Sissy Prudence Part 2
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Sissy Prudence Part 4 free porn video
Sissy Prudence (Part 4)
(by Sissy Caroline)
Section 1
"Control, discipline and dependence are all very closely linked Jennifer.
Ultimately we want him to be totally dependent on us and we use
discipline and other means of control to help us achieve that state of
dependence. Although you should be very pleased with progress, he is a
long way yet from where he could be as we have discussed previously."
"I know that you're right Janice. I love the way he has responded so far
but I can see that we need to do more. He hasn't really been out and
about as a sissy yet, for example. Still, there is no rush is there. By
the way have you noticed how he looks at both Alison and Bridget? He is
absolutely besotted with both of them, even if he would not admit it." At
that moment Mistress Alice came into the room with Prue in his harness
and on a leash. They had been walking in the garden and Prue walked
slowly a short distance behind his Mistress as he had been taught to do
unless given specific permission to do otherwise. He was in his
gardening clothes and he still had on his broad hat with the ribbon tied
underneath his chin and, to the surprise of both Mistress Jennifer and
Mistress Janice they could see that he had been crying.
"Let me put our sissy away safely for the time being," said Mistress
Alice, and then I will tell you both what this is all about. Come with
me now darling. Let Mistress get you settled down for the afternoon."
Alice lead him into his discipline room where she made him undress then
put him in his chastity belt and butt plug before a nappy, plastic
panties and a cute pink baby dress completed his outfit. "In you go
darling. It has been a stressful morning for you so you can rest until
it is dinner time." She opened the door to his small cage and watched
him with a smile as he crawled inside and then curled up on the thick
rug. The cage was too small for him to stretch out and not even high
enough for him to sit up in, and he had resisted being placed in it when
it was first put in his discipline room some two weeks earlier. Now,
however, he was starting to accept that being caged was a part of his
life, and he didn't protest at all when Mistress Alice slipped the
locking bolt into place and clipped the padlock shut.
"Relax Prue. You have my permission to wet your nappies if you are
unable to hold on." She left the room closing the door behind her and
leaving the key on a hook near the door.
Back in the lounge room she told Jennifer and Janice that Prue had been
upset when she asked him about how he was behaving for Mistress Alison
and Mistress Bridget. "It seems that he cannot do anything right for
either of them and he is being strapped quite regularly as we all know.
But it is not the strapping that is upsetting him - he thinks that he is
letting us all down but particularly you Jennifer. Isn't that
intriguing?"
"Our little boy is really coming along better than we thought then," said
Janice.
Section 2
"Oh my. What a pretty daughter you have Jennifer. I just love all those
frills and bows and the shoes - she does look so lovely in pink doesn't
she? How old is she? I must say that she looks no more than about nine
years old, although she is quite tall for that age."
Jennifer laughed at the deception. "Goodness me Julia. This is my son
and his name is Peter. He just loves being dressed as a girl and
especially in lovely frilly sissy outfits. Don't you darling? Show
Julia your frilly panties darling and also let her see that you have on a
chastity belt and a plug is inserted. That's it sweetie. Show yourself
off."
Prue awoke with a shiver. He had had this dream before and it worried
him. Perhaps it meant that he really did want to go out dressed as a
sissy and be exposed to others. He squirmed as he realised his nappy was
soaked and his nightie was all bunched up around his waist. His legs,
which were now shackled every night, were tired from the new shoes he had
worn all day previously on his maid duties, and his plug was so
intrusive, as it usually was for some reason when he woke up.
It was Saturday morning and he knew he had no time to waste. He had to
dress as a French Maid and then cook and take breakfast to each Mistress
while they were still in bed. Saturday was often one of his busiest days
which is why, most times, he was allowed to rest for a large portion of
Sunday.
Section 3
"I won't go."
It was said so softly that Mistress Jennifer could barely hear him even
though he was sitting at her feet.
"What did you say?" There was a level of menace in her voice he had not
heard before, and it frightened him. But he was determined. He had
thought about this a lot and he was not going to any girly function or to
any beautician. He simply would not go and no one could make him.
"Say that again."
?I won't go."
She slapped him hard on the cheeks and said nothing, and then there was a
long silence before she slapped him again. Then another long silence
before another slap and then an indication he was to bend over. She
lifted his dress and petticoats and pulled down his frilly panties
exposing his plugged bottom and the straps of the chastity belt he had
been in for a week now. She took the leather strap off her belt and began
to strap him with it. His bottom was already red from a previous
discipline session and he squirmed as she continued to strap him until he
began to sob quietly. At this she stopped, pulled up his panties and
motioned for him to kneel back at her feet.
She looked at him waiting for a positive response, but he just looked
away.
Without a word, Mistress Jennifer picked up the lead on his collar and
led him to the discipline room where she locked him in the cage and left
him alone for three hours.
Eventually he heard the heels of her leather boots on the polished wooden
floor of the hallway, the door open and her heels on the floor until she
was at the cage. He did not look up - he was in enough trouble already
he knew. She opened the cage and pulled him out on the leash and pushed
his head down so he knew he was to kiss her boots.
She lifted him by the chin so he was forced to look at her.
She said nothing and he wanted to relent but he couldn't make himself say
anything.
Tied over the discipline bench he was strapped again until he sobbed and
was put back in the cage. He was there for what must have been hours
without release and he had no nappies or plastic panties on. He knew he
would disgrace himself because he had no choice and he just wished he
could disappear from the face of the earth. Why was he doing this? He
liked being a sissy but he was terrified of others outside his immediate
circle discovering who he really was and the sort of life that he lived.
Eventually he fell asleep and it was morning before he woke - wet and
messy and tired and confused.
Mistress Jennifer released him in the morning to wash and put on clean
clothes before he was locked away again until the afternoon, when he was
led back into the lounge, being made to crawl behind her. For the first
time in a day Mistress Jennifer spoke to him. "Now what was it that you
wanted to tell me darling?"
Again silence and a slap to the cheek, but he knew he would have to yield
or go on like this until he did.
"I will go Mistress."
?Of course you will darling. It was just a matter of time before you
realised that you have no choice in such things. Your other Mistresses
and I decide how you live your life - not you. You are not capable of
doing that as we have seen. You need control and direction - all sissy
slaves do." Despite Her outward confidence, Jennifer was concerned at
his disobedience and perhaps stronger actions were required as Janice had
suggested.
Section 4
Prue's relationship with each Mistress was very different. With Mistress
Alice he was very obedient and submissive, but he also loved being with
her. She spoke to him gently most times and he found that he was very
close to her and being in his harness and on a leash in the garden was
wonderful. He loved his mother of course, despite the recent punishment
she had inflicted on him. It was his own fault and he knew he deserved
it for being so disobedient. With Mistress Alison and Mistress Bridget
he was always on edge because the truth is their highly sexual appearance
and behaviour made him both fearful of them and in awe of their
increasing power over him. With Mistress Janice he had almost no
relationship at all. She was strict with him and required absolute
obedience, as did all the Mistresses, but there was no real relationship.
He often wondered whether she just didn't like him, or if the experiences
with her former husband meant that she was wary of all males.
So, to find that he would be spending at least a week alone with Mistress
Janice worried him enormously. Mistress Alison and Mistress Bridget were
away on work business and Mistress Jennifer and Mistress Alice were to be
away for at least a week looking at the operation of some sort of
business some distance away.
"Now you behave for Mistress Janice darling. I am sure that you will
but, if you don't She has the authority to deal with you." With that he
was alone in the house with Mistress Janice.
Prue was in his long maid's dress and he was shackled now as well since
his disobedience of a few days ago. It was hard for him to get around
and do his housework but he managed by mid afternoon to do everything
that was required and, with everyone else but Mistress Janice out of the
house things should be easier for him for a few days.
"Get in here now Prudence."
He entered the lounge room, curtseyed and knelt down before her. He knew
something was wrong. What had he done? Then he saw the small towel near
the chair that he had failed to pick up.
?What is this?' Mistress Janice said pointing at the towel. "Put it
away and crawl to the discipline room you useless worthless boy - I just
knew you were useless and now you have shown how useless within moments
of your mother leaving. Get out of my sight until I have time to punish
you."
She strapped him again and again but then, to his surprise, she led him
back into the lounge to kneel at her feet, when he thought that he would
probably have been put in the cage.
"You don't like me do you Prue? Be very honest with me or you will be
punished again."
"No Mistress. It's not that I don't like you, it's just that I think you
don't like me very much that's all."
"Sit up near me Prue." He sat next to her but kept his eyes down and
said nothing.
"Head in my lap facing me. Quickly boy."
Mistress Janice ran her hand over his face and then, gently, placed a
finger on his pink lips and pushed it inside his mouth. She moved it
gently inside him and felt him begin to respond too her gentle intrusion.
She pushed her finger in and out and ran the tip of her nail around the
edge of his lips.
"Do you think I like you yet Prue?" she said, her finger continuing to
examine his mouth and lips. She could feel him move against her, and she
was sure that he was swelling inside the chastity belt that was now such
a big part of his life. She pulled up the skirt of his maid's dress, and
made him move so that she could get it right up around his cute little
bottom, before she pulled down his panties and began to spank him very
gently with an open hand.
"My little darling loves this doesn't he? Such a sissy." The spanking
continued and she could tell he was becoming more and more aroused, and
starting to shift to try and ease the pressure in the tube of his belt.
But of course it just increased as he started to relax even more and seek
to suck her finger deeply into him.
She bent over, pulled his head up and kissed him full on his pink sissy
lips before easing him down and reinserting her finger. He moved his head
closer to her belly and nuzzled into her before asking, in a soft husky
voice, if he might put his arms around her.
"Of course my darling boy! Of course you can."
He held her tightly and turned his head upwards slightly so that she
could still have her finger inside him. She looked down at him and, for
the first time since he had been living here, she smiled at him and he
felt at once relieved and safe and secure. He smiled back and hugged her
even more tightly.
"Perhaps we do need to get to know each other better Prue. Your mother
was right. So this week will be good for both of us."
For the rest of the day, Prue had a spring in his step. He prepared the
evening meal, served it to Mistress Janice in his French Maid outfit and
then sat at her feet while she watched some television and, just
occasionally, allowed her hand to wander near the sissy's mouth so he
could suck the tips of her fingers.
At bed time he changed and waited on his cot for her to put him in
nappies and the plastic panties that would clip on so that his shackles
did not have to be removed. He lay on his back quite still while she
powdered him and then slipped his nappies and panties into place. She
then took one of his steel collars from the wall and locked it on him
before attaching a leash and indicating to him that he should stand up.
He was surprised but said nothing as she led him into her room, told him
to get into her bed and then locked the lead to the ring near the head of
the bed. A short while later she had showered, and changed into a
transparent nightie that showed her ample breasts and the dark rings of
her nipples. Leaving a low light on in the room she got in beside him
and reached for him immediately, pulling him close to her and guiding his
head to the canyon between her breasts. She pulled down one side of her
nightie and putting a finger in his mouth she pulled him towards her,
whispering to him that she wanted him to suck her nipple.
He did as he was told and he soon found himself in state of such
excitement and pleasure that he would have released if only he was not in
chastity.
"Oh dear, my little sissy is frustrated isn't he. What a pity that you
are not allowed release for some time yet. Still, your job is to look
after your Mistresses isn't it, and not to worry about your own
pleasure?"
He didn't respond but continued to take her nipple deep inside his mouth,
working it gently until she too was aroused and wanted him to be very
close to her. She took one of his hands and placed it on her, by now,
very wet pussy, and she guided one of his fingers inside her. He was
well aware of what he was to do and he continued to do everything in his
power to make her excited and pleased with him.
It was hours before they stopped playing and then they slept together in
each others arms until the late hours of the next day. There was no rush
to get up, but when he awoke he found her looking at him with a loving
smile. She kissed him and immediately put him on her breast while she
asked him if he needed to do anything.
"Yes please Mistress. I need to do pee pees and poo poos." This was how
he was always required to describe his toilet needs - just like a little
sissy baby would.
"Well then darling. You may do both as we lie here together."
"But Mistress, I have never pooed in my nappies. Won't it be too messy?"
"Do it sissy. I will punish you later for questioning me like that. You
do exactly as I tell you - never question me again."
?I understand Mistress."
"Good boy. Let it go darling. Be the sissy baby you really are."
He messed in his nappies as she held him close and he sucked her nipple,
and after he was finished she made sure that he continued to give her
pleasure. It was two hours later before she released him and allowed him
to clean up and bring her a drink in his baby bottle and a snack in bed.
Section 5
His new pink platform heel shoes were very difficult to walk in. He
stumbled a little as he walked down the hall way towards Mistress Janice
who was watching him very closely.
"One foot in front of the other and small steps. How many times do I
have to tell you?" She walked up to him and strapped him on his bare
legs. "I will shorten the shackles if you cannot do as I say." He had
been at this for over an hour. Mistress Bridget had bought him these new
shoes and an outfit he was yet to see - he suspected that she was going
to take him out somewhere in it and he was anxious about the thought. He
was trying hard but he just had trouble for some reason and he was about
to burst into tears. Mistress Janice walked up to him and gave him a hug
before putting one of her fingers to his pink sissy lips and letting him
suck on it until he calmed down.
"Perhaps my darling needs his dummy to suck on and keep him calm. Do you
need your dummy Prue?"
He knew it wasn't really a question but a statement that he was about to
have his dummy put in his mouth. "Yes please Mistress." After she
placed his dummy in his mouth he did seem to settle and his performance
improved markedly.
"Come on darling, that's enough for now. Let's get you into clean
nappies and you can sit with me in front of the fire and relax."
A short time later he was changed and in a new pink baby dress and then
Mistress Janice put him in a baby harness that she had bought for him.
It was made of a sturdy clear plastic and it had gold buckles and it
included a collar which she buckled very firmly around his neck before
leading him into the lounge room. "I want you to crawl behind me Prue.
Little sissy babies cannot walk can they?"
In the lounge he lay on a thick rug with his head in her lap while she
gave him a drink from his bottle and gently massaged his head and bottom
through the nappies and plastic panties. She knew he was loving every
minute of the attention and she had to admit she liked him being with her
like this. A while later he was on her breast and swollen inside the tube
of his belt.
Section 6
"The Mistresses will all be home today, so you must dress nicely for them
and greet them properly when they arrive. Perhaps your lemon outfit
would be nice."
Prue dressed with the help of Mistress Janice. She laced him tightly
into his cream satin corset before she made him hold out his arms to
accept one of his many lacy bras. As she fastened it behind his back she
gave him a kiss on the neck. "Good boy. I am so glad our boy loves his
lacy bras. He looks so cute in them and his frilly clothes. Arms up for
your pettis dear."
Then the lemon dress which flared beautifully over the layers of
petticoat and which just reached to bottom of his panties, under which he
was still in chastity and heavily plugged. Knee length cream lace socks
and lemon pumps set everything off nicely especially after she rubbed a
fine coating of baby oil over his bare legs.
He did his makeup himself as she watched and then brushed his hair before
adding a lemon ribbon that fell to his shoulders.
"My, your hair does need a bit of work on it doesn't it. It needs a
style and a perm to get some waves back into it. Here, use this pin to
keep it back from your ear on this left side so we get a good look at the
earring."
When each Mistress came home Prue opened the door to greet them,
curtseyed before them and handed each one a rose from the garden.
Mistress Janice was proud of him - perhaps males were acceptable if they
were kept in dresses.
Section 7
"So you saw him then Jennifer."
"Yes Janice. Up close and personal you might say as, of course he has no
idea who Alice and I are. He is certainly being kept under the closest
supervision imaginable. How long has he been there now? Five years or
so?"
"Yes it would be about that. The irony of it all is that it is his own
money that is paying for the treatment he is receiving and because the
authorities think he has gone overseas, no one is looking for him, even
though he is no more than three hours drive from here, even if he has no
idea where he is."
"Well he will be there for a while yet I assume. She has him locked into
this massive steel collar that has been welded shut and it is attached to
a length of heavy chain about 10 feet long which, in turn, is attached to
a very heavy squat cylinder of iron. He has to put it on a little cart
she has provided him with so he can move around with some freedom at
times. He works on the farm in the garden and as a beast of burden -
often he is harnessed to a cart to transfer material about the farm. His
home is a concrete cell near the main house but set back into the forest
a bit. It has hot water for heating and he can shower etc in side so it
is reasonably comfortable. Of course the cell is locked whenever he is
inside and even if it wasn't his chances of getting away carrying the
weight are negligible. She beats him regularly and seems to enjoy doing
it."
"Good. The bastard deserves all he gets. Is he an entire still?"
"Good heavens no. He was gelded in the first month. Isn't that what you
wanted?" Apart from all that, I am sure that she can help us with Prue
from time to time. Her house is lovely and she has all the facilities
required. I have made a booking for three months time for her to have him
for a month."
Section 8
"It doesn't look like the belt is causing you any problems."
He was out of his dress and lying on his back on the change table in his
bedroom. His mother had taken off his belt and she was pleased to see
that there was no abrasion apparent. She was sure now she could leave it
on much longer if she wished.
Out of a drawer she took a pair of his special plastic bikini panties -
the ones with the pocket into which she could squirt some baby oil and
then insert his genitals before tying them inside quite tightly and tying
the panties into place around his waist.
"If you release before you have permission you know there will be serious
consequences dear."
"Yes Mistress. I know." His voice was husky with excitement as it had
been a few weeks now since he had been allowed release, but he was
worried he might release involuntarily as he was erect and throbbing
inside his lovely little plastic pouch. His plug was still firmly in
place which made it even harder for him to control himself.
She slid his frilly panties back up his legs, replaced the shackles and
put his dress back on before making him sit down and touch up his makeup
and do his hair again.
"Now sit here and look at yourself until someone comes to get you."
A short time later it was Mistress Bridget who came into his room. She
was all in leather and her shiny high heel boots mesmerized him as she
stood over him with a small whip in her right hand. She put the plastic
harness on him that Mistress Janice had used a day or so earlier and took
him out into the lounge where he was to find all his Mistresses relaxing
with a drink. His rug was in the middle of the floor and he was made to
sit down upon it, and to sit properly as he had been taught. Mistress
Bridget stood over him with her boots close to the edge of his dress, and
as she pointed at them with her whip, he knew he was to lick them.
With all of his Mistresses looking on he began to lick her boots and she
hit him gently on his pantied bottom with her whip.
"Does he deserve release Mistress Jennifer? Has he been a good sissy
Mistress Janice?"
The whip hit him hard on his bare leg. "Keep licking slave, and stop
worrying about what is being said about you." She pulled him upright
with the harness and slapped his face before pushing him back down to
lick again.
"I think we should allow him release Ladies. Do we all agree? Yes.
Good."
"Keep licking but pull down your panties and stroke yourself through
those plastic panties darling."
He did as he was told and before long he shuddered as the thrill of
ejaculation ran through him again and again.
"Keep licking darling. No one told you to stop."
She then led him to the feet of each Mistress to lick her boots before
returning him to his rug.
"Kneel with your back straight."
Mistress Bridget passed the leash to Mistress Jennifer who came over and
pushed his head down so he would lick her boots again.
"Play with yourself darling. Do it for me and every Mistress. Make us
proud of our little sissy boy who just loves to release when given
permission."
He came again and again, and after each Mistress came to him to give him
a kiss, Mistress Jennifer led him away to his room for the night. He
expected to be left out of the belt, but to his great disappointment she
fastened it back on him before tucking him into bed. "This is continuing
punishment for your disobedience and, believe me there is more to come."
End of Part 4
(to be continued)
Vera
- 27.11.2022
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