Chloe's Contract Read online

  She removed the towel and put it back on the trolley. ‘You look lovely, Chloe,’ she told him as she showed him his reflection in a hand-mirror. And he had to agree. The incessant ache from his bottom, cock and nipples could not detract from the beautiful, womanly look that Sophie had achieved.

  ‘I think you’re ready for Mistress to receive you soon. She’s expecting a client, but you’re an integral element in the scenario so I must be sure she’ll be happy with you, otherwise I’ll be in trouble. And I’ve been told to tell you that this is a very, very important part of your induction. Mistress will expect total obedience and complete acquiescence to her wishes and instructions.’

  ‘You know I want to please her, and you, Sophie,’ Chloe said, his voice thick with emotion.

  ‘Pleasing me, unless Mistress wants you to please me, is of no consequence,’ Sophie rebuffed him. ‘I’m doing this to you and for you because she wants me to. You’re a sweet girl, Chloe, and I’ve already come to like you a lot. I’m sure we’re going to have some exciting times together, but we must remember that Mistress’s wishes, needs and desires always come first.’

  She clapped her hands together brightly. ‘Now, another quick practice before I take you to Mistress. She’ll want you to serve her visitor tea this afternoon.’

  Chloe got off the stool slowly and carefully. He was beginning to understand what Sophie was telling him. If he kept the thought of Mistress Amanda at the forefront of his mind he started to see that his trials were a tribute to her, a mark of his love and respect that could be demonstrated in no other way. Money could buy gifts, love could be a distraction and devotion could fade, but pain was a constant reminder of his inner urge to give himself totally and absolutely into the hands of a Woman.

  By taking short steps he could stand taller, almost enjoying the pressure cocooning his trapped cock as he moved, recognising that he really looked female and had been feminised. He knew that, unlike Audrey, he was a distance from being able to pass as a woman, but he felt he was really on his way.

  ‘How am I going to serve tea when I can’t move my arms?’ he asked, the thought suddenly coming to mind, and Sophie laughed at the timing.

  ‘I’ll release you at the appropriate time,’ she chuckled. ‘Don’t worry your pretty head about that.’

  After a little more practice he was beginning to feel confident in the high heels, brushing his thighs together under the tight skirt, and sensing that his bottom was swaying from side to side provocatively. The pain as he moved became part of him and encouraged the feminine movements that the butt plug and his rubber-encased and ringed cock were forcing him to adopt.

  Sophie looked at the clock. ‘Almost time,’ she said, and a physical shiver of anticipation ran through Chloe, having its own effect on his tormented cock and plugged rear passage.

  ‘One final thing I have to tell you, before we go.’ Sophie said. ‘You are not just expected to be feminine, but sexy too. If you have to bend over to pick something up, for example, make sure you allow your skirt to ride up. Make sure you smile prettily, and even if you’re in pain Mistress will not expect you to show it. And keep your shoulders back so that your nipples stay hard and the rings show through your blouse.’

  She looked critically at him as he stood before her, and then the doorbell rang in the distance.

  ‘That will be Mistress’s client,’ Sophie informed him, unnecessarily, as he’d been expecting it throughout his feminisation process. ‘You may have to wait a few minutes before you’re needed.’

  He sat again, nervously trying to find a position in which he could be comfortable, but with his nipples newly pierced, his cock and balls ensnared, and his bottom plugged, it was pretty impossible.

  A bell tinkled from another part of the house.

  ‘That’s Mistress’s signal for you to serve tea,’ she said as she unclipped his wrists. ‘You’ll find everything prepared in the kitchen. Just make the tea and take the tray in. I’ll open the door and Mistress will instruct you from then on.’

  Chloe got up and swayed a little on his heels until he found his balance. Together they walked out of the room, along the corridor and into the kitchen. Everything was ready as Sophie said it would be, so he boiled the kettle, filled the teapot and lifted the tray. He remembered his resolution to see his pain as a tribute to Mistress Amanda, and was able to straighten his back and hold his head high. The result, he could feel, was a sexier, more confident walk. Sophie moved in front of him and opened the door ahead so he could enter.

  His Mistress was sitting upright in a leather armchair, facing him. She was wearing a fabulous, sinuous dress that fitted her magnificent figure to perfection. The cut across her breasts was low, emphasising their exquisite size and shape. Her heels were high, and the flow of the silk over her long legs showed their glorious shape to perfection, and her whole bearing and beauty confirmed that this was the woman he wanted to worship forever. She looked wonderfully feminine although, somehow, retained her dominance as she glanced towards him and said, ‘Thank you, Chloe. Just put the tray down on the table and pour us both a cup of tea.’

  Sitting facing Mistress, with her back to where he stood by the door, was a woman with beautiful auburn hair that fell lustrous and glossy down her back. He walked over to where they sat, still unable to see the face of the newcomer, and bent to put the tray on the occasional table between them, his cock straining within its tight confines, his skirt riding up a little at the back, and he was confident that he looked good, sexy and feminine, and that the visitor had a great view of her stockinged legs.

  ‘My, what a pretty new maid you have,’ the visitor remarked and the tray, just an inch or so above the tabletop, slipped from Chloe’s fingers and dropped with a crash, upsetting the cups and spilling the milk.

  It was Anne - his ex-wife!

  Chapter Thirteen

  Chloe collapsed to the carpet. He did not know what to do or how to react to their obvious delight in his absolute humiliation. They were genuinely enjoying the sight of him with his legs splayed, his skirt up around his waist, his blouse awry, with the metal rings clearly showing that he’d been pierced. His shoulders shook as the tensions and the torments of the last few days rose to the surface and he sobbed uncontrollably, his chest heaving as he gasped for air.

  Sophie came in and helped him up. ‘Behave yourself,’ she hissed. ‘Pull yourself together!’

  She turned him to face away from the two women and dried his eyes with a tissue, smoothed his skirt down and adjusted his silk blouse, pulling it tight into the belt so that the nipple rings stood out even more clearly. Then reattaching his wrists to the belt, she said, ‘Now turn around and wait quietly.’

  ‘I can’t,’ he whispered, desperately. ‘I really can’t.’

  ‘You must,’ she replied. ‘Your Mistress expects it.’

  So he straightened up and slowly turned around, his head bowed.

  Mistress Amanda and his ex-wife were standing close to each other, side by side. They were two beautiful women. He hardly recognised Anne, who appeared to have developed a most attractive poise and self-assurance since they’d parted, but he quickly realised that this was his perception at the time. She must have been gaining that self-confidence throughout their married life as she became more successful and he, wrapped up in his own work and sexual fantasies, had just let the changes slip by without recognising them.

  ‘You look really lovely,’ Anne said. ‘I always knew this was how you were supposed to be, but knew of no way of allowing you to become it, and me to become what I wanted, while we were still married without it destroying both of us.’

  ‘What do you mean?’ he asked.

  ‘You wanted me to be your mistress. I couldn’t be that. Apart from the fact that I got bored of sex with you,’ she explained bluntly, ‘I was certainly not prepared to take the lead.’

  ‘Then why did you
marry me?’ he asked disconsolately.

  ‘Because she was pregnant, you silly girl,’ Mistress Amanda told him.

  ‘When we met I was never much interested in men, and at that time I was the only virgin among my friends,’ Anne went on. ‘So I chose someone “safe”, and you were very suitable. But neither of us had much experience so I fell for Mark that first time, and Andrew almost immediately Mark was born.’

  ‘What do you mean, “never much interested in men”,’ he asked.

  ‘What do you think?’ Mistress said, reaching for Anne’s hand and taking it gently. She drew Anne to her and their lips met as they kissed tenderly.

  ‘We’ve been lovers almost since we met, when Anne was the partner at her company asked to look after my financial affairs.’

  So she did have a lover all along, Chloe realised - but a lesbian lover? This astonishing revelation and the pain of his restraints suddenly overwhelmed him, and he staggered and would have fallen had not Sophie supported him. He had endured the pain, but this sudden drop from euphoria to dejection might be intolerable, and if this was the level of humiliation Mistress had in mind for him he wondered if he could sign the contract if and when it was offered.

  ‘M-may I ask a question, Mistress?’ he ventured.

  ‘Of course, Chloe.’

  ‘Is this what you meant when you said I had to understand the ultimate in humiliation as well as the ultimate in pain?’

  ‘Partly, yes, but we haven’t finished yet, and for you there can be pleasure in that humiliation, as you will see.’

  He did not understand and wanted more information.

  ‘But no more questions for now,’ Mistress said. ‘Sophie, take Chloe to my bedroom. You know where she’s to be placed.’

  ‘Come along, sweetheart,’ Sophie said, and taking him by the hand she led him, still shaking with shock, to the lovely room that was Mistress Amanda’s very personal and intimate sanctuary.

  Against one wall, behind heavy drapes, was a St Andrews cross. She took him to it and turned him around so that his back was against the timber and he faced the bed. She took off his blouse and placed a ball gag in his mouth before unclipping his wrists. She stretched his arms up high and strapped them to the upper arms of the cross, and parting his legs, strapped his ankles wide apart to the lower arms. His feet only just touched the floor and the position, painful in itself, instigated new waves of pain in his cock and arse and nipples.

  He had a full view of the bed, but could not move or say a word. His cock, which despite his experience remained uncomfortably solid, stiffened still further and he felt the steel rings bite deeper into his swollen flesh. At the same time, the position emphasised the depth and size of the phallus inside him, and his nipples throbbed from the holes that pierced them. He tried to bring Mistress Amanda to the forefront of his mind, but all he could see was her hand reaching out to hold Anne’s in a lovers’ grip.

  The door opened and the two women entered. They stood in front of him. Mistress described the fitting of the anal plug, emphasising its size and his ability to flex his anus, and lifted the nipple rings, showing his piercings and demonstrated the ways in which the rings could be pulled and twisted. The pain was excruciating but he could do nothing but scream around the ball gag. Then she lifted his skirt and ran a sharp fingernail from the base of his cock to its tip, explaining to Anne the restraining steel rings that were keeping him in a perpetual state of torment. He writhed as far as he could, but even those small twists and turns created further agonising pain, so he kept still as Mistress pulled and squeezed his balls to demonstrate how much they’d been stretched.

  Anne murmured polite interest but did not take part in the torture, for which he was grateful, but suddenly Mistress said, ‘Take off your knickers, Anne.’

  Anne looked at her questioningly, but slipped her hands underneath her lovely dress and took them off nonetheless. They were soft pink silk that hardened him still further as Mistress gently stroked their warmth against his cheek. Then she unclipped the gag, and screwing the panties into a tight ball, fed them deep into his mouth. He tasted the faint musk of Anne and savoured the scent of her sex. He was embarrassed, but his excitement was growing again and the pain became a tribute once more as Mistress kissed him gently on the cheek, and told him he was a good girl.

  She took Anne’s hand and led her to the bed. Their arms wrapped around each other and they kissed deeply, their hands exploring each other’s body, emphasising their beautiful feminine curves as their movements tightened their dresses over them.

  Through his pain and embarrassment Chloe considered his feelings for his ex-wife, the woman he had once loved, who had borne his children while all the time being in love with and making love to the Mistress he worshiped. He realised it was a complex tangle of emotions that would take many months to understand, but he already appreciated that the whole experience was dragging him deeper into his intense relationship with his Mistress.

  Mistress and Anne had completely forgotten him. They murmured loving words as they began to undress each other. It was clear that Mistress took the lead, for Anne’s dress dropped to the floor first, revealing a beautiful and stylish bra from which her breasts swelled deliciously, and a matching suspender belt, all matching the panties stuffed deep inside his mouth.

  He’d forgotten what a superb body she had, her skin smooth and silky, her curves rounded and feminine, her legs long and shapely, and as her bra fell from her breasts he remembered the wonderful fullness of them. Mistress clearly appreciated them too, as one hand caressed them, cupped them, and fingers tweaked a budding nipple, while the other slipped between her moist thighs and stroked the opening sex lips.

  She turned so Anne could unzip her. The sound brought a sob of desire from him and his muscles tensed as her lovely dress slipped from her shoulders and revealed her magnificent body, in a basque, suspenders and stockings. She wriggled out of her high-heeled shoes and her thong and moved Anne to the bed so they could lie down together. Mistress peeled back the silk covering her right breast and Anne dipped her head and began to suck her nipple. She took it tenderly between her lips and nipped and caressed it with her tongue. He could see the glow of pleasure spread across the face of Mistress Amanda as she leant back and enjoyed the sensations her lover was giving her.

  He had no doubt that they really were lovers. This was not a performance; he could see it was a sensuous display of genuine affection and deep commitment, and as a result it was deeply humiliating, for he wanted to be his Mistress’s greatest pleasure, but now knew he would never be allowed to be, and instead she was being pleasured by a woman he’d failed to excite in many years of living together as man and wife.

  Tears came to his eyes again, but there was no doubt that as Anne slid down the body of her lover to bury her head between her legs he was excited and energised by the view, ignoring him and concentrating on their own pleasure. Anne slid from the bed, kneeling beside it, and as she sucked and licked she would occasionally raise her head, her mouth, chin and cheeks glistening with juices, to smile at her lover. Mistress reached to hold Anne’s head and smiled too, before gently pulling her face back between her thighs.

  Chloe could see it was going to be a long, slow loving, so each could please the other to the maximum, whilst causing him the maximum discomfort and embarrassment. He watched as Mistress Amanda’s belly began to heave and her breath came in short bursts as her climax approached, and Anne’s tongue flicked her clitoris, increasing the speed and lightness of her touch. Suddenly Mistress Amanda took Anne’s head in both hands and ground her sex against the eager mouth as the waves of her climax took over her body and she shrieked with bliss. Anne continued to roll her tongue inside her as through a series on mini-climaxes she gradually came back down from ecstasy, moaning in a way that he longed for her to moan for him. He felt ready to explode, but the painfully tight rings were just enough to prevent h
is release.

  Anne climbed back onto the bed, and after a long kiss knelt across Mistress so that their parted thighs were towards him. Their sexes peeped mockingly at him and he watched transfixed as his Mistress’s hand moved between Anne’s legs and fingers slipped inside her. Anne’s sex opened readily and she wriggled further up her lover’s body, so that her hand could push right inside her. Anne settled herself, rotating her hips to maximise the sensations of the flexing hand deep within her. Her breasts were hovering above Mistress and he could just see Mistress sucking on one of Anne’s nipples. Anne was in a paroxysm of desire and began to grind backwards and forwards so that her lover’s hand moved smoothly in and out of her sex, at one moment exposing her fingernails and the next sunk to the wrist. Anne’s moans of pleasure became louder and Chloe felt his cock fighting against the restraints as he wallowed in a mixture of fascination, helplessness, desire and frustration. It was a heady combination that brought him so close to coming that the mental and physical anguish was intolerable. Nothing in his lifetime, including the events of the last few days, had prepared him for the depths of pain and misery vying with the voyeuristic rapture and worship of two women he was now experiencing, as he watched Mistress Amanda and the mother of his children making passionate love within a few feet of him. He could smell sex, and breathed deeply, taking the exciting aroma deep into his lungs.

  As Anne came he tensed on the cross, the first spasms of his release building from deep inside his loins. Anne sobbed in ecstasy and his balls pumped hot, thick spunk from his shaft, and he felt the viscous fluid bathing his cock within the rubber sheath. The tensions in his body eased and the pain became a joy and he realised that if this elation was the result of total servitude, it was what he wanted. Whatever Mistress Amanda wanted of him in the future he knew he could provide, and whatever the deprivation he would dedicate his whole being to her and do anything for her.