Sissy Stepson 10 Stepmother s Sissy
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One Step At A Time (Part 6) free porn video
One step at a time
Step 10
After his experience at the hands of Wendy David felt both confused and in
some discomfort. His first experience of a butt plug had not been a
pleasant one and she had been both insistent and forceful. His body had
naturally resisted the unwelcome intruder and his muscles had contracted
to try and halt this violation. But she had just kept the pressure on the
plug. Eventually the plug had slid home and Wendy had told him to
straighten up slowly. It was hard to describe the sensation. She explained
that she was being gentle but that he should be in no doubt that she would
be using ever larger plugs as his body became used to them. He then had to
continue working in the shop for another hour with the plug in place.
After completing his work he was relieved when Wendy again bent him
forward over a counter, lifted his little skirt and pulled down his little
frilly panties to remove the plug.
What David didn't know of course was that all of this of course had been
planned between the 4 women. They had been friends for some time, partly
because they shared the same interests and views on exactly how men should
be treated, although Deborah had been a more recent addition to the group.
Based on the knowledge gained from her mother and her aunt, Deborah had
decided that it was best if each of them played out slightly different
roles. Wendy was to be the harsh dominatrix type who would introduce him
to various sexual elements of his new role as sissy and maid. Jane would
also adopt a harsh role, but with the added twist of unspoken blackmail,
given that she was after all his line manager. Sandra would play a more
subtle role taking on the physical transformation side of the whole
process. But of course it would be Deborah who would be in ultimate charge
of the whole thing.
At first Deborah had thought of having him give up his job completely. But
after some thought she decided that keeping him in his job offered
interesting opportunities for him to learn his new secondary and
submissive role, and this would be done in public. A lot of the time she
also found herself acting as the voice of moderation telling the other
three to not rush things so much. Deborah understood the importance of
gradual changes. She had thought for a while about whether Wendy was right
to force herself on him at this stage and violate him. But on reflection
she could see how it was important to plant the idea in his head that
normal sex was now out for him and that he was completely theirs to do
with as they wished.
David undressed as he felt the need to shower and try to rid himself of
the memory of what had happened earlier. He took off the black hipsters
and the white blouse that Jane insisted he now wore at work. He stood for
a moment in front of the wardrobe mirror looking at his image in the
frilly pink lingerie and stockings. He smiled. Slipping out his lingerie
he walked into the bathroom and he began to shower. As he cleaned himself
he noticed that the marks from the beating with the ruler were still there
on his bottom, even if they were fading.
Feeling slightly better he stepped out of the shower cubicle and wrapped a
towel around his body. He walked back into his bedroom and was shocked to
see Deborah sat on his bed. He stood still for a moment, confused.
"How did you....?" he started to ask.
But she silenced him with a wave of her hand.
"Drop the towel and kneel in front of me," she ordered.
He thought just for a second and then released the towel and dropped to
his knees at her feet.
"Today has been a big day for you in fact the last few days have been
quite an eventful period in your new life. You need to understand your old
life is over."
She reached out and tenderly ran her fingers through his hair.
"While you have been at work I've been making some changes - go and look
in your wardrobe and in your drawers."
He stood up and walked to look in the wardrobe and in the chest of drawers
next to his bed. All of his male clothes were gone. In the wardrobe now
hung his pink taffeta dress that he usually wore at Deborah's, but it had
been joined by other similar dresses in pale blue, peach and a floral
pattern. Next to the dresses hung several starched tulle petticoats also
in a range of girly colours. Even his male shoes had been replaced with
range of ballet pumps, stiletto heeled shoes and even a pair of knee
boots. The same was true of the drawers where all his boxer shorts and t-
shirts had disappeared. On top of the chest of drawers there now stood
several different bottles of female perfumes - clearly indicating that he
was now supposed to wear these.
"Come back here and kneel."
He walked back over to over and knelt on the carpet again.
"You now belong to me - understood?" she asked.
"Yes" he replied, his head looking down at the floor.
"Yes what?" she demanded.
He paused for a moment, confused. Then he suddenly understood.
"Yes Mistress."
Deborah smiled to herself - mission almost accomplished - and nodded.
"Now you know your place we can start to move things on. You will be
growing your hair and we're going to take your colour lighter, a lot
lighter. You will also be having a perm once there is enough length to
wrap around the curlers."
He couldn't stop his hand from rising to feel his hair. He had sort of got
used to the lighter colour but the thought of going a lot lighter and
being permed was a huge difference. How would he be able to explain that
away?
"Wendy will continue her training of you so that become used to wearing a
large butt plug. In time you will wear a plug all of the time and at
night. Now, go and put on your baby doll nightie and matching little
knickers."
He walked over to his and slipped into the pale blue nightie and the
little frilly knickers that went with it.
"Come and show me," she ordered.
David stood in front of her clad in the very girly nightie and panties.
Although she had seen a picture of him in this outfit, in person it was a
very different thing. The pale blue colour was perfect and the delicate
lace frills were a joy to see. She also enjoyed how small and weak it made
him look, and he was clearly embarrassed stood before her in the
wonderfully feminine ensemble. She stood up and ran her fingers through
the lace frills. She ran a firm hand over his bottom clad in the frilly
satin garment. There was just one thing missing. She picked up her handbag
and took out a small silver cylinder. With her other hand she took hold of
his chin.
"Hold still and pout as if you were to kiss someone."
Confused a little David his as he was told. She turned the bottom of the
cylinder and a bright scarlet lipstick emerged. She began to apply a thick
coat of lipstick to his quivering lips. When he realised what was
happening he found it difficult not to pull away. Maybe pale pink nail
varnish he could just about get away with but lipstick? Red lipstick?
She stepped back slightly to look at the result of her handiwork. She put
down the tube of lipstick and took a paper tissue from her bag and blotted
his lips to remove any excess. Perfect she thought.
"Whenever you are not at work you will wear this lipstick - understood?"
"Yes Mistress."
Deborah placed the lipstick on top of the chest of drawers next to the
collection of perfume.
"You will continue in your current job and you will continue to do
whatever Jane tells you to do. You will wear whatever she tells you to
wear. Understood?"
"Yes Mistress," he mumbled.
"Before work tomorrow you are to go and see Sandra at her hair salon. She
will be making a couple more changes to your appearance so you need to be
there at 8am."
Having given her final instruction Deborah stood up and left the room. He
heard the front door slam shut. He stood for a moment thinking about
everything that she had just said to him and the implications for the rest
of his life. He walked to look in the bathroom mirror as he wanted to see
how he looked in red lipstick. He was surprised to see just how much
difference the addition of a coat of lipstick to his lips made to how he
looked.
Step 11
The persistent ringing of his alarm clock broke into his sleep. He sat up
to silence the alarm and noticed the red smear on the pillow case - he had
forgotten to take the lipstick of! He climbed out of bed, aware that he
still sore after yesterday's treatment from Wendy. He showered quickly as
he couldn't afford to be late for his appointment with Sandra. After
applying the perfumed body spray he began to dress in a clean set of pink
frilly lingerie. He noticed as he slipped into the feminine clothing that
each time it was getting easier to dress in the female garments. Strangely
he also noticed that the more he wore the lingerie the more they felt like
his "normal" clothing.
Having put all of his lingerie on he couldn't resist standing in front of
the full length mirror to enjoy the reflection of himself clad in such
lovely clothes. He turned left and right to make sure he got a proper view
of how he looked. He once more spent several moments fluffing out all of
the lace frills that covered his underwear. In particular he spent extra
time arranging the frills and ruffles on his little knickers. Happy that
the lingerie now looked its best he dressed in the white silk blouse and
the black hipster trousers. Finally he went to the wardrobe and took out a
pair of the black ballet style pumps. He wasn't yet ready to venture out
in heels so this choice of possible footwear was possibly the least worst
option. The pumps felt strange on his feet but he had to admit that they
did go well with the hipster trousers.
As a final touch he picked one of the perfume bottles and tentatively
sprayed a cloud of the scent into the air. He felt the sticky droplets
falling around him and clinging to his hair, his clothes and his skin. His
heart sank a little. There was simply no way that the scent could be seen
as anything but a woman's scent. He grabbed a coat and dashed out the
front door as time was passing and he had to be on time for his latest
appointment.
With barely minutes to spare he arrived outside the salon. He knocked on
the locked door and a moment Sandra appeared and let him into the salon.
"Hello sissy. My my look how you have changed. Let me have a good look at
your outfit - turn around."
Self-consciously he stood in the middle of the salon and turned around
slowly.
"You do look cute in that outfi,t" she said smiling. "Now I think we need
to go upstairs to a more private room."
She walked to the back of the salon and through a door which lead to a
stair case. David followed behind her nervous about what was going to
happen next. On the first floor Sandra walked into a small room also
decorated in pale pastel colours. In one corner was a waist high leather
table that looked like a sort of doctor's table.
"Strip down to your underwear and lie on your back on the table."
He slowly stripped off his blouse, trousers and pumps and lay down on the
table.
Sandra slowly slipped his frilly knickers down to his ankles. She paused
for a moment to slip on a pair of latex gloves and then began to inspect
his pubic area closely. Satisfied that he was hairless she picked up an
antiseptic wile and began to thoroughly clean his pubic area. David
flinched as the wipe felt cold against his skin and also stung slightly.
She then pulled over a stainless steel table that was fitted with some
kind of machinery that he didn't recognise. She picked up what looked like
a sort of cross between some kind of drill and a sewing machine.
"This is going to hurt sissy - be brave!"
Sandra turned on the tattoo gun and bet over his naked crotch. With one
hand she pulled the skin taut and then started to apply the tattoo needle
to his skin. David grimaced as he felt the needle rapidly jabbing in and
out into his skin. She concentrated as she began to write the wording she
had been told that Deborah wanted permanently imprinted onto his skin. He
could only speculate over what picture was being drawn onto his skin.
After about 20 minutes worked she switched off the machine and wiped his
skin with another wipe. She inspected her work closely and smiled - it was
just what she hoped it would be.
"That's going to be sore for a while but once it has healed over it should
be fine. Have a look before I cover it with a dressing."
David sat up and with some nervousness looked down at his crotch. Sandra
held a small mirror so that he could see the wording now etched onto his
skin. In bold black ink were the words "Property of Deborah" set within a
rectangular box in red ink. She covered the tattoo with a dressing, pulled
his frilly knickers back and then told him to get dressed again.
He swung his legs down from the table and stood carefully as his legs felt
somewhat unsteady. He put on his blouse and hipster trousers, and slipped
his feet into the black pumps. He glanced at his watch as he had to make
sure that he was punctual as he really didn't want to face another
punishment at the hands of Jane.
"May I go now as I have to get to work?" he asked.
Sandra nodded and so he went back downstairs, walked through the salon and
headed for his office building. The hipster trousers were pulling against
the recent tattoo and he would have to be careful for the next day or so.
Once at the familiar building he went straight through to his small
office. Well, he intended to go straight to his office until he was halted
mid-step by a shouted command from the direction of Jane's office. He
headed for her corner office and knocked and stepped into her office
through the half-open door.
"Close the door."
He closed the door behind him. He was nervous now as her tone clearly
suggested that either she was not in the best of moods or that he had done
something wrong. Whichever it turned out to be he was pretty sure that it
would involve some kind of punishment on his part.
"Would you like to sit down or would you rather stand?" she asked with a
smirk on her face.
David looked puzzled and then he realised with horror that Jane must know
about his ordeal at the hands of Wendy the previous evening.
"I'm sure you'll get used to it and you might even come to enjoy it," she
laughed. "Now, show me your new tattoo."
Somewhat reluctantly he undid the hipster trousers and pulled them down to
his knees. Then he put his thumbs in the waistband of his little knickers
and also slid them down to his knees. Jane walked over and pulled back the
dressing to inspect the new tattoo.
"Well you can be in no doubt about your position now can you? Get
dressed."
He readjusted his clothing and stood waiting to see what Jane wanted next.
"I have a lot of important meetings today so I'm going to be tied up for
most of the day. But I have a list of things that need doing and errands
that need to be taken care of" and she handed him a typed list. "Now run
along and get busy."
He took the list and walked back to his small office. As he read down the
list he saw that they were the kind of things that a personal assistant
might do, rather than someone who was a junior supervisor as he was. He
took his coat and went to make his way to the dry cleaners to collect
Jane's clothing. He had a feeling that today was going to be something of
a long day.
Fawn
- 26.01.2021
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