Note: This story was dynamically reformatted for online reading convenience. -----Begin Header --------------------- Story: DRAFT - About Time (Jenny) Author: Max (max@cherishdesire.com - http://bit.ly/CherishDesireMax ) (c) 2009, 2010, 2011, 2012, 2013 Max (max@cherishdesire.com) Story Codes: MF vaginal anal toys 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 : About Time Universe: Tom, Jenny Summary: Jenny and Tom in their first sexual encounter. Jenny enjoys Tom slightly dominating her. The beginning of Tom exploring Jenny with large toys. Much of the activity occurs in a location exposed to the public. Keywords: Mdom, Vaginal, Anal, Dildo, Stretch, Large Toys Language: English Availability: PUBLICATION (Very Dirty Stories #11, http://bit.ly/VDS_011 ) -------------------------------------------- DRAFT - About Time -------------------------------------------- written by Max -------------------------------------------- Mdom, Vaginal, Anal, Dildo, Stretch, Large Toys -------------------------------------------- The world is a lonely cruel place. It has its moments of splendor, but they are washed away by tragedy and darkness. Jenny knew this. She knew it intrinsically. It was the sum total of her adult experience. But that didn't make it any better. So here she was. Standing at five foot nine, she was taller than these sniveling girls around the club. They didn't have anything better to do than blow off work and stay in bed. Of course, when you live with your parents - no worries about rent. A generation of rejects was around her - but all the better for finding some prey. She moved amongst them, smiling and chatting. She felt good with a couple of drinks inside of her. Then she saw him walking around the far end of the club. A couple of months, maybe three or more now with how time flies, he had moved up to another city. Job related stuff, and it sucked because she knew he was on the edge of interested. Still, he wasn't out and out prey - this one was a hunter. Jenny met him while a young friend of hers pursued him - well friend might be a strong word for the fat suckling bitch. He was hard on her friend, demanding that Shannon stand up for herself, critical of the things Shannon did like a second conscience kicking in when the first failed to due its duty. And when Jenny met him, she couldn't understand. The two went round and round - once or two times they broke off talking to one another. Shannon instigated some of it, but there was definitely an emotional charge between them. Then one night she came over with Shannon to his apartment. He laid out toys of a girth and length she hadn't had the pleasure of lately. In front of Shannon he had started to rub her back and then worked his way to massaging her breasts. He had thoroughly worked her up, and when Jenny and Shannon stepped out onto the porch to smoke - she had run headlong into harm. Shannon was crushed. The object of her affection had not only admonished her for months and emphasized that she needed to grow up - he then turned to her friend and gave Jenny all the attention she had been wanting. Jenny couldn't go forward with anything that night. It wasn't something she didn't want; it was an issue of the price to pay. Tom tried to explain it later, but he was cut off. As he moved across the bar she didn't care. She had dropped Shannon off that night, and then found a place to park. Digging through her car, she found a hairbrush. It was so small, so inadequate - the handle feeling like nothing as she drove it into her vagina. Stroke after stroke, she punished herself while thinking about the toys he had laid out, the way his hands had massaged her breasts, how her nipples had grown so erect and hard. She came and although it wasn't enough she had to race home and deal with it. Tom came up to her while Jenny's thoughts wandered. He had wanted to punish her, to feast on her. But Jenny would hunt him if he let her. He watched her corner and use a few other men, a couple of them too close to himself to think there was no threat to his own well being. Then she had moved on to other, hopefully more fertile, grounds. Her reputation had grown too big, and the men she had burned had said too much for her to find solace thereabouts. But she was a turn-on that Tom couldn't set aside. Jenny was tall and thin. Not so graceful as a dancer, but not as clumsy as a child. Her breasts were comfortable, they suited her well. And the one time Tom had really gotten to interact with her nipples - they were incredible. The expression "like pencil erasers" had been lost on Tom all his life. Then he met Jenny's nipples, and the expression came to life. They were long and narrow, but grew rigid and hard. Jenny had a narrow waist, and long legs. She dressed well - typically in skirts a bit 80ish which suited the places he most often saw her at. Besides, clothes weren't cut well for her figure. She had explained it to him, and it was clear once he thought about it. After all, Tom struggled to find jeans with a 32" waist and a 30" inseam for years that wouldn't crush his balls every time he moved. It only made sense that a woman of Jenny's height would find slacks unaccommodating and most dresses would be like tents around her thin frame. Jenny's smile and long blonde hair played well to her favour - she could pretend to be a bit ditzy while she was buzzing on alcohol. Of course it precluded her from being taken seriously - something that never ceased to annoy her. She was educated and fairly knowledgeable about the world in general - but no one beyond Tom and a few other people seemed to get to that side of her. All of this wrapped up in a package that loved to be fucked. Tom sighed heavily. What was he going to get himself into? Jenny said hello first when she knew he was standing there in front of her for a reason. Tom asked her whether she had been around much, since she had pretty much stopped going to the club a while back. Jenny asked if he was still living somewhere else. Tom paused at the insaneness of it all. Jenny frowned a little bit as his expression changed. Tom let out a deep throated chuckle, a bit evil but full of life. "Why don't we go some place to talk? You haven't been here often and neither have I - so we can skip it for a night and enjoy one another's company." Jenny felt anxious, but Tom was serious and seemed level headed. Before she could say no, Tom continued, "Come on - take a chance. It's been at least two or three months, and we've never had an opportunity to really sit and talk with you. You can leave your car here, or we can just take mine... I'm flexible. After being on the road all day, I just want to sit down and relax with a friend." With that Tom took Jenny's hand and squeezed it a little bit. Jenny was still a little shook when he began to lead her out of the club. He had asked after what she had brought with her, gathered it up, and began to escort her out - all in the wink of an eye. He knew her drinking habits, so she was vulnerable to the buzz she was feeling. Still, this wasn't going to be a back of the car quickie or a night out on the town. This was something different. "The Hilton I'm staying at has room service, we can order up some food. Are you ok to drive your car - it'd be easier if you followed me so you can go home whenever you feel like it. I don't want to make you to feel trapped because I drove us there." Jenny nodded, so Tom led Jenny to her car. Then he chuckled, and leaned down to her as she sat in her seat. With a kiss on the cheek he said, "I'm down a couple of cars, follow me up there." He walked off steadily. She was quiet. Inside of her she was churning a bit - it all was happening around her, and she knew what Tom as capable of. There was no doubt he could take advantage of her, but at the same time he made it her option to join him or refuse. He would give her any number of ways out of the situation, and allow it to be anything from a pleasant snack and chat to a torrid sexual adventure. All at her choice, her option. Perhaps that was part of the problem with Tom - she wanted it forcibly done to her, and by making her openly choose to do it that took some of the pleasure out of it. Tom pulled by her car and hopped out. Taking Jenny's hand into his own, he asked her to come over to his car for a moment. Jenny stood up and could feel the dampness between her thighs. Tom led her to his back door and asked her to get in for a second. She began to ask why, and he cut her off by running his hand over her ass and between his legs. "Just what I thought. You're all hot and bothered, and no one has taken care of you. I have something for you to wear while we're going to the hotel. It's up to you whether you ride with me or drive yourself. But I would rather you admit that you have no choice but accept this gift." Jenny tingled at his touch. His hand was cool like the night air, and against her flushed ass cheek it felt very soothing. When his fingers squeezed her lips and rubbed against her vagina, she almost fell down. And now, in front of her, in the car seat, a slightly larger than cock size plug sat there. Tom expected her to wear it. He expected her to climb into the car seat, and lie down and let him pull aside her panties so he could work it into her cunt. He expected her to let it fill her up and then to drive her car. Tom smiled at her; she could feel the warmth of it behind her back. He kissed her neck and said, "It's ok. I'll close up your car, and bring your purse. You don't have to drive. There's a blanket you can sit on and pull over yourself. Since you're riding with me, you'll be able to recline the front seat so you are comfortable." With that, he lifted her into the car, closed the door and walked over to her car to retrieve her purse and keys. Jenny sat steady. She was hot - true. She wanted to be fucked - true. She was a bit overwhelmed - true. She looked in the car around her and saw a bag lying on the floor. Leaning down to open it, she brushed against the plug beside her. It was soft and heavy - it rolled to her thigh. She hesitated, feeling it against her leg, and then lifted the bag to the chair. The zipper was open, and inside she saw some of the toys she had seen so long ago. The red jelly dick, two inches wide and ten inches long. The huge flesh coloured dong, maybe two and a half inches wide and easily twelve inches long. Another plug with the telltale control for a vibrator. A set of balls on a string, one string with three inch balls, another with two inch balls, five on each all coated with soft latex. She saw a large metallic vibrator, and then the car door opened behind her. "Oh. You spoiled the surprises. I have some time tomorrow and I wanted to go shopping for some new toys. So I brought these up. I felt that you could try them out and let me know which ones are keepers." Tom chuckled darkly. "I left the bags of ropes and leather harnesses at the hotel." Then Tom pushed Jenny forward, lifting her legs and forcing her on to her hands and knees in the backseat of his car. She struggled against his arms, but stopped when she felt his fingers begin to push and stroke against her cunt. "If you relax, it will be easier for your body to accept. I don't want to tear anything putting the plug into you." She sighed and leaned forward as his fingers rubbed over her clit. She could feel the way her bikini underwear cut into her ass as he pulled them to the side, his fingertips exploring her labia and clitoris. His fingers were cool, but quickly warming against her flushed skin. He stroked over her clit and began to rub her own juices into it. His fingers would dip into her vagina, and then spread the juices onto her cunt lips. Her clit was swelling and throbbing, and his fingers focused on it more and more. She was now wet enough for him to slip two fingers into her cunt, and she hunched back onto his hand every time he thrust into her. His thumb was grinding into her clit, and she could already feel her vagina contracting and pulsating. She wanted more, she wanted the plug inside of her, she wanted his hand inside of her, she wanted him to fill her... Tom was smiling. It was hard work, but she was very responsive. He enjoyed her body, and she would be excellent company. When they wound down, Jenny was more than capable of providing a good dialogue. Once she worked herself up, Jenny was incredible. She had hinted at it once before, the night she had seen his apartment and the toys. Something about how she was being fingered, and she was so turned on, and she thrust herself onto her companion's hand so hard, and she didn't even notice that he had worked his fist into her... Now Tom got an opportunity to enjoy being with her. Without asking, he cut away the sides of her bikini panties with a pair of scissors while pushing his two fingers all the way into her vagina. He pulled the cloth out of the way while he continued to massage her clit and cunt with his other hand. Her thrusts were only held in check by his constant pressure pushing her forward. Picking up the plug with his free hand, he judged its size versus the hole he was looking at swallowing his fingers. Tom grew hard as he realized it might not be big enough to whet her appetite while they drove to the hotel. She was much wetter and growing more and more open - more so than he imagined based on her slender build and hips. Jenny felt the plug being eased around her cunt lips. Her head was on the car seat, and her legs and stomach were sweaty from pushing back and grinding against the hand stroking her insides. The constant pressure on her clit felt like a cock head just ramming into her. His thumb was rolling her clit against her pelvis and it was swollen from the attention. Her cunt was on fire now, she could feel how his fingers not only pushed into her cunt but also explored it. He would move his fingers apart inside of her, the tips of his fingers stroking the walls of her vagina. At her cunt opening she could feel the knuckles of his other fingers: one knuckle firmly planted into her cunt from the pressure, the other moving between the flesh between her ass and cunt and her asshole itself. Crushing back against him, she could feel how strong he was. Not only did he keep her immobilized, when she thrust hard enough he was picking her entire lower body up off the car seat by her pelvis. It should hurt, but instead Jenny just felt the incredible urge to fuck against that hand harder. So she continued to push back, her stomach heaving as she also tried to put his thumb right on to her clit. Tom moved the plug around her cunt several times, allowing the tip of it to wetten. Then he took it to his lips and tasted her juices from it. Running his tongue over it, he lubricated it more with his saliva. Then he picked up Jenny off the chair with his hand, digging into her cunt and clit at the same time. Placing the plug alongside his hand and just outside her cunt, Tom then let Jenny do the work. Once he set her down on the car seat, Jenny's knees gave her traction. Letting his fingers slip out of her, Jenny instinctively bucked toward them, looking for them. Tom's fingers were replaced by the plug, and Jenny impaled herself on it with her backwards thrust. She gasped as she felt the cool latex plug slide into her. Jenny leaned forward trying to get away, but found Tom had both her thighs in one arm, cradling her pelvis. His other hand was driving the plug into her, and it was already wedged between her lips. He rocked it back and forth, and the plug felt like a huge cock head just pounding away an inch inside of her. Jenny began to rock with it, feeling how it was stretching her cunt. Tom sensed her motion and moved his arm from holding her thighs, so he could begin stroking her clit again. Jenny felt his fingers hit her clit, and could feel how he was stroking her lips all around the plug filling her cunt hole. She could only barely feel the tip of it inside of her, all of the pressure and sensation came from her cunt lips as they strained against the latex. Jenny began to push back, at first in time to the rocking. As Tom found her clit and exposed it to his fingertips, Jenny began to buck against the plug. Tom watched as his arms shook from the pressure he was applying to the plug. There was no risk of tearing her open, just an issue of keeping enough pressure on so Jenny could feel the urgency of taking the plug into her cunt. For five minutes he had been fucking her in the parking lot, and he wanted to move on to a safer place. Luckily it was about the middle of the night, and there wasn't much activity. A few people knew what was going on, but wisely kept it to themselves. They'd go back and gossip about it some other day. His fingers were stroking her clit, one on each side so it would encourage her to grind back and forth over them. The plug was only about two inches in diameter - once it was in, it would stay in, but the key was the sensation of the last and widest part entering Jenny's vagina. She would like it and want more - and since it was a plug, the depths of her cunt would be largely untouched by it. Tom wasn't sure if Jenny was into anal penetration. So as a compromise he had intentionally picked up a small vibrator. Now he began eyeing it for other possible uses. As Jenny continued to buck against the plug, he took his hand off her clit and picked it up off the floor. He turned it on and quickly held the vibrator against her clit. Jenny felt the spasm rise through her. Like electricity, the vibrator became a scream inside of her head. She felt her clit exploding, her cunt shaking, the tremors making her legs and arms weak. She collapsed forward, only to let a moan out as the plug slammed into her. Tom was pulling and pushing it into her now, like a cock. Each time it went a little deeper, and she wanted it so bad. The vibrator felt cold against her clit, but the sensation was like being on a motorcycle and having the engine gunned over and over. Jenny was cumming freely now, and the plug was slamming into her. She began to push back again. Now it was with a purpose... Tom felt the shift as Jenny came. First she went soft and limp on him. To keep her going, he began to out and out fuck her with the plug. As it drove in and out of her cunt, he teased her clit with the vibrator. Her soft cries told him she was cumming more and more. Then she took him by surprise. She suddenly drove back at the plug as he thrust it into her. His arm shook at the force. The plug itself was pliable, and with how hot her cunt was it was beginning to reshape itself under the pressure to penetrate her. Her thrusts combined with his became a quick rhythm, and after four strokes the plug sunk past her cunt lips and into her as far has his knuckles would allow. Jenny felt the incredible stretch that allowed the plug to pass into her, and then felt the wedge like head of it deep in her cunt. Tom's knuckles slammed into her labia and the vibrator fell from her clit. Now she was fucking it, the whole plug. She felt Tom pull it out a little bit - her lips being stretched the other direction, and then she and Tom thrust together, and it slammed home. Tom's voice was edgy - "Count the strokes out loud - let's see how many you can take." Then he began to pound the plug in and out of her in earnest. The first couple of strokes she was too breathless to say anything. Then she felt his hand slap her ass. "Each stroke you don't count will be punished later." Now she really felt how strong he was, and her ass stung. "One... two... three... four... unh." Tom had shifted picked up the vibrator again, but this time he placed it right on her asshole. With the plug now freely coming all the way out and then all the way back into her - Jenny felt wide open. Her cunt ached from the punishment, but she was all but cumming again. And the counting was so hard. "I have another plug for your ass when we get to the hotel. Don't tempt me to just shove it in to you now because you're too lazy to count. I want to hear your voice as you feel the plug pushing into you. Five more strokes and then we're going to get out of here to go someplace more private." Jenny gasped for air. The plug had made a mess out of her: she was soaking wet and the wind was all but knocked out of her. "One" she counted while trying to suck in a breath. "Two" came out as sigh. "Three" came out as a ragged whisper. "Four" and she felt the vibrator on her asshole. It was pushing into her. "Five!" Jenny shrieked as the plug slammed into her cunt, Tom's knuckles cracked against her pelvis bone, and he slipped the vibrator into her ass with his other hand. Then she came to Tom as he swiftly pulled her from the car seat. Pausing only to open the door, he set her in the front passenger seat. She was in shock, and the cold air had sobered her up in an instant. Tom buckled her in, closed the door, and jogged to his door. Getting in the car, he began to drive away. Once they were out of the parking lot and up to the first stop light, Tom looked over at Jenny. She was sweaty and mussed - and he reached over to stroke her hair from her eyes. Jenny could feel the whine of the vibrator in her ass. The plug was wedged into her, and sitting on them both meant that she could feel everything. Tom was talking, but everything was a bit out of focus. He guided her to lean the chair back, and she did as his hand took hers and put it on the chair release. Then he put the bag of toys in her lap before pulling away from the stop light. "There are several items in there. At the hotel there is a small doorframe that can be used to create a vertical rack. I was thinking of tying you up a bit - but I don't know that your legs can handle the strain. So, the other alternative is that I take you to the shower, wash you, and then lay you out on the bed." Tom paused while they got on the interstate. Once he had merged into traffic, he continued. "I want to know what your limits are, but I want to do this safely. I've drawn up a one night contract for you to look at. It includes safety words and an opportunity for you to allow me to do anything to you so long as it is not permanent and it is in the pursuit of pleasure. It requires, due to our mutual circumstances, a certain amount of silence." Tom ran his fingers over her face. Reclined like this, Jenny was feeling the plug worrying at the aching inside of her cunt. But she felt good; she felt fulfilled. "Is that something you would be interested in talking over while we have a snack?" Jenny quietly answered, "Yes." She felt like she wanted more. Tom started on the casual conversation that would get them to the hotel. "Well the Far East economy looks like it's going to collapse. Might be a good year to go overseas if the dollar stays strong in Asia. Have you thought about going to visit Japan?" ------------------------ brought to you 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 #11 http://bit.ly/VDS_011 . 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. Non-commercial re-posts to web or similar venues are allowed provided copyright information remains on the re-posted story. Please do not delete the copyright information. No commercial reprints are authorized. --------------------------------------------------------