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 corporal 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 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!" as 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 whipping 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 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

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. Jenny 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. 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," 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 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. 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! Jenny!", and "Please stop! Please stop!", "OH!

Jenny, Please!" accompanied his writhing motions. The ladies'

expressions of their climaxes were becoming more prevalent as Jenny

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, Jenny finally stopped. It took a few

moments for the observers to compose themselves. Jenny, 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," 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 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. 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 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 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, but not beyond. 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 most of the

women.

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, 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, 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

started to moan...