Sandy s Sissy Maid
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Mistress Sandy Gets A Sissy Maid free porn video
I had been serving Mistress Sandy for about 6 months. I felt I had
progressed well and felt Mistress had also. The fantasy of being a
sissy maid had been one held for over 20 years, but not until the
internet came along had I ever tried to actually find a Mistress or
Master. Masters came easiest, but I quickly found they all wanted a sex
slave, not a maid. However one of those Masters had a friend He felt I
should meet. From the start Mistress Sandy admitted She had no
knowledge of sissy maids. She did however have experience with
submissive men and She did have a desire for a maid. As I had never
done any real serving for a Domme we agreed to start slow and see how
things went.
Though I still insist it made no difference I will admit here and now
Mistress Sandy was a Black Woman. A large Black Woman with a good 75
pounds on me, an average mid fifty's white male. She was one year my
elder, one year and one day in fact. We got along well almost instantly
and race was never overtly mentioned in our play. Still it was there,
just as much as Her desire to be dominant and my desire to be a sub
sissy. Did it contribute to our individual mindset and sensual
stimulation? Maybe. Did it matter? No. Still I must admit it added
to the effect She had on me. And probably allowed each of our fantasies
be enhanced.
It turned out starting slow for Her meant cleaning Her home at least
once a week while She learned how to manipulate me into sissy
compliance. Not that I resisted. She was making a long held dream come
true. I got to go over to Her home, most often when Her Husband (Mr.
Robert, about 8 years Her junior) was gone, dress up like a sissy, serve
as a maid and be put in a state of erotic torment. She was a very
sensuous Woman who did not mind having a submissive sissy assist in Her
pleasure either. I was not used as a man, She had a man, my assistance
was always designed to enhance and satisfy Her dominate desires while at
the same time display how much of a sissy I was. She quickly began to
turn me into Her idea of a sissy rather than simply allow me play sissy.
It was a gradual progression to which I guess I should have paid more
attention. But that is hind sight.
Within the first few weeks I was required to keep my toenails painted at
all times. And within the first few months She had me dressing on my
own and reporting to Her home feminized and dressed as Her maid. I had
read the stories, I knew these were supposed to happen but it was
certainly not my idea to implement the requirements. I never mentioned
them to Her, and certainly those first few times dressed in my maid
uniform driving to Her home, did not want it to happen. We also
mutually agreed upon a chastity device, which I ordered and paid for but
had delivered to Her home. Again, something many sissy sights and
stories suggested. From the very first fitting in Her home I knew the
power it was going to give Her over me. And when She said I needed to
shave my pubic hair so I would look more like a sissy and make the
device easier to put on I accepted that as natural, again a normal
requirement for sissies. Maybe it should have clicked then that
Mistress was going down a check list for training me, but I wasn't
thinking with my head.
By about four months into or relationship She and I had become close.
Not only She and I but also Her Husband and even Her teenage Daughter.
The Husband knew the extent of things, the Daughter only knew that when
I was dressed as Wendy I served as a maid. The few times She saw me in
Their home She acted more amused than anything and was grateful at
having Her room cleaned and Her laundry done for Her. Truth is, I was
not the only odd person She was exposed to. The Family also often came
over to my home, where we interacted as friends. I was rarely dressed
as Wendy when they all came over, that first year at least. I have a
comfortable home with a few luxuries They did not have. Both Mistress
and Mr. Robert enjoyed my hot tub. Mr. Robert especially. Often
Mistress and Mr. Robert would come over, we would sit, drink wine, talk,
often with Mr. Robert going to the tub leaving Mistress and sissy to
interact as, well, Mistress and sissy. The back bed room in my home was
set aside for Mistress' use when She was there. She kept a few things
in the dresser such as paddles, whips a few restraints. And it was
where I was to keep the chastity device when not in use. I learned to
try and avoid the room anytime Mistress was over. If Mr. Robert were
present an elevated level of humiliation was added when I was taken into
the room.
Anyway, about the six month mark of my serving Mistress Sandy, She and
Mr. Robert came over one Monday night. There was a football game on and
we started watching as we talked. Mistress more interested in talking,
Mr. Robert more interested in the game. Mistress Sandy startled me when
She handed me a bag with a pack of woman's disposable razors, shave
cream and body lotion. She then told me it was time I shaved like a
sissy. This brought Mr. Roberts attention back to the conversation with
a rather evil snicker. I rose at that point and asked if They might
like some wine. Not waiting for the answer I came back in with some of
Mistress' favorite white wine and glasses. Mr. Robert went back to the
game as Mistress and I discussed my shaving. I had shaved my legs over
the years in fantasy play, even shaved my chest once. But since seeing
Mistress, only my genital area had been shaved. Which now had been a
requirement for several months. I mentioned the itch shaving my chest
had caused, Mistress instead if I kept it shaved it would not be a
problem. I mentioned it could be embarrassing to be shaved, She instead
it was winter, I did not have to be seen by anyone. Our discussion went
on for a while, we drank and soon it was more of a laughing session than
a training one. When They left Mistress was a bit tipsy and I was still
gratefully a hairy sissy.
The next day in a message over the internet Mistress chided me for
getting Her drunk in order to avoid having to shave. It was a mild
rebuke so I did not panic, I even found it a bit amusing. Later that
week on Thursday, Mistress messaged me in the early afternoon and asked
what I would be doing that night. I told Her I had no plans, then She
asked if Mr. Robert might come over and use the hot tub. She said He
was down slightly in His back and thought it might help. That sounded
fine to me, I could use a nice soak too and would not mind the company.
When the car pulled up around 7:30 I was a little surprised to see Them
both get out, but not shocked. I should have figured She would not
allow Him be alone with Her sissy. I opened the door and sensed
immediately Mistress was in a playful but not playing mood. She told me
to get the hot tub ready as Mr. Robert went into the extra bath to
change. He and I passed as He was headed out to the deck and I was
coming back inside. His grin was not a good sign.
Mistress Sandy was still in the living room. Normally She headed for
the den as it was more casual. I asked Her if She wanted some wine to
which She roughly replied "Maybe later, what I want is for you to
strip." My slight hesitation was met with "NOW!" I was a bit taken
aback, and a lot aroused. So I slowly started removing my clothes. I
knew better than just toss them down and took my time folding each item
then setting them in a neat pile. It did take an extra request from
Mistress for me to remove my male underwear, but I was soon standing in
my living room nude. She asked me where the bag with the razor was and
I told Her it was in my bath. Her response was "Good, then let's go."
It was clear what Her intentions were and in my aroused state felt maybe
it was time to shave my legs for Her. As I started off to the bed room
She stopped me, pointed to my clothes and said "Get your clothes sissy,
you can't leave them in here." So I picked them up and nervously walked
nude, carrying my clothes in front of Her.
When we got to the bed room I put the clothes on a chest and went into
the bathroom. The bag of things was on the counter there, and She told
me to get in the shower. I stood a little shaky as She turned on the
water. Luckily the shower head was aimed at the wall as it takes a
while for the hot water to reach the bathroom. Mistress handed me the
shave cream and told me to shave my body. I started my begging, asking
not to have to. She insisted. I again begged, saying it was a bad
idea. She insisted. I agreed to shave my legs for Her, sure that a
bargain had been reached. She told me I would shave everything. All I
could come up with at that time was to say "Please Mistress, please"
over and over. It took very little time before She reached in the
shower and grabbed my genitals. Her hand cupped underneath with Her
fingernails digging into my flesh. She pulled and forcibly led me
through the house to the back bed room. I was bent over the bed, She
got out a paddle and a whip, set them on the bed beside me, picked up
the paddle and proceeded to give me about ten very hard, very fast
swats. It was not an erotic spanking. I still was expecting to get out
of the total body shaving and again asked if I might be allowed to shave
only from the waist down. At that She picked up the whip and gave me
five fast hard swats with it. She made it clear I was going to do as
She said, one way or the other. The sting on my rear was real, and so
was the erection of my sissy clitty. Mistress had me where She wanted
me. On the way out of the back bed room She lead me to the deck, told
me to hold my hand over my silly clitty and had me stand for Mr. Robert
to see. She told Him to take a good look at "the before." Then turned
me around and let Him see the red marks on my ass. He asked if She
needed help suppressing any sissy revolt, to which Mistress said "No,
she has decided to be a good gurl." The whole episode keeping me in a
proper submissive attitude, to which Mr. Robert seemed a bit amused.
She led me back to the shower. Handed me the razor and shave cream, put
Her hand at the base of my neck and said, "Start right there." I knew
better than resist that time. I took the cream, smeared it over my
chest and began shaving. By the time I was at my nipples Mistress had
leaned against the counter and had Her hand under Her loose dress. She
proceeded to instruct me and manipulate Herself at the same time. I
shaved my chest, underarms, ass and legs all while listening to Her
pleasure Herself. When I stopped and started to turn the water off She
tapped my arms. I wanted so badly to get out of that, but after She
snapped "Do it!" I took a new razor and shaved my arms smooth. Once
that was done, She had me turn around and She proceeded to shave my back
for me. I was totally defeated and totally hairless.
She had me wash with body soap and rinse off, then clean the shower
floor. There as a huge wad of hair. She reached in and turned off the
water then motioned for me to step out. She picked up the lotion, put a
small bit in my hand and told me to smooth it on before drying. She
said that was the best way to do it. I rubbed the lotion into my smooth
wet body knowing I was doomed. I was so turned on I was weak at the
knees. She did my back teasing my buns while at it, had me pat myself
dry and then ran Her hands down my body inspecting it. I could tell Her
state was as edgy as mine, but She was not as displayed.
Once satisfied She led me aging to the back bed room. I almost cried
pleading I had been good. She agreed telling me I was not going to get
a spanking but that I needed to be "fixed." When I realized what She
meant I again began to beg. Big time. She asked me what the problem
was and all I could do was admit the truth. I knew from the way my body
felt I was going to want to play with my sissy clitty. Insisting I had
done as She asked and should not be punished. She told me it was not
punishment, that She knew I would play with my sissy clitty and that was
why it needed to be put away for now. Begging did no good, I was soon
locked in the pink cage. I looked and felt so helpless. I was nude,
smooth as a ten year old, had a pink chastity device locked on me and
shaking like a gurl in heat. Hell, I was a gurl in heat. She gently
grasp the cage and lead me to the den, Where Mr. Robert was now sitting
watching TV.
As we entered He looked up and smiled. OK, more than smiled. She had
me stand in front of Him and asked if He liked "before" or "after" best.
He sat back on the sofa, taking me in with His eyes and said, "Now that
is a sissy! I like it." He reached out, ran His hands over my skin and
even toyed with the chastity device calling it "cute." Mistress laughed
and told me to go put on some panties.
I returned in a pair of pink lace panties that covered all my front and
most of my rear. Mistress had me serve wine and even allowed me to have
a glass with Them. Typically when in such a positing I only waited on
Them. I did remain kneeling on the floor in front of Her rather than
sit in my chair though. Within about 30 minutes Mistress told Mr.
Robert She needed some relief and They should be going home. On the way
out I again begged Mistress to let me remove the device. All I got was
a "We will talk tomorrow."
The next day Mistress told me just how much She had enjoyed Herself,
both at my home and later in Hers. I told Her I was hoping to have some
enjoyment myself, adding a "Please Mistress." She had me turn on my
camera and show Her the plastic numbered lock had not been removed, then
asked me what I was doing on Monday. I told Her I had no plans and She
said if I agreed to dress for Her first thing Monday morning I could
take the cage off. I promised to be a "good gurl" and She gave me
permission to free my sissy clitty. As soon as the cage was off I got
off my computer and went to the bed room to play. I was in such a
state, my hairless smooth skin and painted toenails an ever reminder of
what and who I was. I knew Mistress Sandy had more plans for me. I
knew She was just getting started. I knew if I did not stand up and at
least try to be a man I was going to be trapped as Her sissy whenever,
wherever and however She wanted. Looking down at my body I also knew
the hair was not going to grow back for a while and until it did my self
image was not going to be very manly. It did not matter much though as
I was deep in a fantasy come true.
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