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From: "Ted E. Bear" <tedebear690@yahoo.com>
Subject: Maid to Pay (F-dom, Sissy, Gambling Debt)
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Ted E. Bear Repost
Note: The story below is from my archives.
*********************************************************
Warning: This story is a work of adult fiction, and
should be treated as such. It contains graphic sexual
descriptions and possibly some violence. If you are a
minor or are easily offended by this type of content,
then please read no further. Delete it NOW!
*********************************************************
Ted E. Bear
*****************************************************
The following story is posted for the entertainment of adults. If you
are
below the age of eighteen or are otherwise forbidden to read electronic
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These stories have not been written by the person posting them. They
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The copyright of this story belongs to the author, and the fact of this
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=====================
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*********************************************************
Ted E. Bear
*****************************************************
Maid to Pay
Damned, the pressure was building. I knew I had a problem with
gambling, but I couldn't shake the disease. The more I fought it, the
more I would wind up increasing my debts...so much so, that I was
beginning to worry about some goon knocking on my door to explain
orthopedic procedures, concerning my kneecaps, to me.
Let me tell you more about myself. I am an average guy in his
middle 30's with a beautiful wife, two wonderful children and a very
successful job. I am not bad to look at, and have a normal sex life. In
short, I had it all - but I also had a terrible disease. The disease was
called gambling. I knew how stupid it was, building up large debts to
very unsavory people. I had tried counselling, gamblers anonymous and
all the other things that guys like me try, but to no avail.
Fortunately, because of my income level, I had successfully hid my
problem from my wife and my employer. However, that was becoming more
and more difficult, and it was inevitable that someone was going to find
out. I was becoming a nervous wreck!
Then one morning, I received a phone call that was to cure my
addiction completely. As I answered the phone, a gruff voice came on the
line. "I want you to call 555-3421 immediately", the unidentified voice
said, "You will make an appointment with Ms. Elaine to discuss ways for
you to eliminate the debt that you owe my organization. Do it now, or we
will find less subtle ways to eradicate what you owe us!".The caller
then abruptly hung up.
With my voice quavering, I did as I had been instructed. When a
very sultry female voice answered, I identified myself and asked for Ms.
Elaine. "Oh yes, Charles, I have been expecting your call" the voice on
the other end of the line replied, "please be at my office at 3:30 this
afternoon". Ms. Elaine then gave me the address and admonished me,
"Charles, please do not be late. You are in very serious trouble, in
fact life-threatening trouble, and I am your only hope in helping you
extricate yourself from that trouble". Stammering, I assured Ms. Elaine
that I would be there, and on time.
The rest of the morning seemed to drag on, but I made it through,
grabbed lunch, and left a little early to insure that I would not be
late for my appointment. The address turned out to be a prestigious
high-rise apartment building. I took the elevator to the penthouse
apartment and knocked on the door. As the door opened a man,
obviously the butler, ushered me in. He told to sit down and be
comfortable , and Ms. Elaine would be right with me.
As I sat there, a nervous wreck, I noticed magazines lying on the
coffee table. They were very bizarre - all seemed to be centered on the
same theme, that of female domination. As I looked at the magazines, Ms.
Elaine walked into the living room.
"Hello Charles, I see you have noticed my magazines. I hope you
like them". I was astounded! She was absolutely stunning, with dark
chestnut hair, deep brown eyes and dressed in a leather mini skirt, a
red satin blouse and VERY high black patent leather heels.
"Well, Charles, you seem to have a problem with a certain
organization, and they have enlisted my assistance in liquidating the
very large debt you have accrued. Do you wish my assistance, or would
you prefer they take care of the situation in the 'old fashioned' manner
which they are quite good at." My voice quivering, I started to talk.
"Elaine, I would...."
WHACK!
My face stung, and I was shocked as she slapped my face. "DON"T YOU
EVER PRESUME TO CALL ME ELAINE AGAIN", she screamed, "YOU ARE TO CALL ME
MISTRESS ELAINE, AND WHAT I SAY, YOU WILL DO"! "Uh yes, Mistress
Elaine", I stammered, "I shall do whatever you wish". Cowering under
austere look, I felt like a little boy being reprimanded. Mistress
Elaine then ordered me to lay face down on the coffee table. She slid my
trousers and my briefs down and proceeded to cane my bottom until tears
were streaming out of my eyes. "Mistress Elaine", I pleaded, "I will do
anything you desire...ANYTHING... please don't let them hurt me"!
"That's better, Charles", she cooed,"As you might be aware of by
now, I am a professional dominatrix, and enjoy beating a submissive
male's ass until it is nice and pink".
"Mistress Elaine", I whimpered, "If your wish is for me to submit to
your lash, I will be here whenever you order me to be here. I just want
to pay off my debts and get rid of my gambling fever", I blurted out.
"Silly boy", she exclaimed, "Do you honestly think you can work
your debts off by submitting to my spanking! Men, more successful than
you, pay me large sums of money, just for the privilege of kissing my
heels and having me whip their asses red. What I need, is an assistant
to add to the special needs a few of my more affluent clients have, and
are willing to pay for".
She continued, "I have a need for a french maid to help meet these
special requirements, and you may be able to help me in filling this
position!".
"But Mistress Elaine", I exclaimed, "I don't know any women that
would be suitable for this position"!
"Oh Charles, you are so naive. YOU are ideal for the position, and
I think you will just look too sexy and cute for words, by the time I am
finished with you. Besides, those special clients I mentioned, will be
willing to pay double the normal fee I charge them to have the maid
assisting me."
"From now on", she continued, "You are to plan on spending Tuesday,
Wednesday and Thursday evenings here as my maid. You will simply have to
tell your wife that you are travelling on business those three days,
every week." She continued, "and, since this is Thursday, there is nor
reason you shouldn't begin your new duties immediately!"
Mistress Elaine then rang for the butler. As he entered the room,
Mistress Elaine introduced me to him.
"Robert, this is our new french-maid, Cissy". Robert looked at me
with a big smile on his face. "Nice to meet you, Cissy, welcome to
Mistress Elaine's team". I was totally humiliated, standing in front of
Mistress Elaine, while this very masculine man referred to me
as "Cissy". I stammered hello to Robert, my face burning in
embarrassment.
Mistress Elaine then put a collar around my neck, attached a leash
to the collar and led me into her "studio". Robert accompanied us, all
the while maintaining a leering grin on his face. Mistress Elaine's
studio was equipped with all sorts of unusual devices, obviously
constructed solely to restrain her clients in various positions.
Mistress Elaine ordered me to the center of the studio. She ordered me
to undress completely, while the butler continued observing my
embarrassment. Mistress Elaine then cuffed my hands together. She then
clipped the cuffs to a cable coming from the ceiling. Robert then drew
the cable tight so that I was standing on my tip-toes, helpless and
totally exposed.
Mistress Elaine turned to the butler,"Robert, I have a client
coming at 7:00 and another client at 10:00 tonight. They both have
special requests and will pay double the normal rate. We have enough
time to dress Cissy appropriately, but I will need your assistance."
Robert shook his head in agreement. Mistress Elaine then took a
bottle of depilatory and began to apply it to my entire body from the
neck down. I was really embarrassed as she rubbed the lotion all over
me..not missing a spot. As she smeared the lotion on my pubic area I
started squirming in my restraints and cried out at the humiliation I
was undergoing.
WHACK!
The sharp sting on my buttocks was like a hot iron, as Mistress
Elaine applied her whip to me.
Whack! Whack!
"STOP YOUR SNIVELLING NOW, CISSY!", Mistress Elaine yelled at me,
"This is just the beginning! You are going to be my resident party doll,
and you will be as feminine as possible, yet everyone will still know
that you are nothing more than a sissy boy, dedicated to pleasing me and
my clients!".
I stopped my squirming, knowing that I was helpless to prevent what
was happening to me. Finally, she finished applying the depilatory
lotion, and they both sat down waiting for lotion to do it's work. After
fifteen minutes, Mistress Elaine had Robert uncuff me and led me into
the bath where she told me to rinse myself completely. Robert then
handed me a towel and I dried myself completely. I was led back into the
studio and again cuffed in the same position.
Mistress Elaine the place a heavily boned red satin corset around my
torso and snugged up the laces. She then had Robert tighten the laces
until the corset was fully closed. It felt like my body was in a vise! I
could hardly breathe! "Oh look at Cissy's cute little figure", exclaimed
Mistress Elaine, "She is going to look so cute in her little uniform!"
Mistress Elaine then slid sheer black, seamed stockings up my hairless
legs and attached them to the garters on the corset. She then slid a
pair of very frilly lacy black panties on me and a black lace bra.
Robert placed a pair of silicone filled pads in the cups of the bra,
while Mistress Elaine forced a pair of black patent high heel shoes on
my feet. The shoes were murder!...the heels had to be 6" high and I
found myself in great difficult just standing in them. I realized that I
was going to have to walk in mincing little steps just to keep my
balance!
Robert then removed handcuffs. As I stood there heavily corseted,
in panties, bra, stockings and high heels, I felt totally humiliated, my
face burning in shame. "Oh isn't Cissy cute, Robert!" exclaimed Mistress
Elaine, "Won't our clients just love the added pleasures that she is
going to provide"!
Mistress Elaine ordered me to mince around the studio as she and
Robert went into hysterics, laughing at my degradation. "Enough
playing", I have clients coming and I want to finish dressing Cissy
appropriately", she said.
She then ordered me to sit down, while she deftly applied
foundation, blush and the proceeded to outline my eyes with jet black
eyeliner. Several shades of blue eyeshadow were applied and a heavy
application of bright red lipstick. Mistress Elaine then coated my
fingernails with a bright red polish that matched my lipstick. She
completed the make-up session by clipping a pair of large dangly
earrings on me.
"Stand up Cissy, let's see how you look", said Mistress Elaine. I
did as she ordered, knowing what a sissy I looked like. Mistress Elaine
then took out her camera. "A few pictures of you, before I place your
wig on, posing, dressed as a sissy boy, will give me even more
insurance
that you will do as I say.
"Click Click" - the sound of the camera brought tears of shame to my
eyes. "Now, kneel down Cissy, I want a few more pictures of you ... with
Robert in the photos as well".
"No", I screamed, "Please not that"! Robert grabbed my arms and
forced me to my knees.
"Now, Cissy, is that anyway to treat poor Robert who has been so
helpful in turning you into the sissy boy you really are?", said
Mistress Elaine, "I think you should show your gratitude to him. Suck
his cock now"!
I was helpless! Robert unzipped his fly and I was shocked at the
size of his penis. It had to be 10" long and very thick. With absolutely
no foreplay, he thrust his cock past my lips into my mouth. Placing his
hands behind my head, he forced himself deeply into me, fucking my mouth
as if it were a hot vagina. I tried not to gag, and then I heard the
sound of the camera again! "Oh no, she is taking pictures of me again",
I thought, "She can blackmail me to do anything she wants me to do".
Robert increased the tempo of his pumping. I could feel the head of
his cock starting to throb, then Robert suddenly pulled his cock out of
my mouth.
Mistress Elaine quickly grabbed it and started pumping his cock,
aiming it at my mouth.
"Open wide, Cissy!", she said in a husky voice, "You are about to
receive a nice hot load of cum, your first of many!"
Robert suddenly moaned in ecstacy as she continued to pump his
cock and then..the shock of hot sperm shooting on my face, t my lips,
into my
mouth and on my tounge.
Mistress Elaine continued to aim his cock so not a drop was wasted,
then thrust it back into my mouth, so it acted as a plug!
Mistress Elaine started stroking my throat, as Robert continued to
fill my mouth with his cum. "Swallow Cissy", she said in a taunting
voice, "You are going to have get use to having men use your mouth as a
sperm depository". Robert kept his cock in my mouth while Mistress
Elaine continued stroking, until I swallowed every drop of his cum.
"Oooooo, very good, Cissy", squealed Mistress Elaine, "I am sure
that will you become a superb cocksucker and my clients will be
delighted to pay extra for your services"!
Mistress Elaine then ordered me to sit at the make up table again.
She freshened my lipstick, then placed a long, chestnut brown wig on my
had, teasing it and adjusting it until she was satisfied.
Finally, she slipped two frothy taffeta petticoats over my legs and
up to my waist. Then came the uniform. It was black satin, trimmed
around the sleeves and the bodice in white lace. The skirt was very
short and it stood out almost straight from the petticoats underneath. A
white lacy apron and little hat added the finishing touches. As I looked
in the mirror, I was amazed! The addition of the wig, coupled with the
french maid uniform, made me look very sexy indeed!
Mistress Elaine grabbed my hand and led me to the living room.
"Cissy, I have two clients tonight. The first, Mr. Lane, will be here
in about 20 minutes.Mr. Lane has a craving to be dominated and
humiliated. You will assist me in his humiliation. He will be
restrained, and as he becomes aroused from the taste of my paddle, you -
my little sissy boy - will caress him, and tease him by rubbing your
satin clad body against him."
" When he becomes really hard, you will kneel before him and start
sucking and licking his cock, as I continue spanking him."
"Just before he cums, I shall remove your wig so he will
experience increased humiliation receiving a blow-job from a sissy boy
in petticoats."
"For his ultimate humiliation, I shall hook you to his crotch
harness to he will not be able to pull his cock out of your sissy mouth,
while I spank him to a second orgasm!"
Mistress Elaine continued, "My second client , Gary Davis,is
exactly the opposite. He is quite dominant and has the fantasy of
humiliating and degrading his tyrannical boss.I will play the role of
his secretary, and you, my dear Cissy, will play the role of his boss!"
"As part of the scenario, I have blackmailed his boss into doing
anything I want him to do.
When Gary walks in, you will be dressed in a frilly pink taffeta
party dress, little pink bows in your hair, and frilly pink panties but
with high heels and nylons - so you are a hooker's parody of a little
girl!
Gary intends to have me restrain you so he can fuck your lipsticked
mouth and jerk off on your face while I take photos for him to show the
girls at the office". You will be our total sissy toy to play with,to be
used and humiliated as we see fit.
Since he is the last client of the evening, and tips me quite will,
you may find yourself spending a great deal of time tonight, with your
lips wrapped around his cock!!
As I sat there, waiting for Mistress Elaine's first client of the
evening, I felt trapped. I knew that I had to do exactly what Mistress
Elaine ordered me to do, and that most of those things were going to be
extremely humiliating. I was now her sissy boy, her french-maid, her
submissive little girl, and, worst of all, her sissy cocksucker.
THE END
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