Chloe's Contract

by David James

  She held the spur and revealed its pair in the other hand. Kneeling again she drew his prepuce back and placed the two discs at the root of his cock, one on each side. Even their lightest touch was agony. She pressed them in towards the centre and ran them up each side of his stalk and across the helmet. A burning pain lanced through his bowels and he jerked, puppet-like, until she took his cock deep into her throat and bathed it with saliva. A warm glow of pain followed by relief flowed through him.

  ‘Again?’ she asked.

  He did not think he could take that level of pain again, but could not help but nod his head.

  ‘Mistress will be pleased,’ she whispered.

  The needle-tipped discs dug into the base of his rigid rod once again. This time she held them in place and he felt quite clearly three spikes pierce the soft skin on each side of his cock. Then, still pressing, they sliced upwards, leaving a parallel trail of raised burrs. He could not think for the pain; it rushed through his stomach and his skull, enveloping him in a thick red mist from which he was only rescued by the sensation of his cock slipping back deep into her throat.

  She caressed him gently with her mouth for several minutes and then slid away, allowing the coolness of the air to flow round him, an added balm.

  ‘Twice is enough,’ she said. ‘For now.’ She replaced the spurs on the shelf and returned.

  ‘A good start, Chloe,’ she confided. ‘None of my former pupils could take two tracks of the needle discs so soon in their training. I think you are going to stay.

  ‘But now I have to help Mistress. I will leave you here, but I’ll make you more comfortable first.’

  As good as her word she unbound his ankles so that he could again stand upright. Then she took off the wristbands and replaced them with the handcuffs. He wondered whether this was an opportunity to leave, but even if he wanted to - and he didn’t - his aching muscles would not have allowed him to move very quickly. And he was still in the high-heeled shoes and virtually naked into the bargain.

  Sophie led him to a suede-topped vaulting horse and bent him over it. His manacled wrists were hooked into rings at the base on the far side and a triangular piece of wood was placed between his thighs, forcing his legs and the cheeks of his bottom wide apart. The familiar velcro bands restrained him at each ankle.

  ‘I won’t be long,’ Sophie said as she left him, still gagged, and as a result of his position, able to see little more than when he was blindfolded.

  For the first time since had arrived at the apartment he had time to think. It was not easy, as his solid cock was pressed into the suede of the vaulting horse, with his weight immovable upon it. It was beginning to recover but the deep ache of his balls, filled with spunk as they were from the extended length of time he had been rigid with excitement, were aching almost beyond endurance. He had no idea what the time was. His appointment had been for three o’clock so it must be at least the middle or even late evening by now. His depilation and make-up alone must have taken a couple of hours, and he realised that even if he chose to leave he would not be able to return to work for some time. No one would know about the absence of body hair, but his eyebrows and the urchin cut of his hair would take a while to get back to normal. He could be ill for a couple of weeks, he supposed, so that most of the changes would be repaired, but the more he thought about the 24/7 proposal of Mistress Amanda the more he was positively intrigued by the thought of giving himself up entirely to her needs and wishes, and to the training given by Sophie.

  He loved the idea of suffering for her, and he had nothing to keep him in the ‘real’ world. So why not? she had assured him of another opportunity to walk away some time in the future and, unaccountably, despite the pain and humiliation she promised - no, because of it - he wanted to follow his instincts. And his instincts were to do exactly as Mistress Amanda demanded. But there were more tests and training to come, and how would he feel when he was finally given the choice; accept the contract or walk away?

  And what was the difference in clientele between the expensive and obviously extensive apartment in which he found himself, and the Abbey? There were still so many questions but, with his cock erect and digging into his stomach, he knew he would find out because there was little doubt he would accept the ‘position’ offered to him.

  The door opened, and he sensed not only that Sophie had returned, but that she was not alone.

  ‘How did Chloe take the spurs?’ she demanded.

  ‘Very well, Mistress,’ Sophie replied. ‘Twice.’ He could feel the pride in her voice.

  ‘Well done, Little One.’ Mistress’s voice was both calm and affectionate, but it did not remain so for long. She strode over to the vaulting horse to inspect her latest recruit, and he heard the click of her high heels on the bare floorboards.

  ‘Sophie!’ she barked angrily. ‘She’s unplugged. How could you have left her restrained with an empty anus? Fill her immediately!’

  ‘Yes, Mistress,’ Sophie replied, real fear in her voice. She had obviously been so pleased with Chloe’s progress that she’d quite forgotten her own responsibilities. She clicked across the room and he heard a cupboard door being opened and shut.

  ‘Show her first,’ Mistress ordered.

  Sophie moved in front of him so he could see the blonde bush neatly trimmed around her mound, just in front of him as he lifted his head. She cradled a nine inch black plastic dildo in her small hands, one at the base and one reverently sliding across the thick shaft. She crouched down and smiled at him, her eyes glittering excitedly in dual anticipation, first of sliding the dildo into the depths of his arse, and the punishment she knew she was to receive from her Mistress.

  ‘No lubrication, Sophie,’ Mistress instructed. ‘But we can both contribute a little saliva to ease its passage. It will be tight even though she took one of my medium dildos last week. This will stretch her severely, but she will manage it.’

  She moved around the horse to join Sophie, took the dildo and slid it deep into her mouth in front of him. He felt his cock spasm. She handed it back to Sophie.

  ‘You know what to do, and what will happen after,’ she smiled wickedly.

  ‘Yes, Mistress.’ Sophie added her saliva to the plastic penis that now glistened with their combined spit, and moved out of his vision.

  ‘None too gentle, mind,’ smiled Mistress, her eyes glinting in anticipation. ‘I’ll watch Chloe’s discomfort from here, and the greater it is the less your own punishment.’

  He felt the cheeks of his bottom being parted and one of Sophie’s fingers easing open the tight pucker of his anal ring. Then the knob being placed and twisted against him, and the muscles being put under pressure. He felt her change her grip as she prepared to thrust deep inside him, and he clenched his buttocks in anticipation. The dildo was pushed back for a moment and he realised it would be even more painful if he did not relax, so he endeavoured to and felt the knob slip back into the right position.

  Sophie twisted hard and forced the dildo into him to the hilt, in one strong and powerful movement. The sudden pain was agonising and his body writhed on the horse, his bowel stretched and throbbing. The pain was so great that he sensed rather than felt the medical tape being applied cross his bottom to keep the dildo embedded deep inside him. He groaned through his gag and Mistress kissed him lightly on the forehead as she rose, giving him a tantalising glimpse of her creamy thighs above the tops of her stockings, and the neat triangle of leather now masking her desirable black bush and slit.

  ‘Good, Sophie, but not good enough to escape punishment,’ she murmured. ‘Strip off and climb on top of Chloe.’

  A few moments later he felt Sophie lift herself onto the horse and lay over his back, so that his head was between her thighs and her hands gripped his calves, her flushed cheek resting on his bottom. She was small and light but the extra weight on him immediately brought back the pain of his
cock being ground into the horse.

  ‘The cat, I think,’ Mistress mused as she stepped over to one of the racks.

  ‘How many lashes do you think your forgetfulness deserves?’ she asked mildly, in a tone that would not have been out of place at a tea party when sugar was being offered.

  ‘Six, Mistress?’ Sophie replied, a tremor clearly audible in her reply.

  ‘My estimate, exactly,’ Mistress agreed.

  Sophie was excited by the prospect. He knew because she had only been settled on his back for a few moments when he felt a slick of juice trickling onto his neck from her sex. She wriggled and he could feel the heat emanating from between her legs as she tensed in anticipation of the first snap of the lash. It was not long in coming. He heard the tails of the cat scatter on the bare boards as Mistress flicked them over her shoulder in preparation for the longest curve of momentum she could manage. Then the hiss of the fine leather filaments as the lash whipped through the air and wrapped each cord around Sophie’s vulnerable bottom. They snapped around her, some flicking and nicking his face as they reached the end of the arc. She knew better than to scream but he felt her body go rigid on him, as the cat was drawn harshly back across the globes, the coarse threads dragging across the weals that he knew must have been raised.

  Then the second slash, the fine ends whipping around her and biting into his right cheek. Sophie gave a low moan and he writhed once more, painfully crushing his cock. He could not believe he was still so solid, and the thought of Sophie’s next cut seemed to increase its girth. The leather bit again into Sophie’s bottom, harder this time, he knew, because not only did she give a strangled scream but also the tips of the lash actually drew blood from his cheek. He thrashed about to the extent that Mistress stopped to look at him. She saw the damage immediately and smiled.

  ‘We had better balance that off,’ she mused, and moved to the other side of the horse.

  Crack! Once again the lash slammed into the soft flesh of bottom and cheek, and then twice more, by which time Sophie, although streaming juices from her sex, was sobbing.

  ‘You can get off now,’ Mistress commanded, and Sophie slid down from his back, the creamy juices that saturated the tops of her thighs and pubic curls being transferred into his hair, leaving it sticky and matted.

  She bobbed a curtsey, wincing slightly. ‘Thank you, Mistress.’

  She turned her bottom proudly towards him so that he could appreciate the swollen grooves that marked her buttocks and ran around to her hips. She moved back towards him and he painfully lifted his head as she bent over and pressed her radiating globes into his face. He felt the heat and the deep scores brushing his own whip-bitten cheeks as she ground her anus against his nose and lips.

  ‘That’s enough,’ Mistress commanded. ‘Take Chloe off the horse and strap her to the throne. We have a client waiting and we may need her.’

  Sophie took the restraints off his ankles and wrists and helped him up. He could hardly stand after the privations of the last few hours, and he was still wearing the high heels. Sophie then adjusted the elastic of his knickers so that it was still tacked behind his balls, taking his aching erection into her hands, still surprisingly cool after her ordeal, before she sat him down on a wooden, high-backed chair. He felt the dildo bury itself more deeply into his rectum as his cheeks spread on the seat and his weight forced it further inside.

  The ankle and wrist restraints were put in place again, and he was almost comfortable for a moment until she took a wide black fabric collar, wrapped it around his throat and tied it behind the chair, taking the cloth through two holes in the back. A wide black leather belt was placed similarly around his waist, and adjusted so the top edge just brushed the raw and bloated tip of his cock.

  ‘You can take out the gag if Chloe promises to make no sound - whatever happens,’ Mistress said.

  Sophie leaned to him. ‘Do you promise?’ she asked, and he nodded. ‘Mistress means what she says,’ she warned him. ‘When she says “whatever happens”, it could really mean anything. She usually has something in mind that might make you want to speak... or scream... or beg. You do understand, don’t you?’

  He nodded again.

  ‘Stop chattering, Sophie,’ Mistress snapped. ‘Do you want more of the cat?’

  ‘Oh no, Mistress. I was just making sure Chloe understands that you mean exactly what you say.’

  ‘I am sure Chloe knows I mean exactly what I say, don’t you, Chloe?’

  He almost answered, but Sophie pressed her knee against his and he remembered just in time, and nodded instead.

  ‘Be careful, Sophie,’ Mistress warned. ‘I saw you remind her. You’re supposed to train Chloe, not help her avoid my punishments.

  ‘Now come along. I don’t mind her waiting but it’s been long enough.’

  Sophie left his side and trotted across the room, opening the door for her Mistress and closing it behind them as they left the dungeon.

  As far as he was able he relaxed and let the tension drain from his body. And now, at last, despite the deep ache in his balls, his cock began to lose some of its rigidity. He began to let go.

  Chapter Seven

  Strapped and restrained in the chair he almost fell asleep, but he was rudely brought back to reality when Sophie opened the door and entered with a man fully dressed and fitted with a collar and chain. He came willingly, not dragged or commanded. He seemed vaguely familiar, and he remembered that he’d had the same impression the previous week when he saw him walking towards the apartment as he went to his car. He still could not place him, though. He wore a conservative grey suit, and he showed no surprise on entering a room in which a near-naked man in five-inch high-heeled shoes was strapped to a wooden chair, that more than anything else resembled a medieval throne. His now flaccid cock was of no interest to the visitor, whose eyes were fixated on Sophie and particularly on her pert, thrusting breasts under her black silk top.

  Sophie led the man across the room and stood in front of him.

  ‘Chloe, this is Charlene,’ she introduced them. ‘Mistress is fed up and bored with him and says that you can have him and do what you like with him.’

  He was stunned. What sort of training was this, he wondered? Then, when the implications of her statement sunk in he was almost sick. What did he want with what looked like an ageing banker?

  Sophie went on. ‘Charlene has the biggest cock Mistress has ever seen, but he can’t get it up so she’s not interested.’

  Charlene blushed and then, as if suddenly realising the extent of the humiliation, cowered, his face turning a deep blotchy red with embarrassment.

  Sophie placed the chain in Chloe’s restrained hand. ‘Mistress says he’s so frightened of her that he’ll not cause you any trouble. But she wants him returned as someone who’ll be useful to her.’

  As she walked from the room she turned and smiled at him. ‘Mistress said to tell you it’s an order. This is one of the tests. She wants him back useful or interesting.’

  The door closed and he heard the key turn in the heavy lock.

  His first thought was that the task was impossible. His second was that Charlene might offer a means of escape. He was fairly sure that he did not want to leave, but he was also sure that for the moment he wanted to keep his options open.

  The key rattled in the lock again. It was Sophie. ‘Remember, you’re not allowed to make a sound; Mistress Amanda will know if you do.’ She closed the door and the key grated in the lock again.

  He looked around the room for inspiration, but none was forthcoming. If he could simply beat Charlene into being useful there were plenty of implements to hand, but he felt instinctively that this was not what was required. And he could not overcome the nagging feeling that he recognised the man.

  He tugged at the lead and nodded towards his wrist restraints, indicating that he wanted to be released.
Charlene looked askance, but after a few moments realised what he wanted and tore off the velcro restraints, unlocked his ankles and released the knot at the back of the chair so that at last he could stand and move normally - as far as he was able, given the stiffness in his joints, the dildo plugging his anal tract and the high-heeled shoes. He lifted the elastic of the knickers from under his balls and eased them down so he could strip the tape from his bottom and eject the phallus, which he dropped into a basin in one corner of the room. He then took off the high-heeled shoes, surprised to find that he was now almost more uncomfortable without them than he had been when wearing them.

  He examined his cock. After the battering it had taken he was surprised to see it looked quite normal, although there was certainly a tinge of redness to it, even though it was now quite calm and flaccid.

  Charlene would have been a handsome man once, with that haughty public school look beloved by the civil service and the city, even though they were distrusted by virtually everyone else. He tried to ask him why he had come to see Mistress, but as he was sworn to silence Charlene was unable to understand. He needed a pen and something to write on. He reached inside Charlene’s jacket and found a fountain pen and his chequebook.

  Why have you come here? he wrote.

  ‘I don’t know,’ Charlene replied, miserably. ‘My wife has told me that she’ll leave me if I don’t make ‘an effort’. I’d like to fuck her but I just can’t do it. I saw an advert in the paper and came last week to see her - just to get some ideas, I suppose.’

  And? Chloe wrote, and then added, I am not allowed to speak.

  ‘She gave me a thrashing and told me to come back again in a week’s time, so here I am.’

  Did you enjoy it?

  Charlene shook his head. ‘No. I didn’t see the point.’