1 comments/ 45766 views/ 2 favorites Story of Jenny Ch. 01 By: rick_oh Part 1 - Friday Night With Jenny The sound of talking, laughing, and music filled the room at Jenny's house. As happens during every party, there was soon a lull in the conversation, and Jenny called to him. When he was by her side, she told him, in front of the four other women in the room, "I want you to strip. Now." He looked at her questioningly, and she clarified. "Take off your clothes - right here, and right now." The atmosphere became quiet except for the music in the background. Somewhat nervously, and knowing that he had better do as Jenny commanded, he started to undress in the middle of the living room, in front of all her guests. First he took off his shoes, then socks, followed by his shirt, and then, rather shyly, trousers. At Jenny's insistence, he had shaved his body from the waist down, including pubic hair, and was quite self-conscious of his appearance in front of Jenny's guests. Dressed only in his briefs, he looked at Jenny. "Everything!" she commanded. Looking at her smooth bare legs and the short white skirt she was wearing, he slid his briefs down and stepped out of them. "Put your clothes over there," she ordered, pointing to a corner of the room. He bent down, picked up his clothes, and placed them on the floor, then arranged them neatly. "Come over here now," she commanded. When he was by her side again, she said to her guests, "I'm going to give him a good caning." There was a hum of interested hushed exclamations from Jenny's guests. He had an idea that she was going to discipline him when she told him to take off his clothes. This was to be his first time with an audience - and not just one other person, but four of Jenny's friends. her pronouncement that she would use the cane sent a shudder through him since he was familiar with her technique of drawing the caning out to a very lengthy session. He saw the wide-eyed look of excitement on the other women's faces, and looks of anticipation. He knew that Jenny was feeling very sexual at this point, although she showed none of it. She grasped his penis with her firm fingers, saying, "He usually is quite hard by this point, but since he has an audience..." Jenny felt the member growing in her hand as she subtly but firmly manipulated it. All the while he was becoming more embarrassed. "He must keep himself shaved from the waist down. I want him that way for his enemas too," she said to his obvious discomfort. "It's time to start now," Jenny announced. "Go get that chair and bring it over here in the middle of the room." She had him place the chair so that his bare bottom would be facing his audience when he bent over the back of it for his caning. "Go get the cane!" Jenny ordered. He did as she ordered, being gone about a minute and, bringing the thin whippy rattan cane, handed it to her. More interested sounds from the female audience. "You know what to do now,", she told him. With a sigh of resignation, he bent over the back of the chair and waited. "You had better STAY in that position now," she urged as she lightly tapped the cane against his bared, shaved buttocks. Jenny stood to one side, tapped his buttocks a few more times, drew the cane far back over her shoulder, and placed a vigorous, whippy stroke across the center of his bottom. He quickly drew in his breath and twisted slightly from side to side, obviously trying to avoid any vocal manifestation of his predicament. A few seconds later, Jenny drew the cane far back again, and placed another red-hot stripe immediately next to the first one. A whispered groan escaped involuntarily. A third stripe, immediately to the other side of the first one, evoked a closed-mouthed "mmmmmgph!" from him, and some more writhing. Addressing the other women, Jenny stated, "He knows to stay in position or he will get more after we're done. It took a lot of practice and many sessions, but now he can pretty much manage, especially since the consequences are not pleasant -- for him." With that, she delivered three more expertly-placed stripes on his buttocks, to the tune of urgent groans escaping his clenched teeth. Jenny's guests were in awe of the entire scene before them. They knew that Jenny's expert precision in placement of the cane strokes was due to extensive practice, much of it no doubt on the bared buttocks of the male now receiving her attention. By the time Jenny had placed ten strokes on her charge's bottom, it ceased to matter to him that four other women were watching, and he began to vocalize his predicament. Of course, Jenny knew this and thoroughly enjoyed the situation. He also had commenced to respond to each vigorous stroke with undulations and agonized writhing and kicking, all the while staying in the bent-over position commanded by Jenny. He pleaded urgently, knowing that she would take no heed of his immediate pain. He begged her to stop, to stop only for a moment, knowing that she would not stop until she decided to stop. "Not so hard," he pleaded, knowing that she would use the whippy cane as hard as she wanted to use it. He knew that his pleadings, and the phrases which were urgently escaping him, were sweet music to Jenny, and were getting her passionately aroused. "I like it when he wiggles and squirms like that," Jenny said to her wide-eyed guests. He knew that the more intense the discipline now, the more intense his later reward would be. This knowledge was no consolation to the most intense desire for any kind of relief from the spirited and energetic strokes with which Jenny was staging her show. After twenty such strokes, Jenny paused. She allowed him to stand up now, but told him to stay where he was, while she poured coffee for her guests and visited with them for a while. Excusing herself for a few moments, she went to the bedroom and slipped off her panties. Then, again picking up the thin, whippy cane, Jenny coyly whispered in his ear, "I don't have any panties on now, and I'm so hot," and got back to her task in front of her enthusiastic and wide-eyed audience. The sound of the cane making contact with his bare skin filled the room. His intense writhing and kicking, and the ever-increasing stridency of his pleading followed each stroke like clockwork. Jenny was now placing vigorous strokes diagonally across his buttocks, each stroke on top of and transversing previous strokes from the first part of the session. This considerably added to the punishment effect. She was becoming increasingly aroused with each stroke she delivered. She reflected on her ability over time to considerably extend his limits of endurance. The whipping continued... Whishhhhhh-smack! "Oh Jenny, Jenny, pleeeeease no more!" Whishhhhhh-smack! "Owwwww! Aaaaahh! Stop! Stop just for a minute, please!!" Whishhhhhh-smack! "Jennnnnyyyyy! Noooo! Oh, Jenny, no more!" Whishhhhhh-smack! "Please, Jenny, stop! Please please please!!" Whishhhhhh-smack! "Aaaaahhh! Stop! Stop! Please stop now, just for a minute! Oh, Jenny, Ohhhh!" Whishhhhhh-smack! "Owwww! No, Jenny, no, please!" Whishhhhhh-smack! On and on it went, each cane stroke bringing forth an entreaty to stop. On and on it went, with Jenny near ecstacy from wielding the cane so skillfully and with such an effect as she was seeing tonight. The guests were obviously very aroused, some of them squirming, others watching raptly with their knees and legs pressed firmly together. She stopped, but did not indicate that it was finished. As she expected, he stayed where he was while her excited guests made small talk and prepared to leave. A little while later, when they had gone, Jenny again picked up the cane and started whipping his bared, striated bottom anew. While she did this, she placed her free hand under her skirt and treated herself to several orgasms. More inexorable strokes from the expert and beautiful dominant Jenny, and more twisting, kicking, writhing and supplication from her charge. When she sensed that he was truly near the end of his endurance, she stopped and told him to come to her. He was grateful, of course, though he still intensely felt the pain from all the strokes Jenny had excitedly imparted to his backside. Jenny sat down on the sofa. He slowly stood up, went over to her and kneeled before her. Jenny's eyes were wide, her lips parted, and her breathing full. She hiked up her skirt, spread her knees and he gingerly approached her creamy sweetness with his mouth. After he treated her to more orgasms, she invited him in. As was custom after such an intense session, after his first release, she took him to the bedroom and expertly brought him near orgasm several times, finally allowing him release and restful slumber. Throughout the night when they were awake, he found that whenever he would touch Jenny, she was still in an aroused state from administering the whipping. They both found intense pleasure in the moments that would follow, then they drifted off to sleep again until the next awakening. The Story of Jenny Part 2 - How It Began Jenny and her boyfriend had spent a quiet evening at her place. She was giving him a backrub, and they were talking about various things. His reply to one of her statements was "That's the pussy way of doing it." Smiling, she playfully smacked him on the rear with her hand and told him, "I'm going to smack you one every time you say that word!" "Pussy, pussy, pussy, pussy, pussy!" was his response. "Oooooohhh!" Jenny exclaimed with mock anger, and gave him five good hand smacks on the rear end. They both laughed, and he turned over and reached out for her. She noticed that he was sporting a firm erection and said, "You must like that, don't you?". "Pussy, pussy, pussy!" he said, chuckling. "Well, maybe I should take you over my knee and give you a good spanking," she responded with a mixture of bemusement and authority as she sat on the edge of the bed and playfully pulled him over her lap. Feeling more and more turned on by what was happening, Jenny delivered several hand slaps to her boyfriend's bared backside. They both laughed through the spanking. He repeated "pussy" several more times while he was over her lap, and she obliged by extending the spanking each time. Jenny could tell that he was enjoying what was happening, and she certainly was enjoying it. The spanking was followed by an intense lovemaking session. Reflecting on the situation later, Jenny was surprised and perplexed at her own emotional reactions. She had intensely enjoyed acting authoritatively and giving him the spanking. She was also delighted that he appeared to fancy her role as well. On the other hand, she was somewhat disturbed that she got pleasure from giving the spanking. She also experienced a combination of excitement and confusion, knowing that she wanted to give him more spankings. Jenny decided to watch closely for signs of encouragement. She also vowed to herself to learn more about administering more intense forms of spanking, and about the various instruments used in the scene. To this end, she browsed bookstores for literature on the erotic aspects of spanking, and selected material in line with her goals. She found that she did not go in for the boots and leather B&D scene, preferring instead the traditional discipline setting. During some horseplay with her boyfriend a while later, she found herself reacting to one of his exclamations by saying, "You need a good spanking for that!" In the playful struggle that followed, Jenny got him face down on the bed, and with one hand firmly pressed on his lower back, she gave him several hard smacks on his buttocks. Chuckling, he taunted her, "Can't you do better than that?" Knowing she had been challenged, and delighted with the progression of events, she excitedly told him, "I'm going to remember that! The next time you come here I want you to bring a paddle... A good, hardwood paddle. Then I'll try it out on you." A few days later, after Jenny reminded him that she meant what she said about the paddle, he came over to her place and showed her what he brought. It was a hardwood paddle that he had fashioned from a cutting board, sanded smooth, and applied several coats of semi-gloss clear varnish. It was a masterpiece of perfection. "It took an hour and a half to saw that wood into the shape I wanted it," he proudly said as he presented the wooden implement to her. Jenny placed it on the coffee table and they chatted for a while. A little while later, Jenny brought up the subject that they had thus far skirted around: spanking. Gingerly, she conveyed in the conversation that followed that the thought of spanking him aroused her greatly, and that she hoped that he would be willing to experiment. He mentioned that he would not have put as much effort as he had done into constructing the paddle if he were not turned on by the prospect. He asked her when she was going to "try out" the new paddle. With a coy look, she simply said, "later." Around 9 PM, they were on their way to bed, and Jenny stripped to her underwear. She turned to him and said, "Bring me the paddle. It's on the coffee table." When he had fetched the paddle and handed it to her, she said brusquely, "Get completely undressed." While he was undressing, Jenny dragged a kitchen chair into the large bedroom and placed it where she had previously decided would be the best place for it. "Okay, now. Come here and bend over the back of this chair. I'm going to give you a good paddling." Admiring the paddle that was in her hand, she stated, "This is a fine paddle. I'll bet I get lots of good use from it." Whe he was in the expected position, she applied a few perfunctory swats, and then started in with considerable energy. The paddle, when applied with strength, imparts a most urgent sensation to the person receiving it, rendering it very difficult if not almost impossible to stay in position, or at least to receive the strokes without squirming. The strokes hurt much more than expected. Because of this, he visibly struggled to stay in the mandated position. He squirmed, kicked his feet, and otherwise wiggled, performing a spontaneous "dance under punishent" that Jenny found most provocative, especially when combined with his vocal reactions to her ministrations. Adding to her arousal was the sound of the paddle as it made contact. Jenny sensed when he was about to get out of position, and in reaction she slowed the pace of the strokes. Other times she gave him verbal encouragement to stay in position, either in an authoritative tone, or gently, with cooing overtones. When Jenny was at a feverish stage of arousal, she stopped the paddling, quickly got out of her underthings and led him to the bed, where they passionately quenched one another's heightened desires. Over the next few weeks, Jenny used the paddle several times on her willing recipient, with the result that they both experienced a heightened arousal with each other. She varied the scenario from time to time, having him lie across her lap, or telling him to lean across her desk. Jenny wanted to delve further into the scene, and acquired two leather straps, one with a wooden handle, and another, called a Scottish tawse, which, at the business end, was split into two "fingers". When she was alone, she practiced with the straps on a small pillow tied to the back of a chair, until she developed confidence in her aim and follow-through. Jenny administered several strappings to her boyfriend over the next few weeks, interspersing them with somewhat severe paddlings. She especially liked the way she could use subtle variations in technique with the strap to achieve differing results, from an explosive cracking sound to a quieter but more painful-sounding snapping sound. She varied the intensity of the sessions, administering some moderately severe strappings and some which were quite severe and prolonged. It was during these very severe strappings that Jenny found that she could extend her boyfriend's overall endurance from time to time. He often needed strong encouragement to stay in position during these endurance-extending sessions. Jenny provided this encouragement in two different ways. One way was positive words of encouragement, telling him that he is capable of enduring what she was giving him, providing sensuous touching between sets of strokes, and the like. The other way was to warn him of rather severe consequences if he did not stay in position, promising extra strokes on top of whatever he was destined to endure. It happened that he did get out of position on a few occasions and Jenny, true to her word, always delivered what she promised. It took just a few instances of those severe consequences for him to develop the self discipline required to never get out of position when he recieved discipline from Jenny. Jenny found that the full sized paddle was too clumsy to administer an over-the-lap spanking to her boyfriend, so she read some spanking literature about the wooden hairbrush. She located a source and obtained a flat, wooden, hairbrush of just the right size - not the overly small kind which are more commonly available and not suitable for the intended purpose. When Jenny first used the hairbrush on her boyfriend she immediately liked the sense of intimacy and contact that came from having him across her lap. She could instantaneously feel the effect on him from each swat of the hairbrush, and she became aroused from his squirming and wiggling as the spanking progressed. Jenny gave several hairbrush spankings to her boyfriend as the weeks progressed, some of them quite lengthy and severe. Occasionally she used the strap for a while after a good hairbrush spanking. As always, they were both very turned on by the time the spankings were finished, even when he sincerely and genuinely begged her to stop during the chastisement. These experiences led Jenny to develop an insight into the psychology of spanking in relation to the discipline that she administered to him. Her most profound insight was that she should accept herself, with all her fetishes, kinks, and fantasies, and accept the same in her boyfriend. That insight led to Jenny being at peace with herself and no longer disturbed that she became sexually aroused from administering spankings. The sessions became more imaginative and sometimes more severe. Jenny liked the idea of occasionally having other women witness the discipline of her boyfriend, and arranged some sessions including some of her carefully chosen friends. The Story of Jenny Part 3 - Jenny Has Help Jenny was talking to her friends Beckie and Vicky about why and how she disciplines her boyfriend. After their visit on a Friday night two weeks ago, in which they watched him receive a very severe caning, they had each individually approached Jenny and asked her if she would tell them more about the scene, and if they would be able to get some practice under her tutelage. Jenny, of course, was happy to oblige. She told them how her disciplining him was a turn-on to both of them and how it dramatically kept their lives, romantic and otherwise, interesting. She invited them to participate in a discipline session, and they readily agreed. She described the forthcoming scenario. "Before the session, I'll cut up a few sheets of paper into little squares. Then for each little piece of paper I'll roll a pair of dice and write down the number on the paper, fold it up and put it in a jar. When one of us is spanking him, another of us will draw numbers out of the jar and announce the number. He'll get that many strokes. How about Saturday at eight? Sound good?" They enthusiastically agreed. Jenny arranged for Beckie and Vicky would show up a little before eight. Jenny's boyfriend would already be there at that time, but would not know details about the session until the other women arrive. Story of Jenny Ch. 01 When Saturday evening came, Beckie and Vicky arrived as scheduled, and Jenny provided refreshments to her guests. After a few minutes of small talk, Jenny took the opportunity to direct the evening's activities and announced to her boyfriend, "I've asked Beckie and Vicky to help with tonight's discipline session, and they're also going to help with giving you the hairbrush and strap. I offered to give them some training." He saw a look of excitement and anticipation in the eyes of the guests, no doubt due in part to their recollection of the severe caning that he received from Jenny two weeks ago. Jenny turned to him and ordered, "Let's get started. Get completely undressed! Now! Everything!" He knew better than to delay, so he quietly complied. While he undressed, Jenny brought out the jar full of numbers to be drawn. After he was totally naked, Jenny pulled one of the kitchen chairs into the middle of the living room, sat down, and pulled her short skirt up higher. "It's important when you're giving over-the-knee punishment, that your lap is completely level, like this," she told her friends as she spread her feet apart while keeping her thighs close together. Turning to him, he ordered, "Now get me the hairbrush." When he handed her the instrument of punishment, she motioned for him to position himself over her lap. When he was positioned to her satisfaction, she told her friends, "Most of the time I alternate between each side of his bare bottom, and I choose a slightly different place each time, although I confine all the strokes to the buttocks. If he interferes, I may give him several HARD strokes in succession in the same place. I had to do that a lot when I first started to spank him, but as you saw from a couple of weeks ago, he has developed some self-discipline." "Beckie, why don't you draw the numbers from the jar for a while." Beckie withdrew one of the folded papers from the jar, opened it, and announced, "Eight." Jenny started the discipline session and proceeded to pound away eight times. Each stroke reverberated through the room as Beckie and Vicky watched with wide-eyed fascination. "Next one, Beckie!" "Five!" Whap! Whap! Whap! Whap! Whap! "Next?" "Twelve!" Jenny proceeded to administer the twelve hard strokes in an inexorable cadence. Her boyfriend started to react with an "Ohh!" or an "aaaahhh!" to some of the well placed strokes. "Next, Beckie? If the total comes to less than ten, add the following number." Beckie drew a number, and then another one. "Fifteen." Fifteen more strokes landed to the accompaniment of his vocal reactions to the mounting pain. And so it went until Beckie had tallied several more numbers. "Your turn, Beckie, and Vicky will tally for a while. We have a ways to go, so I want to give each of you a chance at both the hairbrush and the strap." Beckie took her place in the center of the living room, positioned herself so that her lap was level, put her knees together, and, pointing to her lap, said to him, "Get in position now!" Jenny handed the hairbrush to Beckie and asked Vicky to draw from the jar, and if the number is less than ten, add the next number to it. Vicky drew two numbers and announced, "fourteen." Beckie slowly started to paddle his bared bottom with the hairbrush. After a few strokes, Jenny interjected, "Harder, Beckie! Put some energy into it! Start over from one." Beckie needed no further encouragement, and took to her task naturally, getting the same kinds of reaction from him as Jenny got. She beamed with pride at the end of the volley of swats, and waited for the next tally. After she had administered over sixty swats, Jenny had Vicky take her place. Vicky was a fast learner, having observed both Jenny and Beckie, and when she heard the number eleven, started to methodically and energetically impart the strokes to his already reddened buttocks. Jenny commented, "That's good, Vicky!" After Jenny drew several more numbers, Vicky administered close to seventy five swats to a squirming male. Jenny announced, "Okay, now it's time for the strap!" Jenny ordered him to fetch the leather strap. She repositioned the chair so that when he is in position to receive the strap, his bared buttocks would be facing toward the women. When he returned and handed Jenny the strap, she bent him over the back of the chair and told her friends, "He has to stay bent over the chair until and unless I tell him he can get up. If he gets up during the strapping, he gets several extra strokes at the end of the session for each time he gets out of position. He can yell, and kick, and wiggle, but he must stay bent over. As you might guess, he has had to get extra strokes many times during the first couple of months. But his self-mastery and my encouragement has pretty much taken care of that. I still like to try to extend his limits of endurance from time to time, and I know he has a very difficult time staying in position then." "Stand almost to one side, like this. When you give the strap, always follow through with the stroke, like when you're playing tennis. Don't stop the swing when it hits, keep on going. Vicky, would you draw, please?" "Twelve." "Okay, now, watch the follow-through..." With that, Jenny gave him twelve ferocious strokes with the strap. He gave an exclamation with each one. "Next, Vicky?" "Nineteen." Jenny delivered the nineteen strokes vigorously and rather quickly. He had begun to wiggle and occasionally plead with Jenny. Vicky drew a couple more more numbers, to the accompaniment of the sound of the well-used leather strap striking naked skin, and his more urgent pleading. "The hairbrush warmed up and tenderized his butt for the strap," stated Jenny. "I like to give him the hairbrush or paddle first, if I'm going to use the strap later - it makes it more interesting. Your turn, Beckie. And don't forget the follow-through." Beckie took the strap from Jenny, paused a moment, and then asked, "Jenny, do you have a little bell? A little brass one, like the kind that you'd use during the holidays?" Jenny, looking puzzled, slowly answered, "Well, yes, do you want to have it now?" Beckie nodded and Jenny went to look for the bell. A few moments later Jenny returned and handed the bell to Beckie, along with a length of string. "Stand up, now, and turn around," Beckie commanded the male who was positioned for the strap. When he did so, she further instructed him, "Spread your legs apart, and put your hands behind you... wider!" When he did as instructed, Beckie proceeded to tie the bell to his testicles so that the bell hung down a few inches below his testicles. With the effect of Beckie's expert fingers handling him, along with the heat on his backside from the hairbrush spanking and the recent strapping, he quickly developed an erection. Beckie and the other women smiled knowingly. "Into position again," she commanded. "Now I'm really gonna ring his bell," exclaimed Beckie, much to the delight of the other women present. She picked up the strap, said, "I'm going to enjoy this", and took her position to one side of the soon-to-be recipient of her attentions. "The count, Vicky..." When Vicky announced the count for the first number, Beckie went right to work, giving vigorous, forceful, well-placed strokes of the strap on his bared buttocks. Each time she delivered a stroke the bell, which was tied to his testicles, clanged. After several strokes, he gave an exclamation, no doubt realizing that Vicky would take her turn after Beckie was through with him. "Next?" "Fourteen!" The process went on for count after count, stroke after stroke, without Jenny calling a halt to Beckie's administering of the strap. While he didn't know how long Beckie would wield the strap, he was certain that it would be however long Jenny wanted her to, and would not end one stroke sooner. To him, Beckie's attentions seemed to go on forever; to Beckie, the session was a magnificent turn-on as she felt the tingling dampness of her vaginal area being lubricated from the excitement of her participation in his discipline. Her recipient was writhing now with each stroke, causing the bell to clang almost constantly. After considerable time with Beckie wielding the strap, Jenny told her to stop. Beckie stopped, her eyes wide with excitement. Vicky, anticipating her turn wielding the strap, got up and handed the jar to Jenny. Jenny announced, "Vicky, I'm going to tally up several numbers in advance, and then you can have at it for the entire number of strokes. Jenny then added up the tally for item after item drawn from the jar, and announced to Vicky, "Fifty six. Don't forget to follow through." Vicky, with the strap in her hand, looked at the reddened buttocks of the male, and announced to him, "Don't think for a minute that I'll be easy on you because the others got to you first. I'm going to treat this as a fresh new strapping for you, and I'm going to thoroughly enjoy it." Vicky started in on the already strap-ravaged bared buttocks of her male charge, delivering vigorous swats with a perfect follow-through. His reactions to her ministrations showed that her efforts had the intended effect. *smack!* "Ow! Ow! Oh that hurts!" *smack!* "Ohhh! Not so hard!" *smack!* "Oh please no more! Stop just for a minute!" *smack!* "Please, Vicky, PLEASE!!!" *smack!* "Ohhhh!!!" On and on it went. Jenny looked on with approval as Vicky altered the cadence of the punishment instrument which she wielded with such perfection, so that he would not be able to exactly anticipate the timing. Jenny recognized that he was struggling to stay in position, stood in front of him and gently held his shoulders while Vicky continued. "You just stay in position there. Vicky's going to give you the whole allotment of strokes, and if you get out of position, I'm going to let HER give you the extra strokes, and SHE will decide how many extra to give you." Vicky paused for a moment, then said, "Twenty more strokes to go," and delivered them as fast as she could while he yelled, kicked, and writhed with each one. When Vicky had finished, Jenny allowed him to stand up and move around, but announced that the session wasn't finished yet, and that she had something more to show the women about strapping. After a short break, Jenny told him to get into position again. After he complied, Jenny asked Beckie to pick the numbers and announce them one at a time. When Beckie picked the first number and said the count was six, Jenny took the strap and stood directly behind her boyfriend. "Here's what you can do when you want to really make an impression with the strap", Jenny instructed, and gave six rapid strokes, going in both directions with a forehand and backhand motion. "Oww! Ahh! Oooh! Owwowww! Ohhh! Aaaahhh!", he cried out as Jenny delivered the blows to his already splotched bared buttocks. "He really has a hard time staying in position when I'm doing this," Jenny said with a giggle. Beckie, lubricating heavily from the scene, drew several more numbers from the jar and announced them. Each time, Jenny administered the strokes while standing directly behind her boyfriend, rapidly alternating forehand and backhand strokes while he struggled to receive them. At this point Jenny told her boyfriend that the spanking session was over, and that he could put his briefs on and join in the conversation. He donned his briefs and indicated that he preferred to stand rather than sit. A little while later, the guests left. "God I'm hot," Jenny said to her boyfriend. "Let's go to the bedroom" The Story of Jenny Part 4 - Jenny Gives Enemas Jenny's boyfriend loved the way she said the word 'enema'. The word came out slowly, with the final syllable drawn out. Enn-eh-muuuuh. Jenny didn't always pronounce 'enema' that way. She would only draw out the final syllable when she wanted to emphasize the word, and when she was feeling aroused. "It's enema time now", Jenny said to him with a teasingly coy look. "You get undressed now and I'll get your water ready. We have all day, and I'm going to give you several enemas. Take them well and I won't whip you too much between each ennnehhmmuuuuuh." Jenny always used a generous supply of soap in the water for the first enema of a series. This first enema was the most difficult for him because of the soap, which tends to increase the cramping and the urge to evacuate. At Jenny's insistence, he kept his body clean-shaven from the waist down, including pubic hair. She liked him that way for his enemas, and it also established her dominance over him. He heard the water running as he undressed. Jenny had set up the large towels on the bathroom floor. "Okay, we're ready now. Come and get your ennemuuuuh!", Jenny called out a few minutes later. He trembled inside as he knelt on the floor with his bottom up and his forehead touching the floor. Jenny had a disposable glove on one hand, and lubricated the middle finger of that hand. A short gasp came from him as she inserted her lubricated finger and probed him with it, sliding it in and out a few times and stimulating his prostate before withdrawing and tossing the glove. He heard Jenny let a little of the hot soapy water run out from the enema hose into the sink. Then he felt the nozzle as Jenny pressed the tip against his rectal opening. A little shove, and it slid in. Holding the full two-quart bag, Jenny released the valve and the soapy enema solution started to flow into him. After a moment he started to groan and squirm. "Ooh, Jenny, OH!", he exclaimed. She adjusted the level of the bag from time to time to effect a slower or faster flow depending on his reactions. When his protestations reached a certain level, she would pinch off the flow for a moment to give him some time for the soapy solution to go further inside. He knew that she enjoyed seeing him squirm and struggle - she tells him so every time she gives him enemas. He thought of the inevitable whippings between each enema of the series, and how she loved to administer them. He wondered if he was going to get the strap, the paddle, or the cane today. He never knew until it was time for him to get it. He also thought of the intense hours of pleasure that they would both enjoy after his ordeal with the repeated enemas and whippings. His attention became abruptly focused on the enema by a feeling of fullness in his insides, and he delighted Jenny with intense squirming and pleading for relief. She stopped the flow for a moment, telling him that he needs to take the whole thing and that he'll have to hold it for at least five minutes before letting it go. Jenny resumed the flow and he felt the remaining soapy solution penetrating his innards as the bag gurgled and drained. She slowly withdrew the nozzle, and stood directly in front of him as he stayed in position for the full five minutes, sometimes groaning, sometimes pounding on the floor with his hands in an effort to retain the warm soapy enema. After what felt like an eternity, Jenny let him up and left the room for about twenty minutes as he discharged all the enema. When he was sure there was no more liquid to come out, he opened the bathroom door and saw Jenny standing with a strap in her hand and a coy smile. She led him to the bedroom, and pointed to the bed, where she had placed two pillows and a large towel over them for him to lie face down for his strapping. When he was situated, Jenny went to one side and started, giving hard, regularly paced strokes with the strap. After giving ten strokes, she walked around to the other side and administered the next ten from there, and continued until the count had reached forty. She prepared his next enema while he stayed on the bed following his first between-enema whipping. This time she prepared the two quart bag, but without soap, using a little salt in the solution to maintain osmotic balance. She also prepared the same solution in an extra pitcher, so that she could add some to the enema bag before it drained completely. This way he would take more than the two quarts. She told him to lie on his back for this one, and when he was in position, she lubricated the nozzle and had him raise his hips while she inserted the tip inside him. Jenny started the enema, and adjusted the height of the bag she was holding to regulate the flow. In the position he was in, he could see Jenny and her facial expressions as she straddled him. At first, the enema solution flowed easily into his partially-cleaned-out insides. This enema was intended to go deeper. When the bag had drained about one quart into him, it got to be more difficult. Jenny lowered the bag a little to ease the flow, and she also added some of the prepared solution from the pitcher until the bag was full again. One thing that he could count on is that each enema during a series was a little different, as Jenny contrived ways to make it interesting for herself and for him. Telling him to breathe fully, Jenny kept raising and lowering the bag until the last of the solution drained into him. She withdrew the nozzle and stood directly over his face so that he could see the beginnings of dampness on her panties. He also liked to grab hold of and feel her bare legs when she was positioned this way, to keep his mind off the enema that he had to hold for at least five more minutes. Jenny quickly pulled her panties off and stood over him. As he focused on her glistening womanhood, she started to massage her labia and clitoris, eventually treating herself to an orgasm. When the once-more interminable five minutes ended, Jenny left the bathroom while he released all the enema from within him. About twenty minutes later, he walked out of the bathroom and saw Jenny with the strap in her hand, pointing toward the bedroom. With a sigh, he positioned himself over the pillows which presented his bared bottom for Jenny's strap. This time she gave a fast-paced strapping, delivering fifteen hard strokes before prancing to the other side of the bed and delivering the next set. When she had given him forty five strokes, she prepared his next enema. She prepared a clear warm-water solution, called him to come into the bathroom, and ordered him to lie on his back. Jenny spent ten minutes filling him up with a little over three quarts, encouraging and admonishing him during the whole process. She also manipulated his cock and testicles during some of the more difficult times, as well as during the retention period after all the solution was inside. When she left him alone to discharge the enema solution, she set up a chair in the next room for him to bend over for his next whipping. He was not looking forward to this, since each of the whippings that Jenny administers during an enema series is more intense than the previous one, due to her mounting excitement. He was also aware that there was at least one more enema to be endured, with its accompanying whipping afterward. A wide-eyed enthusiastic Jenny treated his bare bottom to over fifty well-placed, vigorous strokes of the strap as he was required to stay in position bent over the back of the chair. Then she prepared his fourth enema of the day. When she summoned him into the bathroom for that enema, he noticed that she had placed a stand in the room so that she would not have to hold the enema bag while he received the solution. She lubricated the nozzle and inserted it into his backside, then started touching, teasing, and caressing him all over until he got a raging erection. Now, with the bag relatively high up for a fast flow, she released the clamp and started the flow. As the enema gurgled into him, his erection diminished. When his erection was about half gone, she stopped the flow and teased and touched him until his erection came back. Then she started the flow again. She did this over and over, pausing once to refill the bag when it was almost empty, until he had almost four quarts in him. She kept up the sensual stimulation through the retention period, then left him alone for about twenty minutes. Story of Jenny Ch. 01 He came out of the bathroom seeing Jenny with the strap in her hand, beckoning him sexily to come hither. He followed her into the living room where she pointed to the padded ottoman, and he placed himself face down over it. Jenny was extremely excited now, and mercilessly strapped him at steady pace without pausing. While he yelled, squirmed, and urgently pleaded during her delivery of over sixty vicious strokes, Jenny brought herself to multiple climaxes. "Into the shower now, get all cleaned up!" Jenny said to him. She rested while she heard the water running. As soon as it quit she went into the bathroom, got the towel, and in a pampering mood, dried him. With a flourish she dropped the towel on the floor and led him by the hand into the bedroom. She quickly shed all her clothes, and then took his penis completely in her mouth. Jenny looked up into his eyes innocently, and felt his member harden as she teased it with her tongue. The Story of Jenny Part 5 - Jenny Learns To Use A Switch Jenny and one of her new friends, Melissa, had lunch and were discussing their love for administering discipline to their boyfriends. Melissa asked Jenny if she ever used a switch, and Jenny answered that she had not, that she has used the paddle, hairbrush, strap, and cane. "Oh you've got to try the switch - there's nothing like it," the tall redhaired Melissa said. "I get so much pleasure from using switches - more so than the cane. I'll show you how to use it. Would you like to see me use it on my boyfriend?" "I'd love to. But why don't you use it on my boyfriend," Jenny replied. "You can show me how to use the switches and you'll get to use them on somebody different." "Ooooh, I like that idea. As long as I have free reign and complete control of the session. No restrictions at all," Melissa said with wide eyes. Jenny agreed, and they set a day and time for Melissa to come over. Melissa promised to bring some switches with her. Jenny told her boyfriend that he would be "receiving some attentions" from someone he had not met, and that this new person would have complete control of the session. She did not mention what those attentions would be. He had an idea that it was physical discipline, but he didn't know what flavor. Melissa showed up two days later with a bundle of unprepared switches wrapped in newspaper. After the introductions, she asked if she could begin. When Jenny gave her assent, Melissa ordered Jenny's boyfriend to go to the bedroom and get completely undressed, and to come back. A few moments later, he quietly came back, completely naked, and Melissa commenced to show them how to prepare switches after they're removed from the tree. She demonstrated how to trim off the loose shoots, to cut off the straggly ends, and to smooth out the switch. Then Melissa put the switches down, sat in a chair, and told him to stand in front of her. When he did, there was complete silence in the room for a few moments. He felt her gaze all over his body. She had him turn around, while she subjected him to the same scrutiny with his back toward her. Then she told him to face her again, and to stand about a foot in front of her. This was designed to make him apprehensive, and it was working. He felt as though his abdominal area was trembling, partly from fear and partly from excitement and anticipation. Melissa reached over and cupped his genitals in her hands. He immediately started to get erect as she used both hands to massage his penis and testicles. After a moment, she curled her thumb and forefinger around the base of his testicles and gave a few brusque tugs. He groaned at this mixture of pleasure and aching pain from the tugging. Then she withdrew her hands, and waited until his erection subsided somewhat. Then she gave him another scrotal tug, and, keeping her hand in place to give more tugs, she started to ask him questions. "Have you ever had a switching before?" she asked. "No," he replied. She gave him a hard tug and he reacted with "Aughhh!". "No, what?" Melissa demanded. "Oh... No ma'am," he replied, catching the direction he was expected to go. "You know you're going to get a good switching today, don't you?" "Yes ma'am." Tugging lightly, she asked, "And you know it's going to hurt - a lot." "Yes ma'am." "Do you know why I'm going to give you a severe switching on your bare bottom today?" "No ma'am." Accentuating each word with a brusque tug, she said, "because... (tug) it... (tug) pleases... (tug) me!" (tug) Tugging a little harder, and rhythmically, she said, "And you know that I'm going to switch you until I decide to stop, don't you?" "Uhh... Yes ma'am," he groaned. "And you know that you had better not get out of position during the whole switching, don't you?" she asked, interspersing the tugs with an occasional light squeeze on his testicles. "Ohhhh... Yes. Yes ma'am." "A switching really, really hurts," she said, giving him a few harder tugs. His throbbing, erect penis bobbed up and down with each tug. "You definitely do not want to get out of position! You know that, don't you?" "Yes ma'am! Uhnh..." Continuing her tugging and squeezing, she said, flashing her eyes coyly at him, "You will be tied down and punished very, very severely if you get out of position. But you'll be well rewarded if you stay in position for it. I get really turned on when I give a good switching! It makes me creamy. Yes?" "Oh... Yes ma'am!" "Good," she said, withdrawing her hand. "Let's get started. I want you, when I get up, to put this chair in the middle of the room, bend over the back of it, and hold on very tight, because you've never felt anything quite like you're going to feel today." Melissa got up and retrieved the switches and placed them on a nearby table while he followed her directions. Jenny smiled at him when he looked at her, and he could tell that she was getting aroused, just by the look in her eyes. When he was bent over the back of the chair, the red-haired Melissa walked up behind him and started to prod, pinch, and palpate his bared buttocks, as if she were examining a cushion or a pillow for firmness. After a moment of this, she very lightly touched and ran her fingers over the surface of his testicles, and then did the same to his bared buttocks. Then, picking up one of the switches, and without any further delay, Melissa stepped to his side, brought the switch back, and swiped it across the bared target. Reacting to the intensity of the pain inflicted by the switch, he gave an immediate shout. A scant few seconds later, another stroke. This was followed by another shout. Again and again the wicked switch striped his vulnerable bared target, with Melissa paying no heed to his now urgent outcries. He kicked his feet and writhed with each stroke, while Melissa's face reflected a combination of interest, excitement, and arousal. She parted her lips and chenched her teeth as she administered to him. After giving him about two dozen strokes Melissa paused, picked up a fresh switch, and walked around him slowly a few times, whisking the switch through the air so that he could hear its fearsome sound. She gave him this brief rest since she didn't want to force him to get out of position, although she knew that she could if she wanted to. It was her intention to bring him close to that point a few times during the adventure, but not to deliberately force the issue. She took her place again and renewed the vigorous application of the switch. Most of the stokes by now overlapped where the switch had previously struck, intensifying the pain. Again, he pleaded with her to stop, to not hit so hard, to do anything but keep up the onslaught which she immensely enjoyed. Melissa picked up the pace, delivering the switch strokes faster than in the first set, and paused again after a couple dozen strokes. He panted and groaned during the pause as she again circled around him, not saying a word. Melissa put down the switch and teased her fingers lightly on his testicles, and then cupped her hands around his genitals and massaged lightly until his penis started to get hard. She gave his testicles a few tugs, picked up a fresh switch, and started another set of strokes. She delivered this set harder, and with an even cadence, for the entire set of two dozen, before pausing. She did not walk around after this pause, but simply stood silently where she was. After a few moments, she delivered twelve strokes as fast and as hard as she could, and then stopped. She told him to get up and turn around, and mentioned, "You did pretty good, not getting out of position. Jenny promised me complete control of the session, and that includes any extra reward and punishment. I want you to get down on your knees." When he complied, Melissa kicked off her sandals, hiked up her short skirt, and commanded, "I want you to take my panties off - with your mouth." He groveled up to her on his knees, and started to awkwardly tug down her panties, bringing them down first a few inches on one side, then on the other. He noticed that the crotch area was soaked through from Melissa's own cream. He took in the scent of Melissa's dampness all the while. When her panties were on the floor, she stepped out of them. Melissa obtained a towel, spread it on the sofa, and sat on the towel with her skirt pulled up. Then she spread her bare legs as far apart as possible, and told him to approach her. With his erect member sticking out in front, he came up to her, still on his knees. She started masturbating herself, obviously enjoying the show she was giving him, and his reaction to it. She had him stay kneeling in front of her while she crested twice. Then, positioning herself, still with her legs spread, so that her creamy vaginal entry was a couple inches back of where the edge of the sofa was, she said to him, "Okay, now you can go inside me - but you must stay kneeling at all times - and you'll only be able to go in a little bit. You may ejaculate inside my body." He looked at Jenny, and saw her wide, excited eyes. She subtly nodded, letting him know that he was to go ahead with Melissa's plan. With a hard, throbbing member, he approached Melissa, and then, with some effort, entered her moist, glistening womanhood scarcely more than an inch. With thrusting movements, he could not penetrate more than halfway. After a few moments of this he couldn't help spurting a full load into her receptacle, mixing his juices with hers. Now completely spent, he withdrew and put his head in her lap. Stroking his hair, she said, smiling, "I told you that there would be a reward for you staying in position." After a few more tender moments, she told him to lie on his back on the floor. When he did, she straddled his face and told him to open his mouth. When his mouth was open, she parted her labia and released the mixture of semen and creamy juices from within her vagina into his mouth. Then she had him lick her clean. Jenny observed all this with rapt fascination and arousal. Jenny had taught other women about disciplining males, but today she learned an immense amount from Melissa. After Melissa left, Jenny took him to the bedroom where they spent the remainder of the afternoon in a passionate repast of sexual pleasure. The Story of Jenny (part 6 - Jenny and the Jill Club - F/M spank) Jenny had recently joined a "Jill" club. Jill is the term for female masturbation. The Jill Club meets once every two weeks, and the members discuss their jilling methods and techniques, as well as how to get more fulfillment from the practice. Jenny had circulated a questionnaire to all the members, asking them to profile their fantasies and scenarios which are conducive to jilling, and also some other personal information. From the information, Jenny determined that there were several of the members who indicated that they are aroused at the idea of witnessing a spanking. Jenny contacted some of them and set up a meeting with seven women who wanted to see the administering of discipline. Sunday afternoon at 2 PM found a group of women from the Jill Club at Jenny's house. She served coffee and pound cake in the family room and made small talk to put the other women at ease. When the coffee and snacks were finished, Jenny described the format of that day's meeting. "All of you are going to witness a severe punishment session, which I will administer to my boyfriend. He will be totally naked during the whipping, and he is going to be bound so that he will take all of it. I'd like each of you to feel free to jill during the session, and keep count of how many times you cum. There will be a special prize for the one whose count is the highest. You're on the honor system now, so keep that in mind. The experience of giving a whipping is extremely erotic to me, and I'll likely jill a lot when I'm giving it to him. But I won't be a contender for the prize. Let's go in the other room now." They all followed Jenny to the living room, where they saw a structure in the center of the room. It was a sturdily built punishment box, with binding straps in several places, and appropriate padding on the top side. "Feel free to be wherever you want to during the session," Jenny advised. "I'm going to go get him from the other room now." Jenny emerged from the bedroom in a few moments, hand in hand with her boyfriend, who was completely naked. At Jenny's insistence, he kept himself shaved from the waist down. The excitement of the women permeated the air, and several of them stared openly at his crotch, as they had never seen a male with a shaved pubic area. The attention of all the women caused him to involuntarily become erect, which embarrassed him. Jenny decided to further his embarrassment by making him answer some obvious questions. "What's going to happen to you today?" Jenny asked him. "I'm going to get a spanking in front of them," he answered. "No - Not a spanking... A whipping," Jenny corrected. "Now say it!" she directed. "Uh... I'm going to get a whipping." "And who is going to give you your whipping," she continued. "You are, Jenny." "Very good. And what happened earlier today?" Blushing, he looked down at the floor and said, "I got an enema." Jenny was taking considerable delight in his present discomfort. "An enema? Just one?" "No... three enemas." "Oooohh! Three enemas. And who gave you the enemas?" "Y-you did." "What was in the enemas?" "Soapsuds in the first one, and plain water for the others." "Were they biiiiiiig enemas?" "Yes!" "A big soapy enema! And two big rinsing enemas! You must be cleaned out good, huh?" "Y-y-yes..." "Okay, enough of that! Let's get you over the box and get going!" She led him to the punishment structure. "Over you go, now," she said as he bent over at the waist. Jenny pleasantly hummed a nondescript tune as she securely tightened a binding strap around his waist. Going to the front of the structure, she secured his wrists in front so that he would not be able to reach back during the whipping. The other members of the Jill Club took in the scene with a mixture of excitement and awe. "Sometimes I tie his ankles so that he can't move his legs while I whip him, but this time I'll leave them free." Jenny announced to the other women, "He can take a considerable amount of discipline, but from time to time I like to extend his endurance. To extend his limits, I give him a very long, drawn out discipline session. That's what I'm going to do today. He will not want to take it all, but as you can see, he has no choice. Any questions?" Lorraine asked, "What is the prize that you talked about earlier?" "Oh, yes," Jenny said. "The prize is that whoever has the highest score gets to fuck him silly with a strap-on dildo." There were some excited "oohs and ahhhs" at that announcement. Jenny distributed hand towels to all the spectators, and said, "Ladies, you may shed your panties - and start your engines!" She pulled her own panties off and stepped out of them. A moment later Jenny picked up a two-tailed tawse which was about 26 inches long and a good quarter-inch thick. Some of the ladies' eyes got big as they caught sight of the strap. "Again, feel free to move around and watch from wherever you want to," Jenny said to the women. Stepping behind and to the left of her bound boyfriend, Jenny extended her arm and positioned the business end of the tawse across the bared buttocks of the male. She took a few minor steps to ensure that each stroke would be placed perfectly across the intended target, drew her arm far back, and started the strapping with a perfect stroke. Jenny swiveled her hips as she completed the stroke with a generous follow-through. A scant few seconds later, the second stroke made contact with a loud crack and a muffled "Oh!" from her boyfriend. Jenny continued the strapping in the same fashion. Some of the women moved to take their place in front of the male to better see his facial expressions as the strapping continued, while the others situated themselves where they could see the reddened effects of the strap on his bottom. Jenny was almost oblivious to them, and had one hand constantly under her dress jilling herself. She would occasionally pause for a moment to climax, and then resume the whipping, with her feet in place and her hips swiveling when delivering each stroke. Christine was seated on the floor directly in front of Jenny's boyfriend, with her legs open and her hand in her brunette bush. Lorraine was seated beside Christine on a chair, and felt excitement beyond anything she had experienced. Josie sat behind him, watching him kick his legs and wriggle in vain attempts to assuage the blistering pain of Jenny's strap. Sabine wandered around from one moment to the next, her knees buckling when she climaxed. Rebecca stayed behind him, while Tori was mesmerized and most aroused by the male's vocal protests and supplication to Jenny. Bridget moved from place to place, constantly stroking her vaginal area, pausing frequently to emit muffled "mmmmf! mmmmffff!" sounds when she climaxed. After Jenny had delivered well over a hundred and fifty strokes, she paused and set down the strap. With a few beads of sweat on her face, she announced that the whipping was not over yet, and that the best part was to come after a short rest. She served some refreshments and the excited Jill Club members made small talk while they cooled down somewhat. "Okay, let's get this show on the road again," Jenny exclaimed, excusing herself to the other room for a moment. She came back holding a whippy rattan cane. It was straight, almost four feet long, fairly thin, and had a rubber handle. She sharply whisked it through the air a few times. When the other women heard the fearful sound it made, much like a switch, the whole room got quiet. "This is going to be the frosting on the cake," Jenny stated. "And this will also be a very generous serving of frosting! Ladies, get ready, and start your engines!" Jenny pranced over to the bound male's left side, and positioned herself exactly by touching the whippy cane on his buttocks, so that it extended past them for a few inches. "Oh, Jenny, no!" he plaintively and sincerely pleaded, knowing that his fearful anticipation aroused her, and probably the other women. Within a few seconds Jenny commenced striating his already strapped buttocks with the cane. The severe strapping had tenderized his bare skin so that the effect of the whippy instrument wielded by Jenny had a more profound effect than usual. This was apparent from his reaction. He kicked his legs, he vigorously jerked his head from side to side in vain attempts to mitigate the scourge of the cane. Very soon his pained exclamations of "Oh!" gave way to more fervent expressions of distress. Impassioned phrases such as "OH! Jenny!", and "Please stop! Please stop!", "OH! Jenny, Please!" accompanied his writhing motions.