I must give Cheryl Lynn credit as the basis of this story is a take off,
a different look at her story entitled "Mother-In-Law." My version is a
bit different but I hope maybe a bit deeper and every bit as exquisitely
and inescapably feminizing as the original. Anonymous writer-
"An Exquisitely Ordered Lifestyle"
It had been a bit of a rough deal and six weeks later, although the
situation had calmed down things had changed. Tim's wife had found his
large black suitcase in the garage by accident. It was a stupid mistake
but it had happened. He was working at home as usual and had noticed
the lightbulb on one of the garage door openers had gone out. A simple
fix, get the ladder out, put in a replacement light bulb and end of
story. But, in this case it was only the beginning of the story!
Tim had gotten side tracked. After changing the lightbulb the phone
rang and then he had to check the casserole he had going in the oven for
supper that evening. He forgot to make the salads so after the phone
call he started in on those then set the dinner table. When his wife
Cindy returned home from her office she didn't notice the ladder in the
middle of the garage that Tim forgot to put away. She bumped into the
ladder with her car and knocked it over into a large wooden shelf which
caused a box and a large black suitcase to tumble to the garage floor
with a loud, heavy thud. After putting the ladder away and putting the
box back on the shelf she reached for the large suitcase and found it
filled and heavy. Once she unzipped the case and opened it and saw the
carefully folded collection of ladies clothing and accessories Tim's
secret was now out once and for all.
They were a young, moderately well-off couple who'd been married only a
few years. Cindy had learned about Tim's "hobby" after catching him one
afternoon dressed in his women's things. Nothing radical, just a
blouse, skirt, hose and smart ladies shoes. He didn't fuss with much
makeup or do his hair, he was just spending the afternoon like that in
his home office while working. He tried to explain as usual, to defuse
the situation, to dismiss it as the harmless hobby it really was. He
didn't do it every day, just now and then. It took a few weeks for her
to get over it, she didn't want to know anymore about it and tried to
put it out of her mind to get back to the way things were. After all
they had a good life and got along very well but, that suitcase was now
a game changer.
That's where he had hidden all his things. And in opening the case
Cindy now knew that this was far more than just a casual thing. She
confronted Tim again, and this time she was angry. But although the
storm seemed to pass, Tim began to notice a distance between them he'd
never known before. Like she was pushing away now. The engaging dinner
conversation fell away as did the romance. The next few weeks passed
and it seemed like business as usual but things had changed now, for the
worse. The evidence came one evening when Cindy returned home and told
him that "Mother wants to see you this evening, after supper."
He'd put the suitcase back on the garage shelf where he'd always kept
it. He hadn't touched it in the six weeks since Cindy had found it. But
things still didn't change for the better. As he left for the
conference with Cindy's mother and as he backed his car out of the
garage, for some reason he looked to the familiar shelf. This time the
large black suitcase that was always there was now gone!
Tim didn't put two and two together at first as he drove out into the
exclusive suburbs but he felt a nagging question at the back of his
mind. He had to visit his mother-in-law and now his case was missing?
He pulled up to the service box at the front gate of the secluded tree
lined estate. The large metal gate opened and Tim pulled into the long
driveway. He parked in the small roundabout at the front of the house.
He walked to the large front door and rang the bell. His mother-in-law
answered and let him inside. She closed the door and motioned him into
the living room, asking if he wanted a drink, which he declined as he
felt his nerves starting in.
Madge Greystone had always been a bit "cool" to Tim. She always called
him "Timothy" which he didn't really care for, it always seemed to
reinforced the strictness she seemed to exude. But this evening she
seemed a bit more severe. Madge didn't waste anytime starting the
conversation.
"Where's your housekeeper?" he asked looking around. Since Cindy had
taken him to meet Madge when he met her that first time her housekeeper
Lindsay was always flittering about, matter of fact she always answered
the front door too. But this evening Madge had answered the door
herself. "She's been discharged," Madge said in passing then continued.
"Timothy Benson. I think it's safe to assume you know why I've asked
you here," she started in cooly.
"Well, I'm not really sure ma'am," Tim answered.
"Ms. Greystone. From now on you will address me as Ms. Greystone. Is
that understood?" she returned.
"Alright, sure," Tim returned a bit nervously.
"I prefer to live a well ordered life. And lately you have become a
disruption in the family," she said firmly. "What exactly is it, would
you mind telling me?"
"What. What do you mean!?" Tim added without a clue as to where the
conversation was going.
"Do you want to be a woman? Is that it? Or are you just some kind of
mincing, preening sissy?" she said as she looked directly at him
unblinking for the moment. He could sense her anger then stammered to
find an answer. "Sickening!" she said as she looked him over. She then
got up from the couch. "Follow me Timothy," she said as she began
moving through the living room.
Tim was forced to follow her. He walked along behind her as she minced
down a hallway and entered the large kitchen. She then moved to a large
white door Tim knew to be the servant's quarters, the room that Lindsay
had lived in for years. Madge opened the door and entered, Tim
followed.
He'd only caught a glimpse or two of these quarters just off the
kitchen. But he could tell Madge had made a few changes. The room was
feminine now, very feminine like an elegant woman's boudoir all done up
in pink pastels and white French provincial furniture. The lace trimmed
curtains on the windows, pictures of flowers and such on the walls and a
large four poster bed with a lace trimmed canopy. And then he saw it,
right there on the bed. It was his large black suitcase, the one he'd
kept in the garage!
He felt faint as the color ran out of his face as Madge went to the bed,
unzipped the case and began rummaging through it. "Sickening," she said
in a simmering tone. "A pathetic, unorganized collection, cheap
clothing, cheap makeup and I can smell the cheap perfume too," she said
as she stuffed everything back into the case and flipped the cover back
onto the case without re-zipping it. "Come with me," she said as she
left the maid's suite and returned to the kitchen. She then opened a
briefcase at the kitchen table and took out a stack of printed papers.
"Go ahead, have a look princess, it's all there!" He could hear the
disgust in her voice as he took a seat at the table joining her. And
then he began looking through the papers.
His mind reeled! Madge not only had his suitcase but now she knew it
all. The transcripts of several chats he'd made, the printouts of
clothing and lingerie sites, sissy sites, cross dressing sites, and
printouts of several pictures from his picture files. Everything coming
from his personal computer in his upstairs office at home. Cindy had
gotten his password somehow and had printed all this stuff out in
addition to giving her mother the suitcase! There was no way to explain
or cajole his way out of this situation, Madge Greystone now knew it
all. She then reached into her leather briefcase and took out some long
legal papers that looked like contracts.
"I want you to sign here, here and here and initial there," she said
pointing to each entry with emotionless efficiency as she paged through
the legal papers.
"What, what are these papers Ms. Greystone!?" Tim gasped as he began to
wade through the pages of legalese.
"Why, they're divorce papers of course!" she replied.
"D...Divorce papers!?" Tim gasped. He gasped again when he returned to
the title of the document and actually saw the words "Bill of
Divorcement," but Madge only continued. She produced an expensive pen,
opened it and set it on the contract.
Tim tried to hedge, to explain but it was all over now. His secret was
out, Cindy knew it all now and now, so did his mother-in-law! "Get busy
Timothy. Sign those papers, it's all been arranged," Madge said with a
tone of finality. She prodded him until he actually began signing the
papers and adding his initials, he then noticed that his wife Cindy had
already signed the same papers. Madge then signed as a witness and then
stamped it with a notary seal she produced from her briefcase. That was
it, it was now final. No argument, no discussion.
He felt like he'd been cut adrift. Years, decades of thoughts now
swirled through his mind as he swooned sitting there at the table as
Madge took away the pen and folded up the contract and put it back into
her briefcase. He'd had a pretty good life thanks mostly to Cindy and
of course Madge, sole owner and matriarch of "Greystone Corporations
Limited."
In the space of only a few seconds his mind raced at light speed as he
sat in the quiet kitchen at the kitchen table, the only sound was the
faint ticking of a wall clock as it marked the passing seconds. He
remembered the arguments about not wanting to have children, a sticking
point in the relationship. And how he'd been a writer when he and Cindy
had met. She'd gotten him in at a small publishing company her mother
owned and had gotten him agency representation. He'd made some good
money in selling two novels that became minor hits but the new stories
over the past four years didn't sell, his talent seemingly had run its
course.
He'd put most of his money into the new house, Cindy put up the rest
with help from her mother and while he toiled as a writer he lived off a
meager monthly allowance from his residuals. But it wasn't long until
those ran dry and he became dependent on Cindy. Of course he did the
cooking and the cleaning and the washing and housework and yard work but
he kept writing. Cindy had moved up to manage the small publishing
company as one of the lead editors and helped to oversee the art
department responsible for book cover art as well. They were getting by
well but with the black suitcase and his computer files now well looked
through by both Cindy and her mother he knew he was between a rock and a
hard place!
He thought of moving on, but where could he work? What could he do? He
couldn't survive on a minimum wage job. Where would he live? And how
would he get around? The nice late model Mercedes he drove was in
Madge's name, he didn't own it. All he had were a few nick-knacks,
mementos and things in his office, his computer and a small dresser and
closet for his clothes, that was it. And now, he'd signed his divorce
papers. Timothy was on his own.
He forfeited his portion of his home in the divorce. And, of course
Madge was taking back the car. It was to be sold on consignment. His
credit cards? Gone. His bank account which contained a grand total of
fifteen-hundred dollars was now the sum total of his net worth. For a
moment he pictured himself thumbing for a ride as he walked along a busy
highway, a duffel bag hanging over his shoulder. His mind raced as the
panic set in!
"Well, I guess there's no fixing things now," Tim gasped in desperation
and resignation. "I guess I'll just have to find a way into town, maybe
a friend can put me up until I get back on my feet," He said to Madge.
"I really doubt you have any friends left dear," she said with a slight
smile.
"What does that mean?" Tim returned.
"It seems that Cindy has explained to your friends, the unfortunate
circumstances. Her poor husband finally admitting that he was
Transgendered. The childless marriage, the division, the mutual
decision to divorce and part company," Madge spoke filling Tim in, all
the bases covered now. No wonder that his few friends didn't stop by or
call anymore.
"Trans...transgendered!? I...I"m not that!" Tim gasped in retort.
"Well, you certainly aren't much of a man now are you Timothy? Hummm?
What kind of a man wears women's things?" She added as Tim shrunk in
his chair.
"Well, what am I to do? I don't have any money to speak of, my house is
gone and now my car? And you and Cindy have taken care of any friends I
had," He gasped.
"It's all been taken care of. You're not being kicked out onto the
street. You were my son-in-law for many years, I'm not that heartless,"
She assured. "If you agree to a few conditions I will allow you to stay
on here, with me."
"Doing what?" Tim returned not knowing what to think.
"Why, helping around the house of course. I did mention discharging
Lindsay didn't I? As I said, I've made arrangements, things are taken
care of. We'll all make a fresh start and put our lives back in balance
and move on from there," Madge said.
Madge realized that Tim now did most all the work at home in between his
writing work. She chuckled when she mentioned that it was he who was
actually the housewife in the relationship. And that he probably,
secretly relished the position.
Once Cindy made her decision she informed her mother. That had happened
within days of Cindy discovering Tim's large black suitcase in the
garage. The next six weeks, that coolness in the relationship was far
more than just a period of thought. Madge had gone to work. After
reading all the files Cindy had brought over and after studying Tim's
"condition" she made a few changes by dismissing housekeeper Lindsay.
She then had the maid's quarters completely redone into the boudoir that
Tim had just seen. But that was just the beginning. Madge then walked
Tim back into the maid's room, the boudoir suite!
"Your duties won't be that difficult. There's a schedule of duties
you'll soon get used to. Mostly some light housework and some basic
cooking and such. If I need major cleaning done I'll contract that work
out, as well as catering should I host a dinner. Your main duties are
to keep house and assist me," Madge said.
"What about all my other stuff at home?" Tim asked.
"It's being taken care of. Cindy will pack your things and donate them
to Goodwill," Madge said as a matter-of-fact. "Go ahead, get out of
your clothes. You'll need a proper bath before bed."
She made him start undressing, right there in the middle of the boudoir
bedroom! She returned from the closet with a long ladies robe in lace
trimmed pink nylon and a matching pair of ladies slippers. Tim set his
men's clothes on the bed, his men's shoes on the floor in front of the
feminine bed. Madge handed him the robe and slippers and as he slid
into the robe and tied the sash he watched as Madge folded all of his
men's clothing and put them into the large black suitcase. After
fitting his shoes into the case she pushed the lid down tight and zipped
the case shut.
"Take this suitcase out and set it by the car in the garage," she
instructed.
"What for?" Tim returned.
"I'll have my driver drop it off at Goodwill in the morning. You won't
be needing it anymore," Madge said with certainty.
"Where are my quarters then?" He asked, looking around. He then went to
the closet and opened the large doors looking for a butler's uniform of
some kind but instead found rows of dresses, skirts, blouses and gowns.
High heels lined the floor and to the right, at the front of the closet
he saw the black patent leather oxford court shoes, six pair, lace up
shoes with a full five inch stiletto heel. And hanging directly above
the shoes? Six proper maids uniforms. All long sleeved with buttoned
white cuffs, the dresses all mid calf length and done up in a crisp and
shiny black acetate satin, tailor made, including the crisp starched
white cotton full bib ladies aprons!
Before Tim could recover his thoughts Madge informed him that these were
his new quarters!
Tim choked a dry swallow as his head spun! Madge noticed him blushing.
"Now now, none of that. We both know what you are. You might even
enjoy it, isn't that right? What was it. Oh yes, you always fancied
yourself mincing about the house looking like June Cleaver isn't that
right? A prim and proper, vintage housewife? That may take some time
to accomplish, but it's possible," She giggled as she led him out of the
bedroom with him lugging his heavy black suitcase. After placing the
case in the garage by the car she then led him into the basement, into
the laundry room. And to the side of the laundry room was a small but
complete home hair salon!
"W...what are you going to do M...Madge!?" he gasped as he clutched his
pink robe and pulled away.
"Ms. Greystone. Remember what I told you? From now on you will address
me as Ms. Greystone," she said as she moved him into the room. "You
didn't know I used to be a hairstylist did you. But first you'll need a
good scrubbing." And with that she entered a small room off the salon
and started a hot bubble bath. She also brought out a large bottle of
Nair depilatory and a pair of white latex gloves as Tim looked on in
disbelief!
Tim felt himself swoon again. "I...I'm s...sorry about all that
happened. I didn't hurt anybody." he insisted. "I...I think, maybe
that I should just put my clothes back on and just leave in the morning
Ms. Greystone. I'll just move away, I'll find a job somewhere," He
gasped but Madge only continued by swirling her hand in the bath water,
making sure it wasn't too hot.
"We've gone to a great deal of effort to make these arrangements. I pay
my maid-servant well, however, you'll have several months of work to
repay me for the expense in getting your new wardrobe ready, and your
new quarters. But, I'm sure you'll come right along in no time. And
soon, your new position and lifestyle will become second nature," She
assured as she had him step into the scented bubble bath. "After all,
how could a weak example of a man like you ever get by alone. You're
too used to a life of luxury. It would be such a shame to see you have
to thumb a ride back to the mid-west and to end up stocking shelves at
Wal-mart, or working at McDonalds. Imagine the dingy apartment you'd
have to live in, the threadbare furniture, the poor meals and never
having any money to go anywhere or do anything, nothing but endless
drudgery. Tragic. Is my offer really that bad Timothy dear? Hummm?"
She finished in a lilting feminine tone as she tossed his shoulder
length hair with her fingers.
He mentioned his hesitation, his embarrassment, the fact that now Cindy
and Madge knew all about him now, but Madge continued. "I've spent the
past month putting things together, and I've spent the past month
studying your "condition," I know exactly who you are and more
importantly, what you are," Madge had once been married but her husband
had passed away before Tim and Cindy had gotten married. Turns out that
it was Madge who ran the empire, Madge who kept things running at peak
performance and peak return. She relished working on a project. And
now, Timothy was her new project! She went about the salon getting
things ready then returned to the bath and had Tim stand in the tub as
she put the white latex gloves on and opened the large bottle of Nair
hair remover!
After she'd slathered his body from the eyebrows down, leaving only a
little heart shaped trim below she had him stand until the stinging pink
gel did it's work. Then wiping him down with a washcloth he watched as
his body hair swirled down the drain. His sparse and fine body hair was
gone now, he was totally smooth, pink skinned and hairless!
Dried and back in his pink robe and slippers he felt the coolness of the
pink plastic salon cape as Madge clipped it snugly around his neck. She
then tilted the chair and washed his hair. She then added a lightener
until his brown hair was a lighter honey blonde. After toweling his
hair damp-dry she quickly styled it using a scissors and didn't stop
until it was in a feminine, ladies hairstyle. After a rinse she toweled
his hair again and added a strong perm solution, then, after gathering
sections of hair she began putting him in curlers. She worked quickly
as Tim's head spun. He'd never worn curlers and now, here he was,
totally smooth, smelling of a floral scent and having his hair done in a
ladies hair style! A pink hairnet followed and then she put him under
the dryer. While his hair dried Madge returned from the counter with a
piercing gun and quickly pierced his ears, little pearl earrings were
now affixed to his newly pierced lobes!
A pedicure followed, leaving his toenails trim and smooth and shaped and
with two coats of bright gloss red and one coat of clear gloss. After
checking his hair Madge then gave Tim a manicure. She then glued on
long salon nails that went a half-an-inch beyond his finger tips. Soon,
all ten fingernails were painted in the same high gloss bright red as
his toenails! As his nails dried Madge then wheeled away the hair
drier. She then removed the curlers and began styling Tim's hair.
Working with a comb, a pick and a brush she expertly worked and teased
the tightly permed tresses into a classic vintage 50's ladies hairdo.
She added hair spray as she worked and continued until Tim's hair was
styled into something that couldn't possibly be combed out to resemble
anything male. Madge finished with more hair spray until the curls were
lacquered tight! Since it was getting late she put a pink satin bonnet
over his new hair set for the night and told him that she'd do his
makeup in the morning. With that, she removed the pink salon cape.
Then after slipping back into his pink slippers she led him back to his
new bedroom.
It was more than just a small servant's quarters. It had a large full
bedroom and a study, lounging living room area and a full bath, and all
was tucked in just off the kitchen and didn't involve any of the rest of
the large two story home. Then while Tim's thoughts were still swirling
Madge handed him a pair of pink stiletto heeled Marabou slippers and a
short, layered, frilly pink nylon chiffon baby doll nightgown and
matching pink panties. He was just stepping into them as Madge pulled
the covers down on the bed with a zipping swish to reveal white satin
sheets! Mentioning that there was a lot to accomplish in the morning
Madge left the room switching off the lights before she closed the door
behind her.
Tim reached under the lace trimmed lamp shade and switched off the
little light on the white night stand then laid back in bed feeling his
tight curled and hair sprayed hair set as it crunched against the satin
pillow. He could feel the hair, the earrings in his newly pierced ears
and feel his totally smooth skin and he could smell the floral scent in
the air. His head spun at all that had happened in such a short time
since earlier that evening. Exhausted, he finally drifted off to a
troubled sleep.
"Get up Timothy, we've lots to do today," Were Madge's words that awoke
Tim early the next morning. He felt the slippery swish of the satin
sheets and his nightgown as he moved in the bed. Madge was already at
the dresser, he watched as she gathered a pair of sheer nylon hose.
"Let's get ready shall we?" she said as she led him to the attached full
bath as he teetered and wobbled on the high stiletto heeled slippers.
Madge had Tim take hold of the bathroom counter and then lean over. He
pulled away as she began rubbing the front of his panties! "M...Madge!
I...I mean Ms. Gladstone! Wha...what are you d...doing!?" He gasped as
she rubbed the front of his pink nylon panties with her hand covered in
the sheer nylon of the stocking. She sensed his nervousness but was
firm, pushing him back over the sink. Soon, she worked him into an
erection. Then quickly, she pulled down the front of the panties then
produced a latex condom and put it on him. She then worked one stocking
over his erection and then he felt the slippery sensation as the second
sheer stocking was pulled into place. Madge then began pulling gently
working the second stocking over the first and then picking up speed
until the familiar nylon zip could be heard! Tim grunted and then
gasped at the nearly overwhelming sensation as Madge chuckled with
satisfaction over her new knowledge and control of her former son-in-
law. He gasped again as he wobbled tip toed on the high stiletto
slippers as she worked in and out, in and out, the near frictionless
nylon zipping with each stroke.
"Mmmmm. Yes. Feels so good doesn't it precious?" she cooed excitedly.
"Yes, so nice and feminine, and so nice and silky. Feels delicious
doesn't it princess?" She coaxed. Until finally Tim became weak at the
knees he teetered on the high stiletto heels yet again then grunted as
his hips thrust forward. Madge stroked his erection harder and faster
now, until finally she held him tight then with satisfaction felt him
twitching as he ejaculated into the reservoir tip of the condom. Tim's
head was spinning as Madge took the stockings away to soak in the sink.
She then carefully removed the condom and poured the contents into a
small glass tube.
Madge was at the dresser going through the drawers, each one filled with
a certain type of ladies vintage lingerie. The closet was already open,
she'd selected a proper black satin maid's uniform and a full white
apron. Tim's head spun at seeing all the women's clothing. Just then
the intercom in the kitchen rang. Madge left the room as Tim milled
about, befuddled. He became embarrassed as Madge escorted the lady
doctor into the room. It seemed that this was a house call! Judy
Wilton M.D. was similar in age to Madge and was also one of her friends
but it didn't help Tim. The lady doctor entered the feminine bedroom
and smiled with a slight smirk at seeing Tim. He was told he'd be given
a quick looking over. Madge handed the doctor the little glass tube
containing Tim's ejaculate which she put in her doctor's bag. She then
took out a stethoscope and began looking Tim over. She checked his
temperature, checked his eyes, ears and throat and then she produced two
pre-loaded syringes! Before Tim could complain or resist the doctor
swabbed the area on his right hip and quickly gave him two injections.
She then handed Madge a large bottle of pills. Apparently for a new
daily "vitamin" regimen.
The doctor was soon finished but before she left she handed Madge some
more of those injectable medications. Madge then escorted the lady to
the front door. She then returned to the bedroom with a small glass of
water and one of the pink pills and made sure Tim swallowed it down.
With that out of the way the dressing for the day began in earnest.
"What are those!?" Tim gasped as he watched Madge put the large silicone
breast forms into the pockets of a sturdy, new mastectomy brassiere.
"These are breast forms. You'll need them to fill out your dresses and
blouses," she said as she worked.
Madge had Tim slip into a pair of white, lace trimmed ladies nylon
briefs. She then approached with the brassiere and slipped the wide
satin straps over Tim's shoulders. She quickly hooked the four back
hooks and adjusted the straps for a perfect fit. She then began
gathering the appropriate lingerie. Tim immediately felt the weight of
the forms and the pull of the brassiere straps. The sensation caused
him to gasp slightly as he'd never worn proper forms before.
Tim's head spun at the realization of what was happening as Madge
rummaged through the dresser drawers selecting various pieces of
lingerie and putting them on the bed. His mind was still in turmoil.
Within the space of barely a day he'd become divorced, lost his house,
lost his car, all his clothing and personal effects at his home were
being packed up and being hauled off for donation to a thrift shop.
Even the clothes he arrived in were now packed up with the ladies
clothes that were in his suitcase, a suitcase that would soon be at a
thrift shop as well. And then the make over, the vintage hair set, the
manicure and pedicure, the pierced earrings. Then, after spending the
night in a feminine boudoir came a quick medical physical. No money, no
job, no future to speak of. Tim knew he'd have to put up with this
situation until he could find a way out. But for now, the chances of
that were bleak. Before his thoughts could clear, Madge quickly began
dressing him.
Tim gasped at seeing all the lingerie on the bed. He'd dressed before,
he had tried vintage stockings and foundation garments before and had
dressed completely but he quickly realized as Madge dressed him that
this was far more involved than anything he'd ever done before. Madge
had made detailed plans, this wasn't any lark, or just playing "dress
up" for fun or even fetish, this was serious, far more involved than he
realized.
The only sound in the quiet boudoir now was the sounds of the clothing,
the sound of hooks and clasps and zippers, the fabrics, the nylon, the
satin, the taffeta that swished, rustled and zipped as Madge supervised
Tim's new look. He was soon dressed fully in lingerie, the ladies nylon
briefs, the sturdy mastectomy brassiere, a pair of nude support
pantyhose. Before working the pantyhose up and smoothing them into
place Madge had had Tim bend at the waist. She worked the panties down
then from behind she fumbled at his now hairless manhood.
Tim winced at first as she fumbled with his testes, he grunted slightly
as she quickly pulled his manhood back tightly between his smooth shaven
legs and then pressed the testes, working them up into his body cavity
until they were up tight like ovaries. The briefs and pantyhose were
then pulled up high and tight then smoothed into place.
A sturdy paneled fan-laced panty girdle came next. Madge then gathered
a pair of neutral grey nylon stockings and began rolling one of them up.
She put it on Tim's smooth right leg and quickly worked and smoothed it
up and then gartered it tightly. The left leg was next. She then
pulled the girdle all the way up high on Tim's waist then pulled the
straps on each side. The white silk laces zipped and whirred through
the stainless steel eyelets at the back of the sturdy white paneled
girdle, another zipping pull and Tim's waist and hips started taking on
a more feminine shape. Another stiff pull and Madge quickly hooked the
straps down holding the lacings tight. The nylon stockings now tightly
gartered high on his thighs, the filmy grey material gleaming in the
light. A white nylon spandex waist cincher was fitted around his waist
next and quickly clipped into place. It wasn't tight, but he felt the
difference and the shaping effect the snug fit had on his slender frame.
Madge then swished a long, lace trimmed, waltz length white nylon slip
from the bed and began gathering it. She slipped it over Tim's head,
worked his arms through the satin straps then after fitting the lace
trimmed cups of the slip over his bra and weighted silicone forms she
smoothed the slip down over his trim waist then let the wide sweep of
the full slip swirl down to its full length at mid calf length.
Tim heard the loud crisp swish of another white slip. He recognized it
as a long half slip but this wasn't a standard half slip. Madge had him
step into it and was soon swishing it up to his waist where she quickly
tied the white taffeta straps into a tight bow at the back. The taffeta
garment was a classic petticoat, not an overly frilly one, just one to
give the skirt of a dress a bit more shape and volume and to give that
added silken sound. As Madge went to the open closet to gather the rest
of Tim's outfit he gasped at seeing the crisp white taffeta petticoat,
he noticed the wide four inch flounce at the bottom of the garment and
heard the loud zipping, swishing sound as he moved. Then he heard
another zipping sound!
Madge unzipped the long back zipper on the black satin dress as she
approached. She set the long full apron on the bed then handed him a
pair of the black patent leather stiletto heeled lace up oxford shoes
he'd seen the night before. "Take a seat at your vanity and put these
on," she said without emotion. Tim did as he was asked but then a
question arose as soon as he put on the first shoe and found it a
perfect fit. "These, these clothes all seem to fit!" He gasped. "Of
course they fit!" Madge returned. "All of your new clothing is in your
size!"
He wobbled and teetered on the high stiletto heels as Madge gathered the
bulky black satin dress. She had him put his arms into the long sleeves
then worked the dress down, the satin sliding easily against the silky
nylon under slips. Madge pulled and smoothed until finally, the wide
skirt of the dress fluttered down to mid-calf length with a loud satin
swish. Tim next heard the whirr of the long back zipper then felt the
dress pulling tight around him. The bib apron was next. Madge put his
arms through the white shoulder straps, criss-crossed them at the back
then after fluffing the long apron out she tied the wide starched cotton
sashes into a tight and feminine bow at the back. After buttoning the
white satin buttons at the crisp white satin cuffs at Tim's wrists she
fixed the collar on the dress. After smoothing everything out Madge
stood back and had a look. Satisfied with her work thus far she had Tim
take a seat back at his vanity.
She removed his new pierced pearl earrings and swabbed the lobes with an
alcohol swab and then replaced the studs in each ear. She then went to
work on his eyebrows with a tweezer and a bit of waxed tape and didn't
stop until Tim's brows were shaped into a high and feminine arch. She
then began his makeup regimen. "I'll be doing your hair and makeup in
the mornings but you'll be expected to soon be able to do this on your
own, so pay attention," Madge said as she began her instruction.
Tim gasped at his look in the vanity mirror. He could see the dress and
apron he was now wearing, he could see the tightly curled hair set and
the earrings Madge had done him up with the night before and now he felt
the cold, creamy flesh colored foundation that Madge began to apply to
his face.
He wasn't listening to her words as she worked. He felt his stomach
tighten and his head begin to spin. This was far, far more dressing up
than he'd ever done before. He never really did his hair and his
attempt at makeup was mediocre at best and he never used nail polish
because of being discovered by Cindy, but now, as he looked at his long,
gloss red salon nails he felt himself being pulled, pulled away from his
masculinity as Madge continued on pulling him deeper and deeper into her
plan and deeper into femininity than he'd ever been before!
He could still feel the mask like foundation on his face as Madge began
gluing the false eyelashes into place with a sturdy long lasting glue.
He heard the part about having to reapply them only once a week or so.
He looked into the lighted vanity mirror to see how smooth and uniform
his facial skin tone was now, and the shade was lighter too, almost
porcelain in appearance! His appearance was never considered rugged, or
even very masculine but now, those features were quickly being replaced
by feminine ones.
Black liquid eyeliner came next, and then Madge brushed in the mascara
that blended his lashes with the false ones. A powder blue eyeshadow
came next, a "vintage look" Madge explained as she dusted his lids fully
and then added a darker shade of blue at the edges making his eyes
appear larger and more pronounced. This wasn't any rudimentary exercise
in makeup application. Madge had a similar look but not quite as
pronounced, and, as she'd been applying her own makeup, the decades of
experience she had, she was now applying to Timothy!
Madge then began lining Tim's lips with a lip pencil. This was followed
up by a matching bright red, long lasting lipstick that matched his nail
color. Tim's head spun and his long eyelashes fluttered as Madge
applied the creamy red lipstick to his pouting lips in broad heavy
strokes. She finished by dabbing his lips with a tissue.
A blusher came next, a strong powdered rouge that added to the classic,
vintage look of the proper lady, the proper "housewife" of the 1950's.
Smiling at her accomplishment, Madge put the brush down and began with a
finishing powder to set the look. She finished up with a liberal amount
of a strong floral perfume. Tim's eyes burned slightly causing him to
blink and he coughed a bit as the perfume encircled his head.
Almost finished, Madge picked up a brush and comb once again, to tighten
and freshen Tim's ladylike vintage hair set that had been tussled a bit
from a sleepless night. Soon his curls were once again lacquered tight.
She then pinned a small black satin bow to the right side of his head,
the black color giving quite a contrast to his now blonde hair. Without
ceremony Madge finished by clipping a real pearl necklace around his
neck. The white pearls felt cool against the hairless skin of his upper
chest.
And that was the morning routine, a strict hour of getting into prim and
proper ladylike shape that would be expected each and every day! Madge
then led Tim out of the room to start his day. He heard the sharp click
of his stiletto heeled shoes echoing in the kitchen as he minced along.
He also heard the glassy, crisp swish of the wide black satin skirt and
the stiff, white flounced taffeta petticoats underneath.
"Keep your legs together as you walk. Short steps and move from the
hips, I want to hear your nylon stockings too. I want to hear them zip.
You must remember, don't you darling? That 'shick-shick-shick' sound?"
she said with a chuckling smile as she led Tim out of the kitchen and
into the dining room. "You already know the layout of the house but to
get a proper start we'll begin upstairs. She then had him mincing
across the large living room and up to the second and top floor.
They toured the four bedrooms upstairs, the master suite done up to
Madge's taste. The master suit contained a large bath and there were
two others just off the wide hallway. She pointed out the flowers on
two of the tables along the hallway and pointed out a painting or two
that would need dusting as well. Then came the living room, the dining
room again with a stop at the large dish and silverware cabinet he'd
need to learn about. And then the kitchen, where everything was. And
then the garage, where the garbage bin was and finally the basement,
laundry room and storage areas. The whole tour taking place while Tim,
now totally dressed as a vintage housemaid minced and wiggled along side
his former mother-in-law!
She showed him how she liked her morning coffee made. They took a break
in the kitchen but the instruction continued. How to walk, how to sit,
how to gesture, how to speak softly, how to move as a proper lady.
Tim's head spun with all the details! But of course the new job
wouldn't hit him full force, he'd be able to work into the job. But,
within a weeks time she assured Tim that he would indeed be up to speed.
Meanwhile he'd continue on wearing only women's things, doing only
women's things. As far as Madge was concerned his days living as a man
were now over! Aside from breaking in her new "maid" in, Madge was
content that Timothy, was now well on his way.
Although Madge often smiled with satisfaction at seeing Tim as the new
housemaid and how he was taking to his new feminine lifestyle and new
job, she checked her smirks and her vindictive thoughts at how easily
and completely she had taken control over him. But the sensation to her
was exquisite. Timothy after all was getting just what he deserved.
But, there wasn't any laughter from Madge directed at Tim. No jibes, no
insults as to how he now looked and dressed and the type of work he was
now doing, it was just business as usual.
It was a much larger house but as Madge had mentioned the night before,
that was really the only difference. Tim had already done all the
cooking, washing, cleaning and general housekeeping as his former house
anyway, now though, he was just in a different place. The only
remaining detail? Madge determined that since his last few books had
failed miserably, it would probably be best if he just faded away as Tim
Benson author. It wasn't long until Madge's instruction on duties, the
notes and corrections faded away as well as Tim began to overcome the
learning curve and settle into his new position. He soon got used to
being addressed as "Tiffany," since it was now obvious with his new look
and new station in life that the name Timothy was simply out of place, a
male leftover no longer needed or for that matter tolerated. Madge was
intent in her all encompassing plan. Soon, the problems that had been
discovered soon went away and her once well ordered life was back on
track just as it had always been.
Two weeks passed and then another two. Madge kept watch on Tim in his
looks, and in his performance in his duties. She also kept up the
instruction, her version of "charm-school" for her wayward former son-
in-law. She still did his hair, the strict wash and permed vintage hair
set he was expected to have daily but he was learning to keep his hair
nice by himself between sets. The hair set was standard and uniform
from day to week, but the makeup, Tim's new feminine look from day to
day that was standard as well was a bit trickier to master. The many
steps in putting on proper makeup took a bit longer to master but
finally he was able to get a look every bit as flawless as Madge was
able to accomplish. He was soon dressing himself daily now as well. He
was able to dress in his proper maid attire for his job but Madge would
often select a nice day dress or something for the evening from his
extensive wardrobe. She was always available to help with lacing
corsets when she felt one was called for. And all the while the two
shots Tim understood to be vitamin shots continued on twice monthly, and
the pink "vitamin" pill she made sure he took daily continued on as
well. So did the regimen of the thrice weekly milkings at the bathroom
sink!
The previous days worn stockings would be used by Madge on those
mornings. Tim would teeter on the high pink stiletto slippers as Madge
would reach under the lace trim of his vintage layered nylon chiffon
baby doll nightie, lower his panties then after sliding the slippery
nylon hose over his erection she'd work him into a gasping frenzy as he
held tight to the bathroom counter. Sometimes she'd use a condom and
then save the "specimen" to give to her lady doctor friend, otherwise
the ejaculate would end up in the sheer stocking toes, the stockings
deposited in the sink to be soaked in Woolite later and then rinsed and
washed with his other lingerie.
It wasn't long until Tim's "vitamin" therapy and the strict tucking
program Madge had decided on was starting to have an effect. Unknown to
Tim, this was her way to gauge her progress. She found she was having
to stifle her giggles on those three mornings a week because as much
excitement as Tim had gotten from dressing feminine and even with the
slippery feel of sheer nylon stockings over his member she was now
having trouble working him to a full erection! And the constant tucking
of his testes into his warmer body cavity was having an effect as well.
Madge had gotten reports from her lady doctor friend who was keeping
track of Tim's physical condition. Madge's regimen showed that Tim's
sperm count was now in steep decline! She began to relish those morning
workouts. Smiling with satisfaction as he struggled to gain an
erection. The erections were only half as strong as they had been now,
and the copious, thick creamy ejaculate was now quite lessened, the
discharge now weak and cloudy, watery! Madge noticed how much more
luxurious the hair on his head had become, thicker too now. She noticed
how smooth Tim's skin was becoming, how his trim waist looked even
trimmer, his hips ever so slightly wider and rounder. But his breasts,
they were beginning to bud nicely! Tim had complained about a tingling
and a soreness but Madge had said it might be a reaction to the latex in
his breast forms. That would buy her time to continue her therapy but
she knew Tim wasn't stupid. He'd soon figure out what was going on!
Three weeks later he finally confronted her about his still budding
breasts. The areolae were much larger now, there was pronounced nipple
growth, and as the breasts continued growing outward they now began to
widen and take on weight!
Madge was in Timothy's boudoir room putting his hair up for the night
when the urgent complaint came. Her reply? "No. Its no reaction to
the silicone breast forms," She stated then continued. "You're a big
boy, or at least you were," She then added, chuckling with satisfaction
at her accomplishment. "What did you expect Timothy!? I've had you on
the female hormone estrogen since the day you arrived! Those pink pills
you take every morning are female hormones. And those 'vitamin'
injections? A stronger hormone dosage and another drug to shut down
your little testes, to stop any male production of testosterone."
Tim's head spun, he swooned as he sat at the vanity. "It can still all
be undone at this point. But you needed to be brought more in line with
your new self. Haven't you noticed your thoughts changing, I've noticed
your emotions becoming more feminine in nature too. We're going to get
your mind-right," she said with satisfaction.
"I...I d...don't want to t...take anymore of that stuff, Ms. Greystone!"
Tim gasped.
"And if we continue on a while longer you'll soon only have female
hormones in your system and you'll continue to develop more and more
feminine traits," she added.
"I d...don't want, want that!?" he gasped in panic as he choked a dry
swallow.
"What did you think, that this was all a joke, a game!?" she said
angrily. "Don't you recall why you're here? Do you remember the first
conversation we had the evening you arrived? You disrupted this family,
quite severely. I had to take measures to avoid a scandal, measures to
restore our well ordered lives. And I've done that. You'll continue in
your position here and do as you're told!"
"But I've d...done everything you've asked Ms. Greystone!" He said with
a tremble in his voice as he felt the full weight and panic of his new
lifestyle, a lifestyle Madge was pulling him deeper and deeper into!
His head spun with the realization that if he didn't get out of this
predicament soon there may be no escape!
"I've only given you what you like, what you apparently need, isn't that
right Timothy? Sickening! My son-in-law, unemployed, doing housework
like a regular housewife and trying to write books instead of finding a
real job. And then, while my daughter is hard at work there you are,
all dressed up as a woman at home behind closed doors, mincing and
preening as you enjoy your feminine attire. Well, how do you like it
now 'Tiffany,' hummm? she said with a lilt in her voice as she finished
his hair and more roughly than usual put the pink satin bonnet over his
hair set for the night. "Do you feel ladylike now? Do you feel
feminine!?" She relished the sensation of her power and control over
her once errant son-in-law, now fully conditioned, trained and turned
into a docile and proper housemaid.
"The expense I've gone through, the time and effort. Redoing your
servant's quarters, collecting an entire wardrobe of the expensive
vintage women's clothing and lingerie and the hosiery you adore took
quite an effort just to enable you to look and feel like the proper
'June Cleaver' lady of the house you've always wanted to be. But then
again, cross-dressing swishes like you only dress up from time to time,
depending on how strong your affliction is, isn't that right princess?
Yeah, I am quite well read on your condition now. Dressing up in all
your silky things and then doing your disgusting practice, and then
afterwards you have to undress quickly don't you? Put all your feminine
finery away, to get it out of sight because afterwards all those silky
things become too much if you stay dressed too long. After your release
you have no need for your feminine things, that is, until the urge
returns, and it always does doesn't it sissy? And then meanwhile, you
wait until all the guilt and embarrassment subsides as you return to
your pathetic so called 'male' life. Isn't that right? It's your male
side that's the phony, the true lie, isn't it princess?" she said
hammering home her plan, her intention. "The unfortunate discovery of
my son-in-law was tragic to say the least.
I decided to inform what few friends you have that my poor son-in-law
was battling his conscience over his inner transgendered self. Cindy
mentioned the divorce, and then finding another man so she can finally
have the children she always wanted. I arranged the divorce and
arranged you to take over Lindsay's former job as my full time live in
housekeeper. That took you out of the picture and put you under my
control where I could work with you personally. So, do you enjoy your
new job and your new lifestyle princess? Do you finally feel feminine?
Because if you don't feel feminine yet you soon will!"
"I...I'm leaving! I d...don't want to, to do this anymore! You can't
keep me here, you can't force me!" Tim stammered as he squirmed on his
white satin covered vanity chair.
"That's true, it's always been true," Madge said as she turned to pace
the room in thought. "Well, I guess after a good nights sleep you're
free to go then."
"Just like that?" Tim gasped.
"Just like that," Madge returned. She then walked over and opened the
walk in closet and looked inside. "What dress would you like to wear
when you leave in the morning?" she asked casually as she then moved to
the dresser and opened several drawers brimming with ladies hosiery,
slips, teddies, panties, bras and girdles. She then went back to the
closet and returned with a vintage outfit, a long sleeve mauve ladies
skirt suit. She also gathered matching pumps with five inch heels and a
mid sized ladies vintage purse. She laid everything over the white
chaise lounge in the corner past the foot of the bed. "I'll tell you
what, I'll sweeten the deal since you've been such a good housekeeper.
I'll add one-thousand dollars in cash, I'll put it in your purse. That
way you might be able to find an apartment, well, a small one for a
month if you're lucky," She added, grinding in the painful reality soon
to be in store for Tim! "Well, you'll need more than just one outfit
too. I'll let you use one of my large cases, you can select anything
you want and pack up tonight. Then tomorrow you can walk down to the
gate, press the button and be well on your way. Or, better yet, I'll
have my driver take you. Would you like him to drop you at the airport
or the bus stop, or would you rather search for a job locally?" She
finished with satisfaction standing there looking at Tim in that satin
bonnet and his white satin long gown and matching robe as his head just
spun forcing him to silence.
"I...I want my own clothes back!" he returned still planning to leave.
"Sorry, but the clothes you wore here that first night are long gone
with your suitcase of ladies things. If you leave tomorrow I'm afraid
you'll have to choose from what's in this room because there isn't a
stitch of any male clothing here," She added then smiled as Tim seemed
to shrink in his chair with defeat.
She could see the wheels turning, the gears turning, well grinding now
actually. The window of escape quickly closing right in front of his
eyes. She continued on. "Look at you now? You can shave off the
curls, scrub off the makeup and remove the salon nails but haven't you
noticed your new and feminine demeanor and mannerisms, how you move?
Certainly not manly, not anymore. Your waist is smaller, your hips now
two inches wider than before, and your bust line, well, I'd say that
you're a full "B" cup now, at least. I really doubt you could find any
men's clothes to fit your new shape. Tell me, where will you go? Where
will you work? A waitress maybe? A hotel maid? But oh, there's that
pesky money problem again. Your Mercedes is long gone and that thousand
I offered to give you won't last long. And overall, your look? Well
Tiffany dear, you're very feminine, very ladylike now. You've done so
well but truthfully, if someone looked close enough, even after all the
female hormones and the laser electrolysis they'd still see a hint of
Timothy. That would be so tragic if you were to be caught in a bad
neighborhood, wouldn't it?" she said with a knowing smirk. She then
returned to the vanity.
"I'm still not finished with you Timothy. You're coming along, quite
well actually. But there's still more work to do, still more I have in
mind for you dear. And I admit, you've become a very efficient
housekeeper. I'd much enjoy if you stayed on here with me. You'd be
much more fulfilled here and much safer, don't you agree?" She finished
then waited for an answer she didn't need to hear.
Tim got up stunned and walked almost in a staggering trance back to his
feminine four poster bed for the evening. She'd beaten him, she'd won.
He knew he was too far gone now, no useable education, broke, without a
house, or car, or job or any employment prospects. But, he was safe as
long as he stayed under Madge's kindly influence.
"In the morning why don't you go ahead and put that cute ladies suit I
put out. We need to get a few things done in the morning," she said
with a smile as she left the bedroom, switching off the light as she
closed the door behind her.
The next day Tim was given another physical another round of injections
and was taken to out-patient surgery. The doctor also gave Madge a new
pill prescription. Tim's 'vitamins' were stronger this time. The
remainder of the old pink pills would be discarded, the new pills were
the same estrogen combination but now at full feminine strength!
The ride home in the back of Madge's limousine was both uneventful and
silent. Tim sat in his mauve ladies skirt suit, clutching the purse in
his lap with his white gloved hands as he looked out the window still
feeling the numbing effects of the medication and the tingle of the
stitches in his still hairless but now very empty scrotum! Madge felt
the sense of satisfaction as the driver continued back to her estate.
The paperwork Tim had signed for surgery was completed, as was the
paperwork from the lady doctor stating that Tim was indeed undergoing
"therapy" for his transgendered condition. His records would be amended
now to show him as a female with the new name of Tiffany Benson.
Madge's ongoing work was continuing splendidly!
After a few days recuperation Tiffany was back at "her" job. And time
went on. The elevated rate of female hormones in his system was now
full strength and with a total absence of any more male testosterone the
female hormones continued working unabated. The feminizing results not
only continued but at an even faster pace than before. His facial skin
now totally hairless though laser electrolysis was smooth and uniform.
A few weeks later a bit of work on his nose and cheekbones as well as
redoing his hairline into a more feminine shape really clinched the deal
and made Tim even more convincing as Tiffany.
Madge noticed as she watched Tiffany work. The corseted trim waist, the
short high heeled mincing steps and the swish of the black satin maids
uniform and the rustle of the taffeta petticoats underneath, the flair
of his now womanly hips that accentuated a wiggle and his growing bust
size. Outwardly the bust size remained the same but she'd had to update
Tiffany's bras on a regular basis, shrinking the size of the silicone
forms as his natural breasts grew. Once the hormones had done as much
as they could to accentuate Tim's bust line he was scheduled for another
procedure. After wearing a nondescript sports brassiere for a period of
three weeks Madge finally did away with the silicone forms and the
mastectomy brassieres and after measuring Tim's new size found it was
just a bit larger than his normal look. After a shopping trip one
morning she returned home with a dozen new regular and feminine
brassieres. Tim was soon healed up and back at work, his new augmented
breasts, pendulous now as they jiggled in his brassiere filled out the
front of his maid's uniform nicely. With his fully feminine 40 "DD"
breasts nestled in a white, lace lavished satin brassiere there was no
doubt he now had a fully feminine form.
Madge had worked on Tim's voice, making it softer and more feminine and
working with him to get his inflections right but still wasn't quite
satisfied with his voice that was a bit too husky to match his new
appearance. Another visit to the clinic to work on his vocal chords
soon cured the problem. Tim sipped honey tea and tried not to speak for
the better part of a week after the procedure. Madge worried at first
about the rasp in his voice which at first sounded even rougher than his
original voice. But as the days passed she noticed a definite change as
Tim's voice began to reach a higher register, then started sounding even
slightly more higher pitched until finally he sounded nothing like any
man. His voice was feminine now, melodious and matched his appearance.
Madge was pleased with her new housekeeper Tiffany Benson.
Tim continued on being Madge's prim and proper housekeeper and feminine
companion. It got to the point that even Madge from time to time caught
herself of thinking of Tiffany as only Tiffany. Her world was back in
order now.
They'd often have the driver take them out for coffee and lunch,
shopping trips to the exclusive ladies salons became common place.
Tiffany sometimes even accompanied Madge to her various ladies club
functions as well. Since Tiffany was now fully competent in getting
dressed and made up properly Madge expanded her duties to helping her
dress in the mornings and to offer opinions on her various outfits.
At home Tim, now Tiffany was the vintage "housewife," rigidly feminine
as in days gone by, prim and very proper. But Tim had always remembered
Madge's classic look as well. Not quite as "vintage" but elegant and
always very feminine. He always noticed her breasts in her satin
blouses, the roundness of her hips under a tight, satin lined skirt, the
jewelry she wore. He remembered and still noticed how she carried
herself, how her hair and makeup was always perfect. He remembered her
perfume scent that followed her and the zipping sound her nylon clad
thighs and calves would make under her trim skirts as she minced along.
Even though Tim now looked that way himself as housekeeper Tiffany, and
now that he himself was living such a feminine lifestyle and
experiencing everything as Madge was when he used to notice in his
mother-in-law Madge, although the notice he took these days had been
muted due to his feminine experiences he still took at least a faint
notice in his ex mother-in-law. Yet another facet of his new existence.
It was quite a shock when Madge announced that her daughter, his ex-wife
Cindy was engaged to be remarried! A small dinner was arranged. Madge
decided it would be a catered affair to relieve Tiffany of the chore and
to allow "her" to be a proper dinner guest.
It had been over two years since that night that Tim had gone to the
estate at his mother-in-law's request. Cindy came to visit carrying
several bridal magazines to show her mother. She didn't recognize
Tim/Tiffany at first. So much time had passed that she'd moved on from
him, moved on from their marriage and had started over. Tim was gone
now, their few friends they associated with now only associated with
Cindy and her new boyfriend. Their knowledge of Tim moving away and
having transgendered issues was quietly forgotten. They didn't want
that stigma in their social circles.
Cindy noticed Tim mincing and swishing around the house, arranging
floral displays and dusting and straightening and bringing Madge
afternoon tea and such but it took a prolonged stare to finally realize
her mother's handiwork. She remembered catching him dressed once or
twice early in their marriage but now, the transformation was complete.
At seeing him swishing around with limp wrists and with every male
attribute he ever had now long removed Cindy giggled at the result of
Tim finally getting what he really deserved. The first meeting between
Cindy and housekeeper Tiffany was cool at first. Tim was embarrassed
and befuddled but Cindy had moved well beyond their former relationship.
She wished him well and complimented him on his new look and was glad he
had a position in life but it went little farther than that as Tim
returned to his duties and Cindy took a seat in the living room to go
over the bridal books she'd brought.
About an hour later after Tim had brought afternoon tea and then taken
the tray away when Cindy and Madge were finished he heard giggles and
then loud unrestrained laughter coming from the living room. After
straightening the kitchen Tim minced into the diningroom and listened
in. It seems that Cindy had selected her wedding gown and then the
bridesmaids dresses. All done up in layered knee length pink nylon
chiffon, a vintage style. Madge took notice of seeing Tim dusting the
dining room table and had him take a look at Cindy's choices of outfits.
Tim approved then excused himself to finish his duties for the day. But
then Cindy revealed a turn of events she wanted five bridesmaids but
only had a total of four. Both ladies looked at Tim and giggled. Well,
he was still taller than her other friends, not by much but they decided
it might actually work. Tim could be the bridesmaid on the far left in
the picture, short to tall. Tim's head spun as both ladies chuckled and
giggled. The wedding was still weeks away, it wouldn't take hardly any
effort at all to have Tiffany Benson's name changed to a different last
name. Then there could be no name recognition, and with all of Tim's
procedures Tiffany only had a vague resemblance to Tim. He'd pass as a
bridesmaid quite unnoticed. The afternoon was a greater success than
could have been expected. Tim was recruited and due for a dress fitting
within the week as an exclusive downtown bridal salon. Then on the way
down to the bridal salon Madge made a stop at her attorney's office. It
wasn't much trouble really, just procedure. Tim Benson's name and
identity had been changed from male to a female named Tiffany Benson.
This time the change was far less drastic but it worked flawlessly.
Tiffany would go to the wedding as a bridesmaid in the wedding party.
If the subject came up it would be mentioned that Tiffany was Madge's
housekeeper helping her daughter out at the wedding. And with that the
wedding was scheduled, the programs printed. Tiffany Palmer, would be
one of the official bridesmaids!
When the time finally arrived, Madge took Tim to a salon to have his
hair done especially for the wedding after he'd finished with his dress
alterations. The next day she helped him dress for the wedding. The
layered pink nylon chiffon gown fluttered at Tim's nyloned and smooth
shaven legs as he teetered on his pink stiletto heels. Madge added the
feminine dangle earrings and a pearl necklace that felt cool on his
smooth hairless chest, the scoop neckline of the bridesmaid's dress now
showing his ample cleavage, his ample bust. The well tailored dress was
zipped tight