Sissy Stepson 10 Stepmother s Sissy
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One Step At A Time (Part 1) free porn video
One step at a time
Step 1
David had been living in the same apartment block for about 14 years and
usually tended to keep himself to himself most of the time. It's not
that he was rude, far from it, but he had been a shy person for as long
as he could remember. He was an only child and his late father had
passed away when he was very young, so much so that he now struggled to
remember much about him at all. His childhood had therefore been
dominated by his mother. He remained living her with her for many years
and if it had not been for her death when he was 30 he would probably
still be living with her now. After the funeral he remained in the house
and ten years later had still not had the heart to throw out her
clothes.
His mother had always been very well groomed and took great pride in her
appearance at all times. She had also always been a very feminine figure
and he couldn't remember ever having seen her in a trousers or even
jeans. Every image her had of her was that of wearing a tailored skirt
or a flowing dress, usually made of satin or silk. Growing up he had
become accustomed to the feminine floral smell of the house and the pale
pastel colours that dominated the d?cor. Even his own room had been
painted a delicate shade of peach complete with frilled curtains at the
window. The house was now his but he had been reluctant to change the
feminine feel of the place.
He turned the key in the front door and stepped into the house - now his
house. He hung his coat tidily on the hook, as he had been brought up to
do, changed his outdoor shoes for a pair of indoor slippers and walked
through into the kitchen. He turned on the oven to heat the casserole he
had prepared the night before and poured himself a glass of wine. The
ring of the doorbell disturbed his thoughts and he retraced his steps.
Opening the door he was confronted by a stranger, a woman that he hadn't
seen before.
"Can I help you?" he asked.
The woman was probably about 10 years younger than he was, around 21 or
22 he guessed. She was probably a clear three inches taller than he was
and with a somewhat fuller figure. Not fat, as that would be unfair, but
certainly more substantial than he was although she carried it very
well. Her shoulder length blonde hair was immaculately styled and was
clearly the work of someone skilled in the art of hairdressing.
Similarly her make-up had also been applied by someone who knew what
they were doing around cosmetics. The subtle shading and brush work
served to accentuate her facial features so for a moment one wanted to
simply pause and admire the finished result.
"I've just moved in next door and I was wondering if I could borrow
maybe some bread or something as I have no food in?"
David paused before answering as he had never been that comfortable in
the company of women, except for his mother.
"Do you want to come in and I'll see what I can do," he muttered
quietly, "The kitchen is straight ahead".
As she walked past him and towards the kitchen he was able to take in
her clothes. For a young woman she had an immaculate taste in clothes.
The scarlet silk blouse fitted her young body perfectly and worked well
with the jet black leather skirt that she wore. From the hem of the
skirt emerged a well-shaped pair of legs encased in what looked like
sheer black stockings. On her feet was a pair of black leather shoes
with what looked like a three inch heel, the leather polished to a high
sheen.
"Hmm, that smells lovely," she remarked on entering his kitchen.
"Thank you," he replied hesitatingl. "There's actually enough for two if
you don't mind just a simple beef casserole".
He was surprised at his response as normally he would have been too
self-conscious to have made such an offer to a stranger. But something
about her just made him want to know more and prolong the encounter.
"That would be great," she replied. "And my name's Deborah".
The next hour or so had flown by as David found himself thoroughly
enjoying the company of this enchanting young woman. It turned out that
she worked as a beautician and had moved to the area after a disastrous
marriage that, in her words, should just never have happened. She
complimented him on the decor of the house and how neat and tidy
everything seemed to be.
"I could do with someone like you to look after my place," she said
after the meal, a strange smile playing across her lips.
After the two of them had cleaned up everything after the meal they sat
down in the front room with a glass of wine each. David noticed that as
they talked she kept glancing down at his hands.
"Is something wrong with my hands?" he asked.
"Sorry, professional interest, I was just thinking that a quick manicure
would make your nails look so much better," Deborah said.
"A manicure?" he replied, somewhat confused.
She laughed. "Don't panic I have a lot of male clients, I'll be back in
a minute".
Deborah left the room and he heard the front door open. He sat there
somewhat at a loss to know exactly what was going on. At the same time
something the idea of someone doing his nails he found strangely
appealing, although he wasn't sure he could explain why. He heard the
front door and then Deborah reappeared in the room, carrying a small
case. She sat down next to him and opened the case which contained
numerous small drawers and compartments.
"Don't look so nervous," she laughed.
He sat watching intently as she worked on his nails - cleaning them,
filing and shaping them. He felt a strange mix of emotions, part of his
brain telling him that somehow this was wrong, but at the same time it
also felt somehow right. After several minutes careful work by Deborah
he was left with two well-manicured hands, not feminine so much as
looked after. To his surprise she then took a small bottle of pink nail
varnish from out of the bag.
"Nail varnish?" he asked.
"It's just a bit of fun," she reassured him.
He sat nervously as she carefully painted each of his finger nails with
a thick, pink coating of varnish. Once the polish had dried he was
surprised at the effect of the simple act of applying the varnish had on
his hands. They definitely looked more feminine almost as if they were
now someone else's hands.
"There you go, isn't that much better?"
He had to admit that part of him did actually like the finished result.
"Sorry, I have an early start tomorrow. It's been nice to meet you and
thanks for the food." And with that she stood and headed for his front
door.
After seeing her out he returned to the front room to clear up and saw
she had left the bottle of nail varnish on the small table. As he
cleared away the now empty wine glasses he wasn't sure what to do with
the varnish. Feeling it would be rude to just throw it away he put it on
a shelf in his bathroom.
Next door Deborah sat down in her own front room with a smile on her
face. She had had no idea that things would turn out this well but it
was looking as if she had found her next maid. The nail varnish had been
a simple test and she had been expecting more protests from David. But
she knew from experience that she had to take things slowly as she
didn't want to scare him off.
Step 2
Deborah left it a couple of days before popping around to see David
again. She wanted to give him time to think about the manicure and the
nail polish and she was also intrigued to see if he had removed the
polish. She checked her appearance in the hall mirror before leaving.
Having done all her reading around this topic she knew what "men" like
him would want. As usual her hair and make-up were done to perfection,
including a fresh coat of deep red varnish on her long finger nails. The
leather skirt, stiletto heels, silk blouse - it all helped.
She knocked firmly on the door of his house and waited. After a moment
the door was opened and he stood there with a surprised look on his
face.
"Oh hi, would you like to come in?"
She walked into the house, the tip tap of her heels echoing on the
wooden floor.
"Coffee?" he asked, pointing towards the kitchen.
She nodded and followed him into the compact kitchen. David busied
himself making her a drink. As he got the drinks ready Deborah watched
carefully, in particular looking to see what state his nails were in.
she was pleasantly surprised to see that not only were his nails still
varnished, the varnish was immaculate.
"I see you kept the nail polish," she remarked.
He blushed and almost tried to hide his hands.
"I didn't have any polish remover and the colour isn't that noticeable
really," he stammered.
"It looks almost new," she said.
"Well, erm, it was starting to get a little chipped and as I couldn't
remove it so it was easier to apply a fresh coat," he explained
hesitantly.
Deborah smiled contentedly to herself - step two had gone well. Without
having to tell him to he had understood that he was now expected to wear
nail polish all of the time. The subtle tactic of leaving the bottle of
varnish on the table when she left two days ago had sent out the clear
message without anything needing to be said.
The coffee was made and he placed a steaming cup in front of her and
then sat in the chair opposite. Deborah looked intently into his eyes.
"Is there something wrong?" he asked.
"I was just looking at your eyebrows. They could do with a little
tidying up - would you like me to do that for you?"
She kept her tone of voice light. Now was not the time for the harsh
tone she would normally use with one of her "boys". She retrieved the
small tweezers from the side pocket in her skirt and rose from her
chair. Walking towards David she was not surprised to see that he didn't
flinch away or protest at her suggestion.
"Tilt your head back and then hold still," she spoke softly.
With a skilled hand and a practised eye she began to groom and trim his
eyebrows. At this stage it was a case of less is more. He was not ready
for the very thin and high-arched brows that were to be his ultimate
destiny. For now it was enough to simply thin out his brows and create a
more defined shape. David winced as the hairs were plucked from his
brows but he was more concerned with what exactly she was doing and what
the finished result would look like.
After about twenty minutes of careful work she stepped back to appraise
the result of her handiwork. While they now clearly looked quite heavily
groomed they were still the right side of masculine - just.
With some trepidation he looked in the mirror to view the finished work
of the tweezers. Although it was quite a significant difference he had
to admit that his brows did look better than before. Deborah stood
behind him watching with interest as he preened in front of the mirror.
She smiled as he stroked a manicured and polished finger nail across his
newly plucked brows. This might be even easier than she originally
thought.
They sat and chatted for half an hour or so. Except it wasn't chat for
Deborah. Her questions and comments were carefully thought out to probe
his thoughts and plant thoughts and ideas into his mind. Putting forward
what seemed as quite vague suggestions, but which in reality were small
tests to gauge how he reacted to them. She was pleased to see that none
of her suggestions met with anything even remotely close to a negative
response.
"I have to go but I'll be in touch soon," she said and left the house.
David sat deep in thought after she had gone. He looked down at the pink
nail polish he had been wearing for the last couple of days now. He had
been self-conscious leaving the house for the first time with his pink
nails but, to his surprise, no one had commented on it. Even people that
he worked with seemed somehow oblivious to the change, or at least
didn't say anything to his face. He looked in the mirror again at his
newly-shaped eyebrows. This was a much more noticeable change and he
couldn't help wondering if this alteration might get more of a response
from people. Yet at the same time he couldn't protest as Deborah had
worked on him. There was something about her that seemed to melt even
the slightest hint of resistance within him. It was almost as if giving
up control was a release for him - it took away the personal
responsibility and so in a way it was strangely liberating. Ultimately
there was nothing wrong in these changes anyway - was there?
Step 3
Two days later and David received a phone call from Deborah.
"Can you pop round this evening I need your help with something. Around
8pm?"
"Of course, I'll be there," he replied.
On the other end of the line Deborah smiled to herself - sometimes this
was almost too easy. But, she still needed to tread carefully; a move
too fast too soon and he might bolt like a frightened rabbit. This
evening was a very important next step as she had to see his reaction to
female clothing, or more importantly his reaction to the very idea of
him wearing female clothing. It was a well-used approach which she had
read many times, although in truth it had usually been in the context of
cross-dressing fantasies.
Later that day David approached the front door of her house. Before he
knocked he glanced down at his nails to check the varnish was up to
standard. He knew that she had high grooming standards and he wanted to
make sure that he measured up. It was important to him that he made the
right impression. He took a deep breath and knocked on the door.
Deborah swung open the door and indicated for him to enter.
"I need you upstairs so straight ahead and turn to your right at the
top," she instructed.
He dutifully climbed the stairs and turned as instructed to find himself
entering a large, open room. In the middle of the room was a sewing
machine and various bits and pieces connected with dressmaking.
"I'm working on a dress and I need your help while I make the final
adjustments to ensure a good fit," she informed him.
"I don't really know anything about making clothes or even sewing so I'm
not really sure how I can help," he replied.
Deborah walked over to a wardrobe in the corner of the room and took out
a dress on a clothes hanger. It was made from pink taffeta which rustled
as she brought it out of the wardrobe.
"This is the dress I have been working on and now I just need to make
the final adjustments. I can only do that if someone is wearing the
dress, so......" And she looked straight at him.
"You mean you want me to wear it?" he asked in surprise.
"It would be a huge help and no one's looking so what's the problem?"
she asked.
He paused for a moment trying to take on board what had just been sprung
on him. He looked at the dress. It was certainly a nice looking garment
and a very small part of him was actually intrigued to know what it
would feel like to wear. He also really liked Deborah and so he was keen
to help her out if he could. But, wear a dress?
Kaidence
- 02.02.2021
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