Date: Wed, 01 Aug 2001 17:55:16 -0700
From: Eugene <eugenewebber@eudoramail.com>
Subject: Deidre's First Day

Title:  Postcards from the Estate // Maids' Service / Deidre's First Day

Deidre's  First  Day

[This postcard is about Deidre, whose wife has signed him up for a weekend
of training as a Restoration chambermaid.]

	As he checked his e-mail, Colin was surprised to find a message for
Deidre, his feminine alter-ego.  The only other person who knew of her was
his wife.  At her insistence, Deidre was kept securely in the closet except
for one or two weekends a month, and then they went several hundred miles
away to towns in which they were not known for Deidre to strut her stuff.
Colin opened the e-mail:
	"Dear Deidre:
	"I have tried throughout our marriage to indulge your need to be a
woman.  Since this need has grown stronger each time Deidre is set free, I
am willing to continue to indulge you only if I can benefit as well.  I
have found a special club which offers guidance to men such as you.  I have
signed you up for a series of weekend sessions.  You will find a brochure
about this club, The Estate, next to the computer.  You have a choice: when
I get home, you must be dressed as Deidre and ready to spend this weekend,
and every weekend, or more, of our lives as Deidre, or, you can send Deidre
away, never to have her as part of our lives again.
	"Love, Sandy."
	Colin was stunned.  He knew his crossdressing was not fully
accepted by his wife, but he did not think it was a threat to their
marriage.  He clicked off the computer and picked up the brochure.  His
heart began racing.  He had never thought such a place existed, or could
exist.  He and Sandy had played everything by ear, learning as they
progressed.  There had been several close calls and dicey situations.  Here
was a place where he not only could be Deidre freely, but they would help
him be the woman he wanted to be.  Choice she said.  Live without Deidre?
He now knew that he would be able to live without Cassandra a lot easier
than he could live without Deidre.  But why not live with both?
	Cassandra was not sure who she would see when she entered her home.
Never comfortable with her husband's needs to act like a woman, she had
gone along as long as the cross-dressing episodes were limited to a couple
of weekends a month, and then only in places far away from their home or
workplaces.  She had come across a wives-of-transvestites chat room on the
internet, and met with Sheila, one of the wives who lived in their home
town.  Sheila had reassured her on many issues, and heightened her anxiety
on others.  But what most impressed Cassandra was how Sheila had turned her
husband Douglas's fetish to her own benefit.
	On Cassandra's first visit to Sheila's comfortable, but definitely
middle-class, home, she was greeted by a uniformed maid.  Throughout that
initial talk, the maid was everpresent.  Sheila never said anything to the
maid, but it took only a look, a raised eyebrow, a flip of the hand or the
flick of a finger and coffee was poured, sandwiches were served, dishes
were removed.  When Cassandra asked where Douglas was, Sheila laughingly
pointed to the maid.  So completely feminine-looking and natural in his
movements was he, that Cassandra thought the maid was a woman.
	In subsequent visits, Cassandra was introduced more fully to
Douglas' alter ego, Gwendolyn, the Edwardian maid.  At a special weekend
stay, Sheila introduced Cassandra to two other wives of transvestites, and
their husband-maids.  The women shared their experiences as wives of
cross-dressers with Cassandra, and informed her of the Maids' Service at
The Estate as the means they had used to come to grips with their husbands'
predilections.  The Estate is a private club for persons whose sexual
preferences are quite exotic.  The Estate offers several services catering
to its members' needs for dominance, submission, variety, multiple
partners, whatever.  Above all else, The Estate offers discretion.
	Convinced that such a relationship was the solution to her
situation with Colin, Cassandra had Sheila arrange a membership for her and
Colin.  At the membership interview, The Estate's representative, Madame
Smith, was very straightforward.  Since Cassandra's membership was
sponsored by Mrs. Nungard (Sheila), and co-sponsored by two other members
in very good standing, her acceptance to The Estate was a mere formality.
	When Cassandra entered the living room, she found Deidre sitting on
the loveseat, reading a magazine, the open brochure on the cocktail table
in front of her.  Deidre was wearing her dark brown wig, her favorite dark
blue dress with small white polka dots.  Well, not exactly her favorite,
but one they had both decided would be best for traveling.  Its full skirt
was more comfortable on the long drives they took looking for suitable
places for Deidre to be seen, and the color scheme did not draw undue
attention to her.  Underneath Deidre had on her padded bra, this time
filled out to C-cups, a move they usually thought too brazen.  He had first
put on full-cut brief panties and pantyhose, but the anticipation of his
new life had caused him to jack-off more than once as he dressed.  Now he
wore a garter belt and stockings with a thong two sizes too small over
them.  This should keep his cock under control.  If it didn't, he could
always pull it down and relieve himself without disturbing any more of his
clothing.  In fact, the need for such relief was quickly developing.
Finishing his wardrobe was a standard pair of three-inch stiletto pumps in
Navy blue.  Only his make-up, a little on the heavy side, detracted from
his appearance as the suburban lady of the house.  On the floor next to the
loveseat were Deidre's traveling suitcase and overnight case.
	It was only on seeing Deidre and not Colin that Cassandra realized
that she too wanted Deidre as a part of their lives.  She walked over to
Deidre and the two pressed cheeks, kissing the air besides each other's
face.  Sitting on the cocktail table, Cassandra picked up the brochure.
"Did you read this? she asked, knowing that he had.
	"Yes," Deidre beamed.  "Where did you find this place?"
	"That's a rather involved story," Cassandra replied.  "I'll tell
you on the way.  But ... are you sure you want to do this?"  Deidre could
only shake her head enthusiastically.  "Then grab your purse.  We've got a
long drive ahead."
	On the way to The Estate Cassandra explained about Sheila and
Douglas and The Estate itself.  One of the services is a training program
for submissives, who can be trained to perform a variety of traditionally
female jobs: maid, secretary, receptionist, waitress.  The Maids' Service
trains submissives in the duties of English maids, French maids, American
maids, plantation house servants, medieval wenches, colonial servants,
whatever type of female domestic the member desires.  The submissive can be
either male or female, but all will be trained--and dressed--as maids.
Since Colin was not aware of any of the arrangements being made for him, he
must be given the opportunity at several points to decline: when first
presented with the concept, just before entering The Estate, and
immediately after the nature of his training is revealed to him.  However,
since discipline is part of a maid's training, any resistance or defiance
once the training begins will be treated as role-playing on the part of the
trainee.  Cassandra was careful to let Deidre know that she could back out
anytime before the training started, but after that Deidre was committed to
the program, at least for that weekend.  Deidre was silent after this for a
long time.  Living as Deidre the woman was one thing.  Living as Deidre the
maid was something else.
	"If I don't like being a maid, can I still be Deidre?"
	Cassandra had not thought about this.  Since the only other
transvestites she had met were the husbands of Sheila and her friends, she
had not considered other options.  "After this weekend, Deidre can be
whatever you want her to be."  At this, Deidre relaxed.  "And remember,"
Cassandra continued, "you can say no anytime before we walk onto The
Estate."  Deidre just smiled.  * * *
	Just outside The Estate is Estateville.  This had originally been
the robber baron's company town, turned into a ghost town when the march of
time and progress made his business obsolete.  The Estate had acquired it,
with the estate, and maintained it as a company town.  All of the
businesses served a dual function: outwardly, they seemed like the standard
small town restaurants, motel, and shops of any rural part of any state.
But they were staffed by The Estate's employees or trainees or guests.  As
part of the weekend training session, Cassandra and Deidre were
automatically booked into the motel.  As they entered their room, nothing
indicated that it was any different than the dozens of other motel rooms
they had used.
	No sooner had Cassandra closed the door than Deidre hiked up her
dress and pulled down her panties.  Her cock had been straining for freedom
for over an hour.  With her panties at mid-thigh, she flopped on her back
on the bed and begin stroking herself.  Cassandra had been sexually aroused
since she saw Deidre sitting in the living room.  She wasn't going to let
that hard cock go to waste.  Mimicking her husband, she too hiked up her
skirt and straddled him.  She was not wearing hosiery, and had only to slip
the crotch of her panties to the side as she guided the cock into herself.
Grabbing Deidre's wrists, she pinned her to the bed while she rode her
cock.  Deidre's need was greater than Cassandra's, and she came in less
than a minute.  She quickly went soft, falling out of her wife's cunt.
	Cassandra knew that Deidre would not rise again without extensive
foreplay.  And foreplay was something Cassandra neither needed to receive
nor wanted to give.  As she looked down at her husband, a certain anger
born of sexual frustration, contempt, and confusion welled up in her.  She
would make Deidre pay for Colin's inability to satisfy her at this moment.
Well, ... not satisfy her with cock.  Deidre's tongue never deflated.  With
Deidre's cock now fully out of her, Cassandra knee-walked until she was
straddling Deidre's head, leaving a trail of cum on Deidre's dress.  Firmly
planting her knees on the bed, Cassandra nearly smothered Deidre as she
pressed her crotch into her husband's face, rocking from side to side and
forward and back to make sure Deidre's face was covered with the combined
discharges of their bodies.
	Deidre did not see the anger her cumming had caused, or the hatred
now twisting Cassandra's face as her wife wiped the transvestite's face
with her pussy.  They always included a lesbian sex scene when she was
Deidre.  In fact, most of their sex, whether he was Deidre or Colin,
involved his head plastered to her cunt.  To Deidre, this was just another
incident of eating his wife to orgasm, or orgasms as the case might be.  So
as he licked her lips, and probed her slit, and flicked her clit, and
nearly drowned in the flood of his semen and her juices, he did not know
that the orgasms Cassandra was experiencing were bittersweet to her, for
she not only wanted to cum, but to cum with a hard dick probing her pussy,
and a hard body riding hers.
	But as much as Cassandra wanted a hard cock, an experienced tongue
was what she had.  It was experienced not only in eating pussy, but in
eating her pussy.  Soon her rocking back and forth and side to side was not
motivated by anger but by lust.  While she may have wanted one mind-blowing
orgasm, the series of smaller orgasms that racked her body each time
Deidre's tongue circled her clit were just as good.  She rested her head on
the pillow now cradled in her arms, her hips raised, her ass moving in slow
circles.
	Deidre kept licking, establishing a rhythm between her wife's lips,
vagina, and clit, one hand keeping the lips open, the other stroking her
own cock.  She could easily spend the rest of her life as Deidre if this is
what that life would be.  Relieved by her orgasms, Cassandra looked at the
mirror over the dresser to see that a hard cock was now available.
Abruptly standing, she ordered Deidre to undress, doing the same herself.
Having less to remove, Cassandra finished first.  She pulled back the
covers and positioned herself in the center of the bed, legs spread.
	"Fuck me," she commanded when Deidre was naked.  "Fuck me hard, and
fuck me long."
	Deidre was now Colin again, only the smeared make-up a reminder of
Deidre.  He climbed on top of his wife and began performing his husbandly
duties.  His skin still tingled from the feel of the nylon and satin and
lycra he had just removed.  That, the anticipation of what the next two
days held for him, and having already cum only a half-hour earlier let him
meet Cassandra's command.  Resting whenever he felt himself ready to cum,
he was able to deliver a good twenty minutes of pumping Cassandra's pussy
before he again erupted.  Cassandra did not orgasm during this fucking, but
the nearly constant pistoning in and out of her cunt satisfied most of her
craving for cock.  But not her need for a hard body.  Colin was rather
slim, but not muscular.  And the smell of make-up, semen and her own juices
on his face was a constant reminder of why they were there.  But The Estate
has many services.  Maybe she should indulge herself while indulging her
husband.
	After they had showered, they ordered dinner sent to their room.
Since Colin had brought only Deidre's suitcase, he reverted back to Diedre,
choosing an ankle-length nightgown with leg slits.  With her painted toes
peeking through her high heel mules, and the traces of make-up still
defining her face, she still looked more female than male even without the
undergarments or the wig.  Cassandra wore one of the complimentary spa
robes provided by The Estate.
	As they ate, Cassandra explained that the training program in which
Deidre had been placed, the wife is always referred to as Mrs. X or Y.
Cassandra had decided to keep her married name so Deidre would have to
refer to her as Mrs. Nevins once the training starts.
	"I have been assured that you will be as complete a woman as
possible when this weekend is over."  Cassandra warned.  "If you have any
doubts about this, you can still back out."  Deidre could only shake her
head, already planning her life beyond the weekend.  The thought of days in
nylon and satin and lace and lycra resulted in her tenting the front of her
nightgown, being unrestrained by all that nylon and satin and lace and
lycra she was thinking about.
	Cassandra moved to the bed, sitting against the headboard, began
reading other brochures about The Estate's services she had not shown to
Deidre. "I also think you should call me Cassandra from now on," she added.
As she spoke, she looked at Deidre, only to notice the way the nightgown
was now poking out.
	"Deidre, come here," she directed, patting the bed next to her.  As
Deidre climbed onto the bed, Cassandra untied her robe, letting it fall
open.  Deidre started to lay next to Cassandra, but was corrected.
	"Don't lie down.  Sit up against the headboard.  Hike up that
gown."  Deidre complied, gathering the hem of the gown just above her pubic
hairline.  Her cock was now pointing toward the ceiling.  Cassandra
straddled her legs again, placed her hands on Deidre's shoulders, and slid
down the pole.  Leaning forward, she commanded "Suck my tits.  Make them
tingle 'til they hurt!"  Deidre again complied, knowing the combination of
soothing tonguework and sharp nips and bites she wanted.
	Cassandra did not move, savoring the feel of Deidre's lips, tongue
and teeth on her breasts as she squeezed her cunt around her husband's
prick.  As the sensations at both breast and pussy grew, she moved one hand
to the back of Deidre's head and the other to the top of her pussy.
Deidre, for her part, placed both of her hands at Cassandra's waist,
pulling her wife slightly to her.  Cassandra begin fingering her clit, the
motion causing her hips to rise and fall reflexively.  They stayed like
this for several minutes until Cassandra had that mind-blowing orgasm that
had eluded her earlier.  Satisfied, she pulled herself off her husband's
still hard cock.
	Deidre thought it was now her turn for satisfaction.  She was
wrong.  Cassandra went to her suitcase and pulled out a longline panty
girdle.  "Put these on," she said, tossing the girdle to Deidre.  Deidre
got up and put them on, thinking this was just part of a night of
lovemaking for them.  Instead, Cassandra removed her robe and climbed into
her side of the bed, turning her back to Deidre.
	"You better get some sleep," Cassandra said dryly.  "We have to get
started very early in the morning."  With that she turned off the lights
from her side of the room.
	Cassandra arose at 5:30 a.m.  She quickly woke up Deidre.  "You
must be in the conference room by 6," she informed her.  Deidre quickly
showered.  When she came out, Cassandra had laid out a plain house dress.
"Put this on.  And make sure you have on your bra and panty girdle.  And no
lipstick!"  When Deidre was suitably attired, Cassandra escorted her to the
conference room, halting at the door.  "If you really want to do this, you
have to walk in there on your own."  So saying, Cassandra turned and walked
back to their room.
	Deidre walked into the room.  There was only one other person in
the room.  Deidre immediately saw it was a man in drag.  She hoped she
didn't look that obvious.  By the clock on the wall, she was ten minutes
early.  During the next eight minutes three other women entered the room.
Deidre immediately recognized one of them as a man in drag also.  The other
two were more passable as women.  In fact, Deidre would have thought of
them as a woman but for their circumstances.  The one thing she found
strange was that none of the other transvestites were wearing lipstick.
	When the hands on the clock were perpendicular, a tall woman
wearing a lilac long-sleeve blouse, a deep purple vest, matching
ankle-length staight skirt, and three-inch black pumps strode into the room
and headed for the podium.  She surveyed the room with a self-satisfied
expression.
	"Good morning, ladies," she began.  "I'm Mistress Gertrude.  I will
be in charge of your training for this weekend.  You were to be informed of
the function and rules of The Estate, and the nature of your training.  To
make certain we all have the same understanding, let be review the terms
and conditions of your stay.
	"You have been registered here by a guest of The Estate who we call
your sponsor.  If that sponsor is a female, you will refer to her as
Mrs. whatever she wants to be called.  You will address all female guests,
or guests in a female role, as Mrs. or ma'am.  You will address all male
guests as Mr. or sir.  You will address all Estate staff such as myself as
Mistress, or staff in a male supervisory position as Master.  You will not
address anyone else, unless given permission.  You will response promptly
and directly to anything asked of you by guests or supervisors.
	"You will spend the next two days being trained as maids, according
to the desires of your sponsors.  Part of that training may require
discipline.  Your sponsors are having coffee in the dining room.  If you do
not wish to participate in the training, you are free to leave.  We will
arrange transportation back to your home towns, in appropriate male
attire."
	At this point Mistress Gertrude produced a box which she placed on
a table next to the podium, "I will leave the room for five minutes.  If
you wish to continue training, you will be wearing the lipstick which is
inside this case when I return."  Mistress Gertrude then strode out of the
conference room as imperiously as she had strode in.
	No sooner had she exited than the transvestite who was in the room
first bolted for the box.  Inside were five compacts and lipsticks.  She
grabbed one and began smearing her lips, not very well.  The other four
looked at her, then at each other.  After the hands on the clock moved a
tick or two, they too approached the box and removed a compact and
lipstick.  With varying degrees of skill and feminine demeanor they applied
the lipstick.  Deidre did not like the shade, a cherry red.
	Exactly five minutes after she walked out, Mistress Gertrude walked
back in, assuming her post at the podium.  She smiled to herself as she
surveyed the room.  "Ladies, follow me."  She led the quintet outside to
one of The Estate's motor surreys.  The trainees sat in silence during the
brief drive to the Maids' Quarters.
	It was only 6:20 a.m. when they arrived at the Maids' Quarters.
This was a three-story stone building which had been the single mill girls'
dormitory when the town's mill was in operation.  The top floor was an open
dorm which accommodated thirty maids.  Each maid had a space wide enought
for her single bed and a bedside armoire, not much larger than a military
locker.  At the foot of each bed was a hope chest.  For every five spaces
there was a vanity.  At the entrance to the dorm were coatracks on either
side of the door for overcoats, umbrellas, boots and other outerwear for
inclement weather.  Training occurred year-around.  At the far side of the
dorm was the showers and toilets.  Each space had its own dorm window, with
valanced curtains.  All the beds had identical bedclothes, and were
immaculate.
	Mistress Gertrude ushered the trainees to the dorm, walking them up
the three flights of stairs.  All of the future maids were wearing standard
3-inch pumps.  They were herded to a center set of beds along one side of
the dorm.  Mistress Gertrude assigned each one to a bed and instructed them
to undress.  They first undressed only to their lingerie, only the first
maid undressing fully.  All were wearing bras and a variety of panties,
pantyhose, garter belts, and stockings.
	"Undress means undress."  Mistress Gertrude sternly admonished
them.  They then proceeded to undress completely.  For three of them, the
entire episode was sexually stimulating and their cocks were in various
stages of arousal, one at full mast.  They were also at various stages of
hairyness.
	Mistress Gertrude ordered them to open their hope chests.  "In the
top tray you will find your toiletries.  Among these are depilatories.  You
will all now shower and remove any body hair other than a pubic patch no
higher than one inch above your member, and the hair on your head.  And for
those of you with a clitoral problem, you will relieve that problem before
returning.  You will be back here in ten minutes.  You may assist each
other, and speak to each other while showering."
	Deidre did not need to remove any body hair, but entered the shower
anyway.  Mistress Gertrude's tone indicated that everyone was to enter the
shower, regardless of need.  The person who was first to apply the lipstick
also was the hairiest.  She was also the most inept.  After using all of
her depilatory cream and removing only some of the hair, she looked at the
others in panic.  The most feminine looking trainee came to her rescue.
	"Hi, I'm Tami.  Let me help you."  The depilatories also included
safety razors.  Tami quickly and expertly shaved most of the hair from his
chest, his back and under his arms.  His legs were relatively clean.  When
Tami came to his crotch, she was faced with the clitoral problem, since the
first was also the most rampant.  "What do they call you," she asked.
	"Sherman ... uh, Sherrie," the first maid replied in a voice that
an opera villain would envy.
	"Sherrie, let's get rid of this 'clitoral problem,' Tami cooed,
moving to Sherrie's back.  Reaching around Sherrie, Tami grabbed his cock
in one hand and his balls in the other.  Pulling Sherrie into herself, she
quickly fisted his cock, causing him to spurt against the walls of the
shower.  As Deidre looked between them, she saw drops of something thick
and white drip from where Tami's crotch met Sherrie's ass.  The other two
maids with 'clitoral problems' were jacking themselves also.  The shower
spray washed their releases down the drain with their hair.
	"Ladies!"  Mistress Gertrude's shrill voice alerted them that time
was of the essence.  They quickly towelled off and came back inside the
dorm.  While Mistress Gertrude was not fully satisfied with the depilation,
it would do for the first weekend's training.
	She went to Sherrie's hope chest and removed a leather device.
Holding it up for all to see, she informed them "Each of you have a cock
harness.  Take it and gather around me and ..." she looked askance at
Sherrie.
	"Her name is Sherrie," Tami piped.
	Mistress Gertrude looked daggers at Tami.  "I will demonstrate the
proper application of the cock harness with Sherrie."  Mistress Gertrude
roughly grabbed Sherrie's cock and placed the leather harness over it.  The
other four put on their harnesses.
	Satisfied, she continued her instruction.  "You will remove the top
tray and place it on the foot of your beds."  After the trainees complied,
she continued.  "All maids wear the same standard undergarments.  The next
item you will put on is your girdles, which are on top at the right side of
the hope chest."
	The girdle was a special design, or rather one of several
foundation garments designed for The Estate.  This particular design was a
high-waisted, long-leg pantigirdle with corset lacing down the front center
from waistband to the middle of the crotch.  The lacing was so designed
that the cock harness was laced into the corseting and pulled snugly into
the crotch.  Once fastened, the girdle would contain the most rampant
erection, presenting a ladylike appearance at all times.  There were two
garters attached to each leg.
	The lacing begins at the waistband and proceeds to the crotch,
requiring the novice to be assisted.  Mistress Gertrude again chose Sherrie
as her model to demonstrate how the lacing was done.  This required Sherrie
to end up on her back with her legs raised and spread as Mistress Gertrude
tightened the lacing a little more snugly than was required.  Her handling
of Sherrie's cock cause another erection, despite the recent shower
activity.  This only demonstrated the effectiveness of the girdle, as
Sherrie's profile was perfectly flat.
	Mistress Gertrude then watched as the other maids helped each
other.  Deidre helped Carmen, who easily held her legs spread in the air
whild Deidre worked at her crotch.  Deidre had more difficulty with the
position, but Carmen had her rest her legs on Carmen's shoulders until the
lacing was finished.  Mistress Gertrude took note of Carmen's familiarity
with both the positions as top and as bottom.  Frenchi also were quiet
adept at the bottom positon.  Tami seemed more interested in being a top.
Afterward, Mistress Gertrude checked the lacing of each of maids, making
sure they were snug.
	"The next item is your Estate brassiere.  You may need the
assistance of one of your sisters."  The Estate brassiere was a longline
bra fitted with breast forms to give the wearer a c-cup.  Again, Sherrie
had difficulty with hers, to which Tami gladly assisted her.
	"The next item are your stockings," Mistress Gerturde next
instructed.  "They are seamed, and you are expected to keep your seams
straight at all times."  Each maid was already skilled in putting on the
stockings and fastening to the garters.
	"You will now replace your tray in your hope chest but leave the
chest open," Mistress Gertrude continued.  "In the armoire at the head of
your bed you will find the uniform you will be wearing this weekend.  Put
it on."
	Sherrie was to be an Edwardian ladies' maid.  Sherrie was relieved
that she would not have to wear anything revealing.  However, she was
discomfitted by the fact that she, as well as all the other trainees, were
required to wear three-inch pumps all day.  Tami was to be a scullery maid.
Tami was not pleased with this, since the uniform consited of a very plain
ankle-length long-sleeve button-front dress with white collar, white cuffs
and white apron.  She would have preferred being a French maid.  But her
sponsor had other plans for her.  The Carmen was wearing a ragged peasant
skirt and scoop-neck cotton peasant blouse.
	Deidre's Restoration chambermaid uniform was more involved.  There
was a multi-layer petticoat, a white cupless corset bordered in black, and
a white short-sleeve shirtdress with full skirt ending at mid-calf.  She
started to put on the corset, but Mistress Gertrude corrected her.
	"The corset is an outer garment."  Mistress Gertrude informed her,
helping the French maid into her dress, which barely covered the legs of
the girdle.
	When Deidre put on the petticoat and the dress, the petticoat
caused the skirt to balloon and bounce when she moved.  Mistress Gertrude
came over and fitted the corset on her.  The corset came just under her bra
cups, pushing them up as much as the longline bra would move.  The corset
laced both front and back with black laces, finished in a bow at the bottom
in back and at the top in front.  While not restrictive, it was
constrictive.  With the other garments she was wearing, Deidre had
something confining her from shoulders to sole.  And to complete that
confinement were the three-inch Estate pumps.
	When she finished lacing Deidre into the corset, Mistress Gertrude
was quite pleased with her charges.  The only thing that remained were the
wigs.  The Edwardian maid had black straight wigs with bangs, the hair
extending to mid-neck.  She had a short cap, like a nurse.  The French maid
was a redhead with shoulder-length curls, topped by a lace cap that was
more handkerchief than hat.  The peasant maid had the same hairstyle, but
in jet black and no cap.  Tami's wig was straight mousy-brown hair,
shoulder length.  Deidre was the only blonde, with straight shoulder-length
hair, and a white cap that fully covered the top of her hair.  Like the
corset, there was a black elastic band threaded through the hem of the cap.
	Mistress Gertrude was quite pleased with her charges.  Even without
make-up, Tami, Deidre and Frenchie were quite passable as women.  Make-up
would turn the peasant into Carmen.  Only Sherrie would be a drag.  It was
now 7:00 a.m.
	"Ladies," Mistress Gertrude intoned, "close your closets.  You have
a make-up kit in the top tray.  Remove it and close your hope chests."
When all had complied, Mistress Gertrude headed for the door, instructing
"Take your kits with you and follow me."
	She led them downstairs to the dining area.  Three maids, all of
them French, were clearing the tables and cleaning the area.  "This is
Brigit, Bambi, and Kim," Mistress Gertrude informed her trainees.  The
three maids curtseyed as they were introduced, then resumed their duties.
"Breakfast is from 6:00 a.m. to 6:30 a. m.  Being novices, you will be
permitted to eat from 7:00 to 7:30.  You may talk during breakfast.  If you
do not finish eating by 7:30 today, or by 6:30 tomorrow, you will be
disciplined.  If you refuse to eat, you will be disciplined.  A faint maid
is not of good service.  You will not be permitted back in the dorm until
your daily duties are finished."
	Mistress Gertrude then ushered the trainees into the kitchen, where
they were served cafeteria style.  Since Brigit, Bambi and Kate had cleaned
the dining area, the trainees were limited to one of the tables.  The
tables each sat six, intended to be five trainees and a mistress.  The meal
was quite heavy: eggs, sausage, ham, bacon, hash browns, biscuits, toast,
jelly, syrup, coffee, orange juice, grapefruit juice, pineapple juice.  The
Estate was well aware that for all the language, the attire and the
training, it was dealing with men who may not have eaten in more than
twelve hours.  Again, given the constrictive clothing they were wearing,
they would soon experience the folly of indulging their appetites.
	The trainees were reticent about discussing what situations brought
them there.  Everyone knew Sherrie and Tami by name.  The rest introduced
themselves.  In addition to Deidre, the French maid was Nora and the
peasant wanted to be called Carmen.  She was the only one who had chosen
what type of servant she could be.  Tami was the only one whose sponsor was
male.  At 7:30, Mistress Gertrude re-appeared.
	"Your first chore will be to clean up after yourselves.  Carmen and
Sherrie will clear the tables, Tami will report to the cook ..."  At this
Tami let out a shriek, then quickly covered her mouth.  Mistress Gertrude
gave her a disapproving look.  "Deidre and Nora will come with me.  And
don't forget your make-up kits."
	Deidre and Nora followed Mistress Gertrude to the surrey.  As they
rode back to the motel, Mistress Gertrude explained, "As maids, you must
always present the guests, staff and your sisters in service with the
proper feminine experience.  Therefore you will always be perfectly made up
when you are working, and will have your make-up kits with you at all
times.  This does not mean that you can or will spend your day primping.
The colors you wear will be The Estate's colors.  That means your nails,
including toes, and your lips will always be cherry read.  You will always
wear face powder.  Other make-up will be required when we are certain you
know how to apply and wear it.  You will now powder your faces and re-apply
your lipstick."
	This the two maids did, presenting the proper appearance when they
arrived at the motel.  Mistress Gertrude noted that she would not have to
train either Deidre or Nora in the application of make-up.  They were taken
to the floor which held their rooms and began cleaning, under Mistress
Gertrude's supervision.  They were thoroughly instructed in the making of
beds, with proper corners, the emptying of ashtrays and trash cans, the
cleaning of toilets and showers, the vacuuming of rugs were shown to them.
With every movement Deidre could feel the embrace of the cock harness, the
bra, the corset, the panty, the pantyhose.
	By the time they reached the room she had shared with Mrs. Nevins
the previous night, she saw the telltale signs of their lovemaking, and
recognized those signs in the rooms she had cleaned.  She blushed with
embarrassment when Nora commented on all the cum stains on the sheets as
Nora changed the bed linen.  When they had finished their floor, they were
returned to the Maids' Quarters.  Tami, Sherrie and Carmen were on the
second floor, which contains the maids' lounge area, as well as training
rooms such as a bedroom, an office, a living room, and a family room.
	Tami was in a foul mood since she had had to put her hands in
dishwater for the first time in years.  Sherrie kept fidgeting, not
comfortable with her foundation garments.  Only Carmen was happy, her lips
flaming red, her mascara and eye shadow and false eyelashes completing her
sultry Latina peasant look.  She had evidently satisfied Mistress Gertrude
that she both knew how to apply and how to wear make-up.
	Shortly after they got back, Sherrie had a near crisis as she had
to anwser nature's call and could not manage all the lacing.  This gave
Mistress Gertrude the opportunity to explain that we would have to piss
sitting down.  We could peel the panties down and up to take care of our
other business, but it was impractical to undue the lacing, piss, and redo
them.  Deidre didn't know what Sherrie found more embarrassing: having to
sit to piss, with her pantyhose down and her dress up, or having the other
maids watch her do it.  There were no stalls in the loo.  Mistress Gertrude
insisted that since the maids were all there, that all relieve ourselves,
as this would eliminate the need to do so later.
	The maids had lunch with the other maids, where they learned that
there were twenty-two of them there for the weekend.  The other seventeen
were in various stages of training, from a week to a month.  Five of them
were biological women, and three were transexuals.  Their Estate panties
were different, but all of their other garments were the same, and they
shared the dorm with the trannies.  Most of the maids had similar names,
ending in either i, ie, or y: Shari, Sherrie, Sherry.  The largest number
were dressed as French maids.  Four of the maids were self-sponsored
guests.
	After lunch, the Deidre and Nora were paired with someone else,
Deidre with Carmem.  The afternoon was spent cleaning the rooms of the
escorts.  Unlike the maids, the escorts have their own rooms.  Most of the
escorts had pictures of themselves in Estate uniforms and civilian clothing
all around their room.  Despite the ban on talking, Tami kept up a running
dialogue whenever Mistress Gertrude was away, commenting on the sexual
equipment or looks of the various escorts.  One exceptionally handsome
escort was named William.  He had a picture of himself nude and fully
erect.  When Carmen saw that, she commented that he would tax both ends of
her body.  Deidre tried to ignore her, but thought that a woman wouldn't be
able to walk right for a month after a night with this man.
	At the end of the afternoon Deidre and Carmen returned to the
Maids' Quarters.  Most of the other maids were in the downstairs living
area, watching television.  The only time they were allowed in this area is
the hour between the ending of their work day and dinner, and the time from
the ending of dinner to bedtime.
	Dinner was served precisely at 6:00 p. m.  Since all of the maids
were eating at the same time, the dinner period was a full hour.  As 7:00
p.m. approached, the maids begin drifting into the living area.  The three
maids who would have to clean the dining area knew who they were, and
remained.  The weekend trainees ate together, and watched the others,
taking their cues from their actions.  As everyone drifted toward the
living room, they too rose to go there.
	"Deidre," Mistress Getrude's voice was less sharp than normal.
"You will remain."  Surprise shown in Diedre's eyes.  She knew that being
ordered to remain behind was not good.  As the other maids went to the
living room or returned to the dormitory for the night, Deidre was escorted
to the basement.
	The basement was equipped with several rooms.  The room Mistress
Gertrude entered was barely furnished, with just a full-size bed, an
armoire, a nightstand, a hope chest/bench at the foot of the bed, and
several stuffed chairs.  Mistress Gertrude pushed her into the room,
closing the door behind them.  To her great shock was that Mrs. Nevins was
there, sitting in one of the chairs.  Why was her sponsor still at The
Estate?
	As she got over her initial shock, Deidre noticed a man standing at
the head of the bed, dressed in the uniform of an escort.  She had not yet
become aware of the various color schemes denoting the various functions or
duties of the staff.  If so, she would have noticed the black-and-lavender
tie.  Getrude guided Diedre to the escort, turning her to face Mrs. Nevins.
	"Does madame have any special instructions?" Getrude asked
Mrs. Nevins.
	Mrs. Nevins looked at the trio, studying them for several minutes.
Shifting her position slightly, she looked at Diedre.  "Diedre."  The maid
looked at her mistress, the fear very evident on her face.  "I have
overseen every aspect of your transformation into womanhood.  This
gentleman," she nodded toward the escort, "will take you another step.  I
understand that Mistress Gertrude will provide you with the proper
instruction.  Be brave, all true women must experience this at some time."
Mrs. Nevins then sat back, signalling with a nod that the event should
continue.  What Deidre did not know was that there was also a video taping
system which would record everything that happened in the room.
	Gertrude turned to the trainee and the staff member.  "Deidre, this
is William.  William, this is Deidre.  Remove your clothing."  William
immediately began unfastening his clothes, methodically placing them on one
of the chairs.  Deidre, in shock now that she realized she was about to be
deflowered, froze.  The picture of William and his immense instrument
flashed into her mind.
	"Deidre, did you not hear me?"  Gertrude asked, harsly.  Not
waiting for an answer, she grabbed the maid, turned her toward William, and
began unfastening her corset.  Finished, she ordered, "Now take off the
rest of your clothing."  Deidre removed her dress and petticoat, took off
her shoes and unsnapped her garters.  She was standing directly across from
Nrs. Nevins when she unfastened the girdle.
	"Wait!"  The voice was Mrs. Nevins'.  She was not aware of the
completeness of the maid's uniform when she signed Diedre into the maids'
service.  The girdle and cock harness arrangement intrigued her.  This was
a new vision to Mrs. Nevins, and she wanted a few moments to savor it.
Mrs. Nevins marvelled at the contraption which so completely imprisoned
Deidre's cock.  She would have this item before they left The Estate.
Satisfied, she signalled that the undressing should continue.
	William had finished undressing, since he had only to drop his
pants, and stood at the head of the bed, his cock rampant.  It was a most
magnificent cock.  Escorts in the black-and-lavender class have one
function at The Estate: fucking male transvestites.  It does not matter
whether the transvestite comes to The Estate as a guest or is sent or
brought for training as Diedre was; if she is to be fucked as part of her
stay, a black-and-lavender will do it.
	And for this duty, there are two types: slightly large cocks and
huge cocks.  Since most trainees are also anal virgins, the slightly large
cocks are recommended, giving the she-male the feeling of fullness a first
fuck should convey, but not being so painful as to be traumatic.  The large
cocks are recommended for she-males accustomed to anal sex.  But these are
only recommendations.  The sponsor decides.  Sheila had recomended William,
who had deflowered Gwendolyn.  William was over 9 1/2 inches fully erect,
and nearly two inches in width.  Naked, he stood at attention, both body
and cock, awaiting further instructions.
	Looking at him, Mrs. Nevins had a fleeting-very fleeting-feeling
that maybe she had been too ambitious in her request.  This was a cock
bigger than any she had ever had--and one she wouldn't mind having.
Deidre's response was not that fleeting.  Facing William as Gertrude undid
the lacings of her corset, she had a full view of his instrument.
Anticipating its invasion of her, she began whimpering, tears making the
mascara streak her face.  Surely Cassandra did not intend his being a woman
to go this far.  They didn't even engage in anal penetration in their
private lives.
	"Stop crying," Mistress Gertrude admonished her.  "You're not a
woman until you lose your virginity.  Now remove the rest of your
clothing."  Deidre removed the rest of her clothing, folding them and
placing them on one of the chairs.  She looked at Mrs. Nevins as she did
so, her eyes imploring her mistress to spare her.  Mrs. Nevins did not.
	Mistress Gertrude guided Deidre to the nightstand.  Opening the
drawer, she took out two condoms, and a large tube of lubricant.  Handing
the condom to Deidre, she stated "Place this on William."  One of the rules
of The Estate, for guests and staff alike, is no unprotected sex.  Deidre's
hands were shaking so badly she had difficulty getting the rubber on
William's cock, practically jacking him off in the process.  When she had
completed her task, Mistress Gertrude handed her the lubricant.  "I suggest
you make sure he is good and slick," she sneered.  Again, Deidre mearly
jacked him off greasing him up.
	When Mistress Gertrude had determined that William was ready, she
ordered Deidre onto the bed on her hands and knees, positioned so that
Mrs. Nevins would be able to witness the penetration.  "Grease her up,"
Mistress Gertrude instructed William.  He took the lubricant Deidre had
used on him and squirted a copious amount on his fingers.  Deidre had never
stopped whimpering or crying, and the insertion of William's finger in her
asshole changed the whimper into a moan.  William kept working her asshole
until he had three fingers inside her.  After several minutes, he looked at
Mistress Gertrude for the go-ahead.  The moment of truth had arrived.
	Mistress Gertrude looked at Mrs. Nevins, who nodded assent.
Mistress Gertrude nodded to William.  He placed the head of his cock at
Deidre's asshole, grabbed her hips firmly, and with a steady push invaded
her.  The moan turned into a wail so plaintive that even Gertrude winced.
Mrs. Nevins winced not.  William did not end his push until his pubic hairs
were firmly caressing Deidre's ass, his balls kissing hers.  Pausing only
long enough for Deidre's anal sphincter to make some adjustment to his
size, William pulled back until just the head was inside the opening.
Deidre's wail at the withdrawal can only be described as blood-chilling.
	William pushed forward again until ass met hair, then withdrew.
Gripping Deidre's hips as firmly as he could, he began sawing into the
maid.  Deidre's wails were now sirenlike and continuous, acccompanied by a
steady stream of tears.  Unmoved and transfixed, Mrs. Nevins watched
William's cock disappear into and reappear from Deidre's ass.  The only
thing that surprised her was William's stamina.  The fucking lasted a full
half-hour with no break in William's stroking.  After the first ten
minutes, Deidre had collapsed on her arms, her face buried in the
bedcovers.  Only William's grip on her hips kept her on her knees.  For the
next fifteen minutes he sawed in and out of her in a steady rhythm.  During
the last five or so minutes William picked up speed enough to come, burying
his cock in her and holding her ass to his groin.
	It took several minutes for William to become soft enough to easily
disengage from Deidre.  She looked a sight: ass in the air, head and
shoulders on the bed, face smeared with make-up and tears, whimpering.
William stood at the bedside, his rubber-clothed cock hard but not fully
erect.  Opening the lower portion of the nightstand, Mistress Gertrude
removed a filled wash basin and two wash cloths.  She gently wiped Deidre's
asshole.  Deidre winced at the touch, her whimpering occasionally turning
into moans.  The trio gave her some time to recover.  When it seemed that
she would not, Mistress Gertrude took charge.
	"Deidre!"  Mistress Gertrude said sharply, "you are not through
servicing William."  The statement shocked Deidre.  What other horror was
she to endure?  "Stop your whimpering and stand up!"  Scared not to obey,
the maid struggled to her feet, facing Mistress Gertrude.  Mistress
Gertrude looked at William's still cloaked member.  "You produced that
result, please clean it up."
	Deidre looked at Willian's cock in confusion, not certain what she
was expected to do.  Mistress Gertrude grabbed her hand and placed it in
the wash basin.  Now apprised her her next duty, Deidre soaked the
remaining wash cloth, then started to remove the condom.
	"Ah, um," Mrs. Nevins interrupted.  All three turned to her.  "I
think Deidre should have a momento of this occasion." Mrs. Nevins said,
indicating the condom.  "Its ... contents ... should be retained ..."
	Mistress Gertrude and William immediately understood, although
Deidre did not.  Mistress Getrude quickly informed her, "You are to remove
the condom so as to retain the fluid within it, Deidre."
	This presented a problem, since William was far from flaccid,
though not fully rampant.  He further refused to co-operate by becoming
more erect.  Deidre had to work the condom off of him, which caused him to
spurt a large load into the condom as she was trying to get the opening
over the prodigious head.  When she finally had it off, fully the bottom
third was filled.  Mistress Gertrude quickly took it from her and fastened
the opening with a clip that was part of the paraphenalia in the
nightstand.
	Deidre then wiped William's cock clean.  As she held his member in
her hands, she marveled that all of that monstrous organ had been inside
her, especially when she cleaned the head.  But the pain in her ass and the
awkwardness with which she now stood were ample evidence.  There would be
more when she walked up to her room.
	When William was clean, Mistress Gertrude turned to Mrs. Nevins.
"Would madam like the maid to orally service William?"
	The blood drained from Deidre's face.  Was there no end to her
humiliation?  Was she to take into her mouth the very organ that had just
ravished her ass?
	"No," Mrs. Nevins said, somewhat hesitantly.  "I think she's been
introduced to enough womanly duties for one night.  But ... soon, maybe."
With that, Mrs. Nevins stood, walked over to Deidre, and kissed her fully
on the mouth.  "I'll pick you up tommorrow," she said, breaking the kiss.
"Now you are truly a woman."  Looking at William's now fully rampant
member, she said, half to herself, "Yes, more of a woman than I am."
Turning to Gertrude "Please have the tape ready for us tomorrow.  And
... Deidre's souvenir."
	"Yes, Mrs. Nevins," Gertrude replied, and turning to William, "get
dressed."
	As Mistress Gertrude escorted Mrs. Nevins to the front entrance,
Mrs. Nevins waited until they were beyond earshot of the downstairs room.
"I understand you can have a dildo made of your escorts?"  Gertrude nodded
with a smile.  "I would like to examine William more closely for that
... privately.  Would that be possible?"
	"You can examine him here," the look of disappointment in
Mrs. Nevins face was unmistakable, "or at your motel room, if that is more
convenient."
	"Ah, yes ... my motel room.  That would be most convenient.  And
... uh, ... when will he be prepared to be examined?"  The question was
lost on Gertrude.  "Well ... he has already performed so ... admirably.
Will he be up for ... examination?"
	"Let me assure you, Mrs. Nevins," Gertrude cackled, "William is
always 'up' for examination."
	"Even without a ... someone like Deidre?'
	"William is unique among men, in many ways."  Gertrude snickered.
Mrs. Nevins could not help but notice how much mirth Gertrude derived from
discussing William's abilities.  "William's only sexual preference is that
he prefers sex.  anytime ... anywhere ... anyway ... anyone."
	"Then I can expect him tonight?"
	"Within the hour if that is madame's pleasure."
	"Yes ... that is exactly madame's pleasure."  So saying,
Mrs. Nevins left the maids' quarters.
	Mistress Gertrude waited until Mrs. Nevins had entered the surrey,
and the surrey was on its way back to the hotel before returning to the
basement.  Deidre was laying on the bed on her side, her back to William
when Mistress Gertrude walked in..  William had taken the seat Mrs. Nevins
had, giving him a perfect view of his cockwork.  Staring at him was a very
much enlarged asshole, one of dozens he had deflowered.  This sissy maid
would never be the same, he thought, and he was the man who had made the
maid a woman.
	Turning to William, Gertrude informed him, "Your services are
needed at the hotel.  Within the hour."  William did not have to be ordered
twice.  This was not the first time a sponsor wanted to savor what she had
just witnessed.  He quickly left.
	Mistress Gertrude went over to Deidre and pushed her fully onto her
back.  Pushing the maid's knees toward her chest, Mistress Gertrude had
full access to Deidre's crotch.  She had been somewhat apprehensive at
having William fuck Deidre.  But now that the deed was done, she knew that
Deidre needed a salve to both ease the pain and cause the asshole to close
somewhat.  Fortunately The Estate had its own medicinal cream for that.
The nightstand drawer was stocked with such an item.  Gertrude retrieved
the jar of cream and crawled onto the bed.
	Keeping the maid on her back, Gertrude dipped two fingers into the
jar and spread the cream into and around the maid's anal opening.  The
cream had an immediately cooling and soothing effect, causing Deidre to
sigh in relief.  Getrude stood up and quickly removed her skirt.  Quite
experienced, she had her girdle unfastened and heer cock harness removed in
less than a minute.  Deidre was still laying on her back, her eyes closed
as she enjoyed the relief the cream gave.  Gertrude quickly jacked herself
to an erection and placed a condom over her dick.  She then lubricated
herself with the cream.  Climbing back onto the bed, she crawled on top of
Deidre.  Before the maid knew what was happening, Gertrude had entered her
and was laying on top of her.
	Startled, Deidre tried to sit up, but was pinned by Gertrude.  As
she realized what was happening, she was confused by the sensations of both
pleasure and pain in her ass with the image of the woman on top of her.
She had not considered that Mistress Gertrude was also a she-male.  As
Gertrude pumped into her, the cream had a soothing effect on the still raw
tissues which Gertrude's dick was rubbing.  After William, she barely felt
Gertrude.  But the salve was working, and her asshole closed enough for
Gertrude to come.
	After coming, Gertrude laid on top of Deidre and whispered, "It can
be really good, if done right."  She then kissed Deidre lightly on the
lips, Deidre's first kiss from a man.  Again, Deidre's mind and feelings
were concentrated on her asshole and the kiss didn't register with her.
Gertrude pulled out and retrieved a tampon from the nightstand.  Liberally
coating it with the salve, she stuck in deep into Deidre's ass.
	"Get dressed."  Mistress Gertrude ordered, doing the same herself.
Deidre complied, or at least tried to.  The Estate girdle now presented a
problem as Deidre found it still painful to sit or to stand.  Mistress
Gertrude came to her assistance, lacing the front loosely, then returning
to dressing herself.  By the time Deidre was ready to put on the corset,
Mistress Gertrude was dressed and ready to help her.  Finished, Mistress
Gertrude washed the tear-stained make-up from Deidre's face, the only real
tenderness she had shown the deflowered maid.  She guided Deidre to the
doorway, and up the stairs to the dormitory, informing her, "You better get
some sleep.  Tomorrow is another day."

-000-
Postcards from The Estate//Maids' Service/Deidre's First Day	1