by David James
‘Once you’ve committed yourself to me you’ll have to suffer many deprivations,’ Mistress Amanda addressed him again, ‘for my clients are not always just cruel - they are inventive too. The ways and behaviours they need to indulge in so that they’re able to enjoy sex are many and varied. I have one who deliberately cuts her nails to a sharp point so she can do as I just did, but until you scream. And your screams will make her orgasm instantly. A regular male client needs three sissies - one to suck him, one for him to suck, and one to fuck him. Oh, dear Chloe, you have no idea of the range of sexual activities that can appeal...’
‘But you will,’ Anne mused. ‘You will.’
‘Don’t make assumptions,’ Mistress corrected her. ‘He has not yet made his choice.’
She turned her attention to him again. ‘Of course, if you do agree you will, like Audrey, always be referred to as a female.’
‘Yes, Mistress, and I look forward to it.’
‘You are still willing?’
‘Oh yes, Mistress.’
She smiled. ‘I’m pleased. Now come here.’
She carefully and tenderly took his cock and kissed its tip, then drew his knickers back up, tucked his length into them before freeing his skirt and allowing it to fall into place. ‘If you’re sure...’
‘I am, Mistress.’
‘...Anne will draw up the paperwork. It will give me complete power of attorney over all your assets, although Anne will manage them. She’s already arranged for you to be on indefinite sick leave from your job, and she’ll eventually negotiate an advantageous exit package for you. She’ll take control of all your affairs, so that should you ever return to normal life you’ll be well catered for. The contract also places you, personally, entirely in my care. Everything you need will be provided by me - but you’ll not need for much. Anne will have the papers prepared for signature by noon. We’ll need an independent witness, but I have a client this morning who’ll be more than pleased to do it.’
And so it was all decided and arranged, and upon being dismissed, Sophie took Chloe back to his cell to get him ready for the contract signing.
‘Mistress will want you to look your best and most feminine,’ she said, looking at him critically as he stood naked before her. ‘You certainly do have great potential. A few more weeks of exercise and hormone treatment is all that’ll be needed.’
She showed him a metal butt plug, into the base of which was set a paste diamond. ‘Now turn round and bend over.’
He obeyed and felt her rubber-gloved index finger nuzzling into his anal ring. ‘Open wide...’
He flexed the muscles and felt his entrance relax. ‘Good girl,’ Sophie said, as she lubricated the plug and pressed it home, fitting it deep inside him.
Then Sophie produced the most exquisite midnight-blue corset he had ever seen. It was beautifully made of silk panels blended with lycra, with a gusset that had three strategically placed openings, each with a silk drawstring through the neat seam around the edge. The front was scooped low and sweeping underneath his nipples, and as he drew the amazing garment on it wrapped itself around him, flattening his stomach, rounding and lifting his bottom and nipping his waist as if it had been tailored for him.
Sophie stretched the first hole over his throbbing penis and eased it down to the root of his shaft, before pulling the silk cord tight and tying the ends in a neat bow. The effect was to trap his cock in such a way that it stuck out almost horizontally. His testicles were pulled through the second opening and the cord tightened, so that his balls hung between his legs like ripe plums.
Sophie pulled the base of the butt plug through the third opening and tightened the drawstring around its neck, buried in his bottom so that the jewel marked the exact position of his anus. He accepted and enjoyed the discomfort of these new style restraints and smoothed his hands over his hips in sensuous delight.
He sat down to put on a pair of sheer, seamed nylons, feeling the plug settling deeper inside him as he did. His cock was bursting and he almost came as the stockings slid up his smoothly shaven legs and were clipped to the suspenders.
Sophie noticed. ‘Take care; Mistress will be very angry if you stain any of your outfit.’
Taking a long length of a ribbon, which matched the colour of the corset, she wrapped it several times around his helmet and tied the ends in a bow in the small of his back, forcing his erection back against his stomach.
‘No knickers today,’ she said, before inserting a beautiful pair of heavy, diamond-studded rings through his nipples. Then a matching pair was clipped to his earlobes. ‘I’d guess Mistress will want these pierced too, soon.’
Sophie then revealed a lovely dress which, as Chloe drew it on, fitted him as though it too had been made especially for him. The fabric was deep-blue, fine Chinese silk and cut on the cross, it hugged and emphasised the feminine curves created by his corset. Dark-blue high-heeled shoes and a matching diamond necklace and bracelet completed the outfit. He looked in the mirror and saw that his dress not only emphasised his innate femininity, but his masculinity too, as the outline of his cock and the nipple rings on his chest could be clearly seen.
Sophie applied a little light make-up and lipstick, and stood back to survey her handiwork. ‘You’ll do very nicely, Chloe,’ she said, pecking him on the cheek and surreptitiously sliding her hand against his cock from root to tip. ‘Very nicely indeed. Now I’ll go and see if Mistress is ready for you.’
As she left he walked across the room, enjoying the feminine sway of his body the outfit, plug and high-heels encouraged, and then watched himself in one of the tall mirrors, admiring himself from the side and front. He practiced placing his feet in positions that would emphasise his hips and thighs, and found he could do it almost instinctively.
After a short while Sophie returned. ‘Impeccable timing,’ she said. ‘Come along.’
As he followed her along the hallway his anxiety mounted. He was about to commit his life to another in a way that even a few days ago he had never even contemplated. But he had no real doubts in his mind.
Mistress Amanda, Anne and a tall, handsome man, dark-haired and cleft of chin were at the table in the dining room. The women wore day dresses, obviously expensive, and the man a dark suit with a white shirt, open at the neck. He stood with his head bowed.
‘Chloe, you look charming,’ Mistress enthused. ‘Doesn’t she, Anne?’
He blushed at the compliment.
‘Chloe, this is Alec,’ Mistress went on. ‘He’s agreed to be a witness to our agreement. You will thank him shortly.’
Chloe shivered in anticipation. How would he be expected to thank the man?
‘Come and read the contract, Chloe.’ Mistress Amanda got down to business. ‘It’s not a long document but it covers all our arrangements, and has been checked by my lawyer.’
Chloe glanced through it. His own management training recognised that it had been drawn up by an expert, and as Mistress Amanda had pointed out, was legally binding, and he didn’t hesitate for a second in signing and dating it with an eager flourish.
His Mistress signed too, and then Alec witnessed the two signatures. Chloe took a deep breath; there was no going back now. His Mistress kissed him warmly.
‘Welcome, Chloe. It will be an exciting journey, but you’ll belong to a community that wants to explore every aspect of sexual behaviour, but which cares for and supports its members. Welcome.’
‘I know you are going to fit in wonderfully, Chloe,’ Anne said, giving him an affectionate hug. ‘When we first got married I would never have believed where I would be now, but it’s been a stimulating and very exciting experience. We’ll be seeing a great deal of each other, not just because of the arrangements I often make for Mistress Amanda and her clients, but I know some of your management skills will be useful to us too.’
Mistress Amanda turned to Alec.
‘You were promised a token of my thanks. I can perform my usual services for you if you wish, tribute free, but if you prefer, Chloe is yours for an hour to do with as you please.’
Alec’s voice was deep and warm. ‘I’ll take Chloe please, Mistress.’
‘Alec likes to be beaten, so use your imagination if that’s what he wants,’ Mistress said to Chloe. ‘But he also has a sadistic streak that I, of course, can never allow him to express, so he may want to punish you too. You will use one of the bedrooms.’
Chloe took that as a dismissal, instinctively reached out a hand to Alec, and led him from the room to one of the client bedrooms. He pulled down the blind. He was quivering with tension but he finally managed to say, reasonably calmly, ‘I am at your disposal, Master.’
‘I’ve never been with a she-male,’ Alec said quietly, and it was clear, now he could do whatever he wanted, that he was uncertain about his choice to be with Chloe rather than Mistress Amanda.
‘You really can do whatever you wish,’ Chloe prompted, though secretly unsure of his own feelings.
Alec stretched out a hand and traced through the soft silk the outline of the ring in Chloe’s left nipple, and twisted it tentatively.
The little stab of pain was glorious to Chloe, and he winced, drawing his breath sharply through his teeth.
Alec did the same to the other ring, then both together, and then he reached around Chloe and unzipped the dress so it slipped with a sexy rustle to the floor. Chloe stepped out of it and watched as Alec gazed at him, taking in the mixed male and female signals he was displaying. He turned slightly, knowing he was attractive to any man wanting to explore his own sexual personality.
Alec shifted uncomfortably to cope with his erection.
‘Would you like me to suck you off?’ Chloe asked quietly, surprised how quickly and naturally he was taking control. He reached for Alec and removed his jacket, undid his trouser belt and unzipped his trousers, lowering them and his underpants to the floor in one movement. Alec, in a daze, allowed him to take off his shoes and socks and then his shirt. His cock was already sprouting erect from his groin.
‘I... I’m not gay,’ he blustered.
‘Neither am I,’ Chloe replied. ‘Just imagine my mouth is a woman’s. Sit on the edge of the bed.’
Alec sat down, looking a little bewildered, his cock pointing straight up at the ceiling.
Chloe knelt down and gripped it, savouring its girth and length, feeling his own cock and balls throb with desire and anticipation.
Alec began to moan and Chloe knew he would not be long in coming. He moved his lips to the magnificent cock and tentatively stretched them over the bulbous helmet. He didn’t think he could get anything like the full length into his mouth, but he didn’t have to because Alec’s spasms began almost instantly and Chloe blinked as smooth, salty cream hit his throat and he swallowed desperately.
Alec’s body spasmed as Chloe sucked every last drop from his wilting cock, before he flopped back, exhausted on the bed. He left him to relax for a moment before rising and lying beside him. He gently stroked Alec’s sperm-smeared cock and balls, but Alec suddenly sat up and hissed at him, ‘I told you I wasn’t gay!’
Chloe snatched his hand away immediately and got up from the bed. ‘I’m sorry, Master, I thought—’
‘You’ll pay for that!’ Alec’s rage seemed alarmingly genuine, as though he felt he’d been taken advantage of, and wanted revenge for the humiliation.
Alec stood up and examined the corset, its openings and the silk bows around them. Chloe stood submissively while Alec untied the ribbon around his cock, which immediately sprang to its pulsing, angled position. ‘You need teaching a lesson,’ he growled, pushing Chloe back onto the bed.
He untied the silk cord around the base of Chloe’s cock and viciously jerked, pulling it so tight that the opening dug deep into the flesh. He pushed Chloe’s legs apart and did the same to the cord around the neck of his scrotum. Chloe’s balls were full and close to bursting, and his cock was deeply in need of release.
‘Let’s see how much you can take, you little sissy. You like pain, right? You enjoy it, right? Let’s see if you really do.’
Alec reached across him, and using the two nipple ornaments dragged him to his feet. Picking up a thin cane from beside the bed he swept it down hard and fast on Chloe’s erect cock, raising a red weal about an inch from its base. Chloe doubled up with the excruciating pain, unlike anything he had ever known. The cane lashed down again, and as Chloe gasped it was snapped up in the opposite direction to lay a cut on the underside of his poor cock. As soon as he straightened up it lashed down and then up again. Chloe writhed in agony but knew he must behave as Mistress Amanda would wish, and he straightened up once again. The two final slashes from above and below made him cry out. Tears filled his eyes as he awaited further punishment, but the next was a vicious blow straight up between his legs, biting deep between his testicles and raising a vivid weal on his throbbing balls.
He collapsed onto the floor, unable to stay upright while waves of pain swept through his body. He lay crying and gasping on his back, but there was no respite.
‘Call yourself a sissy-slave?’ Alec mocked as he slashed the cane down onto his balls once again. ‘You are useless and helpless.’
He reached down with both hands and hauled Chloe back up to his feet by the nipple rings. The pain for Chloe was incredible. Alec was holding him upright by a nipple ring while raining blows indiscriminately on his cock and balls, sending shards of fire through him.
Breathing heavily Alec eventually slowed the punishment, and then pushed Chloe to the floor. ‘Call yourself a slave, a sissy? You’ve got a lot to learn.’
He grabbed his clothes and stalked out of the bedroom, leaving Chloe curled up in pain and frustration. His penis was still erect despite the battering it had received, but he was in too much pain to orgasm. Sophie found him writhing on the floor, and cradled him in her arms as he lay sobbing against her breasts.
‘Come along,’ she said, after a few minutes. ‘It’s time for you to rest. I’ll put some cream on your cock and balls, but for the time being Mistress wants you to keep the nipple rings and plug in as a reminder that you’re now owned by her.’
Chloe was beginning to regain his composure. ‘Thank her for me please, Sophie.’
‘She’ll appreciate that. And she’s still very, very pleased with you.’
Suddenly the pain and suffering Chloe had endured on her behalf faded, and he felt a warm glow of love for his Mistress. He knew that he truly worshiped her.
‘And she has a special present for you, too,’ Sophie added, and then popped two tablets from a small bubble pack. ‘Here, swallow these. You’ll need to take two each day for the first six weeks, and then one a day thereafter. Whether or not Mistress has any clients for you here or at the Abbey you’ll be milked every day. It’s the easiest way to monitor the hormonal balance.’ She smiled. ‘After all, we don’t want to lose the use of your cock, now do we?’
Chloe took the tablets from her and she led him back to his cell. As he passed the table in the hallway he saw that the contract he’d signed had been placed in a transparent file. His signature, the final symbol of his total submission, stood out. David James.
And below the signature, written in Mistress Amanda’s own immaculate hand, were the words, henceforward known as Chloe.
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