Story of Jenny Ch. 01

Brandelin rejoined, "What?!!"

"Come on! You made a commitment, remember? Come over here!"

"What... what are you going to do?"

"I'm going to give you a spanking... and him, too." Jenny beckoned her to come. Brandelin stood up and self-consciously stepped over to where Jenny was. "Step out of your panties now," directed Jenny. "Everything's on the bare bottom, remember?" Brandelin reached under her skirt, tugged her panties down, and stepped out of them. She looked at Jenny with a "what next?" expression. Jenny had her boyfriend stand directly in front of Brandelin. Then she directed both of them to extend their arms outward and grasp the other one's hand, palm-to-palm, and intertwine their fingers. Jenny slipped wrist cuffs around each pair of wrists and attached them to the spreader bar. She came up behind Brandelin, reached around and unbuttoned Brandelin's blouse and opened it up so that she was bare-chested.

"Come closer together now you two, I want you belly-to-belly," Jenny directed. When they were close enough to Jenny's satisfaction, she lifted up Brandelin's skirt from behind, so that she was bare-bottomed, and placed a binding strap around them both at the waist. She tucked Brandelin's skirt up under the binding strap, pointed her boyfriend's raging boner downward so that it was nestled in the front part of Brandelin's skirt, and tightened their bonds. The male had to stand with his feet apart because he was a little taller than Brandelin. Brandelin's thighs and legs were in delectable contact with his. Jenny stepped back to admire the scene. There was her boyfriend, totally naked, front-to-front with Brandelin, who was bare-chested, bare-bottomed, and bare-legged, with their hands together and wrists cuffed to a spreader bar.

"One more little thing," Jenny said to them. "I'll be right back. Don't go away!" she giggled.

A few minutes later she returned and slipped a leather harness over their heads. The harness was open-space and was meant to affix the position of their heads so that they had to remain face-to-face. "I want you two to get to know each other," Jenny stated as she tightened the harness so that their lips were almost touching. Since the harness was open, they could see into one another's eyes. A moment later, Brandelin gasped as she heard Jenny say, "I thought you'd be well lubed on your own down there," and then moaned as Jenny inserted something into her pussy.

Jenny had placed two hollow steel balls, each of which contained a smaller, solid ball, into Brandelin's pussy, and pushed them well up inside. Every time Brandelin moved, the two balls would either strike one another and send shock waves of feeling through her innards, or they would tend to stir around, further exciting her. Jenny up the leather tawse and teased, "You've got the entire dance floor now, and no one will cut in!"

With that, she started what was to be a lengthy strapping session. She whipped the tawse across the bared buttocks of one of the duo, then walked around and gave the other one a powerful swat. Several times she gave one of them two or three rapid strokes in succession, doing likewise to the other one. Brandelin exclaimed with every stroke, while Jenny's boyfriend only cried out when Jenny gave him a particularly hard swat, or gave him several in succession.

The session was an incredible turn-on to Jenny's boyfriend. In spite of the pain of the energetic leathering of his bared bottom, his throbbing erection never subsided, and continued to press into the front of Brandelin's skirt. Brandelin's wide-eyed exclamations, combined with her frantic movements when she felt the searing heat of the tawse, kept him rock-hard. Their front-to-front physical contact, plus his seeing Brandelin's face at such close range and feeling her legs kick, brought him to the brink of ejaculation several times. He knew that if he ejaculated, he would shoot his semen onto Brandelin's skirt, and he didn't think she'd appreciate that. Jenny sensed his nearness to cumming, and wanted to push him over the brink. She put down the tawse and picked up the straight rattan cane.

"And now, Miss Brandy Lynn," she said, sharply whisking the cane through the air several times, "here's a taste of the cane for you!" Jenny applied several smart strokes of the cane across Brandelin's nether cheeks, each one immediately next to its predecessor. The urgency with which Brandelin reacted, thrusting her front into that of her bound partner, served both to excite Jenny's boyfriend further and considerably enhance the pleasurable sensations within Brandelin herself from the vaginal balls. Jenny stopped whipping as soon as Brandelin started to climax. Jenny's boyfriend could hold on no longer, and spurted uncontrollably into the front of Brandelin's skirt, moaning and writhing as he squirted.

Jenny left them alone for a few moments to regain their composure, and then removed the binding strap that held them together, followed by the harness that was over their heads, and finally, the wrist cuffs. "Oh God, Jen, I've never cum so hard in my life!" declared Brandelin when she was released from the wrist cuffs. She extracted the steel balls from her pussy and declared, "I've got to get some of these."

Pointing to the massive wet spot on Brandelin's skirt, Jenny said, "Look what he did on your skirt, Brandy! I think he should get some strokes of the cane for that, don't you?"

"Oh my gosh, look at all that cum!" Brandelin exclaimed when she looked downward at her skirt. "Yes, I agree he should be punished for that! May I do the honors?"

"By all means, Brandy," announced Jenny, handing the rattan instrument to Brandelin.

Brandelin grabbed him by the arm and marched him over to one of the chairs in the living room. Pointing at the chair, she ordered, "You bend yourself over that chair right now!"

Jenny quickly slipped out of her panties and lay back in a recliner with her legs spread and her fingers working her pussy.

Brandelin continued, "Bend over more. I want your back to be level. There. Okay, now arch your back and stick out your bottom. Like that. I want you to stay with your bottom stuck out like that, or I'll give you three extra for every time you don't!" Turning to Jenny, she asked, "How many should he get? I'm thinking around fifteen."

"That's about right. Make sure he keeps his bottom out there for you," Jenny replied, deftly working her fingers in and around her creamy pussy.

Brandelin positioned herself so that the tip of the cane extended well beyond the far side of the male's buttocks. "Nasty boys who cum all over ladies' skirts get punished severely! You're going to get a good caning, you naughty boy!" Brandelin drew the cane back and whipped it hard against his waiting buttocks. The tip of the cane curled around and struck the especially sensitive part of the buttocks, leaving a thin red stripe.

"Aaaahh!" he immediately shouted when the cane left its mark. Brandelin pressed her lips firmly together and gave another hard stroke. "Owwwww!" She continued. When the count reached seven, he flinched and retracted his buttocks. "No!" shouted Brandelin. "Keep your bottom out there! Three extra!" He tried his best, but couldn't keep still, and wiggled too much after the twelfth stroke. "You did it again! That's six extra. (*whack*) Thirteen... (*whack*) Fourteen... (*whack*) Fifteen. Now stick out your bottom, you nasty boy, for the six extra!"

Jenny, finally obtaining release from the pent-up arousal from the afternoon's adventures, had one orgasm after another at the sight of Brandelin's whipping her boyfriend, and shamelessly moaned each time she climaxed.

Brandelin came to love the sound of the rattan as it whipped through the air on its way to the punished male's bared bottom. She delivered the six extra strokes especially forcefully, evoking a loud shout from him with each one.

"Wow, Jenny, I haven't had such an exciting day in ages!" proclaimed Brandelin. "Thank you for the wonderful time." Turning to Jenny's boyfriend, she said, "And special thanks to you for enduring the spankings from me. I hope Jenny will be real nice to you for that."

Jenny served more cool drinks and Brandelin freshened herself up and left. Jenny looked at her boyfriend's striated bare bottom and commented, "She DID give it to you good! Let's go in the bedroom and I'll put some cream on there and make it feel all better." She took two full pillows and placed them in the center of the bed, and spread a towel on top of them. "Okay, face down and relax, I'll go get the cream." Tenderly, Jenny spread some soothing cream on her boyfriend's buttocks. He reveled in her skilled touch. Then she straddled him and massaged his lower back for a few minutes, then tantalizingly spread some cream around his back opening.

She then applied a generous portion of the cream to the strap-on dildo that she had surreptitiously put on when she fetched the ointment. Slowly, Jenny spread apart her boyfriend's nether cheeks and gingerly placed the tip of the strap-on against his back portal. A little shove, and it was in about an inch. He moaned, and she saw his erection harden. Working it back and forth, she went in a little further with each thrust.

"Oh, Jenny! Jenny, that feels so good..."

The Story Of Jenny Part 8 - Hard Cindy and the Birthday Party

Everyone knows that with some people, birthdays result in spankings. Jenny's boyfriend's 29th birthday was approaching, and she told him that she wanted to give a party, and asked him what he wanted. She was surprised at the answer. They both knew that he would likely get spanked soundly at the party. That was understood from the start. She had not, however, anticipated at all his request, and had to consider it.

Saturday came, and she presented him with the gift wrapped books and compact discs that she knew he'd like, along with an envelope, which she excitedly urged him to open. He unfolded the paper within the envelope, looked at it, exclaimed, "How sweet! Just what I asked for!" and gave her hugs and kisses.

Jenny treated him to dinner at their favorite steakhouse, and afterward they went to Cindy's place for the party. Several of Jenny's friends were there, some of whom her boyfriend had met, and several he had not seen berfore, including Cindy. The first thing he noticed about Cindy was her legs, which she obviously delighted in showing. Cindy had wavy auburn hair, parted in the middle, that came down past her shoulders. Her full lips, wide smile and round eyes reminded him of some of the supermodels that he had seen gracing the covers of Jenny's magazines. Cindy also wore a short dark skirt which ended several inches above her knees. And her strong-looking bare legs were perfectly smooth.

The guests mingled. Anecdotes filled the air, laughter abounded at stories and one-liners, and the guests consumed refreshments.

"Okay everyone," Cindy shouted to get their attention. "Before we bring out the cake, we have some tradition to observe tonight. In case any of you don't know," she paused while some of the women snickered, "the birthday boy gets a birthday spanking. One swat for each year, and possibly some extra to grow on! Jenny's boyfriend is twenty nine today, and I'm going to give him his 'official' birthday spanking. But before that, I want everyone's help in 'prepping' him for his real birthday spanking. First, I want Leesa to give him an 'unofficial' birthday spanking. Leesa is just learning how to apply the hairbrush, and she'll warm him up for the real thing. After Leesa is finished, I'll 'horse' him while every one of you gives him three swats of the strap for good luck! Leesa, please take your chair out to the center of the room and be seated."

Leesa was fairly tall, with long, very blonde, almost totally yellow, hair. She wore a long dress and black platform sandals with three inch heels. Blushing and smiling broadly, she placed her chair as Cindy suggested, and sat down, her hands in her lap. She had a slight overbite such that when her mouth ws relaxed, it appeared that she was smiling. "Okay Leesa, you've done this a couple of times before," Cindy mentioned. "Get your lap level, and pull up your dress in case there are any 'accidents'" Leesa slowly pulled her long dress up to her hips, exposing bare legs and thighs. She placed her knees together almost touching, and her feet were about a foot and a half apart, with her toes pointed inward. Cindy handed Leesa a sturdy wooden hairbrush and said, "You handle it from here. Remember that all spanking is done on the bare bottom!"

Her blue eyes twinkling, Leesa beckoned with her finger for Jenny's boyfriend to approach. He came over to her, and had decided to test her by not doing anything without her telling him. Placing the hairbrush in her lap, she unbuckled his belt, unzipped his fly, and tugged his jeans and briefs down to mid-thigh. As soon as she did this many of the other women hooted, hollered, and gave wolf-whistles. In a somewhat high voice, punctuated frequently with a squeak at the end of a word, Leesa told him to get over her lap. With a boner quickly forming, he did as directed, noticing how nice her bare thighs felt. "You get twenty nine swats, young man," Leesa squeaked, and started administering. It was easy to tell that she was a novice at this, sice she did not swat very hard, and also rather carelessly placed the swats. She counted aloud after each swat, her squeaky voice giving him a raging hard-on. After the twenty ninth swat, she stopped and looked at Cindy.

"Leesa, you can do better than that. Do the whole thing over again, this time HARDER, with better aim, and hold on to him with your free hand," Cindy announced.

Leesa sighed, placed her free hand above his waist, and started anew, counting aloud again. Her swats were a little harder and better placed, and it was clear that she had a way to go before she developed a commanding proficiency. When she finished, Cindy said, "Very good, Leesa. You still need lots of practice, which I'm sure you won't have any trouble getting. Now let him up and we'll go round robin."

Jenny's boyfriend stood up and Leesa got up. Cindy loosened and removed the belt she was wearing, which was a good two inches wide, doubled it up, and handed it to Leesa, who happened to be nearest Cindy at the time. Cindy led Jenny's boyfriend to the center of the living room, turned around so that he was directly behind her, and reached back over her shoulders for his hands. She pulled him closer so that the front of his shoulders were against the back of her shoulders, and bent over, lifting his feet off the floor. Cindy directed, "Three swats, Leesa. Then hand it to the next person!"

Leesa swiped the belt across his buttocks three times and handed the strap to Tori. Tori stood to one side and gave three hard swats, with a tennis-stroke follow-through. "Aaaaah! Ohhhhh! Oooooh!," he cried out when he felt Tori's forehand swats. Tori handed the belt to Jocelyn, who gave three medium swats. And on it went, with some the women giving extremely hard strokes, and others imparting strokes of medium severity. When everyone had taken their turn, Cindy released the male, who rubbed his reddened bottom.

"Now for the real thing," Cindy said as she took her seat in the chair that Leesa had used to give him his hairbrush paddling. With her beautiful bare legs a few inches apart, she pulled up her skirt a few inches, and looked at him with a coy expression. "My ex-husband, and all my boyfriends I've had, have called me 'Hard Cindy'" she told him, in a voice meant for everyone to hear. "I don't have ANY idea why!" Several of the women burst out laughing when she said that. "Get across my lap now. Put your thing between my legs," referring to his boner.

"Leesa, come here, I want to tell you something," Cindy directed after the male was positioned. She whispered a few sentences in Leesa's ear. Nodding, Leesa immediately went to the other room. "Jenny, I think you should hold on to his hands while I do this. I don't want him squirming excessively," Cindy offered. Jenny came over and held on to his ourstretched forearms as he lay across Cindy's lap.

"Get ready, now. Here it comes," Cindy warned, and placed a severe hairbrush swat across his right bun. "One," she counted. "Aaaaugh!" was his reaction to a hairbrush stroke that was more powerful than many paddle strokes that he had received in the past. Scarcely a couple of seconds later the hairbrush crashed down on his left buttock. "Two!"

"Owwwwwww!!" he exclaimed.

He then felt a pair of well lubricated hands palpating his testicles and milking his rigid penis. Looking to his side, he saw Leesa kneeling with her hands between Cindy's legs, intently doing Cindy's bidding. The severe hairbrushing from Hard Cindy continued, each stroke more powerful than he ever imagined possible with a hairbrush. He exclaimed loudly with every stroke, at the same time intensely aroused by Leesa's expert hands. After the twenty-ninth swat, Cindy paused while Leesa brought him to ejaculation, milking his semen into a wine glass while he moaned and wriggled.

When Leesa withdrew from the red-faced male, she placed the wine glass that held the copious milky-white fluid, on the mantle. Then Cindy announced, "And now, ten more to grow on!" and placed ten powerful swats on his buttocks while he shouted and wiggled with each one. Jenny let go of him after that, and he got up and rubbed his well-paddled bottom.

"Stay there, Cindy," Jenny said, and whispered into her boyfriend's ear. He went to his clothes, retrieved the contents of the envelope that Jenny had given him earlier that day, and handed it to Cindy as he explained the situation. Cindy opened up and read the sheet of paper, looked at Jenny standing with her legs pressed together, and then looked at Jenny's boyfriend. "Okay, I'll do it," Cindy assured him.

Speaking to everyone at the party, Cindy said, "One more thing... I've got something here I want to read to all of you. Jenny gave her boyfriend a very special birthday gift, which is written on this sheet of paper. It says, 'The bearer of this certificate is entitled to compel Jenny to undergo an over-the-lap hairbrush spanking consisting of not less than 24 strokes of the hairbrush. To be redeemed, this certificate is to be presented to the spanker who will perform the honors. This certificate may be redeemed at any time and I, Jenny, agree to undergo said spanking as a token of my love.' Signed, Jenny."

Her eyes damp with emotion, Jenny spoke up. "I want to give him this gift in front of all of you. I suggested that he redeem it now, and... and... I want everyone to know that I willingly give it." Jenny walked over to Hard Cindy's side, reached under her skirt, pulled her panties down to her knees, and leaned across Cindy's lap. Cindy raised Jenny's skirt up to expose her bared bottom. Jenny extended her arms in front of her, and her boyfriend grasped them, knowing that he had to hold on tight. To his knowledge, Jenny had not experienced the kind of discipline that she was so skillful at meting out, and this was to be a sort of initiation.

"Twenty-four swats, Jenny," Cindy affirmed. "I wouldn't be true to myself if I gave them any differently than what I give to the others, so they'll be just as hard."

Jenny nodded in assent. Cindy started Jenny's spanking. Everyone watched the hardwood hairbrush descend on Jenny's firm, rounded buttocks.

Jenny shouted from the first stroke. She squirmed, wriggled, bucked, tossed her head from side to side, and loudly exclaimed after every stroke. She held on to her boyfriend as tightly as he gripped her forearms, determined to give him this gift without regret. Jenny had resolved to take the entire spanking without asking or begging for it to stop. This was most difficult for her, and every time she felt the word "stop" forming in her mouth, she instead shook her head and yelled, "No! No!" Jenny's boyfriend, as well as Cindy, recognized that when Jenny did this was telling herself not to ask for it to stop.