From Office Worker to Dominated Slut
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From Office Worker To Dominated Slut 5 free porn video
Chapter 5
It was Thursday afternoon, 4pm. Office hours were officially 9am to 5pm,
but because the staff earned performance bonuses staff tended to drift
away anytime between 5 and 5.30pm. Eveline knew that Gerry was usually
one of the first out of the door, despite being one of the best
performers on her team, but not tonight. Tonight was his first stint as
her P.A and she had asked him to stay from 6pm till 8pm and he had
agreed. Of the other team members Jenny and Angela would probably be the
last to leave, together as usual, at just gone 5.30pm. Jayne had already
gone, asking if it was okay to leave early a few minutes ago, and she had
agreed as her workload was clear.
All the staff were busy at their computer screens or on the 'phone to
clients, including Gerry, although he had been up and down like a yoyo
all day, seemingly unable to keep still. She wondered if it was nerves or
excitement, or even a change of heart though she didn't think the latter
was likely. Gerry had decided on the name Tina to be used during his
hours as P.A and told her earlier that day, and Eveline had noted his
choice in a serious manner, but with a gleam in her eye since it meant he
was planning on turning up tonight and not backing out. She herself felt
a little sick in her stomach with anticipation. Butterflies, she thought.
She'd be fine once things got started.
She didn't really know what she had planned for him tonight and that was
making it more difficult. She would like to jump in at the deep end,
building up to things gradually wasn't her way, but at the same time she
had no idea what he got up to in his personal life and she didn't want to
frighten him off before they'd got started. She did know that he was so
far completely unaware that she had tapes of him, but she had brought her
digital camera to work today in the hope of coaxing him into a few
suggestive poses, and she wondered how he would react to that.
He might go running for the door. He might get turned on by it. Only one
way to find out though. She thought it was probably best to word things
so that they were questions or suggestions at first, e.g. would he mind
if she took some photos of him at work, would he lift his skirt up so
that he was exposed, and so on. She could easily rephrase things as
demands when he had gotten used to the situation. This was his first
night after all, and the contract he had signed was a fixed term of 6
months to cover for Theresa's absence. Plus there was the fact that there
was also work that had to be done during this time. She'd just have to
play it by ear the first time.
Breaking off from her paperwork a while later she saw that it was already
5.45pm and the office was cleared but for Gerry, as she got up to go the
toilet. When she came back she saw that he was shutting down his PC and
had picked up a sports bag from under his desk, next to his usual
rucksack. She smiled at him in what she hoped was a reassuring as well as
suggestive manner, as he excused himself to get past her in the doorway
and made for the ladies toilets himself. She was about to make herself
another coffee, but stopped. That could be his first job she thought, to
make them both a drink.
She had told him that whilst he was working as Tina he would be using the
PC at the side desk in her office which was Theresa's, because it would
be easier for her to ask him for things, give him instructions and so on
without shouting into the main office, plus all the main files were in
here, on paper and on Theresa's machine. There was also the unspoken
observation by both of them that there was less chance of anyone
wandering about the building after hours noticing anything untoward if
they looked into the main office.
After all if she wanted privacy she could shut the door and blinds, and
if it wasn't necessary and someone glanced in e.g. a security guard on
his rounds, they'd be unlikely to recognise Gerry from across the office
if he had his back to them since with his long hair down, dressed in
skirt and blouse etc, he would just look like a "normal" secretary. Only
someone from in their own office might recognise him from his hair she
thought. But after 6pm there shouldn't be any interruptions other than
the security guard who wandered round checking doors etc were locked
about once every 2 hours.
There was more than one company in their office building, but theirs was
the only one of this floor, and after 5pm all visitors coming in had to
pass another guard on the main reception desk, and sign in, even if they
worked here during the day. Plus they were asked where they were going
and their imminent arrival was notified to the appropriate person by
'phone. She had already 'phoned down tonight and informed Alan on the
desk that she and another colleague would be working late till
approximately 8pm, so the other guard wouldn't bother to check their
floor. If she was working late alone they sometimes popped in to use her
coffee facilities as they had none themselves, and also to make sure she
was okay, but as she had said she was with someone she knew they wouldn't
interrupt, as they weren't supposed to disturb the office personnel.
Gerry a.k.a Tina walked back into the main office, and stopped to replace
his bag under his desk. The transformation was complete as requested, and
he had to chosen to wear a white satin blouse through which the outlines
of a white lace bra (which looked padded from the way it pushed at the
blouse) were vaguely visible. The blouse was tucked neatly into a
straight black pencil skirt that stopped just above the knee. Beneath
these were his stunning legs encased in black nylon, which she hoped were
hold-up stockings as required, otherwise she'd need to teach him
discipline she thought to herself. To finish this off were a pair of
immaculate shiny black patent leather stilettos which looked brand new,
and which seemed higher than her own pair.
That reminded her, she'd need to sort out his expenses soon so that he
could keep up this standard of dress. All in all, he looked very
presentable for his new job, with his long hair gleaming under the
fluorescent lights and he seemed to have taken much more care in his
appearance then he would have for his day job. In fact she suspected he
looked smarter and more feminine than she did right now after wearing her
own clothes all day and the overall effect was to make Eveline want to
get him in as many compromising positions as possible in order to make
his clothes rumpled, creased and in disarray. Her nerves seemed to have
disappeared she thought, as felt a grin spread across her face.
Control yourself woman, she chastised herself. Tina stood there a little
uncertainly, tottering in the high heels as though unused to walking in
them, though she wouldn't be at all surprised to find out that he had
worn other pairs before. Perhaps it was their height that was new to him,
or just the walking around in them for any great distance. Maybe it was
because he was nervous too, but either way he made a very passable job of
walking smoothly to her office door from his desk, despite the fact that
he must have been aware that she was watching him. She smiled up at him,
trying not to show that she felt like she could eat him alive, and said,
"Hello Tina."
He smiled back losing his uncertainty in an instant and walked up to her
desk. "Hello Eveline. Where would you like me to start?"
"Well if you don't mind, I'd prefer to be addressed as Miss Jamerson, or
better still simply as Mistress or Madam during your evening hours Tina,
though it may take a while for us to get used to that. That said, I think
since we've both been here all day and still have more work to do, why
don't you start by making us both a coffee? I think you know the way I
like it," she said with a smirk and a wink.
"Certainly madam," he replied, and walked out to the kitchenette, aware
that once again her gaze was following his every step. Indeed, Eveline
could feel herself practically drooling over his legs and the pert cheeks
of his bottom as they moved against the fabric of the skirt, and it
certainly looked very nice she thought. He looked great and had obviously
shaved his legs, which although she hadn't thought to specify was the
right thing to have done considering what else he was wearing. He wasn't
wearing make-up she had noted, but she thought that was something she
could introduce him to tonight.
As Tina stood there waiting for the kettle to boil, leaning against the
counter with his back to Eveline's office, he felt pleased. He could see
that she liked the way he looked and was glad. He felt he looked good as
a woman too, and was pleased that he had kept his hair down, rather than
in its usual ponytail. He had considered pinching a little of his
girlfriends make-up that looked like it hadn't been used for a while,
since he hadn't wanted to buy new, but decided that he wouldn't know how
to put it on properly without practice, and he hadn't had time for that.
He was enjoying being dressed like this, but he was aware that it was an
infrequent occurrence for someone else to witness it and it would only
take a moment for someone to laugh at the wrong time or make a comment in
jest, to make him feel the object of ridicule and leave him feeling
humiliated in a way that he might not recover from enough to dress this
way again. This was an act of release for him that he didn't want to
lose, and he didn't want to feel stupid by dressing poorly, so making a
mess of applying make-up that he wasn't used to was too risky. He wanted
to feel good because he knew he looked good. He was a little scared that
Eveline might have impossibly high standards, but she had reacted warmly
to his entrance before, and hadn't been the least bit condescending when
she asked him to make coffee.
She had been smirking to herself, but it didn't feel as though it was
malicious, and it seemed liked she enjoyed seeing him dressed like this,
rather than getting power from trying to make him feel small and silly,
which was something else he had fretted over in the last few days. He
finished making the drinks, and saw one of the old silver serving trays
stashed on a shelf under the sink. He quickly polished it with a tea-
towel and put the drinks on it along with a saucer with a few digestives
on it, feeling she might appreciate the gesture but also feeling absurdly
like a waitress rather than a secretary on his way back to her.
She was sat back in her chair legs crossed, idly fiddling with a pencil
when he came back in, still smiling. "Thank you, Tina," she said as he
offered her the cup and placed the tray on the edge of his own inherited
desk before passing her the biscuits too. "Such initiative on your first
day," she added teasingly. He sat down and took his own cup without
saying anything.
"First things first, may I say you're looking very smart and elegant
today and I hope it will continue. Before we get down to work though, may
I suggest a little like make-up during your evening hours in future? I
have some here you can try for starters if you'd like?"
Tina looked at the small black cosmetics purse she was holding out to him
awkwardly. "Thanks, but I erm..." he started a little embarrassed, but
she helped him out instantly before his blush could get started.
"Let me help you," she said. "If that's okay with you of course." And he
nodded silently as she came over to his desk and crouched beside him on
her knees, legs crossed behind her, and starting taking things out of the
bag and putting them on the desk, opening up the little compact mirror,
and talking all the time, to put him at ease he supposed, though he felt
fine in himself even though things were somewhat surreal. She showed him
how to put foundation onto the little sponge and where to dab it onto his
face mimicking the motions on her own face which was already immaculately
made up. She moved onto the blusher, and then the lipstick.
He seemed to find the latter a little more difficult and so she turned
his chair to face her and leaned over taking hold of his chin and applied
it for him, following it with some eye make-up, by which point the smooth
line of his skirt was spoilt by the bulge pushing against it at the
groin. His breathing had become a little heavier and quicker too she
thought as she leaned back. She desperately wanted to kiss him then, and
spoil the perfect lipstick she had just put on, and their faces were
still only inches apart, but she made herself pull away, and pushed
herself upright, placing her hands unthinkingly on his stocking clad
knees to do so, his skirt having risen up a few inches when he sat down.
Tina drew in his breath sharply at that point, and she felt herself
become embarrassed as she tried to apologise for something that whilst
unintentional having previously promised not to touch, was at the same
time something she wasn't really sorry for. God, his leg muscles were
firm. This time it was his turn to put her at ease and he said it wasn't
a problem.
Gratefully, she suggested they get a little serious business out of the
way, and for the next half hour or so Tina tried to keep his head focused
as she showed him where certain files were kept and so on, aware that
Eveline seemed work orientated for the time being, but also painfully
aware of the stiffness of his erection and that she either hadn't worn a
bra all day, or had taken it off earlier, because her nipples were
obviously hard and could be seen through her blouse which was quite
clingy. He was trying to cope with his erection, aware that he didn't
have to hide it, as she'd seemed pleased when he responded that way
previously, yet trying to concentrate on what she was saying. He was
desperately also trying to remember that he had a nice girlfriend at
home, but here he was dressed as a woman with a raging hard-on, and the
constant thought nagging at him to grab hold of both those nipples and
squeeze until she groaned with pleasure. But that was the problem. His
girlfriend was "nice." Nothing like this was anywhere in the picture with
her. Concentrate he told himself.
"I'm sorry?" he said, aware that she had asked him something and was
waiting for an answer.
"I said, do you have any experience using Microsoft Access and Word? I
know we use Powerpoint a lot during the day, and Excel, but if you need
to get to grips with the others, I might need to give you more time
before I offload some work on you."
"I'll manage," he said clearing his throat, "I can always ask if there's
something in particular." I'll manage he thought to himself. Ha. Managing
to use those was going to be nothing compared to managing his own
feelings. But he already knew he couldn't give this up without following
Eveline down whatever route she had planned for him a while longer yet.
She glanced down at his lap, amused but in a nice way. A damp patch was
apparent again. She moved back to her own chair to put some distance
between them even if it was only a couple of metres. Picking up her bag,
she asked him if he was wearing stockings as requested and when he
answered yes, she asked him if he was wearing anything else under the
skirt.
"A pair of black lace panties," he said looking straight at her and still
breathing heavily.
"Well would you mind pulling your skirt up a little so that I can see?"
Eveline smiled at him. Slowly, Tina pulled the skirt up at both sides
until the crotch of the panties could be seen.
"They look very nice, but I can't really see them that well," said
Eveline, "maybe if you pull the skirt up all the way I can see things
clearer?"
Tina obligingly lifted himself a little out of the seat and pulled the
skirt up till it was completely around his waist, and he has sitting
exposed from the waist down but for stockings and panties. The bulge in
the latter increased considerably as he looked at Eveline and saw her
looking at it herself, still smiling. The smile hadn't left her face from
the moment he turned up dressed like this he thought, apart from when
she'd been concentrating on real work. He felt nervous, and exposed,
seeking her approval and not knowing what to do with his hands. She
noticed his fidgeting and said, "It's alright you can play with it, so
long as you don't mind me watching..."
His hand instantly found his penis and he starting rubbing at it from the
outside of the panties and straying down occasionally to cup his balls,
but his eyes never left her face until she opened her blouse, at which
point he felt himself watching her hands as she played with her left
nipple through the fabric, and he wished the blouse would fall open
further, as he wanted to see more, her right nipple being only just
visible at the edge of the material. He squeezed himself and groaned
openly.
"I brought something with me from home," she said innocently, glancing at
her bag, "and I'd like to use it now if you've no objections. I
understand if you're not ready to trust me totally just yet, but I have
to warn you though that you did sign a contract allowing me to do pretty
much anything..." she added sweetly.
For a moment Gerry wondered what was in the bag and whether it would
involve pain or bondage but he didn't know what to think and he waited
with bated breath until she pulled out a digital camera and then relaxed
again and continued squeezing himself over the panties. His head reeled
just for a moment as he thought to himself, "She could do anything with
the pictures, put them round the office, on the net, blackmail me over my
girlfriend or anything..." but somehow he knew she didn't have any of
those things in mind.
He found it hard to believe how much he trusted this woman whom he still
knew so little about despite having worked for her for some time, but he
felt safe for some reason. He closed his eyes and leaned back as he tried
to get a harder grip on his cock through the lace but he was brought back
by her demanding that she look at him. When he did she started snapping
pictures, one after the other, close-ups of his hands, and full view
shots of him sitting there, skirt around his waist, in stockings and
heels, and all he could think was that his cock was so hard it felt like
it was ready to explode.
He felt torn in half by his emotions. Part of him desperately wanted to
dominate this woman who had gotten him in this vulnerable position,
wanted to rip her clothes off and force himself on her whilst still
dressed as a woman, but the other part of him was reacting to the camera
and he found himself moving around, trying to give her a better view so
that she could take clearer pictures of what was going on.
She had obviously noticed this and teasingly said, "You little slut...
you'd better open those legs further for me then hadn't you? That's it.
Spread them nice and wide so your mistress can see everything... Better
move those panties to one side to and set him free too."
As he did as he was told to the sounds of the camera zooming in and out,
she saw the size of him and said, "Someone's enjoying themselves aren't
they? Well don't just sit there and waste it honey, get a good grip and
let me see some real action..."
He gripped the shaft which still looked massive to her even encased in
his hand, and started making swift up and down movements. As he did so,
she put the camera down briefly and removed her open blouse dropping it
at his feet. Pushing her own skirt around her waist and slipping off her
shoes she sat back down in her own chair but moved it closer to him, and
picking up the camera started taking pictures again, while he sat there
staring at her breasts, then down to the place where her knickers would
have been had she been wearing any, and then back at her face, watching
her smile as she watched him through the camera display.
She saw that he had also shaved around his cock and there wasn't a pubic
hair in sight, and she appreciated the thought he must have taken in his
appearance. It was something she really should have specified but had
forgotten to but he'd done it anyway and it all added to his assumed
femininity. She started stroking up and down the inside of his lower left
leg with her stockinged foot and it was only moments before he came in a
shuddering climax.
A little out of breath he panted at her, "I'm sorry."
Smiling even now she said, "I'm sorry mistress."
He repeated it after her and she took his hand and briefly kissed it in
an old-fashioned chivalrous manner and replied, "No need to be. You did
as you were told and I got what I wanted."
And she stood up and replaced and rearranged her clothing.
"For tonight at least," she added with a wink. "I'll let you clean
yourself up," she said and went out, leaving the camera on the desk..
Tina felt exhausted and glanced up at the clock, it was 7.45pm. She had
said she wanted him till 8pm tonight. Was she going to come back and
demand more? He panicked, wondering if he'd be able to keep up. Grabbing
some tissues from the box on the desk he quickly cleaned and tidied
himself up. She had left the camera on the desk he saw. In plain view of
himself. Hmm, he suspected this was another test. If he was worried or
nervous in any way he could quickly grab it and delete everything off the
memory stick and he knew that she knew that.
He didn't want to anyway much to his surprise. Having pictures taken of
him in that position, both wearing feminine clothes and playing with
himself at the same time had only gotten him even hornier than he had
already been. But he would like to see them. Still, he didn't know where
she had gone, how long she would be and most of all what she would think
of him looking. He didn't want to do anything that might lead to the
denial of future privileges, so to speak. If she came in and found him
looking she may assume he was going to delete them and be cross at his
lack of trust, or she may be pleased at his curiosity. He decided it
wasn't worth the risk, and was glad as the door opened seconds later. She
saw him sitting there looking all innocent in his chair and glanced at
the camera.
"Did you touch it?" she asked.
"No mistress," he replied.
"Good girl," she commented, "Would you like to see the pictures?"
"Please," he said carefully.
"Very well, but not now. It's nearly home time. I shall put a new folder
on the desktop of that PC," she said back in efficient mode, pointing to
Theresa's PC on the corner of the desk, "and set it so that you have to
log on to start the machine up. The password will be Tina. I will look at
these pictures at home, and those I feel are suitable will be placed in
the folder for you to view, delete, copy or print as you choose, but I
will always keep a copy for myself. Okay?"
"Yes mistress," he replied meekly looking down at his hands.
She looked at him, with her head cocked on one side and said, "Aren't you
worried about what I'll do with my copies?"
Looking straight at her without flinching he said, "No. I trust you."
Her smile widened even further, and she said, "Excellent. I think that's
it for tonight Tina. You can go home now. Thank you for staying" and then
as he stood up to leave added in a surreptitious whisper "Don't forget to
wash the make-up off first," and patted him proprietarily on the behind
as he walked out of the office.........
...................................................................
I was aware as I posted the 4th part, that the previous chapters were a
bit teasing. The reviews of the 4th kind of confirmed it to me, I hope
this chapter has made up for it to some degree.
[email protected]
Maddie
- 24.11.2022
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