Making a Sissy Maid Chapters 1 4
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Making Of A Sissy Maid Chapter 5-6 free porn video
Making a Sissy Maid - Chapters 5-
Reminder - Chris loves his mother and secretly longs to wear her sexy
lingerie. Out of the blue his mother meets the very handsome and wealthy
man of her dreams and soon marries. This introduces Chris to his new and
somewhat dominant sister-in-law who recognises the sissy in Chris and
transforms him into a pink frilly maid.
Chapter 5 - Chrissie and Eve
For that whole weekend Eve, his new sister-in-law, had kept me dressed
in his pink maid's outfit. we never left the luxurious penthouse
apartment that Eve's father, Dirk, owned. I was made to wait on Eve hand
and foot. Quite literally at times. I loved every minute.
My mother, Paige, was due back with her new husband on Sunday evening.
On Sunday morning I woke in the guest bedroom - wearing the beautiful
wispy pink satin and lace baby doll that Eve had given me to sleep in.
She had said "You little sissy, you will wear something that befits a
girly girl when you are in bed. But first we must make sure you behave.
Now hold up the hem of the nightie a second while I sort you out..."
I had held up the hem of my baby-doll and Eve bent down with something
metal looking in her hand. She squeezed my little cock tight so it
shrank and roughly pulled and tugged the metal cylinder over his
cockette. I heard a 'click' as a tight band of steel fitted round my
balls and locked onto the cylinder. My penis was now rigidly constrained
inside a tight fitting metal tube, which itself was locked onto my
balls. This pulled my balled upwards and made them swell but pulled my
cock down ward and meant only my purple shiny cock head was showing.
Eve laughed. "Now you are a chastised little sissy. How perfect!"
I reached down to my cock and balls. Eve slapped my hand away. "No
Chrissie, the whole point of this evil device is to keep you from
playing with yourself. You will not get an erection wearing this - or if
you do it will hurt like hell. I may be allowed to stroke your tight
little ball sack to torment you - but I would not recommend you doing as
it is going to make your little sissy cockette so sore." She laughed
again, looking at my bemused and concerned face.
That was how I went to bed on Friday night and that was how I still was
on Sunday morning. I had spent the whole of Saturday locked into my
chastity device. I had been made to perform endless oral sex on Eve -
trying to satisfy her almost insatiable sexual appetite - while all the
time my cock strained against the metal prison. My cocked leaked endless
amounts of pre-cum, so much so my pretty panties were soon soaking. But
Eve would not let me cum and by Saturday evening my balls were swollen
almost blue.
It was no better Sunday morning. The chastity device held my morning
erection down cruelly and all my little cock could do is drip pre-cum
into my baby-doll's matching lace pink thong. I moaned out load. I was
beginning to think this metal tube would do me some permanent damage.
But I also knew that if I did not get up right now Eve would be furious
and spank my already tender bottom. I remembered Saturday morning's
spanking only too well. I was luxuriating in the satin sheets of the
guest bed when Eve strode into the room.
"You lazy little slut. What are you doing? Where is my morning tea? I
have a lemon tea first thing in the morning, in my bed. I do not expect
to make it myself. I have a little sissy maid for that. Except maybe I
don't have a maid - there is no tea by my bed so clearly there is no
maid in the apartment. Well?" Eve demanded.
"Yes miss, sorry miss," I stammered, "yes, I'll get your tea miss,
please, I do want to be your maid."
"Oh you will get my tea, I know that," replied Eve, "but first I need to
make sure you do not forget this mistake. And you know that means a
little punishment, don't you?"
I remembered the hard paddling that Eve had given him the night before
and shuddered. Eve had found fault with me again and dragged me into her
bedroom. But just stood me at the base of her bed. There I had
hesitated. I did not expect this. I expected, almost wanted, to be
roughly forced into the kneeing position at the foot of Eve's bed. I
remembered with a thrill the feeling of being tied into that bent over
position. This was different. This meant me giving myself up to her hard
paddle on my own.
Eve had pointed at the ottoman at the base of her bed. And I had slumped
down in resignation. I bent over the ottoman, resting my head on the
silk quilt of her bed. I reached behind his bottom and pulled up the
short skirt of the baby-doll and rested the fold on the small of my
back. I then lifted my hands above my head.
And I had had to wait in silence for a long, long minute.
And then "whack!!!" - even louder and harder than last night. i howled
and clutched my smarting bottom cheeks. Eve just pushed me back into the
bed and batted away my hands.
"Count them."
Then "whack" "whack" "whack" in quick succession. I wept audibly into
the quilt and managed a gasping "two, three, four, ow ow ow."
Eve had smacked my already red and sore left cheek with a particularly
hard swipe, and then my right cheek with another. "Five, sob, six."
Then, very rapidly, so quick it had just became a blur of pain to me,
six more smacks - three on each cheek. I wept and howled and tears ran
down his face. "No more, no, please."
"Count." Eve's voice was cold and neutral.
"Seven, sniff, eight, sniff, nine, ten, sniff, eleven, twelve. Please,
miss, please, no more."
I remembered this from last night as I stood in her bedroom, almost
about to kneel over her ottoman. But seemingly Eve had either forgotten
or had other ideas.
"Tea" was all Eve said as she got back into her bed.
I quickly stepped out of here towards the kitchen, not sure if I
regretted missing the spanking. I thought that if I put the kettle on
now then nipped back to my room and changed into my maid's outfit, then
made tea then I would be quicker. A silly mistake.
When I walked back out of the kitchen there was Eve, stood at her
bedroom door. She stared at me in cold fury but she spoke quietly.
"Chrissie sissy, do you remember what I said about your pretty baby-doll
nightie?"
"Yes, miss, it is only for my bedroom."
"And Chrissie my very silly little sissy, where are you now?"
"Please miss, it was only to put the kettle on. I was going to change
right then and be in my dress when I made the tea." I stammered, knowing
where this was leading.
"Chrissie, I asked, where are you now?"
"Kitchen."
"I beg your pardon?" There was now a hard edge to Eve's voice, one that
held menace.
"I'm in the kitchen, miss, in my baby-doll, miss, sorry, miss."
"Sorry does not begin to describe how you will be. Now, I'm off to back
to my bed. I expect you, in your pink maid's dress, nothing missing,
with my tea, in 5 minutes." Eve stepped back into her room and I dashed
back out to my room and threw off the baby-doll. I struggled to get my
pink satin corset on very tight, but with no time just gave the straps a
few hard tugs Then I quickly up my stocking and fastened just one
suspender on each leg. I pulled on my lacy pink padded bra that gave me
a 38DD chest - this was another of Eve surprises yesterday. And then
pulled my petticoats on. And finally my dress down over my head. I
tugged up the zip as best I could, and, wait, no, also my shoes. I
struggled into the 6 inch pink patent stilettos and stumbled back to the
kitchen.
I quickly made the cup of tea with the now boiled water, sliced and
dropped in a bit of lemon and tried to look more composed as I carefully
carried to hot tea to Eve's boudoir. There, Eve lay on the bed over the
rich crimson satin covers. She was reading glamorous magazine. She
glanced up as I carefully placed the cup of tea on her bedside table
with the little curtsey that I has been taught.
"Wait there." That was all Eve said as she continued to read the
magazine, lazily flipping over page after page of photos of beautiful
models in expensive evening dresses. This went on for easily five
minutes before Eve took her first sip of tea. Then another five minutes
as she slowly sipped the tea and continued to read the magazine.
All this while I tried to stay as still and as straight as possible. But
it was increasingly difficult. As I stood there he became aware of how
shoddily dressed I was. I had forgotten to put on my make up. My lacy
little maid's hat was still on my bed. I just knew my stocking seams
were squint and with only one suspender holding them on each leg, the
easiest to fasten front one, they were slipping down at the back. My
uneven short petticoat would not be hiding the slipping stockings. I had
also forgotten to put on the little lacy fingerless gloves. And my
pretty satin and lace apron with the big sissy bow at the back. I
desperately needed to get back to my room to sort myself out.
"Please miss, may I....?"
Eve looked up. She placed the tea cup back on its saucer. She carefully
closed the magazine and placed onto the bed. She sat up and swung her
legs off the bed and stood right in front of me. Her breathing was firm.
"Do not speak, slut. You first disobey me by walking round the apartment
like a tart. Then you turn up dressed like you do not care. I am
disappointed in you, so very disappointed."
"Please miss, if I could....?"
"No" Eve cut him off, "you clearly cannot. Or maybe you do not want to.
What do I do Chrissie? I am beginning to think that you have tired of
this. I think you want to leave and never have the pleasure of being my
maid again. Is that what it is?"
"No, please, no, I'm just not yet..."
So you do want to be my maid? You just are not yet trained? Is that it?"
"Yes. Miss. Yes." I was almost sobbing. I could not believe I was so
useless that I had let myself get into this state. Why did I forget such
simple things? Why was I just so unable to look after himself?
"Well, if you are sure," Eve looked at me, as I nodded, "then we can
perhaps be more firm and clear in our training. Would that be what
little useless Chrissie sissy needs?"
"Yes, please, just give me another chance." I realised he was now
begging for punishment. I knew that this would be worse punishment than
I had had so far from Eve, and those spankings had been so sore, but I
also knew I needed it. I so needed to be Eve's sissy maid and if that
meant a little punishment to make the maid Eve deserved then I would
take than punishment. Gladly.
"Good then. That is agreed. Go to your room and open the bottom drawer
of the tall-boy and dress in the items there. Then come back here where
I will wait for you." Eve dismissed me and I almost ran - or as much a
run as the 6 inch heels would allow - my room.
Once in my room I quickly tugged off my dress and underwear. I noticed
as did that one of my stockings had a run already - no wonder Eve was so
angry with me. I convinced myself that I did deserve this punishment.
I pulled open the bottom drawer. I had not yet even looked in this
drawer but then again there were two chest of drawers as well as this
tall-boy and I had not had a chance to explore every space. The drawer
was full of underwear - but not sissy underwear. This was black and red
cheap tart underwear. The black bra was large, padded to the 38DD cups I
was almost used to but frilled in red lace and just shouted out 'slut'.
The high cut thong was similar. The tight waspie suspender belt matched.
The fishnet stockings were almost not a surprise. I pulled on the
outfit. At the bottom was a black bob wig. Once on, I looked in the
mirror. A cheap slutty tart looked back.
Under the wig right at the bottom of the drawer was the highest pair of
heels I had ever seen. They black patent ankle boots - lace up with lots
of cut-aways in the leather - so many they were almost sandals, but
definitely boots as they laced up his ankle. But the design of the shoe
was not the most striking feature - that was the near vertical position
of the sole, thrust upright by the 7 inch steel heel. I held the boots
in almost fear; how would I walk in these? How, even, would I stand? I
sat on the edge the bed and pulled the left one on. My foot was forced
into an extreme arch. As I tied the laces this arches my foot and pulled
up my toes even more. The same for the right foot. This was almost
painful, yet exquisite at the same time. I stood, or tried to stand,
holding onto the side of the tall-boy for balance. My whole weight was
on my absolute tip-toes. I knew Eve was waiting so I just had to get to
her boudoir. I tried a step - impossible without holding onto something.
So hanging of furniture or leaning against the wall, I tortuously made
my way down the hall to Eve. And the certain punishment that awaited.
I stumbled into Eve's room. It was dark, and I struggled to focus on
where everything was so I could walk into the room and keep my balance.
"Come in Chrissie." Eve spoke from the shadows in one corner. I found a
wardrobe at that side of the room and holding onto it stepped into the
room.
"Chrissie, are you ready?"
"Y-y-yes." I now felt real fear. The casual yet cold tone in Eve's voice
I recognised as the precursor to a hard spanking. Yet I also knew I had
to be spanked. It was my punishment and I deserved it.
Eve switched on the lights. I blinked as the room became clear but all I
could focus on was Eve. She was dressed top to toe in shiny black latex.
I gasped at the sight of the rubber goddess in front of him. She wore
the tightest latex cat-suit, with a zip very visible under the crotch,
her waist was pulled in severely by a rigid black rubber corset, this
only came up to her bust, and what a bust. Her cat-suit had enormous
false breasts, great cylinders of breast, each topped with an engorged
black teat. She wore shoulder length latex gloves and thigh high boots
with 6 inch heels. But most frightening was that she wore a full latex
hood, with only openings for her eyes, nostrils and mouth.
This cruel vision in latex had held my gaze. It was only when Eve
stepped up to me, held my elbow and firmly pulled me into the side of
the room, that I noticed what I was being pulled towards - a metal
frame. This was a large, solid frame with hooks and straps. I shuddered.
He knew it was for me.
Eve took a blindfold and tied it onto me blocking out all the light.
Then I felt leather straps being placed over my head and an enormous
ball gag being forced into my mouth. I dumbly complied as Eve strapped
the ball gag on, with a strap under my chin and two straps over my head
- plus a thick strap round my neck, buckled quite tightly.
I felt himself being pushed into position within the frame. Thick
leather wrist straps were tightly buckled on and I felt my arms being
pulled together behind my back. Another two sets of straps were tight
tightly at my elbows so I was arching my back with my elbows almost
touching. I breathed heavily through my nose.
I felt a thick belt, almost so thick it was like a short corset, being
wrapped round my waist and tied very, very tightly; squeezing my already
corseted waist further. Then, to the sound of ropes swishing through
bolts and metal rings on the leather belt, I suddenly was aware that I
was being pulled up be the ropes. I just made out the sound of a small
electric winch slowly winding the ropes tighter and tighter. First, from
the waist I was lifted from the ground and I felt the straps round my
head take the strain and lift my head up. Then, and most uncomfortably,
the cuffs on the wrists also lifted, pulling my arms even further back.
Within a minute I was swinging slightly - fully off the ground - with my
feet reaching out for some purchase but finding only air. I felt a
gloved hand stroke my bare bottom cheeks. "Now Chrissie, you are ready."
This was not a question and it was not about how I felt - which was
truly terrified. I had had enough time with Eve to know she was at best
unpredictable and certainly at least a little sadistic. I moaned into
the ball gag.
"Yes sweet, this is so very exciting, isn't it?" Eve purred in his ear.
"Now be a good little slut and let me hear you moan some more as we take
our punishment."
Then it began.
Each thrash of the cane was like blinding, searing pain of light across
my whole body. Each stroke made me writhe in pain, even with the tight
bindings. Somewhere, from the edges of my awareness I heard Eve count
out each stroke. And each stroke was all I felt. Nothing else seemed to
exist. The relentless stroke and after agonising stroke. Tears flowed
from the first stroke and dripped, with the frothing saliva from my
gagged mouth into an ever widening pool on the wooden floor beneath me.
I had no idea how many thrashes Eve planned for me. The cane sliced onto
me buttocks as Eve placed each stroke slightly higher, then slightly
lower than the last, alternating the placement from cheek to cheek.
Vaguely I heard "thirteen" and a pause, then another blinding slice of
pain, and "fourteen"... Eve was not rushing this, almost pacing herself
for a long session of whipping. After "twenty two" I stopped hearing
Eve's voice. After "twenty nine" I passed out.
Chapter 6 Chrissie and Dirk
I felt himself come to. My bottom throbbed in pain but the caning had
stopped. I tried to move but I was still tied and suspended in the
frame. I now could not even move his feet. They were no longer hanging
down but where tied tightly. It felt like my heels were tied to my
thighs and these in turn also were now taking the strain of my body.
Then I heard a voice. "Oh I just knew it, Eve!" It was Dirk. I writhed
in acute embarrassment - almost forgetting the pain of this flayed
bottom. Dirk was seeing me dressed like a little slut in tarty
underwear, with me tied up and exposed.
"Eve, you have excelled this time. This is a real outcome. Look at this
slutty sissy. She is near perfect." Chris heard Dirk walk round him. "Oh
and look at that arse - you certainly gave him a good thrashing. Those
bruises will take weeks to heal. That is such a pretty sight."
A hand touched my tender bottom causing me to wriggle. The finger ran
over the now raised red welts, each stroke burning. "Oh how very nice."
Then Eve's voice. "Yes daddy, this sissy was the easiest. Chrissie was
quite desperate to be my little maid and to prance about it sissy
undies. He even seemed to like the punishment - although I'm sure he did
not expect this. He came to the frame quite willingly. He knows his
place and knows he needs training. It's so sweet."
I felt Dirk's hand move down my buttock and between my legs. "Get me
some lube, Eve honey. This sissy is ready for her final breaking in."
I heard Eve laugh. "Of course, here's a tube. Chrissie will love your
big cock daddy. I just know it's what he's being secretly dreaming of
all this time."
My brain was trying to process all this new information and my body was
reacting the Dirk's rough fingers as I pushed into my rosebud and
smeared lubrication up and into my hole. What was going on? Dirk knew
that Eve would dress me as a sissy maid? Oh god that fingering was good,
my cock was now getting hard, swelling in my lacy panties. And Dirk
wanted me to be a sissy? Oh, that must be two fingers, oh shit, that
feels so nice. My brain was no longer able to process rational thoughts
as I reacted to the rogering that Dirk was giving me.
Then I felt his fingers pull out of my hole. And the thong be pulled to
one side.
"Oh Eve, this is a tight little tramp. Pull my monster from its cotton
cage, honey, I'm going to give this slut a full Dirk fuck." I heard Eve
giggle and some clothes being removed, then I felt Dirk's hands on my
hips and his hips between my legs. Then his cock head against my hole.
"Oh you are a lucky sissy, you are Chrissie," Eve whispered into my ear,
"you are getting daddy's lovely big cock. I know of sissies who would
beg for the monster that is daddy's cock and you are getting all to
yourself."
And at that I felt Dirk push his cock into my hole. It was a huge piece
of tumescent flesh - hard, thick and long. I screamed into the ball gag
as Dirk split me open like I'd never been opened before. I'd played with
my bottie with my finger and one of mummy's dildos but this was whole
different size. This was huge. Dirk did not spend time on a soft, slow
build up. He ploughed straight into fucking me hard; thrusting his meat
as far up my love tunnel as he could. He held my hips and pulled me down
onto his monster cock with each thrust. He banged his balls hard against
my little plums as he tore into me. then with a roar he spurted his seed
deep into my bottom. And with one final extra deep push, he pulled back
and his cock literally popped out of my arse.
As the long drips of cum slipped from my bottom, and my sphincter pulsed
with the sudden departure of the filling cock, I felt my ropes being
loosened. I was being untied and lowered. Soon I was out of the frame
and I felt soft hands undo the buckles of the ball gag, lift it off and
pull off my blindfold.
I was cuddled into a soft bosom as I sobbed great sobs of pain, and joys
and exhaustion.
"There, there Chrissie, you are a girly now." It was Paige. She stroked
my hair. "We've all known you were a little sissy. I've wanted a sissy
daughter and Dirk loves a little sissy. We planned this baby so you
could be the sissy of your dreams and everyone's dreams. We just needed
to give you that tiny push over the edge to full sissiness. And Eve
loves breaking in new sissies. There, there. You are home now."
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