The Jill Club

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The Jill Club

The Jill Club

Vanessa had recently joined a Jill club. 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. Vanessa 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, Vanessa determined that there were several of the members who indicated that they are aroused at the idea of witnessing a spanking. Vanessa contacted some of them and set up a meeting with seven women who wanted to see corporal discipline.

Sunday afternoon at 2 PM found a group of women from the Jill Club at Vanessa 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 snackswere finished, Vanessa 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 Vanessa 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, Vanessa advised. I m going to go get him from the other room now.

Vanessa emerged from the bedroom in a few moments, hand in hand with her boyfriend, who was completely naked. At Vanessa 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. Vanessa decided to further his embarrassment by making him answer some obvious questions.

What s going to happen to you today? Vanessa asked him.

I m going to get a spanking in front of them, he answered.

No – Not a spanking… A whipping, Vanessa 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, Vanessa.

Very good. And what happened earlier today?

Blushing, he looked down at the floor and said, I got an enema.

Vanessa 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?


A big soapy enema! And two big rinsing enemas! You must be cleaned out

good, huh?


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. Vanessa 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.

Vanessa 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, Vanessa said. The prize is that whoever has the highest score gets to fuck him with a strap-on dildo. There were some excited oohs and ahhhs at that announcement.

Vanessa distributed hand towels to all the spectators, and said, Ladies, you may shed your panties – and start your engines! as she pulled her own panties off and stepped out of them. A moment later Vanessa 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, Vanessa said to the women.

Stepping behind and to the left of her bound boyfriend, Vanessa 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. Vanessa 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.

Vanessa 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 whipping continued, while the others situated themselves where they could see the reddened effects of the strap on his bottom. Vanessa 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 Vanessa s boyfriend, with her legs open and her hand in her brunette bush. Lorraine was seated beside Christine on a chair, and was excited 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 Vanessa 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 Vanessa. Bridget moved from place to place, constantly stroking her vaginal area, pausing frequently to emit muffled mmmmf! mmmmffff! sounds when she climaxed. After Vanessa 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. Vanessa 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, Vanessa exclaimed, excusing herself to the other room for a moment. Coming back, she held 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, Vanessa stated. And this will also be a very generous serving of frosting! Ladies, get ready, and start your engines! Vanessa 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, Vanessa, no! he plaintively and sincerely pleaded, knowing that his fearful anticipation aroused her, and probably the other women. Within a few seconds Vanessa 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 Vanessa had a more profound effect than usual. This was apparent from his reaction. His legs kicked, his head vigorously swayed 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! Vanessa! , and Please stop! Please stop! , OH! Vanessa, Please! accompanied his writhing motions. The ladies expressions of their climaxes were becoming more prevalent as Vanessa increased the pace and intensity of the caning to a feverish pitch. He frantically kicked his legs with each stroke while the women situated behind him watched with spellbound arousal while they jilled themselves. After a sustained period of caning, Vanessa finally stopped. It took a few moments for the observers to compose themselves. Vanessa, of course, had jilled 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, Vanessa 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, Vanessa 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 Vanessa. 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, Vanessa stated, showing off the item to all the women. The harness had a rippled dildo-like attachment that the female inserts in her 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. Vanessa 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, Vanessa 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, Vanessa continued as they walked behind her bound boyfriend. Vanessa 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 grasping the bound male s hips with her hands, started to thrust the strap-on with hard, brusque strokes. UH! OH! UHH! OOOH! AAUH! UNGHH! he exclaimed as Bridget warmed up to her task. Bridget stopped momentarily for a shuddering climax. With a determined expression on her face, sometimes gritting her teeth, Bridget resumed her 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, Vanessa! 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 Vanessa released her boyfriend s binding straps and helped him up. Serving refreshments all around, Vanessa 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. Vanessa 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 Vanessa. 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, throbbing erection from the attention of all the women. After about fifteen minutes, Vanessa 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. Vanessa poured a generous amount of olive oil on her hands and applied it to his testicles and already rigid erection. The others followed Vanessa 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, but not beyond. At Vanessa 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, Vanessa nodded to them and silently mouthed the word okay . Vanessa slipped a finger inside his anus and messaged his prostate while Tori started to palpate his testicles and 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. Vanessa served another round of refreshments and the women washed up and got dressed. Vanessa told her boyfriend not to get dressed. As some of the women were getting ready to leave they told Vanessa 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 Vanessa 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 Vanessa, 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, Vanessa 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, Vanessa sleepily stirred, finding herself becoming slowly awake, laying on her tummy, being entered by her boyfriend. Her vaginal innards welcomed the fullness of his erect but pliant member as it nestled inside her. As the thrusts became increasingly brusque, Vanessa 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 started to moan…

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