from work as was dressed in overalls and a tabard. She was carrying a bag with her. She looked at sissy, dressed in trousers and shirt, and reached out and slapped him twice on the face. She then asked where the bedroom was so she could get changed.
Slightly chastened he pointed the way and went to the living room to wait. A few minutes later he heard her approach and looked up. She was now dressed in a leather dress and knee high boots. She walked over to him, slapped him twice more and pointed to the floor. He knelt and she took a seat.
"Well sissy you may wonder what the slaps were for. I know you are new to this but certain things should be obvious to you:
1 you await a superior on your knees
2 when home you are dressed as the sissy you are
3 you never look a superior in the face unless she allows it
4 you never sit in the presence of a superior unless she allows it
So four errors, four slaps"
"Now say thank you Miss Anna for your corrections and strip to the panties you better be wearing".
Quickly sissy took off his shirt, trousers, shoes and socks, leaving him in pink panties and quietly said "Thank you Miss Anna for your corrections". |
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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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This is so good, i would love to be treated like sissy.. |
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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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This story can’t update quick enough for me I’m hooked |
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By (user no longer on site) OP
over a year ago
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Miss Anna then turned her attention to the toys laid out on the table. She knew what most of them were and loved the fact that most of them were lockable. She particularly liked the ankle hobbles, esp as sissy explained he had been wearing them that fateful day. She asked sissy to explain what the gag with various attachments was.
He explained that he had seen a video online of a slave girl having to clean the toilet with a brush attached to a gag on her mouth. It was called a humiliator gag and he ordered it from the States. His main attachment use was the ashtray gag. Miss Anna exclaimed with joy and said that would come in very useful at parties. "Parties? sissy was thinking but too afraid to say it out loud.
Miss Anna then looked at the butt plug set and asked about the belt. He explained that Marie, the assistant in the sex shop had suggested it. That brought a smile to Miss Anna and gave her an idea.
"Sissy I want you to return to the sex shop at the weekend and seek out Marie. You are to tell her that Your new owner was very impressed with her suggestion and that you need to buy another set of plugs and belt. I then want you to visit your neighbour Jane. You are to apologize to her for not offering your services as a sissy maid to her. Then give her the package to help in her training of Jim."
sissy looked shocked and said that he thought this was about keeping his secret safe, not exposing him. Miss Anna explained that sissy had a choice, be exposed to a few people of her choosing or be exposed to everyone. Sissy bowed down and kept quiet. |
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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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Mmmm my kind of lady |
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By (user no longer on site) OP
over a year ago
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Miss Anna then told him to stand, lower his panties and bend over the couch. She took up the lube, opened it and added some to her fingers. Suddenly he felt her hand on his backside as she started to massage the lube in. She then took up the smallest plug, lubed it and without warning shoved it straight in. He gave out a gasp as the plug worked its way past his muscles and filled his hole. "A sissy's hole should always be full and prepared to be fucked" Miss Anna says. "That stays in unless you need the toilet but it goes right back in". "We will leave the belt for now".
Sissy adjusted his panties and knelt back down. Miss Anna picked up one of the collars and locked it around his neck. Adding the leash she told him to get on all fours and lead her to his wardrobe. When they arrived, he stayed kneeling while she examined the clothes in detail. She explained that he would need more camis and panties, especially in more sissy colours. She also told him to change his bed linen to the pink set he had in his drawers. She liked his sissy clothes, especially the two uniforms. He was informed that a more formal one would be needed, her friends had high expectations and standards.
He was then told to dress as he was the day Miss Anna discovered him, including the heels. Leading him back to the living room Miss Anna took pleasure in locking on the hero hobble. He was sent to stand by the wall facing her so she could get some new pictures. Then back on all fours and crawl over and kiss her boots. "This may be overwhelming for you sissy but you are doing good. I will be leaving shortly but will be back in two days. By then I expect this place cleaned properly, dressed as you are now". |
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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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It took him some time to get used to being plugged again. He was afraid someone at work would notice with the way he was walking. When he got home and had quick bite, he got changed and set about cleaning the flat. It took him about three hours to do, especially with the chain hobble on.
Friday evening at seven he was dressed as maid kneeling just inside his door. He was not sure when Miss Anna would arrive but he did not want to be caught out again. Just then his buzzer went so he opened the communal door and left his door slightly ajar. When Miss Anna saw him on his knees she smiled and patted his head. He was told to stay there while she inspected the place. When she was sitting in the living room he was told to crawl over and get across her knees. She lifted up the bottom part of his uniform and lowered his panties.
"You did a better job at the cleaning than I expected but you missed some bits sissy". She then took a wooden hairbrush out of her bag and started to spank his cheeks. She did not stop until she had administered 20 hard whacks to each side and left them red. He was almost in tears. She then told him to go to the corner and stand there with his ass on display.
"Shortly you will be changing and taking me for a drink in the local pub to thank me for all I am doing for you. It won't be a late night as you have an appointment in the sex shop with Marie and with Jane after. Both of them are to be respected and obeyed as if they were me, is that understood sissy". "Yes Miss Anna" came the reply.
He was then told to put on matching bra, panties, stockings and suspenders. Over which went trousers and rugby shirt but no socks. Miss Anna was dressed as she was for their first meeting and they headed to the pub. After getting drinks they sat and chatted for a while as if they were a normal couple. About an hour after getting there she told him to go to the disabled toilet, take off the shirt and trousers and kneel. No need for a hood this time. He was going to object but one look at the picture on her phone silenced him.
Shortly after he was in position there was a knock and in walked John. John grinned when he saw who was waiting for him. "If only I had known that a sissy lived nearby, I could have been using you every day. Hopefully Anna will allow me to make up for lost time. Now open wide sissy boi". He just opened his mouth and started to suck John's cock and felt it grow. John started gently but then grabbed his head and face fucked him hard. Soon his throat was sore and his little thing was pressing against his cage, trying to escape. After a while John unloaded in his mouth. "Don't swallow, you are to return and show Miss Anna first". John then left.
He redressed and went back to the table, his mouth closed. As he got to the table he saw that Miss Anna was talking to his neighbour Jane and pointing at him. She put her finger to her mouths, indicating he should stand there silently. After ten minutes Jane left and he was allowed to sit. "Show me". He opened his mouth and showed the cum in it. "Swallow". He did.
"Good sissy and hope you like the taste, if not you will get used to it. Now finish your drink and take me back to yours. As they were almost at his, she told him to get down on his knees and kiss her boots. He was worried about doing this in public, even if it was dark. One quick slap across the face and he went down and kisses them. Before he could get back up she raised one foot and pressed it to the back of his neck, pinning him to the ground. "Don't ever forget your place or think about disobeying me sissy. I have been gentle with you to date, maybe too gentle". |
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By (user no longer on site)
over a year ago
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Fucking hell this has me so hard |
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What a fantastic story, so well written too. |
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By (user no longer on site)
over a year ago
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This just gets better and better. What a lady |
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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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Before she removed her boot she bent down and locked a wire necklace around his neck. To most people it was a necklace, but those in the know would recommend it's significance. She told him to behave tomorrow and not let her down.
In the morning he hung outside the sex shop for a few minutes before going in, hoping it was not busy. When he went in he could not see Marie so asked the guy behind the counter if she was around. To his embarrassment he shouted out the back "Marie there is a little bitch out here to see you". Marie came out dressed in a PVC dress (may as well model the shop's clothes) and came over. She looked at sissy and asked what he wanted. He asked for a word in private and they moved to a quiet corner in the shop. Sissy quietly spoke "my new owner wanted me to come and thank you for your help the other day. She loved your suggestions and has asked me to come back and get another set, including belt". Marie smiled as she thought of the commission. "Did she say anything else to you sissy"?
"Yes she instructed me to respect and obey you as if you were her". Marie smiled and told her colleague that she was taking a break. She led sissy to a storeroom at the back and told him to strip. Within minutes he was just in panties with his plug and cage showing through. "Respects to your owner, she has you under control. Get on your knees and crawl between my legs." She opened them wide and sissy could see that she was not wearing any panties. "As your cock is caged (and doubt would be much use even if it was free) get your tongue in there and lick me. You are not leaving till I have had at least one orgasm". It is a while since sissy had done this but he used to be very good at it. He had learnt that he needed other ways to please as his little clit wouldn't. He started gentle and then flicked his tongue in and out.
Marie started moaning but then grabbed his head and held it tight. "Get on with it sissy, I don't have a long break". He picked up the tempo and his tongue was dancing around her clit. Shortly after she exploded all over his face. "With a tongue like yours you would do great in our glory hole sissy". Sissy did not want to think about that but knew he would have to mention it to Miss Anna. Marie kindly gave him a towel to clean his face and sort himself out. She tidied herself up and went out to get his order ready. He paid for it and left as quickly as he could. Marie told him to be sure and come back soon, she insisted on it. As he left he wondered what the visit to Jane would entail. |
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By (user no longer on site)
over a year ago
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This is my dream scenario |
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By *tms1xCouple
over a year ago
Chelmsford |
Caught by house mate and bout five of his mates while having fun on kitchen floor with my now wife!! They made there excuses and we joined them all in pub later! This was pre fab and swinging days |
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By *tms1xCouple
over a year ago
Chelmsford |
"Caught by house mate and bout five of his mates while having fun on kitchen floor with my now wife!! They made there excuses and we joined them all in pub later! This was pre fab and swinging days "
Ooops wrong post |
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By (user no longer on site) OP
over a year ago
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He nervously approached Jane's door, hoping that Jim would not be there. He knocked and Jane opened after a few minutes. She looked at him, smiled and said that she was expecting him. She was dressed in a black skirt and button down white blouse, almost reminding him of one of his school teachers. She led him into the kitchen and told him to sit down. She then asked what he wanted.
He quietly says "I believe you know Miss Anna. She told me to come here and apologise for not offering my services as a sissy maid to you before now. She knows that you and Jim are both hard working and as a local sissy I should have offered to help. She also asked me to deliver this package to you". Jane took the package and opened it and was slightly taken aback by the plugs and belt. She had to enquire what the belt was for.
She then says "I need to explain something to you. Jim and you may both be locked in chastity but that does not make you the same. He is my husband who I love dearly. Miss Anna is just helping us add a bit of spice and fun into our marriage. As for you, you are just a little sissy bitch for whom I have no feelings for whatsoever. So if Miss Anna allows me to deal with and use you, I can be harder on you than I would want to be with Jim. Do you understand sissy"?.
Taken aback at the harshness of her tone and words, sissy remembered his orders to obey her, so he just replies "understood Miss Jane. He was then told to strip to his panties and get on all fours. Miss Jane led him to a small room off the kitchen which had a couple of pieces of BDSM equipment in it. He was positioned over a spanking bench and strapped tightly down. He could hear her walk behind him to get something and come nearer but had no idea what she had.
Suddenly there was a loud crack as a cane stroke landed on his bare ass. Before he could get used to it another one landed, followed in quick succession by three more. She was not holding back and he already knew that it would be sore to sit down. As the strokes landed she called him names like "stupid sissy", "slut" and bitch". In total she gave him thirty hard strokes, which left him shaking and crying. She left him strapped to the bench for a few minutes. She then walked in front of him , held his face in her hands and said "that's just the start. Miss Anna has given you to me one evening a week to do my cleaning and I can be as harsh as I like with you". |
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By *titch69Man
over a year ago
Torbaydos |
Some guys have all the luck !!  |
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By (user no longer on site)
over a year ago
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Great story, I love being used |
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mmmm love this story and the names used |
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By *an2loveMan
over a year ago
Chesterfield |
Wow! Magnificent! I (lover) would be up to serve my community but would need training!! Xx |
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By *an2loveMan
over a year ago
Chesterfield |
[Removed by poster at 03/02/20 09:21:12] |
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By *ob2Man
over a year ago
dungannon |
Mmmmm fantastic |
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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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He was unstrapped from the bench and told to get on all fours and follow Miss Jane. She led him upstairs to the bedroom and the built in wardrobe, which had been adapted. There was a chair in the middle of the wardrobe. Miss Jane removed his plug and told him to sit on the chair. He gingerly did so partly due to his sore ass and the fact there was a dildo secured to the centre of the chair. It soon filled his ass. He was then strapped to the chair by his ankles, wrists, chest and neck. Finally Miss Jane added a hood that effectively gagged him but allowed him to see through two small holes. She closed the wardrobe door which plunged him into darkness but he could see bits of what was happening in the bedroom.
He saw Miss Jane take off her clothes and neatly hang them up. She then went to the bed and uncovered four cuffs that were attached to each corner of the bed. She lay on the bed and attached the ankle cuffs spreading her legs wide. Obviously having practice she managed to attach the two wrist cuffs so she was spread eagle on the bed. She just laid there waiting for something or someone.
Half an hour passed before he just about heard a noise on the stairs. He was expecting Jim to come in, though he thought Jim was the sub. Maybe they switched for all he knew. The person reached the bedroom and finally came into view. He was a bit surprised to see that it was Miss Anna. She was wearing pvc leggings, a tight top and ankle boots. His little clit strained in his cage at her outfit. She walked around the bed and gently tickled Jane on the legs, which made Jane moan and squirm. Miss Anna then walked to a drawer and took something out. As she passed the wardrobe she winked, obviously knowing sissy was in there.
She was out of sight for a few moments but when she came back into view sissy could see she was wearing a harness between her legs. There was a large thick strap on attached to it. With little preamble she approached the bed, opened Jane's legs and plunged the strap on straight into her cunt. As it entered her Jane screamed and bucked on the bed. Miss Anna removed it and shoved it in again. She soon built up a rythm of fucking Jane harder and harder. As she fucked her she asked Jane what she was. Quietly at first Jane replies "I am your bitch". As the fucking intensified Jane lost all sense of decorum and screamed out "fuck your whore bitch Miss Anna, fuck me hard". Miss Anna was quite happy to oblige. |
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By (user no longer on site) OP
over a year ago
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After thirty minutes of hard fucking with Jane screaming loudly most of the time, Miss Anna removed the strap on. Jane looked at her and begged "please Miss Anna I was so close, let me come". Miss Anna smiled and reminded Jane who was in charge. "I may let you have control over Jim and use the new sissy, but don't forget that ultimately you belong to me, isn't that right bitch?". Jane was silent for a few moments but her newly awakened desires came over her. "Please fuck me till I come Miss Anna and I will swear my life to you and do whatever you say". In the wardrobe sissy was shocked to hear this as he had always thought Jane was so polite and demure. He wondered yet again about the power of Miss Anna.
Without warning Miss Anna shoved the strap on back in to Jane's cunt hard and fucked her roughly. Within a few minutes Jane screamed out loud as she had an almighty orgasm, squirting all over the strap on and the bed. Miss Anna grinned and said "I now completely own you bitch and all your holes. Jane just weakly nodded.
Miss Anna withdrew, got up and walked over to the wardrobe. Opening the door she unstrapped and unhooded him. She forced him to his knees and shoved the strap on into his mouth. "Clean it sissy boi, it's all you are good for". When he had finished she led him to the bed and positioned him between Jane's legs and told him to lick her clean.
As he was doing this she ran her hands up and down his back and ass and fingered the plug in his ass. "I cannot wait until my strap on replaces that plug and I fuck you like you have never been fucked before sissy boi. Once I have broken you in I know that John cannot wait to fuck you". When he was finished cleaning Jane Miss Anna attached a leash to his collar and dragged him downstairs, telling Jane not go go anywhere.
Not knowing what was going on sissy could only follow as Miss Anna led him to the utility room, which had a couple of amendments added. Rings had been placed in the wall and chains attached. She attached one of the chains to his collar, after removing the leash. She then used two cuffs and more chain to attach his wrists to the wall. She left him there stating that he could stay and ponder things for a while as she carried on with Jane.
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By (user no longer on site)
over a year ago
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Ducking love this |
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By *ob2Man
over a year ago
dungannon |
mmmmmm fantastic |
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By (user no longer on site) OP
over a year ago
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After about twenty minutes chained to the wall he suddenly heard voices but could not figure out where they were coming from. They were quiet at first but then got louder. He heard Miss Anna tell Jane to undo herself and bend over the bed. He looked around and saw what looked like a speaker. He guessed the other half was in the bedroom and it was a way to tease Jim whom he assumed was normally chained here.
Next he heard Miss Anna telling bitch Jane to spread her ass cheeks. It looks like the plugs may not only be for Jim. Once plugged Miss Anna walked over to the couch (he imagined this by what she was saying). When there she told bitch to come over and lower her leggings and panties. She then told bitch to get between her legs and lick her owner to a few orgasms. It was torture for sissy to hear this chained as he was.
As bitch licked her Miss Anna outlined her plans for Jim and helping Jane take more and more control. She also mentioned that as agrees sissy would visit at least one evening a week, primarily to clean the kitchen and bathroom. He was to be in uniform at all times when working and should be kept hobbled as well. Jane was allowed to punish him as she felt was right. His ass already told him that she would not take it easy on him. All of a sudden Miss Anna let out an unlike her scream as bitch's tongue had hit the right spot. Soon she was gushing all over bitch's face, but told her to keep licking.
Raising her voice she says "hope you are enjoying listening in sissy and your cage is not too painful. I would guess you would rather be back in the wardrobe so at least you could watch. But you have not earned that yet. I am more than happy to let you watch me abuse others but you will not get to see me get sexual pleasure. You are not worthy of that". " Now enjoy your night in the utility room sissy boy".
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By (user no longer on site) OP
over a year ago
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As can be imagined he did not get much sleep in the utility closet. The chains did not allow him lie on the floor. He had to stay sat up with his arms outstretched either side. It also meant that he would not have been able to keep a blanket around him, if he had been given one. He spent most of the night wondering what had happened to him and what was going to happen. Just when he thought the worst had happened there was more to come. At some time early morning he was woken by the light going on in the room. Miss Anna approached and attached a ring gag to his mouth, keeping it open. She then added a funnel attachment which she straddled. Before he could complain her piss ran down the funnel into his gag. He had never tasted piss before and could not say he liked the taste, though in the circumstances that was a moot point. She must have needed to go as it kept coming and he was having difficulty to swallow it all. Finally she stopped, removed the funnel but left the ring gag in place. "Easier for next time " as she grinned and left. Then darkness descended again.
About four hours later the door opened and light came on but this time it was Jane who entered, but not as he had seen her last night. She was completely naked and had matching leather collar and cuffs on. She picked up the funnel put it in place and used it. It was bad enough being used as a toilet by his owner, but so much worse being used this way by her bitch. He guessed he was being
shown his place in the pecking order.
When she finished she unchained him, leashed him and dragged him back to the spanking bench and strapped him down. They were not giving him any respire. His ass was still sore from yesterday but that held no sway. Miss Jane (weird thinking of her like that considering how she was dressed) picked up a paddle, made him kiss it and then went behind him.
Without warning the hard wooden paddle landed squarely on his ass checks, followed quickly by four more. Five were then administered to the back of each of his thighs. Worried his screams may wake Miss Anna, she stopped and went to a laundry basket and removed a pair of her used panties. Balling them up she stuffed them in his mouth and picked up the paddle again. She finished off with twenty five hard wallops to his ass, leaving it red, bruised and him crying. She walked around him and said "in case you think I have gone too far and have displeased your owner she authorised this. I would keep going if it was down to me". She then walked out and left him to try and recover. |
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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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All of a sudden he felt something cool on his ass. Miss Anna told him to stay still, she was rubbing a salve on to his ass to help him recover. "I apologize sissy, I did not expect her to go so hard though I did authorise it. To understand where she is coming from you need to know more about her back story. I got to know her when I was cleaning and one day noticed she was upset. No one really looks at cleaners and often finds themselves confiding in them. It turns out Jim had cheated on Jane and she was distraught. They had been child hood sweethearts and she thought they were happy. Miss Anna consoled her and gave her some advice. Deep down Jane did not want to leave Jim but needed things to change. Hence her new control and Jim being in chastity.
Though the whole episode made her hate men and no matter how much she wanted she could not treat Jim as badly as she wanted. So when sissy came along here was her chance to be really strict with a man (in some form sissy could just about be classed as a man)".
Miss Anna continued that she thinks it helped break sissy and show him where he belonged.
When she finished she unstrapped sissy and helped him up and led him to the kitchen. He was permitted to sit, though gingerly and served a cup of tea and some toast. He wondered where Jane was and if reading his mind, Miss Anna said that she was in the utility room in a dog cage on a time out. When sissy was finished breakfast he was led to the sink and chained by the ankle. He was told to do the dishes and put them away, there was enough leeway in the chain for him to move around. Any time he did move he winced due to how saw his ass was. It took him a lot longer than it should have. When he was finished he was unchained, led to the bathroom and chained there. He had to clean the toilet, bath and sink and gathered the dirty towels for washing.
When he was done he was hoping he would be let home but he was returned to the utility room and reattached to the wall. He saw the dog cage but could not see Jane as there was a sheet draped over the cage. She was making no noise so he assumed she was gagged. |
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mistress needed to train her slut how far it may go |
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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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Cant wait for the next bit to see where this goes. |
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By (user no longer on site) OP
over a year ago
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About 7pm he was finally released, allowed get dressed and fed proper food. He sat and ate with both Miss Anna and Miss Jane, both of whom were dressed in light summer dresses. The conversation was general and light hearted. When finished Miss Anna told him to kneel down and kiss the shoes of Miss Jane as a thank you. Miss Jane smiled and said that she would expect sissy maid at 7pm on Tuesday. He was to come in uniform but she would lock on his shoes with her own locks.
Miss Anna then led him back to his where a few surprises were awaiting him. In his spare bedroom a dog cage had been set up and rings had been positioned against the wall in various places, with lengths of chain resting near by. In his kitchen a dog bowl for food and one for water has been placed on the floor. "In time this is the only place you will eat sissy but we will get to that". In the living room three dildos of different sizes had been attached to the wall at knee height. "Each evening you are to spend an hour practising on those dildos, starting with the smallest and working up. That combined with being John's personal oral whore should bring your oral skills to the level I need". "And in case you are thinking how will I know I have installed cameras all over your flat. Very easy to send to a website if you decide to fight me sissy". Now it's bed time and as I am staying you cannot sleep in your bed. Do your nightime preparations and then crawl to your cage. When he was in place Miss Anna locked the cage and threw a blanket over it. "Sleep well sissy, know I will ". She laughed as she closed the door. A good night's sleep was the last thing on sissy's mind or ass for that matter. With all these changes its just as well he did not have many visitors. He had a feeling most of his future visitors would be chosen by Miss Anna. |
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Like to see an update on this one soon |
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By (user no longer on site)
over a year ago
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Loving this |
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By (user no longer on site) OP
over a year ago
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The next morning he was released and sent off to work. Trying to act normal as if nothing had happened over the weekend was not easy, especially as he had the reminders with his sore ass. He was just glad that his young work assistant knew nothing about it or what he was wearing under his clothes. She did seem to get curious why he winced when he sat down.
After getting home and having some tea, he knelt naked apart from his cage and plug in front of the smallest dildos. He started by licking the tip of it and then licking along the length. He then opened wide and took as much of the dildo in his mouth as he could and started sucking. He backed off when he felt he was going to gag and then carried on. The hour flew by but both his knees and mouth were sore at the end of it.
After work the next day he dressed in his uniform and put a coat on over. He carried his heels and hobble chain and went over to Jane's. As soon as he was inside he was told to drop the coat and put on the heels. Using her locks Jane attached the hobble chain and then led him to the kitchen, which was in a state. It did not look like anything had been washed since he was last there. He was hobbled to the sink and set to work. Jane went off to relax and ignored him. Two hours later he was finished and Jane undid the chain but replaced it with the bathroom one. This took him a good hour to clean and tidy up.
When he was done to his dismay Jane led him to the kneeling bench and strapped him in. She used a ball gag to silence him and proceeded to smack his ass fifty times. It may have just been her hands but it still hurt. When she finished he was shaking. She left him to recover for a few minutes and then unstrapped him, unhobbled him and sent him home. "Don't forget your hour of dildo training sissy and Miss Anna is expecting you at the pub at 6.30 tomorrow evening. Don't dare be late. " It looks like another late night for sissy. |
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Mmm more cock suck trading I imagine |
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By *atexpvcTV/TS
over a year ago
chester/Merseyside |
Fantastic storey only wish it was me in the storey line |
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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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Nice |
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By (user no longer on site) OP
over a year ago
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He was so tired the next day but knew he could not afford to stand Miss Anna up so he was at the pub on time. She was already there, dressed in a white blouse, black leather skirt and black knee high boots. Just seeing her reminded him how easily she had power over him. He sat down and she quietly asked how his ass was, smiling as she did. They chatted for a few moments and then she got up and told him to follow her. She led him to the smoking area at the back of the pub and to a discrete quiet area. She lit a cigarette and blew smoke in his face. She then told him to open his mouth and she quickly deposited ash in it. He was glad no one was around to see. Every time she flicked he opened and ate her ash. When she was finished she put the cigarette out and told him to eat the butt. This was the most difficult part.
"John is waiting for your mouth sissy". Quietly he headed off to the meet in the toilets. He got there, knelt and waited. John did not keep him long and there was no chat. Dick out, in mouth, face fucked hard and then John came. As he left he said that he could not wait to have sissy at his place. Dreading that happening but knew he had no choice, he headed back to the smoking area. As they were the only two there Miss Anna told him to kneel and kiss her boots. She kept him kneeling to use him as an ashtray again and then they went back to his place.
When they got there he was told to strip and bend over the couch. She put on some gloves and removed the plug from his ass. She inspected the ass by shoving two and three fingers up there. She declared him ready for the next size plug, which she got, lubed and inserted. "Good progress sissy, soon your hole will be ready for my strap on and I can fuck any last feeling of being a man out of you. Once I have I know John wants it as well." |
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By (user no longer on site) OP
over a year ago
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" "
Appreciate your support |
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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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So wish this was me |
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By *rsPricklePantsWoman
over a year ago
Room 237 at The Overlook Hotel, Suffolk |
Not really my thing but finding it an interesting read |
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By (user no longer on site) OP
over a year ago
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As Miss Anna left him she told him that Marie at the adult store was expecting him at 7pm the following evening. He was to wear black bra, panties, stockings and suspenders under his clothes and bring some black heels. "Do not dare disrespect her sissy or there will be hell to pay.
The next evening he arrived nervously at the store. Fortunately Marie was at the counter and saw him come in. She led him to the store room and told him to strip to his undies and put on his heels. When ready she cuffed his hands behind his back and added a leash. She laid down on the floor and lifted up her skirt. Using the leash she pulled his face into her cunt and told him to get her off. He started licking and soon got into a steady rhythm. After some serious tongue action she was gushing over his face. She then pulled him by the leash and led him through the store to the video booths. Near one of them they had created a glory hole. He was positioned on the opposite side of the hole and simply told to suck any cock that came through.
The first one was stubby and small and it did not take long to make it cum. The next was longer and a bit more difficult to swallow but he took what he could. He had a few minutes break before the next one, which was the first cock he had seen with a prince Albert piercing. He nibbled at the piercing before putting the cock in his mouth and sucking him off. He soon lost count of the cocks coming through the hole. The latest one was another first as it was his first black cock. It was big and had a good girth to it. He would have liked to use his hands but they were cuffed behind him. It took him a good thirty minutes to get this cock to spurt and his mouth was sore. After about three hours on his knees Marie collected him and brought him back to the store room.
She knelt him in the centre of the room and straddled him. He just about got his mouth open before she started pissing on him and he tried to catch it all. "First time I have used a human toilet sissy but definitely not the last". When she finished she told him to get dressed and go, without cleaning his face. "By the way sissy the glory hole covers your hour oral practice tonight". He was aghast that she knew about that and he sneaked home. |
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By (user no longer on site) OP
over a year ago
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"Not really my thing but finding it an interesting read"
Appreciate it has a niche audience but thank you |
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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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Well written,interesting read... |
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By (user no longer on site)
over a year ago
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One of my fav stories |
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By (user no longer on site) OP
over a year ago
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For those interested there is a part two |
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