Sissy Stepson 10 Stepmother s Sissy
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Sissy In The Making free porn video
Chapter 1
Jim arrived at the North Carolina motel Saturday afternoon as he wanted
to make sure everything was in order for Mistress Cleo's arrival on
Sunday, as per her instructions. He had gotten the suite to insure there
was enough room and comfortable for his new found Mistress. A Mistress
he had never met, but already under her control.
He began to lay out the items he was instructed to bring, maids outfit,
bras, panties, stockings, and every female garment he thought might be
needed. A number of dresses along with two bikinis. There were five
pairs of heels, all with four inch heels, and a low heeled pair of pink
slippers. Next were the lipsticks, cosmetics, make-up, hair dyes, and
feminine products he was also instructed to bring. Two wigs were
carefully placed on the bed, and of course the CB3000 he was told to
purchase. He was instructed the only male clothes he was to bring was
the clothes he was to arrive in, polo shirt, sweats, and sneakers. Two
bottles of wine were placed in the refrigerator, and peignoir sets
purchased at Victoria's Secret for Mistress Cleo was neatly wrapped on
the work desk.
Jim was also told to use his imagination when purchasing an outfit for
Mistress. It was her intention to go out and celebrate on the town after
meeting with Jim on Sunday, and wanted to look her sexy best. These too
were neatly wrapped on the desk. A red dress, with black stockings and
matching bra, panty, and garter set. He chose a pair of red, open toed
heels for shoes. He did not wish to make Mistress upset, and did his
best to find something he thought she would like.
Jim did not sleep well, and Sunday morning ran the last few errands he
thought needed to be run before Mistress's arrival. Some small snacks and
flowers were the last purchases as he anxiously awaited her arrival.
Precisely on time there was a knock on his bedroom door as he nervously
opened it, and there stood Mistress Cleo, dressed casually, she pushed
past him as he closed the door. With fingers pointed to the ground he
knew what she wanted as he bent to kiss her feet. Her exquisite beauty
was obvious in spite of the casual dress, and her domineering nature was
apparent. Enough. He raised, but as he began to speak, was quickly
slapped with a strong hand that sent him backwards. Not a word until I
tell you, understand, slave, or is that sissy, as Jim just nodded, and
Mistress smirked. Good. I want to hear only Yes Mistress, No Mistress,
until I say something different, understand sissy. Yes Mistress. Good.
Now get me a glass of wine and strip. Jim brought the wine and began to
fumble with his clothes. Get on with it sissy, and get used to it, there
will be no privacy for you. Come here, as I inspect you. Mistress
raised her foot lifting up Jim's balls and penis, and just laughed,
fucking useless she laughed. Yes, sissy, it will be, that is what you
are, a sissy, as she gave them a slight kick. She pulled out a tube of
lipstick as she marked a triangle around Jim's privates. In the shower
now, and shave everything else except what I marked, legs, arms chest,
and hurry back in here.
Mistress relaxed as she heard the shower and waited for her sissy to get
back.. Lets have a look. Not bad sissy, but we will do a more expert job
in the days to come, in the meantime bring me your chastity tube so we
can get down to business. Jim handed Mistress Cleo the device with a
bent head, as she went about securing it. Much better she smiled as she
locked it into place. Holding the keys to his face, Mistress dropped
them into her purse. Consider these lost for 30 days sissy, we will see
what happens then she said with a smile.
Now before I jump in the shower and ready myself for a night out, lets
look at what you bought me, and for your sake it better be something I
like and in the right size. Very nice sissy, as Mistress opened the
dress box, beautiful she smiled, and in the right size, you are making
points. I love the shoes, Sexy. My goodness look at these as she held
the shear panties in her hand, with matching lace bra and garter. The
expensive black thigh-hi's completed the outfit. I know someone who
won't be able to wait to get me out of these tonight, and it won't be you
sissy, right. Yes Mistress.
Ok come kneel outside the bathroom door and wait while I take a shower,
as Mistress picked up the panties and headed for the bathroom.
Everything in there I told you to get sissy? Brush, shampoo, lotion,
razors, powder, my perfume. Yes Mistress. Good, now kneel here and wait
for your Mistress, like a good little slave.
It was a while before Mistress opened the door and stood before her sissy
in only her panties, intoxicating him with her beauty and smell. Mind
your place sissy and get the moisturizer, you need to apply it to my
beautiful legs before giving me a pedicure. Mistress was sipping her
wine, and pointed to the floor. Sit there as she pointed her toes in his
face. I want you to rub lotion on my legs and keep your eyes fixated on
the pussy that owns you, the pussy you will never have, the pussy you
will learn to worship and serve. Enough she said after awhile, as she
put her large toe in his mouth, suck, that was delightful. Oh sissy this
too is wonderful, but lets save this for another time, and you are being
most respectful, Yes sissy Jim, you do have potential. Your Mistress
now needs to get ready, help me with my bra, that is your reward for
being a respectful slave.
Mistress Cleo continued to get dressed with sissy's help and he could not
help but admire her beauty as she applied her makeup and put on the
finishing touches. Good enough to eat, yes sissy. Yes Mistress, you are
very beautiful.
Now before I go, I have some paperwork for you to sign. I also have a
list of your duties that you will begin starting tomorrow. You will
study them tonight and I will leave copies of the signed documents for
you to read over. I have asked my mother, Mistress Wanda to assist me in
training you as a domestic. She will be here tomorrow at 6 to pick you
up and bring you to my house. You will be ready and have coffee ready
for her when she arrives. Everything you will need is in the paperwork,
study it tonight. Most likely I will not see you till later in the day
as I am planning to have a late night. Mistress Wanda will instruct you
on what needs done. Now here sign these.
No, there is no reason to look them over sissy as he began to look at the
paperwork, you want to be a slave, and you will be. Sign. Very good
sissy, as Jim signed the papers in front of him. You have a goodnight
now sissy, and get some rest you have a busy month ahead of you, I know I
will enjoy myself as Mistress Cleo walked out the door.
Chapter 2
Mistress was more than Jim could ever have imagined, and his thoughts
turned to how beautiful she was, and how lucky he was to have found such
a Mistress.
He sat down to read the instructions and what he had signed . The first
was a power of attorney giving Mistress Cleo complete control over for
him for 30 days. His first instincts was that this was crazy, but his
gut told him that he was on the right path, that Mistress was different,
and he was at ease. His thoughts turned to how best he could please the
woman he had just met. The second signed document was a service
agreement, agreeing to serve Mistress Cleo in any way he was instructed,
to be dressed as was directed, and agreeing to any modifications Mistress
deemed necessary to complete a successful training program.
He continued to read the instructions. Sissy you are to be ready by 6am
and Mistress Wanda will be picking you up. Your service to me begins in
the morning. It will be long and arduous, but in the end you will be the
domestic slave you wish to become. You are to begin your day at 5.
Everyday. You are to ready yourself and be prepared to start each day at
6. Your service will end at 9pm, with lights off at 10. This will allow
enough time to prepare yourself for bed. Each morning you will do your
best to get yourself together and ready yourself to be the sissy slave
you wish to be.. I expect to see your nails freshly polished each and
every day. Full sissy makeup, and you will remain and learn to serve in
heels from early morning till you retire at night. Expect your feet to
be screaming by nights end, but maybe in time you will get used to it.
I do not expect perfection but improvement every day. During the month I
will arrange a salon visit to help you with improving your look.
You will be responsible for all domestics in my home. Cooking, laundry,
and cleaning will be just a small part of your duties. Next week, and
each week I will expect to see a breakfast, lunch, and dinner menu that
you have prepared for my approval. You will be responsible for all
grocery shopping. You will be expected to keep my home in perfect
condition. I will expect my bedroom sheets to be changed everyday,
along with fresh towels in the bathroom. Don't ever let me run out of any
personal feminine products, that too is your responsibility and would
result in severe punishment if I lack anything.
We will be entertaining on the weekend so I want the bar to be well
stocked with liquor and beer. Make sure there are cigarettes and cigars
also on hand. This will also be your responsibility. By the way these
are adult pleasures and you being a sissy are not allowed to indulge. I
will allow one cup of coffee each day, but you are not to smoke or drink
alcohol.
I want candles in the bathroom, flowers on the table, my clothes to be
washed and ironed, including underwear. I will expect my drawers to be
organized, the windows cleaned, and toilets spotless.
I expect to be pampered at every turn. According to your application you
are an accomplished masseuse and know aromatherapy. You will put that
knowledge to good use and often.
Now I want you to get some rest so you can start your new life as my
slave, well rested. You have a lot do do before Mistress Wanda gets
there in the morning, doing your nails and getting your sissy self
prepared. Be happy that your Mistress is having the time of her life,
eating, drinking, and dancing. That a real man will be enjoying my
company tonight, and a Mistress who you will learn to serve.
Jim was up early and prepared himself for Mistress Wanda's arrival. He
again shaved all over except for the patch that Mistress Cleo had
outlined the day before, and gave himself a pedicure. As he moisturized
his legs and slipped on his panties he was already feeling the effects of
the chastity cage. How was he going to endure 30 days he thought to
himself, but he needed to put that aside, get coffee on, and finish
getting dressed. He was to pack a day bag with the rest of his outfit,
but was to put on his sweatpants, sneakers, and polo and wait for
Mistress Wanda.
The knock on the door startled Jim out of his daydream. Good morning
Mistress Wanda, as he opened the door. Sissy nice to meet you, and I
heard a lot about you, but first get me a cup of coffee, black is fine,
and come sit at my feet as we get a few ground rules down. Mistress was
an imposing figure, tall, in-shape, matronly looking, and Jim was
thinking maybe mid-sixties.
I have been asked to help in your domestic training. When I say, help, I
mean, I am there to help guide you along, point out anything I might find
you doing wrong, and keep you on task. I am a busy woman as is your
Mistress Cleo and have more important things to do than constantly
supervising a sissy to do their required domestics. Today I will be
showing you around the house, making sure you are in proper uniform, and
correcting any flaws in your service. I will warn you now that you do
not what to show me any disrespect, and I expect to see your chores done
on time and to perfection. You are to address me as Ms. Wanda, I am not
your Mistress.
Yes, Ms. Wanda. Good now that is out of the way, Mondays, is shopping
day. Each Sunday you will give to me and Mistress Cleo your planned menu
items for the week, do an inventory of your cleaning supplies. and
toiletries needed to sustain the week. You will also ask me and Mistress
Cleo if there is anything special we might want, or need for the week.
Perhaps some feminine hygiene products, or an outfit we could use, maybe
some lingerie for the men in our life. Mondays will be the day you do
all the shopping for the week so you will need to be organized. The rest
of the week will be spent cleaning, cooking, and looking after our needs.
Now lets get moving, as Ms. Wanda handed me a list. I will show you
where the food store is, pharmacy, liquor store, and mall.
It was early afternoon by the time we reached Mistress Cleo's home. The
car was packed and took some time for me to bring all the bags in. I
will tell you this once where everything goes sissy, by next week you you
will have everything figured out I am sure. Don't be banging either when
you are putting everything away, your Mistress is still resting, I
understand she had a very late night, and wild morning, and does not wish
to be disturbed she said with a smile.
Now before you put everything away you need to get into uniform.
Tomorrow I expect to see your breast forms attached, it is getting late
so no need to do that now. Same goes for your nails. The only day you
will not be fully dressed is Monday when you go to the stores, that might
change after 30 days but for now we do not want to bring too much
attention to ourselves. Besides it will take some practice for you to be
a presentable sissy. For now just put on your serving skirt, thigh-
highs, and you serving shoes, as that will take some time getting used
to.
It took another two hours to get everything put in it's proper place, and
by now my feet where already feeling the pain. Bring me the gifts you
got me at the store sissy, Ms Wanda said, I will be going, as I will not
be needed anymore today. When I leave your Mistress wants to see you.
Your are to bring her coffee, juice, and some toast lightly buttered to
her bedroom, she is waiting. I will see you at six, and make sure you
are properly attired.
Chapter 3
I readied a serving tray with the items I was told to bring. I decided
to bring a small vase of flowers hoping Mistress Cleo would approve, and
nervously walked cautiously up the stairs to her bedroom. I was still a
little unsteady in the heels so took my time not to spill anything, and
gently knocked on her bedroom door. Enter!
As sissy walked in, he could not help but admire Mistress Cleo. Sitting
up in bed, covered in a sheet, feet sticking out on the end, her nipples
peaking out from the top, he was taken back by her beauty. Put the tray
on the night table sissy and give me my coffee. I had a very long night
sissy and your Mistress is a little tired and a bit hung over, and I
could use to be pampered. I decided to speed some of your training up,
and give you the pleasure of doing just that. I danced for hours last
night and my feet are sore and in need of attention, so I want you to
start there. Did you bring up the paper. No Mistress. Then go get it,
I want to enjoy my coffee and read, while you massage my feet, and don't
let that happen again. Yes Mistress as sissy scampered downstairs to get
the paper.
Jim got the lotion and began to work the soles of one foot and then the
other. With thumb on the insole he applied pressure while massaging the
top of the feet, then to the balls of the foot, and each toe. Jim
lowered himself and slowly began to suck on the big toe. Mistress bit
her lower lip and she put the paper down as let out a low groan. Yes
sissy suck Mistress's toes each one. Lick in between them. Worship my
feet. Fuck this feels good. After considerable time went by, Mistress
pushed her sissy away with the other foot, very nice sissy.
Now sissy you-++ have more work to do. Hubby was insatiable last night,
and again this morning. I lost count how many times he came. Your
Mistress is sore, sticky, and very messy. I was just too tired to
freshen up, and besides that is what a sissy is for. Lets start with the
backside first, I think he came there only once, maybe twice she laughed.
My hesitancy was apparent, but knew better than question Mistress and she
turned on her stomach. Just pull down the backside of my panties slave I
don't want everything leaking out . You will get to that once you lick my
ass clean. Sissy lowered her panties and she opened her legs slightly.
Start at the bottom sissy and long stokes from bottom to top. Yes that's
it. Now deeper, bottom to top. Oh yes, again, and again, now deeper
stick that sissy tongue all the way in. Oh yes. Ok stop. Mistress
rested for a moment and turned over as she flipped the sheet aside.
Sissy slave I want you to carefully and slowly to remove my panties.
Your Mistress is sore and you are to be gentle. I want you to catch
first whatever is leaking out then slowly tongue the outside of my pussy
lips. As Jim lowered Mistress's panties he immediately caught the
massive amount of cum on his tongue. What's the matter Mistress Cleo
laughed, never ate cum before, well you better get used to it because
this will be happening a lot, and it is as good as it gets for sissies.
Sissy recovered after the initial shock, and continue for lightly rim the
the outer lips of her pussy. Mistress grabbed the back of sissy's head
and slowly pushed his tongue deeper. long strokes sissy, that's it
deeper, careful. Soon Mistress was rocking with her slave, that's it
sissy, faster now, don't you dare fucking stop, fuck, as Mistress began
to tighten and orgasmed on her slaves face. As she kicked him off her
pussy, she told him to clean himself off, bring in a warm washcloth, and
gather the essential oils as she wanted a long massage.
Returning from the bathroom Mistress was again sitting up. Take the
washcloth and respectfully wipe my pussy clean slave. Now come stand
here for a moment to go over a few more rules, before you give me my
massage. Mistress grabbed sissy's balls and looked him in the eyes. I
bet you would do anything for me to take this cage off wouldn't you
slave. Yes Mistress. Anything? Please Mistress. Well that ain't
happening, but if you are willing to do anything after one day just think
what you will be offering me after thirty, she laughed.
Now a few rules before you start that massage. Remember when I told you
that sissies will be taught not to ogle, or stare,* at any woman, or be
punished? Yes Mistress. When you are massaging me, assisting me in a
bath, helping to get me dressed, I expect your eyes to remain in their
socket and you look at my feet, my head, but not be staring at my ass,
tits, or pussy, do you get that. Yes Mistress. Good. You will be
taught that the only time you will be allowed any of those privileges and
pleasures is when a woman is peeing, just got laid, or on her period. In
time you will cherish those times. Now get on with my massage as she let
his balls go.
Sissy was good at massage and paid attention to work every part of his
new owners body. Starting with the back, he slowly worked his way to her
buttocks, then to her legs and feet, before turning the Mistress. He
worked both arms, paying special attention to each of her fingers. When
massaging her breasts he lightly would pinch each nipple giving them a
little tug as he applied lotion to their undersides. It was well over an
hour before he worked the front side of her legs, finishing with the
feet.
Delightful sissy, but I am tired and need a nap. Go get dinner on and
get me in an hour, you can help me in the bath, and get me nice and sexy
for hubby, before I send you home for the night.
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