The Mrs Hollingsworth Project Part 9
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The 'Mrs. Hollingsworth' Project (part 5) free porn video
"The 'Mrs. Hollingsworth' Project"
(Part V)
Two days later the private elevator door opened on the penthouse floor
of the Hollingsworth building, Rick and Ms. Lawrence stepped out and
moved to the main door of the vast penthouse suite. This was Mr.
Hollingsworth's private floor.
"It's not an apartment actually, I reworked a section of the penthouse,
it's a suite of rooms." Rick said as he opened the main door to his
apartment. Ms. Lawrence followed him through the foyer to the left this
time, to the other side of the apartment she hadn't seen. Down another
hallway, past closets and pantries, past a spacious kitchen with a large
formal dining room in view near the windows overlooking the city below
and down another short hallway to a large set of white double doors.
Rick opened the doors and led the way inside. Ms. Lawrence looked
around, the scent of perfume already in the air of the large bedroom
that was done up as a woman's boudoir but this was overly done,
excessive in it's hyper-feminine design! Rick followed Ms. Lawrence as
she looked around.
She noticed the white nylon window sheers and the satin draperies, the
pastel pink carpeting and the room filled with white French provincial
furniture. Two large dressers, a large woman's vanity draped in white
layered nylon chiffon skirting, a small chair, the seat covered in heavy
white satin sat before the large mirror affixed with a ring of lights,
the top of the vanity already stocked with every manner of makeup and
hair care products ready for use!
The four poster queen sized bed was also done up in white with a
delicate lace trimmed floral patterned cover, the bed itself with a
matching floral satin comforter. The walls covered in a pale pink to
match the carpet and draperies with sections of delicate floral
wallpaper on walls, behind the vanity and on the wall leading to the
large double door walk in closet.
She moved down a small hallway and into a huge master bath, also done up
in white with pale pink trim and gold fixtures at the sink and large
bath tub near the center of the room. A large wall length mirror sat
behind a double sink wash counter in along one wall and through another
door was a private beauty salon! Ms. Lawrence turned and headed back to
the main bedroom to finish her inspection, her heels clicking loudly on
the white tiled floor, her nylons zipping with each step. "Well? Do
you like it? What do you think!?" Rick said excitedly as he followed
along waiting for Ms. Lawrence's approval.
She entered the bedroom and looked through the dressers and found them
already stocked to the hilt, brimming with all manner of expensive
ladies lingerie, foundation garments and hosiery. She then moved to the
closet doors and threw them open wide to reveal row upon row of vintage
skirts and blouses, dresses, evening gowns and night gowns. Hat boxes
and hosiery boxes filled the shelves and dozens of pairs of high heeled
shoes all with 5 and 6 inch stiletto heels lined the carpeted floors.
Ms. Lawrence had seen enough!
"Where is Tim now?" she asked.
"I put him up across the street in a suite at the Hilton," Rick replied.
"Well he obviously hasn't seen this yet has he. Because he'd be gone
once again if you'd have showed this to him!" she continued.
"Why!? What's wrong with it!?" Rick questioned.
"It's too much! Too over the top, over done!" she returned. "If this
is going to work we have to be subtle, work him into this new situation
one small step at a time, gradually! And I have to have time to do my
work as well. This won't work this way. No. He'll move in with me,
today. We'll begin in the morning." she finished. "You're not to tell
him about this boudoir, understand Richard?" she finished.
"Okay, I'll turn everything over to you, starting now. But when can I
see the progress?" he asked.
"Maybe once a week, a dinner or drinks some evening maybe. I'll let you
know." she said with an air of authority. With that they left the
boudoir suite closing the doors behind them. Then they left the
penthouse apartment and returned to the elevator. "Call him, have him
meet me at my apartment in the morning, early, we'll start there. And
allow him to bring his suitcase, the one with male clothing."
"What for?" Rick added.
"With male clothing in the closet he won't feel threatened now will he?"
she finished. Rick nodded his understanding, letting her take full
reign.
An hour later in the Hollingsworth building a few floors below the
penthouse apartment Ms. Lawrence swung the door to her apartment open
and ushered Tim inside with his duffle bag. She showed him his bedroom
at the other side of the apartment from hers. It was a large well
appointed apartment with 4 bedrooms, a large kitchen and dining area, a
study and a large living room area. She got Tim settled then told him
to unpack and once that was done to take a hot bath. She insisted that
he start by shaving his body totally smooth below the eyebrows! He was
allowed a small trimmed triangle of hair below but that was it! He
quietly complied. An hour later Tim with a towel around his waist was
back in his bedroom.
It wasn't a man's or a woman's bedroom, more of sturdy classic design
with large bed, gray carpet, off white draperies, and standard desk,
dresser and closet space. Tim entered with a towel wrapped around his
waist. What little body hair he'd had was now evidently gone, he was
smooth skinned pink and below the eyebrows totally hairless! Ms.
Lawrence entered with a small zippered case. "Have a seat," she said.
"What's up?" Tim replied.
"I'm going to give you a pedicure!" she said as matter of fact.
An hour later Tim sat on the edge of his bed, his toes in pink toe
spreaders, his toenails now sculpted, trimmed and shaped and also a
bright, gloss, red! He looked towards Ms. Lawrence who was now looking
through the nearly empty closet at the duffle bag now folded and set on
the floor. She noticed the two winter jackets and at the three wrinkled
suits, shirts, various colored T-shirts, a couple pairs of cargo pants
and on the shelf several pair of blue jeans. A pair of wingtip dress
shoes, loafers, two pair of tennis shoes, a pair of boots and a pair of
nice walking shoes and lastly a pair of men's slippers sat neatly on the
floor. "We'll send everything out to be cleaned and pressed later." she
said as she moved to the dresser where she noticed a couple more T-
shirts, white and colored socks and shorts and a set of men's pyjamas.
She then left the room momentarily.
She returned with a box of new clothing and a plastic garbage bag. Then
opening the dresser once again she began gathering most of the male
socks all the male shorts all the white T-shirts and took the pyjamas
away and bagged them as well. The few pair of socks that remained were
placed in the bottom drawer. Ms. Lawrence then filled the top drawer
with a dozen pairs of lace trimmed ladies nylon vintage full briefs, a
dozen pairs of nude support pantyhose, several white girdle briefers,
three 6 strap garter belts and a dozen pair of size 11 long sheer ladies
nylon stockings, a third in nude, a third in beige, and the rest in
neutral gray. She finished by taking a pink layered nylon chiffon baby
doll nightie and matching robe to the closet to hang them up and
replaced the male slippers with a pair of pink high heeled marabou mules
with 6 inch platform heels.
She checked to make sure the polish was dry on his toenails then removed
the pink toe spreaders. She handed him a pair of the white lace trimmed
ladies nylon briefs and a package of support pantyhose. "Get dressed
and pick out a nice pair of slacks and shirt. Make sure to hide any
unsightly bulges. I'll be looking over some paperwork in the kitchen
when you're done. I hope you don't mind a working lunch?" she said as
she gathered the half full garbage bag, the empty box and left the room.
When Tim finally entered the kitchen in his cargo pants, T-shirt, dress
shirt jacket and walking shoes Ms. Lawrence approached with a cloth tape
measure. She took Tim's measurements this time instead of jotting down
clothing sizes to get a more accurate size this time and to chart her
program's progress. 40 minutes later they were seated in the back of an
upscale downtown restaurant.
"So, I take it the 'executive assistant' job was just a smoke screen
then?" Tim asked over his hot cup of tea.
"You're being paid but that's up to you and Richard Tim dear. I'm hear
to work with you, to help you along. He's settled on the name.
'Tiffany.' I trust that will be alright with you?" she said looking
across the table at the young man sipping his tea.
"I don't think the name 'Tiffany' goes with this look do you?" he asked
still not really contemplating the scope of the grand plan.
"It will dahling, it will!" she said with assurance.
This tea's a little bitter," he added.
"Maybe it's a different kind than you're used to. Add a little extra
sugar and cream if you like," she went on, looking over some notes not
bothering to mention that she'd poured in some liquid female hormones
into his drink without him seeing it!
"I'm having some other clothing and some reading material brought to the
apartment. It should be there upon our return. Then we'll see where
you are in the grand scheme of things and where we'll need to start."
she mentioned as if she was interviewing a new debutante for her charm
school.
The waiter arrived with their lunch. Ms. Lawrence had a small fish
filet with lemon grass and tarter sauce, toast and a green salad with
water, Tim had a deluxe hamburger with steak fries and a coke.
"I'm not gay or weird!" Tim whispered under his breath across the table
as they began lunch.
"I tend to agree, although we're not here to debate that," Ms. Lawrence
returned.
"It's just that...just that I really enjoyed the ride in that corporate
jet, the trip on Mr. Hollingsworth's yacht and the traveling and meeting
all those different people and living in that nice lifestyle, being
catered to you know? I knew I wouldn't do as well when I left but
didn't realize I would be stuck right back where I started from. And
then to end up back here, broke with barely the clothes on my back?" Tim
commiserated. "So, I figured that if Mr. Hollingsworth wants to dress
me up and watch me strut around now and then, maybe that wouldn't be so
bad. And instead of seeming weird or crazy it started seeming like a
real bargain, a bargain in my favor! You know?" Tim reasoned.
"So, considering your 'promotion' from executive assistant to where you
are now. I think Mr. Hollingsworth mentioned special projects? Ms.
Lawrence spoke.
"Yeah, something like that," Tim added.
"Well, it seems that your promotion is that YOU will be the new 'special
project.'" She added. "Of course I'm sure you'll be free to do pretty
much as you like and you may have some official duties, an actual job
description after a time, but that's where we sit at this time. Do you
understand?" she finished watching a now nervous Tim squirming in his
seat knowing that under his slacks his legs were now smooth shaven, he
was properly pedicured and dressed in ladies lace trimmed nylon panties
and nude support pantyhose! Her measure of control had as per her plan,
already begun!
"Therefore you are now my special project, why I'm here," she began.
"You are to be my only student, my only pupil."
"You mentioned something about that at the boat," Tim added.
"Specifically I told you that I was going to feminize you. And I am
dahling!" she interjected noticing Tim's face begin to redden. He now
felt the sensation of the lingerie he was wearing under his slacks!
"I've seen the video log of your little performance in Mr.
Hollingsworth's private salon on the boat. Part of a security camera
system," she mentioned.
"Tim sat bolt upright, his nervousness present.
"Don't worry. It's not being shown to anyone. Richard had me watch it
to make an assessment of you," she said. "He told me about seeing you
for the first time at that Halloween party. I know about your special
suitcase? The one at your old apartment?" And in seeing that
surveillance disc it is quite apparent that you're a cross dresser And
from what I can tell, a good one! Part of the start of your charm
school training is to ascertain just how far along you are, then we'll
go from there," she said quietly.
"It's a bit...it's a bit embarrassing to talk about," Tim stammered.
"It's something I can't help."
"I understand why that is. And what got you started with your interest
in ladies things?" she inquired.
"Nylons...Nylon stockings I...I guess Ms. Lawrence," Tim said quietly.
"I found some drying over the shower rod when I was just a little kid.
They were hanging there shining in the sunlight. I felt them and they
were slippery to the touch. I wanted to try them on, so I did. They
were shiny and smooth and very slippery and when I rubbed my legs
together I heard the stockings zip just like they sounded when ladies
would walk or sit and cross their legs!" he explained.
"Yes, yes sheer hosiery does feel exquisite doesn't it? But what about
the rest, wearing everything, being fully dressed?" she asked.
"I noticed the nylon slips and they were smooth and silky too so I
started trying them on, and then panties, girdles and then bras to make
the slips and dresses fill out and finally I tried on some high heels
and learned to walk in those. I knew it was wrong but I couldn't help
it! I liked the way all the clothes felt Ms. Lawrence," Tim gasped, the
confession wearing on him.
"Do the clothes make you feel like a woman, make you wish you were a
woman?" she noted.
"I don't know. I...I just like the clothes I guess, I don't know why
but they feel so good," he finished.
"We'll be exploring that. It seems that your 'type' has an even finer
tactile sense than a real woman does...interesting," she said making
notes in her notebook. "But I hope you realize that as we continue I
want to see how you walk and move while dressed as a woman."
"Yes. I get that. Just so you don't make fun of me," he added.
"Oh, quite the contrary dahling!" she added. "This is all hush hush and
top secret, nobody knows about this little project except you, myself,
and Mr. Hollingsworth. Everything will be fine, you'll see. After we
finish our lunch we need to make a few stops then we'll return to my
apartment for the rest of the day," With that they quietly finished
their lunch. Two hours later in they were back at Ms. Lawrence's
apartment.
Tim was uneasy, his face blushing as Ms. Lawrence finished dressing him
by zipping him into a rayon house dress. While they were gone more
clothing had arrived, clothing in Tim's size. She'd watched him dress
from head to toe and from the skin out in layer after of layer of
feminine lace trimmed lingerie. How he tucked himself into his panties,
how he hooked the garter belt up, how he slipped into the sheer nylon
hose and gartered them. He'd had practice. The brassieres were a bit
larger now, at her discretion, the weighted silicone forms larger than
the ones that Mr. Hollingsworth had picked during the boat trip. But it
was along the lines of her style and class, striving for the best fit of
the dresses now hanging in the closet and those still on order and the
look of her latest debutante! She then sat him at the vanity in her
bedroom. He was apprehensive when she started applying the red lipstick
to his lips!
Not being critical, not even thinking of Tim as a man she started as if
he were a new student, taking her course! "You should usually start
with a lip pencil, gives a sharper more defined line. You have nice
lips! Ms. Lawrence said as she continued on with Tim's makeup. She had
already removed the gold studs from his ears, ears that were pierced
right after lunch that day! Dangle earrings now hung in their place,
with the addition of that pearl necklace he wore on the cruise!
She carefully explained the foundation, the powder, the lipstick and
mascara and eyeshadow as she worked, instructing Tim as she went along,
using techniques and skills that he hadn't yet mastered, but he soon
would. Once finished she combed his hair back into a tight ponytail.
She then had him move into the living room where she watched as Tim the
'lady' was put through 'her' paces!
She had him walk like a woman, of course being dressed as a vintage
housewife type in full lingerie and a rayon house dress it was much
easier. The 5 inch stiletto heels forced Tim into a feminine walk, but,
with the practice he already had he made it look natural. The dress
swishing, the nylons zipping their familiar "shick-shick-shick" sound in
classic fashion. Ms. Lawrence was impressed. But there was more to do,
more to fine tune.
Tim walked a bit breathless and embarrassed, his head spinning as he
minced around the living room dressed once again but now in front of Ms.
Lawrence for the first time! As the dress rustled and the nylons zipped
she noticed his open mouthed breathing, the vacant glassy-eyed look on
his face as he surrendered to the sensation of being fully dressed once
again. Nevertheless she continued with her latest 'debutante' as she
had with countless other up and coming ladies of wealth and culture.
Tim was now getting first class tutoring!
"Now, turn on the ball of your foot, not the heel, you'll wobble or trip
otherwise dear!" Ms. Lawrence said as she watched Tim reach the end of
the living room then turn to make a return trip. "Relax the arms, palms
up, turn the thumbs out, not so stiff, limp wrists!" she said as she
watched closely. He took her direction to her satisfaction. "Stop,
turn and curtsey!" she ordered. He did as he was told with near
perfection then continued on back and forth across the large living room
as Ms. Lawrence made notes!
"Continue, down and back, yes, that's it! Very nice darling!" she said
as he minced and wiggled to and fro, the dress rustling, the nylons
zipping just as designed. She stopped him to have him try a purse.
First carrying one by the straps, then carrying one over the forearm by
the straps just like a lady. Clumsy at first but a few tries showed
improvement. Tim was a near natural. And he hadn't wobbled or tripped
or stumbled on the high stiletto heels at all! A far better performance
than many high society ladies she'd tutored over the years! Ms.
Lawrence was impressed.
"Come over now, sit with me on the couch dahling!" she commanded. Tim
stopped his pacing and sat down. She watched as he gathered his skirt
under himself as he sat down then heard the silken zip as he crossed his
nylon clad legs and smoothed his skirt. She was impressed!
It's getting late dahling," she said. "Go ahead, get undressed. Put
your lingerie in your dresser, hang up your dress and then you may
shower. You can dress for bed by putting on that pink nightie and robe
hanging in your closet," she said. With that Tim left the room to do as
he was told. Ms. Lawrence made a few more notes.
Three days later the day ended with Tim, back in the same lingerie and
the same layered black nylon chiffon flowing robe that Rick had gotten
for him on the cruise. Now Ms. Lawrence was first hand witness to just
how good Tim could look. And with her help with makeup and in doing his
hair instead of him using a wig even she had to admit, he was stunning!
The next afternoon after giving Tim a day off she went to Rick's
palatial office for the first of her 'conferences' on 'special
projects'!
"So, how's Tim doing!?" Rick asked excitedly.
"Well, he's a queen, a real 'lady'! Or he should have been!" Ms.
Lawrence said nearly dumbfounded. "There's some odds and ends a few
details and he's got a lot to learn about hair and makeup but I'm
betting he'll do as well as any real lady I've ever coached!"
Rick leaned back with that "told-you-so" attitude and smile proving once
again that his business sense, his instinct was right on track. "I saw
him that night at that table in that bar and I thought it was a real
woman at first! Amazing!" he said with excitement and determination.
"When do we tell him we've already started him on female hormones?" Ms.
Lawrence said in passing.
"We don't!" Rick finished as he stepped out from behind his large desk.
His latest project well underway now, and underway to his satisfaction,
a work in progress that he couldn't wait to see through!
He'd searched long and wide, he'd found two beautiful women but women
who didn't share his love of that vintage classic feminine look. But
now, now he'd found a quite unlikely prospect, a 20 something young man
named Tim. And now Tim was being properly groomed. Rick was now
satisfied!
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