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The Appointment free porn video
The Appointment
"I am not a sissy. I won't be dressed as a girl. Go away."
The sissy was chained to his bed as usual when his mother came in to
make sure he was awake and thinking about getting ready for his
appointment at the Sissyboy Boutique. He was dressed in his pink baby
doll nightie and, of course, he was in nappies and plastic panties to
prevent the mattress in his cot from getting wet. As usual he was
soaked through because he had to drink a large bottle of juice each
night after being put to bed, and he had even occasionally soiled his
nappies when he was released later than normal.
"Oh dear. Are we going to go through this again? Perhaps I will get
Aunty Margaret in to help me get you organized, and you know that she
will take none of this nonsense." Margaret was her older sister, and a
formidable woman who had initiated the process that lead to Jamie
becoming a sissy. At 14 years of age he was uncontrollable but now,
only 6 months later, progress had been made despite the usual morning
outburst. At 5'9" he was slim and fine featured and he had all the
makings of a beauty, if only he would cooperate.
His mother sat on the edge of the cot and put her hands on either side
of his face as she drew him towards her. "Perhaps a wake up kiss will
settle my little darling down," she said looking directly into his blue
eyes that were wet with tears. She ran her tongue over his cheeks
collecting his tears, and then kissed him on the mouth in a manner that
she knew would both arouse him and make him more compliant. Although
she didn't like to admit it to Margaret, it aroused her too. She could
see his penis swell inside the nappies, and she put one hand on the
outside of the plastic panties to feel it grow further as she touched
him. He groaned with pleasure and forgot who and where he was for a
moment as he moved against her downward pressure. She felt him release
and watched as he closed his eyes and savoured the delicious feeling
that all sissies feel when they are allowed to cum.
She sat and stroked his lengthening blonde hair as he settled down and
finally used his little sweetly perfumed handkerchief to dry his eyes.
Finally his mother kissed him again before taking the key from its hook
on the wall and undoing the steel collar locked around his neck and
chained to the steel bars of his cot. He was chained this way each
night without exception, and he had initially found it hard to sleep
comfortably with the collar in place. At first his mother thought it
was an unnecessary precaution, but Aunty Margaret had insisted. She had
prior experience of a sissy who had tried to escape at night.
"Now. Into the bath, and when I come in I want to see lots of suds and
lots of perfumed oil in the water. Your clothes will be on the cot
waiting for you, and I think I will get Aunty Margaret to help you with
your makeup this morning, because we are to have such a special day my
darling." He got into the bath and his mother came in to help him wash,
making sure he got into all those nasty cracks and crevices that could
hold dirt.
Returning to his cot he looked in dismay at what he was to wear and,
despite trying hard not too, he burst into tears again. He seemed to
cry a lot more these days for some reason, and he had started to lack
the confidence to do things himself, often having to depend on his
mother or Aunty to help him dress, do his makeup and even prepare
himself for bed each night. He walked down stairs with a towel around
his waist to find if his mother was there to help him. However, Aunty
Margaret was sitting in the lounge room when he came in and she soon
sorted out that he needed help to dress.
"Up the stairs quickly Sissy. We have only an hour before your
appointment." As he walked upstairs Aunty walked right behind him,
occasionally slapping him on his bare legs with the little whip she
always seemed to have with her.
Soon, and without any fuss she had him in his tightest corset, a
heavily boned white with purple lace garment that he hated with a
passion. "Now bend over and take your plug darling." He obeyed, bending
over the changing table and gasping as the horrid thing was inserted
deep inside him. He was nearly always plugged this way and he had not
yet got used to the feeling of stretching and discomfort that occurred
until the plug finally slid inside and locked itself into place. Next
came his white lace training bra and matching white panties with a
purple ribbon in the front. Long white socks with lace tops and white
Mary Janes were next and then a multi layered petticoat under a white
long sleeved dress, with purple lace edging, finishing just above his
knees.
"Sit down in front of your mirror darling. We need to be quick now, so
I will leave your false eyelashes for next time."
Despite himself, he had begun to enjoy having makeup smoothed on to his
face. Today his lipstick and eye shadow was mauve and when Aunty put
his hair into short pigtails he had to admit he looked really cute,
especially when the purple ribbons were tied around each of them. "Move
your head from side to side honey. Let me make sure your hair is
sitting properly."
"Now, stand up. Turn around for me. Curtsey. Well, what a nice looking
Sissy we have today. Come with me."
Aunty Margaret took him by his right hand and led him downstairs where
she found Janette was already in the car waiting. She took his white
leather baby reins from the hook near the front door and slipped them
on, buckling and then locking them in the small of his back, before
taking the leash and leading him out to the car and helping him climb
into his baby restraint seat in the middle of the back seat. There was
a panel on the front of his reins which told the world that he was
Sissy Jamie.
Within 30 minutes they were at the front door of the Boutique where the
owner, Miss Catherine, was waiting for them. "Hello Janette, Margaret.
Here. Give me the leash and I will take him out the back to get
started. If I have trouble I will call you. My goodness he is quite
pretty isn't he. Well, today will be a true test of his capacity to be
a good sissy. Come with me darling." She pulled on the leash and almost
dragged the sissy through the boutique while at least a dozen women,
all impeccably dressed and most in leather outfits and black high
heeled boots, looked at him pass. Each of the women also had a sissy on
a leash of some description, and none of them looked any happier than
the newly arrived sissy.
"We have ten dresses that you are going to parade for my lady friends
darling, but you are to choose them from the selection on these racks
and I want you to choose a prettier dress each time. Get to it."
The sissy just stood there not knowing what to do, until Miss Catherine
took his leash and pulled him towards her. Looking directly into his
eyes she said "Get started sissy. I have a wonderful new little horse
whip that I have been waiting to try on a reluctant sissy, and you will
be the first to feel it if you don't move now."
He rushed over to the racks and quickly took off a wonderful pink dress
that would reach down to his feet. With lace and bows everywhere it was
a delight, and as he stepped into it Miss Catherine let his hair out
and brushed it to sit around his neck and frame his face prettily. A
pink bow, new pink shoes with 3"heels and locking ankle straps were
next. With his baby reins removed, Miss Catherine locked a gold plated
steel collar around his neck and, after attaching a chain leash, she
led him out onto the small stage for exhibition.
The sissy was petrified, but a few short and sharp commands had him
walking across the stage following Miss Catherine, and almost
hypnotized by the sound of her boot heels on the wooden floor in front
of him. He was made to walk backwards and forwards a number of times
until Miss Catherine was happy with his walk and his posture. As he
left the stage he was told to curtsey and the embarrassed sissy did his
best in his constricting corset.
Over the next hour he was to wear nine more dresses, each of them
getting progressively shorter and more transparent. The last was really
just a white lace short apron covering his underwear, and the women
watching were delighted to be able to see his panties, his bra and the
hated corset through the lace concoction. For his last parade Miss
Catherine also asked his mother to come up on stage and show him off,
which she did with great pride. After his last curtsey she kissed him
in front of everyone, and of course his erection became obvious to
everyone in the room, even more so when his mother touched it through
the lace with her fingers with luscious long pink painted nails. She
even ran one nail along the length of his penis and he shuddered with
excitement despite himself, and a little wet spot appeared where all
was dry before. To his shame he even noticed a number of the other
sissies looking at him with excitement in their eyes, although their
Mistresses were quick to whip any of them who gazed at him for very
long.
Finally, it was all over and he was back in the clothes Aunty Margaret
had dressed him in before leaving home. Miss Catherine lead him back
out into the room on his leash and handed it to his mother after
saying, "What a beautiful sissy you have Janette. He is a credit to you
and Margaret, but I do think that now you have taken him this far, you
should both join our little club. I think he would benefit by being
able to socialize with other sissies from time to time, and you of
course will learn much from the other Mistresses here. Perhaps both of
you would like to come back next week to select some leather outfits
and other devices that will be useful in his further training."
Two weeks later the sissy woke up in tears again, distressed at his
circumstances. He was wet and this time he had soiled his nappies
because it was late in the morning. When his mother came in he noticed
that she was, for the very first time, in a back leather full length
dress over leather boots with 4"heels. Her hair was swept up into a
ponytail and she carried a small whip, just like the one Aunty Margaret
had used on him."
"Stop crying Sissy." The whip lashed onto his bare legs before she sat
down beside him as she did most mornings now. "I can see we have much
more work ahead of us dear haven't we. I think I may have been a bit
too lenient in the past. Aunty Margaret and Miss Catherine have
convinced me that I need to take a much firmer hand with you." She
unlocked the collar. "Now get up, bathe and dress in your maid's
uniform. You have a lot of work ahead of you today." And his
transformation entered a new and critical phase.
Jo
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