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A Lady’s Sissy Maid –
Day One
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Steve was single and it had been awhile since he was in
a meaningful relationship, so one Saturday afternoon, he
was aimlessly perusing a local fetish contact newspaper
when a particular ad caught his eye. It read:
“Sissy Maid Sought by Refined Beauty"
Classy, beautiful and refined lady is in search of a sincere
sissy to perform my household duties and become my personal
servant. Applicants must be docile, follow instructions
and have a sincere desire to serve and satisfy this high
class lady, who will only accept the best. A proper uniform
will be provided.
You must be well versed in all domestic duties as well as
understand the role of a sissy maid. Perfection is expected
therefore poor performance will be dealt with in an appropriate
manner. Strict forms of domestic discipline are practiced
in my household. Submit your resume to:
Ms. Enya Box 41637 New Westminster, BC V3M 6L1
For some reason the wording of the ad intrigued Steve,
he mulled it over for the afternoon and considering that
since he was an only child and his mother taught him to
be respectful to women, to cook, do household chores and
to pamper any woman he was with, he felt that he had the
credentials sought by Ms. Enya and had nothing to lose by
responding to the ad.
He sat down and wrote about his upbringing and his experiences
with the women in his life. He detailed his formal chef
training and how nothing in the world would please him more
than to make a beautiful lady’s life more pleasurable.
He hurried to the post office to mail his letter and a week
later a package arrived in the mail. It contained a book
titled “A Charm School for Sissy Maids” by Mistress
Lorelei and a note that advised him to read the book and
if he was still interested in the position he was to call
(604)525-2323 to arrange for an appointment.
He read the book that evening and the more he read the
more he realized that this was destiny, he was perfectly
suited to be a Sissy Maid. He eagerly called the number
and spoke with Ms. Enya, she provide him with some basic
details and instructions to attend her residence on Saturday
at 2:00pm sharp. Ms. Enya had a pleasant tone, yet it was
clear by her demeanor that she would not put up with improper
behavior.
He had difficulty finding a parking spot and when he rang
the entrance buzzer to her luxury condo building he was
a few minutes late. He was admitted and preceded to her
floor, he rang the doorbell and within seconds he heard
the distinctive sound of high heels walking on hardwood
floors. The door opened slowly and before him stood a strikingly,
gorgeous lady with her dark hair up in a bun and piercing
green eyes, that looked as if they belonged to a Goddess.
Steve always admired a lady with shapely legs and he immediately
noted that she was wearing black stiletto heels and fine
black stockings that accentuated her shapely legs. She wore
a very classy and expensive looking black leather skirt
and a crisp, white blouse that did little to hide the fact
that she was wearing a black brassiere, which held her ample
breasts high as they strained against her white blouse.
Instantly Steve could feel something stirring in his pants
as he gazed upon this beautiful woman.
“Welcome Steve, it is a pleasure to meet you”,
Mistress Enya said smiling as she motioned him to enter
and shook his hand.
Once the door was closed, she gave him a hug and playfully
patted him on the bottom. With that, she turned around and
motioned him to follow, instantly Steve’s eyes noticed
that she was wearing seamed stockings and her shapely bottom
filled out her skirt beautifully. To accentuate this, after
a few steps she bent over to pick up some unseen object
on the floor. This was clearly for his benefit as now her
skirt rode up revealing her stocking tops and garter belt
tabs. She straightened up, looked over her shoulder, gave
a wicked little smile that was almost a smirk and strutted
into the living room while Steve followed along like a little
puppy.
She walked over to the mantle and picked up a container
that held numerous folded slips of paper.
“Steve, take a slip and have a seat while we chat
a little.”
Steve took a slip and noticed that Mistress had gorgeous
painted nails and wore tasteful, refined jewelry. The stirring
in his pants was now becoming uncomfortable so he quickly
sat down fearing that Mistress would notice the bulge in
his pants. She glided past him and sat down on the sofa
across from him, letting her figure hugging skirt slide
up a few inches, then seductively crossed her legs revealing
her stocking tops ever so slightly. Poor Steve was clearly
falling under her charms; in embarrassment he caught himself
staring at her shapely legs so he looked up towards her
face, only now he staring at her breasts, he couldn’t
help but notice the details of her black lace bra through
the thin white fabric of her blouse.
“What time is it?”
Steve looked at his watch, “2:10pm ma’am”.
“What time were you to arrive?”
Before he could reply she answered her own question, “2:00pm
sharp not 2:05pm!”
“I, I, had difficulty parking Ma’am.”
“I do not except excuses so consider yourself warned.”
Steve was a little stunned at how her pleasant demeanor
quickly changed to being more authoritative yet remained
refined. At this point, she began to explain the position
and her requirements,
“The position is plain and simply, the position of
house and personal maid, the successful applicant will handle
all household duties that are beneath my attention. It is
your objective and desire to humbly and respectfully serve
a Dominant in the objective of cleaning, servitude and housekeeping.
This means all cooking, cleaning, laundry, ironing, answering
the telephone as well as serving me in all manners that
I choose. The sissy maid is expected to learn from her mistakes
and take punishments as required from misbehavior, incorrect
application of training or attitude adjustment. Each day
upon your arrival, you will receive a typed list of tasks
to be completed and other miscellaneous duties that I may
desire you to perform. Let me make myself perfectly clear
because I never want to have to repeat this to you. The
sole duties of my maid are to please me and make my life
more enjoyable. After a long difficult week I expect to
be pampered, as a lady of my stature deserves, this may
include massages, pedicures, bathing me or even allowing
me to take out my frustrations in my own special way. Please
understand that I am a fair and loving Mistress but I also
expect nothing less than perfection, upon the completion
of each task it will be inspected and graded depending on
my level of satisfaction or dissatisfaction you will either
be praised or more importantly corrected. Correction may
be immediate or some time later, my methods of correction
are fair and in line with the level of dissatisfaction.
Now on to some basic rules:
1. You may only speak when spoken to.
2. I shall be addressed as Mistress, Madam or Goddess.
3. Upon entering the room you must curtsy before me.
4. When I arrive home I am to be greeted at the door with
my favorite beverage.
5. Your uniform will always be properly worn and subject
to inspection.
6. All duties are to be performed without question.
7. Following your punishment you must thank me.
Now I am going to give you a moment to think about my rules
and expectations, if you do not feel that you can live with
these basic rules you are free to leave.”
Mistress then got up and left the room so Steve could ponder
his fate. The erection in his pants was now raging and although
he was scared to death, there was no way that he could get
this gorgeous woman and her curvaceous body out of his mind.
Mistress returned and before she could say anything Steve
said, “I wish to continue my interview to be your
Maid.”
Mistress smiled, “Very well Stephanie, follow me.”
Although she said it in a kind and loving tone she grasped
him firmly by the elbow and lead him down the hallway, as
if he were a child.
“You may remove your clothing, place it in this
bag and report to me in my bedroom.”
Steve did as he was told then anxiously and cautiously
entered her bedroom where Mistress was busying herself in
the closet. Steve was both scared and aroused and to maintain
his modesty he covered his genitals with both hands. Mistress
turned around, put her hands on her hips, which only extenuated
her womanly figure and authoritative demeanor.
“Put your hands behind your back”, she snapped.
Steve was shocked at her tone and immediately did as he
was told, his erect penis jumped out and Mistress Enya’s
only reaction was a short sigh of disgust. Without a word
she inspected him by slowly walking around him and Steve
instinctively lowered his head in shame. She playfully patted
his bottom and whispered,
“You have a lovely bottom that will look lovely in
some frilly panties and perfect for some other pleasures.”
While she still stood behind him she continued to tease
and torment him by reaching up with both her hands and running
her manicured fingers playfully over Steve’s swollen
nipples and massaging his fleshy breasts causing him to
give out a gasp.
“Hmmm, my oh my, you have lovely breasts that are
even more sensitive than a woman’s, an added bonus
is that they are fleshy enough to almost fill out a bra,
without even adding some padding. Only a true sissy would
have such girlish breasts. Are you a virgin Stephanie?”
“No, Mistress I am not”, he responded in an
insulted tone.
“Oh you silly thing, I think you may have misunderstood
the form of virginity I was referring to”, she said
with a little chuckle.
Mistress walked over to her dresser, picked up a wooden
hairbrush, playfully patting it against the open palm of
her hand. Steve was now looking up and admiring her beautifully
rounded bottom. Without turning around to face her perspective
maid she began a short but stern lecture.
“In my advertisement I mentioned that I expect perfection
and in order to begin our relationship on the proper footing
I am required to maintain consistent control by administering
correction for all faults so that they never happen again.
Unfortunately, you have put me in a position where I must
correct a problem already. I asked you to pull a piece of
paper from my crystal bowl earlier that is what I call my
“Punishment Bowl”. Your punishment will consist
of whatever is written on the slip of paper. Before our
next session you will be required to prepare twenty slips
containing various forms of punishment that you think would
be appropriate for various misdemeanors. Now I am going
to assist you with putting you in this girdle and stockings,
the remainder of your uniform you can do yourself. Once
properly attired, you will present yourself to me for inspection
and your first taste of correction.”
Mistress smiled to herself when she saw that “Stephanie”
was sniffling softly, she ignored him and proceeded to slip
him into the open bottom girdle, then attach his sheer black
stockings to the garters. A playful slap on the bottom followed
and without a word Mistress left the room while he quickly
got dressed. Once all the clothing was on, he caught a glimpse
of himself on the full length mirror, although he was clearly
male in facial features, the bra, filled with silicone breasts
combined with the girdle and finally the very short skirt,
complete with puffy crinoline, gave him a sissyish look.
He teetered out into the living room, curtsied as required
and presented himself for inspection. He stood perfectly
straight, with his head bowed and his arms as his side while
Mistress Enya carefully inspected every detail of his uniform
for what seemed like ten minutes.
Finally she broke her silence, “Very well, you may
go put on the water for my tea as well as prepare a proper
tray for my enjoyment, then while the tea is infusing, you
are to report back for your punishment.”
Stephanie quickly retired to the kitchen and readied the
tea and tray with selection of baked goods he prepared.
Although there were nagging fears in the back of his mind
he was amazed at how at peace he felt with serving such
a beautiful woman who commanded both respect and devotion.
In less than thirty minutes he learned what it felt like
to be in the presence of a Goddess. Once the kettle was
turned on, he straightened his uniform and returned to the
living room, thankfully, he remembered to curtsy as he entered.
His only error was that he had left the slip of paper in
the washroom with his “boy” clothing. Mistress
Enya was clearly annoyed when informed of his over sight
as she merely pointed down the hall.
Stephanie dashed as quickly as he could in his heels, then
to make matters worse, he couldn’t find the slip of
paper, the sound of Mistress’ heels clicking on the
floor towards the washroom created panic in his heart, then
when they stopped, he sensed she was behind him and he dreaded
to look.
“Is there a problem?” she snapped.
Before he could respond, she grabbed him by the ear as
if he were a child and lead him into her room.
“Turn around, face that mirror, lean forward and
place your hands on your knees. I want you to see your own
face as you receive your first punishment.”
He felt a shiver through his body as he felt Mistress Enya
flip up the back of his uniform to expose his ruffled panties,
then without a word, she placed one hand against his back
while the other lightly caressed his panty covered bottom,
slowly worked it’s way down to the tender part of
his naked thighs and stocking covered legs. Just when he
was beginning to relax and enjoy the tenderness of her touch,
he saw her reflection in the mirror as she raised her hand
and delivered 5 or 6 solid smacks on his pantied covered
bottom.
Stephanie squirmed and yelped as her smacks suddenly transformed
the loving gentle touch of seconds ago to sheer pain. She
stopped for a moment causing him to think that she lesson
was over, but once again that momentary sense of relief
was shattered when she roughly grabbed the waistband of
his panties and yanked them down around his ankles.
“Oh my goodness, you are such a baby!! Be quiet or
I’ll stuff those panties into your mouth and give
you a spanking that you’ll never forget. Do you understand?”
Stephanie sniffled and nodded and once again the spanking
continued with 10 more smacks on his bare bottom. The whistling
of the kettle most certainly saved him from a longer spanking.
“Pull your panties up and serve the tea for me in
the living room when I arrive.”
For the next few minutes Stephanie waited in the kitchen
with everything prepared but his Mistress did not arrive.
He could hear rummaging in her room but that was all, she
retired to her luxurious sofa and rings a small bell signaling
him that she was ready to be served .She appeared pleased
by the effort he made in providing some small desserts for
her to enjoy with her tea. Once her cup was poured, she
instructed him to kneel at her feet. Once she finished her
first cup, he refilled, then she said in a more loving tone,
“Stephanie you may worship my feet and legs, I will
leave it to you to decide on what will bring me the greatest
pleasure.”
He did his best by combining both gentle kisses and caresses
to her feet, which were still clad in gorgeous heels and
her calves were amazing! She appeared to enjoy the attention
and as he approached her knees she parted her thighs signaling
him to kiss and caress her luscious, stocking covered thighs.
His penis was on the verge of exploding and he just about
lost it when she said softly,
“Lean back and close your eyes I have a special
surprise for you.”
As she said this, she stood up, there was the unmistakable
sound of her unzipping her leather and of her stepping out
of it. Stevie could only dream that he was going to be given
the opportunity to worship this Goddess in the most intimate
way. Even though his eyes were still tightly closed he could
sense that she was moving closer and he opened his mouth
slightly, at that moment she took his head between her hands
guiding it closer to her body.
“It’s time to worship me, you may open your
eyes and mouth.”
As he did she forcibly filled his mouth with the strap-on
dildo she had slipped on under her skirt while following
that initial spanking. He struggled for a moment, but there
was no use and for the next while he received lessons in
how to service a cock.
Eventually his Mistress allowed him to a “release”
with the warning that he must catch it all in his hand or
suffer the consequences. He reached an intense orgasm and
was relieved that none had escaped but that relief was short
lived because he was ordered to smear his cum onto the head
of her strap-on dildo and then lick it clean. Once complete
she added,
“Some day soon these lessons may come in very handy.”
To be continued………..
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