Sissy Prudence Part 1
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Sissy Prudence Part 2 free porn video
Sissy Prudence (Part 2)
(by Sissy Caroline 22 December 2006)
Section 1
"Prudence. Come here at once."
Dressed in his maid's uniform, Prudence walked obediently into the room
and then knelt down before his mother, his eyes lowered to her feet. He
knew he was in trouble because she had called him Prudence.
"I have just been talking to Mrs. Smithton, who tells me that she is
increasingly concerned about the quality of your work when you are
supposed to be performing maid duties for her. Dishes not cleaned
properly, dust left on the window sills and the list goes on. What have
you got to say for yourself before I decide how you will be punished? I
am actually glad Mrs. Smithton raised the issue with me - there is some
evidence that you are not doing everything here as well as I want as we
have already discussed."
The boy didn't know what to say. It was true that lately he had not been
as diligent as he should have been. Why? He didn't really know - it was
just that he sometimes felt a sense of guilt about what was happening to
him, largely because of the initial choices he himself had made. He knew
he was a sissy and he desperately wanted to do all the right things, but
sometimes it was hard to be as good as others wanted him to be.
"Mother I am sorry. What Mrs. Smithton says is true. I have not been a
good maid for her recently. I just seem to be a little distracted or
something."
His mother was not surprised by the answer. In a very confidential way
she had talked to a counselor about her son, and it had helped her to
understand the fluctuation in feelings that Prue would have,
particularly in his early teens. After all he turned 14 years of age
only two weeks earlier. Perhaps that in itself had made him reflect on
what he was committing himself too.
"Come over here Prudence and sit at my feet."
The boy moved closer to his mother still without looking directly at
her. She took his face in her hands and made him look directly into her
eyes while she spoke quietly to him.
"Prue my darling, I do understand how difficult things may be for you at
some times. It can be hard for a young boy to let himself go and be the
sissy he really wants to be, always worried about what others will think
if they find out, worrying if there is something wrong with them. In
your case, however, we have already seen what you want to be. I know,
Mrs. Smithton knows as does Miss Hampson. You are accepted by all of us
and in the last few months you have begun to blossom. You have picked
some lovely new sissy dresses for yourself, your makeup skills are
getting better all the time, your deportment is improving and, most
importantly of all those things, you have generally become more docile
and willing to recognise that females of all ages are superior to you.
Isn't that all true?"
"I suppose so mother."
"Well, I say it is. I am pleased with your progress, but I am not going
to allow you to regress into old habits. From now on I intend to be much
more demanding of you in every way, and I expect Mrs. Smithton and Miss
Hampson will be as well. We must also think about getting you out and
about as a sissy. You cannot spend the rest of your life inside. What do
you think I should do to punish you darling?"
The boy blushed. He hated this question. Somehow he was always asked
what his punishment should be and he never knew what he was expected to
say.
"I suppose I should be spanked mother."
"Is that all darling? You think a few straps on your bare bottom are
enough to make up for your misbehaviour?"
"Yes mother." He was damned whatever he said he supposed, so he held to
his original position.
"Hmmm. Well. I agree that you should be spanked and so each of the three
of us will give you the strap 50 times on your sissy bottom. I will
strap you tonight before putting you to bed, and Mrs. Smithton and Miss
Hampson will do the same when you are next with them. In addition you
will wear your chastity belt continuously for the next month. How you
cope with that is your business. From now on, you will be made to
understand that you are under my control during every minute of every
day, even if you are not dressed as a sissy at the time. When was it
that I last allowed you to play with yourself?"
Of course she knew the answer, but she wanted him to acknowledge this
very powerful aspect of her control over him.
"It was on my birthday mother."
"Of course it was. How could I forget, with Mrs. Smithton and Miss
Hampson both enjoying watching you behave like a true sissy and playing
with yourself after I had put you in nappies and plastic panties, and
while Mrs. Smithton held the leash to your harness."
"Get the belt now."
Inside half an hour his mother had him secured inside the belt that
would not be unlocked for 30 days. This would be the longest period ever
for him, but she was sure he would cope with the physical demands, and
perhaps it would help improve his focus on who and what he was.
Before he went to bed she dressed in her leather outfit while he was
told to wait for her in his bedroom. When she came into the room, he
knelt at her feet and kissed her boots before pulling down his panties
when he was told to do so. Still kneeling at his mother's feet she used
her leather strap on him the 50 times she had decided would be part of
his punishment. He took it without a word, and then she dressed him for
bed and left him to dream of what had happened to him and where things
might lead.
Section 2
"I have just strapped him and put him to bed Anne. Please do the same
before you put him to bed tomorrow night and for heaven's sake if his
work is not up to scratch this time let me know, and we will talk about
how we get through to him. I told you I have locked him into the belt
for a month haven't I?"
"Yes Jennifer. He has been so good up until recently, but I guess we
were always going to have to get a little tougher with him. Did you
think any more about Janice's suggestion about an addition when he is
wearing the belt?"
"Yes. When we are up there in a week's time I will have a final
discussion with her about it, but right now I think it may well help us
improve his behaviour. How did you go finding him a new maid's outfit
for those special occasions when we are all together?"
"I have it on order, and I should be able to take it up with us next
week as a surprise for him."
"That's great. He loves his frillies you know."
Section 3
"Come on darling. No one will see you once you are in the car."
Mrs. Smithton led Prue, who was in her collar and harness, out to the
car and placed him in the back seat. He had to sit on a plastic lined
rug even though he was in his nappies and plastic panties under a short
cotton dress that he sometimes wore outside if he was doing odd jobs in
the garden. His mother certainly didn't want him to wet the car seat on
the journey of over two hours, and the rug was insurance because he
couldn't easily go to the toilet dressed this way and in his belt.
Despite the simplicity of his outfit, he still looked quite pretty. His
nails were light pink as was his lipstick, and a simple ribbon set off
his lengthening hair very nicely. He looked quite a bit younger dressed
this way than his real age of 14.
Neither his mother nor Anne spoke to him on the long drive to Miss
Hampson's place. He was given a bottle of drink but he was not keen to
drink anything because he knew he would wet himself during the trip. It
had happened to him before. It wasn't so much the wetting of himself
that worried him, it was that he was required to ask permission to pee
in his nappies before he did so. If he was wet when he was changed and
he had not asked permission he knew from experience that the punishment
would be severe. Despite himself he finally knew he had to ask.
"Mother. May I have permission to wet my nappies please?"
"Do you really need to wet them darling?"
"Yes mother I do. Please let me wet myself."
"What do you think Anne? Sometimes I think he doesn't try hard enough to
control himself. It is like his wish to play with himself all the time,
although we have that very well under control at the moment."
Anne looked around at the boy sitting rather uncomfortably on the
plastic lined rug. She smiled at him before agreeing that he looked like
permission was needed.
"Very well then Prue. You have my permission to wet your nappies. I hope
that is all you need to do. The last thing I need when we get to Miss
Hampson's place is a sissy who has messed herself."
The rest of the trip was a misery for Prue. Not only was he wet and
soggy, but he was totally embarrassed. And what if for some reason he
had to get out of the car? It was not worth thinking about - his life
was difficult enough at times as it was.
On arrival at Miss Hampson's he was led inside by Mrs. Smithton before
Miss Hampson took him away to be punished and changed into his clothes
for the rest of the day.
After changing out of his travelling clothes and bathing, and then
carefully using a hair dryer to make sure he was dry inside the belt,
Miss Hampson took him into a room in the house he had not been in
before. He knew immediately that it had been set up as some sort of
punishment room, with an array of leather devices, a leather bench,
anchor points in the ceiling floor and walls and a sort of padded narrow
bench over which Miss Hampson now stretched him, locking his hands and
legs to the bottom of each of the legs of the bench. It was
uncomfortable with his belt locked in place as it was, but she made sure
that he understood that his comfort was of no concern to her.
"Now Prudence. Your mother tells me that you have been a very naughty
sissy, and that you are due 50 strokes of the strap from me. That is
correct isn't it?"
"Yes Miss Hampson."
She stepped around in front of him and moved her leather boots close to
his face, and in almost a reflex action she watched with pleasure as the
boy moved to kiss them - despite his faults recently, he was still
improving and learning what was required of him. She held his head and
pushed him into the boots firmly so he could smell the intoxicating
aroma of the leather mixed with her distinctive perfume. He groaned
quietly and she knew that his penis was swollen but cruelly restricted
inside the belt that she had fitted to him for the first time all those
months ago.
"You like kissing my boots, don't you Prue."
"Yes Miss Hampson."
With that she used her strap on him, noticing that his girly bottom was
already red in places from the spankings given to him by his mother and
Anne. He squirmed as the strap hit him, but she held him tight with one
hand against her boots and she could sense him kissing them with some
passion as the strap continued to remind him that he was a sissy who
must obey his mother, Mrs. Smithton and herself at all times.
When Miss Hampson finished the punishment he became aware that his
mother and Mrs. Smithton were also in the room, and that they too were
dressed in their all leather outfits. He could see the boots on his
mother that he so loved to kiss and those strappy stilettos that Mrs.
Smithton allowed him to kiss when she kept him collared and harnessed at
the end of a day of maid duty. How long had they been there? Did they
witness his humiliation?
A few minutes later they all left the room and he was alone with his
thoughts and a very sore bottom for some time.
It was Miss Hampson who came back in to see how he was. She left him
strapped down, but told him that after release he would be dressed as a
maid for the day and that he would be expected to perform his maid
duties impeccably or else he would be punished again. As she spoke to
him she walked behind him and touched the band on his belt that ran
between his legs, running her finger around the edges of the hole in the
band that allowed him to go to the toilet. She put on rubber gloves and
with no word as to what she was doing he became aware that she had put
some lubricant on a finger and was pushing that finger gently inside
him. He didn't know what to feel, but he knew better than to say
anything without permission.
"We have all agreed that this is necessary to continue your training as
a sissy Prue. I must admit that your mother took some convincing, but I
was able to get her to talk to the owner of another sissy about your age
who confirmed that it had made a big difference to the way her sissy saw
herself."
"So from now on there will be considerable periods of time when you will
be required to wear a plug, even though it would be really nice if you
would ask me to put it inside you. I want you to ask me to put a plug in
you Prue. Do that now for me."
He knew all about these things from his searches on the net and, as with
many things that had happened to him he felt excited on the one hand and
concerned on the other about being treated this way. However, he knew it
would happen whether or not he asked, and that if he didn't ask he would
be punished again.
"Please Miss Hampson, would you put a plug in me."
"Why of course I will darling," and he felt her slide the plug inside
him and his sissy bottom close around it before she screwed a plate over
the hole in the band of his belt to ensure there was no way he could
remove it by himself.
The feeling was uncomfortable at first and when he was released and
stood up he felt it move even deeper inside him, and he noticed Miss
Hampson watching him carefully for any reaction.
"Good girl. Now let's get you dressed for the day. Anne, Mrs. Smithton,
has a new maid outfit for you and she would like to help you put it on.
"Anne. He's ready."
A short time later Prue found himself in the maid's outfit he had always
dreamed of and wanted from the outset. He was corseted and laced in
tightly first before Anne put on a lovely black and white lace bra,
black panties with white lace trim and a suspender belt holding up a
pair of fishnet stockings. His shoes were black 3" heels with ankle
straps, and the she slipped on multi-layered white lace petticoat before
the French Maid dress was zipped and then locked into place at the
collar.
"Turn around sweetie. Mmmm. You look very nice. How does it feel.?
"It feels really nice thank you Mrs. Smithton. Thank you so much for
buying this for me."
He truly loved it, and for a while he forgot about his sore bottom, his
chastity belt and his plug.
His mother came and put a collar and lead on him before taking him into
his bedroom to sit him down at his makeup table. With gentle hands and
quiet conversation to assure herself that her precious boy was adjusting
to the significant change in his life, she made him up to look as
beautiful as ever. Her final touch was to pin a tiny black and white
lace bonnet onto the top of his head.
"Real French Maids always wear a little bonnet or cap don't they
darling."
"Yes mother."
Jennifer was delighted with what had happened. He looked his usual
gorgeous self and he seemed to have accepted the spankings and the plug
as part of his ever changing life. She wondered what he thought about
the ?dungeon', but she guessed that over the time of their stay here he
would adjust to the fact that it was to be his place of discipline.
The three women relaxed while their new French Maid busied himself doing
all the tasks that had been assigned to him, before he was allowed to
relax at their feet after dinner and listen to them talk, and
occasionally being asked to make a comment about some matter concerned
with fashion or life as a woman. He was very comfortable, and to be with
these women, all of whom were dressed in leather, was a genuine reward
for all the hard work he had done for them as a maid.
"Kiss my feet Prue."
It was his mother speaking and of course he knelt before her before
doing exactly as he was told. In turn he did the same for the other two
women, and he had to admit to himself that he loved every minute of it.
If only he could play with himself, but he knew that would not happen
for some time yet.
After he was put to bed by his mother, he heard Miss Hampson tell his
mother that "Alison should be here about 10.00am." Who was Alison?
Section 4
He slept soundly despite all that had happened to him during the day.
The plug remained in all night and after he had gone to the toilet and
bathed it was reinserted, this time by his mother. He was then told to
dress in one of his very little girl outfits, with lots of ribbons and
bows, make himself up and be downstairs again by 9.30am. When he came
downstairs he was surprised to see all three women dressed in leather
again. That was unusual he thought, but he worried no further as he
stood still in front of his mother for his first inspection of the day.
She was pleased with the way he had dressed and done his makeup, but she
noted he could do with a manicure some time soon.
"No maid duties today Prue, but Mrs. Smithton would like to take you for
a walk in the garden. Get your harness and collar for her please."
He spent the next hour in the garden with Mrs. Smithton who was
wonderful to be with as usual. They walked slowly and a lot of the time
she held his hand while still holding his leash. She knew he liked to do
this with her and it gave her a sense of satisfaction she had not known
before. He was gorgeous, docile, submissive and loving and under her
control. What a feeling of power it gave her, but she knew it was power
that had to be used wisely.
While they were outside Alison arrived. "Hi mum," she said to Janice,
giving her a big hug. "My you look as good as usual in your leather. No
wonder I am wired the same way as you, and no wonder my father left
early when you tried to boss him around. He was a real wimp wasn't he?"
"Oh yes he was dear. I couldn't bear the thought of keeping the name of
a wimp like that. So how is Bridget? Is it two years now?"
"She's really well, and very interested in what you ladies are doing. If
things work out then she may want to participate, but I told her to let
me see what he is like before we go any further."
Alison was a beautiful blonde with a great figure who, much to her
mother's delight, liked the company of women rather than men. To Alison,
men were inferior beings, and only dressing them as girls made them in
any way acceptable. Her partner, Bridget, was a cutie as well, and she
too had similar feelings about men.
Alison sat for a while and talked to Jennifer and Janice about Prue and
the stage he was at in his sissification. She observed him through the
window for a while as he was led around the garden by Alice.
"Well he is a cute little thing I have to admit. Younger than the last
sissy I managed for a while, but that is a good thing as we know.
Shaping them early is the key. My last sissy eventually got affected by
some bad influences because his mother was not careful enough with who
he was seeing and when - he left home and she hasn't heard from him
since. Goodness knows what he is up too, but the key is to have very
strict control of community in which the sissy is allowed to operate. In
fact, the fewer males that they interact with the better."
"So you really think all of us moving here will create that
environment."
"Yes Jennifer, I do. That way he can be influenced every second of every
day, and if you play your cards right we can get him out of school and
keep him out of school during the shift of residence. In his present
environment you run the risk of him meeting a girl he likes who he would
prefer to be with than continue his sissy role or, worse still, other
boys will see what is happening to a degree and shame him into rejecting
a sissy role - at least for a while. Get him here, I will move in with
Bridget as well, I am almost certain she will come, and then help you to
take charge of his day to day running so that you are not worried by all
the details of his training although it is you who must finally
determine the agenda. He is after all, your son."
Jennifer looked at Janice. "Okay. We will do it. It will take me at
least a month to sort things out. Would it be better if he stayed here
rather than come home at all?"
"Well. You are more than welcome to do that. If Alison came to move in
very soon, I am sure we can keep things going while you and Alice make
arrangements to shift."
Things went much as Janice had hoped. She knew this was the right course
of action, but it was a big decision for Jennifer and Alice to make, and
she knew Jennifer would be quite concerned about her son's welfare. But
in the end, the right decision had been made. Prue would now have almost
no chance of escaping from the sissy training that was most desirable.
A short time later Anne led the boy inside and he almost jumped when he
saw a new and very beautiful young lady in the room. He stood there for
a while saying nothing, until his mother spoke to him very sharply.
"You should know better Prudence. Greet Mistress Alison properly at
once."
Prue took a step forward and curtseyed and said "I am so pleased to meet
you Mistress Alison. My name is Prue and I am a sissy."
Alison stepped towards him and pointed at her feet. Immediately he knelt
in front of her and kissed the toe of each shoe gently. Alison smiled.
Even at the tender age of 14 he was doing quite well. She was going to
enjoy her time with this sissy.
Section 5
Mistress Alison had Prue strapped into the chair in which he would have
his hair styled. A week after his mother had returned home the sissy was
still proving to be more difficult than she had thought he would be. He
was bewildered by the fact that he had been left behind and, although
his mother said that she would be back in a few weeks he remained
anxious. And Mistress Alison was incredibly strict with him, keeping him
chained or tethered in some way all the time because of her concern he
might take off. At night he was collared and chained in his cot, and
during the day his legs were shackled to restrict his movement even more
than usual.
Prue's hair had not been cut for some time, and although it was still
relatively short and suitable as a young boy's style, it could now be
fashioned more than had been done before. Jennifer had agreed with
Alison on a new style that would make it very hard for him to decide he
should be seen outside in male clothing.
She washed his hair and then put a slight blond rinse through it, the
effect of which was quite remarkable. His complexion seemed to change
and the overall effect was to soften his features even without makeup
on. Without telling him anything about what she intended, Alison then
started to give him a new perm, but unlike the last time when he was
left with wavy hair, this time he would end up with quite tight curls.
She worked on fitting a number of small hair rollers, winding his hair
tightly into place until he could feel the rollers pulling on him. The
setting lotion needed a long gentle drying period and he sat under the
bonnet for nearly an hour while Alison gave him a manicure and a gentle
face massage with a wonderful smelling cream.
"You like me massaging your face don't you Prue. I can feel you relaxing
under the pressure of my fingers."
"Yes Mistress Alison." It was true. He had been so out of sorts for a
week or so, that this period in the chair was the most relaxing he had
experienced in that time.
Alison smiled. This was good. He needed to relax, and he needed to trust
her if she was to make the further changes that were necessary. "What
about we pluck your eyebrows while we are here darling? They could do
with a bit more shape. Would you like me to do that for you as well?"
"Yes please Mistress Alison."
Although she knew he had to say ?yes' she was pleased with the way that
he said it so quietly and in such a genuine manner. This one had real
potential.
When the drying hood came off and she took out his rollers she was very
pleased with the result. Sweet tight curls all over his cute blond head
and when he saw himself in the mirror he was shocked. He now looked even
younger than before and more like a little girl than ever, and being
seen in male clothes would be a disaster for him. He felt so trapped
that his composure broke for a moment and he burst into tears, pushing
against the restraints to try and free himself even though he knew that
was futile.
Alison knew this would be a critical time and had arranged for Jennifer
to be available on the phone. "It is Mistress Jennifer on the phone for
you Prudence. Listen to what she has to say very carefully."
"I decided on your new hairstyle Prudence. Mistress Alison is simply
doing what I asked her to do, and you should know by now that you do
whatever any of the Mistresses asks of you and do it willingly. If you
continue to be naughty I will strap you severely when I get there in the
next few weeks. What have you to say for yourself?"
"I am sorry mother. I will try and do better, it is just my new
hairstyle was such a shock. It makes me look about 9 years old."
"Believe me dear that was the intention. So obey Mistress Alison and
Mistress Janice and be a good sissy. By the way, from now on you will
refer to me as Mistress Jennifer. Is that clear?"
Alison took the phone from him and stroked his face. "I am going to
punish you for your disobedience Prudence, but before I do that I must
do your ears and makeup." Soon he had a piercing in each ear, and was
beautifully made up. Released from the chair Mistress Alison led him
straight to the discipline room, spread him over the spanking bench and
strapped him very hard 50 times. This was the third time in the week he
had been strapped by Mistress Alison. Once was for not having painted
his toenails properly and the second was for not tying the bow in his
hair the correct way. Now this. He wondered what else he could do wrong.
Released from the bench she then led him out into the garden and made
him sit at her feet while she spoke to him about his misbehaviour and
the ways in which he could improve. After a while he settled down and
she drew his head close to her legs and allowed him to nestle his
tightly curled head against them. She allowed him to remain that way
until it was nearly dark.
That night as she put him in his nappies and plastic panties after
ensuring his belt and plug were secure, she again spoke to him quietly
about what she required of him, while all the time stroking his face and
kissing him on the cheek. He became very aroused but of course for this
sissy there was absolutely no possibility of release for some time.
"Perhaps when Mistress Jennifer releases you from the belt you could
play with yourself for me darling. Wouldn't that be nice? Perhaps I
could put you into your plastic harem girl outfit and you could become
excited for me."
(end of Part 2 - To be continued)
Alma
- 02.07.2021
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