Story of Jenny Ch. 01

The ladies' expressions of their climaxes became more prevalent as Jenny increased the pace and intensity of the caning to a feverish pitch. He frantically kicked with each stroke while the women situated behind him watched with spellbound arousal as they jilled themselves.

After a sustained period of caning, Jenny finally stopped. It took a few moments for the observers to compose themselves. Jenny, of course, had jilled herself many times while wielding the cane.

"Okay now, I want each of you to tear off a sheet from this pad and write your name and how many times you came, and I'll collect them to see who gets to use the strap-on dildo," Jenny announced as she gave the pad of paper to Tori. A couple of minutes later she collected all the sheets and went through each one. "And the winner is... BRIDGET!"

The slender, bespectacled brunette with short-cropped hair smiled broadly as the others congratulated her. "Okay Bridget, take off all your clothes now, and come up here," Jenny urged as she walked around in front of her still-tied-up boyfriend. She picked up a box with a new strap-on dildo and harness and opened it.

"This is yours to keep, Bridget," she said as the slender Bridget took her place beside Jenny. "Now put on this harness and cinch it reasonably tight. This part goes inside you and is meant to stimulate you as you're using it," Jenny stated, showing off the item to all the women. The harness had a rippled dildo-like attachment for the female's pussy.

"Ohhhh, wow!" Bridget moaned when she inserted the rippled part inside her. She took a moment to secure the harness so that it was snug but comfortable. There was a little nub sticking out of the harness. Jenny pulled out a dildo made of transparent material and held it up for the others to see. "This one fits on the little nub here," Jenny said, attaching the dildo to the nub on the front of the harness. "It's about seven and a half inches long and almost an inch and a half in diameter. Now let's come over here around back," Jenny continued as they walked behind her bound boyfriend.

Jenny showed Bridget how to generously lubricate the strap-on and when that was done, continued her instruction.

"Now spread his ass cheeks apart and put the tip right against his hole. That's it... Now, very slowly, give a little push and insert a couple of inches."

"Uhhhhhh!" was his reaction at Bridget's penetration.

"Okay now, go back and forth with those couple of inches for a little bit. Yes, like that. Now slowly go further in. That's it. Now back and forth, and go in a little further each time. Good. Now a couple of strokes up to the hilt. Yes. Good. Now pull out and let's put some more lube on it... Okay, back in there. Go in all the way. Good. Now, go ahead and thrust as hard and fast as you want. Fuck his brains out! Fuck him silly!"

Bridget needed no further encouragement, and firmly grasped the bound male's hips with her hands, and began to thrust the strap-on with hard, brusque strokes.

"UH! OH! UHH! OOOH! AAUH! UNGHH!" he exclaimed as Bridget warmed up to her task. She stopped momentarily for a shuddering climax. With a determined expression on her face, sometimes gritting her teeth, Bridget resumed his pounding, talking to him with each thrust, frequently climaxing.

"I'm... going... to... fuck... you... seven... ways... to... Sun... day... you... Ahhhhhhh! Ungghhh! OH God! Ohhhh! Ohhhh! I'm... going... to... fuck... and... fuck... and... fuck... you... silly... till... your... head... spins... and... Ohhhhh! Ohhhhhh! Ahhhhhh! Mmmmmmf! Ohhhhh! You... like... this... don't... you... I'm... going... to... fuck... you... till... your... ass... hole... is... on... fire... Uhhhhh! Uhhhhh! Unnnnnhh!"

Bridget kept thrusting at a feverish pace while he groaned and exclaimed his predicament. The sight of his stretched sphincter hugging the transparent dildo as it rammed in and out was intensely erotic to Bridget, and she had several more orgasms. Finally she stopped, pulled out and, panting, dizzily said, "I can't take any more, Jenny! I'm completely drained!" She removed the harness and staggered to a chair to collapse and compose herself. With a broad smile, Bridget took some time to recover from her emotional stratospheric high, while Jenny released her boyfriend's binding straps and helped him up.

Serving refreshments all around, Jenny remarked at what a turn-on the whole scene was for her and hoped that everyone was similarly aroused. All the women exclaimed that they had enjoyed it immensely.

Jenny spread a sheet on the floor and had her boyfriend lay on it, face up. "He's had enemas, a severe whipping, and a good fucking," said Jenny. "I think he deserves a little reward, don't you? How about if we all participate in giving him a good massage," she continued, producing a container of olive oil. All the women gathered around him. They poured olive oil on their hands and rubbed and kneaded his arms, legs, hands, feet, chest, neck, and middle, while he groaned with pleasure. He gained a throbbing erection from the attention of all the women.

After about fifteen minutes, Jenny interrupted and said, "Okay, I'd like two of you to hold his arms above his head, and two of you spread his legs apart and keep him there, and the rest of us will finish him off after a while." Jenny poured a generous amount of olive oil on her hands and applied it to his testicles and already rigid erection. The others followed Jenny's lead and teased and lightly touched all around his shaved pubic area. The attentions of several pairs of female hands on his testicles and erect member sent him into a state of tormented paradise. The touching and teasing was enough to repeatedly bring him just short of ejaculation.

At Jenny's urging, the women continued the teasing stimulation. "The longer he's teased, the higher he'll squirt," she told them. He was struggling against the women holding him down, begging the others to make him cum. They kept on with the feather-light touching and prodding for a several minutes. Finally, Jenny nodded to them and silently mouthed the word "okay". Jenny and Tori started to palpate his testicles while Lorraine grasped his erection and pumped him to a violent climax. Several streaks of semen pulsed and spurted high into the air to the amazement of all the women while he wordlessly vocalized his ecstasy.

Jenny served another round of refreshments and the women washed up and got dressed. Jenny told her boyfriend not to get dressed. As some of the women were getting ready to leave they told Jenny that they had had an unforgettable experience and that they would like to do this again if there was an opportunity. Bridget went up to Jenny's still-naked boyfriend, put her arms around him and gave him a passionate kiss, and said to him as she felt his resurging erection start to press against her front, "Thank you. That was such an experience!" Turning to Jenny, Bridget asked, "What are you going to do with the rest of the day?"

"Well, first it's a shower for both of us, and a nap for him. We have a deal. After an intense whipping like the one he got today, he gets to have me any way he wants to for a week - and anytime he wants to." There was obvious interest from the women when she said that. "He can do anything except spank me," Jenny continued. "I'm sort of looking forward to it, and I know he must have some plans by now," she giggled.

A few hours later, Jenny sleepily stirred, finding herself becoming slowly awake, lying on her tummy, being entered by her boyfriend. Her vaginal innards welcomed the fullness of his erect and pliant member as it nestled inside her. As the thrusts became increasingly brusque, Jenny reached over and grasped the edge of the mattress with both hands and held on tight. Intense feelings of pleasure surged up inside her and she moaned...

The Story of Jenny - Part 7 Double Trouble, Double Fun (F/MF spank)

"Jenny! This is Brandelin," said the voice over the telephone, "do you remember me?"

"Brandeeee! I haven't talked to you in years! Where are you?" Jenny asked.

"I'm getting transferred here for my job," Brandelin replied. "So I'm here on a two-week house hunting trip."

"Are you still with, uh, I can't remember his name..."

"Oh good heavens no. I ran off with that jerk and then was sorry immediately. Never ended up with a jerk since then. I've had some... interesting relationships in the meantime. We've got to get together and catch up - how about over here at the hotel? There's a pretty good dining room here."

"That sounds good. When are you free?"

"The sooner the better," Brandelin said. "Can you come today?"

Jenny was a few minutes late, so they went directly to the dining room and started in on a leisurely repast. Brandelin wanted to share a full bottle of claret, and Jenny assented. "I seem to remember, Brandy Lynn [as Jenny affectionately called Brandelin sometimes], that wine really loosens you up. Is that still true?"

A slight, almost embarrassed smile from Brandelin. "Yessss... I kinda get uninhibited and say what's really on my mind," She giggled.

And so it went, the two friends bringing each other up to date on their lives, jobs, and families, punctuated with moments of uproarious laughter as the wine loosened Brandelin's inhibitions. The topic finally got around to the more intimate and personal subjects.

"Oh Jenny," Brandelin gushed, "I've got to tell you something." Lowering her voice and reaching over and giving Jenny's hand a squeeze, she implored, "Don't think badly of me. Promise?"

Jenny brought Brandelin's hand close to her chest, gave a squeeze, looked directly into her friend's almost misty eyes, and replied, "Now, Brandy Lynn, I don't want you holding back anything. Tell me!" Jenny released Brandelin's hand and gave her time to compose herself.

"Jenny, now this may sound weird, and if you don't want to talk about it, I'll understand. It's something I can't help." Then, losing her nerve, she said, "No... No, some other time."

Jenny, with a stern look, in a scolding voice, said, "Barbara Brandelin, if you don't tell me, I'm going to give you a good sound paddling!"

Brandelin drew in her breath, quickly put her hand up to her mouth in surprise, and looked at Jenny with huge eyes. "Jenny!" she exclaimed, then lowered her voice to a whisper, "I'm into spanking. What made you say that?"

Surprised, Jenny said, "I don't know, it just came out. Are you into getting spanked, or giving spankings?"

"Well, both. A couple of relationships I was in, they wanted me to spank them, so I did. And then I found out I wanted to experience them too. But you know, I haven't done it, either way, for quite a while. Giving a good paddling is a great stress reliever." Raising her voice excitedly, she continued, "I'D SURE LIKE TO GIVE A GUY A GOOD HARD SPANKING!"

"Shhhhh!" Jenny admonished as some of the other diners looked their way, having obviously overheard Brandelin's proclamation.

"Tee-hee-hee!" Brandelin giggled, then dissolved in embarrassed laughter as she realized what she had done. Jenny couldn't help laughing as well, and decided to enjoy their momentary spotlight from her friend's remarks.

Brandelin went on to describe some of her past spanking adventures. She related how she likes to give paddlings and hairbrush spankings, using, as she termed it, the "wood instruments". She mentioned that she also has some proficiency with the leather strap, but much prefers to use paddles and the hairbrush. "When I use the paddle, or the hairbrush, for that matter, I can play the guy like a fine violin," she boasted. "The 'spanking symphony', or the 'paddle concerto' always goes just the way I want it to. I have some sort of connection with the wood that the strap doesn't give. I suppose I should have some more practice with the strap sometime."

"What about being on the receiving end?" Jenny asked.

"I've given many more than I've gotten. Almost all of the spankings I've gotten have been with the hairbrush or the strap. But you wanna know something, I've never gotten a spanking from a girl. Sometimes I wonder what it would be like." There was a significant pause.

Jenny immediately got an idea of a scenario, although she did not mention any details to her friend. Instead, Jenny described in detail how she got into the scene, and talked about some of her sessions. She got a feeling of satisfaction when she noticed that Brandelin appeared to be getting aroused. Now it's time, Jenny thought to herself, to close in for the kill. Looking at her watch, she exclaimed, "Ooh, look at the time. It's getting late and I'd better leave soon. But I want you to think about something. If you want to participate in spanking this weekend, let me know by tomorrow. I may be able to arrange something so that you can give some spankings."

"Jenny, I'd love to! Count me in!" Brandelin answered with delight.

"Okay, I'll call you tomorrow and let you know where and when!"

They finished up dessert, split the tab, and said their good-byes, complete with warm hugs.

Jenny had arranged for her boyfriend to be at her house at mid-afternoon Saturday, and also told Brandelin to come by at 2 PM that day, so that she would have time to talk to her in person before anyone else arrived.

Brandelin showed up promptly at 2, and Jenny welcomed her with a hug. Jenny made Brandelin feel at ease, and after a little while, poured two cordials of brandy. As they raised their glasses Jenny offered, "To Brandy Lynn!" They both giggled and downed the cordials.

"Okay, Brandy Lynn, here's the plan," Jenny began. "First, you can give him a paddling. I want to see how you operate. Then We'll both spank him at the same time. What I mean is, I'll give a swat, then you'll give a swat, and so on. This will be a good hairbrushing over-the-knee. Sound good so far?"

"Oooh, yeah!" was Brandelin's enthusiastic reply.

"Okay," Jenny continued. "There's one condition. I've never spanked another girl before. So after you paddle him and we both give him a good hairbrush spanking, I want to give you a good spanking. If you agree to that, you can participate. Otherwise you can only watch. What do you say?"

"You - you want to spank me too?"

"Sure!" replied Jenny, looking directly into Brandelin's eyes. "The other night you mentioned that you've never gotten it from a girl, and you wanted to try, remember? And what better time than now, and from a good friend?"

Brandelin looked down for a moment, then, meeting Jenny's eyes with hers, smiled, and assented. "Okay, Jen. What are you going to use on me?"

Jenny answered, "I haven't decided yet. After it's over, you won't regret it, I assure you." Then, with her hands on Brandelin's shoulders, Jenny pulled her close, and whispered, "I want your commitment now. I want you to do whatever I tell you to, without question. Okay?"

Brandelin simply nodded.

Jenny's boyfriend arrived, and Jenny performed introductions.

Jenny told him to fetch the oak paddle, two hairbrushes, the leather tawse, and the straight rattan cane. "Brandy, how do you want him for his paddling?"

"Bent over the back of a chair. This is bare-bottom, right?"

"Of course! It's ALL bare-bottom."

"Do you want him completely undressed, or what?"

"For the paddle, I want him to have his pants down far enough to bare his bottom. For the hairbrush, totally naked."

Jenny's boyfriend came back with the implements and placed them on the table. Jenny strategically placed a dinette chair in the center of the room, and told him, "Brandy's going to give you a paddling while I watch. Do everything she says."

"Come here!" Brandy ordered. She unfastened his belt, unsnapped his jeans and undid the zipper. Then she tugged his jeans and briefs down far enough to expose his bottom and his genitals. "Whoaaaa, what's this!" she exclaimed.

"I have him keep himself completely shaved from the waist down, pubic hair, legs and all," Jenny clarified. Brandelin, never having seen a male with shaved pubes, gazed in amazement as he became quickly erect.

"Wow, that's something else!" exclaimed Brandelin as she cupped his testicles with one hand and lightly stroked his throbbing erection with the other. "Okay, get over that chair, and hold on tight!"

While he complied, Brandelin reached up and undid her ponytail, letting her shoulder-length hair hang freely. Then she picked up the oaken paddle and admired it, feeling the smooth varnished texture, and studying the several holes drilled in it. She approached the waiting male and measured her position with her extended arm. Then, after a moment of focusing her attention on the smoothly shaved bared buttocks of her charge, she commenced her performance.

Quite a performance it was. The paddle made a loud "crack!" every time it made contact. Brandelin seemed to be completely absorbed in her task, almost as if in a trance. Each stroke was administered with a combination of grace, elegance, and remarkable effectiveness. Keeping her eye on the target, she drew her arm far back in an extended arc, and propelled the paddle with steadily increasing speed toward the bared buttocks of Jenny's boyfriend, who exclaimed loudly from each contact. The precise timing of her strokes evoked the most sincere pleading for mercy on the part of the recipient.

Jenny regarded the scene with awe. Brandelin was right about her skill in playing the punishment instrument and the male with finesse, Jenny thought to herself as she felt a tingling dampness between her legs.

After about thirty five strokes, Brandelin stopped. With a broad smile, she turned toward Jenny and took a bow.

"God, Brandy, you're good!" exclaimed Jenny. Telling her boyfriend that he could get up, she took the paddle from Brandelin and set it on the table. Jenny served ice water in frosted glasses and the three of them conversed for a while.

"Okay, let's go on to the next phase," interjected Jenny. "Brandy and I are going to give you a hairbrush spanking at the same time. Brandy, come on and let's get situated." She told her boyfriend to undress completely.

Jenny and Brandelin each moved a straight-backed armless chair facing each other in the center of the room and seated themselves. Moving her chair toward Brandelin's, Jenny positioned herself so that her legs and Brandelin's legs intermeshed. Brandelin's legs, from well above the knees on down, were in contact with Jenny's, thus forming a solid combined lap. "Bring us two hairbrushes and get over our lap," Jenny commanded as she pulled Brandelin's skirt up to further bare her legs. After he took his place, Jenny continued, "Okay Brandy, for every stroke that I give, you give him one. I'll pause now and then."

Jenny delivered the first stroke. Brandelin followed with a powerful stroke almost immediately. "Auuuughh!" was his reaction at each of Brandelin's swats. Jenny paused after giving ten swats, each one being mirrored by Brandelin with a graceful yet exquisitely powerful stroke. This kept up for several sets of strokes, accompanied by the male's squirming and protesting. After what was to Jenny's boyfriend an interminable hairbrush spanking, Jenny delivered an extended set of twenty strokes very rapidly, with Brandelin flawlessly following each one so that there was a steady rain of hairbrush swats. After a moment of rest, they let him up for a break.

Jenny excused herself for a moment, emerging from the other room with a spreader bar with a chain on it, some wrist cuffs, and several binding straps. "Wow, Jenny, this is getting exciting," gushed Brandelin, unaware that she was squeezing her legs together in excitement. Jenny smiled, stood up on a chair and hooked one end of the chain to a strong hook that was anchored in the ceiling.

"Okay, Brandy Lynn, come on and step over here," directed Jenny.