Chrissie The Saga of a Lovestruck Sissy Maid
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A Lady's Sissy Maid free porn video
A Lady's Sissy Maid
By Steve Andrews
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
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 (466) 555-2323
to arrange for an appointment.
The 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 dark 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 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 please 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 to 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 curtsey 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 and
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 and 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 curtsey 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 and 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 when he
saw her reflection in the mirror as she raised her
hand and delivered 5 or 6 solid smacks on his pantie
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 lord 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. He 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 then once she finished her first cup
that he refilled 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. 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 he 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...
Bree
- 25.09.2021
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