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 The Story of Jenny (part 6 - Jenny and the Jill Club - F/M spank)

   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 the administering of 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.  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 silly 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!" 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 strapping 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 felt excitement 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.  She 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.  She came back holding 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 bottom, so that it extended past
them for a few inches.

   "Oh, Jenny, no!" he plaintively and sincerely pleaded, knowing that his
fearful anticipation aroused her, and probably the other women.

   Within a few seconds Jenny commenced striating his already strapped
backside 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.  This was apparent from his reaction.  He kicked his legs,
he vigorously jerked his head 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 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!" he groaned 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, and produced 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 struggled
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...

   ---- I hope you enjoyed this story.  I enjoyed writing it.  This work is
copyright by the author.  Commercial use is prohibited without permission.
Archiving and reposting of this story unmodified is permitted provided that
no fee is charged, either directly or indirectly (including so-called
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original author (rick_oh at email.com) are maintained.  My other stories
can be seen at /~rick_oh/