Sissy Prudence Part 2
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Sissy Prudence Part 3 free porn video
Sissy Prudence (Part 3)
(by Sissy Caroline)
Section 1
"That's our Sissy Prudence in the garden. Isn't he a delight?"
Bridget looked out the window and, despite the fact that boys were not
really her interest, she found the sight presented to her was quite
exciting. She had never thought that a boy in a dress could be such an
erotic fantasy.
Prue was working in the garden, which was something he now really enjoyed
as a break from his duties inside the house. Not that he was allowed to do
any of the heavy work - that was left to the man who was paid to come very
month and mow, prune and generally tidy up. Prue looked after the flower
gardens that he had been told to develop and a good job he was doing with
a colourful display of annuals in a beautifully tended garden bed. Right
now he was kneeling on a cushion and doing some weeding although of course
he was wearing gloves to protect his hands and especially his now quite
long nails. He knew there would be hell to pay if he happened to break
one. His Mistresses had insisted that he grow them long and keep them
properly painted at all times, and of course he had already been severely
punished once for not painting his nails carefully.
Mistress Jennifer had bought him some special dresses in which he was to
do his gardening, all mid calf in length, with long sleeves as protection
against too much sun and very high collars. The one he had on today was a
dark and light blue floral dress with a skirt that flared just enough to
allow him to move freely. It was complemented by a pair of plain black
shoes with two inch heels and a broad brimmed hat that had light blue
ribbons on the edge of each brim that were tied together in a large bow
under his chin. Of course he wore make up as well with a light pink
lipstick making him look quite demure under the shade of his hat.
"My goodness, what a sight. He even moves a little like a girl would
move," said Bridget as she watched Prue stand, smooth out his dress and
prepare to move the cushion to a new spot to continue weeding. "Does he
have to wear female garments underneath as well?"
Alison looked at Bridget with a smile. "Of course he does my darling.
Right now he will have on one of his pink frilly bra, panty and suspender
belt sets and, as you can see, a pair of stockings. Of course while he is
gardening we try to keep things simple, so he is not required to wear
jewellery except for the single pearl studs in each ear. He wears them
also when he is doing maid duties as you will see later. Oh, and he has
some other, shall we say, devices on under the dress as well. His mother
has made sure that he is very secure until her return."
"So the Sissy does house duties as well?"
"Yes. It is an important part of his day to day life to ensure that not
only is he kept busy in a productive way, but that the thought that he is
here for the benefit of his Mistresses is constantly reinforced. He does
all the vacuuming and dusting and general cleaning, the washing and
ironing, the dishes, the making up of beds and he helps with preparing
meals. Our intention is that with time he will do at least some of the
cooking on his own. He is learning to do simple sewing jobs as well, and
the other relaxation he is given is learning to knit. I have to tell you
that it is hard to keep a straight face when you see his mother sit him
down in one of his frilly dresses and make him pick up his knitting
needles and practice. But he tries, because he knows that is what is
expected of him, and that he will be punished if he is found not to be
doing his best."
"So do you think you will move in here with me now that you have seen
him?"
Bridget leaned across to give Alison a kiss on the lips. "How soon can I
move in?"
Section 2
Mistress Jennifer and Mistress Alice moved in a week later and of course
Sissy was hoping to be released from the chastity belt immediately, but it
did not happen. Was he being punished for something he did or didn't do,
but he was too afraid to ask? It was three days later that his mother
released him with a big kiss telling him that she was generally pleased
with the reports she had received about his behaviour, and that perhaps he
would like to spend some time with Mistress Alison that evening.
"Do you want to play with yourself for Mistress Alison darling? She tells
me that maybe you would like to wear your plastic harem outfit and play
with yourself while she is with you. Is that correct?"
"Yes Mistress it is correct. I like my plastic harem suit and I haven't
been allowed to play with myself for a long time, so that would be nice
please."
"Well, I will allow it, but the trade off is that from tomorrow you will
be back in the belt for the next month until Alison and Bridget move in.
You know about Mistress Bridget coming don't you?"
"Yes I do Mistress, but I haven't seen her."
"You will Sissy. I suspect that you will get to know her very well. Do we
have a deal? You are allowed to play with yourself, but the belt goes back
on immediately after."
He hated the belt. It wasn't that it was uncomfortable or anything, just
that it made him feel so totally helpless and controlled. Perhaps he
should just say ?no', but in his heart he knew that he couldn't.
"Yes we have a deal Mistress."
His mother smiled, not surprised at all by his acceptance of the belt
again as a trade off for some release of his sexual tension. She told him
to bathe and then wait for her in his bedroom. When she came into his room
she was pleased to see he was kneeling facing the corner as he was
required to do. He was learning his place.
She said nothing and he did not move while she went to his drawers and got
out his plastic harem outfit, spreading out on his cot. From another
drawer she got an extra large plug that she had bought some time ago, but
had not yet used. She was unsure that he could take such a size at this
time in his training, but there was no reason that she shouldn't try and
fit it into him.
"Stand up and face me."
Prue stood and turned around but kept his eyes down, looking at the high
heeled black leather boots that his mother was wearing as part of her all
leather outfit.
"Lick them."
He dropped to his knees and began to lick her boots and as he did so felt
himself become very erect and oh so excited. She watched him with a great
deal of pleasure. He was obedient and submissive and in terms of his age
and experience they had only just begun. She wondered where he would be
when he was a year older, or even five years older as she watched him lick
with passion, caressing the heels with his tongue before continuing on
along the length of each boot, never stopping because he had not been
given permission to stop, and nor did he want too. He loved his mother
anyway, but he particularly loved being with her, and all the other
Mistresses in this way.
"Stop and stand up."
He stood before her, naked and erect but still looking at her feet. The
smell of her perfume excited him even more and he could see the strap that
she so often used on him hanging from her belt. He leather skirt was tight
and short.
"Bend over darling."
He knew what would happen next, but he was surprised by the size of the
plug that she started to push inside him.
"Relax your muscles. You know how this works. Relax so I can get this done
easily."
After what seemed like him to be an eternity, and feeling his bottom being
stretched like it had never been stretched before, the plug suddenly
slipped inside and he became aware that not only was it wider, but it was
longer than anything he had worn before. He felt her give it a final
little push and then adjust the flange so that it sat comfortably between
his buttocks.
"I hope that is comfortable Prue. Do you like your new toy?"
"Yes mother."
Then he felt the strap on his bottom - hard and hard again. It went on
until he counted something like 20 strokes and all the time he wondered
what he had done to deserve this punishment.
"Mistress Jennifer to you sissy. Try again."
"Yes Mistress Jennifer. I like my new toy."
She ran a hand through his blonde curls. "Good boy."
He felt her rubbing something on him and he soon became aware that she had
a cloth that was soaked in baby oil and that she was smearing the oil all
over him. Soon he was covered in a light film of oil, but he still stood
very still and looked at the floor or her feet when they were in his view.
Her heels were loud on the polished wooden floor of his bedroom as she
walked around him making sure that he was covered from his shoulders down.
He felt her offer him his plastic harem pants and soon he was inside them,
his lower body slippery inside the soft thick plastic that folded around
him. Next came the halter like top, before she moved away and came back
with a long sleeved vest that covered him entirely. It had a plastic zip
running up the back that she did up until the collar was firm around his
neck. He had never before been encased in so much plastic and the feeling
was incredible, but there was more to come. Plastic booties were fitted on
his feet and tied around each ankle. Plastic fingerless mittens were next,
and they were tied in place firmly around each wrist. Then, when he
thought that there could not be anything more for him to wear she fitted a
plastic hood on him fastening it firmly around his neck before adjusting
the gaps so that he could see and breathe properly.
"Get into your cot."
When he was in she locked his steel collar on him with the short length of
chain that meant he was forced to lie down. She then covered him with his
favourite plastic sheet before telling him to lie quietly on his back and
await Mistress Alison. She warned him that she may be some time, and that
if he played with himself before she arrived and gave him permission he
would be punished more severely than ever before.
She then put a dummy in his mouth and left the room, turning off the light
and locking the door as she left. She knew that there was no need to lock
the door in reality, but that the knowledge that it was locked and unable
to be opened from the inside would make him feel even more under control
than usual.
He lay in the cot quietly, occasionally moving slightly to adjust his
position or the plastic sheet that was close to his face. He felt his
hairless body clasped by the plastic and the sensuous feel of the plastic
as the oil allowed it to move easily across him. He knew he would get warm
quickly if he exerted himself at all, so he was careful to move as little
as possible, but he could still feel that delicious warmth build trapped
inside his plastic coverings.
He must have actually dozed off in his contentment because the next thing
he knew was that Mistress Alison was sitting next to him on the edge of
his cot and taking the dummy from his mouth.
"You have permission to look at me darling. My you must have been so
comfortable to go off to sleep like that. How do you feel in the plastic
clothes that Mistress Jennifer has put on you?"
"Good thank you Mistress."
She leant forward and kissed him full on the lips, while she unlocked the
pin that kept his collar firm around his neck. "Sit up next to me Sissy."
She kissed him again and ran her hands over his plastic pants seeing the
outline of his erection pushing against them as she moved her hand down
his thigh.
"Would you like permission to play with yourself Prue?"
"Yes please Mistress Alison."
"You have my permission, but you must not come until I say that you may.
Is that clear?"
"Yes Mistress Alison."
He touched himself through the plastic covering, feeling the mixture of
oil and perspiration allow his body to slide against the plastic in
numerous places as he moved gently inside it. She held one of his mittened
hands tightly while he used the other to play with himself and grow ever
more excited. "Put your head in my lap Sissy."
He curled up and lay beside her with his head in her lap, the smell of her
perfume and leather dress strong in his understanding of the environment
he was in. She took the plastic sheet and placed it over him, tucking it
in around his legs and body and felt him shudder with excitement at what
was happening to him. She too was aroused by all of this, and gently
lifted her skirt so that he could lie even closer to her with his head now
resting on her naked thighs.
"Kiss my legs Sissy."
Of course he did as he was told, and he kissed the tops of her thighs very
gently while she made it clear that he was to continue fondling himself.
"Does my Sissy need permission to come yet?"
"Yes please Mistress Alison."
"Soon Sissy. Keep kissing me."
Then finally she gave him permission, and after a very short time she felt
him shake and shake as the fluid spurted in great streams into his plastic
pants. She saw his face start to drip with perspiration at the effort and
she knew he would now be perspiring profusely inside his coverings, and
like all males, wishing now immediately to be free of all these things now
he had satisfied his sexual need. But she would not release him. She
replaced the locking pin on his steel collar, and told him to lie down
again on his back before she covered him again with the sheet.
"Relax darling. You will not be escaping from any of this just yet. You
must learn that my pleasure is what counts, not yours. That the pleasure
and demands of all your Mistresses come before anything that you may
desire."
She sat there with him and held one hand as he slowly settled back to
something like normality even though he was effectively her prisoner.
"Tell me how you feel Prue. Did you enjoy that?"
Prue assured Mistress Alison that he felt wonderful and he thanked her for
allowing him to play with himself, and before he knew it he had moved his
head to kiss her on the hand. Immediately he knew he had done something
wrong, but this time there were to be no immediate consequences.
"Taking liberties with any Mistress is forbidden of course Prue. I will
strap you later. Now I want you to play with yourself again - just for me.
She took his hand and guided it to his crotch, and still holding on to him
helped him rub himself gently and felt as he grew erect once more before
coming again and again, with her permission, and then lay back in
exhaustion on the cot.
Mistress Alison got up and took a babies bottle off the dresser, passing
it to him and telling him to drink. She then pulled up the side of the cot
and walked out locking the door after her.
After he had bathed the next morning Mistress Jennifer reinserted his plug
before locking him into the chastity belt, which was to stay on for the
next month.
Section 3
"He does need something that marks him permanently as a sissy Jennifer. I
know that you are sceptical about a tattoo or any further piercing at this
stage so I think that my suggestion is one that will work well for him. I
have seen it done on other sissies who have come here for belt fittings
and it works very well, with no complications at all for fitting the belt
subsequently. We know what size we need and I can have it made so you can
fit it when his belt comes off the next time."
"I think that we need to do something Janice, but are you sure that this
is okay in the long term? I don't want to create issues that we cannot
handle."
"It works dear, believe me, and it is something you need to do. He needs
something that is with him all the time to remind him of his status in
life."
On the morning of the day when Alison and Bridget were to move in Mistress
Jennifer, Mistress Janice and Mistress Anne all entered Prue's bedroom
while he was still safely locked in his cot. Without releasing him from
his collar they removed his plastic panties, wet nappies and his nightie,
leaving him naked and lying on his back except for the belt which he had
now worn for a month since his time in plastic with Mistress Alison, a
time that he had dreamt about more than once although the belt stopped him
from becoming too excited.
"The belt fits really well doesn't it", said Janice running her fingers
over the triangular steel plate covering his front and also the metal tube
that confined his penis under the plate. She ran one finger along the edge
of the plate to check that it was impossible for him to access himself in
any way and was pleased to see that it was working as it should, although
the waist band may need to be tightened just a fraction for the next time
as he was getting slimmer with the strict control placed on his diet,
along with the exercise regime they had in place for him. Prue shifted a
little as she played with the belt making him grow hard in the tube as he
watched the three Mistresses standing over him, all in their leather
outfits.
Mistress Jennifer then unlocked the belt and removed it from him, pleased
to see that it had created no problems despite the long period of use.
Perhaps it could stay on even longer next time she thought. She then took
the two halves of the metal band that Mistress Janice had organized to be
made. It was one inch wide and a quarter inch thick with rounded edges and
without saying anything at all she moved to fit it around Prue's scrotum.
Prue was worried by what was happening but he couldn't help but come erect
as Mistress Jennifer carefully positioned the two halves so as not to
pinch him, before pushing the halves together and listening to the
permanent locking mechanisms click into place. She was pleased with the
result. The sizing was perfect, as it had to be because to remove it would
be almost impossible without very specialised equipment such was the
hardness of the metal, and it was firm but not too tight, separating his
penis and testicles in a manner that would make him aware of the band at
virtually all times. A diamond tool had been used to engrave the ring with
his full name ?Sissy Prudence' and his birth date.
"There that looks so sweet on him Jennifer. I told you it would work and
there is no way he can remove it without some sort of specialised help,
although I must admit I know of no Mistress who has yet removed one of
these bands once it has been placed upon her slave or sissy."
Hearing all this Prue became very agitated, and without thinking he asked
why they had done this to him. Mistress Jennifer told him that it was just
a further part of his transformation to his new lifestyle and that he
would now be punished for speaking without permission before he was
prepared to meet Mistress Bridget for the first time. "Perhaps you would
like to carry out the punishment Mistress Anne?"
"I would love too. It is some time since I experienced the pleasure of
strapping his sissy bottom."
A short time later he was chained over the spanking bench in the
discipline room and receiving the 50 strokes of a ?standard' level
punishment. It was not such a great way to start the day, and at all times
he was conscious of the new symbol of his status as a sissy, especially
when he became erect and it tightened around him.
Section 4
When Mistress Alison and Mistress Bridget arrived to move in it was Prue
who was required to open the door and greet them. As usual he was
concerned that someone else would soon know that he was a sissy, but he
was also concerned that he presented himself in an appropriate manner.
He was dressed in a pink satin outfit that Mistress Anne had bought for
him especially for this occasion. Anne had put him into one of his
tightest corsets and a soft pink bra and panties which had cream lace
ruffles all over the bottom. The dress had long sleeves, puffed from the
shoulders to the elbows, but then fitting more closely to the wrist where
cream lace fringes extended over his hands to some degree. The skirt was
nicely flared and came to just above his knees to expose the multiple
layers of petticoats giving shape to the skirt. By this time his curls had
started to loosen and although it was still relatively short it could be
styled more than usual with a nice fringe and the opportunity to tie pink
ribbon bows into each side.
He wore the same pearl choker necklace that he had worn when his mother
had first introduced him to Anne, and anew set of pearl earrings that
dangled nicely towards the collar. He was in pink 4" heels with ankle
straps and little lace anklets. His stockings were very sheer and natural
in colour. His eyes were dark, with a heavy application of eyeliner and
mascara and a charcoal eye shadow contrasting dramatically with the pink
and creams of his dress. His lip gloss was a gentle pink that brought out
his ever improving complexion. As he walked the little round bells that
Mistress Anne had made him sew on to the hems of one of the layers of his
pettis tinkled and announced his presence, as did the air with his perfume
that had been sprayed in all of the usual strategic places. It was not all
that often that he was allowed to dress in such a sophisticated way, well
sophisticated for a sissy, and he loved it. He was free from the belt and
Mistress Anne had left out his plug and every movement of the lace and
satin against his body sent a thrill through him.
As he walked across the entrance hall to position himself by the door and
wait for the Mistresses to arrive, Mistress Anne watched him with delight.
He really was quite pretty, and his movement and mannerisms were also
improving all the time. But he did still have trouble tying those ribbons
behind his back.
"Stand still for a moment Prue while I retie the ribbon around your waist.
Will you never get this right girl?" He started to mutter an apology but
he saw that she was smiling at him not angry with him. She walked to his
side and putting a hand on each waist she turned him to face away from
her, before taking the ribbon and tying a nice tight bow in the middle of
his back, with the ends of the ribbon trailing to just below the hem of
the skirt.
"Much better. Turn around and face me and look at me."
"You look really pretty today Prue, and I am very proud of you for trying
so hard since we first met. I know some of what we have asked you to do
has been difficult for you, but even though you have been punished from
time to time, every Mistress thinks you are doing so very well. Perhaps
tomorrow when things settle down we could go for one of our walks in the
garden - it is sometime since I have had you in the harness and collar.
Oh. I nearly forgot. Where are the posies of flowers that you have made
from your garden for Mistress Alison and Mistress Bridget?"
"I have them in a vase near the door Mistress, but thank you for reminding
me. I hadn't thought of them for a while given the time it has taken to
prepare."
When the door bell rang, Prue was there immediately to open it but of
course he backed away after opening the door and kept his eyes downcast at
the feet of the two Mistresses.
Mistress Alison was first to speak. "Thank you Prue. You may look up now.
This is Mistress Bridget and you have permission to say hello."
"Thank you Mistress Alison. Hello and welcome Mistress Bridget" said Prue
as he curtsied and then gave a posy of flowers to each Mistress.
Mistress Bridget was tall, much taller than Prue. He guessed that she was
at least 6' and maybe a little more, and she was also a very striking
young woman. He shivered at the thought of being punished by her at some
time, or being led around in his harness. Of all his Mistresses, she was
the most imposing at least in a physical sense. He wondered immediately if
her coming to live here would be such a good thing for him. She must have
sensed his concerns, as she took his pretty face in her hands, pulled him
close to her and then leant over to whisper in his ear. "Don't worry Prue.
If you are a good sissy I will be kind, but heaven help you if you ever
misbehave in my presence."
"Get me your collar and lead."
He took it off the hanger near the door and soon Mistress Bridget had him
locked in the steel collar under his choker necklace and taking the chain
in her hands she lead him into the living area where the other Mistresses
were waiting to greet them.
"Welcome Bridget. It seems that you have already met our sissy. I think
that you will find him to be a delight at most times. Of course, when he
is not we have ways of making him aware of his misbehaviour."
"Thanks Jennifer. It is wonderful to be here", she said as she put a hand
under his pettis and rubbed it against his delightfully ruffled panties.
?I think it is going to be a lot of fun living here."
End of Part 3
(to be continued)
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