Chloe's Contract Read online

  He stretched his neck towards her crotch, and was rewarded with a movement towards him that enabled him to nuzzle into her mound and feel the responding pressure from her sex. But then she moved away quickly to perform a detailed examination of his stretched back passage. The point of her cane was inserted into the opened entrance forced into being by the speculum. She tapped the inner lining of steel that was pressing against his anal tube, and finally prodded his knob as the tip of the cane probed between the speculum’s open leaves at his sphincter’s end and pressed against his cock. He winced, but curiously it was not a reaction to pain but an acknowledgement of her right to possess him in this way. She sensed his acceptance of her right to do with him as she pleased, and she kissed the still reddened cheeks of his bottom with an unaccustomed tenderness.

  ‘Chloe has done well, Sophie. This is a very good start. I can see she will soon be able to manipulate those muscles in a way that will be both useful and sensuous. Has she had her daily exercise yet?’

  ‘No, Mistress,’ Sophie replied, ‘but she can do those at any time, surely?’

  ‘No, Sophie, I have explained before. Physical exercise is essential. Our girls must be fit as well as talented. They must have stamina as well as skill. The treadmill - now,’ she commanded.

  ‘Yes, Mistress.’

  ‘And then some sucking therapy. Those lips and mouth have potential, but we’ll not thoroughly appreciate them unless we are sure she’s been tested against the very best.’

  ‘Yes, Mistress,’ Sophie replied again.

  ‘But this is good start; she must be almost an inch and a half in diameter here, the maximum for the A-size.’

  ‘An inch and five eighths, actually, Mistress,’ Sophie informed proudly. ‘I’ve taken careful measurements.’

  ‘I don’t care to personally verify your assertion, but I am prepared to accept it. The important thing now is to ensure that she can take the C-size.’

  ‘I’m sure she’ll be able to in a few days, Mistress.’

  ‘Make sure she can. Now work on her mouth until our clients arrive.’

  ‘Are they coming together?’ whispered Sophie.

  ‘No, they have to arrive separately because although Diane knows Martha will be here, Martha does not yet realise what’s in store for her from Diane. But both are ready for what we have in mind, and what we know they need. We can cope between us, and they pay well. If all goes well they might even be able to afford the Abbey for future meetings. I might suggest it if this afternoon’s games work out but are not satisfying enough for them.’

  ‘What do you want me to do?’

  ‘I think the scenario is pretty much as we have discussed with each of them separately. It’s an unusual situation, certainly, but each has discovered through our treatment of them what they want, and I am more than happy to satisfy that need. What you have to remember is that it’s not so much of a coincidence as you might imagine. The very fact that Martha employed Diane in the first place is indicative of her subconscious desire. She would have sensed she was what she wanted and, as we know, being a professional, real life high-flyer often means a sexual need that is the opposite of what you might expect. Now, this is really your first big part, so are you ready for it?’

  ‘I am a bit frightened, if I’m honest, Mistress,’ Sophie admitted. ‘But if you think I can do it then I’m sure I can.’

  ‘Oh, I am sure you can. It will be painful - but not as painful as my punishment should you fail. And no holding back so you can suffer at my hands; I will know if you’re not putting everything into it,’ she warned.

  Sophie bowed her head in acknowledgement of the warning. She had no intention of holding back because she really wanted to prove that she was good enough to take the place allocated to her at the Abbey.

  ‘Chloe had better do some physical exercises in the gym now.’ He had been ignored as she and Sophie talked, but now her attention returned to him. ‘My slaves have to be very fit,’ she told him, and then to Sophie she said, ‘When you put Chloe away show her what she needs to do to begin her suction training. And that’s probably enough of the speculum for now. She’ll probably need a few more days with the A-size.

  ‘Martha and Diane are due at two, so we can have a light lunch and go through the details of this afternoon’s performance as soon as Chloe’s finished her session on the treadmill.’

  She left the room and Sophie began to reverse the turns on the grip of the speculum. His aching muscles were gradually released from the extension, and he sobbed with relief as it finally slid from his anus.

  ‘Thank you, Mistress,’ he sighed, and Sophie gave him two stinging spanks.

  ‘Careful, Chloe. I am not your Mistress. Like you I’m a student. The only difference is that I’m close to graduation and you’re in your first term and have a great deal to learn. We are both submissives, totally dedicated to our Mistress, who looks after us and cares for us. I am trusted to carry out her orders, which is what I am doing if I humiliate or punish you, because I have agreed my contract with her - as I’m sure you will when the time comes for you to make your choice.’

  She released his wrists from the links holding him down and he peeled himself stiffly back from the horse, his cock rasping against its surface as she attended to his ankles. He could stand straight, but was barely able to put one foot in front of the other as his stiff muscles protested at every small effort.

  ‘We have to get you back to normal quickly,’ she said. ‘I have another exercise for you before you’re put away for the afternoon, and you must keep yourself fit.’

  Still naked, his cock as hard as ever, he was taken to a small but well equipped gym. It contained a selection of sophisticated computerised exercise machines, all of which had been modified to ensure that those using them could be restrained if necessary. There was a large plasma television screen built into one corner so it could be easily seen by anyone using the room. An explicit DVD was playing, the quality of the filming extremely high, the sharp definition of the close ups and the actual content quite beyond anything he had watched before. He did a double take as a change of shot revealed that the blonde on screen was Sophie. She was standing behind a crouched body wearing a waist gripping suspender belt, black stockings and high heels. His bottom was red raw from a previous beating, and as the camera zoomed in it was clear that there were even dark bruises on the weighty balls that hung between his legs. Sophie herself was naked and wearing an enormous strap-on. It must have been almost three inches in diameter and stuck out long and solid from her crotch. As the camera zoomed back it revealed part of another woman, Mistress, he thought, wielding a fine cane that from the marks on Sophie’s bottom had already been used to very good effect. It came down again as he watched, forcing her to bring the phallus up against the tight ring of the sissy’s anus. He breathed deeply and his anal ring relaxed and opened as the monstrous penis breached it with only the slightest stretching required.

  Sophie switched off the screen. ‘You can watch that later. But I hope you noticed that Audrey was not restrained and neither was I. Part of the pleasure is certainly the agony of being held down, but there comes a point where the humiliation is so much a part of the relationship that restraint can sometimes be a distraction and kept for special occasions only.’

  Sophie helped him get onto the treadmill, and as he placed his hands on the support bar she wrapped velcro straps around his wrists.

  ‘Twenty minutes should be enough,’ she said. ‘I’ll set it slow to begin with, and it’ll speed up automatically to four miles an hour. Then we can tilt it so you’re going uphill. This is really to stretch you a bit. Most days you’ll spend several hours in here, improving your muscle tone and losing some of that surplus weight. There’s not much, but you’ll look a lot better when dressed as a female if you can slim those thighs and that tummy down a bit. And the hormone therapies will ensure that any surp
lus moves to your bottom and your breasts, so I think you’ll look very good.’

  He wanted more information about the hormones, but decided to return to an earlier topic while Sophie was in a chatty mood. ‘When did you sign your contract?’ he asked.

  ‘Quite soon after I first came here,’ she told him. ‘Mistress spotted me in a bar in town. A group of us worked in a department store and were having a drink together. I sold cosmetics and my boyfriend and his friends worked in the warehouse. It was early evening and quite quiet, and my boyfriend, Matt, was showing me off to his mates. He was a super looking guy. I hadn’t been with him long and I didn’t want to lose him, but he obviously knew that and knew I’d do whatever he wanted. He liked me to wear high heels, short skirts, skimpy tops and no bra, just to show off how well he controlled me. I hated the way he treated me.’ She paused for a moment and considered what she’d said.

  ‘No, that’s not right, because deep down I wanted to be controlled and used. But then I realised I wanted to be controlled and used by someone who appreciated me. And he didn’t, and most of the men I’ve known didn’t either. They just saw me as a good fuck who liked it hard, rough and painful. It suited their masculinity, I suppose, and I did go with men who wanted just that. But Mistress loved me too and has introduced me to clients who respect me as well as dominate me. There’s a difference.’

  The treadmill was beginning to speed up. ‘So what happened?’ Chloe asked, beginning to pant a little heavily.

  ‘I think she must have been watching me for some time. She was in one of her smart business suits; power dressing stuff, if you know what I mean. Black pinstripe, I remember, with a white blouse, glistening stockings and those wonderful high heels. She just walked over and said, “Can I join you?”, and of course Matt and his friends really didn’t know what to do. She was so obviously out of their league.

  ‘She was wonderful. She asked me my name, and as I told her she reached between Matt’s legs and gave his balls such a squeeze that he yelped out loud. She pulled him off the chair and just twisted so until he collapsed on the floor. Then she just said, “You had better come with me. You’re obviously not appreciated here”. So I got up and left with her, and that was it.

  ‘She introduced me to Audrey - you’ll meet her later - who was her servant at the time, arranged for me to be constructively dismissed from my job so I had some money, rearranged the lease of my flat in a way that gave me some more, and brought me to live with her here. I don’t know how she does it but she has so many influential friends and clients she seems to be able to organise absolutely anything.’

  She moved a graduated lever on the treadmill and it began to slow down. ‘That’s probably enough for the first time,’ she decided.

  ‘She gave me the same choice as you. You have one chance to leave, although actually I think you could go at any time you wanted to until the contract is offered. But if you accept it you have to stay as long as she wants you too. Not here, though. At the Abbey.’

  The treadmill stopped and he got off thankfully. ‘So I could leave now?’ he asked.

  ‘Yes, I only restrain you because you’re in training and want to be abused. But for the moment you are, in effect, free to go. I don’t advise it. Mistress is never wrong and if she thinks you’re suited for this life I’m sure you are.’

  ‘And what about the hormones?’ He was somewhat unsettled by the prospect of taking them.

  ‘You won’t begin hormone treatment until you’ve agreed the contract,’ she told him. ‘They just emphasise your femininity without affecting your masculinity. Don’t worry; Mistress wants to sissify you, not turn you into a female. Your masculinity is important; in fact it’s an essential part of your submissive personality. Most women, whatever they say to the contrary, want to be controlled, and although some are dominant most are submissive, and many actually want to be humiliated. Many men are submissive underneath too, but they don’t want to be female. Like you.’

  ‘And the Abbey?’

  ‘The Abbey is Mistress Amanda’s country establishment. It’s part hospital where full, physical makeovers can be carried out—’

  ‘Makeovers?’ he interrupted.

  ‘That’s total change from male to female, or vice-versa.’

  She resumed her thread. ‘Part hotel and part... I’m not sure how best to describe its special features,’ she mused, ‘but those who go there have special needs and desires and the money to indulge them.’

  She glanced at a clock on the wall and said, ‘I must get on. Come along and I’ll introduce you to the next exercise.’

  They returned to the training room and Sophie took something from the fridge. As the door was closing he spied the bottle of his piss still on a shelf, and wondered what it was to be used for.

  ‘This is uncooked asparagus,’ she told him unnecessarily, holding up what she’d retrieved from the fridge. ‘I’m going to hang six sticks in your cell so you can just reach them from your sitting position on the floor. You’re to take the tip into your mouth and by sucking only, strip the layers off so that it becomes as thin as a pencil. Like this...’ she put one asparagus stem into her mouth, sucked tightly and gradually pulled it out, removing the outer surface completely. She pulled his hand to her lips and spat the vegetable skin into his palm. ‘Like that.’

  He looked at the stem. The outer skin had been removed evenly all the way down and there were no teeth marks. ‘Try it, but you must use only your lips. I’ll know if you’ve tried to use your teeth.’

  She gave him a fresh piece, and to get his lips to the point that Sophie had he had to push the tip into his throat, and he almost choked and had to stop, cough and begin again.

  ‘Take it down gently,’ she coaxed. ‘You’ll be able to take ten inches eventually, and it’ll seem so natural you won’t notice it.’

  He tried again. This time he was able to keep his lips tight around it, and as he dragged it out he realised just how coarse asparagus was. The hard bumps scraped the inside of his mouth and tore at the soft tissue.

  ‘Let’s see how much you’ve got,’ she said.

  There wasn’t much. ‘Don’t worry, everyone finds this hard to begin with, but I promise you it’s worth it. Think how well you’ll able to pleasure Mistress when you can do it as well as I do. And if you can take a stick down to pencil diameter in ten strokes, she might let you have a very special treat. She needs to come too, remember, but only on her terms. Now, into your cell.’

  He sat down in what he was beginning to think of as his usual position on the floor, and she strapped him down before hanging the asparagus stems from hooks so he could just reach up to take them into his mouth. The door closed and he was left in darkness.

  He heard her heels click away and leaned forward to begin work on the first stem. It was hard, but he desperately wanted to achieve a standard that would please his Mistress, so again and again he sucked at the first stick, and there was no doubt that after a few minutes the outer surface softened and began to break up. He might be able to manage it. He wondered how long the afternoon’s booked session was. And what was in store for him that evening.

  Chapter Ten

  Diane arrived first. She was slim, red-haired and beautifully groomed. Her sweet, heart-shaped face and hazel eyes gave no hint of the turmoil that was wrenching her mind and her body as she stood at the door and hesitantly pressed the bell. She was smartly dressed for the office, in slacks and a fine wool sweater that showed that her breasts were ample and well shaped. A simple thigh length jacket and neat shoes with heels, although not high, emphasised her femininity for any office environment. She carried a small Gucci overnight bag. As Mistress opened the door, dressed only in a long silk gown, her immediate impression, as it always was when Diane came to her, was one of real style and class. Mistress held out her hand and drew her in, kissing her lightly on the cheek.

  ‘Hello, Dian
e, come in. How are you today?’

  Diane smiled. ‘A little nervous, I confess,’ she admitted, ‘but I know with you looking after things it will be OK.’

  ‘I’m sure it will. Come along to my room and I’ll help you change. Sophie can let Martha in when she arrives. She has her instructions. Your boss will have a shock, even though she’s expecting a surprise.’

  ‘Does she know her new Mistress will be me?’ asked Diane.

  ‘Of course not. And she’ll never know unless you and I agree it will be in the best interests of you both. If she feels about you the way you feel about her then it might work very well. We’ll have to see.’

  They went together into Mistress’s lovely bedroom.

  ‘I have other premises that might have been more suitable for today. These are rather more cramped, I’m afraid, so I’m not able to give you both a private room in which to get ready. Although,’ she smiled, ‘I am looking forward to helping you change.’

  As she looked at Diane she noted her evident interest in the other premises. ‘Do you have somewhere else?’ she asked, casually.

  ‘Oh, yes,’ Mistress replied. ‘It has every facility imaginable, but I’m afraid it is rather expensive. But Martha could afford it, I should think; owning her own company as she does.’

  ‘Yes, and she’s been very successful. Recruitment companies, especially in computing, seem to be doing very well. I know I’m just her PA but she pays me very well. There are twelve consultants as well as the support staff like me, and she has a lovely house here and a place in the south of France - and the Porsche, of course.’

  ‘Of course,’ Mistress mused. ‘But like so many other achievers, underneath she longs for release from the pressures and yearns to become completely subservient. Which is why she came to me.’