Chloe's Contract

by David James

  Chapter Eleven

  The asparagus had eventually become soft enough to be stripped layer by layer. The inside of Chloe’s mouth was sore and the process had taken time because he’d been distracted by the events in the training room. The sounds and the occasional comments had given him very little information as to what was actually happening, but he was painfully aware that it was excessively sexual, that he wanted to be part of it, and his cock was aching as a consequence. The chains and straps prevented him reaching to touch himself and masturbate, leaving him desperately frustrated.

  Under some circumstances it was possible, he knew, to come without actually handling his cock. The experiments he conducted on himself after his separation included torturing his balls by snapping dozens of elastic bands tightly around each one until the skin seemed to be about to burst like ripe fruit. He would then force his rigid penis down between his legs and trap it so that it chafed against the skin between his thighs and beneath layers of panties, tight roll-ons and thick tights to hold it firmly in place. He would lie on his bed, his ankles and thighs tied and his hands held behind his back by twisted flex, writhing facedown, twisting his head to watch an anal penetration video on his portable television. An important element of this, he found, was the time taken to come. If he masturbated, although he could in theory make the experience last for as long as he wanted, once the pressure began to build and the tingling in his cock began to grow he could not resist bringing himself off. But restrained and gagged and unable to touch his cock, he would thrash around feeling the head of his penis and his balls being rubbed raw by the friction generated by his bound thighs so that eventually, often almost the whole length of the film later, he would feel the familiar sensations that presaged a peak. This was not itself enough, and he would have to work his body hard to gradually develop the muscular waves of pressure that brought that full, jerking force of a climax, wave after wave, pumping hot jets of spunk between his legs, bathing his cock in warm sperm that gradually spread down the inside of his legs, soaking the fabric and leaving him truly exhausted.

  The training room became silent as the women left to shower, change and recover. He wondered whether they had fully completed their sessions for the day. He had no idea of the time, but it must surely be late afternoon or early evening, when he’d been told his one-on-one training would resume.

  Throughout the afternoon his fevered imaginings had kept his cock solid and his balls aching unbearably. But the excitement of the last day and a half took its toll and his eyes closed, his body relaxed against the wall and floor of the cell and he fell asleep, a limp stem of the asparagus still in his mouth.

  He was awoken when the door of the cell was opened and a woman he didn’t recognise unchained him and helped him out.

  ‘Time you had a stretch,’ she said. ‘You have a busy evening ahead.’ Her voice was soft and low and she was wearing Mistress’s usual submissive uniform of black French knickers and top, with black stockings and black patent leather high heels. Her hair was long and beautifully styled, the legs slim but strong, and she had small breasts whose nipples just marked the surface of the silk top. As she turned he became aware of a pertly rounded bottom, but as his eyes got used to the light he realised that she was too muscular for a female, and her features, although not entirely masculine, were not those of a woman. This must be Audrey.

  He had never ceased to be amazed at the way in which a beautifully rounded bottom encased in silk or satin, and a glimpse of naked thigh between stocking tops and sexy knickers, could turn him on so completely. And just an impression of the outline of a nipple against a smooth top could send him into paroxysms of desire. He knew Audrey was male, but her looks still excited him as the feminine ‘signals’ penetrated his mind.

  She had clearly being receiving hormone treatment, because the hair on her arms was soft and fine and he was sure her breasts, though small, were real by the way the outline of the nipples moved underneath the top. As he stood up to stretch he spied the fullness in the front of her knickers, indicating the weight of a cock and balls. He wondered how long it would be before he was able to flex and open his anal ring, as he’d seen Audrey do on the video earlier.

  ‘Do you need to use the loo?’ he enquired. ‘You can have a crap but you mustn’t piss, Mistress says.’

  ‘I’m not sure I can do one without the other,’ Chloe replied.

  ‘Then you’ll have to learn. Mistress likes her slaves’ cunts to be clean and their bladders to be full.’

  He’d not thought of his anal tract as his ‘cunt’ before, but he saw the sense of the comparison and it was clear that Audrey was quite comfortable with the idea.

  ‘Come along and I’ll show you.’

  Audrey led him, still naked, to a sumptuous bathroom and indicated that he was to sit on the toilet.

  ‘If it hasn’t already been explained to you,’ she said, ‘don’t forget that you must always go to the toilet sitting down. You are expected to behave as a female as far as possible. You’ll also find it easier to crap without pissing.’

  Chloe knew his rectum was full and he need to go, but he wanted to pee too.

  ‘Grip your balls and the base of your penis tightly between your thumb and first finger, pulling both up and out from the toilet. Psychologically you’ll find you can then concentrate at the back and let go.’ Audrey explained. ‘Have you begun your stretching exercises yet?’

  ‘Yes, this morning.’

  ‘Good, imagine the speculum is opening inside you.’

  He sat back on the toilet seat, grasped his cock at the base and balls at their neck and held them tightly, pulling them forward. His cock had regained much of its hardness, which he knew would help a lot, and realised it was not as difficult as he’d imagined. He concentrated on his anal ring and felt it relax and open, allowing him to go. He would have liked to piss as well, but the anticipation of the coming encounter, whatever it was to be, had hardened his cock still further and he couldn’t have done so anyway.

  ‘Now you shower,’ said Audrey, turning on the controls.

  The hiss of the water sluicing across his body was welcome, except where the needle drops of the power shower bit into the still raw stripes across his back and buttocks, and the soap stung where the skin had been broken.

  He stepped out of the cubicle and Audrey patted him down with a soft towel, and when he was dry he turned him round and smoothed a cooling cream into his wounds.

  ‘Aloe Vera,’ she said. ‘This will help them heal, just in time for you to be ready for your next session tomorrow.’

  Chloe was disappointed. ‘I thought we were going to continue my training this evening,’ he said.

  ‘Oh, you are, but not on your back and bum,’ she replied. ‘I am to concentrate on your cock, balls and bottom to prepare you for Mistress later.’

  She handed him a top, French knickers and high-heeled shoes. ‘Put these on,’ she instructed. ‘Have you been allowed to wear high heels yet?’

  ‘I did last night but I wasn’t allowed to wear stockings’

  ‘Now you’re in training rather than paying for Mistress’s services you’ll not be allowed stockings. And you’ll have to stick to three-inch heels for the present. Stockings and higher heels are privileges you have to earn. Mistress allowed me to wear stockings when I could open for a B-size prick, and four inch heels when I could take eight inches. I can take a ten inch ‘C’ now,’ she added proudly.

  Chloe determined that he’d be able to match Audrey. He longed to have Mistress Amanda’s approval. He finished dressing and followed Audrey, walking very carefully in the three inch heels, out of the bathroom and along the corridor into yet another room, not as bare as the training room but with a further range of couches and padded benches of various heights.

  ‘We’ll start with some more anal stretching. Mistress has a special client tonight who will provide a usef
ul exercise for both of us.’ She smiled. ‘You’re very lucky, I can tell you. Now, take off your knickers and bend over that bench. Do you need to be tied down?’

  ‘Do I have a choice?’

  ‘Up to a point, yes. Mistress knows that being restrained and being restrained painfully can be pleasurable in itself, and for many that is an integral part of their experience. They want to be forced, to feel they are being made to suffer. You are unable to escape and that heightens the pleasure you ultimately feel. I understand that applies to you. However, true submission is in the receiving of pain and humiliation freely without wanting to escape, and that is the level to which Mistress likes her slaves to aspire. But it is a long hard road, so restraint can be an important mechanism for many of her submissives.’

  Chloe thought about what Audrey had said. He wanted to do what his Mistress wanted, but he knew that painful restraint was becoming an integral part of his humiliation. So he decided that he didn’t yet feel ready to offer himself without being bound, and said so.

  The bench was long and about the width of his body, so that his arms and legs could conveniently hang down on each side. It was not flat and he could see when he was laid along it, his buttocks would be raised and tilted for what he immediately realised was easy access.

  He lowered his panties and stepped out of them, almost overbalancing as he wobbled on one spiked heel after the other.

  ‘You’ll soon get used to them,’ Audrey said. ‘Sophie allowed me to try a pair of five inch heels last time I was here. Now they are scary.’

  Initially he was relieved to see there was a hole in the bench, through which his cock and balls could hang, until he remembered the exquisite pain he experienced with his cock ground into the suede of the vaulting horse in the training room. However, he said nothing and lay facedown on the bench, wriggling to feed his cock and balls through the hole. Audrey wrapped velcro straps around his wrists and ankles, and another longer strip was tightened across his waist, holding him firmly onto the bench.

  ‘We’ll start with a little stretching,’ said Audrey. He stood behind Chloe so that he had a good view of his bottom and the tight ring of his anus. ‘Now, try and flex your buttocks. Imagine you’re about to crap. You need to mentally ‘feel’ the stool pushing its way out.’

  His exertions that morning enabled him to flex the sphincter muscle a little, and he pushed as hard as could.

  ‘Not good enough,’ said Audrey. She came around to the front of the bench. ‘Like this.’

  She bent over so that her bottom was thrust close to Chloe’s face and dropped her knickers. He gazed fascinated at the smooth flesh and the heavy balls hanging down between her legs as with a little wiggle, the puckered star opened and he could see right into her dark tunnel. She held it for a moment and then the orifice closed, so Chloe was faced once more with a shuttered hole.

  ‘Now, try again,’ she commanded.

  Chloe concentrated every muscle, his cock stiffening through the hole as well, but it didn’t seem to make any difference, although Audrey was pleased. ‘A little better,’ she said. ‘I can see you’re trying. Perhaps we could use the stick and carrot technique. It’s often effective.’

  She picked up a flexible cane, and a narrow butt plug.

  ‘Now we know this plug will go in quite easily,’ she explained, ‘but I want it to do so without me having to push it in any way. Then I want you to clamp down on it.’ She flicked the cane through the air. ‘And this will punish your balls if you can’t do it.’

  She moved behind him again and placed the nose of the plug against his back passage. He strained every muscle against the normal clench of his sphincter, and felt Audrey nuzzle it between his cheeks. There was a sudden crack and it was a moment before he realised that the cane had slapped sideways against his balls beneath the bench, sending a sharp stab of searing pain through the sac, crushing the tender swellings of his testicles inside. He pushed again.

  ‘Now, that’s much better.’

  He could feel he was more open, but the next crack against his balls forced the nub of the phallus back out so he was back at the beginning.

  ‘That’s only to be expected, Chloe. Have another go.’

  He strained, and suddenly felt the butt plug slide in. Audrey had used a little pressure but he knew he’d opened up as required for a few seconds. Audrey tugged at the plug but Chloe’s sphincter was now firmly clamped around its neck so it was firmly embedded.

  ‘Good,’ she said. ‘Now hold it in against my pull.’ He did so but it was only a moment before the vacuum released its intruder with a sensuous sucking sound and a stab of discomfort.

  ‘What you have to learn to do is to open without losing the natural elasticity of the muscles. But you’ve made a good start. I think just an hour with the speculum and I can report good progress.’

  She took the stainless steel gadget, wound it closed, lubricated it and expertly slid it inside him. After the butt plug exercise he was expecting the intrusion, so there was virtually no pain as it twisted into his anal tube, but there certainly was as Audrey began to turn the grip so that the metal leaves expanded to force the tight ring open wide.

  ‘Mm, not bad,’ purred Audrey. ‘Now I want you to let it go so it drops out. I think you’ll manage it with a little encouragement.’ He brought the cane sharply up three times in quick succession against Chloe’s vulnerable, swinging balls. Apart from his squeal of pain the result was a reaction that clamped the speculum tighter, but as the pain faded he found that the prospect of three more swipes allowed him to relax against the leaves expanded inside him. It was not enough to release it by any means, but Audrey said that she’d not expected him to be able to. ‘But,’ she said, ‘it does mean I can open it further,’ and she gave the handle another half turn, giving him a further dose of anguish.

  Audrey then took the cane and inserted the tip into his open anus, and he felt it nudge around intrusively as she rotated it deep inside him.

  ‘Now we have to begin to stimulate the nerve-endings inside your cunt,’ she explained. ‘Most of your zones of stimulation are in your cock, your nipples and the muscles they affect when you come. This area,’ she pressed the tip of the cane against the wall of the passage, ‘is unused to being pleasured and, to begin with, apart from the psychological pleasure you have in being penetrated and filled, the actual sexual arousal is limited. What we have to do is to encourage these nerve-endings...’ she moved the rounded tip much more gently, ‘to respond in the same way as a cunt does.’

  Chloe realised that the smooth rubbing which at first had just felt like internal pressure was now beginning to generate a sexual response.

  ‘It takes time, Chloe,’ said Audrey, ‘but with help and training I’ll encourage your cock to become the equivalent of a clitoris, and your tunnel to respond physically just as a woman’s does.’

  He was beginning to wriggle against the tip of the cane deep inside him, but she withdrew it quickly.

  ‘Not so fast, Chloe. You must remember that all this is so we are more useful to Mistress. There may be pleasure in it for you eventually, but that is not the purpose of these exercises.’ She flicked the cane against his hanging penis with expert precision, causing a yelp of pain, but then a warm glow of ecstatic radiance suffused his loins as the pain spread deep within him.

  Audrey wound back the speculum and it slid easily out of his anus. ‘You’re still open, Chloe,’ hissed Audrey. ‘She should close as soon as she’s empty.’ He shivered as an intense pleasure swept through him. Audrey had referred to his anal tract as ‘she’, and he felt he’d taken a real step forward. He was to be used and abused as a female by Mistress Amanda, for her delight and pleasure, and she could also use his cock in any way she chose. He drifted into a trance as he imagined the delights to come, but he was brought sharply to his senses as another intruder nudged at his anal opening.

  �
��You’ve done well, Chloe,’ Audrey said. ‘I opened the A-size speculum to its fullest extent just now, so let’s see if you can manage the B-size.’ She smiled artfully. ‘Open wide.’

  Chloe gathered all his strength and focused on opening his cunt.

  ‘Good,’ said Audrey, as she slipped the larger instrument inside and began to turn the stem so that the leaves unfurled, and once again opened his dark passage to the air. The increasingly tender skin around his entrance seemed to split under the pressure, but although he felt the muscle must tear under the strain he put his trust in Audrey.

  ‘That will do nicely,’ she said. ‘An hour of that will do you a lot of good. You know what to do; I’m sure that Sophie has instructed you in the technique.’

  He was alone as Audrey left the room, his balls hanging full, heavy and sore from their beating, and his cock stiff, raw and aching. Every sinew seemed tender, but he was determined to delight his Mistress and once again he strained every muscle to manipulate the solid phalanx of stainless steel stuffed into his rectum.

  It was almost an hour later when the door opened and Mistress Amanda, alone, came into the room, removed the appliance, released him, and smiled. His world lit up. She was pleased with him. He knelt down before her. He wanted to thank her but knew he should not speak before being spoken to. She had changed into a tight rubber corset that reached down into her high-heeled boots and rose up to her throat. Her nipples showed hard and ruby-red through two small holes in the costume, and there appeared to be a flap running down her stomach and between her legs, beneath which was the bulge of what he deduced was a strap-on cock.