Story of Jenny Ch. 01

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.