Note: This story was dynamically reformatted for online reading convenience. -----Begin Header --------------------- Story: DRAFT - Jenny : Assistance Required Author: Max (max@cherishdesire.com - http://bit.ly/CherishDesireMax ) (c) 2008, 2009, 2010, 2011, 2012, 2013 Max (max@cherishdesire.com) Story Codes: MDom MF mast toys anal stretch Version Info: DRAFT - Revision 2 Note: You may distribute this story freely so long as this header is left intact with this disclaimer and author's name unaltered. Final versions of stories are published on Amazon.com (see Max's Author Page at http://bit.ly/CherishDesireMax ). Warning: If you are underage or this material is of no interest to you, then don't read it. Literacy comes with responsibilities. -----End Header --------------------- Author: Max ( max AT cherishdesire DOT com, http://bit.ly/CherishDesireMax , http://bit.ly/CherishDesire ) Title: DRAFT - Jenny : Assistance Required Universe: Tom, Jenny Summary: After six months of committing to training and working for Tom, Jenny's evolution can be seen in both her thoughts and capacity for functional submission. This story emphasizes some minor body modifications and very large toys. It also includes some indication of the caring developed between a dom and his sub. Keywords: Mdom, Mast, Anal, Dildo, Stretch, Large Toys Language: English Availability: PUBLICATION (Very Dirty Stories #8 http://bit.ly/VDS_008 ) -------------------------------------------- DRAFT - Assistance Required -------------------------------------------- written by Max -------------------------------------------- Mdom, Mast, Anal, Dildo, Stretch, Large Toys -------------------------------------------- It took about six months. In a way, she felt better for the time being spread out so long. No one seemed to notice the physical changes, and everyone just presumed she was kicking a long term depression. Looking back, she still felt a little bitter about the whole thing - but it was a price and she had paid it willingly. Jenny did her presentation that night with a good bit of confidence. The audience paid rapt attention to her discussion of societal structures as reflected in American literature of the 90s. Tom had coached through the preparation, and probably half the ideas really were based on his concepts of a social construct. But Jenny had filled in the blanks - people, behavior, examples, and the literature. It would be part of the masters she was now pursuing, and it felt good for people to be looking at her and listening and understanding. It hadn't started this way though. It had been a dark place and that had consumed her on and off for years. How Tom managed to be a part of that and everything else without shattering into pieces... well, then again, he did. But in a different way than Jenny, who would feel emotions welling up and then run over her like a train. Tom became part of the tracks, and then took the train to a destination as close to where he wanted to go as possible. Part of Tom wasn't quite 'right' because of that. Jenny pulled into the driveway of Tom's house. It was a nice place, a bit overly male with that typical too much electronics, too little attention to Kool-Aid spilled on the floor in front of the fridge. She had been taking care of the general household chores as well as handling his files and personal business for about one year. Tom now traveled a lot, but with Jenny to take care of the place he felt confident that he could do whatever the business required without worrying about things piling up and important messages being lost. Tom was home this week though, a bit sulky due to a lost client, and not quite as enjoyable as he could be. It didn't matter to Jenny. Either way, she always took a big swallow before opening that door. Inside, she was to be something both incredible and simple. Stepping through the door, the house was dark. Tom kept it that way in certain moods, and she knew better than to disrupt the shroud he had surrounded himself with. She quietly closed the door behind her, and set her things into the hidden alcove by the door. There was no note there about pending or current company, so she continued with the routine for when she was alone or with Tom in the house. Jenny took down a bag from the closet, and slipped off her shoes into its dark recesses. She took off her blazer and hung it, then removed her skirt and blouse. Jenny rested against the couch to remove her hose, slipping the garter hooks from them and then sliding them down her long legs. She was careful not to wet the couch, her ass and cunt were always lubricated and the oil-based lubricant would leave stains on the fabric. Jenny slid off her bra and garter belt as well, folding the package of undergarments and hanging the skirt and blouse while standing completely naked in the front atrium of the house. Once she had finished with removing clothing, it was time to address her breasts, cunt, and ass. Reaching into the leather bag, Jenny removed a studded bra. The kid leather formed stiff but supple cups to hold her breasts up, with a steel ring for each nipple to be pulled through. She slipped it around her torso and then gingerly pulled it up underneath her breasts. On the outside of the leather, small steel studs could be seen - they looked decorative. On the inside of the cups, however, they terminated in stars with sharpened teeth. Over the months her breasts had slightly toughened and taken on a slightly redder hue, as the flesh grew used to the slight piercing and cutting of those teeth. With the cups in place, Jenny wet her fingertips, and then used them to wet her nipples. The O-rings were adjustable, and pulling her nipples through required them to be slightly stiff - which the cooler steel always was enough to stimulate. But tightening the rings required some moisture so her nipple flesh wasn't too pinched by the twisting motion of the ring. The rings twisted into her nipples, and Jenny paused to take a deep breath and let the bra settle into its position. "One last step and I can fill my cunt," Jenny sighed to herself. From the bag she took a small suction cup attached to a pump. Placing the cup over her nipple, Jenny took the stroke handle of the pump into her other hand. The stroke handle was 5 inches long, with the ability to pull about a liter of fluid from a bottle. Jenny was only strong enough to pull it back about an inch before releasing the pressure. It pulled her some more of her nipple flesh through the now tightened ring, and caused the flesh to become swollen and engorged. Three one inch strokes were all Jenny could do on her own, but that was enough to make her nipples puffen, distort, and look unnatural. Setting the pump back in the bag, Jenny took out a plastic ziplock bag. From it she withdrew her lubricant, which was kept doubly sealed up to make sure it didn't seep on any of the leather. Then Jenny took out a 'sweat rag' and a larger bag for toys that needed cleaning. Jenny poured a small amount of lubricant into her left hand, careful not to waste any or spill it. She brought her hand down between her legs, planting her feet apart so her labia hung free. The lubricant felt cool against her hot lips and soothing as well. Standing like this, she could feel one of the rubber balls settling into position between her vaginal walls. She stroked the additional lubricant into her cunt lips and then into her cunt and clit. The rubber ball was a little bit smaller than a tennis ball, with a layer of latex so it could stay inside of her all day long. Reaching into her vagina with one finger, it was right there at the opening. She could slip a finger by it - having to be careful that her manicured nails didn't dig into her flesh. She could feel one of the other balls slightly over to the right of her cervix. The third was still pretty far up inside of her. Jenny slipped her finger out and ran her left hand over her outer lips again. Then she picked up the 'sweat rag' and placed it between her legs. Cupping it against her vagina, Jenny used her vaginal muscles to push down and out on the first ball. After ten hours, it was difficult to coax it out - first it slipped up higher into her cunt causing Jenny to lean forward as a mini-orgasm hit her from the feeling of the other balls deep inside of her. Then she relaxed, and pushed out as it slipped down toward her opening. The first ball dropped out almost as much as it popped - the pressure from her trembling vagina opened her up. She sighed mightily, feeling it momentarily stretch her open and then come out. The sweat rag caught the ball and the fluids that came with it. It was just part of the changes Tom had worked over Jenny - the constant wetness, the constant fullness, the constant sexual challenge. She already felt a combination of emptiness and the need to cum. Yet she could not set aside so much by just following the routine he had instilled in her. "Two more and then I can cum," Jenny whispered. She wondered sometimes if Tom knew - how much she had initially wanted to fight the changes to her body and how much she lusted after the same. He told her to do everything slowly and methodically, but Jenny always rushed through removing the second two balls. She ran her one hand over her belly and abdomen, stroking downward to applied pressure. Then Jenny leaned back against the door, jutting her cunt out lewdly, her legs apart and knees slightly bent. The cool feeling of the solid door on her back, and she pushed down like having a child. The next ball came with a little coaxing and effort. Then Jenny drove her hand into her vagina, reaching in to move the last ball toward the path out of her. It moved upward in response, so Jenny pushed it toward her cervix with her fingertips. Than drawing her hand out, Jenny again thrust her cunt forward, squeezing her ass cheeks together, and forced it out. Jenny closed the dirty toys bag with the three balls in it. She used a dry section of the sweat rag to blot out the fluids on her legs and lips, as well as some of the sweat on her abdomen. Her breasts felt distant, so she gingerly ran her fingernails over the tips of her nipples. That began the churning in her now vacant cunt for a good orgasm. Tom had compromised with Jenny early on. Anal plugs were too intense for Jenny to wear all day long. Besides there was a lot of cleaning, care, and maintenance required just to make them safe for an extended insertion. So Tom allowed Jenny to go without an anal plug during the day on three conditions: 1) As a rule Jenny could not have a full orgasm without a plug in her ass - excluding those occasions when he might allow for extenuating circumstances. Punishment was severe, so Jenny pretty much followed that to the letter - even reminding Tom on the occasions when he was taking her to orgasm but the plug had been left out. 2) Jenny necessarily kept her anus lubricated at all times, so if Tom should feel the need to utilize her ass it was readily available. Jenny had forgotten about this a few times and been caught. It had taken a few weeks to recover from the tearing that followed when Tom took it upon himself to all but fist her ass dry as a punishment and reminder. She definitely had not been able to sit or shit well for a while. 3) Jenny was obliged whenever the house was without guests to wear a plug for the first few hours of her arrival - its size guaranteeing her preparation for any activity that Tom should want to undertake. In exchange for the discomfort it might cause, Tom allowed Jenny one full orgasm whenever she put it in - no matter how frequently she did so in the house with him or just her there. It had taken Jenny three months to live up to the last condition. As such, several times she had been required to wear a small plug along with the balls over the course of the day. To put that in perspective, it had only taken Tom three weeks to train her cunt for his fist to penetrate deep into her. It had then only required an additional one month for her to comfortably wear two of the balls all day long. The third was still a bit of a challenge - as it always hung low in her vaginal canal so she definitely knew it was there all day long, and the other two pushed far enough up into her cunt that occasionally she suffered menstruation like cramping until she could move her body into a more comfortable position. But the plug... It was conical at the top - flattened a bit by the latex's own weight. Over a three inch long taper, the plug went form about a half-inch in diameter to a little over two and a third inches wide. Then it had a shaft about four inches long that swelled up to three full inches wide by the base. The next two inches were a reversed taper, resulting in a distorted pill like shape that end with a latex covered cord about two inches long and with a wooden handle. Jenny could put all nine inches in her cunt by placing the top taper against her labia and resting her weight on the plug. In fact, the balls were actually more of a challenge to put in her cunt since their spherical shape meant they lacked as much taper as the plug. Because of the reverse taper on the bottom, Jenny had to wear a leather chastity belt to hold the plug in her cunt. Otherwise it would come out as easily as she was able to put it in. In her ass though - that was a different story. After six months, Jenny's labia were easily four times as big when swollen, and with weights hanging from them they stretched a good three inches from her pelvis. But her ass was only more pliable. Tom had explained it to her at one point. He argued that a woman's vagina was intended for all kinds of things - fisting and large toys were only part of reaching a level of pleasure that could only be achieved with a cunt. Clitoral stimulation becomes an appetizer to the deep seated orgasms resulting from knowing your cunt is cramping in its spasms around a hand or incredibly large phallus. A woman's challenge is to learn how to handle the incredible tangle of sensations from her ass. Vaginal pain, tearing and piercing and even branding pales in comparison to just the first dry penetration of a woman's ass. And an orgasm triggered by the deep and full penetration of a woman's ass is incredibly more pleasurable when done right because there is so much more sensation before, during, and after. A clit may become painfully sensitive if overly used or crushed - a woman's ass starts that way. Jenny simpered at the thought, and took out the plug. When he had first talked about it, it made so much sense. His hand was buried in her cunt and her clit was screaming at every touch because it had been rubbed raw. She had signed an agreement to be his personal assistant, and housekeeper as need be - and then signed her body away under the terms that had led her to his door tonight. And now it was going to hurt and then ache, every movement would cause this incredibly huge thing to shift. All because he was right, in a self-serving way. There was no way to deny the sensations from her ass, no way to ignore the pain or fullness, no way to tune it out. For Jenny it was the overwhelming sensations that counted, anything else she could accommodate or tune out. Tom had shown her a path to blasts of white intense sensations she craved, while at the same time training her body to find everything else, from the balls to fisting, simple teasing. Jenny applied the lubricant which made the plug slick, making it harder to hold. Jenny placed the sweat rag on the floor. She took out a rounded football tee from the bag and set that on top of the sweat rag. It was the perfect shape to hold the slick plug up. Then Jenny used her fingers to lubricate her asshole and the flesh around it. Over the first six months her ass hole had actually moved down closer to her cunt - her ass cheeks pushed up and out of the way by larger and larger toys. Or maybe that was her imagination, she had tried to see in a mirror but she had no basis for comparison. Jenny set the slippery plug on its tee. It loomed huge in the limited light of the atrium. With a little dexterity, she squatted down, using her hands to guide her asshole to the top of the plug. Then Jenny placed one hand on the floor behind her, and used the other to pull on her ass cheek causing her anus to spread more open. The broad tip nestled against her ass, and as her chest heaved she didn't even notice the teeth digging into her breast meat. Jenny lost her balance a bit, causing her to lower her ass and weight on to the plug a bit too rapidly - it lunged against her ass, catching on her slippery cheeks and then lurching into her. Jenny yelped, and then grabbed it with her hand, holding it to her as her weight caused her to settle on to it. The taper began to open her ass up - too much too fast and she could feel the intensity of the pain shooting through her. Then his cool hands on her face - how long had he been watching her in the dark - the loss of concentration, and she slid on to it even further. Tom breathed on the tops of her breasts as he knelt down and placed an arm around her back. Tom set Jenny aright on the plug, and then began to nuzzle her breasts while murmuring to her. The shock from her nipples sent her cunt on fire. The pain from her ass was overwhelming, but only part of what was going on. Jenny felt suspended on a thread and then the thread became an animal plunging into her ass. She felt it move into her then, like every man who had fucked her bundled into one giant cock. She could feel their nails digging into her breasts, feel their teeth on her nipples. She swore under her breath as the first rages of orgasm came to her. Jenny wanted more in her, her cunt was so empty - and by driving down on the plug she felt it fill her cunt as well as her ass. It hit her tailbone and then lunged forward. Her cervix was being stroked from behind by the massive cock she was riding. The teeth moved to the top of her breasts. A hand gripped her clit and two fingers slipped into her cunt. Jenny felt like she was being ripped apart. The arm holding her forward was so strong, the hand on her ribs crushing them. Jenny screamed. The first orgasm was like a wave, and the following three or four orgasms left Jenny sprawled out on the floor. The wooden handle lay against her thigh as Tom picked her up and laid her on the blanket he had spread out over the couch. He cleaned up the mess with the sweat rag, and then put away everything for Jenny to clean later. Then he lay down beside her on the couch with her studded thong set on the floor for her to put on when she woke up. After all this time, Jenny had only taken the plug half a dozen times without passing out. Yet he had been there almost every time to scoop her up and make sure she was taken care of. He wondered what a woman dreamed of when the blackness came so immediately after taking such a thing, what kind of dreams did Jenny after driving her body to orgasm after orgasm until she passed out. Jenny stirred for a moment, feeling the monstrous plug buried in her rectum and distending her abdomen. She felt him lying next to her, and she felt safe. Her cunt was still spasming, and would continue to do so until the plug was removed from her ass. It exhausted Jenny but once the plug was inside of her, she had to consciously keep her vaginal walls clenching and trembling. The constant arousal kept the aching at bay, and had taught her how to cum whenever Tom filled any part of her. Besides, she was different now. The nine inch giant in her ass most nights, the balls in her cunt every day - Jenny was now fucked, thoroughly so, and she liked it that way. ------------------------ by Max ------------------------------------------------------- This DRAFT is provided for your enjoyment. Please support the author with your purchases and by promoting published stories. Max ( http://bit.ly/CherishDesireMax and http://bit/ly/CherishDesire ) This story is Published in Very Dirty Stories #8 http://bit.ly/VDS_008 Keep up with the latest Jenny stories: http://bit.ly/Ladies_Jenny ------------------------------------------------------- Pursuant to the Berne Convention, this work is copyright with all rights reserved by its author unless explicitly indicated. 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