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My Sister-in-Law's Maid

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gwalton

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Posts: 16
#1
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It all started when I decided to be a big shot and hire a petite,
pretty maid named Brenda. I have to admit that I was an arrogant, stupid fool. I
thought I had the world by the tail and that I could do whatever I wanted. I had
a very successful career as a partner at a law firm and a relatively meek wife
who had no real control over me.

Shortly after Brenda started, my wife Julie caught me making a pass at our maid,
and the tables were turned on me. Julie threatened to divorce me unless I agreed
to take a more subservient role in our relationship. Since I had foolishly
neglected to have Julie sign a pre-nuptial, she could take half of our assets,
amounting to at least five million dollars. So in order to repay Brenda for my
brutish behavior I was required to assist her whenever she asked. Thinking I
could easily handle whatever menial tasks she might ask of me, I readily agreed.

In the beginning, Brenda just occasionally asked me to help out in her duties
around the house, doing dishes or the laundry. Surprisingly, I actually found
such jobs to be a welcome respite from my usual high-tension lifestyle and
became quite agreeable to her requests. But as time went on, she became bolder
in her requests that were actually becoming more like commands. In fact, she
even started to ask me to do permisteral service for her, like shining her shoes
and hand washing her panties.

When I complained to Julie that I thought Brenda was going too far, she slapped
me across the face. "Don't you dare disobey a request that our sweet maid makes,
not after the horrible way you treated her!" Brenda was told that I would do
anything that she asked, no exceptions.

It took Brenda a little while to come to grips with the new power she held over
me, but she slowly and steadily deepened the level of my servitude. She began to
require that I do more and more of her maid duties when I was at home. Then one
day she added a new chore to my list - I was to waken her each morning before I
left for work by gently kissing her toes. A few days after I reluctantly
accepted this task, she upped the ante by telling me that once she was awake I
was to take each toe in my mouth, one at a time, and suck on it. If I didn't
show a sufficient amount of enthusiasm, she immediately kicked me in the face
and threatened to inform Julie of my misbehavior.

After a few weeks of this, I became quite proficient as sucking her toes and she
started to get aroused from my administrations. I have to admit that I got a bit
aroused too. At first I thought it was just my imagination, but then I realized
that she was actually starting to masturbate while I sucked on her pretty feet.
There was no doubt left at all when she started to scream out while having an
orgasm one morning. When Julie came into Brenda's room to see what was
happening, she just snickered and went back to bed. From then on, I was not
allowed to leave for work until I had sucked Brenda's toes long enough for her
to have two or three earth shattering orgasms.

Over time, my subservience deepened in many ways. Brenda eventually took my wife
as her lover, and before I realized what was happening I had been turned into
their well-trained sissy maid. I was kicked out of our master bedroom to make
room for Brenda and made to relax in the smallest bedroom, which was done over
in a very feminine style. While Julie and Brenda enjoyed what they agreed was
the best sex they had ever had, I was gradually cut off from my wife's pussy and
had to satisfy myself by masturbating. When Julie realized that I was spurting
five or six times a day she acted like she was offended. I tried to explain that
being subservient to them and denied sex with my wife had made me extremely
horny, but she decided that something had to be done to control my obsessive
urges.

Julie's solution resulted in yet another major change in my life. She purchased
a cock harness made of metal rings held together by leather. It was called the
Gates of Hell and I could understand why. Once she made me put it on there was
no way I could get a full erection. Whenever my cock tried to grow, it would
painfully bulge out between the metal rings, preventing any enjoyment at all.
There was no way I could masturbate with the terrible thing on and I couldn't
remove it without the key, which Julie kept hidden away. I knew I should have
resisted having it put on me, but for some reamister I found it somewhat erotic to
be controlled in such a way.
Blumoxey

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Posts: 59
#2
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That's a hot start to a good story, hoping to hear more.
gwalton

Member

Posts: 16
#3
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One evening Julie had me attend to her while she was dressing to take Brenda out
for her birthday. As I was helping her put her shoes on, Julie spread her legs
and indicated that I should lick her pussy. She laughed as my cock strained at
the harness and said she wished she could release me, but didn't have the key.
"You see", she said, "I asked Brenda what she wanted for her birthday and she
said she wanted your balls, so I gave her the key. Since I don't have any need
for your cock anymore, I thought it was an appropriate gift. Now get back to
licking me, and don't stop until I come".

Brenda thoroughly enjoyed having me under her control and gradually increased
the time between allowing me release from once a day to once a week. In the
meantime she and Julie were having orgasmic sex sessions three or four times a
day. To make things worse, I was only allowed to masturbate in the presence of
Brenda and Julie. Actually it was for the entertainment of them since they
delighted in teasing me while I masturbated, letting me get to the point of
almost coming, then stopping me until I calmed down before starting the cycle
all over again. I was devastated with offense, but so desperate to come that
I would endure anything.

Eventually, my wife Julie decided it was beneath her to be married to a sissy
maid and informed me that she was going to divorce me. She told me not to worry
because nothing was going to change in our relationship. I would still be her
sissy maid and stay in the small bedroom, but she just didn't think it was
proper for her to be married to her maid. She said that if I insisted on staying
married to her, that she would no longer allow me to be her maid and I would
have no contact with her at all. She was very insistent and I reluctantly had to
agree to her decision.

Julie then reminded me that the disposition of our property would have to be
settled for our divorce. She pointed out that it was obvious a simple maid was
not qualified to manage the substantial assets we owned. So it was decided (by
her) that she would get ownership of all of our property. I had already given in
so many times that I just didn't have it in me to disagree anymore. In the end,
she walked away from our marriage with over ten million dollars, which I had
spent 20 long, hard years working and investing for. She told me that she would
be kind enough to allow me to keep my maid outfits, but all my male clothing
would be given to charity since I had no further need for it.

"But how will I go to work if I don't have any suits to wear?" I asked. Julie
just gave me a grin and told me that she and Brenda didn't need me making money
anymore since they were now set for life with my ten million. Thus it was also
decided that I would retire from my well-paid position so I could serve them
full time. Of course, I was then required to sign over my lump sum retirement
check of two million dollars to Julie since I would not need any money in my
position as their sissy maid. I was also required to turn over the three million
dollar settlement I received when I left the law partnership. I was then
informed that since I no longer had a job taking up part of my energies, I would
be expected to perform twice as well and twice as hard as before.
studmaster58

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Posts: 423 Pictures: 6 
#4
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Sexy story, what a hot ending...........
gwalton

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Posts: 16
#5
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One fateful day Julie's sister Jessica was over for dinner. As usual,
I was dressed to the nines for the occasion, wearing my best pink French maids
outfit. Jessica always insisted that I look my best for her visits, even though
she made it obvious that she despised me. In fact, she was the one who had first
suggested that I wear a maid's uniform. "After all," she had pointed out, "if
she is going to behave like a sissy maid, she should dress like one too". For my
birthday present, she gave the pink maid's outfit to me, complete with garters,
6 inch spiked heels and a perky cap for my head. When I was powerd to model it
for the amusement of the 3 women, I discovered that the dress was a size or two
too small. When I complained that I couldn't squeeze into it, Jessica told me to
open the other present she gave to me. When I opened it, I found a severe
looking black corset. Brenda volunteered to help me into it and seemed to relish
pulling it in as tight as possible. I could hardly breathe with it on, but I did
fit easily into the maid's dress.

Jessica was an evil power of nature that no one dared oppose, so Julie and
Brenda agreed that I would do everything possible to please her when she came to
visit. I would eventually come to learn just how evil Jessica could be.

Actually, Jessica was impossible to please and had a terrible temper, but there
was one other aspect to her that had caused me to overlook these warning signs -
she was drop dead beautiful. I was completely infatuated with her. In fact, I
think one of the reamisters she held me in such low esteem was that it was so
obvious that I lusted after her. When I was in her presence I couldn't help but
stare at her gorgeous figure. Many times she had caught me staring at her long,
trim legs and perfectly proportioned feet. She always wore very high, mean
looking stiletto heels in bold black or red colors. I positively drooled when I
was able to catch a good long look at her shoes. And the micro short skirts she
wore along with the tight blouses that accented her 38D breasts always made my
heart race. Sometimes I suspected that she intentionally dressed up just to
tease me. Perhaps that is why she insisted that I dress up too.

Although I looked forward to being able to gaze upon the Goddess Jessica, I also
dreaded her visits because I had to spend three days beforehand working like a
slave cleaning the house to come even close to meeting her standards. If she
found dust on anything she would show her distain and disapproval in such a way
that Julie would be mad at me for a week. Julie had never been able to meet her
big sister's standards either. I also had to spend hours doing my makeup and
hair. Jessica said that she refused to tolerate a maid who couldn't maintain an
acceptable appearance. She also insisted that it wouldn't be proper for me to
speak unless asked to while I was doing maid service.

Brenda seemed very quiet on this particular visit and Jessica asked why. Brenda
said she was depressed because she couldn't afford to buy the yacht she wanted.
It only cost $100,000, but the seller wanted the money within the next week or
he would sell it to another buyer. The money I had 'donated' to support Julie
and Brenda in the manner to which they were accustomed was tied up in various
investment vehicles, so she had only been able to get $75,000 together.

At the mention of vehicles, Jessica broke out in a smile and said she might have
a solution. She offered to help out by buying the Maserati I treasured so much,
but would only pay $20,000 for it. I knew the classic was worth at least ten
times that much, but was too cowed by these women to argue. Jessica could afford
to pay it; she was quite well off since Julie had been generous enough to give
her the two million dollars from my retirement funds in an attempt to win her
favor. She then made the offer that was to change my life forever. "I'll give
you the other $5,000 if you'll let me have Missy as my evening maid for the next
six months."

Brenda seemed excited about the proposal, but said that she didn't want to give
up the services of her maid, so she and Jessica decided that they would share
me.

Jessica said "I'll be paying a fairly high rate for her services since she'll
spend the first 8 hours of the day here before putting in 8 or 10 at my place,
but I'll just have to work her extra hard and expect perfect service in return.
I think it would only be fair if she served me all seven days of the week and of
course, I'll have to take extreme measures if she doesn't perform to my exacting
expectations."

At this point Julie interrupted the conversation and I thought I might be saved
from a horrible fate. She agreed that Jessica was offering a generous rate for
my services. But she said that I should agree to the arrangement also before the
deal was sealed. Julie pointed out that when I had signed all my assets over to
her, she had promised me that my status would not change, so this arrangement
wouldn't be fair to me unless I agreed to it.

I had no intentions of considering such a deal until Brenda took out the key to
my cock harness and said that she thought she had been too lenient with me and
that from now on the time between my masturbation releases would be doured each
time - first two weeks, then four, then eight, sixteen, thirty-two, etc. This
would mean less than five releases in the next year and only one the following.
She then said that since Jessica was so generous about my pay rate, maybe she
would also be generous about my masturbation schedule.

At this point, Jessica stretched out her gorgeous legs and asked me if I
wouldn't take off her heels and give her a foot message while she thought this
over. My cock immediately jumped to attention, only to be cruelly held back by
my harness. My hands were shaking as I carefully unstrapped her erotic high
heels and slipped them off her lovely feet. The sharp aroma from her leather
encased feet made me swoon. As I took one of her feet in my hands, she
intentionally spread her legs a bit so I could catch a glimpse of her crotch,
which had no underwear to block my view.

Jessica then giggled and said "Sure, I'll even start out allowing Missy a
release every night and I guarantee I won't change the schedule for at least a
week until I can gauge her performance. If she promises to try her hardest, the
daily releases will continue". Then, giving me a very seductive smile she asked
me if I wouldn't please agree to help her out. I was insane with lust and the
thought of spending 8 hours or more a day in the presence of Jessica made me
dizzy with longing. I slowly nodded my head in agreement.

Jessica then made it very clear what I had just agreed to. "I want you to
consider what you are accepting," she said as she actually rubbed my poor cock
with her heel. "You are trading six months of maid duty for a week of jacking
off. Are you sure this is what you want?" she asked sweetly. I was so horny I
would agree to anything and besides, I figured if I wasn't serving her I'd be
serving Brenda or Julie anyway. And since I had been stripped of all my assets
and positions, I had no other way of making a living. "OK," Jessica said, 'but
I'd better not ever hear you complain about our arrangement since you have
freely agreed to the terms".
gwalton

Member

Posts: 16
#6
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The six months turned into twelve months because I had difficulty measuring up
to Jessica's standards and she had to cut my pay rate in half. In fact, I was
required to spend the second six months at her house full time because my hours
were also doured. Actually, since Jessica no longer had to work due to her
newfound fortune, I was on duty 24 hours a day, seven days a week. True to her
word, Jessica allowed me to jack off each night for a week. But on the eighth
night I was informed that until I started measuring up to Jessica's standards, I
wouldn't be allowed to jack off again. As it turned out, I had more orgasms in
the first week than I did in the following year.

Although I was required to stay at Jessica's house around the clock for the
second six months, I didn't have to move out of the mansion that Julie and I had
spent our married life in. As it turned out, Brenda and Julie enjoyed the yacht
so much that they decided to move out of the mansion and live on the yacht.
Jessica had always admired the huge mansion her sister lived in, so Julie signed
over the title to her. Jessica had told her she would write off three months of
my servitude in return, but eventually she added the three months back on due to
my poor performance.

The day that Jessica and I moved back into the mansion turned out to be one of
the most degrading events of my life. Jessica seemed to be intent on making it
obvious to me that my status in the mansion was not going to be the same as when
I was lord and master. For starters, she made me get in the trunk of the
Maserati for the ride over. She said that I hadn't earned the privilege to ride
up front in the car with her. When we pulled into the mansion's garage, she
opened the trunk, but didn't let me out until she had attached a collar and
leash around my neck as if I were but a dog. After I stepped out of the trunk
she then made me take off all my clothes and get down on all fours. She then
picked up a riding crop from the back seat of the car, warned me that I would be
sorry if I wasn't a well-behaved puppy for her, and yanked on my leash as she
strolled towards the house.

From my vantage point low to the ground behind Jessica, I had an incredible view
of heaven. She towered above me on a very sexy pair of alligator high-heeled
sandals and walked with a magictizing sway of her perfect ass. She was wearing a
tight, black leather skirt with a skimpy red halter-top that barely held up her
perfect boobs. The urge to trot along behind her to maintain my view easily
overcame my reluctance to accept the way she was treating me. However, once we
entered the foyer of the mansion, I once again recoiled against the offense
of being treated like a dog in my former home. She quickly put me back into my
proper place with a half dozen sharp blows to my ass with her vicious crop. Then
Jessica began her tour of her new home with her obedient dog in tow. To keep
reminding me of my new status in the mansion, Jessica had me lick the soles of
her high heels clean before we entered each room. She also spent some time
training me how to heel and keep my gaze straight ahead while she was walking
me. "You had better learn quickly how to be an obedient doggie, because I'll be
walking you every day from now on", she said gaily, as she strolled along.

As we went thru the mansion, Jessica helped herself to my stores of fine
cigarettes, wine and caviar. Of course I was no longer allowed such luxuries,
but she didn't totally deprive me. When we reached the kitchen she said she
would find something appropriate for me to eat. As I kneeled on the floor at her
feet, I could hear her opening a can and spooning something out. Then she leaned
over and put a large bowl of dog food on the floor in front of me. "My doggie
had better eat all her food quickly, or I will have to correct her behavior
again" Jessica said as she gave me another crack on my ass with her crop. The
blow stung so bad that I took a bite of the dog food before she had reamister to
apply another. The food stunk terribly, but I knew she wouldn't allow me any
option other than to eat it all.

I will always remember that defining moment. As Jessica sat on a comfortable
chair, eating caviar on crackers and sipping at an expensive Bordeaux, I
shivered naked on the kitchen floor of my former mansion, gagging as I struggled
to eat the terrible smelling dog food she had served me. Every once in a while,
as she tugged on my leash, I would look up to see the triumphant smile of
victory on her face. "You better get used to the taste of that dog food", she
told me, "it is the only food you will be allowed anymore".
slippery el

Member

Posts: 98
#7
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reallyyyyy great story
josh hartnett
goodhusband

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Posts: 4063
#8
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Nice imaginative offense. I can't wait to see what you come up with next. This is fun stuff.

GH
gwalton

Member

Posts: 16
#9
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At night, while Jessica nestled in the blankets of the huge king sized bed I
used to relax in, I was stuffed in a small dog crate at the foot of the bed so I
would always be available for service. I could barely fit inside curled up in a
ball, and the metal bars were not comfortable at all to relax on (I was required
to relax in the nude with no blankets). I was confined to the small crate and
couldn't get out until she unlocked the latch because I had disturbed her with
my trips to the bathroom at night. When she decided that I needed to be
confined, all she could find was the small crate previously used for a beagle.
At first I had been provided with blankets and pillows to provide some comfort,
but in her continuing quest to find new ways to punish me, they had been
removed.

Before she went to bed, Jessica usually took a cruise in the Maserati. I was no
longer allowed to even sit in the car because she claimed she didn't want to
take a chance on me messing up the seat's adjustment. However, I was required to
keep it immaculate for her pleasure. Once Jessica had caught me sitting in the
car trying to reminisce about old times. To insure that I would never again
forget her command not to sit in the car she beat me so bad with her riding crop
that I couldn't sit down on anything for a week.

When my mistress went for a drive I would hold the door open as she sat down on
the leather seat. Then before swinging her legs inside, I would have to lift her
feet one at a time and lick the bottom of her shoes perfectly clean so the
carpet wouldn't get any dirt on it. She always wore a pair of sexy leather low-
heeled sandals when driving and she knew it teased me to no end that I wasn't
allowed to touch her toes with my tongue or lips while cleaning her shoes. Then
she would take off for a wild night ride for an hour or two.

While she was gone I had to work on the impossibly long list of chores she would
give me to keep me out of trouble. Of course I was always in even more trouble
when she returned home to find I hadn't finished everything assigned to me. My
tasks were very difficult to accomplish because Jessica found it amusing to
require me to do things like polish the kitchen floor with my tongue. She would
make me video tape myself to insure that I didn't cheat and also because she got
such a kick out of watching videos of me degrading myself. When she watched
these videos I usually spent the viewing session practicing my tongue polishing
s*******s on the high heels she would be wearing. She would giggle as she looked
down at her sissy maid licking her shoes and ask me how I liked cleaning the
mansion that used to be my 'castle'.

Jessica admitted that she also found it highly erotic to drive the powerful car
that I had always been so proud of. She told me it was especially arousing to
know that the car's former owner had licked the soles of the feet of the bitch
goddess who now ruled both the car and former owner. I still remembered what a
feeling of incredible power driving it could give to a permister. That car had been
my pride and joy and now the closest I came to driving it was licking the soles
of the erotic sandals that pressed the pedals.
Razor

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Posts: 491
#10
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Lesbian cuckolding is the hardest to find, and hottest type of domination there is. This story is among the best I've ever read.
Blumoxey

Member

Posts: 59
#11
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To go from master to slave . . . erotic!
slippery el

Member

Posts: 98
#12
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really greattt story
josh hartnett
gwalton

Member

Posts: 16
#13
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When Jessica returned from her drive she was always so sexually excited that I
had to spend three or four hours in oral servitude while she experienced a never
ending series of orgasms. Since I almost never finished the list of chores
assigned to me before her drive, I usually was punished before starting my oral
worship. Her favorite method was to whip my butt until it glowed red and then
fuck me in my ***d ass with one of her cruel double dildos. These dildos
were sized just right on her end to provide her with the ultimate pleasure. In
fact, she usually came a couple of times just from fucking me. She always
insisted that my ass had to be the proper shade of red to get her excited enough
to give me the good, long, hard fucking which I was powerd to beg her for.

My end of the dildo was another story. My goddess said she wanted to insure that
I got as much pleasure as possible from the only kind of fucking I was allowed
to experience. So she had slowly increased the size of my end of the dildo to
maximize my 'pleasure'. Eventually my end was over a foot long and so wide that
I thought it would split me open. The only lubrication she allowed was that
supplied by my mouth, so I also had to give her a good blowjob before she fucked
me.

Naturally, I had to beg for the chance to give her dildo a blowjob too. This
would result in her laughing out loud because she would already be giggling
hysterically from listening to me beg for a good ass-fucking. She found it
hilarious that I would beg to be fucked and seemed convinced that I really
wanted it. Actually, I knew that if I didn't put on a good show of asking to be
fucked then she would use no lubrication at all. So it seemed cruel that I then
had to beg to give her dildo a blowjob in order to slick it up before it went up
my ass.

Of course being cruel to me was what turned Jessica on the most, so she would
get very excited when I started her blowjob. She would buck and moan as her end
was pushed in and out of her cunt, and would then enjoy a good, fast, orgasm
while I gagged so much I thought I was going to fetish to death.

When her orgasm finished she swiftly pulled the dildo out of my mouth and
roughly spun me around so I could bend over for my fucking. She never gave me a
chance to get ready for what was coming, she just rammed the monster right up my
rear end. She claimed she did so to avoid having my saliva lubrication dry up,
but the dildo was shoved up me so fast I don't think it helped that much.

Now that Jessica was actually fucking her submissive sissy maid, she really got
warmed up. She would power me down onto her bed (the only time I'm ever allowed
on any furniture) and begin slamming the dildo into my ass with more gusto than
I could believe a woman could put out. The fucking she gave me would put any
jock to shame.

After my fucking, Jessica would give me the dildo and watch with an amused smile
as I licked it clean. She wouldn't let me linger too long on the thinner end
coated with her heavenly juices, but insisted I couldn't stop sucking on the
much thicker opposite end until it was completely clean.
faraday5

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Posts: 119
#14
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Very exciting. Thanks for sharing. So what about your lady-in-law? It must have been humiliating when she found out what her two little girls had done to you.
gwalton

Member

Posts: 16
#15
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Once I finished cleaning the dildo, I was allowed to beg for the privilege of
worshiping Jessica's ass. She said that since she had put something up my ass, it was only fair that I put something up hers. She would then lay back deep in her favorite leather arm chair and lift herself up by wrapping her lovely legs around my head and planting the viciously sharp spiked heels she wore for this event firmly in my back. I knew that I had to try my best to please her because it was very hard to make her come with my tongue up her ass. No matter how hard I tried, I couldn't get my tongue in deep enough to satisfy her. It didn't help that she handcuffed my hands behind my back to focus my 'concentration'. She usually wound up using her long carriage whip on my ass to give me an incentive to try even harder.

Finally, after an hour or so, she would shudder through a long, slow orgasm that she said was one of her favorite experiences. By this time, my tongue was aching beyond belief and the only thing that kept my mind off it was the fact that my ass felt like it had been turned into ground beef. Jessica would then lead me into the bathroom and pour a cupful of Listerine down my throat so I could gargle with it before beginning an hour or two of pussy licking.

A good, long session of pussy licking was one of Jessica's favorite activities, so she had taken great pains to teach me how to provide perfect service. Of course I was the one who suffered all the pain. During the entire session she would wield her favorite riding crop with which she could administer a fearsome blow to my ass if I made the slightest mistake or showed any lack of enthusiasm. Since I still didn't have the use of my hands it would become incredibly painful to hold up my head while licking her, but as usual, she was more than happy to administer a sufficient amount of pain to my ass to make me forget the pain in my neck.

After licking Jessica to another three or four orgasms she would finally become satiated and move on to the final step of my nightly ***. She would remove my handcuffs so that I could contort myself enough to fit in to the incredibly small dog crate. It couldn't be much larger than a microwave oven, but her standing threat to whip my balls if I didn't immediately get completely inside when ordered to was more than enough incentive to get me to scoot right in. Then she would slam the door shut and lock it. I knew that until she let me out in the morning to fix her breakfast and serve her in bed that I better not make a single sound. There was certainly no chance of release for me till then, not even if I had to urinate so bad I thought I would wet myself.
dudette

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Posts: 53
#16
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This story is AMAZING. It is now my most anticipated aspect of this site. I can't wait to read more! Really good work!!!
gwalton

Member

Posts: 16
#17
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If I didn't have the hope of being returned to my lovely ex-wife Julie at the
end of my sentence I don't know how I could have endured it. But since I had been stripped of everything I had, including my dignity and free will, I really didn't have much choice. Jessica in the meantime just seemed to get happier and more satisfied the longer she had me under her thumb. In a bizarre sort of way, she seemed like a happily married young bride who was perfectly satisfied with her new way of life. She was always smiling, especially when she came home each day with a new bundle of clothes she bought after a day spent shopping and visiting beauty parlors. She spared no expense when it came to pampering herself and got a real kick out of teasing me about spending all my hard earned money.

Jessica got a special kick out of the dressing sessions following her shopping trips. I would attend to her every need as she tried on each outfit. She didn't have to lift a finger because her sissy maid would carefully dress and undress her each time. This would drive me crazy with lust as I would slowly strip her down to her awesome nude form and then perfectly position each piece of clothing as I dressed her again. Jessica kept her wicked wooden hairbrush handy in case I failed in something like making the line up the back up her stockings straight. I think she just preferred to see her hand maiden move about gingerly due to a well beaten, red rear end.

At the end of my year of servitude to Jessica, Brenda and my ex-wife came over to the mansion for the weekend. When the weekend was over they were to take me back to the yacht. When Julie saw me she said she couldn't believe my figure and asked how Jessica managed to get rid of my potbelly. Jessica then motioned me over to her. I dutifully went over to her, curtsied and then knelt to kiss her shoes. When I raised my head from her feet, she held out the dildo gag for me. As trained, I took it into my mouth and closed the lock at the back of my head, holding it in place. As always, I gagged for a few minutes while getting used to having the large dildo shoved down my throat. Since Jessica wore the only key on a gold chain around her neck, the gag wouldn't come off till she allowed it to.

When Julie asked how long the dildo gag was, Jessica told her that I had just graduated to a six incher. "But that is not nearly as big as the eight incher she wears up her pretty rear end. Until last week she proudly kept a seven incher up there, but since it had been nearly a month since she moved up to that size, I decided it was time to move up to eight inches. And best of all, the new one has a five inch circumference and a much wider head on it. Since I require her to always keep it in place, she is getting quite used to it. Although I'm not sure how well she will handle it when we move up to the nine incher tonight."
gwalton

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Posts: 16
#18
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Sorry it has taken me so long to add the next part to this story, I've been very busy with the holidays and things. I also want to thank everyone for their kind words and encouragement.
gwalton

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Posts: 16
#19
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Jessica then continued to explain how she had helped me out with my figure. "Since Missy always wears her gag when she is not in my presence, she has no opportunity to cheat on her diet. Of course, there is one other measure I took to help her achieve her slim waist size of 25 inches, which is quite an improvement over the 42 inches she came to me with. Missy, why don't you show them the beautiful corset which you wear nearly 24 hours a day now".

I then demurely removed the ruffled blouse I was wearing so they could see. Julie and Brenda both gasped when they saw the *** device Jessica had provided me with. Made of red and black leather, with stiff metal boning, the corset was a truly evil thing. At first, I had been required to wear nylon/polyester corsets that were gradually reduced in size as my starvation diet took effect. I had lost 80 pounds in the six months since I started staying with Jessica full time. I was now a slim 140 pounds, down from my former 220. Once I had lost enough weight, Jessica had me fitted with the confining garment which I never forgot I was wearing. I never forgot because it was so tight I could only breathe in small amounts. But I had to admit that the effect on my figure was stunning. The corset even gave me the illusion of having substantial breasts since it pushed my chest up and included water filled bra pads.

Jessica then instructed me to take off my skirt and petticoats so Julie and
Brenda could better see my improved figure. Wearing just my cap, corset, g-string, garters, fish net stockings and the 6 inch high heels locked to my
ankles, I made quite an impression. It also helped that Jessica required me to keep every inch of my body shaved smooth at all times. The only thing not shaved was the long bleached blond hair which now hung over my shoulders. I was even beginning to feel a little proud of my appearance until Brenda commented that it was impossible to tell that that I had ever been a man. When she asked why I showed no bulge in my crotch, Jessica released the chain attached to the back of my corset and told me to remove my g-string. The chain had kept my cock pulled back between my legs, but when I took off my g-string it dropped down with a jangling sound of heavy gold jewelry.

The first thing Brenda noticed was that that Jessica had replaced my leather cock harness with permanent pierced on gold rings which prevented me from ever achieving anything approaching a true hard-on. The gold rings matched the ones mistress Jessica had pierced thru my nipples, except that the large nipple rings each had quarter pound heart shaped solid gold weights hanging from them. But the part which Brenda truly loved was the pair of rings pierced into my scrotum snug up against each of my poor balls. The skin of my scrotum was painfully and permanently stretched tightly around my balls, so much so that the veins bulged out. Jessica had painstakingly (for me) tried out different sized temporary rings thru the piercings around my balls until the perfect size was found which allowed sufficient red flow, but still made for a terribly tight fit.

The net effect of the whole arrangement was that the only way I could come was one agonizing drop squeezed out through my pitifully restrained cock at a time. Even that was only allowed on very rare occasions (perhaps once every month or two) when I demonstrated a new level of deeper presentation or offense for Jessica's amusement. The truly perverse part of this situation was that the more I suffered, and the less I was allowed to experience any kind of sexual gratification (other than providing it to her), the more aroused Jessica became. She had told me that before I began to serve her she only managed to achieve an orgasm maybe once a month or so. Now that she could tease and *** me to her heart's delight, she was having multiple orgasms six or more times a day!
gwalton

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Posts: 16
#20
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One of Jessica's favorite way of coming is to have her subservient sissy maid lick her for an hour or two, then she begins to orgasm like gangbusters. Unfortunately for me, when she gets that excited she likes to get her riding crop out and blister my ass, especially if I dare to make the error of slowing down due to my jaw aching beyond belief. On the few occasions when I was dumb enough to actually stop licking her for a moment during one of her orgasms, she got out her mean cock whip with metal braids. She then proceeded to beat my cock and balls until I thought they were going to be ripped from my body.

"I hope you don't mind the minor modifications I have made to Missy, but they were necessary to help improve her performance", Jessica said.

"Oh, no", Brenda replied, "I think they are marvelous improvements". She then took my balls in her hand and smiled as she looked me in the eyes. "Well, it certainly seems like these greedy balls are finally under control" she said with obvious glee. "Now when I loaned you to Jessica it was with the understanding that nothing would be done to you without your consent. Did you really agree to all these modifications, including these beautiful rings around your balls"?

I gave Jessica a nervous glance as I considered how to answer this question. I had never been told that I had any choice when it came to how Jessica treated me, she always made it quite obvious that I had no say whatsoever. I decided that I could explain this to Julie and Brenda once I was safely in their hands, but for the time being I wanted to avoid making Jessica angry. So I said that I had agreed to everything she had done to me.

At this point, Brenda gave me a quizzical look and started to laugh. "Jessica must really have you under her spell to agree to changes like this." she said as she started to squeeze my balls. "I would think that these rings would hurt so much that you would ask to have them removed. You mean to tell me that you still want these on?" she asked.

As she asked me this she began to really crush my poor balls in her hand. I looked over at Jessica again and I could tell by the stern look she gave me that I had better not complain or disagree at all. So I just moaned in pain and told Brenda that I still wanted my ball rings on.

"Well, I knew you were into pain, but I guess I just didn't know how much." Brenda said. "Does that mean that you don't want me to stop squeezing either?" she asked.

"Oh, no", said Jessica, "I think Missy appreciates the attention you are giving her. Missy, why don't you tell Brenda how thankful you are?"

I was trapped. I knew Jessica would make me hurt twice as much as Brenda was if I disagreed, so I tearfully thanked Brenda for her 'kind treatment' of me. One look at Jessica told me that this was not enough, so I then asked Brenda to please squeeze harder.

"If you insist", laughed Brenda as she proceeded to squash my balls so hard that I thought they would burst. I could hardly remain standing through the incredible pain and finally Brenda stopped. "My hand hurts too much to go on any longer" she said with regret. "Jessica, I have to admit that you have made great improvements in Missy's performance".
lurker

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Posts: 10
#21
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When will this continue?
gwalton

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Posts: 16
#22
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I had thought there was no more interest in this story. It occurred to me that it might be out of place here since this is not a typical cuckold story, but is more of a traditional story of female dominance.

However, since i have been asked, I will continue the story..
gwalton

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#23
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"I'm glad you agree", said Jessica, "and to demonstrate just how well her
performance has improved, Missy will now serve us dinner". Jessica of course
knew I would do my utmost to perform to perfection because if I didn't, I would
be subjected to her perfect wrath.

Before I started serving the dinner I had spent all day preparing, I put on my
serving tray. Jessica had designed this diabolical device for me after I had made
the unforgivable error of dropping the hand held tray I was using one day. It
made no difference that the drop occurred as I was being whipped on the balls
for moving too slow - no mistakes were allowed while serving dinner.

I could not drop my new serving tray because it was attached to me by four
chains, one to each corner of the tray. The two nearest me were connected to the
rings around my balls while the outer two were attached to my nipple rings.
Jessica also decided to improve my posture at the same time, so she had made the
chains attached to my nipple rings a little too long. The only way I could hold
the tray level was to arch backwards a bit, putting even more strain on my poor
nipples. To make things even worse, she had supplied me with a heavy silver
serving tray that weighed nearly ten pounds. The pain of holding the side of the
tray up by the rings around my balls was almost more than I could bear. My poor
***d ball sack was stretched horribly and my nuts were crushed mercilessly
by the weight.

Now that I was properly prepared, I proceeded to serve my three mistresses their
seven-course meal, followed by takes and cigarettes. I found it extremely
degrading and humiliating to be reduced to the role of sissy maid to three women
who I used to be equal or superior to. To make it even worse, this was happening
in the luxurious dining room where Brenda used to wait on me. Of course, Jessica
now sat at the head of the table where I used to sit. I was kept constantly on
the run and punished frequently and severely when I was more than a second or
two late refilling their glasses after each sip or emptying their ashtrays after
each tap of a cigarette. It was very hard to keep up with the three demanding
women, especially since I was required to perform a deep curtsey as I approached
each of them.

Punishment usually meant being whipped on my agonizing balls with Jessica's
penis whip. Just to make it more humiliating, I was told to hold my tray up
against my chest so my balls would be easily accessible for whipping. I also had
to politely thank my tormentor for correcting my behavior after each stroke of
the whip. If I forgot, I would get twice as many strokes. Brenda made a special
point of taking frequent sips of her take so she could get more chances to
punish me. By the time she was done with me, my balls felt like they were on
fire.
lurker

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Posts: 10
#24
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I don't know about the others but i liked this story very much!
dudette

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Posts: 53
#25
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Keep going! This story is amazing and I look forward to many more entries and even further degradations!
sissyanalinga

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#26
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Such a beautiful and erotic story! Thank You, please continue.
sissy analinga
trfetter

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Posts: 63
#27
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This story is so hot!!! please continue
gwalton

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Posts: 16
#28
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After the girls finished their dinner Jessica removed my tray and dildo gag and
told me to go get my bowl. While Julie and Brenda looked on with giggling
amazement, I knelt down on the floor as required and proceeded to eat the meager
leftovers out of my dog dish. I was forbidden to use my hands when eating
because my table manners hadn't measured up to Jessica's standards. That was
also why I wasn't allowed to eat at the table anymore either. Since this was the
only food I had been allowed all day I wolfed the food down like a dog too.

After the girls finished laughing at me, Jessica informed Julie and Brenda that
there was a problem. "I've had to reduce Missy's salary to just one dollar per
hour because I have to keep correcting her performance. And the nice gold
jewelry that has been pierced onto her has cost quite a bit. I'm afraid that
with the interest rate I have to charge, your debt to me is growing faster than
she is paying it off, even though I've doured her hours to 16 a day and added
weekends and holidays too."

Brenda and Julie then whispered among themselves for a few minutes and then told
Jessica that they had never been happy with my work either and proposed a deal.
If Jessica would be generous enough to forgive the $5,000 debt I was originally
loaned to her for, along with the interest and other costs, then she could keep
me as her maid on a permanent basis. Since I had been removed from their service
for six months, they had hired a real maid who was working out quite well, so
they really didn't need me around anymore.

Then they started to giggle as they commented that I seemed to behave much
better for Jessica anyway, so the arrangement would be best for everyone. Of
course I behaved better for her because her punishments became more cruel,
severe and bizarre every time she had to correct me again, but I knew better
than to point that out. They also observed that Jessica seemed to be a much
happier and more contented permister since she had taken me as her servant, so it
seemed appropriate that the situation should continue. It occurred to me that
anyone who went from having orgasms only once a month or so to half a dozen a
day ought to be pretty darn happy. Then it dawned on me that the situation for
myself had gone in exactly the reverse direction.
dudette

Member

Posts: 53
#29
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Keep going! This story is soooooo great!
gwalton

Member

Posts: 16
#30 
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As the conversation continued, I wanted to cry. Jessica was horribly strict with me and whipped me without mercy for the slightest fault. But I knew that any resistance would only make things worse for me. I was doomed to a lifetime of severe slavery to a goddess who treated me worse than a dog. I knew that Brenda could easily repay the $5,000 plus interest, but she didn't seem inclined to help me out of my predicament. She just looked me in the eyes and laughed at the fate which had befallen me. I saw that Julie was giggling at my plight also.

Even though I thought things couldn't possibly get worse, I should have known that Jessica could arrange to make it so. She mulled over the offer, and then giving me a triumphant smile said that she would accept it, but some changes would have to be made and I would have to first beg her to accept me as her permanent sissy maid. She promised me that if I didn't beg convincingly, she would make me regret it. I proceeded to beg and plead like my life depended on it, which it just might.

I couldn't believe that I was actually begging to be a willing slave to my
former wife's bitchy sister who relished nothing more than to see me suffer. How had I been reduced to such a state? I think Jessica could tell that I was having trouble adjusting to my new status, so she outlined some of the changes she had in mind to "help me adjust".

In order to help me adjust to my new role, I was to wear blinders and keep my eyes focused on the floor whenever I was in the presence of Julie. This was to help me forget my past; I would never see my lovely ex-wife's face again, just her feet. Jessica did say that if I provided perfect maid service when her sister came to visit, I might be rewarded and allowed to kiss Julie's ass, perhaps even eat her ass until she came. But I would never be allowed near her pussy again.

My relationship to Brenda was to change too. Of course she had already made it quite clear to everyone that I was not worthy of anything more than worshiping her ass. But Jessica decided that I must be blindfolded and bound during these sessions from now on. In addition, I was to be beat with Jessica's dreaded cane before the sessions as the price I would have to pay for the privilege of worshiping the woman who had changed my life for the better.
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