Hero
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Hero In Heels Part One free porn video
Hero in Heels
Part 1: New beginnings
Charles was an ex-cop who specialised in electronic fraud detection,
medium height and build with the classic crewcut and goatee look; he
liked to dress well with a preference for tailored suits. Dorothy, a
petite redhead, was a marketing manager for a telecommunications company
and has developed a good eye for the stylish professional look. They met
when he was 'following the money' as part of an investigation, and
immediately hit it off.
They had both worked in their fields for over fifteen years and were
feeling the itch to try something new. Over a long dinner one evening
they decided that it was now or never if they both wanted to prove their
business ideas. Charles was convinced that the expansion of block-chain
and crypto-currencies was a huge opportunity, and people who got in on
the ground floor would be very successful. Dorothy on the other had
wanted to indulge her fascination with fashion, especially vintage and
designer clothes by opening a specialist boutique.
They toasted, with very expensive Champagne, to new beginnings well
aware that such extravagances were going to be rare for fresh
entrepreneurs. The following day they resigned their positions and
stepped into the unknown.
They felt they both needed premises, Dorothy certainly, but Charles also
took a small serviced office in the city as he didn't like the idea of
working from home; even though most of his clients are online. In
addition, he had continued a semi-formal arrangement with a young
freelance programmer, Mark, whom he had worked with on some more
technical cases and intended to use now when clients needed more than
simple advice.
Dorothy found a retail space ten minutes' walk from their apartment
block. She wanted a convenient location as her market research suggested
she may have to open late at least once a week for the convenience of
her customers. She settled on Thursday evenings as this seemed the most
likely to attract women looking for something new to wear at the
weekend.
Everything was going well for the first few months, especially for
Dorothy. Word of mouth got around and she began to build up a consistent
customer base, with the Thursday evening sessions proving especially
popular. The first real trouble was when she decided to open late on
Tuesdays to see if this would prove equally popular.
Tuesday evenings were very quiet at first, and the third week Dorothy
was relieved to hear the sound of the shop door opening. She went out
but was a little confused to find the new customer was a young man in a
hoodie and jeans. She greeted him as she would any other customer, but
with a prickling of unease. He glanced around the empty shop, and then
pulled a knife and demanded all the cash from the till and her mobile
phone. When she hesitated, he advanced and held the knife to her throat.
With a rush of common sense, she quickly handed over everything he
demanded. He then pushed her up against the wall and warned her not to
tell anyone as he knew where he could find her. When he left she rushed
to lock the shop door then broke down and cried. That was how Charles
found an hour later her when he discovered she wasn't answering her
phone.
He wanted her to go to the police, but she refused due to the threats
she had received. After that he tried to insist that she gave up the
late openings, but she insisted that they were so popular the business
wouldn't be profitable without them. Finally, he acquiesced but, on the
condition, that he would work from the glass fronted shop office on
those evenings, so she wouldn't have the chance of being alone again.
Dorothy agreed to Charles' demand, although she secretly had
reservations about the presence of a man in a very feminine environment.
It might put off her customers as they wouldn't be so relaxed about the
shopping experience.
Part 2: A problem and a solution
On Thursday Charles came back early from his city office and set up his
laptop in the office. His business primarily consisted of giving advice
in text chat sessions or via skype voice calls. Occasionally he would
have a video call if the clients wanted to see who was advising them on
their investments. To him it seemed there was brisk business in the
shop, as he heard a lot of activity with customer coming and going as he
focussed on communicating with several of his own clients throughout the
evening. The time flew by, and he was a little surprised when Dorothy
turned off the main shop lights and came through to the office.
He asked Dorothy how the evening went, commenting that it seemed very
busy. She was non-committal, not wanting to seem ungrateful for his
presence, but she felt that although there were as many customers, they
hadn't stayed as long, and had spent much less money. Realising that
something was wrong he probed until he finally got to the bottom of her
concerns. It seemed that they were at an impasse but agreed to spend the
weekend coming up with a way forward.
On Saturday evening they went out to dinner and talked about ideas that
might satisfy them both, and as the wine flowed they came up with more
schemes that they joked about. One of the funniest, at least for
Charles, was that he put on a wig and lipstick, so he would fit in
better in the feminine environment. He joked that his beard might
detract from the look a little. Dorothy agreed, but ended with a
thoughtful expression on her face.
Sunday morning began with slight hangovers and pottering about making
breakfast in the apartment. Charles was putting on the coffee when
Dorothy walked in with something behind her back.
"Charles, could we just try something please?"
"Anything. What's up?"
She produced a red-blond bob wig and said, "Do you remember this from
the time I had that short hair cut that I hated a couple of years ago?"
"Yeeessss," he responded suspiciously.
"I was thinking about our idea last night, and I was wondering if we
could just see what you would look like." He voice was tentative, but
desperately hopeful.
Charles didn't want to upset her, so put forward the most tactful
objection he could think of.
"Dot, I'll do this if you really want, but don't you think your
customers would be even more put off having a drag queen sitting in the
office?," he asked with a lopsided smile.
A small frown creased her forehead. ?Well actually no, I don?t think so.
Most women are far more comfortable around gay men when they want to
relax and just be themselves. I also don?t think you would look like a
drag queen, at least if you agree to shave your beard off of course.?
?Alright, alright. Just to prove you wrong. I?ve been wondering what I
look like under this these days I suppose. But let?s have breakfast
first,? he suggested, searching for any pretext to delay what was
looking increasing like the inevitable.
Half an hour later Charles was looking at his reflection in the bathroom
mirror. He stroked his bears one last time before slowly pealing it off
with his electric clippers. As the hair fell away a new face revealed
itself to him; one he hadn?t seen for over fifteen years. He also
realised how much weight he had lost since leaving the force. Running
their own businesses had not only kept them busy, but also forced them
to economise with less eating out and fast food. Charles was also no
longer experiencing the doughnut heavy environment of a station house.
The outcome of all this was that he apparently had cheekbones now.
He wanted to do a good job for Dorothy now that he was committed, so he
first had a hot shower to open his pores then proceeded to a wet shave
with two passes, the first to clear the main stubble, then a second
against the grain everywhere with careful searching by his fingers to
ensure perfect smoothness. Finally, realising his eyebrows were getting
very bushy, ran the clippers over them to bring the unruly caterpillars
back into line.
He gave the mirror a firm polish with the hand towel and stared at his
fresh new face. He was hairless except for his eyebrows, and his weight
loss seemed to have firmed up his features. His dark brown eyes looked
back at him from above definite cheekbones, and he stroked his hand over
a newly sensitive chin. He had grown the beard to accentuate it as with
gaining weight he felt it had been receding and making him look softer.
Now he was slimmer that seemed to have been reversed, and he looked
younger than he had in years.
Throwing on his robe he headed out to see Dorothy.
?Wow!?
Dorothy had a brilliant smile. She rushed over to him and ran her hands
over his fact. ?So smooth and so handsome. Why didn?t we do this years
ago?? She pulled him into a long deep kiss, he bountiful auburn hair
caressing his hyper-sensitive cheeks. She was still wearing her robe as
well, and his hand slid inside to cup her breast and caress her rock-
hard nipples. He gently lowered her to the carpeted floor and slipped
inside her. He legs wrapped around him with a desperate urgency and she
climaxed almost immediately. She kissed him hungrily and soon there was
a second climax, this time for both of them.
They lay on the living room floor catching their breath to recover from
the suddenness and intensity of their love making. Then giggling like
teenagers, they got up and made their way back to the shower were they
lovingly soaped each other down, caressing their bodies with more
attention than they had in a long while. It seemed the break from
routine was very good for them both.
Part 3: Another beginning
Once again, they were sitting in the living room in their robes, still
basking in the afterglow of the best sexual encounter in many months.
Dorothy held up the wig and asked if Charles was ready to go ahead. To
him now it seemed like a bit of silly fun, so he gave her the go ahead.
She stood up and walked around behind and his sight was suddenly partly
obscured by the blond hair. ?Hold the front just their please,? she
asked. He did so feeling a strong tug as the cap slipped snugly over his
shaven crown.
It felt very strange. He could feel it brushing against his shoulders
and the back of his neck and covering his ears. The fringe brushed his
forehead when she told him to release his hold, and he waited patiently
while she brushed and fussed out of his line of sight. Finally, she
moved around in front of him and caught he breath in a slight hitch.
?What? What?s up?? he asked suddenly concerned.
?Nothing. Just wait a moment. Don?t move and she hurried off to the
bedroom, while he waited with increasing concern.
When she returned she held up a tube and with a twist revealed a dark
pink lipstick. She looked at him questioningly. ?Please?? she pleaded.
He shrugged his shoulder, feeling the weight of the hair. ?In for a
penny ? why not.?
Dorothy grinned, and moved close to his face.
?Open your mouth. Now purse your lips.?
He felt the alien sensation of the lipstick being smoothed on, and to
his surprise he could also smell it quite intensely. She folded a tissue
and said, ?Open. Now press down.?
She sat back and closed the lipstick while gazing at him.
?Want to see??
?Um, I suppose so,? he replied. Now quite disconcerted by her behaviour.
She stood up, held out her hand so he could rise, and led him through to
the bathroom again.
?I think you should close your eyes,? she suggested mischievously. He
did so and felt her positioning him from behind with her hands on his
shoulders.
?OK, open up.?
His eyelids lifted, and he felt a lurching disconnect which made him
sway. For the first time in his life he didn?t recognise the person in
the mirror. A pretty dark-blond woman in a white cotton bathrobe looked
back at him. Her dark rose lips parted in surprise, he eyes were wide,
and the bob swung slightly as she stepped back to recover her balance.
When he moved so did she.
?Oh my god,? she exclaimed in his voice.
Part 4: Possibilities
Dorothy held him up, her excitement giving way to concern at his
reaction. ?Are you alright? Let?s stop this ? I didn?t know what I was
thinking.?
?No, no. It?s OK now,? he said, steadying, ?I just had a weird feeling,
like I was looking at someone else in the mirror. It?s passing though.?
He could see himself in there now. The wig radically changed his look;
he hadn?t seen hair on his head for half a decade now, and never like
this. With his beard gone he could see his lips clearly, especially
accentuated by the lipstick. But, his eyes were the same, if a little
dilated with shock, they just seemed larger in their new setting for
some reason.
?Well, it looks like you were right about this part. My face looks OK,
but I think you may have a bit of trouble with the rest of me.,? he said
looking down at himself.
Dorothy was relieved that the shock seemed to have passed and Charles
was making a clear attempt to get over it with some humour.
?I?m not sure that?s a big issue,? she said seriously, ?you?ll be
sitting down in the office behind your computer. Only your head and
shoulders will be visible through the office window.?
She looked him up and down. ?All you would need is something to wear
that is obviously not male. A patterned blouse would do to complete the
illusion.?
?Let?s get this over with then,? he said with mock resignation. Inside
he was a little intrigued to see what difference this would make.
She laughed. ?Easier said than done. You might have noticed I?m a little
smaller than you ? in fact I take small sizes for a woman, so nothing I
have would fit.?
An odd, mixture of relief and disappointment washed over Charles. ?Well
that?s that for the moment then,? he said with a smile and reached for
the wig.
Dorothy put her hand on his arm and stopped him. ?No, I can go out and
get something, it won?t take long. Why don?t you keep the wig on to get
more used to it while I?m away? Think of it as preparing for an
undercover sting operation,? she smiled.
?Well I know I was in Vice, but I was never undercover. You?ve watched
way too many movies if you think we spent our time hanging around street
corners dressed as hookers.?
She laughed, and said, ?OK, for me, then??
?Fine, I?ll test drive it for a couple of hours. Unless someone comes to
the door of course.?
She hugged him and said, ?Wonderful. I won?t be long,? and dashed
through to the bedroom to get dressed. Within half an hour she was
headed out the door to go shopping for her husband?s first blouse.
Meanwhile, Charles was left to his own devices. He put on a casual short
and jeans then headed through to the small space that served as a study
and open his laptop. As he worked he slowly became used to the warm
weight on his head. After a while he was unconsciously tucking strands
of blond hair behind his ear and enjoying the feel of it swing as he
turned his head to look at different documents. An hour passed quickly,
and after sending a long and complex email he considered it a good time
to have a coffee.
While he was waiting for the water to head Charles wandered in to the
bathroom. He was responding to a strange curiosity to see how he looked
now that he was dressed. His reflection was less of a shock this time,
and for some reason the look seemed more ?complete?. It took him a few
moments to work out why, but finally he saw that for some reason, either
unconsciously or by coincidence, he had picked his brightest coloured
shirt; a red cotton with long sleeves.
As he gazed at his image his hands unconsciously crept up and completed
the last two buttons up to his collar as again this seemed to fit better
with this face and hair. He now noticed that much of the lipstick had
worn off over the last couple of hours and glancing down he saw that
Dorothy had left the tube on the surface.
He tentatively picked it up and removed the cap. Slowly he wound out the
overwhelmingly feminine makeup, and after a moment of hesitation,
applied it to his lips. It was far harder than Dorothy made it look, and
he had to take tissues to clean both the line of his lips, but also his
teeth after a major slip. He furrowed how brow in concentration and
persevered, finally achieving a result that satisfied him. Putting the
tube carefully back where he had found it, for some reason he didn?t
want Dorothy to know he had refreshed his lips, he ten glanced at his
watch and saw a shocking amount of time had passed. ?Ah!? he thought,
?Now I am beginning to understand why she takes so long in the bathroom
in the morning.?
With a crooked smile on his painted lips, he returned to making coffee
and then to work.
Once more he became lot in his work. Dorothy seemed to be taking a long
time for a quick shopping trip, but he had a lot to do to nurture his
growing client list and the time flew by. After a few hours he received
a chime from an incoming skype call and saw that it was from Mark. He
clicked answer, and after the usual greetings they efficiently updated
each other on client work that they were collaborating on. Charles
though that Mark seemed a little off at the start of the conversation,
but the young programmer quickly settled down to his usual geeky self as
they focussed on their work.
They finished the call than Charles was just getting back to work when a
thought chilled him a little. Had he used the video or just the voice
option on skype? He couldn?t be sure if w he would have noticed. Mark
never used video; Charles suspected this was partly nerdy social skills,
and partly messy apartment and questionable personal hygiene.
After a couple of minutes, he convinced himself that he would have
noticed a small video window with a image of blond woman, so decided to
let it drop and got back to work.
Bess
- 20.03.2021
- 12
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