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The Prisoner - Chapter 91

From: Boz 4444
Date: Thu, 29 Nov 2012 10:11:17 -0000

The Prisoner, by Will Cane
Chapter 91

The previous episode, Chapter 90, is at:-

James spent a nervous few hours lying on his small bed. He had
no idea what would be happening other than the assessment day
had something to do with it. He gently felt his buttocks and
hoped that their tenderness following last night's beatings
would not be made worse.

At the appointed hour he was waiting for the driver who greeted
him politely being just about the only member of staff who
hadn't been informed of his new status. The drive was for nearly
an hour and the driver not receiving any encouragement to talk
from James, it was carried out in silence.

He was dropped off in the street of large white town houses that
has obviously housed the upper classes for many years. He
climbed the flight of stone steps and stood in front of the
imposingly large blue painted door ringing the door bell.

Following a pause the door was opened by a tall fair haired girl
in her mid-twenties dressed in a form of school girl uniform of
skirt, blouse and tie.

James muttered his surname and remembered to add a polite

To his surprise the girl gave a wide grin and invited him
inside, leading him along through a large hallway into a small
reception room. She indicated that he was to sit on one side of
a small table and she sat on the opposite side. She introduced

"My name is Anna... but you had better call me Miss Anna in this
place. It's my job to prepare you for what is to happen later.
Now Hough, has anyone told you what you are here for?"

He replied that no one had, which seemed a cause of some regret
to the girl.

"Oh dear... then I will have to break the bad news... you see
your wife has agreed to Madam McKenzie, who owns this house,
giving you what she calls an 'Introductory'. Now I read from
your file that you already receive 'Maintenance Beatings'...
well Madam will lay on a more severe thrashing to make you
totally aware of the authority of females and what will happen
should you fail any part of the training that you now have been
scheduled for. I had better warn you that this will probably be
worse than anything you have experienced so far and indeed is
designed to be. Whether you will have to come back for further
punishments will be up to you but I truly believe that you will
do everything to avoid such a return visit. I have to tell you
that Madam believes that the cane is the best implement to use,
that you will be naked and that there will be witnesses that you
cannot object to. Basically Hough... this is going to be hell
for you, but if you accept it with anything less than total
obedience, Madam can... and will... make it far worse for you.
Do you have any questions?"

"When will it happen Miss?" he enquired respectfully.

"In around an hours time, but first I have been told that I have
to perform a certain service on you. You see the form completed
by your owner has the box ticked that requires you to be milked
before the beating. This is to ensure that there is no sexual
endorphins in your system that would make the beating seem less
severe. I'm sorry... I know it will be humiliating for you, but
it has to be done and done really thoroughly until you are
really drained. I will do my best to make it as pleasant as
possible for you as I know just how you must feel."

The look on James's face indicated that he thought this comment
was just so much mock sympathy, he had become so accustomed to
the cruelty of some women in recent times.

Anna stood up with a look of annoyance at his scepticism. "Why
do you think I am wearing this silly uniform James? You are not
the only one that Madam has here for training."

Without any embarrassment she turned, raised her schoolgirl
skirt and pulled down the large pair of dark green uniform
panties. Her buttocks and upper thighs were a mass of heavy
bruising, most of which were in horizontal stripes.

James did not need to be told that she had been thrashed as
severely as he was apparently about to be.

She explained: "This happened three days ago so I'm still damned
sore. My owner-husband authorised it so, like you, I just had to
accept it without question. Believe me... it hurt like hell and
no one offered any sympathy. It's something that people like us
just have to learn to accept and work through. For me the
humiliation was nearly as bad as the pain."

Anna was soon taking advantage of a sympathetic ear, "Madam
McKenzie has made sure that the frame to which you will soon be
strapped with your backside up in the air exposes the victim and
leaves nothing to the imagination... particularly when it
happens to a female like me. You just know that her audience are
staring at your most embarrassing bits and you just have to
blush and accept it. Afterwards, even when the pain was still
peaking, I was more concerned about the rough handling that the
people were encouraged to do as they 'examined' the punished
area with their fingers."

She replaced her panties and skirt. "Let's get the milking over
then Hough. Follow me please."

She led him down the stairs into the basement area. They walked
past a door from behind which he could hear voices.

Miss Anna screwed up her face and whispered with some disgust
that they were the witnesses starting to assemble. They entered
a white painted room with a sink and toilet and she closed the
door behind them.

She then asked if he had been milked before and when he
mentioned Mrs Brady's ministrations he had to explain, in
detail, what she had done and how she made the event as
unpleasant as possible.

Anna smiled and told him that he would find her methods more
than pleasant and told him to strip and lay back on a medical
type raised bed which was covered in a white sheet. She turned
her back as he stripped and she donned a pair of blue latex
gloves. As she turned back towards him she told him to lay flat
with his legs wide to give her the necessary access.

Anna then reached over and gently held his slowly erecting penis
with her left hand. She slowly pushed his foreskin down to
expose him and gasped with horror at the state of his glans, red
and sore from the recent attentions of Mrs Brady.

Wincing, James explained how it had been caused by the cruel
restrainer he had to wear and the abrasive cream that had been
used for his earlier milking.

James wasn't used to receiving kindness from a female, having
suffered only cruelty for quite some time now, and he was most
touched and relieved when Anna produced some cold soothing
ointment and proceeded to rub it in to the raw skin. It soon had
the secondary effect of hardening his penis further which Miss
Anna seemed to find amusing rather than offensive.

"I have to prove that I have milked you Hough, so when you spurt
it will have to be in the glass jar so make sure you don't

She then lightly held his scrotum in her left hand and then
started to slide her right gloved hand up and down his shaft
greatly aided by the slippery cream.

Anna certainly knew what she was doing. Long strokes were mixed
with short ones that concentrated on the glans. All the time she
was watching him for signs of approaching success and when the
time came she increased her hand action considerably until his
back arched, a long groan came from his lips and with the jar in
place whilst she continued pumping the organ, his ejaculate was

Anna then firmly squeezed the length of the shaft until all the
sperm had been squeezed out and extracted, she scraped the glans
with the rim of the jar to collect the last drops and moved away
from him.

There was another surprise for James. Anna picked up what was
obviously a house 'phone and spoke to "Madam" explaining that
the milking had been done and asking would she care to inspect

As the answer was clearly yes she quickly put the 'phone down
and told him to stand with legs apart and hands on head for her

It took just two minutes for the door to open and in "Madam"
walked. She was in her early forties, short with heavy hips and
a pronounced bosom, dressed in a white shirt with long sleeves,
a short black skirt and her dark hair in a long pigtail hanging
down her back. Her face was not unattractive but was devoid of
any humour. Her large eyes were gray and stared menacingly at
her next victim. She picked up the sample jar and spoke to Miss

"Are you sure you have collected it all girl?" Madam enquired.
"I don't want any embarrassing stiffies when he is paraded
before my guests and most importantly I want him to feel the
full force of the caning."

With that she placed the jar on the side bench then suddenly
grabbed James's flaccid penis with her hand. "Any life left in
this thing boy?" she demanded.

James managed to control his fear and stammer "N..no Madam

"We shall see... we shall see." With that she ordered Anna to
remove her tie and school shirt.

The girl looked amazed but rapidly did as she was told taking up
the same position as James but facing him when instructed. Her
white bra provided some privacy but still left her breasts
partially exposed to his view.

Anna blushed deeply in sheer embarrassment as Madam McKenzie
gave her next instruction:-

"Right Hough, you have my permission to handle this female's
breasts as much and as hard as you want. You will start by
removing her brassiere. And you girl.... will accept this
treatment... unless you want another dose of the cane!"

James was initially frozen to the spot not believing what he was
hearing. He looked at Anna whose face was now crimson. She
looked down at the floor and said just two words: "Do it!"

He went behind her, unclipped the fastener and allowed the bra
to fall down from her breasts as she obligingly lowered her
arms. They were not over large breasts, but firm and pointed
with large pink aureole and pronounced nipples that rapidly
erected as the cold air of the room hit them.

James started by squeezing the nipples in each hand then placing
a hand under each one lifted and joggled them as if to assess
their weight. He had been doing this for a couple of minutes,
and greatly enjoying himself when he was ordered by Madam to
stand back and resume his original position. Madam reached out
and grasped his now rigid penis.

"So girl, you have fully milked him!" she snorted in disgust.
"When I have a male milked he is supposed to be incapable of
erecting for several hours. You will resume his milking and this
time, do it thoroughly. I want him ready for my guests to
inspect in thirty minutes. Should you fail to extract a sensible
amount of fluid I will simply substitute you for the boy on
tonight's punishment display."

As Madam stormed out of the room Anna glared at James. "You
stupid idiot, are you deliberately trying to get me thrashed
again? I will certainly milk you now and without mercy so get
back up on the table!"

She started her pumping without another word or any hesitation
and it was as furious as she was, believing that she now faced
more caning as a result of his lack of control. Her compassion
for him and his upcoming punishment had all but evaporated.
Either she produced evidence of his draining or she was for the
same treatment.

James was surprised how short a time it took. Perhaps it was the
harsh rubbing of her clenched fist, perhaps it was the sight of
her still bare breasts joggling and swaying just inches from his
face. Whatever the catalyst was he spurted for the third time
that afternoon and it was only Anna's quick reaction with the
jar that caught it.

Anna now gave every indication of her desperation to avoid more
of the cane. She continued to pump, now extremely painfully for
James in the hope of extracting more evidence for Madam. She
even told him to reach up and hold her breasts in the hope that
more stimulation would return the lost erection.

Eventually she gave up, cleaned the area around his genitalia
and called Madam on the house 'phone to tell her that he was now

Madam McKenzie strode in, checked the specimen jar and pointed
out to Anna that the real test would be whether the male
displayed any form of erection when he was presented to the
witnesses. Even if he was a masochist, she had no doubt that
once she started to cane him sexual excitement would now be

Madam McKenzie gave James a cursory inspection around his
genitals and produced a steel bucket telling him that from what
she had read in his wife's report about his lack of bladder
control, he had better relieve himself before punishment.

Knowing that a refusal would make the situation incredibly
worse, James forced himself to overcome his natural inhibition
to urinate in front of two females and released himself noisily
into the bucket which he then placed on the floor.

Madam McKenzie then told Anna to replace her bra and school
uniform and for both of them to follow her.

They were taken into a large room that clearly doubled as the TV
room for the house. James, ordered to stand naked at the present
position facing the audience tried not to look at what was
obviously a punishment frame made out of steel tubes with padded
leather supports for various parts of the body.

Sitting around in comfortable chairs were three couples ranging
from their early twenties up to their fifties. Clearly valued
friends of Madam they listened intently as she spoke.

"Thank you all for giving up your valuable time to attend as
witnesses. You will no doubt recognise the female, albeit from a
less embarrassing angle than when you last saw her on the
punishment frame....."

A soft titter of amusement went round the room.

"...As you know she was caned at the request of her husband in
the hope of improving her general behaviour, which I hear it
has. I thought that you would be prepared to have her here
tonight for two reasons. Firstly she has been used to thoroughly
milk this male to ensure that there was no residual sexual
interest in being beaten but also so that you could see the
natural progression of the extensive bruising that was a
necessary result of her thrashing...."

At the mention of the milking one of older members of the
audience gasped, presumably surprised that Anna would be ordered
to do such a thing to a stranger....

"You eagerly went to great lengths to examine the weals and
ridges that the cane creates and now you can see the results
after just three days. She tells me that the bruising is still
rather tender to the touch, but you can disregard that
information if you feel that it will prevent you from carrying
out a thorough inspection. Strip girl, leave your clothes on
that stool and mount the frame," Madam McKenzie ordered.

Anna stood rooted to the spot. She had been given no notice that
she would again be humiliated by the group and that she would
have to strip in front of them. Her face was bright red and her
jaw was hanging open in shock. It was only a further sharp
command from Madam that made her move.

Mechanically she removed her tie, shirt and skirt, then her bra
followed and she slid her school type knickers to the floor.

Madam interrupted the stripping to tell her to leave the heavy
school stockings and garter belt in position.

Anna then climbed slowly on to the frame. It required her knees
to be well spread with her upper body stretched out to enable
her lower arms to lay on their respective supports that were
somewhat lower. This had her hips and buttocks as the highest
part of her body and not only sticking skywards but obscenely
spread so that the hairy anal cleft and vulva were totally
exposed. Her breasts hung under their own weight jiggling with
every movement she made. A discreetly hidden light in the roof
somewhere lit the intimate area so that not a hair root, wrinkle
or blemish could go unnoticed.

Madam then asked if any of the witnesses would care to carry out
an inspection of the girl to fully appreciate how effective the
punishment they had witnessed had been. The youngest couple
stood up and approached. The male eagerly placed his hands on
the buttocks and rubbed the bruised areas vigorously making Anna

The girl, a rather superior looking chubby brunette by the name
of Miss Callum took a pair of latex gloves from the box on the
nearby table and, having donned them, also stood close to the
displayed female asking:-

"When you gave us that most informative talk on administering
corporal punishment you mentioned that some receivers display
signs of sexual interest during the floggings Madam. May I check
this person for any signs?"

The girl knew full well that the form completed by Anna's
husband had been thoroughly ticked in all the boxes that
indicated how his wife was to be treated. Items such as "Own sex
handling" and both the verbal, handling, exposure and duties
under the "Humiliation" section were ticked.

As many of these experiences as possible would need to be forced
on the female to keep her owner satisfied with the way she was
treated. From the continuing deep blushing of the girls face
that extended down to her breasts, this particular humiliation
had been selected by her husband because of her fear of such

Madam assured the witness that a penetrative check would be in
order but perhaps they would all first like to see the video of
her thrashing that was taped at the request of the girl's

Anna was then ordered to stand next to James and in the same
position, then they were both told to face the large projection
screen as the lights dimmed and the video commenced.

- - - - - - - - - - - - - - - - - - - - - - - - -

On screen Anna was seen being escorted into the room by Madam
McKenzie and was soon strapped down over the frame with the
cameras, hidden in the roof and walls of the room, taking in the
indecent display of her intimate areas.

Madam produced a long cane that was to be the instrument of her
correction and this was handed round witnesses for their
examination and approval. Finally the cane was handed back to a
young male who had appeared and seemed to be an assistant.
Having swabbed Anna's buttocks thighs and cleft with a large wet
swab of some sort he ran the length of the cane through the swab
as part of some antiseptic procedure.

Madam then grasped the cane, flexed it between her hands several
times, took up a position to the rear and left of the girl and
raised the cane back over her right shoulder bringing it down in
a whistling arc to strike across the upper part of the stretched

Anna could be heard to gasp and she strained in a futile way
against the straps that held her to the frame. Madam had clearly
carried out such thrashings many times before and made each
stroke count with around thirty seconds between each one to
allow the pain to be absorbed.

The strokes gradually made their way down the buttocks until the
last four of the fifteen stroke flogging were laid, with some
difficulty because of the wide spread, across the tops of the

The witnesses then came forward to carry out a visual and
tactile inspection of the still trembling buttocks and thighs.
Anna could be heard sobbing as various hands and fingers were
run over the swelling ridges often making the pain worse.

The edited video then ended with the area being swabbed down by
the male assistant.

- - - - - - - - - - - - - - - - - - - - - - - - -

Anna was ordered to take up the position on the frame once more
and Madam McKenzie told the female witness to carry out such
examinations that she considered necessary.

Miss Callum started by slowly cupping her left breast in the
purple latex gloves and gently lifting and swaying the weighty
item. Then, to emphasise the victim's vulnerability she dragged
her finger tip down the exposed anal cleft from the top to the
split of the vulva.

Next she toyed with the brown wrinkled anus, firstly gently
rubbing a finger tip around the rim and then suddenly jabbing
the finger tip at the very centre making the girl gasp and
thrust her hips away. Then, slowly but firmly, she used her
fingers to part the girls outer secret lips and then inserted
two fingers into the opening.

It seemed to hurt the girl and she emitted a whispered whimper
at the intrusion but knew better that to object to this crude
violation. Her husband had permitted any female contact and she
would just have to accept it or face worse punishment.

Eventually, after much probing and twisting the gloved fingers
were withdrawn and Miss Callum, carefully inspecting the gloved
fingers of her hand announced that she could see no indications
that the girl had found any sexual satisfaction from watching
the video of her beating.

Anna, with tears running down her cheeks from the humiliation,
was told to take up the same position as James and stand next to

Madam McKenzie spoke:-

"Thank you for your patience ladies and gentlemen. We now move
on to the main event for today which will be carrying out this
male's wife's request that he be given a beating that he will
not wish to have repeated. If you, Miss Callum would take a seat
next to the punishment frame I will be asking you to carry out
regular checks of this male for the slightest level of sexual
arousal during the session. He has, I am assured, been
thoroughly milked but one cannot assume that he has had all the
male semen drained...."

Madam McKenzie explained:-

"This beating is just part of a long training course for this
male during which he will be taught total obedience to female
authority. As well as having to accept the application of
punishment by any female put in charge of him, he will also have
to reach a high standard of personal service to any female that
he finds himself in the company of. Any ideas that he has any
choice to whom he offers servitude to, or any choice in the
nature of that servitude will be either trained or beaten out of

Addressing herself to the women in the room Madam McKenzie
proudly announced:-

"The eventual standard of service, ladies, is that when fully
trained, he will, without question or hesitation, obey any order
that you might give him. He will always carry out any, shall we
say more personal service, that you may find enjoyable to any
area of your body and at any time or place that you decide...."

James was finding it hard not to tremble with his fear as he
listened to the explanation of his fate, and wondered how these
monstrous people could possibly imagine he would become aroused
by the treatment he had just see Anna suffer on screen.

"All the time he will, after this evening's discipline, have in
the back of his mind what will happen to him if he fails in any
way to be obedient or does not comply with personal service to
the standard the lady requires. He will, I can assure you, be
very mindful of his need to show total respect to any lady."

James was then ordered to mount the frame. He immediately felt
the shame and sympathised with Anna in the way his thighs were
required to be widely spread and his back lowered so that his
already bruised and sensitive buttocks were forced high in the
air. He obviously could not see how he looked to the witnesses
but could feel the cold air around his opened anal cleft and his
dangling genitalia.

The numerous restraining straps with their Velcro grips soon
held him rigidly in place and he saw Anna's legs as she
approached. The cold swab being applied to his skin made him
gasp in shock especially when it was dribbled into his anal
cleft and stung his exposed anus. Both his thighs were wiped
removing any hope that they might not be struck.

Madam McKenzie was heard to remove an implement from the wall
rack and she then held it in front of his lowered face. It was a
different one to the one used on Anna in that it looked a little
meatier and slightly less flexible. It still bent as Madam
flexed it under his nose.

"Take a good look James". She whispered. "I have selected a cane
that you will really feel and come to respect as it will now be
necessary to really hurt you. I have no objections to you
vocalising the pain but I would warn you that if I hear any
insults or obscenities coming out of your mouth you will be
gagged and an extra set of strokes awarded. Extra strokes will
also be awarded if Miss Callum here detects any signs of sexual

Madam McKenzie stood back and held the cane out so that Anna
could wipe it's length with the antiseptic swab. She then took
up a position to his rear and his left, with Miss Callum taking
a seat to his immediate right.

Miss Callum immediately reached under him and gripped his
dangling scrotum firmly then his penis which she squeezed and
pulled none too gently. With some difficulty she forced his
foreskin back to expose the raw area which she continued to
squeeze and pull hoping to achieve some inflation.

James heard the swish of the cane behind him microseconds before
it struck across the top of his buttocks. It was harder than
even the strokes he had been given during assessment and his
immediate thought was of how many like this would he receive.
The pain of the thin weal hit him soon afterwards and caused as
much fear as sheer pain itself.

He knew only too well that he was now entirely at the mercy of
this woman, he would be given as many strokes as she thought
fit. There would be nothing he could do to change that in any

- - - - - - - - - - - - - - - - - - - - - - - - -

To be continued.

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