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my perverted mind

By *ichellesubsissy OP TV/TS over a year ago

Further down the rabbit hole

Wish this was a true story but sadly not just something from my twisted perverted mind.

I've been dressing for as long as I can remember but only explored my bi side in my late 20s, this has lead to my role changing to a submissive bottom sissy, so this is where the story will go.

I found fab by a recommendation from a friend, so I obviously wrote my profile and uploaded pics. It was quite a while before I got any response but one of the first I got was from a man in fifties called Charles, he lived on his own, travelled a lot due to taking early retirement and enjoyed the finer things in life. We chatted and he sounded just what I was looking for, he was domineering and was looking to enjoy teaching sissification to a willing subject.

We agreed to meet socially to see how we got on and whether there was a connection. I was very nervous as the date got nearer, but dressed normally I went to where we’d arranged to meet for a drink. We meet at the bar like 2 work colleagues meeting for a catch up. Charles and I sat in quiet corner and after half hour of general chat the conversation it turned to what we were both looking for and what he expected from me. He told me that he'd prepared a contract for to read and sign and after signing that any deviation from it would result in severe penalties. I was beginning to get really excited about the prospect of being someone’s property, being used and abused and commanded what to do. He went on to explain that I'd be sent daily tasks to perform, they would be easy to do at first but would slowly be more and more degrading, humiliating and deprived.

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By *ichellesubsissy OP TV/TS over a year ago

Further down the rabbit hole

I signed the contract without really reading it, I was just so excited, horny and thrilled to finally have found what is truly been looking for. He told me my first task would be sent in the morning I would then have till 11 pm that evening to send photo or video evidence, again failure to do so would mean the next task would be even more demanding. With that we finished our drinks and walked to the car park, he told me to walk with him to his car when we got there he roughly put his hand down the front of my pants and took hold my cock and balls and squeezed hard, he then leaned in and said ‘you won't be needing these any more, there useless, limp and pathetic, don't you agree?’

‘yes’, I whimpered.

‘now, get on your knees and suck a real man's cock’. he ordered.

‘Here? Now?, in the car park?’

‘yes, your nothing but a cheap cum whore’ he said and slapped me hard leaving his red hand print on my face, but dutifully I got on down my knees and opened his fly, taking his flaccid cock out I began stroking it hard, then I opened my mouth and started to take it in gently but he grabbed the back of my head forcing it right to the back of my throat, my gag reflex kicked in and I started choking.

‘We're going to have to work on that whore, I love being sucked deeply but your not doing your best yet.’

With that he moved my head forward and backward, I could feel and taste pre cum dripping from his big hard cock, then suddenly he moved my head faster his cock twitching and cumming in my mouth.

‘don't you dare spill a drop’ he growled.

I swallowed every last drip, the salty taste felt good in my mouth. I then stood up and Charles said 'good gurl, you'll definitely make willing sub. Now go home and think how you can improve and please me more. I'll be in touch.'

He got in his car and drove away, I wandered aimlessly over to mine thinking of what I had just done, who had seen me doing it? No I said to myself, this is what I want humiliation and degradation. By the time I got home I was so excited to see where my journey would lead me. I showered and dressed for bed in my silkiest nightgown and went to sleep.

6 am the next morning my phone started beeping I firstly thought it was my alarm but no a text, I opened it up and it read, 'Morning my sissy slut, from now on your will refer to me as SIR, MASTER or DADDY. Now your first task, its a easy one, I want you to wank in to a pot of yoghurt then eat it. This will be the last time you cum by wanking and the last time you get hard slut. I want this all videoed and sent to me today. I want your face visible, for you to say your slut name and call out DADDY when you cum.'

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By *ichellesubsissy OP TV/TS over a year ago

Further down the rabbit hole

Oh that was such a thrill I couldn't wait to finish work and shop for yoghurt! The day felt to drag for so long but at last 5pm arrived. Straight to the shop, oh a flavoured one or just plain one? Who cared I thought I'd still get the same result. Rushing home I stripped off, showered, shaved and dressed in a basque, and stockings. I was too excited to do my make up I just wanted to please my MASTER. I set the camera up ready got my yoghurt pot ready, put on some sissy porn opened a fresh bottle of rush and started slowly stroking. The rush of the nitrate and the real excitement I felt I some came in the yoghurt, I then took my first spoonful, oh god I felt so dirty but happy that I'd be pleasing my MASTER.

I sent the video and waited for a reply. I knew he had received it and read it but nothing back, had I done it right? Was he pleased with it? God, the wait was agonizing but eventually he responded, 'well done slut MASTER is pleased, however I have another task for you for night. I want you bend over and whip your arse saying what a good gurl you are. I await your video slut!'

Another task, already I thought but I again set the camera up, got my riding crop out bent over and began whipping my arse, it hurt but I was enjoying so much.

Again I sent the evidence over, 'excellent slut MASTER likes. Now enjoy the rest of your evening and we'll speak tomorrow.'

The rest of the week the tasks kept coming, one day I was wear a butt plug all day. One involved me pissing in a glass and drink it. Each I fulfilled my duty as required. This went on for about 2 weeks, proving myself that I ready to be sissified. Bank holiday was coming up and I was looking forward to a break from work, Charles asked how would I feel spending the weekend with him and progressing further with my training. I jumped at the chance, a weekend away in a nice house? Who wouldn't?

He told me only to pack my feminine clothes as once I arrived at his on the Friday evening I was leaving my male mode at the door and being Sara for the weekend. As I set of for Charles house I was excited about being able to dress all weekend with no one judging me. I drove up to his house a text arrived telling me the garage door was open and to park in there. I pulled in the large double garage which was completely bare of anything. I turned the engine of and got out the car, I saw a note on the door leading to house, 'Hello Sara, now you arrived before I close the garage door and you enter the house I want you to strip off, put some lingerie on,your sluttiest outfit, lipstick and a wig. Don't worry about being fully made up that will happen later. Leave your male clothes and your phone and car keys in the boot of your car. Then and only then will you get access the the house properly. I am watching you.'

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By *ichellesubsissy OP TV/TS over a year ago

Further down the rabbit hole

What was I to do? I was in full view of the entire road! Anybody passing would see what I was doing! Suddenly a light went on in the garage making it so bright like it was the middle of day! Could this get any more humiliating I thought. Should I get back in my car and drive home? No this I want we'd discussed and deep down want I wanted. I opened the boot and took my suitcase out and started undressing. Once naked I felt the cold bite against my skin so quickly opened my case and started to dress, first my panties, then stockings and basque, wig, heels and my little black dress, I used my door mirror to a apply my lipstick. I put my clothes, phone and finally my keys in the boot and closed it. Then the garage door started to close, I just hoped no one had seen me. There was a loud click which I realised was the door to the house unlocking. I got hold of case and walked and opened the door. Stepping through I was engulfed in darkness, the door closed behind me, again I heard a click, checking the handle I found it locked. No way of backing out now I thought.

I stepped further in to house, too nervous speak or call out. Suddenly I was grabbed from behind, I felt a cloth pushed over my face, I felt dizzy and then I must have fallen asleep.

Not sure how long I was out but when I tried to open my eyes a splitting headache overcame me. I was lying down but other than that I wasn't aware of anything else. Then I heard Charles speak, 'ah, good your awake, I'm going to give you a couple of pills and a drink and try to relax.'

I felt tablets enter my mouth and then a glass I took a drink but it wasn't water not sure what it was I drank it then again must have fallen asleep.

Next time I woke the headache was gone which I was glad about but on trying to move I couldn't. I sensed movement to the side but I couldn't even move my head. Then a face appeared, it was someone I'd never seen before. 'hello there, I'm Karen, I'm a friend of Charles and I'm here to help you. You are currently restrained for your own safety. Firstly, I'm going to give you an injection.'

'OK' I replied nervously.

I felt the needle going in and a cold rush of liquid enter my body. 'this first one is to make your sissy clitty limp forever, we use to remove the cock and balls completely but then that takes away the feeling of true denial. Now I can see you shave all over but I am now going to use electrolysis so you'll never have to pick up a razor again. Happy with everything I've said?'

'yes I'm OK with that.' I replied. 'good, because you've not really got a choice in the matter have you sissy slut.'

After the electrolysis had finished, Karen said 'OK next is your breasts, I see you have very small ones at the moment but I'm going to give another injection that will develop them slightly bigger.' Again I felt a needle and a mystery liquid enter my body. 'OK last but not least I'm going to give you a drink. Enjoy.'

Again I fell asleep after drinking it. Coming round a third time, no headache and with the ability to move. I raised my head, no idea where I was, it was bedroom, tastefully decorated and light but no windows. I sat up I was dressed in one of my nightdresses and had a wig on, I looked at my hands and saw my nails had both been manicured and painted a lovely pink colour. I swung my legs on the floor and saw my toenails had been painted the same colour vanish, something I'd never done. I stood up and headed for the en-suite. A shower was in order and to take stock of things as I was still unsure how much time had passed. I turned the shower and tried to remove the wig, I couldn't it was somehow fixed on and wouldn't come off! What had happened? I only remember bits but not this! Shocked I sat down on the side of the bath and started to cry, what had I become. Pulling myself together I stood undressed and climbed in the shower, scrubbing and cleaning myself I noticed my cock had shrunk and my balls nearly disappeared, now things were starting to come back, the injection. Wow it had really worked. Ha I laughed to myself this does feel good, I had to finally admit.

I finished the shower, wrapped a towel around myself and went back to the bedroom, I was a bit taken aback to find the bed made and clothes and underwear laid out for me, someone had been in without me knowing, that creeped me out a bit. Also was a note, 'Please dress and come down for breakfast'. Well at least I knew it was morning but which one? I slipped the panties on feeling how they fit so much better there wasn't an unsightly lump at the front, I then sat down at a dressing table and started to apply my make up, hopefully simple and feminine, then the stockings and my lovely black basque, all that was left was my maids outfit and heels.

I walked to the door unsure what I'd find beyond. Opening it it was just a normal first floor landing and stairs leading both up and down. Well the note did say down so I nervously headed down the stairs. Charles appeared at the bottom, ' hello Sara, well you do look really sissified. Now come here I have a gift for you before we eat.' 'Thank you MASTER!' came my stuttered reply. I followed him in to the living room he told me to stand in the middle of the room. He then came up behind me and suddenly put a collar around my neck. It became tight and then I heard a lock going on. 'OK I'm now going to lead you round on your leash, your my property now slut. OK?'

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By *ichellesubsissy OP TV/TS over a year ago

Further down the rabbit hole

'Yes' I said. A hard smack across my face, 'you didn't respond correctly did you?'

'No sorry MASTER.'

'Better, but you need to be punished slut, get on your knees and lets practice your gag reflex!'

He dragged the leash down forcing me to my knees, 'open my zip with your teeth, your not going to use hands.' I eased forward and grasped his fly in my mouth and pulled it down, his cock sprang out, it was fully erect this time. I greedily started to lick and stuck the purple head, making it more and more wet before sliding my mouth all the way down the shaft, backwards and forwards I began to suck and lick it. ' oh Sara, I've another surprise for you'. He then started to piss in my mouth, 'drink as much as you can slut.' there was so much I couldn't drink it all I ran down chin over my dress and on the floor. Another slap, 'you filthy whore you'll clean that up afterwards.' He pulled his cock out and started to cum all over my face. 'leave it there slut, till I tell you to clean it up. Now lets eat.'

He pulled the leash tightening the collar, 'stay on your knees slut.' he dragged me on all fours to the dining room, the table had been laid out ready for breakfast. Charles sat down and I started to get up so I could sit as well. 'what are you doing slut? You eat from the bowls in the corner.'

'what MASTER?' I whimpered.

'You eat from the bowls in the corner, what don't you understand you thick slut?' he rose quickly from the chair and kicked me in groin. I nearly fainted with the pain and the sickness I felt.

'NOW DO YOU UNDERSTAND SLUT?' he screamed at me.

'yes MASTER' I sobbingly replied. He dragged the leash and pulled me towards the wall where the bowls where. He then attached the leash to a hook, 'I except them to be clean by the time your finished.' 'yes MASTER'.

I looked down and saw that one bowl had some sort of food in it and the other liquid, I lowered my head tasted the food, it tasted disgusting but not wanting to feel any more punishment so quickly I emptied and licked both bowls clean. I looked up and saw that Charles had left. Being tied to the hook I was unable to do anything but wait. A few hours must have passed before I heard heels coming towards the dining room and a woman appeared, it was the woman who'd injected me, was it Karen? Somehow I seemed remember it was. 'hello Sara love, my, you look different from last time we met. Come on lets get you cleaned up.' with that she undid the leash told me to stand and follow her. My legs were wobbly from kneeling for so long but somehow I managed to walk with her. We went back upstairs to the bedroom where I was before. 'Sara, start getting undressed, I'm going to run you a bath.'

I did as she said and then went to the bathroom, she pulled out a key and undid the collar, 'you don't want to get that wet' she chuckled, she had run a lovely hot bubble bath, in I climbed and she started to wash and clean me, I started to relax more and more, feeling her soft hands all over my body. 'there your all done now come lets sort you out properly.' I got out and she started to dry me with a big fluffy towel, she started paying particular attention to my arse, squeezing my cheeks, pulling them open, then she slid a finger to my hole, good it felt so nice, I could feel myself opening up to her touch. She brought her finger up to my mouth, 'lube it for me Hun.' I eagerly took it in the mouth wetting it thoroughly, she eased it back to my hole and so gently slide it inside me, touching my prostate, I could feel pre cum dribble out I put my hand down and wiped it up before licking it all off my hand, her finger sliding in and out massaging my prostate, god I was horny but couldn't get hard! Cum started to leak out. Karen whispered in my ear 'this is called milking, I will make you cum but it will leave you frustrated and unfulfilled. You cheap whore'.

'oh yes!' came my reply. I was enjoying to much to care. Suddenly she withdrew her finger, 'OK we're done for now, lets get you dressed and ready.' I followed her to back to the other room and sat at the dressing table. Karen started to brush my hair and apply my make up, she was applying it quickly and professionally than I usually do, 'Charles likes this kind of look and you will learn to do it this way to.'

She told me to stand and bend over the bed, unsure of what was next I did as she told me, I felt her rub lube over my hole, 'relax' she said, then a butt plug, a big butt plug! Started to be pushed in me, 'stop resisting Sara, you know its what you want.' and then with a big shove it was in, I let out a squeal with both the pain and pleasure. Then she handed me a pair of black panties, once on she put a waist clincher around me and pulled it tight. 'this will give you a more feminine figure, that's until the injections start working.'

'injections?' I asked and suddenly felt a needle in my arm and the cold liquid enter. 'what was that?'

'oh just a little bit of hormones Hun, nothing to worry about. Now lets get you properly dressed.' stockings, suspender belt, bra etc., then the dress, it was gorgeous, a lovely dark blue fell just below the knee with a split up the side that was nearly to the waist and 6 inch black patent heels. 'there' said Karen, 'your all done, take a look.' pointing to a mirror. I made my way over the plug moving and stretching my hole, when I got to the mirror I didn't recognise the person looking back at me. I filled my bra out better than the padding I was use to seeing, my make up looked sublime, dark smokie eyes, false lashes and dark lipstick. I could have cried I was that happy I'd finally achieved the look I wanted.

'OK lets go we don't want to keep Charles and his guests waiting.' Karen said. 'oh one last thing' as she reattached the collar.

She opened the door and started towards the stairs that headed up. I followed behind until we got to the top where she opened a door and told me to go on in. I did and while my eyes adjusted to the light I heard the door close behind me and lock. OK I was here to stay I thought.

I started to look round there was several bondage tables, wall and ceiling restraints and paddles, whips, crops and canes mounted on hooks. Then I saw Charles sat naked, with 3 other men sat nearby, all naked. 'come on in Sara, give use a proper look.' As I stepped closer one of the men leaned forward and said, 'fuck me Charles you've certainly surpassed yourself this time' and started stroking his cock vigorously. I stopped in the middle of the room unsure what to do next. 'OK Sara, you remember the contract you signed? Well this is one of the clauses. You are to please my friends here. If they don't leave here full satisfied you will be harshly punished. They have paid a lot of money to be here. Got it?'

'Yes MASTER, I understand'.

'good to hear it Sara. There are no safe words there is no rest or breaks until they are all satisfied. Now lets get started.' he stood up and came towards me, an evil look in his eye. 'I'm looking forward to ruining you!'. He then took a cane from the wall 'bend over and hold your ankles,' he commanded 'do not cry out. If I hear any noise out for mouth I will hit you harder and longer, OK?'

'yes MASTER,' I replied as I bent over and clutched my ankles, I felt a gentle tap from the cane on my arse but I knew worse was to come. Then I heard the whoosh and the sharp sting across my cheeks, I took an intake of breath trying my best not to cry out but it happened, I heard laughing from the other men, as they could see what was going to happen. Crack! A harder stronger smack, tears formed in my eyes, biting on my lip I didn't cry out again. 'OK, stand up slut, its some else's turn now.'

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By *ichellesubsissy OP TV/TS over a year ago

Further down the rabbit hole

A large gentleman stood up, he must have been about 70, all hairy with a small cock. Charles mocked him saying 'looks like the Viagra not worked then!' this got a laugh from everyone else but he just said 'fuck you Charles I've given you a lot of money for this.' with that he grabbed my collar and dragged me down to my knees. 'fucking suck it bitch', he was so hairy I struggled getting to it but eagerly took to my task, sucking it quickly trying to it over with, but no he wasn't cumming any time soon. 'fucking hell she's got some suck on her Charles. Get up bitch I want to see your sissy clit and arse.'

I stood up and he eased my dress you, rubbing his hands over my stockings and then the front of my panties, 'no fucking lump there lads, this ones a good one.' He then shoved his hand inside my panties and roughly started rubbing my now tiny clit. Then pulling my panties down his hand went round to my arse, he touched where the cane had hit me it it was really sore and he must have realised it as he pushed harder against the welts, pain coursed through me but I couldn't cry out as it would only make things worse. He got to the plug and pushed it in further, stretching me more. 'OK I've had enough for now, pull your panties up whore, make yourself presentable again.'

He walked back and took his seat, next a young man got up, he came over to me and put his hand around my neck and kissed me very passionately, his tongue in my mouth I could taste him, all minty and fresh. He pulled away and whispered in my ear, 'don't worry gorgeous I'll be very gentle with you, I promise.' he walked to the wall and removed a blindfold and gag, he put both on me, took my hand and guided me somewhere in the room. He raised my arms and I felt cuffs go round my wrist and then pulled further towards the ceiling, next cuffs around my ankles and suddenly my legs pulled apart, was star shaped but stood up what was next?

I felt breath in my ear and a voice said 'you know how I said id be gentle I lied!' then a sharp smack on my arse. I tried to cry out but the stopped me. Then he kneed me in my groin, again I couldn't cry out the pain overwhelming. 'you like that you filthy bitch, DON'T YOU?' he screamed. Then my dress was ripped from me, as I felt it fall down a shiver went through me. 'Do you think this one lads?' 'oh yes', came the response. I felt a stinging pain across the back of my legs, one after the other they kept coming. Then across the front of my legs and then my stomach, 'that's going leave a mark!' said a voice. On and on it went until I was numb to the pain but I kept being slapped. It finally stopped whatever was holding me in position was relaxed. I was uncuffed and pushed forward, I felt something in front of me. A hand on my back pushed me down until I was bent over what I thought to be a table, my hands and arms were again tied up, followed by my legs. My panties were then pulled down and then ripped off. My plug was jerked from my hole, 'fucking hell that's a ready hole'. Then something big was pushed against my hole, this was bigger than I'd ever took before, please use some lube I was crying out, but it was just muffled because of the gag, then I could feel being pushed with some force in me, stretching my hole wider and wider, the pain was again so intense. Finally it slide in but just as soon as it was dragged out again, in and out it was pushed till there was no more resistance. 'ready for my cock bitch?' I heard him spit then his cock pressed against my hole and he slide it in. fucking me so hard and spanking my already sore arse while he did, then my gag was removed and a cock shoved in my throat nearly making me gag but I sucked hard moving forward and back with the fucking motion from behind, 'she likes being spit roasted lads, oh fuck im going to cum', came a voice. 'don't you dare cum in her, none of us want sloppy seconds!'

'Quick move!' said someone and the cock I was sucking pulled out and another one replaced it, then shot cum deep down my throat. 'OK I'm done for now' came the voice, 'next'. I sensed someone else behind me and a cock enter me and again the rocking motion started, going deeper inside. My mouth was again opened up with a cock, I knew this was Charles, I hoped I was pleasing him, as knew I was going to be in pain later but didn't want any more. I could feel the cock fucking me twitch and then hot cum shot in my hole. 'oh for fucksake I said no sloppy seconds' cried a voice, 'we'll just have to cum over her face now!' I was quickly untied and pushed to my knee, 'take as much of this as you can', said a voice. My hands where grabbed and wrapped round two unknown cocks, I started stroking them both, 'OK you can face fuck her till your ready to cum lads' Charles said and with that a cock was thrust in my mouth. The back of my head was grabbed and I sucked hard. Very soon it was pulled out and I felt cum over my face, one of the cocks I was wanking moved to my mouth, again I sucked and licked until he pulled out and wanked over me. Cum was dripping down my chin I was trying to swallow it all before another load came over me.

'OK lads, I think your all done, agreed? Have you all enjoyed it? Are you all satisfied?'

'oh hell yes' came the collective response.

'good well that's it for this session then. Sara you stay there I'll deal with you shortly'.

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By *ichellesubsissy OP TV/TS over a year ago

Further down the rabbit hole

I heard footsteps and the door unlock and they descended the stairs. I stayed exactly where I was, fearful of any repercussion should I move. Then not long after the door opened, 'you've done well Sara, for a first time. But I not entirely happy, my guests are but they easily pleased. I must punish you understand don't you?'

'Yes MASTER I do understand.'

'Good, stand up, remove your blindfold and come with me.'

I stood, half naked wearing nothing but a bra, suspender belt, laddered stockings, heels and leash and collar. He headed for the door and I followed, we went down to the ground floor and to the door leading to the garage. Was he sending me home? He opened the door, I was shocked the garage was empty! My car was gone. 'where's my car?' I started to utter. 'oh Sara again the wrong response, your car is being looked after by a friend and will be returned it due course. Now get in there.' It was freezing, damp and dark. 'this is your punishment, your going to spend the night in here,' he grabbed the leash and dragged me in to the garage. He pulled some chains from the corner and wrapped them round a frame on the roof before removing my bra and restraining my arms. 'I'll see you in the morning' he said and left. There I was cold, afraid and the pain starting. There was nothing I could do to stop from crying, tears rolled down my face, how had I got this bad so quickly. Nobody knew where I was, I couldn't contact anyone as my phone was in my car which was god knows where. I sobbed most of the night and in to the next morning, if anyone heard me no one came. Light began to appear under the garage door, I had to stop crying as I was sure it would bring more extreme punishment if Charles found me upset. Was cold, hungry and in a lot of pain when finally the door opened and Charles walked in. 'I hope you've learnt a lesson here Sara?'

'Yes MASTER, I have, thank you.' He unchained me, 'right go clean yourself up.' and left me. I rubbed my wrists they were red and extremely sore but again so yes the rest of my body.

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By *ichellesubsissy OP TV/TS over a year ago

Further down the rabbit hole

My legs felt like jelly through standing all-night I bent down and removed my heels, I knew there was no why I could walk in them. I was still worried where my car and belongings had gone but knew further asking would mean more punishment, I started walking to the door my whole body screaming in pain but somehow I made it through the door, up the stairs and to the bedroom I had been using. Removing what was left of my underwear I climbed in the shower. The sudden hot water hit the welts on my back, arse and legs and hurt like hell but I continued to shower. Feeling clean but extremely tired I wrapped a towel round myself and headed for the bedroom.

Sat on the bed was Karen, she looked pleased to see me as I walked towards her, 'hun you look a real mess!' she said, 'come here I'm here to help'. I sat on the bed next to her and see slide the towel down to look at my back, 'oh, they did a real number on you, we need to put some cream on that we need you ready for and looking good for next time.'

'Next time!?' I whimpered, 'how long am I here for? How long have I been here already? When can I leave?', then I started to cry again.

'Sara, hun, did you read the contract properly?' Karen asked. 'Not really' I cried.

'Oh you silly, silly gurl. You've been here 3 days, its Monday today. Your here for as long Charles wants you here. You should have read the contract my dear. This is your sissification course that you signed up for.' laughed Karen. 'your his little toy to use and abuse as he sees fit. Your other life is over. There is notification gone out to everybody that knows you that you've gone to find yourself and don't know how long you'll be away but your OK and will be in touch as and when.'

Oh my god I thought what had I done. I didn't think it would this extreme, my life as I knew it was over! Karen helped me stand up, eased my towel down and started to gently rub lotion on to my back, it felt soothing and relaxing at the same time. When she had finished she went to the wardrobe and pulled out a lovely nightie, 'put this on hun and get in bed you need to rest.' she said, I nodded and climbed in to the bed. 'oh just one more thing' she said, too tired to ask I just nodded. Then I felt the needle go in my arm and then a nothing apart from a dream state.

I wasn't sure how long I slept for but when I came round I found a table next to the bed with a plate of food and a jug of juice and a glass. I think about what I was eating or drinking I just devoured it all, as I was famished. I then started to notice how the material of the nightie rubbed against my nipples, they felt so sensitive, I put my hand to them and realised that both my breasts and nipples had got greatly bigger, they felt unnatural on my but such a turn on. There was a knock at the door, 'yes?' I queried. The door opened and Charles came in, 'hello my love, hope your well rested and recovered.?'

'yes. MASTER, I am thank you.' I replied.

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By *ichellesubsissy OP TV/TS over a year ago

Further down the rabbit hole

'Good, I can see Karen is making progress with the rest of your sissifaction. With regards to yesterday, that was just a taster of what I've got planned for you. With each day you will become more and more willing. I going to break you my dear.' he sneered. 'now the rest of today is rest and recovery, but I expect you to be ready tomorrow. So feel free to explore the house, if you need anything just look for Karen, she's usually in the office upstairs.' with that he leaned towards me and roughly kissed me thrusting his tongue in to my mouth. I willing responded and started to embrace him, he pulled away quickly 'oh no' he said, 'that can wait'. With that he stood and left.

So there I was sat on the bed unsure what was coming up tomorrow, no I had not to worry about that till tomorrow. So I got up and went to the wardrobe, opening it I found it was stocked with dresses, blouses, skirts, outfits, nightwear, leggings etc., all in my size and on the bottom heels, boots, pumps again in my size. I picked out a pair of black wet look leggings, a black blouse and a pair of low black heels. I then went to the chest of drawers, on opening the top one, panties, thongs, shorts, every colour and style. I choose a lacy pair of panties and moved to the next drawer down, this was full of bras, choosing a black tee shirt bra I decided to check out the other drawers. Next one had cami basques, basques, suspender belts. The bottom one was full of stockings all still in there packing, black, white, tan, red, seamed, hold-ups and fishnets. I couldn't count the amount there was so many. I took the clothes I had and walked back to the bed, removing the nightdress I started to change in what I had picked out. I filled the bra really well I had to admit and the cleavage looked very sexy. I had to brush my hair, still unsure how the wig had been permanently attached. Brushed my teeth, picked up my tray that had the food on and headed downstairs. I found the kitchen without any problem, so cleaned my plates and made a coffee for myself, so Charles did say I could explore, mug in hand, off I went. I found the dining room where I had eaten before, next was the living room, very modern spacious with an amazing suite. Then I saw the front door, dare I open it? I went towards it, it was locked. No surprise there I guess. So I turned round well that was it for the ground floor, what about the floor my bedroom was on. OK I knew which was my door so lets look in the other rooms, another bedroom exactly like the one I was in but this one had windows.

Next door opened up in to much grander bedroom, this was obviously Charles' room. A massive bed wouldn't have fitted in most normal rooms, it was huge. There was really nice artwork all round the room, and an en-suite and walk in wardrobe.

OK I thought lets do the final floor, I might even find Karen and get some more questions answered. There was only 2 doors up here, opening the first one was the room the had been where the entertainment had been, I could now take a proper look around. I stepped in and a chill ran down my spine, I could now take everything in and it was quite overwhelming. Every shape, size, colour of butt plugs and dildos on one wall, another wall had the whips etc. I'd seen before along with the restraints and cuffs. OK I'd seen enough I was pretty sure I'd be here again. I turned the light out and shut the door. Well only one door left, walking towards it I knocked on before opening it, Karen sat behind a desk reading off a computer, in a room that had monitors across one wall, glancing at them I realised they were views of every room I had just been in, different angles but definitely the rooms.

'Hello Sara, Charles told me I might be seeing you today. Have you made yourself at home? Oh I don't really need to ask do I hun. I've watched you have a look around. Charles keeps a very secure house.'

'Karen, was everything that happened yesterday monitored as well?' I asked;.

'Yes of course, it was all recorded as well, but don't worry no one well every see it, unless you do something really silly and upset Charles. Then unfortunately it will be broadcast everywhere. But I don't think your stupid enough to upset him are you?'

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By *ichellesubsissy OP TV/TS over a year ago

Further down the rabbit hole

'I hope I don't no' I said 'I am trying my best'.

'Well that's all you can do' replied Karen 'now I've got things to be getting on with so you run along'. With that she turned back to the screen and started typing. With my cue to leave I got up and headed downstairs I felt the need for something stronger than coffee.

Back in the kitchen I started to look through the cupboards, oh a bottle of gin, picking a glass and finding tonic in the fridge and ice in the freezer I poured myself a large drink and raised the glass to where I assumed one of the cameras where. 'Cheers' I mouthed taking a big slug. I headed for the living room, taking a seat on the sofa I found the remote and turned the TV on, suddenly I was smacked on the hard round the head, making me lose focus for a second, then a voice screamed at me, 'YOU FUCKING UNGRATEFUL WHORE!!'. I spun round there was Karen who looked absolutely furious, 'FUCKING STAND UP YOU FUCKING SISSY' she screamed again. I jumped to my feet not understanding what had brought this on. 'YOU THOUGHT YOU'D TAKE THIS PISS WITH THAT LITTLE STUNT TO THE CAMERA DID YOU!!'. Suddenly I realised what she was talking about, 'Karen, no that wasn't my intention at all' I cried back. A hard slap to my face sent me spinning away. She stormed round the sofa grabbed my arm and starting dragging me towards the stairs.'Karen, I'm sorry, I didn't mean anything by it honestly!'.

'TOO FUCKING LATE' she screamed back at me continually dragging me upstairs. We got to my bedroom she opened the door and flung me in. 'WAIT THERE SISSY', she shouted. The door slammed shut I just stood there in shock. Then the door flung open and Karen stormed in wearing the biggest strap on I'd ever seen, it must have been five inch in girth and twelve inches long, it hung there from her waist like a big black rod.'OH YOUR GOING TO FUCKING LEARN YOUR LESSON NOW!'. With that she flung me face first towards the bed, then I felt my leggings being yanked down, my panties pulled to the side, 'NO LUBE TODAY FOR YOU SLUT' Karen shouted 'THIS GOING TO FUCKING HURT BITCH!', then suddenly she slammed the strap on in me' I screamed out in pain but she just kept ramming it in and out, 'OH LOOK YOU FUCKING WHORE I'VE MADE YOU BLEED, WHAT A FUCKING MESS YOUR MAKING!' I kept crying out for her to stop but she kept on like a woman possessed, smacking my arse, raising up the red welts from the beating last night. I was on the verge of passing out when she stopped, pulled out and said 'get yourself sorted, you look a fucking mess.'

The door slammed shut but I couldn't move I was in too much pain, my hole felt like it was fire, it felt wide open, I could feel fluids running down my leg, it could only be blood. God I thought how with I recover for this. I stumbled to my feet pulled my leggings up and went to clean up. I pulled loads of toilet paper waded it up and placed it gently in my panties against my hole. I went to bed and tried to sit but it hurt too much the only option I had was to lie face down on the bed.

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By *urvygirl75Woman over a year ago

chester

Wow just wow!!

keep this going!

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By *amantha_kelTV/TS over a year ago

Magherafelt

Great story can’t wait for more

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By *ichellesubsissy OP TV/TS over a year ago

Further down the rabbit hole

"Wow just wow!!

keep this going!

Thank you hopefully more tonight x

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By *ichellesubsissy OP TV/TS over a year ago

Further down the rabbit hole

"Great story can’t wait for more"

Thank you hopefully more tonight x

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By *ichellesubsissy OP TV/TS over a year ago

Further down the rabbit hole

While writing this I've been rereading it, i've noticed some things missing so either i can carry on or post the revised edition. Your opinions would be appreciated x

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By *imale38Man over a year ago

Barnsley

Great story.

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By *asmin999jmTV/TS over a year ago

wakefield

Wow amazing

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By *4u2007TV/TS over a year ago

central

Nice

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By *es for funMan over a year ago

port talbot

Keep going bitch

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By *asey666Man over a year ago

Dublin 13

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By *ichellesubsissy OP TV/TS over a year ago

Further down the rabbit hole

I lay there letting the pain ease, I knew my hole was destroyed and never be the same again. How had been so silly. How far would this go, I couldn't begin to imagine but this is what I'd unwittingly signed up for no one to blame but myself. Once the pain had subsided I raised myself of the bed and started to undress, my clothes were a mess, but so was I. I was stood naked when the door opened, Karen entered, she seemed a hell of a lot calming then when she was last here she looked me up and down and said 'hope you'll be more respectful now?'. 'Yes, I will Karen, I promise'.

'Good' she replied, 'Now put this in, it'll help with the pain and your training, there's some numbing lube on the side' and tossed a large butt plug to me and then turned on her heel and walked out. Well at that moment I would use and do anything to help. Showering and cleaning up myself up I rubbed lube round the plug, then round my hole, hoping the numbing would be immediate and started to insert it. It just slide in with ease, oh it felt cold but the relief felt good. Then another visit to wardrobe and chest of drawers, this time I choose lilac bra, matching lace panties, a slip, ankle boots and knee length long sleeve black and lilac dress. I then sat down and redid my make up. I tried to get as good as Karen had done but I know that would take practise. I stood up and felt a sharp pang of hunger, now unsure of what reaction I'd get I was reluctant to head down but I was famished. On reaching the bottom of the stairs I heard voices coming from the living room. Not wanting to cause any more upset I went straight to the kitchen. Again I started opening cupboards looking for anything to eat when Charles and Karen appeared, 'Oh there you are' said Charles, 'Karen has informed me of your indiscretion and that she has disciplined you accordingly, however I don't think it was enough, come here now!' he demanded. I approached him bracing myself for the worst. 'on your knees where you belong sissy' he said. I knelt before waiting for strike to come but it didn't instead Karen handed him something, he opened it out before, 'this my dear is a posture collar, you shall wear it now from when you up to when I permit you to sleep'. Then suddenly it was round my neck, forcing my head upwards, I couldn't turn my head or look sideways or down. 'now your comfortable in it my cock awaits, SUCK IT WHORE!' he unzipped his fly and forced it in my mouth, Karen laughed and took hold of my head thrusting forward on to his cock all the way down. 'Good gurl your learning, no gagging this time' he chuckled. With my lips closed tight around his big throbbing cock I was forced backwards and forwards from tip down the shaft to his balls, sucking with all energy and will. 'oh god I'm cumming' mumbled Charles, Karen shoved my head forward until his cock was right at the back of my throat, she held it there and then a sudden twitch and the hot salty cum started shooting straight down the back of throat, now my gag reflex started but I couldn't move, she held my head so tight I had no choice but to swallow it all, retching while I did. 'oh thank fuck I needed that' Charles said with Karen still holding my head tight on his cock. She started to ease her grip, I pulled back from Charles cock, I could still taste the saltiness from his cum.

'Lets eat' Charles said, he then attached another chain leash to my collar 'stay on your fucking knees' and started do pull me towards the dining room. On getting there he attaches the leash to the hook and Karen starts to serve dinner. She places two plates on the table, the food looks so nice and then empties a tin of dog food in to my bowl. 'What?' she says looking at me 'you thought you would eat with the us?' . She laughs as she walks to the table. 'oh she deserves at least a glass of wine' Charles says as he gets up with a bottle of wine, he pours some in to my second bowl then starts to undo his fly, remove his flaccid cock, oh god I think am I going to have to suck him off again before I can eat, no he starts to piss in to the wine! 'I expect clean bowls' he scowls as he walks away. I bend my head and start to eat and drink as I'm famished, it all tastes disgusting but I need it. Karen and Charles are just sat eating, laughing with each other not paying any attention to me.

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By *amantha_kelTV/TS over a year ago

Magherafelt

Fantastic story

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By *asey666Man over a year ago

Dublin 13

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By *ichellesubsissy OP TV/TS over a year ago

Further down the rabbit hole

I kept knelt there, clean bowls in front of me, I started to daydream thinking how Karen and Charles knew each other, I thought that may be they were brother or sister, no, ex wife, definitely not, maybe she was a pupil like me and that I could finish like her, I started to smile thinking about it. 'Oh look' came a call from the table, 'Sissy whore is being to enjoy itself', it was Charles.

'Oh looks like the training isn't sever enough, if its enjoying it' Karen replied. 'Well, it will learn tomorrow, take it to bed Karen, there's a big day coming tomorrow.' Charles smirked.

A shiver ran down my body, the look on his face was scary. Karen got up came towards me and unclipped the chain, I started to rise, 'what are you doing slut? You stay on your knees' and with that she pulled on the chain leading me out the room. I struggled going fast enough behind her but she didn't ease up nearly dragging me up stairs. Once we got to the bedroom she unclipped the chain but not the collar 'That stays on' she said, you'll learn to sleep with it on, eventually'. Then the door was closed and I was on my own. I undressed, gently removed the butt plug, my hole was sore but getting better, put a lovely pink flowered pyjama shirt and shorts on and climbed in to bed. Sleep was difficult with the collar but I nodded off without to much discomfort. I wasn't sure how long I was asleep when suddenly the door banged open and the lights went on, I was disorinenated by the light and slowly my eyes adjusted, Charles stood in the doorway naked apart from an open robe around him, 'Ooohhh therrrreess me litttle whooore' H e slurred. He was clearly d*unk but I had know where to go. He approached the bed 'what the fuck are you waiting for?' he shouted 'on your fucking knees and open your mouth'. Fearful of what he might do to me in this condition I obliged. He wobbled d*unkenly and pushed his crotch towards me, his cock flaccid and limp, 'well, get me hard whore, I want to fuck you'. He roughly pushed his hand roughly down my top and started to tugged on my nipples, I dare not cry out in pain so I took his cock in my mouth slowly, closed my eyes, I could smell then taste the bitterness of piss but was determined not to retch, moving back and forwards trying to please him, I kept on sucking and licking, my hand playing with his balls. Then suddenly he smacked me hard across the face sending me falling to the floor.

'YOU STUPID WHORE YOUR NOT DOING IT RIGHT I NOT GETTING FUCKING HARD!' he dragged me up pushed me face first across the bed, next he ripped my shorts down, he started to get behind me then thrust a finger in my hole, the pain seared through me, another finger and another. 'think your ready for me now bitch' he pushed his still flaccid cock towards my hole but he wasn't just wasn't hard enough to enter. 'FOR FUCK SAKE' he cried out and suddenly punched me in the kidneys. I slide to the floor in agony and then he kicked in the stomach, I lay there gasping for air, winded and in pain.

'You best perform better tomorrow slag' he turned and stomped out the room slamming the door behind. I wasn't sure what hurt more at that moment still gasping for breath. After nearly an hour I gently moved still aching everywhere. I pulled myself up on to the bed pulled the covers me and cried myself to sleep, the lights still shining bright.

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By *ichellesubsissy OP TV/TS over a year ago

Further down the rabbit hole

I awoke to Karen gently touching my cheek, 'its time to get hun, you've a very special day ahead of you today' she gently said. I rose feeling stiff and a bit sore, 'oh lets help ease that pain a bit for you hun' and pulled a syringe from her pocket took the cover of the needle swabbed my arm and injected me. A warm soothing feeling suddenly over took me' 'that feels nice' I mumbled. 'oh just a little pain relief' she replied 'now shower and come back to in here to me'.

I stood up and feeling a bit floaty and dizzy but went along with what she had said. Showered, shaved and still feeling a little hazy I returned to the bedroom and sat at the dressing table, 'now just for today Charles has permitted the removal of your collar as where your going it won't be necessary, and again Karen started to apply my make up, brushed and styled my hair in I very loose ponytail. 'Ok, lets get you dressed hun'. I stood up and had me stand in to a black basque and black lacy shorts. She then made me sit and started to put on black seamed stockings on to my legs easing each one up and adjusting the seam straight. Then again made me stand and pulled out a black, knee length dress. Standing in it to each she pulled it up over my body an electric sensation over my skin from the fabric, slide my arms through and zipped up the back. Next came a pair of black court shoes. 'Hows that feel?' she asked. 'Fabulous' I replied dreamily. Never when I started dressing had I ever felt I could look and feel this feminine.

'Good' came her reply, 'your in for a very special day'. She the placed a black velvet necklace around my neck. I reached up and touched in gently it felt so soft a long way from the leather posture collar i'd had to wear.

'Today your in for a real treat' She smiled. My apprehension over what I thought would happen disappeared. She then took a black jacket off a hanger and put it around me. 'One last thing ' she said, 'need somewhere to keep your lipstick and passed me a little black clutch bag. 'Well I think your ready, come on' Karen said. We walked out the bedroom and down the stairs, my excitement of what this day would bring feeling me with joy. Charles stood in the hallway dressed in a dark suit and open necked shirt, 'Well you do look very appropriately dressed sissy' he said. He didn't mention of last nights little adventure and I definitely wasn't going to say anything with the euphoria I was feeling, thinking that we'd turned a corner and things were going to easer from here on. How wrong was I looking back.

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By *imale38Man over a year ago

Barnsley

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By *asey666Man over a year ago

Dublin 13

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By *atexpvcTV/TS over a year ago

chester/Merseyside

Fatastic story one that i would hope someone out there woukd like to do to me. Completly transform me and control me..

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By *isihartWoman over a year ago

Around

Ok this isnt something I am even interested in. But I am captivated and want to know more! I keep coming back seeing if there has been any update!

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By *es for funMan over a year ago

port talbot

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By *ersatile-1Man over a year ago

stirlingshire

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By *ony 529Man over a year ago

coventry

Mmmm loving every minute of this this certainly happens in my dreams but not in reality

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By *ichellesubsissy OP TV/TS over a year ago

Further down the rabbit hole

We stepped outside the front door, the first time I'd been outside the house since arriving, well apart from the night in the garage. Waiting near the front door a large car with a man stood holding the back door open. 'After you', Charles said. I stepped in slide over the leather back seat, in front of me was a drop down table, crystal glasses and decanters of dark brown liquids, also a dark screen preventing any view through to the front of the car and windscreen. Charles slide in close next to me and the back door closed, not long after I heard a door open and close and the engine start up. 'Master can I ask....' I started to say. 'Ssshh'. Charles replied 'just relax we're going for a little trip and a lesson. I think you might enjoy it, here have drink'. He took two glasses filled them band handed one to me. 'Bottoms up' he smirked as he raised a toast, we clinked glasses and I couldn't help but think we'd turned a corner.

We drove for about an hour, time seemed to pass by quickly, more drinks, Charles' hand on my knee, feeling more and more relaxed. Then Charles said 'Oh just one thing, I need you to wear this', and pulled a blindfold out. OK I thought this was adding to the mystery but I was to relaxed and enjoying myself too much to think any untoward might be happening. I turned in the seat and let him put the blindfold on. Turning back I felt his hand first on my then slide up my thigh before I realised it he was pushing his hand against my crotch. 'Oh your little sissy clit is twitching my dear, I like that'. I was getting aroused I had to admit. We drove on, me in complete darkness. Charles not saying anything next to me. This was a real thrill, I knew he was taking me somewhere special because of how we were both dressed. I felt the car do several turns and eventually slow and stop, the engine turned off and the front door open. Then as the back door opened Charles moved and I felt his breath on my neck, 'Everything that is about to happen you agreed to when you signed that bit of paper, remember that', he said with a cold edge to his voice, 'now please get out of the car, I will guide you until we get to our eventual destination'. With that he took hold of my hand got out of the car and guided me across the seat and out the car. It felt cold wherever we where. 'Now come with me sissy'. He gently guided me holding my hand and a hand round my waist. Stopping I heard him push some sort of button that sounded a bell, I heard a lock turn and a door open.

'Well fuck me Charlie you've out done yourself this time you old dog' a voice I'd never heard before said. 'Yeah you owe me big for this one', came a chuckled reply 'OK inside sissy', and he pushed me through the doorway. It was warming inside but not much. We walked down a corridor, I could heels clicking on the floor and the sound of at least three other people. Several doors then gates unlocked opened and then closed behind us. Where were we I thought, this really didn't feel right but what could I do I was still blindfolded, so on we walked. Then we entered a somewhere slightly warmer than where we had been and stopped.

'We're going to enjoy this one Charlie boy', he first voice I'd heard said. 'Fuck yeah Charles its happy time here today, thank you'. said another. I could only think there were at least two others here but who were they. Then I heard Charles say 'all I ask is that its still useable afterwards'. That brought laughter from them all. OK now I was starting to get worried,what was going on? Then all my questions and worries were answered as the blindfold was removed. I was I a bare room apart from a single dirty bed with a heavily stained mattress on two men in uniform I'd never seen before and Charles. 'well I'd best explain why your here sissy, this is Jimmy' he said pointing to one of the men, 'he's my little brother and to be honest a bit of a twat', 'Hey' shouted Jimmy 'no need for foul language in front of the lady. There'll be enough of that later'. Which brought laughter from everybody. 'Well' Charles continued 'he works here, lets say helping people, and I help him out from time to time and your one of those times.'

I looked at Jimmy, he looked like Charles but younger. Toned and tall, I'd say nice under other circumstances. 'I told you today would be special and your indiscretion would be punished, well here it is. I'm going to leave you with these two lets say gents and pick you later or possibly tomorrow , I'm unsure yet.' He then shook hands with Jimmy and they both walked out the door' I stood there with just the other man, he was looked about twenty three, big muscular body, shaved head and narrow little inset eyes giving him a real menacing, evil look. He looked me up and down and I could feel him undressing me with his eye a tight grim smile on his face, he licks his lips and I feel genuinely repulsed by it. Then the door opens and Jimmy comes in, 'ah I see you and Craig here are getting to know each other. He doesn't say much but there's none I'd rather be in here with. He can be a total animal when needed.'

'Now can I get you a drink or anything before we start?' Jimmy asks. 'Start what?' I reply. 'Oh your in for a real treat my dear. Charlie had told me a lot about you, now lets start off easy', and he comes close to me slips his hands round my waist and pulls me to him and starts to kiss me slowly then more and more passionately, his tongue probing my mouth his hands sliding down and gripping my arse, pulling my dress up, rubbing the tops of my stockings, I'm kissing my back, the more I kiss him the more passionately he kisses back I can feel his hands on my pantie clad arse, his cock is rock hard, pushing against me, oh want to feel it in my hand. My hand reaches down for it squeezing it through his pants. 'oh you are as good as Charlie said'. He whispers in my ear. He slides a hand up and feels starts to grope my small pert breast. 'I want you now' he says and suddenly turns me round and pushes me against the wall, forcing my hands and arms up, I can feel him start to bite my neck, his hands pushing my dress further up over my waist, his hand is inside my panties, 'Now what have we here' he says as he feels my little sissy clitty, I can feel it leaking pre cum, his hand rubbing it, then he brings it up to my mouth, 'lick it, I know you want to', I greedily lick and suck his fingers and hand tasting my own fluids, getting me more and more horny, oblivious of anyone else in the room. He takes his wet fingers and pulls my panties aside and starts to rub my hole, I want him in me so much, this is the most gentlest it had been since I arrived at Charles' house. He undid his pants and I sense them fall to the floor, his hand came back to my mouth and I lick and suck his fingers again, then I feel his hand rub his cock and the tip touch my hole, I feels big, I can't wait to have it inside so I push back trying to get it in. 'You are a very naughty gurl,' Jimmy says, and with one forward thrust he's inside me. He is long and thick, I can feel it filling all my hole and touching my prostate. He starts to ease out and in slowly all the time rubbing my g spot. I am in heaven he's so big but gentle. He takes hold of my hips and goes deeper, he starts talking to me but I'm in too much ecstasy to listen properly.

'We are part of team here, there are four of us, working alternate shifts. You'll meet the others at some point' he says. 'OK' I utter, too lost in the feeling of being fucked, pre cum dripping out. Getting closer to reaching a climax. He tells me 'they are going to enjoy you and you will please them all'. 'Mmmmm' I whisper as I bite my lip, 'oh yes I'm coming' I start to say, he just keeps fucking me so gentle. 'Eat it' he says. My hand goes straight down and I try to catch all of it but there is so much, my hand is dripping I greedily start to lick and eat my own cum, I've always loved to eat it but there's just so much and its still coming out. 'What do you think Craig?' Jimmy asks, I'd forgot the other menacing one was still here, I opened my eyes and turn to look and find him stood close to me just looking at me with a leering smile on his face. Then I felt Jimmy's cock twitch and hot cum shoot up my arse, hitting the very deepest parts of my hole. He pulls his cock out and the warm sticky feeling as it runs out. Pulling my panties up to stop it going everywhere. Jimmy has his pants up and fastening his belt, 'Yes they are going to love you' he repeats. Then I start to remember what he was telling me, 'Whats going to happen?' I ask. 'Oh you'll find out soon enough', he replies, 'Come on Craig lets get he first one in', Craig takes one last leering evil smile at me and they both leave the room.

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