Frock Farm
By Lisa Lovelace
The attorney finished reading my mother's will. "Does anyone have
questions?"
"So he gets it all?" my Aunt Amanda said. "That little twerp now owns a
hundred percent of Frock Farm?"
That little twerp was me, Jesse Darmand, my late mother's only child.
Mom had died ten days ago in a high-speed rail accident on a business
trip to China. A section of track buckled and the train derailed. She was
one of a hundred victims. A contractor had just been arrested for using
substandard materials. Lawyers were already calling me. I would have to
deal with them at some point, but for now I was wracked with grief,
feeling sick and alone. Mom had been the focus of my world. My only
parent - my worthless father left before I was born, when she told him
she was pregnant. My only protector in a world where I got no respect.
Considering how things turned out, maybe I deserved no respect.
I was eighteen, had just finished high school and had applied to go to
State in the fall. I knew next to nothing about Mom's business and didn't
care. I knew exactly what I wanted to be someday: a historian of female
dress, focusing on the impact of technology on women's clothing during
the nineteenth and twentieth centuries. The rise of mechanical spinning,
weaving and sewing, new fabrics and dyes, artificial fibers, the
twentieth-century hemline - all of it fascinated me.
To be honest, I was drawn to the subject for personal reasons as well.
Since childhood I'd been plagued by a strong desire to wear female
clothing. I knew it was wrong for a boy to dress as a girl, and by a
supreme effort of will, I almost never allowed myself to indulge in an
activity that always filled me with guilt and shame afterwards.
While still a boy, I would sneak into my mother's room when she was out
and peek into drawers filled with sensuous lingerie and a closet filled
with beautiful dresses and nightwear. I loved the feminine scents of her
bedroom, bath and boudoir. But I swear to God, I never tried on any of
her things. I made do with a pair of panties and a full slip that I stole
from a cousin's dresser one Easter and hid under my mattress. If Mom
caught me wearing her clothes, I was afraid she'd be so angry that she'd
make me dress as a girl around the house, or even in public. Which, of
course, is what I secretly wanted to be forced to do. In what twisted
ways do desire, shame and fate make us behave!
"Yes, ma'am," my lawyer said. "Mr. Darmand inherits all his mother's
property."
Aunt Amanda - tall, athletic, my mother's imperious younger sister,
wearing three or four thousand dollars' worth of skin-tight cashmere and
leather - scowled. "And all I get is to be the little twerp's guardian?"
"Yes, ma'am. You have custody of the - uh, of Jesse until his twenty-
first birthday. From now till then, the estate will pay you $66,666.66 a
year for expenses."
Why did Mom put this in her will? I was a legal adult by most standards,
but she evidently thought I wasn't ready to run my own life, and so made
Aunt Amanda my guardian until I reached drinking age. This gave my aunt
effective control of Frock Farm. It also gave her control of me, though
she cared a lot more about control of the company. Two hundred grand for
three years' guardianship was nothing to sneer at, but what Amanda really
wanted was Frock Farm.
If you shop for certain types of women's clothes online, you might have
heard of my mother's company, Frock Farm. It's a Web site that sells
modest but attractive women's and girls' dresses based on classic designs
of the mid-twentieth century. All the dresses cover the shoulders and
have at least knee-length skirts, and many styles are available with long
sleeves and skirts. The dresses are classically feminine without being
fussy or frilly, and they appeal to customers ranging from hipster
fashionistas in Brooklyn to religiously conservative women - mostly
Christians of various sects, with a recent spike in orders from Africa,
but also some Jews and Muslims. It was an odd fashion niche, but Frock
Farm led it. Sales were up almost 60% last year.
Which was wonderful for Frock Farm, but I didn't want to be in charge of
it. Oh, I secretly admired a lot of its merchandise - for example, the
shirtwaist dresses in pretty rayon prints with trim bodices that
blossomed at the waistline into swirling skirts worn over crisp
crinolines. (Mom always wore Frock Farm dresses; Aunt Amanda never did.)
But I didn't know a damn thing about business in general or the fashion
business in particular.
You'd have thought that with my special interests, I would have tried to
follow in Mom's footsteps, but I wasn't smart enough to take advantage of
the opportunity she could have offered me. I was an artsy longhair type
who scorned commerce, feared numbers and froze at the sight of
spreadsheets or graphs. I was totally unfit to succeed my mother. I knew
it, and so did Aunt Amanda.
Mom had known everyone in the rag trade, went to dozens of meetings a
week, made hundreds of phone calls, handled thousands of messages and
emails. I had no contacts in the industry, would not be able to keep up
anything like her schedule, would not know what to do if I were in
charge. Mom never shared her management secrets with me. She knew my
limitations.
At the reading of the will, I learned that Mom owned ninety percent of
the shares in Frock Farm, which would be mine in three years. Amanda held
the remaining ten percent, but would control all of the shares until I
turned twenty-one. She'd helped my mother build the business and was the
chief operations officer, Mom's obvious successor as CEO. Amanda was
smart, knew the industry, knew what she wanted and knew how to get it.
The ironic thing is that I never wanted to stand in her way. She saw in
me a threat that didn't exist, and decided to remove it.
That evening, she summoned me from my guest bedroom to my mother's home
office. Aunt Amanda sat behind Mom's desk, still wearing her tight little
cashmere sweater and her tighter little leather mini. There was no chair
in front of the desk, so I had to stand before her like an errant
schoolboy.
"Things are going to change around here, especially for you," she said.
"While I'm your guardian, I will run Frock Farm. You will have no say in
business decisions."
"Sounds good to me," I said. "I don't want to have a say."
"So you say." Her eyes narrowed. "I'd be a fool to believe you, but even
if you think you're telling the truth, there are people in this company
who want you in charge, not me."
"Why?"
"Because they think you're weak, ignorant and easily led."
"Who says so?"
She snorted. "I won't name names. The old guard, your mother's cronies."
"Why do they think that?"
She snorted. "Well, you've never shown any interest in the business or
much of anything else, and to be blunt, you aren't much of a physical
presence, are you? You're what, five-four, one-twenty? A perfect size 6,
with hair down to your shoulders and a cute little bubble butt. They plan
to walk all over you, honey, and force you to force me out. I need to
make sure they don't."
"I don't want to force you out, Aunt Amanda! What do you mean, make
sure?"
"I mean that we have a problem. Jesse Darmand was last seen today at the
reading of his mother's will. He left with everyone else, and now he's
missing. No one knows where he is. We hope he's safe. However, you, my
dear, are not Jesse Darmand and never were. I'm going to help you assume
your proper identity."
"What are you talking about? I'm Jesse Darmand! I'm not missing!"
Amanda smiled. "Jesse is indeed missing, but fortunately for us, you're
not Jesse. You, my dear, are my new housemaid. Your name is Jessica
Darling, Jessica D. Darling - full name, Jessica Dearest Darling. You've
always been Jessica Dearest. You're a girl, of course. You've always been
a girl. You've never been a boy."
"Are you crazy? I'm Jesse! I've always been a boy! I've never been a
girl! Look at me! Do you want me to prove it?"
"Now, Jessica, calm down, that's not the way to think. I know it'll be
confusing at first, so I'll help you understand. Let's start by showing
you your new room. It's next to my boudoir. You'll love it, Jessica, it's
just perfect for you. Come with me."
"No! Are you crazy? My name's not Jessica!"
"Would you like a different name, Jessica? How about Jasmine? Or Julia?"
"No! I don't want to change my name!"
"Fine, we'll leave it Jessica. Now come along."
"No! I'm going up to my real room!"
"I'm afraid you can't do that, Jessica. The door behind you is locked,
and the room you're thinking of is empty now. Please follow me." She
opened a door in the back wall behind her desk.
"Open the other door, please," I said.
"I'm sorry, Jessica, I'm afraid I can't do that."
"Why not? Aunt Amanda, you have to let me go!"
She gave me a dismissive look. "Do I? Why? Because you say so? You, my
new maid? By the way, welcome to my household, Jessica. Why are you
wearing those ugly boy clothes? We need to get you changed into your new
uniform."
"I'm not Jessica, and I'm not a maid!" I tried the door. It was locked.
"What's going on? Am I being kidnapped?"
"What a unladylike way to put it. You'll be staying here, learning how to
serve me." Aunt Amanda tapped her phone.
Seconds later, a man quietly entered the room by the rear door. He looked
a question at her. She shook her head. He stood behind her, alert, never
taking his eyes off me. He was six feet at least, with broad shoulders,
taut abs and muscular limbs. He probably weighed half again what I did.
He wore a perfectly tailored dark suit with a crisp white shirt, a skinny
black tie and a slight bulge in his left armpit. He was strikingly
handsome in a Mediterranean way. The opposite of me - I was northern
European, slim, blue-eyed and blonde. Even though I was wearing boyish
clothes, his eyes roamed over me in a way that I found disconcerting. I
was extremely aware of his presence, and had trouble meeting his direct
gaze. He made me feel small and weak.
"Roberto, this is Jessica. Jessica, this is my personal assistant,
Roberto," my aunt said. "Come with me."
"What if I choose not to?" I asked.
She smiled. "Roberto will assist you if necessary." She walked out the
rear door.
I shot Roberto a nervous look and followed her, not wanting his
assistance if necessary. He followed me too closely for my comfort.
Amanda led us up a staircase directly across from her door. On the next
floor, a door opened onto the hallway outside the house's master suite.
She led us past the master bedroom, which wasn't in use, and unlocked the
door of my mother's bedroom. Inside the bedroom, she unlocked a door that
led to my mother's boudoir. Inside the boudoir, she unlocked a door that
led to her former lady's maid's quarters. Roberto followed, relocking the
doors behind us.
I'd never had occasion to see the maid's room before. My mother's last
maid, Lucy, was gone, heartlessly discharged by Aunt Amanda the day after
Mom died. The house had four guest bedrooms, but now Aunt Amanda was
calling me her maid and moving me into the maid's quarters, and I didn't
know how to resist. She seemed to be in control of everything.
The bedroom, which seemed quite spacious for a maid, was cold but
retained a faint scent of lavender, cedar and potpourri. It was feminine
in style, with French Provincial furniture in white with gold trim - a
double bed with bedposts and a lace canopy, a spacious chest of drawers,
and a woman's vanity with a lighted mirror and padded stool with a
ruffled skirt. A sitting area on the far side of the bed held a white
loveseat and a small coffee table. There was a neatly folded pile of
clothing on the loveseat, all black and white, and a pair of black patent
leather shoes on the floor. An open door led into a spacious bathroom
with a standalone tub and a tiled shower. The door next to it presumably
led into a closet. In the far corner of the room stood a full-length,
three-way mirror.
The rooms were well-lit, but had no windows. There were no screens. No
TV, no computer, no telephone. It felt more than a little claustrophobic.
"Sit," Amanda said.
I sat on the bed. It was soft, with satin sheets but no blanket, duvet or
comforter.
"These are your new quarters, Jessica," she said. "As you see, the only
way out goes through my boudoir and then my bedroom. There are three
locked doors between you and the public area of the house. You will not
be given any of the keys until you earn my trust."
"I won't stay in here!" I snapped. "I told you! I want my real room,
Jesse's room."
She sighed. "Oh, Jessica. I've already told you. Jesse's mother is dead,
and he's missing, we don't know where he is, but it doesn't affect you at
all, because you're not him. You're my new maid, Jessica Darling. You've
always been Jessica." She smiled. "Darling."
"No fucking way! I'm Jesse Darmand!"
She scowled and raised her voice. Roberto tensed but did not move. "No,
Jessica! I will not allow anyone, especially a nobody like you, to take
Frock Farm away from me! I built it! It's mine now! You're not a boy,
you're a girl, my new maid, and you should be changing into your maid's
uniform! I am your mistress, Jessica, and I will punish you if you
disobey me! Tell me your name."
"I won't!" I said. "You can't make me a girl!"
"Can't I? Let's find out," Amanda said. "Strip, Jessica. If you don't,
Roberto will help you."
Roberto took a step toward me. I was frightened now. I didn't want him to
touch me. I slowly stripped down to my black cotton boxers, shamed by the
sneer on his face.
"Those, too," Amanda said. I hastily took off my boxers and covered my
genitals with my hands.
"Hands at your sides," Amanda said. She eyed my equipment and snickered.
"Not much inventory in the men's department, eh, Jessica?"
Roberto laughed. I blushed. This was cruel. I had a hormonal imbalance
that had delayed puberty, and looked much younger than my eighteen years,
with narrow shoulders and scant body hair. My face was as smooth as a
woman's, with a delicate jawline. I had the male parts of a young boy,
not a man.
"You're sure you need me, Ms. Amanda?" Roberto said. His accent sounded
Italian. "This Jessica, she is no threat to you."
"Oh yes, she is," Amanda said. "I want this pretty little maid securely
under control at all times, for reasons I will explain to you later,
Roberto. I am making you personally responsible for her safety. You will
keep track of where Jessica is and what she is doing at all times. If she
ever leaves the house, you will go with her and will never let her out of
your sight. You will drive her wherever she needs to go, and you will
escort her closely at all times, making sure she never gets lost, and
then you will bring her home safely and escort her to her room."
"I understand, Ms. Amanda," he said. He ran his eyes up and down my naked
body.
I couldn't believe what I just heard. Was this stranger going to watch me
dress and undress, or stay in my room at night? Would he watch me use the
bathroom? This was beyond creepy. Why couldn't I convince Amanda I was no
threat to her?
My aunt turned to me. "Jessica, your dresser and closet are full of
lovely new clothes in your size. Your maid's daytime uniform is laid out
over there on the loveseat. Get dressed as Jessica and come next door.
I'll inspect you and tell you if there are any little details you've
missed."
"No! You can't make me dress up as a girl!"
"I absolutely agree, Jessica," she said. "You can't just dress up as a
girl, you must also think and behave like a girl, because you are a girl
now. You need to be a girl, a very convincing girl. It's for your safety.
If the police come looking for Jesse, they won't find him. They might
find a pretty housemaid named Jessica, who will curtsey politely and show
them in and out of the house without saying a word. She would never think
of saying she was Jesse, because she knows that's not true, and she knows
the police put liars in jail, and she's afraid of what would happen if
she went to jail wearing her maid's uniform. Very afraid."
Amanda looked me in the eye. "Jessica has never even met Jesse, has no
idea what happened to him. She knows she is a girl named Jessica Darling,
Jessica Dearest Darling. She knows she has always been a girl named
Jessica. She knows that if she tells lies about herself, she will be an
extremely bad girl and will be punished severely, starting with fifty
kisses on her bottom from my friend, Mr. Paddle. Go put on your uniform,
Jessica, and show me that you're ready to leave your room and assume your
proper identity as my maid."
"No! I am not Jessica, and I'm not going to dress as a maid."
Amanda gave me an evil smile. "Then don't. You can stay in your room,
wearing anything you like, for as long as you like. No room service or
heat, I'm afraid. If you want out, come to me properly dressed as
Jessica. There's water in the bathroom, so you won't die of thirst."
"Go to hell!" I said.
Amanda smiled. "I'm going to dinner, actually, Jessica. If you get
dressed properly, you can join me. When you're ready, just knock on your
door three times and say loudly, 'Jessica is dressed now, Madam!' and
Roberto will come to fetch you."
Roberto collected my discarded male clothing. He handed my phone, wallet
and keys to Amanda, who slipped them into her purse. "Be a good girl,
Jessica," my aunt said, and the two of them left.
I was naked and helpless. I had nothing. I inspected the pile of female
clothing on the sofa.
Black satin panties; a black satin bra; a pair of black lace-topped
stockings; a white taffeta petticoat; a beautiful black satin French
maid's dress trimmed in white lace; a ruffled white bib apron with long
strings to tie behind me in a bow; an Alice headband trimmed with ruffled
lace; and a stiffly boned corset of white satin trimmed with the same
lace. A box held two lifelike silicone breast forms.
Damn Amanda! The maid's uniform was so sexy, so tempting, but I would not
put it on. I had fought my desires so successfully for so many years. I
was a man, even if perhaps not much of one, and I refused to submit. I
would not let her dress me as a maid, and I would not let her take
control of Frock Farm. I didn't want to run it, but I couldn't just let
her seize control. It was a matter of principle now, of protecting my
mother's legacy from her paranoid, power-grabbing sister. Somehow, I had
to break Amanda's guardianship over me as soon as possible. I needed a
good lawyer.
But first I needed to get out of this room.
The afternoon passed slowly and silently. Stark naked, I paced the soft
pink carpeting, wishing I had my boy's clothes back instead of the
women's wear that filled the drawers and closet. I searched for a book or
anything else to pass the time, but the rooms held only female clothing
and toiletries. I felt chilled, but I refused to dress as a woman, and
there was nothing a man might wear, not even a pair of women's trousers
or leggings. No pantyhose, just stockings.
Sunset came, and then dusk, and then night fell. No one came to free me
or bring me food. The heat didn't turn on. Instead, refrigerated air, far
colder than normal air conditioning, poured into the room. I shouted, I
demanded to be let out, but no one responded. I wrapped the largest pink
towel around me, huddled under the bed's satin sheet and shivered. I
turned off my bedside lamp, which had a ceramic shepherdess as its base
and a frilly pink parasol shade. The room was pitch-black. I was cold and
hungry, and couldn't sleep.
Sometime during the night - there was no clock in the room - I gave up. I
was freezing and had to cover up somehow. Not in the maid's outfit - it
was too scanty to keep its wearer warm. Instead, I rummaged in the chest
of drawers. I found only lingerie, no pants or tops. I found a full-
length slip and a pair of stay-up stockings, and reluctantly slid them
on. I'd heard girls say that even though stockings were thin, they kept
your legs warm.
Hoping to find something warmer and more substantial, I opened the door
of the closet and turned on the light, which revealed a roomy walk-in
closet with clothes racks on three walls. A dozen or more dresses,
nightgowns and maid's uniforms hung above a low rack of mostly high-
heeled shoes. I saw no trousers, shorts or tights. I found a vintage
long-sleeved, ankle-length nylon nightgown and pulled it on over the slip
and stockings. I didn't see any heavy, practical robes, but found a white
chiffon peignoir and slid it on over the gown, just to add another layer.
I felt a sense of defeat as I put on the silky clothing. I didn't want to
dress as a girl, or at least didn't want to admit it, but I didn't want
to freeze, either. I reasoned that I wasn't doing this to be feminine, I
was doing it to stay warm. And at least I was choosing what to wear
rather than obediently putting on the ridiculous maid's outfit.
I climbed back into bed and shivered. After a while I got up, collected
all the towels in the bathroom and laid them on top of the satin sheet,
then crept under them. They helped, and eventually I slept.
I woke in the dark and groped for the light switch, wondering what time
it was. The room was frigid. I shivered in my thin layers of nylon and
chiffon under my makeshift covers. I was hungry. Hungry enough to change
into a skimpy maid's uniform and beg to be let out? It would be the most
humiliating moment of my life. I would no longer be Jesse. I would have
to look and behave like Jessica, a female maid, and curtsey to Amanda
every time I saw her. I just couldn't.
A thought came. Amanda said I couldn't leave the room until I was dressed
as Jessica. Did that necessarily mean in the maid's uniform, or did it
mean any of the clothes in the chest of drawers or closet? They were all
Jessica's clothes, weren't they? In fact, I was already dressed in
Jessica's clothes, in the slip, stockings, nightgown and robe. Enough to
satisfy my aunt? It was worth a try. At least my legs, arms and chest
were covered. If I put on the maid's dress, they'd all be exposed.
I got up, clutching the peignoir around me. I knocked three times on the
door and said loudly, "Jessica is dressed now, Madam!" So humiliating!
I heard steps toward my door. Roberto unlocked it and looked me up and
down. I quailed before him.
"That's a maid's uniform?" he said with a smirk.
"The uniform is ridiculous," I said. "I won't wear it. I put this on to
stay warm. I want my own clothes back."
He shrugged. "Ask Ms. Amanda," he said. He gripped my upper arm and
hauled me out the door and across the boudoir to the door of Mom's
bedroom.
I couldn't believe Amanda had the nerve to move into my mother's rooms so
quickly. Who said she could move in at all? Then I remembered that for
tax reasons, we didn't own the house, Frock Farm did. If Amanda
controlled Frock Farm, she controlled the house, too. She could probably
make me pay rent, or even evict me, or make me disappear. In a sense, she
already had. I would not leave the house in women's clothing - it would
be too embarrassing.
Roberto knocked once and waited.
My aunt's voice came from within. "Yes?"
"Jessica says she is dressed," he said.
"Does she? Well, bring her in."
He unlocked the door, dragged me into the room, closed the door behind
him and abruptly let me go. I huffily readjusted my makeshift outfit. I
was embarrassed to appear before my aunt in ladies' wear, but I had no
choice.
She was sitting up in bed, picking at a scrumptious breakfast on a tray
and reading The Wall Street Journal. So it was morning.
"Good morning, Aunt Amanda," I said politely.
"Curtsey when you enter or exit my presence, Jessica," she said. "You are
my maid, a servant, not a family member. Call me Madam. Don't use my
name."
Should I refuse, or should I obey? If I refused, Roberto could make me
obey. I had to appease Amanda before I could dream of escape. I'd never
curtseyed before, but I lifted the hems of my nightwear, bent my knees
and bowed my head.
She snickered. "You'll need to work on that."
"Good morning, Madam." I hated using the title, but didn't want to annoy
her while she stood between me and freedom, not to mention a hot meal.
"Good morning, Jessica. You say you are dressed?"
"Yes, Madam," I said. "Everything I'm wearing came from, uh, Jessica's
chest of drawers or the closet. Can you please call me Jesse? My real
name?"
"No," she said. "You are Jessica. You've always been Jessica. Are you
wearing panties, Jessica?"
"I have not always been -"
She raised her voice. "Are you wearing panties, Jessica!"
Roberto could make me show her, so I told the truth. "No, Madam."
Amanda pretended to be shocked. "A girl not wearing panties? Oh, my
goodness! How can a pretty maid like Jessica Darling be fully dressed if
she is not wearing her pretty panties?"
"May I please have my real clothes back, Madam?"
She wrinkled her nose. "We disposed of those... things," she said.
"Roberto, please take Jessica back to her room so she can put on her
panties."
He did, holding me by the arm again, and locked me in the maid's bedroom.
I looked in the panty drawer, but saw no plain ones - they were all as
lacy and frilly as the panties that went with the maid's uniform. So I
put on the uniform panties, knocked three times and said, "Jessica is
dressed now, Madam." I hated myself for giving in.
Roberto unlocked the door.
"You're not Madam," I said. "Should I say, 'Jessica is dressed now,
Roberto'?"
He eyed me up and down. "Maybe I would take you to a room without Miss
Amanda in it, and then we would see what would happen."
I shivered. Nothing that I wanted to happen, I was sure. He marched me
back to the bedroom.
Amanda sipped her coffee and gave me a sharp glance. I remembered to
curtsey, trying to be less clumsy than last time.
"Are you wearing panties now, Jessica?" Aunt Amanda said.
"Yes, Madam."
"Show me."
Blushing, I raised the nightgown and slip to show her the panties.
Unfortunately, my manhood was stiff, just routine morning wood, and she
remarked on it. Embarrassed, I let the gown and slip drop.
"No. Keep showing me," she said. I raised the hems again, exposing my
panties, in which I was now fully erect.
"Those are very pretty panties, Jessica," she said. "I'm not surprised
that wearing such pretty panties excites you."
"It's not that..." I began, but she interrupted.
"Are you wearing a bra, Jessica?"
Shit. "No."
"No...?"
"No, Madam."
"Jessica! A blossoming girl like you, not wearing a bra? That's not nice!
A girl shouldn't leave her room in the morning without her bra on. And
panties! I'm surprised I've had to remind you."
"Sorry," I said. "I can go put on -"
"Yes, do," she said. "But first, you forgot to say Madam again. You need
a reminder. Five swats. Roberto?"
Without a word, Roberto pulled me over to a wooden chair at the edge of
the room and forced me down across his knees. He pulled up my robe,
nightgown and slip, yanked down my panties, and gave me five stinging
spanks on my bare bottom. His hand was large enough to cover both globes.
I shrieked, more in surprise than pain, and struggled to get free, but he
was too strong and easily held me down. By the fourth spank I was in
tears, and after the last spank I broke down and sobbed. Roberto pushed
me off his knees onto all fours on the floor. I knelt up, pulled up my
panties and rubbed my bottom, sobbing.
"Jessica!" Amanda snapped. "Who said you could pull up your panties?"
"Are you kidding?" I shouted. "You let him hit me!"
"I told you, Jessica! When you break the rules, there are consequences!
Will you forget to call me Madam again?"
"No... Madam."
I hated her. She had always been kind of bitchy when Mom was still alive,
but now she had turned into a paranoid loony bent on defending Frock Farm
from an imaginary conspiracy to make me, not her, the CEO. I wouldn't
take the job if they offered it to me! I would - yes, I would rather be a
housemaid in a dress than try to run the company. Why wouldn't she
believe me? All this domination and submission drama was so unnecessary.
"The rule is that when you are spanked, you cannot pull up your panties
afterwards until I say you can. Showing your bare bottom - a very cute
bottom, I might add - is part of your punishment. Do you understand,
Jessica?"
I stared at the rug, thoroughly embarrassed. "Yes, Madam."
"When your panties are pulled down and you are spanked, Jessica, what
must you not do afterwards?"
"I must not pull up my panties until you say I can, Madam."
"And why not?"
"Because my... my bare bottom is part of my punishment."
"Good girl. Now, pull your panties down to the tops of your thighs, so
that your bottom is properly bare. Look, it's still pink! Now go to your
room, put on your bra, and fill it. Bras are complicated if you haven't
worn them before - though I'm sure you have. If you need help, ask
Roberto."
Roberto hauled me back to my room and locked me in. I trembled in anger
and shame, helpless under Amanda's control. What I was wearing now was
bad enough, and now I had to go put on a bra, the most feminine of
garments.
I picked up the uniform's bra, which matched the panties I wore, and
wrestled it on. The straps were too tight, so I had to figure out how to
loosen them. I slipped the breast forms into the bra and felt them settle
into the cups. They were heavier than I expected. I put on the slip,
nightgown and robe and looked in the mirror. I had boobs!
Did fully dressed include shoes? Probably. I found some fur-trimmed, low-
heeled mules in the closet and slipped them on my stockinged feet. They
seemed appropriate with the nightgown and robe. I hoped I wouldn't trip
in them.
Three knocks. "Jessica is dressed now, Madam!" Roberto unlocked the door
and grabbed my arm with one hand. His other hand roamed up the back of my
dress and managed to snap the back strap of my bra. I squealed. I
couldn't believe it - it was like being in junior high again. He marched
me back to face Madam. I promptly curtseyed.
She sighed, obviously displeased. "Tell me who and what you are."
A prisoner in a female loony bin is what I was. "Aunt Amanda, stop this!
I'm not a girl! I'm Jesse, your nephew!"
"Oh, Jessica, it's so disappointing to hear you talk like that. We don't
know where Jesse is, honey. No one has seen him since the reading of the
will. His mother's death devastated him, and I remember hoping he wasn't
thinking of harming himself. But you're not him, dear. Jesse was a boy,
and you're a girl named Jessica Darling, you've always been a girl, and
you're my new maid. And we're just trying to get you properly dressed in
your pretty uniform so you can have something to eat and start attending
to your chores, instead of spending another cold and hungry night in your
room. And you're supposed to call me Madam." Her voice hardened. "Do you
want another five swats?"
Roberto grabbed my arm, led me over to the chair and pulled me down over
his lap.
I cried out, "Please, no, Madam! I'm sorry, Madam! I'll remember! I'll be
good! Please!"
Amanda held up a hand. Roberto didn't spank me, but he didn't let me go,
either. He slowly pulled up my robe, gown and slip and resumed gently
stroking my naked bottom, with my panties pulled down. His hand was warm.
It was totally distracting, and I'm afraid I involuntarily wriggled on
his lap.
My aunt paid no attention to what he was doing. "What is your name,
dear?" she asked.
I lay over Roberto's lap, blushing at the feeling of him feeling me up.
He shoved a finger between my buttocks and touched the rosette of my
anus. I writhed, trying to dislodge him, and failed. His finger pushed a
tiny way into me and stopped. I twitched. I felt thoroughly humiliated. I
used to be a boy, but now I was being turned into a girl, a lowly maid,
passive feminine flesh in the irresistible grip of Roberto's powerful
hands. I... I was...
"I'm... Jessica, Madam."
"Very good! Jessica who?"
"Jessica, um, Dearest Darling, Madam."
"And what are you, Jessica, um, Dearest Darling?"
"Ah... a maid, Madam."
"Whose maid?"
"Your maid, Madam?"
"You don't sound very sure of yourself," Amanda said. "Are you sure
you're my maid?"
Did she really have to rub my nose in it? "Yes, Madam."
"Well, I'm not so sure you are! You say you're fully dressed, but you're
not dressed like a proper housemaid, not at all! Look at you! A nightgown
over a slip for some reason, and a robe that doesn't match! No panties or
bra until I told you! And those shoes! What were you thinking, Jessica?
What kind of uniform is that supposed to be? You look like a bag lady."
"Madam! I was just trying to stay warm last night. My room was freezing."
"Nonsense! You were just refusing to wear your proper uniform. You were
disobeying my direct orders! You were bad, Jessica, a bad, bad girl! I
will not tolerate such misbehavior. Go back to your room and put on the
clothing that we laid out for you last night. Your maid's uniform, do you
understand? All of it! I'm disappointed in you, Jessica. Even a sissy
trainee like you needs to be able to follow directions, and so far, you
are failing. Go! You may pull up your panties only if you put on your
uniform correctly."
This was ridiculous, but I had no choice but to placate her. "Sorry,
Madam," I said, and curtseyed. If I didn't put on the whole maid's outfit
this time, I'd be spanked, and I definitely did not want to feel the
sting of Roberto's hand. My buttocks clenched at the thought.
Roberto muttered something about stupid sissy maids who can't do anything
right as he led me back to my room and locked me in.
I was angry. Why didn't Amanda just tell me the first time that I had to
put on the uniform? Why humiliate me over and over in front of this guy
Roberto? He frightened me. He looked so powerful in his perfectly
tailored suit, and I felt so helpless in my mismatched lingerie. He knew
I was a boy, but he treated me like a girl, and I wondered what he wanted
from me, and whether it was what he wanted or what Amanda wanted.
I took off the robe, nightgown and slip, leaving on my panties, bra and
stockings, and examined the maid's outfit. I ignored the white corset,
which my body obviously was not designed to wear.
I pulled the petticoat up to my waist. To my embarrassment, the feel of
it swishing around my hips and rustling over my nylons made me harder in
my panties. Thank goodness no one could see! I pulled the maid's dress
down over my head and tried to zip it up, but couldn't - my waist was too
big. I thought about telling Amanda the dress didn't fit, and didn't
relish the thought of what she'd say. I decided I had to try wearing the
corset after all and see if I could somehow get it tight enough.
How on earth does a man put on a corset? I took off the petticoats and
slip, wrapped the corset around me over my bra and panties, and closed a
line of metal busks down the front. It felt tight already. The back was
laced with stout ribbons running through metal grommets. I found the ends
of the ribbons, drew out the slack and felt the corset hug my body more
closely. I tightened it as far as I could without crushing myself, pulled
the ends of the ribbons around my waist and tied them in a bow.
Would the dress fit now? I tried it on. No. The corset needed to be
tighter, and not just by a little. I remembered a scene from some old
movie where a maid was lacing a lady into a corset. It looked complicated
and painful, and I couldn't imagine doing that to myself. A real girl
might know how, but I didn't. There was no help for it. I knocked on the
door. "Roberto?"
"Si, cara mia?"
"Can you please come in? I need help." No harm in flattering his male
ego. "From a strong man."
He unlocked the door, poked his head in and grinned at the sight of me
half-dressed as a maid. I wished I could vanish instead of asking him to
deform my waist and rib cage.
"I can't get the corset tight enough." I wiggled out of the dress, untied
the corset laces and faced away from him, displaying all my pretty
lingerie. "Can you see what to do?"
Roberto laughed. "Si, bella signorina." He was a beast, but his deep,
resonant voice and cute accent charmed me nonetheless. I wished I spoke
Italian.
He adjusted the laces at the top and bottom of the corset, and with a
powerful effort drew them much tighter around my waist.
"Ow!" I cried. "I can't breathe!"
"Oh yes, you can," he said. "Like a lady. Shallow little breaths." He
adjusted the laces and gave them another yank. I yelped. And another. I
yelped again. Evidently satisfied, he wrapped the laces tightly around my
waist and knotted them behind me. I felt him tuck in the ends somewhere,
and wondered if I would be able to take the corset off without help.
"This thing is crushing me!" I complained.
"A lady like you must suffer to be beautiful, signorina," Roberto said.
"Can you put on your dress now?"
"Will you please leave the room?" I didn't want this man to see me
dressed as a maid.
"No." His voice was decisive. "You're decent in your corset, and you
might need more help."
So I had to let him watch as I cinched two taffeta petticoats around my
narrowed waist. I pulled the maid's dress down over my head, threading my
skinny arms through its little puff sleeves. I tried pulling up the
zipper, but reaching behind me was awkward.
"Permit me," Roberto said. He brushed my hands away and made me lean over
the table. He took hold of the zipper and, to my relief, slid it smoothly
over my corseted waist and slowly up my torso. The touch of his fingers
through the satin dress lit up my nerve endings. As the zipper climbed,
the corset and dress molded my body and my body molded them in return.
Roberto delicately fastened the little hook and eye at the top of the
dress. His hand stroked the nape of my neck, slid down my back, plunged
under my petticoats and caressed the seat of my pulled-up panties.
I jumped, slapped his hands away. "Hey! No!"
Roberto grinned. "I had to help you twice, signorina. Don't I deserve a
little reward? Sei bellissima, cara Jessica."
I was furious, but what was I to do? Slap him? I could report him to
Amanda, but for all I knew he was molesting me on her orders, to keep me
off balance. I wondered what he said in Italian, and bitterly reflected
that maybe I deserved this. The business world was cutthroat, and now I
could see that Amanda had been three steps ahead of me the whole way. All
I wanted to do was study the history of women's clothing! It looked like
I'd be doing first-hand research.
I ran my hands down my body, smoothing the maid's dress over my corset
and petticoat. If I had to dress as a girl, I wanted to look like one,
and to my shame, I felt proud of my new figure, with its compressed waist
and enhanced bosom. My heart pounded. I had to hurry. Apron next. I tried
to tie it behind me, then realized I could put the apron in the back, tie
it in the front and tug it around my waist. It took me a couple of tries
to make a tidy bow. The little lace-trimmed apron was practically useless
- too small to protect my poufy skirts, basically just a symbol of my
status as a servile female.
Shoes. I sat on the loveseat and tried to bend down to put on the black
patent Mary Janes with two-inch heels. The corset wouldn't let me.
"Roberto?" I liked feeling helpless in front of him. Shame on me! "Help
me with the shoes?"
"Si, signorina." He knelt before me to slip my Mary Janes onto my feet
and do up the dainty straps. I got an unwanted thrill from the touch of
his hands on my stockings, and had a momentary vision of the prince, the
glass slipper and Cinderella. He tightened the straps one hole too far at
first, and I had to ask him to loosen them.
I tried to rise, and would have fallen over if he hadn't taken my hand
and kept me upright. The corset and heels changed my posture, forcing me
to stand up perfectly straight while thrusting out my boobs and butt. I
looked over my shoulder to inspect myself in the mirror, and was
surprised by how feminine the corset's hourglass waist made me look.
Which was insane. Why was I doing this? Just to be allowed out of my
bedroom? Why did I need to follow Amanda's rules at all? I needed to
stand up to her, take off this ridiculous outfit, find some men's clothes
and escape! But how could I with Roberto following me around, and where
would I escape to? I was a petticoated prisoner in my own home. I had to
get out of my room before I could do anything else, and to do that, I had
to put on this silly uniform. Once I got Aunt Amanda to let me out, I'd
figure out what to do next.
"Are you dressed now, Jessica?" Roberto asked.
"Jessica is dressed now, Roberto," I said. Oops. "I mean, Madam."
"Do you?" he said.
I could not reply. He placed his hand under my chin, lifted my face,
kissed me gently, took me by the hand.
He gave me a wink, took me firmly by the hand and led me out of the room.
I tried to pull free, but he was too strong. He knocked at her door and
received permission to enter. He didn't grope my ass this time.
I curtseyed to Amanda. She did not look happy.
"This is getting tiresome, Jessica. I've sent you back to your room four
times now, and you come back still not fully dressed. Why are you wasting
my time, you stupid girl? Do you need me to tell you what you did wrong?"
I wanted to scream. Break something. Dared not. Took a deep breath. Did
not want to be spanked again. "Evidently, Madam."
She counted off my sins on her fingers. "Hair a mess. Not even brushed!
It's down to your shoulders, but you do nothing with it - no ribbons, no
pigtails, no ponytail, no braid, no maid's cap, nothing. No jewelry. A
maid shouldn't wear rings or bracelets because she works with her hands,
but modest earrings and a simple necklace would be appropriate. However,
I do see you're wearing your corset and managed to lace yourself into
your dress! Good girl! Are you wearing one petticoat or two?"
Arghh! "One, Madam. Am I supposed to wear two?"
"In that dress, I would. The skirt is so full that it needs more support
to present a proper profile. You should notice these things, Jessica."
I lost it. "Oh, come on! This is the first time I've ever worn girl's
clothes!" Almost true. "It's not fair for you to notice every little
thing! I'm a boy! Why are you making me wear this stuff?"
Roberto took a step toward me, but Amanda waved him back. She stood
behind her desk, taller than me in her heels, and shook a finger at me.
"Be quiet, Jessica! I'm not done telling you what's wrong with you. You
aren't wearing any makeup, which is inexcusable. You aren't wearing any
fingernail polish, and I'll bet no toenail polish, either. I don't smell
any perfume, body spray or deodorant. Have you even bathed today? A maid
is supposed to always be neat and attractive, but you're neither. You're
downright slovenly! I wonder if you're fit to be my maid at all. Maybe I
should kick you out right now, let you make your own way on the streets.
You'd certainly attract attention in that outfit! You might find a nice
man willing to take care of you... if you take care of him." She
snickered. "And his friends."
"Oh, please, no!" I said, terrified by the thought of being kicked out of
the house. Where would I go, where would I sleep, what would I eat, what
would I wear? She was right. On my own, I would fall into the hands of
bad people. This was my home, even if it was a lot less homelike since my
aunt moved in, and I wouldn't feel safe anywhere else. I had to do
whatever was necessary to stay here. Even if it meant dressing as a maid
to placate Aunt Amanda.
Roberto took my hand to return me to my room, not as tightly as last
time. I didn't resist. He squeezed it before he let it go. "Don't worry,
Jessica. You didn't hear it from me, but she likes you. Take your time
and do it right." He locked me inside.
Feeling like a complete idiot, I took off my apron, dress and petticoat
and started over. I wasn't a girl, didn't know how to be one, but if I
had to dress as one, I wanted to look as pretty as one. It wouldn't take
much - I hadn't tried very hard so far.
I brushed my shoulder-length hair and parted it in the middle, catching
each side in a clip and tying it in a bow of pale pink ribbon. Maybe I
could please Amanda by looking as girly as possible. I shook my head and
watched my pigtails bob prettily, a sight that both embarrassed and
aroused me. I slipped the maid's headband onto my head and looked even
more like a maid, which to my dismay made me even stiffer.
I pulled off my stockings, grabbed some dark pink nail polish and did the
best job I could of painting my toes, followed by my fingers. It was
awkward to paint my right hand's nails with my left hand. I couldn't do
anything else while my nails dried, so I just sat there, blowing on them
and waving them in the air. When my toes were dry, I drew my stockings
back up my legs, enjoying the feeling of nylon on hairless skin.
Knowing zero about makeup, I settled for a light coat of face powder, a
line of dark pencil along the upper edge of my eyelids, a bare touch of
dusty eyeshadow, and too much red lipstick. I had to redo my lips three
times before I didn't overdo it. I sensed that with makeup, less was
more, but had no idea how to pull that off. Surely she couldn't blame me
for that.
With my nails and makeup done, I put on the petticoat and searched the
drawers for the second petticoat Amanda wanted. Found it, pulled it on
over the first one and swung my hips to settle it over the first one. I
was surprised by the amount of rustling frou-frou it made. I shrugged
into the maid's dress, and was delighted when it still fit, but I had to
ask Roberto to help zip me up. He did so, and tickled the nape of my
neck. I sighed and didn't make an issue of it. At least he wasn't feeling
up my butt.
Jewelry. I reached into a bowl on my vanity for a pair of gold clip-on
earrings and a fine gold neck chain holding a tiny cross with a pearl on
it. Perfume. There were multiple bottles on the counter. I chose the only
one I'd ever heard of and dabbed on a little Chanel No. 5, probably in
the wrong places.
I tried to remember all of Amanda's complaints, hoped I'd fixed
everything. I was tired of trudging back and forth, especially now that I
was wearing heels. Even if they were just two inches, I wasn't used to
them, and they made my feet and calves hurt almost as much as the whole
girly uniform hurt my pride. I didn't want to be a maid, dammit! I wanted
to be a historian of women's clothing, to curate and document the history
of delicate artifacts of a vanished past in which a woman's dress denoted
her social class more strongly than today...
...Or did it? The clothes I was wearing certainly denoted my social class
as clearly as anything women wore a century or five ago. Of course, my
French maid's costume was a throwback, a reproduction of a fantasy
costume shaped by mass media, but it served the same purpose as women's
clothing did in history. Anyone who saw me in it today would know me for
a lower-class female servant of a higher-class master or mistress,
someone richer and more powerful than me, someone who could order me
around, someone I had to obey.
Roberto led me back to Amanda's room - Mom's room! I curtseyed to her. I
hated her.
"Have you worn a corset before?" my aunt asked.
"No, Madam," I said.
"Then I'll excuse you this time, but I want you at least three inches
tighter in a week. I'll have to have your other uniforms taken in. Let's
see - maid's cap, yes, jewelry, scent, yes, it does look like two
petticoats, very good, and... oh, dear... the worst makeup I've ever
seen, the very worst. Have you put on makeup before, Jessica?"
"Never, Madam."
"Then I won't punish you for that, either, but if your makeup isn't
perfect in a week, you'll get five kisses from Mr. Paddle every day until
it is. For a maid, less is more when it comes to makeup, so you'd better
practice! Hmm. Turn around, slowly, then fast, so I can see your skirt
and petticoats fly up."
I spun, and somehow managed not to fall over.
"Jessica! Your garters are not clipped to your stockings!"
"The stockings stay up by themselves, Madam. I wasn't sure what to do
with the garters, I've never worn them before."
"Oh, Jessica! Garters must always be clipped to stockings, even if you're
wearing stay-up thigh-highs. Or remove the garters if the corset allows
it, but don't let garters dangle loosely under your skirts. It's so
untidy."
Another random lesson in female attire. "Yes, Madam."
"Overall, though, I must say you look much better, Jessica. Cute
pigtails! You really don't need to wear a bra if your corset has full
cups like yours, but as Queen Victoria would have said, better an
undergarment too many than an undergarment too few." She paused for a
moment. "I have something else for you, dear." She handed me a small dark
green velvet bag tied with a gold ribbon bow. "Open it."
I did, and found it was a lovely bracelet, a thin band of what looked
like deep green jade decorated with delicate gold inlay, the work of an
artist. It was too small to fit over my hand. I saw no way to open it.
Amanda picked it up and somehow popped the bracelet open on an invisible
hinge. She placed it on my left forearm, just back of the wrist, and
snapped it shut. I saw no sign of a seam or release. It fit too snugly to
remove.
I felt obliged to admire it. "It's very pretty. Thank you, Madam." It
felt valuable. Why did she give me this?
Amanda looked into my eyes. "You won't thank me when you know what it
is," she said. "Listen up, Jessica. This is important for you to
understand, so you don't try to do anything foolish. That's not just a
bracelet, it's a military-grade GPS device. I can track your exact
location at all times on my cellphone. It's pretty much tamper-proof, but
if you somehow manage to disable or remove it, it will discharge all its
energy at once, knock you out and tell me where you are, and I will send
people to retrieve you. Never try to run away from this house. You'll
fail, and you'll be hurt."
She ran her fingers down my beardless cheek. "Do you understand now?
You're my housemaid, Jessica Dearest Darling - oh, how I love your name!
- and I'm the CEO of Frock Farm. Jesse Darmand is gone, and I've defeated
the people who were behind him. I know who they are, just a bunch of
deadwood, and in a week, they'll be gone."
"Aunt Amanda, you don't need to do this!" I said. "I don't want to run
Frock Farm! There aren't any people behind me! I really don't know what
you're talking about."
She gave me a wry smile. "Exactly what I'd expect Jessica to say. There's
a one percent chance it's true, but just to be safe, I will keep you here
with me. Roberto is in charge of you now. If you want to leave the house
for any reason, you must get my permission first, and Roberto will escort
you and bring you back safely and make sure you don't get lost. Now,
child, tell me your name."
"This is ridiculous!" I said. "You can make me dress up, but you can't
change my name!"
A sinister smile from my aunt. "Can't I? Do you have any ID, my dear?"
She had it all - my driver's license, credit cards, phone, contact list.
I was screwed. "No."
She walked over to the vanity, opened the bottom drawer and pulled out a
lady's handbag. "Of course you do. Here you go, Jessica. Ten swats at
bedtime for not saying Madam."
Ten swats! I really needed to remember to call her Madam. Madam, Madam,
Madam I'm Adam. I didn't particularly want a purse, but since I now wore
a dress with no pockets, I'd need one to hold my pocketbook, makeup and
so on. This one was nicely made, black leather lined in taupe silk, an
Italian brand I didn't recognize. Inside the main compartment I found a
batch of papers and a pocketbook. I pulled them out and looked through
them.
... A copy of a birth certificate for Jessica Dearest Darling, in
Chattanooga, Tennessee, 18 years ago. Parents Goober Darling and Sara Lee
Darling.
... A Social Security card for Jessica Darling.
... A state ID for Jessica D. Darling that wasn't a driver's license.
... A medical insurance card for DARLING Jessica D.
The pink pocketbook had one dollar in it. If I escaped, I'd be broke.
With no phone. How was I supposed to be an 18-year-old girl without a
phone? I abruptly remembered that Madam didn't need a phone to know where
I was.
"That's all you need for now, Jessica," Amanda said. "It proves that
you're a real person, real enough to satisfy anyone who might ask. Jesse
Darmand is still missing, honey, and may never be found. The police will
suspect suicide, but there will be no evidence."
"Except my DNA," I said. "Madam."
Amanda stared at me. I realized I'd just made a huge mistake. I did not
want to give her unpleasant ideas.
I knew exactly what had happened to Jesse Darmand, because I knew I was
him. She could claim I was Jessica the maid, but my DNA would tell the
truth. I was my mother's heir, the rightful owner of Frock Farm, and if I
could get away from here, I could contact the authorities and regain
control of the company. To prevent that, she needed to hide me and keep
me silenced. Which is why I was now a lowly servant girl at the bottom of
her household's pecking order, helpless, isolated and under constant
guard - and lucky to be alive.
I prayed Amanda wasn't considering the simpler, more drastic solution.
I'd much rather be a sissy housemaid than dead.
She blinked, ignored what I said and abruptly changed the subject. It did
not calm my fears.
"Now then, Jessica, you need to learn how to do your own makeup. Sit down
at my vanity and I'll start with the basics. How to put it on, how to
keep it fresh all day, how to touch up in the Ladies, how to take it off
at night."
It was Mom's vanity, not hers, but I sat anyway. If I couldn't make
myself beautiful in a week, I'd be punished, and I decided that I'd
rather learn to look beautiful than have my ass pounded. Even if it meant
learning how to touch up in the Ladies. I hadn't thought about that. If I
left the house, I'd have to remember to switch restrooms. I'd never done
that.
For the next week, I practiced makeup for two hours a day, watching
YouTube videos on different makeup looks and practicing in my mirror. At
first it was humiliating and boring, but I made progress. I sat up
extremely straight while doing my makeup, because Madam was making me
wear the corset almost around the clock, and every morning, she cinched
it half an inch tighter. I could take it off only to bathe or shower
every other day. At night, she loosened it a tiny bit, but never enough
to make me comfortable. Practicing makeup distracted me from the
discomfort... a little.
But then, after a grueling week of studying feminine disciplines,
victory! I somehow managed to pass both of Aunt Amanda's girly tests. I
did acceptable morning, afternoon and evening makeup, cleaning it off
between looks, and when she measured my waist, it was three inches
narrower. Laced that tightly, I had trouble breathing or doing housework,
but Madam was delighted.
So was Roberto, whose attentions became more aggressive than before. He
was pleased by my feminine figure, liked running his hands down my torso,
liked to stroke my bottom under my petticoats. I slapped his hands away
at first, but eventually began to put up with it and then, to my shame,
began to enjoy his touch. What was wrong with me? Maybe I was starved for
other sources of affection, or lust, or whatever it was that Roberto felt
for me.
~ ~ ~
A month passed. I wondered whether my jade bracelet was really a GPS, but
did not try to escape. Where would I go, dressed as a woman, with my fake
ID and no money? Nowhere. It would lead to trauma, not freedom, and with
Mom's death and everything else, I was full up on trauma. I needed no
more trauma in my life.
So I adjusted to my new life instead. I'd heard of Stockholm syndrome,
where captives develop emotional relationships with their captors, and I
wondered if it was - actually, I was pretty sure it was - happening to
me. I was embarrassed to find myself starting to have feelings for Madam
and Roberto. I found I wanted to submit to them, please them, obey them.
I grew hard in my panties when I said "Yes, Madam," or "Yes, Roberto,"
and curtseyed to them in my maid's uniform.
As Madam's domestic servant, I grew accustomed to dressing as a maid at
home. Eventually she allowed me to start leaving the house occasionally
to do the grocery shopping and run other little domestic errands, always
closely accompanied by Roberto. For these outings I was allowed to change
from my maid's uniform into a traditional housewife's dress from Frock
Farm. I chose a pretty frock with three-quarters sleeves, a calf-length
skirt and a full petticoat. I'm sure I looked quite retro among all the
women wearing yoga pants, but there was nothing I could do about it. At
least I didn't have to shop in my maid's uniform!
I wasn't allowed to drive, so Roberto took me everywhere. At first I sat
in the back seat, as if he were my chauffeur, but then he told me to sit
in front so that we would look more like a couple than a lady with a
driver. In public, he treated me as his wife or girlfriend. He paid for
me, opened doors for me, slid my chair under me when I sat or stood, held
my hand when we walked together. Dressed as I was, I wasn't going to risk
public humiliation by not responding to him as a female partner would. I
certainly looked very domestic in my housewife dresses, stockings and
heels, especially after Madam gave me a cultured pearl necklace, earrings
and bracelet to complete my look.
And then it happened.
One sunny Monday morning, as I was clearing the breakfast dishes,
perfectly turned out in my maid's uniform, there was a knock on the front
door. I put down the dishes, wiped my hands on my apron and hurried to
answer. When I opened the door, my heart almost stopped.
Two policemen stood on our top step. Their eyes roamed over me, but said
nothing about what I was wearing.
The taller officer cleared his throat. "Is Jesse Darmand here, miss?"
I froze in abject terror. Could not speak. Tried to say yes. No words
came out.
I heard the clip-clop of heels. Amanda entered the foyer. "Who is it,
Jessica?"
Before I could find my voice, the tall officer said, "Police, ma'am."
Amanda hurried to the door, all smiles. "Thank you, Jessica," she said,
dismissing me. "How can I help you, officers?" She led them into her
office and closed the door. I desperately wanted to hear what they said
but had no excuse to hang around, so I reluctantly retreated to the
kitchen to finish my chores.
An hour later, the office door opened, and she and the two officers
emerged. They seemed to be all friends.
"Thanks for your help, ma'am," the tall officer said. "If we find Jesse,
I'm glad he'll receive the treatment he so obviously needs."
"Thank you, officers," Amanda said, dabbing at her eyes with a
handkerchief. "So happy to support the department in any way I can." She
told me to show the officers out and watched me closely as I did. I dared
not say a word.
Only later did I realize that this was my last chance to escape from
Amanda, and I totally blew it. I should have said yes, officers, I'm the
missing Jesse Darmand and I need you to protect me from my crazy aunt,
who is trying to steal my mother's business and disguise me as a girl. It
was, after all, my home address, and they might have believed me,
although by that time I had been to the beauty parlor under Roberto's
close supervision and had a girl's hairdo, nails and makeup.
I was no longer Jesse Armand. I was Jessica the maid. When the cops
showed up, I was too intimidated and frightened to speak. Aunt Amanda
barged in and took control, and I was lost. I learned long afterwards
that the police had indeed come that day to question her about the
disappearance of her nephew, but she stuck to her story and they had no
evidence to contradict it. Evidence that I could have given, but didn't.
Silenced by Amanda's presence in the room, I curtseyed politely to the
departing officers and did not speak, and thereby lost my chance to
become a boy again.
~ ~ ~
Instead, I became Jessica. It took about a year. My aunt put me on female
hormones and had my testicles surgically removed. Deprived of
testosterone, my penis shrank, I grew breasts and a plumper bottom, and
lost muscle mass. Roberto and I flew to somewhere where people spoke
Spanish and where I underwent cosmetic procedures to feminize my nose,
chin, cheekbones and larynx and had minor liposuction to redistribute
fat. The drugs and procedures made me considerably prettier. Everyone
said so, even if it embarrassed me to hear it.
A month later, I was back home. I no longer saw any point in trying to
escape from Madam or going to the police with some wild story of being
kidnapped and feminized. By now she had become a pillar of the community,
having announced a plan to bring some Frock Farm production back to this
country from China, and I was afraid to confront her in any way.
The thought of leaving the house en femme and encountering any form of
male authority unnerved me. In any such encounter, I had no doubt, I
would be revealed as a boy dressed as a girl; Aunt Amanda would somehow
seize control of the situation and make me look foolish; and the
authorities would hand me back to her for whatever punishment she wished
to inflict.
Maybe it was the hormones, but I soon found I could no longer fight my
feminization. I was... I was a sissy. A coward. I took the path of least
resistance. I answered to my new name and submitted to Amanda and
accepted my feminine fate as Jessica the housemaid. I wore my maid's
uniforms inside the house and my housewife dresses outside it. I lived as
a girl, no longer thought of myself as a boy.
No one mentioned Jesse Darmand now. I once overheard Madam say that after
seven years, Jesse would be declared legally dead and she would own
everything. I thought about it and could not imagine how I could become
Jesse again. If I tried, I would fail. I knew how to keep house, not how
to run a business. I was outwardly a woman in every sense but one, and it
was shrunken and useless. I was Jessica Dearest Darling, officially an
unpaid intern at Frock Farm, in reality a feminized male maid in service
to Madam.
Roberto became more sexually aggressive as I became Jessica, even at
home, where Madam could see how he treated me. I hated it! He would grab
me and pat my bottom or steal a kiss whenever we passed in the hallway.
If I had to stand next to him, he would grab or pinch my ass. If I had to
sit next to him, his hand would try to creep up my stockinged legs under
my petticoats. The first time he stood directly behind me, he wrapped his
arms around me, cupped my breasts, pulled me back against his body and
slowly humped my butt. I could feel his cock rubbing against me through
my skirts. I was shocked and managed to squirm out of his grip.
From then on, I tried to keep out of his grasp whenever I could, but
couldn't discourage his attentions. He took a possessive attitude toward
me, and because he was Madam's personal assistant and I was just her
maid, I found it impossible to defy him, especially in public. He treated
me as his girl, and people started thinking of us as boyfriend and
girlfriend. I certainly didn't think of him that way, but what could I
do?
By now I had to think of myself as a woman who needed to protect herself
against men who did not respect women and felt free to grope and kiss
them. Men like Roberto. I hated the liberties he took with me. If we were
walking to the same meeting, he would draw my arm into his. If we shared
a seat in a car, he would wrap his arm around my shoulders. He always
paid for me, opened doors for me, pushed in or pulled out my chair at the
table, and generally treated me as his woman, his prized possession. I
wondered if Madam approved of the way he behaved, or simply hadn't
noticed. I finally went to her and complained.
"What's your problem with Roberto?" She frowned. "You've had sex with
him, right?"
What? "No! Madam."
"Really? I would have thought surely by now... He likes you, don't you
like him?"
The problem was that we were both boys, but I couldn't say that, because
she'd just get angry and tell me for the hundredth time that I was a girl
named Jessica. I had to come up with some other reason. "I'm... afraid of
liking him, Madam. He's so aggressive. If I kissed him, I don't know what
he might do, or try to do."
She smiled. "Afraid of what might happen, or afraid you might like it?"
She toyed with one of my nipples.
"Oh! Madam!" I gasped.
"He's so good-looking, isn't he?" she said. "Lucky you! May I offer you
advice, woman to woman? He's pursuing you, dear, the way boys normally
pursue girls. He's pursuing you and you need to accept or reject him,
that's what the girl is supposed to do. Have you rejected him? Are you
sure you don't like it when he touches you?"
"No! Not when he spanks me!"
"But when he's gentler?"
"No! Well, not at first. Now... maybe a little bit." I lowered my eyes,
ashamed to admit my need to be filled.
She smiled. "Well, if you don't tell Roberto no, he'll take it as a yes.
Boys do, you know. He probably thinks you're flirting with him, playing
hard to get."
I gasped. "No! Really?"
She rolled her eyes. "Look, Jessica, I prefer to look the other way when
my servants please each other sexually, unless it affects their
performance. He really is handsome, and you are very pretty. Why not
enjoy yourselves? You can't get pregnant, so it's actually rather
convenient. He's a good man, very loyal to me. You should want to please
him. In fact, I insist you do. Would you rather give him a blowjob, or
let him fuck your boy-pussy, or both? I can let him know."
"I've never done either of those things!"
"Really?" She blinked. "You're a virgin?"
"Yes, Madam."
"Good heavens! Well!" She would not say more, and sent me off to do the
ironing.
~ ~ ~
Roberto came to me that night.
It was nine o'clock, the latest polite hour for a social call. I was
sitting at my vanity in my prettiest nightgown and peignoir, brushing my
hair. A hundred strokes every night after moisturizing myself, the final
step in my beauty routine before bed.
A knock at the door startled me. Usually Madam just barged right in. "Who
is it?"
"It is Roberto, signorina."
Oh, God. Why him, why now? Had Madam sent him? I set down my hairbrush,
checked in the mirror, quickly touched up my lip gloss. Was I
underdressed? No, the corset and nightwear made me decent. I slipped my
feet into my fur-trimmed mules and opened the door.
He stood outside, dressed in his usual black suit and skinny tie. To my
surprise, he carried a gorgeous mixed bouquet. He held the flowers out to
me. "For you, signorina."
What was this? I was flabbergasted. I hesitantly accepted the flowers.
Roberto had never been nice to me. Arrogant, domineering, disrespectful,
far too free with his hands, willing to spank me until I cried - but
never nice. Now suddenly he was being nice. Why?
I felt I had to match his politeness. "Thank you," I said. "Please come
in."
He did. He stared at me and awkwardly adjusted his tie, which suddenly
seemed to be choking him. I sensed that he needed time to gather himself,
so I looked around for a vase to put the flowers in and found one in the
bathroom, filled with dried flowers. I dumped them into a waste bin,
filled the vase at the bathroom tap, arranged Roberto's fresh flowers in
it and placed them on the table by the loveseat. "So pretty! Thank you,
Roberto."
A silence fell. As the female in the relationship, I waited for Roberto
to speak. The silence lengthened. Whatever he had to say must be very
difficult for him.
He gulped. "May I... I would be honored if you would let me take you out
to dinner, signorina. Per favore. Please." He gave me a polite bow.
My jaw dropped. I snapped it shut. How was I to respond to this?
Handsome though he might be, this brute had laid my bare bottom over his
thighs and spanked me to tears at Madam's bidding. His powerful hands at
one time or another had roamed over most of my body, despite my protests
and physical resistance. He had never shown me any respect, and now here
he was, politely asking me out on a date? It made no sense, unless...
Of course! This was none of Roberto's doing. Madam must have put him up
to it. Why? I couldn't imagine, and from my point of view it hardly
mattered. I had to accept. I felt as if I was the girl in a mating ritual
from a generation ago: He, the boy, was asking me, the girl, out on a
date, and it was up to me to accept or reject him.
Except that we were both boys. Was he gay? I didn't think so. Was I gay?
I didn't think so. So why would Madam bother? No point in asking Roberto
- he probably didn't know what she had in mind. I would just have to wait
and find out what he had in mind.
"Yes, Roberto, you may take me out to dinner. When?"
"Are you free tomorrow night?"
I'd been planning to wash my hair, but... "Yes."
He told me to make myself beautiful by seven and he would bring the car
around to the staff entrance. He asked me if I liked Italian. I said no,
I adored Italians... that is, Italian... and hoped he didn't read more
into my answer than I intended. He bowed and politely bid me goodnight.
I managed a wobbly curtsey. "Thank you for the flowers... se?or..."
He winced. I hoped it was just my pronunciation. "Signor. Signor
Roberto... signorina Jessica."
"Signor Roberto," I said, and curtseyed to him.
"Signorina Jessica." He gave me a bow, with a look that made me catch my
breath, and left the room. Only afterwards did I realize that for once
he'd been a perfect gentleman. He hadn't touched me, hadn't even tried.
I was having an adrenaline rush. I gasped for air, feeling crushed in my
corset. Was Amanda trying to set me up with Roberto? Was this a way of
getting rid of me without committing a capital crime? Did she want me to
marry Roberto, become his sissy servant or girlfriend or housewife, and
sink into obscurity?
I might even be willing to do that if it would free me from Amanda, but I
was convinced she wouldn't let me go. She had me trapped. I was her
feminized maid, and I would be going on a date with her extremely
masculine personal assistant tomorrow night, for reasons unknown to me
and maybe to him. He would buy me dinner and undoubtedly would expect me
to pay him back with sex, as men always do. A blowjob at least, an ass-
fucking at most, unless I could talk him out of it. I hoped rape was out
of the question.
Emotionally rather than physically exhausted, I finally fell asleep.
The next day turned me into a ditzy female unable to decide what to wear
for my date.
I wanted to look nice but not sexy. I wanted him to see me as a woman,
not a girl - a lady, not a babe. I decided to wear one of my day dresses,
a hunter green shirtwaist with baby blue trim, a princess neckline,
elbow-length sleeves and a knee-length full skirt, and over it a pretty
baby blue cardigan accented in hunter green. I knew Roberto liked me in
petticoats, so I wore one - one, not two! - and made sure it did not show
under my dress.
Wearing his usual black suit and skinny tie, Roberto opened the front
door at seven, paid me a pretty compliment that earned him an ironic
curtsey, and handed me in to the passenger seat of Madam's staff car. He
drove us to the station in White Plains, where we took the train toward
town, got off at Fordham and walked a few blocks to Arthur Avenue, the
Little Italy of the Bronx. He clasped my hand as we walked down the
street. His hand was warm. I didn't try to pull away. Tonight, I was
willing to be his girl in public. I was under his protection in a
neighborhood I didn't know. He made me feel safe, a feeling that mattered
much more to me when I experienced the world as a female.
Roberto stopped me outside a restaurant called La Strega, the Witch, and
opened the door. We were quickly seated at the best table for two. I must
have looked impressed, because he laughed and told me La Strega was his
family's restaurant, owned by his father and uncle, and they would take
good care of us.
Which they did. His father, Emilio, came to our table, greeted us warmly
and poured us tiny glasses of a rip-snorting liqueur called grappa. One
was enough for me, but the men had another. And then we were served a
Tuscan feast, washed down with two bottles of Chianti classico from their
family vineyard in their home town of Greve in Chianti. I would remember
this meal until I died.
For starters, we had crostini with chicken liver pate, followed by
ribollita, a savory stew of vegetables and day-old bread. Cannellini
beans stewed with tomatoes, garlic and sage accompanied the main course:
bistecca fiorentina, an amazing T-bone two inches thick, with a seared
crust on the outside and very rare on the inside. We shared it - it was
too big for one person. I rarely eat red meat, and felt guilty, but I
could not believe how good the best beef in Italy tasted.
When we recovered from our meat orgy, we had hard almond cookies dipped
in sweet wine for dessert and stopped at the bar on the way out for a
shot of espresso with Emilio. Roberto's father inspected me at length,
and I wondered what he knew about Roberto and me. Did he think I was
Roberto's colleague, employee, friend, friend with privileges,
girlfriend, future wife? Did he know I was male? His eyes gave nothing
away. On our way out I kissed him on the cheek and thanked him for the
best Italian meal I'd ever had, and followed Roberto out the door.
It was a balmy night. I loved the feeling of my dress swirling around my
knees and left my cardigan unbuttoned as we walked back to the train
station. I felt safe and protected in Roberto's company, enough so that I
could ask him what the hell was going on.
"That was a lovely dinner, Roberto," I said. "Thank you! I must say,
though, that it felt very strange. You're usually not so nice to me! How
many times have you spanked me to tears? How many times have you touched
my butt or breasts in public? How many times have you treated me like a
little girl with no mind of her own? Too many times! So why are you being
nice to me now? Why did you take me to your family's restaurant and
introduce me to your father?"
He had the decency to look shamefaced, but didn't answer. I wasn't going
to let him off the hook. "Well?"
I recognized the look on his face. It was that of a man who was going to
have to bare a piece of his soul. It's funny. Women love baring their
souls to other women, but men hate baring their souls to other men. Being
neither man nor woman at this point, I could bare my soul or not, as I
chose. I didn't need to at the moment; instead, I could make Roberto bare
his. It was only fair.
"It started when I went to Madam," he said. "I told her I admire you
greatly, but that you don't respond to me as a woman should. I asked her
what to do."
I stared at him. He was casting me in the female role. "What do you mean,
I don't respond to you? When you spank me, I cry! When you grope me, I
push you away! Can't you tell?"
He looked at me. "Of course I can tell. I mean, you respond to me like a
man who's being forced to wear a dress. Not like a woman who loves to
look pretty."
"Well, what do you expect?" I said. "I am being forced to wear a dress!
I'm not a woman!"
"Madam says she's changing you into one. You're a girl now, and your name
is Jessica. She says I should start treating you like a woman, not like a
boy in a dress."
"What does that mean?"
He grimaced. "Jessica, it's my fault. She said so. She said you hate
being spanked, hate it when I touch you without permission, hate it when
I make fun of you, a boy in a dress, except that she says you're not a
boy. That maybe you like being spanked a little, but I take it too far.
That you might respond differently if I was kind to you and treated you
like a real woman. For example, by taking you out to dinner."
"I do not like being spanked! Not even a little!" I said. The tiniest
bit, perhaps, but I'd never admit it to him. "But otherwise, Madam is
right. I loved being taken out to dinner. It was lovely." I looked down.
"I haven't been out to dinner since... since Jesse disappeared."
Roberto tactfully ignored my use of the name. "When you became Jessica,"
he said, "a strange thing happened. At first I thought nothing of you.
You were just someone to protect. But then, when I began to follow you
everywhere, I began to have... feelings. Feelings for a woman who is not
female. A lust that I'll never confess to, because no matter what Father
Angelo says, love is not a sin."
Love? "The woman who is not female... is me?"
He closed his eyes, nodded, trembled, began to leak tears. I was so
impressed. A man, crying! I wanted to touch him, but it was too soon. He
would overreact, think he'd been forgiven. I had to push him a little
further.
"How would you expect such a woman to respond to you, Roberto?" I said.
"A woman you've treated so badly, a woman you've beaten until she cried,
a woman you've dishonored?"
He began to cry in choked sobs. "I would ask her, no, beg her, to forgive
me. There is bad blood in me. My father treated my poor mother so badly,
I treated you so badly. Oh, signorina, I'm so sorry. I hated myself for
having feelings for you, I didn?t want to admit it, but I do. Can you
forgive me?"
Ahh, Catholic guilt. How could I use it? "If a woman you treated so badly
forgave you, what would you do?"
His eyes opened. "I would treat her like a princess. I would never hurt
her again."
I had to ask. Had Madam planted the idea in his head? "Would you think of
marrying her?"
"Oh, signorina, forgive me, but I can marry only a Catholic woman, one
who can bear my children. I do not think you can be that woman."
Got it in one! Perfect answer, Roberto! I wanted to kiss him for it, and
did ? chastely, on the cheek.
"If we can?t marry, Roberto, we can at least be friends, can?t we? We
started off badly, but now that we understand each other..." I leaned
over and made a show of adjusting his tie.
He quivered. "I would like that, signorina."
"I would like that, too, Roberto."
"Have you ever lain with a man, signorina?"
"No! But I might with a man who treated me like a lady instead of a
maid."
"Oh?" he said. "And are you a lady, or a maid?"
"A maid during the day," I said, "but tonight you treated me like a lady,
made me feel like a lady. It was perfect, all of it. Did Madam tell you
what to do?"
He laughed nervously. "Si, signorina. I was satisfactory?"
"Quite satisfactory," I said. "Please take me home, Roberto."
He did. He took my hand when we got off the train, and I did not pull
away. He drove us home, parked the car and walked me up to my room. I
expected to feel his hand caress my bottom as I climbed the stairs, but
did not, and found that I missed it. He followed me into my room without
asking, and I did not make him leave. I ran my fingers down the lapel of
his jacket. He leaned over and kissed me gently on the lips, and I kissed
him back.
He slowly undressed me in the dark, taking off my dress, petticoat and
slip, but leaving me in my bra, panty, corset, stockings and heels. I
took off all of his clothes and knelt before him.
I was about to let a man use me for sex, something I?d never done before.
I was nervous and excited. I wasn?t attracted to other men. But tonight,
something about Roberto turned me on, made me feel feminine, made me want
to submit to him.
I took his cock in my hands, gently squeezed it, played with his balls,
slowly stroked him. I began to lick him as I stroked and then took him in
my mouth and stroked his perineum. I took more of his cock in my mouth,
but had a gag reflex and had to back off. I apologized, asked him to tell
me what he wanted. He did, and I did as he told me, and it worked.
As his excitement mounted, he grabbed my hair and fucked my mouth as if
it were a pussy, which hurt and humiliated me. He spasmed, groaned with
delight and filled my mouth with his salty slime. I choked it down as
quickly as I could. He let go of my hair. I decided not to clean his tool
with my tongue, and instead fetched a warm, wet washcloth from the
bathroom and wiped him clean.
I had given a man a blowjob. What did I get out of it? No pleasure, just
a mouthful of creamy goo. I had to abase myself on my knees, submit to
his masculine strength, let him fuck me in the mouth until he came. Why
did girls do it? Did they actually enjoy it? Did boys make them do it?
Maybe girls figured it was easier and safer to blow boys than risk
getting pregnant.
Roberto asked me if I liked the taste of his sperm. I didn?t lie.
He smiled. "Too bad," he said. "Maybe you?ll develop a taste for it. But
that?s not the only way we can have fun. Let?s try this." He bent me over
and poked a finger into my rectum.
"Ow! Don?t! You mean..."
"Voglio scoparti nel culo, signorina." His voice was husky. "I want to
fuck your ass."
I felt myself stiffen, and hoped he couldn?t see. "Oh, Roberto! I?ve
never done that." A show of innocence would inflame him. "Will it hurt...
signor?"
"Si, signorina. You?ve never...?"
"No, Roberto. You?re the first."
"Oh, Jessica! You bad girl, you?re making me hard again."
"Oh, my! Look at that! So soon?"
"It?s your fault, Jessica. Sei la strega! You are a wicked woman!"
Of course he thought it was my fault. His male mind probably thought that
while the blowjob was a nice appetizer, I owed him a proper fuck in
exchange for dinner. Nonsense! Even so, I couldn?t muster the will to
resist him. Some part of me was curious, excited, wanted it to happen.
Some part of me was growing stiff, which shamed me, and the shame made me
stiffer. Oh, I was a mess! He was just a horny dude, but I was in the
grip of emotions I?d never felt before. I wanted to control my
deflowering, but I also didn?t ? I wanted to submit to him, let him
overcome me, force his way into me, take me and make me his possession.
In the end, so to speak, it wasn?t me who decided. Roberto put on a fresh
condom, squirted lube on it and on my rear end, and slowly entered me
again. He was big, and oh, it hurt, and I whimpered, but once he got
inside, the pain eased. He began to thrust in and out, slowly and gently
at first, then faster and harder. At one point his cock started rubbing
against my prostate, and I immediately found myself in orbit around
Planet Bliss.
"Oh my God, Roberto, more! Like that! Yes! Yes! Fuck me! Right there!
Ahh! Ahh! Ahh! Yes!"
My excitement soared, and a minute or two later, without touching myself,
I had my first sissy orgasm. It was better than any I?d ever had as a
male ? deep and long-lasting, like the orgasms girls seemed to have. It
slowly faded... and then Roberto sped up again, and I had another. Oh my
God! Roberto took me the way a man takes a woman, and I deeply wanted to
be his woman, his girl, his sissy, his maid, his whore, whatever he
wanted me to be.
When he pulled out of me, I felt empty, hungry, unsatisfied. If he would
fill that aching void inside me, I would happily be his girl. I would
bathe and shave myself, pluck my brows, wear my prettiest lingerie, do my
makeup, perfume myself, put on the most feminine dress I had, sway and
swing my hips and stick out my breasts and wiggle my little behind for
him. If only he would fill me again...
That night, I dreamed that I was a maid in service to a cruel master,
except that his cruelty consisted of playing with my nipples and bringing
me to the edge of orgasm. I woke in the middle of the night, breathing as
hard as I could in my corset, and it took me some time to calm down and
go back to sleep in my moist panties.
I woke up in the morning to a burst of pleasure, and found Roberto
fondling my nipples. Ah, ah! I shivered and slid down his body, took him
in my mouth and fluffed him until he was on the edge. I didn?t want him
to cum in my mouth, so I backed off, rolled over and offered him my well-
lubed rear. He put on a condom and entered me, deeply enough to rub the
magic spot that so quickly brought me to the edge.
"Pronta, Jessica?" he said, stroking harder and faster.
Did pronta mean faster? "Si, si, si! Fuck me, Roberto! Fuck me! Oh God!
Oh God! Oh! Oh! Oh! Eeeee!"
We came at the same moment. I thrashed and squealed and impaled myself on
him as deeply as I could, trying to take in more of him, and whimpered
when he softened. I had another orgasm without touching myself. I had
discovered ? been shown ? a new way to have sex, so much better than the
onanistic satisfaction I gave up to become Jessica.
After that night, Roberto became my boyfriend, even in my mind. Did he
remain as gentlemanly as he had been that night? Well, not exactly. He
definitely wore the pants in our relationship and continued to order me
around. But he became more like an escort than a guard, a boyfriend or
husband even, and was more polite than he used to be, and paid more
attention to how I felt, and no longer manhandled me in public. I learned
how to wiggle my rump as a signal that I wanted to be touched. Which, to
my acute embarrassment, I did. By him, only by him. Other boys did not
interest me ? I was attracted to girls. And to Roberto, to him alone in
the world of men.
I felt ashamed and embarrassed and guilty to have become a petticoated,
cock-sucking maid, but in some strange way a corner of me was happy. I
realized that I was ever so slowly falling in love with Roberto and
Madam. I knew this was a case of Stockholm syndrome, of loving captors
who did not love me, but I was so starved for any sign of affection that
I gladly settled for whatever they offered. Madam found me useful for
household chores and occasional sexual services, and Roberto found me
useful for sex and cuddling, and I had to happily settle for that.
Of course, I hoped for more ? that either of them would say they loved me
? but they never did. Once or twice I thought Roberto was on the verge of
saying something, but no. I wondered about his relationship with Madam.
Did she secretly control his relationship with me? Of course she did. Did
she order him to take my virginity? Would he really use me as his whore
and then dump me to marry a nice Catholic girl someday? Would he continue
to use me if he did get married? Did I want that? Oh...
In idle moments I daydreamed about marrying Roberto, walking down the
aisle in my wedding gown, a vision in perfect makeup, perfect hair, a
perfect white dress of satin and lace with perfect underpinnings, looking
dreamily at my bridegroom in his perfect tuxedo and swearing to honor and
obey him. The ring on my finger... lifting the veil... the kiss... the
wedding night... and nine months later...
But daydreams always end. Back to my daily dusting and cooking and
cleaning and the everlasting laundry, so much of it mine, with me in my
lace-trimmed black frock, hourglass-waisted corset, rustling petticoats,
starched apron, matching bra and panty, smoky nylon stockings, black
patent heels, and a ruffled maid?s cap in my hair. There was work to do.
There was always work for a maid to do. I practice wiggling my bottom as
I moved from one task to the next. Madam liked to see my bottom wiggle.
~ ~ ~
One day I heard the little bell that Madam rang whenever she wanted me to
attend her. I set down my duster, checked myself in the mirror, quickly
touched up my lip gloss and found her on the sofa in her office
downstairs. I entered and curtseyed.
"I have good news and bad news, Jessica."
I trembled. "May I have the bad news first, Madam?" I hoped whatever it
was wouldn?t be painful, humiliating or both.
"I?ve decided not to let you attend State in the fall."
"Oh!" I was devastated. I had hoped Amanda would let me start college
this year, let me get away from Frock Farm, away from my maid?s uniforms,
away from my mindless housekeeping, away from her. That hope had kept me
sane in my demented world of panties, petticoats and pinafores ? and now
it was lost.
I must have let my disappointment show, because she gave me a look. I
curtseyed. "May I ask why, Madam?"
"Oh, Jessica, isn?t it obvious? Jesse Darmand applied to State before he
disappeared. I doubt he?ll show up for classes. You?d need to apply to
State as Jessica Dearest Darling, and it?s past the deadline to apply for
this fall, and there?s the slight problem that you have no high school
degree or transcript or test scores. To be honest, Jessica Dearest, I
don?t think my maid needs a college degree. I want you to focus on maid
training and housekeeping skills, not academic skills. Maybe you?ll be
able to go to State someday, Jessica, but for now, your maid duties must
come first, because that?s your role in this household. Understood?"
I wanted to cry. "I?m... disappointed, Madam," I said. "I?d hoped ?"
"Yes, yes, I know, but not just now. Your higher education is done for
the moment. I?m afraid that you have too much, um, lower education to
catch up on."
"Yes, Madam." I lowered my eyes. Was that the end of my dreams? Was I
doomed to be a sissy housemaid forever? Would I have to spend my life in
her service, dressed in rustling taffeta, satin and lace, cooking and
cleaning and dusting and washing and tending to my temperamental
mistress? A tear rolled down my cheek. Of course, there would be
Roberto... but what did Madam have planned for him?
"And now the for good news," she said.
I looked up.
"The reason you can?t go to State is that I have a new job for you! Oh,
you?ll still be my devoted little maid, but you?ll also be working part-
time at Frock Farm! Isn?t that wonderful?"
Her evident delight in whatever this meant made me nervous. I thought she
wanted me to have nothing to do with Frock Farm. Nor did I. What did she
have in mind? Would I have to work as a sales girl, or fulfill orders, or
mop the warehouse floor, or...?
"To celebrate my promotion to CEO and Frock Farm?s commercial success,"
she said, "I?m going to start a collection of important frocks of the
nineteenth and twentieth centuries, starting with one of Dorothy?s blue
gingham dresses from The Wizard of Oz and one of Scarlett?s gowns from
Gone With the Wind."
I was astonished.
"The gowns will be stored here in the ballroom until we can build a
proper exhibition space," she said. "The collection will require a
curator and historian ? not an academic expert, but someone flexible
enough to learn the necessary skills on the job. It?s minimum wage,
twelve hours a week, so you?ll still have forty hours for your maid?s
duties. And during those twelve hours, Jessica, you can wear any Frock
Farm dress you choose, not a maid?s uniform! Doesn?t that sound
wonderful?"
I couldn?t believe it. It was my dream job! I saw at once that it meant I
would never again wear men?s clothing. I would always be wearing a maid?s
uniform, a Frock Farm dress or my feminine nightwear. Was the job worth
sacrificing what was left of my masculinity? I wanted it so badly, and
had so little masculinity left, that I decided yes, it was worth it. Yes,
I would rather curate the Frock Farm Frock Collection wearing a dress
than go to undergrad classes at State wearing boy?s rough jeans and
scratchy t-shirt. Yes, I would rather be a girl than a boy, would rather
be a maid than a man.
If the Frock Farm collection grew, maybe someday I would be able to spend
half my time as a sissy maid and half my time as a sissy scholar. What
historic frocks would we need to collect? If we wanted to charge
admission, famous Hollywood gowns might attract more customers than
actual historical dresses. Dorothy?s dress and Scarlett?s gown would be a
wonderful start, if Madam could afford them. I wondered how much money
she had to spend on this collection. What about Audrey Hepburn?s black-
and-white Ascot gown in My Fair Lady, or Deborah Kerr?s enormous
crinolines in The King and I? If they still existed, they might be
priceless.
And then I had the thought that might make it all possible. What if we
showed perfect reproductions instead of the original gowns? It would be
vastly cheaper, and would customers care? The gowns they remembered
seeing on the screen were reproductions anyway. We could show them
gorgeous costumes that looked just like the ones in their favorite movies
without having to buy the originals. I decided to create a proposal to do
this and submit it to Madam. Should the collection also have a Frock Farm
retail shop? I would have to think more about this. I would come back to
Madam with a well-prepared list of ideas...
But first, I needed to show her my abject gratitude for my new role in
her service. I bowed my head, spread my skirts wide and curtseyed to her
as deeply as I could.
"It sounds perfectly lovely, Madam," I said. "I gratefully accept. May I
thank you?"
She lay back on the sofa, raised her skirt and spread her legs. The
crotch of her sheer black panties glistened.
"Yes, Jessica Dearest Darling, you may."
The End