Chloe's Contract

by David James

  So why did you come back?

  ‘I wanted to see if there was anything else I could learn. I don’t think there is. I get no pleasure being tied up or hit. I’ve been to several escorts, but nothing has helped.’

  Get undressed, Chloe wrote.

  ‘I guessed I’d have to,’ he said uncertainly, but began to undress anyway. ‘I love my wife but I just can’t do it any more. Someone suggested Viagra, but my doctor says I have a minor blood condition that means I can’t take them. My wife wants excitement and I can’t provide it. I think she’ll go to someone else. I fear she already has someone in mind.’

  Naked, he was not a bad looking man. Almost six feet tall with distinguished, greying hair, he had a strong face, blue eyes, slim build and a cock, although flaccid, almost eight inches long. His flesh was pale but he obviously kept fit.

  Chloe was still not sure that he wanted anything to do with this, but the incredible urge to please his mistress had him desperately trying to think how to turn the man on.

  Do you find the blonde girl attractive? he scrawled nervously.

  ‘Yes,’ Charlene replied, ‘but she doesn’t make me hard either. Nothing does.’

  When did you last have sex? he wrote.

  ‘I really can’t remember.’

  Chloe turned to the back cover of the chequebook, looking for more space, and as he did he caught sight on one of the cheques the name below the line reserved for the signature. He recognised it immediately and remembered where he had seen Charlene before. Some months previously he had been at a business lunch in a restaurant near his office, when his departmental accounts clerks had come in accompanied by the man that he now realised was her husband. He had been busy with two clients and they’d moved to the other end of the restaurant, so it would not be surprising if they had not seen him.

  Who do you think your wife might go with? he asked.

  ‘Oh, her boss, where she works. He’s younger than her and I’ve never met him, but I know she finds him attractive by the way she talks about him.’

  He had not realised. He’d noticed that Barbara had smartened herself up since he and Anne had parted, but he had been too slow to realise that she’d been trying to attract him. Now it made sense. He had even, quite casually, fantasised about her. In her early fifties she was still an attractive woman, with beautiful blonde hair, high cheekbones and full, kissable lips. She had large breasts, as he liked, and broad hips, promising the juicy labia and the musky scents that he remembered from his teenage experience with Joan. She had taken to coming close to him recently, not quite brushing her breasts against him, but close to it, and holding her face close to his while she explained the complications of some invoice or other. He had known instinctively that had he placed his hand on her bottom, hip or thigh, it would not have been either rejected or removed, but he’d not had the courage to make a move.

  He went to the door and knocked loudly. He desperately wanted to prove himself to Mistress, and he had an idea. A few moments later Sophie cautiously unlocked the door.

  He wrote, Please ask Mistress to give me permission to talk.

  She nodded, then closed and locked the door again, returning a few moments later. ‘Yes, you have it,’ she reported.

  He heaved a sigh of relief and turned to Charlene. ‘Where is Barbara now?’ he asked.

  ‘At home...’ He stopped. ‘How do you know her name?’

  ‘Never mind.’ He turned to Sophie. ‘Get dressed and go to the flat above that new boutique in the High Street. It’s not far. Tell the lady her husband needs her and bring her back here.’

  Sophie hesitated. ‘Go now. Ask Mistress’ permission, but get her here as quickly as you can. Her name is Barbara.’

  He realised that he was taking a huge risk. He would be burning his boats entirely taking this course of action, but suddenly he had realised that this was really what he wanted to do - to help Mistress Amanda do whatever she wanted. She had set him a task, and he wanted to succeed in it.

  He turned back to Charlene. ‘Back against the wall,’ he commanded, snapping the lead down sharply, wrenching the collar painfully around his neck. Charlene shuffled backwards until his naked back was pressed against the bricks. Chloe looked around for the restraints and ordered Charlene to spread his legs. He did so and his cock hung obscenely between his thighs, resting against the heavy sac of his balls.

  ‘Hands above your head,’ Chloe commanded, and bound the wrists of his captive tightly to two rings spaced about a foot apart. He saw that there were two more rings on either side at about waist height, so he lashed Charlene to them so that his bottom and back were held uncomfortably against the rough brickwork. He stood back to admire his handiwork. His pain, his discomfort and his humiliation at the hands of his Mistress and Sophie had miraculously faded away, and although his cheeks and his now solid cock ached and still showed the harsh evidence of their treatment by whip and spur, and his hair was still slicked down and musky with Sophie’s secretions, he was beginning to feel confident in the role allocated to him by his worshipped Mistress.

  Suddenly he realised that for his plan to succeed there were further preparations to be made. He opened one of the cupboards and immediately found what he needed; a black robe with a cowl that would mask his face. He put it on. He also brought out a range of paddles, whips and leather straps that he arranged carefully on the vaulting horse. He picked up a cane and flicked the sharp end against the underside of Charlene’s cock, lifting its heavy length before allowing it to drop back down, soft and useless.

  The door opened and Mistress Amanda appeared, eyes smouldering. ‘Chloe?’ she said cautiously. ‘What are you up to?’

  ‘Following your desires, Mistress,’ he replied.

  ‘Then why are you not on your knees?’ she asked, and he dropped immediately to the floor, his head bowed. ‘And trainees must always be in uniform. Now put your shoes back on. If you succeed I may allow you suspenders and a pair of stockings and thrash you less hard than I would otherwise have done, although,’ she smiled cruelly, ‘don’t bank on it. Now, what are you going to do with this miserable specimen?’

  ‘I’m working on an idea, Mistress.’

  ‘Then get on with it,’ she commanded, as she swept elegantly from the room.

  Chloe slid his feet back into his high-heels and looked at Charlene critically. He took a pair of the black French knickers from the cupboard and held them up against the man. He took a deep breath to calm his instinctive reservations, then caressed Charlene’s cock with the silk. There was no reaction at all.

  He took one of the realistic dildos from the cupboard, and held it in front of Charlene as he smeared it with lubricant. He squeezed a cushion behind Charlene’s hips so that his buttocks were pushed forward, allowing access to his anus, the bound man grunting as further strain was placed on his wrists and ankles.

  ‘Perhaps this is what you fancy, Charlene,’ Chloe said as he knelt down and positioned the phallus between the man’s tensed thighs, the flaccid cock inches from his face.

  ‘It’s, um, never really been something I’ve thought about,’ he replied, his voice tense.

  ‘Well, let’s see.’ Remembering the throb of excitement when Sophie had thrust the phallus into him earlier, he twisted the knob at the tight anal opening and harshly fed it home. Charlene jerked with pain and discomfort, but there was no response from the flaccid penis drooping towards the floor a few inches from his face. His pulse raced as he wondered whether peeling back the foreskin and taking it into his mouth would have any effect.

  But before he could take a decision the door opened once more and Sophie arrived with Barbara. She had put on a coat and had obviously told the woman nothing about the circumstances of her summons. Barbara’s mouth sagged as she took in her husband standing naked against the wall with the cloaked figure kneeling in front of him, apparently with his cock in
its mouth.

  ‘Ch-Charles,’ she stammered, ‘what on earth...?’ Her eyes glazed over as she slid to the floor in a faint.

  Chloe stood up and said to Sophie, ‘Help me strip her.’

  She was wearing a blouse, jacket and skirt, but as she was a dead weight undressing her was not easy. He pulled her into a sitting position and Sophie peeled the jacket from her shoulders and arms. The green blouse was unbuttoned, revealing a white bra brimming with heavy breasts. Sophie unclipped the bra and they swung free in all their glory. Chloe unzipped the skirt and pulled it down over her hips as Sophie lifted her bottom off the floor. Her silky hold-ups gripped high on her thighs, creating a ridge of flesh between their elasticised tops and the tight Sloggis that encased her hips and bottom, and which were stretched tightly between her legs, not entirely hiding the blonde thatch there.

  He rolled the pants down over her thighs, catching a glimpse of the thick labia lips with a hint of pink at their tight slit, and allowing the thick muff hairs to spring free. He left her hold-ups in place, and felt his cock swell as he took in the curves of her body, the thickness of her thighs and tight flesh of her tummy and hips.

  ‘On the other wall,’ he instructed Sophie, and they hauled her almost naked body across the floor, and with difficulty lifted her up onto the wall opposite her husband. Totally slack and hanging from her wrists, he could assess Barbara more carefully. When she had leant close to him in the office he’d been aware of how attractive she was. She had the female strength that excited him, and now she was hanging naked in front of him he realised how much mature women attracted him.

  She began to come round and began to tug frantically at the restraints. Tears rolled down her cheeks. ‘Charles, what’s happening?’ she sobbed, bewildered, her terrified eyes beginning to take in the characteristics of the room and the people in it. ‘What are we doing here?’

  Chloe stepped forward and tried to explain calmly. ‘Charles has been worried that he’s not been able to fuck you for some time. It has upset him and he came here to find some way of getting back to normal. He feared you might go with someone else, and he doesn’t want to lose you.’

  ‘And...?’ she asked.

  ‘No response so far,’ he replied. ‘But then, when I realised who he was I had an idea. And as I had already decided that I’d not be returning to work...’ he took off the cowl so she could see who he was, ‘...I asked Sophie to pop round and collect you.’

  The colour drained from her face and she began to tremble, almost fainting again. ‘Wuh-what are you going to do?’

  He turned to Charles. ‘How much do you want to fuck her?’ he asked. ‘What are you prepared to do?’

  ‘Anything.’

  ‘I want you to fuck her too, but for other reasons.’

  ‘Why?’

  ‘You could not understand, but both our futures depend on it,’ he replied. ‘Sophie, the cane,’ he commanded, and Sophie selected one of the canes from the rack. He took it and moved towards Barbara, and inserted the tip between the sex lips just visible through the thick blonde curls. He carefully and gently twisted his wrist, pressing the tip in towards her clit. She winced, first with pain and then as the edge caught the sensitive tip of her nub, with a tremor of anticipation.

  He looked across at Charlene, and saw his cock stir. Nothing substantial, but a slight movement that was clearly the result of his wife’s discomfort.

  He lifted the tip of Charlene’s penis with the tip of the cane. He instinctively knew that pain here was not what was required. He moved back across the room and struck Barbara a vicious cut across the tops of her thighs. A red weal rose on the soft flesh as she screamed in agony. He raised the thin rattan and struck another blow across the tips of her full breasts. She screamed again and writhed, her back scraping against the rough brick of the wall behind her. Almost before she had absorbed that blow he brought the cane up sharply across the tender undersides of her breasts.

  He glanced back at Charlene. He had been right. Charles clearly realised that she needed some forceful treatment but had not been strong enough with her. His cock was showing real signs of life and stiffening.

  ‘Get her down, Sophie,’ Chloe said. ‘We’ll put her across the horse.’

  Sophie released Barbara from the restraints. She stumbled unresistingly across the floor and was quickly strapped over the vaulting horse. ‘Don’t hurt me again,’ she panted. ‘I’ll do anything you want, but don’t hurt me.’

  ‘We will certainly do whatever we want,’ said Chloe, ‘and that may mean hurting you. You cannot have it both ways. If you want to have Charles fuck you, you will have to put up with what he needs to make him hard.’

  He went to the cupboard and selected a plaited lash, with tiny knots tied at the end of each strand. He moved in front of her and she began to cry again.

  ‘Oh, please no,’ she begged, but he brought the lash down with a vicious crack across the beautiful full curves of her mature bottom. His own cock was rock solid as it reacted to the steady rain of blows that cut into Barbara’s back, bottom and thighs. The whole area was crisscrossed with fine red lines, as the plaited lash demanded a rapid and painful reaction from the soft and tender flesh.

  Charlene’s cock was standing parallel to the floor, not yet reaching for the ceiling but solid and rigid nonetheless.

  ‘Sophie, the stool,’ he commanded, and she went to the corner of the room and brought back the low stool there. He put down the lash and parted the full cheeks of Barbara’s arse. The tight anal circle was flushed pink, and beneath it her sex lips were swollen, and when he parted her legs he could see that a stream of musky juices had run down the inside of her thighs from her engorged cunt, onto the suede covering of the horse.

  He returned to Charlene, reached behind him and unceremoniously eased the phallus from his anal tract. Then he went back to the horse and pressed the tip of the dildo against Barbara’s anus.

  ‘Please, no,’ she sobbed, shaking with trepidation and not a little anticipation, but seeing the increasing size of Charlene’s erection Chloe knew he was making the right decisions and pressed it into her, forcing her sphincter wide open and ignoring her protests and tears.

  Charlene’s penis was well above the horizontal now and his own cock was bursting. The dull ache in his balls needed relief and here was his chance. Barbara had apparently wanted him - now she was going to get him. Rather more than she had bargained for, he suspected, but her husband’s reaction would make up for it.

  He stepped onto the stool, pushed Barbara further over the horse so that he could have easy entrance between the swollen lips of her labia, which despite her protests were slick with her running juices. Her spasms were beginning to expel the phallus so he screwed it back into her, turning it so its realistic testicles were not his way and called Sophie to bring the duct tape to him. Ripping off a length he applied it across her bottom, pressing it tight onto the raised ridges of her whipping so the phallus was held firmly inside her.

  He watched the pulsating folds of her moist sex lips as the muscles of her vagina reacted to the solid rod in her rear passage, and in anticipation of being filled with the real thing.

  He eased the tip of his knob between the folds, wondering whether to drive it deep inside with one thrust or to enjoy the gradual enveloping of his shaft by her hot, smooth, tight tube. He opted for the slow insertion and was pleased he did. He felt her open willingly ahead of his cock and was able to enjoy the hardness and solidity of the phallus through the thin membranes of both tunnels as his knob slid against the rippled surface. She gasped as he reached deep into her and his balls nestled into her thick pubic hair. He withdrew, slowly still, and took further pleasure in another leisurely thrust until she had swallowed his whole length once again.

  He turned to Charlene. ‘I’m going to fuck her rigid now,’ he announced, and with a huge pulse Charlene’s cock was full and
vertical. It was the largest he had ever seen, a full ten inches long and thick in girth.

  ‘Call Mistress, now,’ Chloe said to Sophie, thinking she’d be delighted with what he’d achieved, and she obediently left while he began to thrust rhythmically into Barbara’s satisfying and willing channel. He knew he would not last long; the pressures and the pleasures of the day had built up in his balls and he desperately wanted relief and release. The intensity of his thrusts increased and he could feel the amplified spasms of Barbara’s response as she too began to reach her climax.

  The door swung open, and Mistress Amanda took in what was happening at a glance.

  ‘Stop,’ she commanded, her eyes flashing. She was clearly angry. She strode over to Chloe and dragged him off Barbara and sent him sprawling to the floor. ‘On your knees, slave.’

  He crouched before her, head bowed. ‘I’m sorry, Mistress. I thought—’

  ‘You must be punished - but that can wait until this mess has been cleared up. You were clearly told, Chloe, to return Charlene to me when you had made something of him. You may have achieved the primary objective but my instructions must be followed to the letter.’

  She freed the whip from the belt at her waist and cracked it agonisingly across his right shoulder. ‘You have no authority to take matters into your own hands to this extent.’ The whip slashed down on his left shoulder and then his right.

  ‘And to bring someone else into my apartment, someone who was brought here by what I can only assume to be false pretences, is an outrage.’ Two more blows struck him sadistically just an inch parallel to each of the first three cuts.

  ‘I will deal with you properly later. Curl up over there and do not move until you have my express permission.’ He crawled over to the corner and huddled miserably on the floor, his shoulders screaming with the raw pain and his rigid cock aching for release. He wondered whether he dared risk rubbing himself off, but his Mistress anticipated this and snapped, ‘And don’t you dare touch yourself. It will be the worse for you if you do!’