Sissy Stepson 10 Stepmother s Sissy
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One Step At A Time (Part 4) free porn video
One step at a time
Step 8
David arrived at his office and headed swiftly to the toilets to check
on his appearance in the mirror. The colour of his hair was definitely
more than a couple of shades lighter and he was not sure how he would
answer the inevitable questions he was going to get. The cut was
actually quite subtle but one was left in no doubt that it was a
feminine style. Unlike the typical harsh edges of a traditional man's
haircut, Sandra had softened the edges by cutting into the hair and the
back had been shaped into a sort of soft wedge shape. It had been left
uncut at the crown but then graduated quite sharply down to his nape. He
tried wetting his hair and smoothing it flat but it had little effect,
with a resigned he walked out of the toilet and to his small office. He
kept his eyes fixed on the floor in the hope that people wouldn't notice
him passing by.
Once safely inside his office he slipped off his jacket and hung it on
the back of the door as usual. He went over to his desk and began to
flick through the mail that had been left in his in-tray. His
concentration was broken by a knock on his door.
"Come in," he said.
He looked up to see Jane from the office down the corridor standing in
front of his desk. She was the supervisor of the whole floor and several
rungs above him on the corporate ladder. She was also at least 10 years
younger than he was but was well-known within the organisation for being
something of a high-flyer. As usual she was dressed in her designer
power suit - neatly tailored jacket and a straight skirt that fell a
couple of inches above her knees. Her hair and make-up were always
immaculate making her look as if she had just stepped straight out of a
salon.
"These are the papers that I want you to look over," she said.
"Thank you," David replied.
To his surprise he noticed that having placed the papers on his desk she
remained standing there looking at him.
"Was there something else?" he asked.
"Did you change your hair colour?" she enquired. "It looks very, er,
pretty".
David blushed and mumbled a thank you. Jane then stepped forward and
leaned closer to him and said in a quiet voice, "Are you wearing a bra?"
He froze in horror. He had forgotten that the pink frilly bra straps
could be seen through his work shirt. He rushed to think of a response
that might be even vaguely believable. He went to speak but Jane cut him
off.
"I think you and I need to have a private chat - don't you?"
She turned and walked to his office door with a strange look on her
face.
"My office, 2 minutes, understood?"
He nodded. He tidied up his desk and walked slowly down the corridor to
the large corner office that Jane occupied. He knocked quietly on the
door and entered. This was only the second time that he had been in her
office and he was impressed again by the quality of her office
furniture. Jane walked past him, locked the door to her office, and
then walked to the windows and closed the blinds.
"So David, are you wearing a bra? Tell the truth now."
"Yes," he mumbled.
"Show me," she commanded.
He paused for a moment but the harsh expression on her face made him
realise that she was serious. He slowly unbuttoned his shirt and folded
it over the edge of the desk. She walked over to him to take a closer
look. She ran a finger over the shoulder straps.
"Well this is very pretty isn't it and so cute and girly," she laughed.
He kept his eyes fixed on the floor, mortified that his sissy status had
now been witnessed by someone else.
"Are those suspender straps I see showing through your trousers?"
He nodded.
"Show me," she instructed.
David paused and then with a shrug of resignation took of his shoes and
then removed his trousers to reveal his pink frilly satin suspender
belt, pink stockings and finally his little pink frilly knickers.
Jane clapped her hands together in enjoyment. "My oh my, aren't you the
prettiest little thing," she giggled. "Turn around".
He slowly turned around hanging his head in shame at this public display
he was being forced to give. He jerked his head up suddenly when the
flash of a camera went off. Jane was holding her mobile phone and taking
pictures of him in his frilly underwear.
"Good boy, now you may get dressed."
David hurriedly dressed back in his male clothes to hide his frilly pink
lingerie and desperate to be out of this office.
"Sit down and let me have a proper look at your new hair."
He sat in the chair as Jane walked over.
"I love this colour on you and the cut is also nice, much more you, much
more feminine".
She ran her fingers through his hair and he tried not to flinch.
"Now run along back to your office," she told him. "But I want you back
here at 4pm to clean and tidy my office."
David left her office and scurried back to his room. Once back inside he
slipped his jacket back on to make sure that no one else would become
aware of his secret. It concerned him that what had once been a very
private arrangement between himself and Deborah was now known to 2 more
people - Sandra and now Jane. He was also worried about the possible
implications of Jane knowing about this as she was, after all, his line
manager.
Back in Jane's office she was dialling a phone number.
"Hi Deborah, you were right he's a little treasure isn't he? The hair? I
think it's lovely but you need maybe to take him even lighter in colour
next time. He's cleaning my office later so I can see how well he obeys
instructions. Will do, speak soon."
David struggled to concentrate for the rest of the day as he tried to
come to terms with the idea that more people were now aware of what he
was becoming. It had also taken a nastier turn with the inclusion of
Jane into the equation. If she told him to do something surely he had no
choice now. He glanced at his wall clock and saw that it was nearly 4pm
so he shut down his computer, locked his office and made his way back to
Jane's office.
He knocked on the door and walked into the smart office. Jane was sat
behind her imposing oak desk talking to someone on her desk phone. She
pointed towards the bottom drawer of a filing cabinet in the corner and
indicated for him to open the drawer. In the drawer he found a number of
cleaning items - furniture polish, cloths, and a small hand-held hoover.
She finished her phone call and turned towards him.
"I see your punctual - I like that. Now strip down to your frilly
underwear."
He undressed quickly, folding his jacket, shirt and trousers over the
back of the chair in front of her desk.
"We need to protect your delicate lingerie really though. One moment."
She left the room and returned shortly carrying a pink nylon overall.
"This belong to one of the cleaning staff, put it on," she told him.
David took the nylon overall and buttoned it over his underwear. It was
quite short in length and came down to his stocking tops.
"That will do until we can find you something more suitable now get on
with the cleaning and make sure you do a good job or there will be a
punishment," she warned him.
He took the small hoover from the drawer and began to clean thoroughly
around the office. He noticed that Jane was watching his every move. As
he worked he could feel the suspender straps pulling on his stockings.
When he stretched up to hoover higher shelves the shoulders of the bra
pulled on his shoulders. After hovering thoroughly he switched off the
cleaner and took the polish and a cloth. He was careful to make sure
that he didn't miss anywhere as he was sure that she was assessing his
handiwork. He also wanted to make sure that avoided any sort of
punishment that she had mentioned.
After 40 minutes of work he felt satisfied that he had cleaned
everywhere and that she would be happy with his work. He returned all
the cleaning materials back to the cabinet drawer and stood before Jane.
"Actually that's not a bad job of cleaning my office for a first try. So
I'll expect you to do this once a week - understood?"
David nodded realising that really he had no choice but to say yes.
"Unfortunately however you seem to have caused a run in one of your
stockings," she said pointing at his left leg.
He looked down and saw the run in the back of his left stocking.
"You need to learn to be more careful I think and the only way you're
going to do that is if you receive a proper punishment."
Jane stood up and walked around her desk. She moved the chair on his
side away from the desk.
"Lie across the chair face down," she said with a harsh edge to her
voice.
He had a horrible feeling about what was to happen next but he could see
no other choice. He lay down across the seat of the chair and waited. He
felt the edge of the pink overall he was wearing being lifted. Then he
felt her fingers slide into the waist band of his little knickers and
they were slid down to his knees. She gently stroked his cheeks.
"Shaved, I like that," she commented.
Jane reached into her desk drawer and took out a 12 inch wooden ruler.
She slapped it firmly against the palm of her hand. David flinched as he
heard the noise of each blow.
"As this is your first transgression I will be lenient and you will only
receive 15 strokes."
He tensed in preparation for the first blow of the ruler. For some
reason he had thought, or rather hoped, that this would be quite a
playful spanking with the ruler. But when the ruler hit his bare cheeks
he felt a searing pain. Almost immediately it was followed by another
blow and then another. He bit his bottom lip hard as he tried not to cry
out and so give Jane the satisfaction of knowing that she had hurt him.
By the time the beating endured had been completed he had not cried out
but tears were falling.
She placed the ruler on her desk and then pulled his little knickers
back up over his burning flesh and lowered the overall.
"Stand up," she said brusquely.
Somewhat unsteadily David stood and wiped the tears from his face with
the back of his hand. He could feel the heat from the blows inflicted by
the ruler.
"Now get dressed and I'll see you tomorrow."
David hurried down the corridor eager to get away and out of the
clutches of his new tormentor. Things had been bad enough when he had
been solely at the mercy of Deborah, but now things were starting to get
out of hand. He rushed back to his home as he had to make sure that he
would at Deborah's house at exactly 8pm as he had been instructed.
When he got home he found a parcel had been left outside his front door.
He took the package indoors and opened it. Inside he found the sets of
frilly pink lingerie that he had been told to order. At least he
wouldn't have to keep wearing the same underwear over and over he
thought to himself.
In his bathroom he inspected the damage inflicted by Sandra. A series of
vivid red stripes still remained across his bottom and he couldn't help
worrying if they would turn to bruises. He also couldn't help thinking
if that was to be only the first of many such encounters with the ruler.
At least Deborah didn't believe in physical punishments like that,
although the changes to his hair had certainly caused a number of raised
eyebrows around his office building. Seeing the time he quickly adjusted
his clothing and made his way round to her house.
Deborah let him into the house and pointed towards the living room. He
walked into the room and saw a pair of shoes on the floor. They were
made of pink patent leather with what he guessed to be a 3 inch heel.
She followed behind him into the room and picked up the shoes.
"These are for you. Go upstairs and put your dress on and these shoes
and then come back down here."
He took the shoes and walked up the staircase. In the usual room he
removed his outer male clothing and took the pink taffeta dress from its
place in the wardrobe. He stepped into the dress and zipped up the back
of it. He then stepped into the pink shoes and tried to stand and walk.
He had never worn heels before and he struggled with the unaccustomed
change in his posture brought about by wearing heels. It felt at every
step as if he was about to topple over. He stood before the mirror and
fluffed out the abbreviated skirt so that it sat right. He also noticed
how the dress fit better, and indeed looked better if he was honest,
when he wore it with a bra underneath. He started to walk back
downstairs, clinging on to the banister as he descended the stairs.
He tottered into the living room and Deborah looked up as he entered.
"Walk around a bit so I can see how you cope in heels," she told him.
He tried to walk steadily as he paraded in front of her.
"You're definitely going to have to practice in those. Take them home
with you and whenever you're at home I want you to wear the heels and
walk around".
He went to leave the room but she stopped him with a wave of her hand.
"I think you have something to show me before you go."
David looked puzzled as he was unsure exactly what she meant.
She stood up and indicated for him to walk over to her. She lifted the
little skirt and pulled his frilly knickers down to his knees.
"I must say Jane is pretty accurate with her ruler isn't she," she said
laughing. "And they certainly look as if those must have stung."
David suddenly realised that this could only mean one thing. Deborah and
Jane knew each other. Was this all a plan between the two of them?
Haven
- 29.03.2022
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