Sissy Stepson 10 Stepmother s Sissy
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One Step At A Time (Part 5) free porn video
One step at a time
Step 9
David was awake early the following morning having had another restless
night. On returning home he had spent most of the evening tottering
around his house on the new 3 inch heels given to him by Deborah. His
feet and the backs of his legs ached from wearing the shoes. He
slithered out of bed and made his way towards the bathroom. In the
bathroom mirror he inspected his bottom following the beating he had
received from his line manager Jane. Thankfully the redness was fading
although there was still a degree of tenderness when he touched the
marks left by the ruler.
He stepped into the shower cubicle and stood for several minutes under
the warm spray hoping that it would ease some of the aching in his body.
He reached for the feminine scented shower wash and began to soap
himself all over, his body engulfed by the floral aroma. As he washed he
was sure that he could feel some re-growth in his body hair so he would
need to use the hair remover soon. He rinsed off and turned off the
water. He dried his hairless body briskly and then applied the body
spray.
As he looked in the mirror his newly lightened hair took him by
surprise, as did the new more feminine style. It was surprising how
sometimes just small changes could make a significant difference. The
removal of his sideburns and the softening of the edges of the cut were
subtle little adjustments which had a big effect on his overall look.
He walked back into his bedroom and took out a brand new set of the pink
frilly lingerie. He stepped into the frilly little panties and pulled
them slowly up his hair free legs. He enjoyed the feel of the lace
ruffles against his skin as he put them on. Once they were in place he
carefully arranged the ruffles so they looked pretty. Next he put on the
matching frilly pink bra - something he did with slightly less of a
struggle than previously, although it still felt strange to be wearing a
bra. The matching frilly suspender belt was fitted around his waist and
then he rolled the pink stockings up his legs and attached them to the
garter straps.
Before putting on his male top clothes he stood in front of the long
mirror on the inside of the wardrobe door looking at himself all decked
out in frilly pink satin lingerie. He ran his fingers over the ruffles
on his little panties and on the bra straps. He turned from side to side
to look at his reflection. He admired how the panties clung to his
bottom. He stroked the silken surface of the stockings. He suddenly
realised what he was doing. What the hell was going on? Was he actually
enjoying the clothes? Had he somehow switched from hating the clothes,
to tolerating the clothes, to enjoying them?
He dressed in the rest of his work clothes and set out for the office.
As he walked through the building and along the corridors he was aware
of the looks he was getting from of his colleagues. People would turn to
watch as he walked past and then whisper to each other. Some were more
open and clearly smirked at him as he passed. He hurried on to his
office and closed the door. Before he had a chance to door anything his
work phone rang.
"Hello?"
"My office. Now!"
He clearly recognised the voice of his line manager and he knew that he
better do as he was told and make his way quickly to her large corner
office. He knocked nervously on the door and then entered. Jane was
standing at her desk wearing a coat.
"We have a couple of errands to run before we do anything else so come
with me," she told him.
She ushered him out of her office and then headed for the stairs. David
rushed along behind her struggling to keep up with her brisk walking
pace. Once out of the building she headed straight for the nearby
shopping centre. He had a feeling that somehow this was not going to be
a pleasant experience and that it could only mean more changes. Inside
the large centre Jane headed purposefully for a small shop on the ground
floor. As they got closer he could see that the shop sold jewellery, so
he was a bit confused as to exactly why they were going in here. Jane
walked to the front counter and spoke to the pretty young girl who stood
on the other side.
"Hello, this is David and I'd like his ears pierced please."
Oh no, he thought, perhaps this was going to be worse than he had
originally thought. It was another external change which it would be
difficult for him to hide from the rest of the world. She also had
definitely said ears, plural. A guy with one ear pierced was fair
enough, but both ears pierced would be sure to draw even more attention.
"Sure, no problem. If you want to take a seat over in the corner then
I'll get Wendy to look after you," she replied.
"Come on David, over here," Jane said.
In the corner of the shop was a single stool next to a table with
various tools and pieces of jewellery. She pointed towards the stool and
David sat down nervously. Another young girl walked towards where he was
sat.
"Hi I'm Wendy, I understand you want his ears pierced - is that right?"
she asked.
"Yes, just a single piercing in each ear - for now," Jane replied,
grinning at him as she said it.
The girl took an antiseptic wipe and cleaned each of his ear lobes. She
then picked up the piercing gun and placed it against his left ear lobe.
David felt a sharp pain as the gun punched a small hole in his ear lobe.
She repeated the process on his right ear.
"There we go - all done," Wendy spoke. "What kind of ear rings do you
want in?"
"Just a pair of gold sleepers for now, something discreet for the
office."
Wendy put the sleepers in his ear lobes and then handed David a small
hand mirror. He turned his head left and right to see the result of the
girl's handiwork. Actually maybe it wasn't as bad as he thought it might
have been. Jane paid for the procedure and they walked back out into the
shopping centre.
"Now we need to get you a nice petticoat to sit under the skirt of your
pink taffeta dress."
He almost stopped dead in his tracks. How did Jane know about the pink
dress? If she knew about the dress, then what else did she know about?
But even worse, just how many other people knew what was going on?
Jane headed for the rear of the shopping centre. In the far corner was a
small shop that from the outside seemed to specialise in burlesque
clothing. They both entered the small shop and Jane walked confidently
to the woman behind the counter.
"Hello we're looking for a pretty petticoat for David here. It needs to
be very full, starched and preferably a nice pale pink colour."
He blushed red and he couldn't quite believe that she was telling other
people in such a public manner. The woman looked a bit puzzled but
headed towards a rack of petticoats on one side of the shop.
"If you want something cheap and cheerful then we have this one," and
she held up a nylon petticoat, "Or if you want something more impressive
then we have this one."
The woman held out a very short but very full pink petticoat. It was
made up of layers and layers and layers of starched tulle. The petticoat
rustled and crackled in her hand as she held it up for them to look at.
It was so full it was almost like a pink cloud.
"Can he try it on?" Jane asked.
David looked horrified at the suggestion but the woman just nodded and
pointed towards a small changing room at the rear of the store. They
walked into the small room and Jane said told him to strip to his
underwear. With trembling hands he peeled off his work clothes until he
was standing just in his frilly lingerie and pink stockings. She handed
the petticoat to him and he stepped into the middle of the ball of tulle
and pulled it up to his waist. The layers of material protruded out all
around him. Jane arranged the layers of the petticoat so that they stood
out to their maximum fullness. To his horror Jane then stuck her head
out of the changing room door and asked the shop assistant to come in.
"Can we just get your expert opinion please?"
The woman walked into the changing room and stopped in her tracks when
she saw David standing there dressed in frilly pink satin lingerie,
stockings and the pink petticoat. Then her expression softened and she
started to smile.
"Is this for a bet or something?" she asked.
No he's our little sissy," Jane replied. "Lift up the petticoat David
and show her your little knickers."
He kept his eyes firmly fixed on the floor as he slowly raised the
starched layers of the petticoat to show the woman his panties.
"Very pretty," she said. "And they go very nicely with the petticoat."
"Thank you, we'll take it then. You can get dressed now David."
The two women walked back into the sales floor of the shop and he
started to dress quickly after taking off the petticoat. Once dressed,
he stood deep in thought for a moment. Yet another person now knew about
his private secret. So this yet another person who now had both power
and control over him if she wanted to use it to be in charge of
everything that he said and did. He picked up the petticoat and walked
out of the changing room. The two women were deep in conversation as he
walked into the store. Jane looked towards him.
"This is Susan and she needs someone to tidy up the shop. So, every week
day after you finish at work you're going to come here and help out for
an hour. Understood?"
"Yes Jane," he replied.
"Now say thank you to Susan for your pretty petticoat."
He thanked Susan and the two of them left the shop, the petticoat in a
large bag. Once back at the office he was sent back to his room and told
to get on with his work. He sat behind his desk for quite a while lost
in thought. Things seemed to be spiralling out of control and, what had
once been a small, private arrangement between him and Deborah had now
turned into something quite different. It was also clear that if Deborah
and Jane weren't working together on this, then at the very least they
were talking about it to each other. How else would Jane know about the
pink taffeta dress?
He looked at the large bag in the corner of his office containing the
starched tulle petticoat. If he was being honest he would have to admit
that a part of him was excited to see how it would look under his pink
dress. Was he losing his mind or was he simply losing something much
simpler - control?
He struggled to concentrate for the rest of the day and he was relieved
when the clock said 5pm and he could leave. He hadn't heard from Deborah
today so he didn't have to rush to go around to her house. When he got
home he was surprised to find a small package taped to the front door.
He took the package inside and opened the packet. Inside the package
were a typed note from Deborah and a small bag bearing the name of a
local lingerie store.
He opened the bag to find that it contained a baby-doll nightie in a
pale baby blue colour. The nightie dripped with delicate layers of lace
ruffles. There was also a matching pair of little panties also covered
in lace frills. He read the note.
"This is your new night dress and you are to sleep in this every night
without fail. I have talked to Jane who has told me about your new
petticoat which you will now wear under your pink dress. This evening I
want you to try on the night dress and take a picture of yourself in the
nightie and send the picture to me. I also want you to take another
picture of yourself wearing your frilly pink lingerie, stockings and
your new petticoat and also send that to me. Also don't forget to keep
practising wearing your high heels."
He made himself a drink and then slipped out of his male top clothes. He
took his high heels out of the closet and slipped his feet into them.
After unwrapping the new petticoat he stepped into it again and pulled
it up to his waist. He spent several minutes fussing over all the
starched layers of tulle to make sure that it stood to its fullest
possible extent. He then stood in front of the full-length mirror on the
wardrobe door and took a picture of himself on his mobile phone. In fact
he took several different views of himself to make sure that the full
effect was captured.
He then undressed completely and slipped into the baby-doll nightie and
pulled the little matching knickers up his hairless legs. The material
was so soft against his skin and it made only the slightest of rustling
noises as he moved. He stood in front of the mirror again. The nightie
was cut very short and only just about covered the little panties.
Although he noticed that the material was so light that any movement and
the nightie floated up slightly exposing his matching panties. He took
his mobile phone and again took several pictures.
Following his instructions he sent all of the pictures in an e-mail to
Deborah. Once they had gone he suddenly had second thoughts. What was
she going to do with the pictures?
Step 10
The following morning David almost slept through his alarm clock. His
legs and feet ached from another long evening practicing in his high
heels. He pulled back the duvet and climbed slowly out of his bed. He
walked to the bathroom in his baby-doll nightie. He went through his
normal morning routine and was out of the door only slightly later than
normal. He walked to work still feeling surprised by the constant pull
of the suspenders with every step that he took. His normal shoes also
now felt slightly strange after another evening spent walking around in
3 inch heels.
When he arrived at his office there was note on his desk telling him to
report to Jane as soon as he was in. He made his way towards her office,
a strange feeling in the pit of his stomach as he had no idea what he
might be walking into. He knocked on her door and entered. She was sat
at her desk looking intently at the screen of her laptop.
"I must say you do look really cute in your new nightie."
He froze. Deborah must have sent the pictures he had taken to Jane. If
she had sent them to her, then who else had they been sent to?
"I've been thinking about your work clothes and I really don't think
that what you have on is suitable anymore."
She reached down for a bag on the floor.
"These will be much better and you're to wear them from now on."
He took the bag and moved to leave the room.
"Where do you think you're going? Put them on," she said.
David opened the bag and, to his relief, found a pair of trouser and a
shirt. But when he looked closer he was less reassured. He took off his
own male clothes, acutely aware that Jane was watching him intently,
revealing once more his frilly lingerie and stockings. He noticed she
smiled when his frilly underwear was open to her gaze. He picked up the
trousers and noticed the label of a well-known woman's clothing store.
He stepped into the trousers and pulled them up. They were plain black
and a hipster design that sat on his hips rather than around his waist.
They also clung tightly to his bottom and to his thighs, and ended with
a flared hem at his shoes.
The shirt was plain white, but made of silk rather than his usual
cotton. He also noticed that it buttoned up the opposite way that he was
used to on his own shirts. It had a much smaller collar with rounded
tips and the sleeves were quite full but ended in a tight cuff at his
wrists.
Jane stood up and walked over to him for a closer inspection. She ran a
firm hand over his bottom feeling how the trousers clung tightly. She
ran her fingers over the silk sleeves of the blouse - it really wasn't a
shirt.
"That's much better - don't you think so too?" she asked.
He nodded glumly. He really wanted to say no but he was sure that if he
did it would be another beating with the ruler, or perhaps even
something worse.
"Now run along and get on with your work."
David walked self-consciously back to his office feeling as if all the
eyes of his work colleagues were upon him. He wasn't keen at all at the
way the full sleeves of the shirt moved as he moved almost billowing
around his arms. He especially didn't like the way in which these
trousers clung so tightly to his body. At least he could wear his jacket
over the shirt, and it then also hid the pink straps of the bra which
showed through the silk of the blouse.
When the time finally moved around to 5pm he was glad to leave work as
he was keen to change out of these new clothes. Then he remembered that
he was due at Wendy's clothing store in the shopping centre to tidy and
clean. He walked quickly to the shop as he didn't want Wendy telling
Jane that he had been late on his first day working in the shop. The
sign on the door said closed when he got there so he had to knock on the
glass. He waited a few moments until a smiling Jane appeared to unlock
the door and let him inside.
"Hello sissy," she greeted him, "are those clothes knew? Take off your
jacket and show me."
He took off his jacket and stood before her in his tight-fitting hipster
trousers and his silk blouse. She indicated for him to turn around and
he pirouetted slowly so Wendy could get a proper look at his new work
clothes.
"They're lovely aren't they but you don't want to ruin them do you.
Strip down to your frilly underwear while I find something for you to
wear."
He took off the trousers and the blouse and stood embarrassed in his
lingerie and stockings for Wendy to return. She came back into the shop
carrying a dress.
"I've had this in the shop for absolutely ages and I really don't think
anyone's ever going to buy it so you may as well wear it."
The dress was made of a blue and white checked gingham material and he
stepped into it and Wendy did up the zip. It had short puffed sleeves
and an elasticated neckline. The bodice of the dress was quite plain but
fitted tightly around his body. The skirt was micro mini length and
flared in design so that if he moved it swirled around his upper thighs.
"You look really cute," she laughed, "Now I want you to hoover the
carpet and polish all the counters."
He took the vacuum from behind the counter where Wendy indicated it was
and he set to work. As he moved up and down the store he could feel the
little skirt lifting slightly. It didn't take him long to hoover the
small shop and then he set to work with a cloth and some polish. As he
was polishing he felt his skirt being lifted and he glanced over his
shoulder to see Wendy standing behind him.
"Don't let me distract you, you carry on working," she said.
He then felt her hand stroking over the frills on the back of his little
knickers. Then she started to slowly pull the knickers down to his
panties.
"Lean over the counter sissy," she instructed.
David stopped polishing and bent forward across the wooden top of the
counter. To his shock he then felt the cheeks of his bottom being slowly
pulled apart.
"Please stop," he begged.
"Just relax sissy," she hissed.
Something cold and hard was now pushed against and then between his
cheeks. He winced and tensed as he felt it now beginning to enter his
virgin bottom.
"Try to relax little sissy, it's always painful the first time and the
more you try and stop it the more it will hurt."
He tried to relax but a single tear emerged and started to run down his
cheek.........
......he walked home gingerly, a strange sensation down there. His mind was
a confused mix of feelings and emotions after what had just happened in
the shop with Wendy. It had seemed to take a long time and at times he
had thought she would never stop. It was if not only had she taken his
virginity, she had also taken his maleness at the same time. Could he
ever be the same person again?
Haven
- 11.03.2021
- 7
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