Sissy Prudence Part 2
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Sissy Prudence Part 5 free porn video
Sissy Prudence (Part 5)
(by Sissy Caroline)
Section 1
It had to be measured perfectly accurately and it was. The two halves
slipped together easily and the joins were virtually invisible. About a
half inch wide and a quarter inch thick, the collar now fastened
permanently around the sissy's neck was gold in appearance and as
difficult to cut and remove as the collar that had been fastened around
his scrotum some time ago. A small silver panel glued to the front was
engraved with his name - Sissy Prudence.
Strapped securely in the discipline room to the bench there was no
possibility of him avoiding the collar being locked around his smooth
sissy neck. All the Mistresses were present at the time, but it was
Mistress Jennifer, his mother, who was the Mistress who put him in what
was to be permanent bondage. Although he wondered if his disobedience
had caused this to happen, it was made clear that this was always to be
part of the process.
He was horrified. How could he ever go out now because everyone would
see his collar and his sissy name? When he was freed and alone in his
cot that night he tried to see if there was any way the collar could be
removed. He soon found it couldn't and he was more agitated than ever,
so much so that Mistress Jennifer heard him on the baby monitor and came
in to see him angry and sitting up about to cry.
She put him in another collar and leash and took him into her room, and
put him into her bed. "Face the edge of the bed sissy - lie on your
side."
He did as he was told and then he felt Mistress Jennifer move up behind
him and put her arms around him and inserted a finger into his mouth,
allowing him to suck on it while he settled, and all the while kissing
him on his neck. He soon calmed down and relaxed and went off to sleep
peacefully.
Section 2
"That's fine Jennifer. Leave him with me while I put him away so we can
discuss the final details of his program for the next month."
Prudence was dressed in a simple light blue cotton outfit that came to
just above his knees. It had short sleeves and with short cream socks
and 2" light blue heels he looked very 'little girlish' as his mother
liked to say. As usual he carried a small handbag with his makeup and
his hair was very simply styled with a blue ribbon tied in a bow on the
right side. His permanent collar contrasted nicely with the blue lace
collar of his dress and gold bangles on each wrist emphasised his
femininity.
The drive had taken nearly three hours and he was in nappies and light
blue transparent plastic panties that just showed occasionally under the
hem of the dress. He was wet but there was no external evidence of that
as he was always thickly nappied when away from home. Mistress Kathryn
locked a wide leather collar around his neck, attached a leash and led
him away. A short time later she was sitting with Jennifer having a
drink and discussing the immediate future for her sissy.
"He is safely locked away Jennifer and I suggest that you leave without
seeing him again. That will help him to recognise very quickly that he
is mine for the next month. He turns 15 then doesn't he?"
"Yes. Fifteen, just a few days after I take him home."
An hour later Jennifer was on her way home and Kathryn walked down
through the house and into the basement to check on her new charge.
While she was very experienced at disciplining and training males of all
ages, she had never before been in charge of a sissy. She was looking
forward to exploring this new world. She looked at him lying curled up,
naked and hooded, in the small cage that would be his 'room' for the
entire stay. The leather hood she had locked on him did not allow him
to see and it also was padded over the ears to prevent him hearing
anything in the outside world. She often used this technique of sensory
deprivation on her other inmates when they first arrived - it separated
them from their immediate past and made them concentrate entirely on
where they now found themselves and think random and confused thoughts
about what might happen to them. Experience had taught her that this
was a powerful tool and she intended that he would be kept this way for
at least 24 hours receiving only simple food and water every 6 hours.
The inevitable mess caused by his confinement in this way was readily
washed off the rubber floor and his inability to control even his bodily
functions would increase his anxiety and humiliation. He was to learn
that disobedience of the type he had displayed to his mother about going
out in public was unacceptable. He was a sissy who would do as he was
told at all times.
She only glanced at the three other older inmates who were in their
cages for the night. They could see her but knew better than to say
anything. One was leaving the next day and she expected his wife to
pick him up around 10.00am. The other two were here for weeks to come -
their wives were away travelling overseas and were just pleased to allow
someone to have the responsibility of keeping them for a while.
Section 3
Released from his cage late the next day, Prue was disorientated and
concerned about what was happening. He was clean again and his hood had
been removed, but he was still alone and this time chained to a point in
a large room that was nicely furnished with polished floors with
scattered rugs. He was absolutely naked.
Off to his right he heard someone enter the room so he looked around to
see Mistress Kathryn enter, the stiletto heels of her long leather boots
sounding ominous on the wooden floor. She had two men following her on
leashes, both also naked and heavily chained hand and feet.
"Look at the floor Prue. How dare you look at me without permission.
No wonder you are here to learn some discipline."
She walked to the front of him, the two men shuffling uncomfortably
behind, and struck him on the left buttock gently with her short whip.
"Perhaps I should whip you for your insolence Prue. Maybe later after I
have dealt with these two."
She chained both of them to a stand at the far end of the room and for
the next half hour used the whip on each of them until they were
sobbing. Their bottoms were a mass of red welts and Prue feared he
would be next. He had never seen anything like this and was terrified.
She left them chained and walked back to him, her boots echoing on the
floor and her leather crackling lightly with each step.
But she did not whip him. Instead he was released and she pointed at
her boots. "I am told that you are good at licking boots Prue. Prove
it to me."
"Good boy. Now kiss the inside of my thighs and my leather panties.
Smell me. Smell my leather. Smell your Mistress, the one who controls
all of you slave."
She watched him come erect as he did as he was told. "Sit back for the
moment darling." He sat back on his knees with his head bowed and
waited for her next command. She walked around behind him and used a
steel shackle taken off the wall to lock his feet together. Back in
front of him she ran her fingers through his hair and gently lifted his
chin, indicating that he should kneel erect again.
"Take my leather panties off darling - there is a clip on each side to
release them."
His hands were shaking as he unclipped them and put them on the floor
next to her boots.
She put one hand behind his head and pulled him forwards, guiding his
mouth to her and gasping as he kissed her gently before starting to
insert his tongue inside her. She was surprised by how sensual he was
in his approach to her - not awkward or stumbling like so many males,
but tender and careful and caring. She knew that he had this side to
him, but the passion that flowed from him to her surprised and delighted
her.
He began to tremble as the effort of kneeling as he was began to tell on
him, so she allowed him to put his arms around her which had the added
effect of bringing them even closer. Time and again he pushed his
tongue inside her and she began to sway against him, feeling him more
and more excited just as she was. She spoke to him quietly. "Lick me
my darling Prue. Learn what it is like to be a real sissy who has no
other objective in life other than to please his Mistresses. Lick me
and understand what it is like to truly serve, to be a slave, to be
obedient and under control and to be rewarded for your devotion."
Her orgasms rippled through her body again and again until she could
take no more and pushed him away from her. She allowed him to settle
down before leading >from the room back to his cage where she put him
back in the hood before locking him into his chastity belt. "We can't
have our little sissy playing with himself over night can we" and he was
locked him away for another 24 hours.
Section 4
He waited with Mistress Karen at the door of the large room as he had
been told. He could see the two men, naked, in stocks near one wall
facing into the centre of the room, and he knew that she had whipped
each of them again recently because he had heard the slash of the whip
and their whimpers as he waited outside the door. It seemed that they
were whipped every day but he did not know what else happened to them
because he only ever saw them like this.
He met Mistress Karen for the first time that morning and she helped him
get ready to meet Mistress Kathryn in the play room. He shivered as he
stood there, not from cold but from anticipation. Mistress Karen must
have been in her mid 50's, he judged, and she was really very gentle
with him as she helped him bathe, do his hair and makeup and dress - if
dress was the right word to use this time. The theme was cherry red,
and his lips were full and thick with a glossy cherry red lipstick, his
strappy 5" stilettos were the same colour and his toes were beautifully
manicured and painted.
Around his neck was a posture collar made of cherry red vinyl with a
cream lace fringe and this collar was matched by garters high on each
bare and oiled thigh. Little gold thimbles were clamped onto each
nipple and from them dangled a little gold chain with a bell on the end,
and these were matched by long gold lace earrings that dangled close to
his bare shoulders, and gold chains around each wrist to which were
attached small bells as well. Around his waist was a red vinyl belt
about 4" wide that sat nonchalantly on his hips and it held gold chains
that outlined his pubic area and his sissy bottom. He was fully plugged
and from the end of the plug black vinyl ribbons fell to the back of his
knees like a tail. His scrotum was enclosed in a small vinyl bag with
lace fringes and it had been drawn tightly and a bow tied in front.
His penis was erect, and kept erect by the red rubber band Mistress
Karen had fitted over the base after ensuring he was erect, and behind
the head Mistress Karen had tied a red bow - it was the last item she
put on him and she tied it tightly. He held a small handbag of the
right colour in his left hand, and his right arm was close by his side
but his hand was bent a little backwards and outwards as Mistress Karen
had taught him. But perhaps it was his eyes that finally drew attention
- long heavily mascara'd lashes and smoky eye shadow and thick bands of
eyeliner gave him a look that was hauntingly sexual, particularly with
his short hairstyle that had been brushed to one side. When he had seen
himself in the mirror before walking out to await Mistress Kathryn he
was stunned at the picture he presented. At nearly 15 years of age he
was slim, and about 5'10" already - but his height just added to the
ambiguity and then the understanding that this was really a boy who
wanted so much to look like a girl.
"Come in Prue darling. Walk to your Mistress like a good boy."
He hesitated briefly before Mistress Karen gave him a quick slap on his
bare bottom, and he stepped into the room and walked with what he hoped
was a girly style towards Mistress Kathryn. She watched him with
delight - he was absolutely sexy and his bells tinkled and added to the
sound of his heels on the bare floor that echoed throughout the room.
He reached her and then cast down his eyes waiting for her command.
"Good boy. You look very nice and your walking was really quite good.
Tell me how you feel darling."
"I feel good thank you Mistress," he said still looking down at her
booted feet.
She touched the end of his penis with her whip and watched with delight
as it and he twitched and his bells tinkled with the movement.
"Walk around the room for me and I then want you to stand in front of my
two slaves."
Two minutes later he was standing in front of the two slaves in the
stocks, and noticed with alarm that they became erect when he got close.
Mistress Kathryn then came over and whipped each of them while he stood
there and watched with fascination. Then without a word she indicated
for him to bend over. She took a cane from the wall and hit him hard on
the bottom. "It is about time my boy that you got used to this cane.
It is not that you have been disobedient to me - yet. But this is part
of the punishment for disobeying your mother."
She gave him four more strokes and at the end he was almost in tears and
he was sure he would be marked. "Now lick my boots you little sissy
boy."
The cane became a part of every day that he remained at the facility,
even Mistress Karen used it on him when he was slow to react to Her
command one morning, and despite the pain he was surprised that there
were times when he became erect at night just thinking about one of his
Mistresses using the cane on him when he was back home. What was wrong
with him?Section 5
"Mistress Kathryn tells me that she introduced you to the cane my
darling. Did you like being caned by Her?" They were in the car on the
way home and as usual Prue was belted into the back seat in his thickest
nappies and plastic panties so he would not cause a mess on the drive.
"No Mistress. It hurts.""Well then. You know what to expect in future
if you disobey me don't you, and when you return in a few months to
visit Mistress Kathryn again I am sure that she will have some new
treats for you beside the cane."
Prue just sat still and said nothing. He was caught up in his thoughts
of the pain of the cane and the erotic excitement of being naked and yet
pretty, and then licking her boots, as he was on that day when the other
two slaves were beaten in front of him. He was dressed in a pretty
cream and lemon baby doll outfit and as he thought of that day he played
rather absent-mindedly with the ribbon on his breast. Before he knew
it, the car was stopping and his door opened.
"Get out."
Mistress Jennifer pulled him from the car and put attached a leash to
his collar. "Come with me you insubordinate, disobedient little boy."
He looked around quickly and was relieved to see no one was walking
nearby, but he hurried behind her into a nearby park where she made him
bend over while she used her strap on his bare upper thighs. "Do not
ignore me again when I am talking to you. Do you hear me?" She was
furious. "Perhaps I will take you back to Mistress Kathryn right now
for a caning and just leave you there for another month. Now kiss my
boots and apologise."
Eventually her anger dissipated and she allowed him to stand properly
and then looked directly into his wet eyes. Some mascara was running
down his cheek in his tears and she immediately regretted how severe she
had been, but of course she did not let on. "Back in the car now and
behave yourself or else I will do this again before we get home. Clean
yourself up and fix up your makeup before we start." Prue opened his
handbag and took out some tissues and his makeup and quickly dabbed his
cheeks dry and powdered them before retouching his mascara and his
lipstick. His mother watched him in the rear view mirror and was
pleased with what she saw. Her son really was coming along nicely as a
sissy, and doing his makeup and keeping it fresh was becoming second
nature to him.
When they arrived home he was put to bed immediately without a meal but
after a severe spanking from Mistress Janice, who was really quite
pleased to see him. She had missed him and his oral talents.
In the morning came he was surprised to see his mother come into the
room and sit beside him on the cot. She didn't say anything at all, but
just stroked his hair and face for some time and occasionally she bent
over him to kiss his cheek. After a few minute she felt inside his
plastic panties and knew immediately he was both wet and erect. "Stroke
yourself for me darling. I want you to release for me into your
nappies. I think my boy need to release after such a long time doesn't
he?"
He convulsed as he stroked himself as ordered and he sucked on Mistress
Jennifer's fingers as she put them near and then into his mouth, and
finally came with moans of pleasure. Mistress Jennifer put a finger
inside his nappies and found some of his slippery white fluid before
placing her finger back on his lips. "Clean this off me please darling
like a good boy. It is about time that you tasted your own cum and from
now on expect to taste it every time you are allowed to release."
He took in her finger cautiously at first but then did as he was told -
it tasted salty and bitter, but he supposed like so many other things he
would adapt quickly to this new demand.
Section 6
"My goodness, we do look cute today."
Prue was in a grey pleated skirt coming to just above his knees, and
with cream stocking and grey 3" pumps his legs looked very shapely
indeed. Over his lacy bra and satin slip he wore a simple light blue
mohair sweater with short sleeves that emphasised his bust line. His
hair was nicely brushed and held in place with spray and on his right
side was a beautiful blue clip that kept his hair back behind his ear
even though it was still reasonably short. Simple gold studs in each
ear, grey eye shadow, heavy mascara and rich pink lips set off the
simple nature of his outfit quite nicely. The light pink nail polish he
had used was also just right for his outfit and while his mother would
not have used the gold bangles, she was generally very pleased with him.
It was the first time he had ever been given the choice of what to wear,
and she knew that he would be conservative because he had been told they
were going out for the day, but he had chosen well. Under his skirt he
was plugged and in his chastity belt and over the belt he wore for the
first time some new ultra thin and very absorbent nappies covered by
tight fitting plastic panties. He still wore some nice frilly white
panties and a garter belt over the nappies and it all seemed to fit
comfortably on him. There was no way that he would be allowed to go out
without nappies on - certainly not at this stage of this training.
As he walked towards her, she could smell the exotic mixture of his
lavender scented powders and deodorant with the new perfume from
Mistress Anne. He walked with confidence and poise and as he reached
her she took his hand and pulled him towards her to kiss him on the
cheek. "You look beautiful my darling, and don't worry about today too
much. We need to do some shopping for you first and then we are off to
the beauty salon to get your hair styled properly so I can start to let
it grow a little longer."
Although his mother did all the talking, for which he was very grateful,
she made sure that Prue was responsible for selecting his new bras,
panties and stockings as well as a night gown and some ribbons for his
hair. She was pleased with him and made it obvious as they drove to the
beauty salon. "See, it wasn't so hard to go out dresses after all was
it darling?" "No Mistress." The truth was that Prue's heart was still
racing from the experience and he was sure simply everyone knew he was a
boy dressed as a girl. Everyone.
At the beauty salon he was shown into a room to the rear by Mistress
Serena, as he was told to address her, and soon seated in a big
comfortable reclining chair. As soon as the plastic cape was placed on
him he blushed. Mistress Serena noticed it all immediately but said
nothing as she had been fully briefed by Mistress Jennifer on her son's
fantasies and desires. For more than two hours he was primped and
pampered. His hair washed, styled and set, his nails trimmed and
polished and eyebrows shaped and his makeup redone. At the end he
looked very sweet and Mistress Serena, given the chance, would have
taken him home with her there and then. He was tending to have that
effect on females nowadays.
When he was allowed out of the chair at last he was told to serve tea
for both Mistresses in the lounge room. After doing so Mistress Serena
was delighted to see him sit down near the feet of Mistress Jennifer
who, almost without thinking, took his collar and leash from her bag and
put it on him. "Sissies need to be controlled like this Serena. You
will see that Prue is still learning to be a good sissy, but he has
taken to the collar and leash and he just loves being harnessed and
taken for walks by Mistress Anne. You should come out for his birthday
party tomorrow and see him in his own environment. Bring Suzy if you
wish." She saw Prue shudder at the thought of Suzy, whoever she was,
seeing him as a sissy.
(end of Part 5- To be continued)
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- 19.10.2021
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