Island Discipline Ch. 08

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Kristy makes a big mistake and pays for it!
7.6k words
4.44
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Part 8 of the 23 part series

Updated 10/25/2022
Created 08/24/2009
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Cyberdiva68
Cyberdiva68
601 Followers

Eventually she heard the sound of a key turning in the lock and the door swung open. David strode into the room and re-locked the door behind him.

"Assume Position 1!" he commanded and Kristy sank to her knees, wincing as the motion set the weights attached to her nipples swinging.

David bent down and with practised ease flicked the clasp of her bra open. Her breasts were now exposed and unsupported. He removed the gag from Kristy's mouth and slowly unzipped his fly. "You know what to do, slave," was all he said.

Kristy looked up at him. "Please Sir, may I use my hands?" she asked.

David considered for a moment before answering. "Very well, Slave, but the result must be worth my granting your request."

Tentatively Kristy reached out and took his cock in her hand, stroking her fingers up and down its length. Then she brought her tongue into play and allowed her fingers to follow the track it made. Slowly she could feel the shaft start to stiffen and moved her fingers up towards the head where a drop of pre-cum glistened. She caressed it with the palm of her hand, using his pre-cum to lubricate it before encircling the shaft and stroking up and down it's length. As his cock started to stiffen further, she moved one hand underneath to cup his balls, licking each one in turn, sucking it into her mouth before releasing it. David gripped the edge of his desk for support. It looked like she was developing a real talent! She moved her mouth back up his shaft, her hand following in its path, constantly in motion, stroking and caressing, exerting firm but even pressure along its length. When she reached the head she hesitated slightly before plunging downwards and taking him deep into her throat. David gripped the edge of his desk harder. He couldn't let her know how good this felt! Again she pulled back before enveloping him once more. This time she let her teeth graze very lightly against his skin. David could take no more and seizing control he grabbed her hair, powerfully thrusting into her mouth, harder and faster until he came. Without being told, Kristy's tongue swirled around his cock, licking away every last trace of semen and giving him (although she was unaware of this) a chance to regain his composure.

He pulled away from her and readjusted his clothing. "You will lie on the couch on your back, slave" he instructed.

Kristy obediently moved to the couch and lay down on her back, wondering what was to happen next. David took a ball gag out of his desk drawer. "Open your mouth," he instructed and when she complied, he pushed it in and fastened it securely behind her head.

Taking hold of her ankles he pulled her down the couch until her ass was resting high on the arm. He then took the two lengths of cloth he had previously used to gag her and secured her ankles to the legs of the couch. She was now laying completely exposed. David hadn't finished yet, however. He returned to his desk and took out a vibrator.

"You will use this in your pussy and on your clit," he instructed. "I expect you to do your utmost to bring yourself to the brink of climax, although" he warned, "if you cum before I give you permission, you will be sorry!"

Kristy shook her head, wide-eyed. She couldn't do this! To masturbate with someone looking on was something she had never done and she felt her face warm as she blushed in embarrassment.

"Come, come," David taunted. "After your very public display in the hotel suite where you rode, what was his name, Carlos for your own gratification, a little thing like this should be child's play!"

Kristy closed her eyes as she remembered the events that had led to her present predicament. It was true she had selfishly used that man for her own pleasure without considering his needs or feelings.

David's expression hardened. "Do I need to reinforce my instructions?" he asked. "Before she could shake her head he continued. "Maybe I do. Very well, you were warned, slave!"

With that he brought his hand down hard across her exposed clit and pussy, making her scream into her gag. Twice more he repeated his action before pausing.

"Is my slave willing to obey me now?" he demanded.

Kristy frantically nodded her head and took the vibrator he held out to her. At 8" long and almost 2" wide, it was larger than the ones she had used previously and she wasn't sure if she could take it. Nevertheless, she had to try. She switched it on and lightly rubbed it in between her pussy lips. To her surprise it slid between them easily. She was already dripping wet! She moved it up and rubbed it over her clit, groaning against her gag as the engorged nub responded, sending shivers through her body. Finally she gathered her courage and slowly slide the vibrator between her lips and into her pussy. David grew impatient and placing his hand over hers exerted a firm pressure and forced the vibrator deep inside her. Kristy gasped at the feeling of her pussy being stretched. The vibrator was so thick that she could feel her g-spot being stimulated. His hand still on hers, David pulled the vibrator out and once more plunged it in deeply.

"Carry on," he said.

Slowly at first, but then with increasing urgency, Kristy worked the vibrator in and out of her pussy. She instinctively moved her other hand down and started to stroke and tease her clit. David leaned forward and quickly yanked the clamps from both nipples. Kristy screamed against the pain this caused but it quickly merged into the pleasure coursing through her body.

"Don't you dare cum!" David warned.

Frantically, Kristy gathered all her willpower to stave off the impending orgasm. This was a difficult undertaking as David was now pinching and teasing her abused nipples, again causing pain and pleasure to merge. She closed her eyes to better concentrate on the task in hand and so did not see David position himself. The sight of her so close to climax yet desperately trying to hold it back had his cock stiff and engorged once again. He decided to take advantage of the fact that Kristy's ass was so temptingly presented. In one swift motion he pulled out the butt plug and plunged his cock deep inside her back passage. He could feel the vibrations from the device in her pussy start to act on his cock and he knew he would not last long. He started to thrust deep inside her, leaning forward to pinch and tease her nipples. Her breath was now coming in short pants as she struggled to control the demands of her body. Finally he felt he could hold back no longer.

"You may cum, slave" he said giving one final thrust and clamping down hard on her nipples.

Kristy screamed into her gag as she released all mental restrained and her body surged over into orgasm. As she was still shuddering in the aftermath, David released her bonds and gag. He pulled her off the couch and onto her knees in front of him.

"You may thank me for allowing you to cum by cleaning me off," he said.

Kristy dimly recognised this wasn't a suggestion, it was a command! She opened her mouth and took his dripping cock inside, using her tongue to completely lick him clean.

When she had finished, David commanded her to assume Position 3 once more. As Kristy placed her hands behind her head, David reattached the nipple clamps. She gasped in pain, but managed not to cry out.

"You may get dressed, slave" David said.

Kristy drew on her bra and sighed in relief as it took some of the strain from the weights hanging from her nipple clamps. It was to be short lived, however, as David reached out and swung them free of its support, letting their full weight exert itself on her nipples. Gingerly she put on her blouse and buttoned it up, trying to disturb the weights as little as possible. Instead of bending to put on her skirt, she crouched down and slid it up and over her hips. The she stood before her master awaiting his next directions.

"You will go straight home from this office" he commanded. "You will not visit the bathroom until you reach the apartment."

"Yes, Sir" Kristy said meekly, and taking the keys he held out to her, turned and left for her office. Once there, she gathered her jacket, laptop case and purse and left, taking the elevator down to the car park.

As she rode down she could feel liquid oozing from her ass and pussy and start to trickle down the inside of her legs. She shifted self-consciously, very glad that she was alone in the elevator. On reaching the car park she unlocked her car and climbed in. As she drove home the cars motion agitated her breasts, setting the weights attached to the clamps swinging. She gritted her teeth and tried to ignore the pain this caused her. She was also very aware of an increasing damp patch where she was sitting as her master's semen and her own pussy juices continued to leak out. All in all, she was relieved to insert the keys in the lock, and open the door of her apartment. Her feet were killing her. She had never worn heels this high before and having had to wear them all day was taking its toll.

She dropped her purse on the couch and put the laptop case on the coffee table, then made her way into the bedroom. She stopped short at the sight that greeted her. Gone was her comfortable king size divan. In it's place stood a double bed, complete with wrought iron bedstead. It wasn't, however, an ordinary frame. Set into the frame at various intervals were a series of sturdy metal rings. Kristy had a sinking feeling that she knew what this meant!

She removed her jacket and blouse before easing her skirt over her hips and stepping out of it. As she bent over to pick it up, her breasts hung down, increasing the pressure the weights exerted on her nipples. Then she noticed a large stain in the area where she had been sitting. It was obvious that the combined fluids had soaked all the way through the lining and seeped into the outer fabric. There was no way she would be able to send this to the dry cleaners, it was too apparent what had occurred. Instead, she walked to the kitchen and ran hot water into the sink, adding a liberal amount of washing detergent. She immersed the skirt in the water and left it to soak and returned to the bedroom to finish undressing.

She sat down on the bed, its firmness an unwelcome change from her comfortable divan. She removed her bra and bent over to roll her stockings down her legs. Once again the weights started to swing and without thinking, she kicked off her shoes whilst removing the clamps from her nipples. Immediately pain assaulted her from all sides and she fell to the floor crying out in agony. Her calves had cramped completely and the pain shooting through her breasts was excruciating!

David walked in at that moment and saw her curled on the floor in a foetal position. Her eyes were closed and she didn't notice his entrance. She did, however, feel it when she was yanked upright by her hair! David's lips thinned as he saw the clamps were no longer attached to her nipples. Taking firm hold of her hair, he pulled Kristy to her knees and forced her to look at him.

"Did I give you permission to remove the clamps before you left my office this evening, slave" he demanded.

"N-no Sir," Kristy stammered. "B-but I thought it would be alright to remove them now I was at home!"

"It is not your place to think, slave. It is your place to obey!" David told her. "Your behaviour has incurred a punishment. Now assume Position 1 immediately!"

Kristy placed her hands behind her head and made sure her knees were spread wide. David moved to the bedside drawers, which Kristy noticed now had locks installed. Taking out a key from his pocket, he unlocked the top drawer and took out a soft leather collar, set with several D-rings and a thick metal hoop. He also retrieved a padlock and moved back to where Kristy knelt. He efficiently placed the collar around her throat, slipped the hoop through the tightest setting of the collar and locked it into place. The collar now encircled Kristy's throat tightly, just short of choking her.

He returned to the drawer and drew out a pair of clover nipple clamps, holding them out to Kristy.

"Seeing as you saw fit to remove the last pair of nipple clamps, slave, you will put these on yourself and make sure they are securely in place!" David commanded.

Kristy took them from her master and attached them at the base of her nipples, wincing at the pain this caused. David then took out a larger pair of weights and held them out to her.

"Put these on!" he demanded.

Kristy looked up at him pleadingly, but his face was as hard as stone. Swallowing hard, she attached the weights to the clamps, crying out as each clamp tightened around her nipple from the pressure applied. Next David took out two thin metal chains, one short and one long. The short chain he strung between the two weights. He attached the longer chain in the centre of the shorter one and then ran it vertically down the length of her body. He passed it through her pussy lips and up across her ass crack, finally attaching it to the collar. There was no slack in the chain at all, putting pressure on and causing discomfort to her nipples, clit, pussy and asshole.

"On the bed!" he instructed.

Kristy obeyed, biting her lip as each movement caused the chain to rub against her pussy and ass and to tighten the clamps further.

David brought out two sets of leather cuffs and locked them around her wrists and ankles. He attached leather cords to each cuff and proceeded to bind her into a spread-eagled position, face up. He went to the bathroom and retrieved an item from the cabinet above the basin. He came back to the bed and selected a solid rubber butt plug from the range held in the bedside drawers. Pulling on a rubber glove, he opened the jar and smeared some of its contents over the plug, ensuring it coated it's entire surface. He slid a cushion under Kristy's buttocks and inserted the plug into her back passage. Moving swiftly on, he dipped out more of the jar's contents and inserting his fingers inside her pussy, made sure to thoroughly massage it in. He withdrew his fingers, dipped one final amount out and stimulating her clit with one hand, covered it with the substance as the little nub became engorged. He removed his glove, replaced the lid on the jar and walked out of the room.

Kristy lay still trying very hard not to move when she felt a tingling start everywhere that had been exposed to whatever had been in the jar. The tingling soon progressed to a warm sensation and was starting to become uncomfortable. It didn't stop there, however. The sensations increased until the heat was almost unbearable. Now Kristy was desperately trying to get away from the intense heat, squirming and writhing as much as her restraints would allow. Each time she moved she put more pressure on her nipples and caused the chain to rub against her genitals and asshole, which in turn aggravated whatever substance had been smeared onto them. By now she was weeping with frustration. She couldn't get away from her discomfort and could do nothing to relieve it. Finally she cried out.

"Please, Master, I can't bear any more! I'm very sorry for my actions and I promise never to do anything without your permission again!"

David left her writhing in discomfort for a further five minutes before walking back into the room.

"I trust my slave has learnt her lesson?" he asked.

"Yes, Master. Yes she has," Kristy sobbed.

"Very well," David said and untied her from the bed and eased the nipple clamps open slightly, allowing sensation to flood back. "You will crawl to the shower and wait for me there."

Frantic to be rid of the substance causing her so much discomfort, Kristy crawled to the shower as fast as she could, ignoring the pressure that was once again being applied to her breasts. She obediently waited for her master to enter.

"Position 2!" David barked.

Kristy immediately bent forward, placed her head on the floor of the shower and spread her ass cheeks as wide as she could. David detached the shower head and withdrew the plug from her ass. He filled the enema bag and inserted the nozzle deeply into her back passage. He released the clamp and let the water flow into her. In the meantime, he rinsed off the plug and when the enema bag had emptied, he withdrew the nozzle and replaced the now clean plug. He then turned on the shower and inserted the hose inside her pussy. Drawing on a rubber glove he inserted his fingers and swirled the water around, making sure to rinse her pussy out completely. Finally he turned the hose onto her clit and thoroughly rinsed that off too. When he was sure the rest of her was clean, he withdrew the plug and released the water it had held back. Kristy sighed with relief as the heat slowly faded away.

"Stay where you are and think on your disobedience" David told her.

"Yes Master," she replied meekly and remained in place as he left the room. It was perhaps ten minutes later when David appeared in the doorway. By now she had dried off and her knees were aching from the hard tiled floor of the shower.

"Crawl into the living room and assume Position 1, slave" David commanded.

Kristy obediently crawled into the living room and assumed position 1. As her head came up, she found herself looking at a pair of shapely legs. Raising her eyes, she came face to face with Sue Maddox. The woman looked at her with an amused expression on her face.

"I hear you're improving," she said, "although not enough by the looks of the state of you this evening!"

Kristy didn't know what to say. She had thought she would only ever come into contact with the woman at David's mansion in the Keys. Now here she was, looking completely at ease in Kristy's own home.

"I've been following your progress very closely, slave," Sue continued. "Did you like the video I left for you?"

Kristy's mouth dropped open in disbelief. With that one statement, she had effectively informed Kristy that she had been there in her apartment before. David entered.

"Ah Mistress S!" he said. "So good of you to visit. Have I thanked you for all your efforts regarding the apartment?" he continued.

"It was nothing," Sue replied. "All in a day's work, and I feel I did a good job, if I may say so!"

"Indeed! I am very pleased with what you've achieved. I'm especially happy with the clothing you provided. You've showed good taste and catered to my needs exactly!" David congratulated her.

"And is the selection of items in the drawer also to your satisfaction?" Sue asked.

"Yes. You've chosen exceptionally well, but I did notice there was one item missing," David said.

Sue frowned slightly as she tried to think of what it was she had missed, then looked up to see he was presenting a leather paddle to her. Her name, "Mistress S" was spelt out in studs embedded into the leather.

"Your first personal toy as a Mistress," David informed her, smiling. "Now I'm sure my slave wants to thank you for choosing her new clothing and toys, and is also keen to thank you for taking care of her new diet. I think you will see there is an improvement already!"

"Thank Mistress S!" he commanded Kristy.

"Thank you, Mistress," Kristy said hesitantly, still trying to come to terms with the fact that it had been Detective Maddox who had made all the changes to her lifestyle.

"That is not a good enough thank you, slave" David informed her. "You will thank your Mistress properly, as a good slave should do!"

Kristy looked confused but understanding dawned as Sue slipped out of her slacks and leant back against the couch, legs spread wide. She was obviously expected to eat her pussy! Kristy was torn between her natural dislike of pleasuring another woman and the thrill that swept through her as she remembered how she had felt bringing her mistress to climax previously. Her hesitation, however, had been noted by both master and mistress and they were not pleased.

Cyberdiva68
Cyberdiva68
601 Followers