A Sissy her maid and the Mistresses
- 4 years ago
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The Sissy Diaries - My Two Mistresses free porn video
Dear Diary,
Things were going so good for me. I got promoted at work, even though I
know most people there don't like me because I'm quiet and reclusive.
It's just that I can't get too close to anyone there and risk exposing
that I'm a closeted crossdressing sissy. Still, I do my work and go home
to my apartment and escape into my sissy world. Still, I decided that
with my promotion and my increase in salary, I could afford a better
apartment in a better neighborhood and that's where my trouble began.
I started looking for a new apartment by checking the bulletin board in
the local grocery store of a neighborhood that I thought would be the
perfect location to move my sissy sanctuary. It's there that I met Alexa
and Kerri while browsing the bulletin board of apartment ads. Alexa was
a raven-haired goddess, and at 6' tall, she easily towered over my
petite 4'10" frame and was clearly the dominate one of the two. Kerri
was average height but was much more bubbly and they seemed friendly and
said they knew where I could find an apartment they were sure I'd like.
I was so taken with their beauty and friendliness that I dropped my
guard. Oh diary, what a mistake that was.
We were soon at their apartment building, and what a building it was. I
was instantly impressed and overwhelmed by the building, and immediately
said that I could never afford anything in such a beautiful building.
But they tried to calm my concerns and said that I would be surprised
that there were apartments that they were sure I could afford. We
continued to their apartment, and I was again stunned. It was the
penthouse suite in this very luxury building and I was even further
amazed. They were the building's owners and managers. I was now even
more skeptical of the affordability of such a wonderful place but they
convinced me to look at their apartment brochures. While we sat in their
spacious living room looking at available apartments, they offered me a
drink to help me relax. The next thing I know, I'm feeling really weird
and kind of giddy, and that's when they pounced on me. Soon, they had my
hands in pink leather restraints and locked together behind me. Then a
matching set were wrapped on my ankles and similarly locked together. As
I tried to weakly call for help, a pink leather ball gag was stuffed
into my mouth. Oh diary, I was so extremely terrified being bound and
gagged, especially when they started to remove my clothes.
When they removed my shirt, Alexa immediately noted my hairless chest
and underarms and started to comment to Kerri that she was right. Kerri
said not to get too ahead of herself, that she could still win the bet.
I had no idea what they were talking about but I was even more terrified
by my situation but the drug in my drink made me very weak and docile.
So I just laid there in silent humiliation at what I knew was about to
happen. Alexa then reached down and locked a pink leather collar around
my neck with a large ring hanging from the center and then removed my
jeans. She immediately started laughing and congratulating herself on
how right she was. I just laid there in embarrassment at my secret being
exposed, for I was wearing my favorite "good-luck" pair of satin
panties, pink with white lace which were very girlish and pretty with my
sissy name Prissy-Sissy embroidered on the side. Kerri, seeing my
embroidered name ran her hands over it and wondered out loud how she
could've thought I was anything but a sissy. Showing her disappointment
with losing some bet, she pulled my panties down to reveal my tiny
hairless sissy clit, as she called it, to go with my hairless legs and
said I was just what they were looking for.
Kerri then left the room to get something that she said would look just
perfect on me. Meanwhile Alexa began removing my clothes but since I was
in these pink leather restraints she began cutting them off with a large
scissors. Seeing this made me even more scared and I began weeping at my
situation. Soon I was naked except for the pink restraints and my pink
panties around my thighs and Alexa standing over me with a very
triumphant looking grin on her face. Kerri returned with some sort of
small clothing item, some pink metallic objects and what looked like a
pink leather belt. She wrapped the strange belt around my waist but it
had buckles on the sides, which she adjusted until the belt was very
snug. She then locked the clasps on the buckles with tiny pink heart-
shaped padlocks. Then to my growing horror, she forced my sissy clit
into a pink metal ring that was attached to two straps, one that hung
from the front center of the belt. Once the ring was positioned around
the base of my sissy clit, she then took the other strap which hung on
the ring on the opposite side and connected to another buckle that sat
on a wide leather piece that hung from a strap on the back of the belt
and was positioned right over my anus. The front strap also had a buckle
which she tightened to take up any slack and promptly locked it with
another pink heart-shaped padlock. Then, to complete my sissy bondage,
she proceeded to place a pink metal chastity cage over my tiny sissy
clit, which in my terrified state had shrunk to it's littlest size. The
cage attached to the ring on the harness which she then locked with
another pink heart-shaped padlock. Once done, she said that every little
sissy like me should always be locked into a pink chastity cage and butt
plug harness. With that, she then place a pink satin and white lace
chastity cover over my chastised clit which matched my panties perfectly
to add to my humiliation, and then pulled up my panties.
Oh dear diary, as I laid there in terror and humiliation, Alexa and
Kerri looked down at me and then Alexa said it was time for the next
phase. They each picked me up by one of my bound arms and dragged me to
the bathroom and set me on the toilet. Alexa said that since she won the
bet, Kerri was to prepare me for training. I didn't like the sound of
that dear diary, but I couldn't do anything about it. Kerri unbuckled
the strap with the empty butt plug holder and uncovered my anus. She
then put surgical gloves on and began lubricating my anus with her
fingers. I was stunned by this intrusion and began pleading with her not
to do this but all that I said was garbled by the ball gag. Once she
felt I was sufficiently lubed up, she then brought a metal hose from the
shower with a metallic butt plug attachment and worked it into my anus.
I started to plead even more but she looked at me with a very serious
face and said if I didn't really want to be punished severely, I would
stop all this nonsense and sit still or she and Mistress Alexa would
really give me something to complain about. After that I just
surrendered to her and her plans for me. She proceeded to give me
several enemas to clean me out as she put it. She always filled me till
I cramped but the butt plug prevented me from expelling the solution
till she opened the release on the plug. Some solutions were soapy and
floral scented and some were just water. Once she felt I was perfectly
clean, she then filled me with a very flowery scented oil to finally
prepare me for training. Once I expelled that, she pronounced me ready
for training, unlocked the restraints to my ankles and lifted me up and
walked me out of the bathroom. I just let her lead me to wherever I was
going for training.
She lead me to what she called the training room, but oh diary, it
looked like a torture chamber for sissies. There were all sorts of pink
handled paddles, whips, and other scarey looking pink devices on the
wall, but the most terrifying object was a pink bench in the center with
a neck brace and waist bar. I just let her lock my collar into the pink
padded neck brace at the front of the bench which also acted like a sort
of posture collar which forced my head to look straight ahead. After
that she positioned my waist over the waist bar and wrapped another pink
leather belt over my back. She then locked my ankles to rings at the
back of the bench and completed my training bondage by unlocking my
wrists which were still connected to each other behind my back and then
locked them to rings near the neck brace. Oh diary, here I was locked
into a training bench on all fours and feeling very vulnerable and
foolish for getting into such a situation, but unable to do anything but
hope my two beautiful captors would let me go. The bench was on a
pedestal so my face was level at Kerri's waist as she said not to go
away, that she and Alexa would be right back to start my training and
left me for a few minutes.
I didn't have long to wait as Alexa immediately appeared dressed in a
long black silk robe. She knelt down in front of my face and started
stroking my face to try and soothe my fears and wipe away my tears. She
said how fortuitous it was that I was looking for a new apartment
because they were looking for the perfect sissy roommate, and that I
certainly looked like the perfect candidate. But she said that it'll all
depend on how I behaved in the next few minutes. Either I can do as I'm
told like a good little sissy or they'd punish me. If I still refused to
cooperate, they'd drop me off at work in only my panties, chastity,
still bound and gagged and expose me to all my coworkers. When she saw
the total look of terror in my eyes at that statement, she knew I would
do anything to avoid that, so she said she hoped it didn't come to that.
Kerri then walked into the room dressed in a red silk robe and then
Alexa said that we could now begin. Kerri closed the door to the
training room and that's when I noticed that the room was padded and
thus sound proof.
The first thing they each did was grab a pink leather paddle hanging
from one of the walls. As they stood in front of me Alexa said that I
was to refer to them as Mistress Alexa and Mistress Kerri respectively,
or I would be spanked. They asked if I understood but all I could do was
grunt a yes Mistress Alexa into my pink gag. She then said that as long
as I behaved, they could do away with the gag, especially since the room
was sound proofed, confirming my suspicions. Once she pulled the gag
from my mouth, she stood back and they both parted the tops of their
robes to reveal beautiful breasts supported by half-cup brassieres,
Alexa's in black satin and lace, and Kerri's in red to match their
robes. Alexa said that she thought a sissy like me would love to play
with these beautiful breasts but that it would depend on how good of a
sissy I was. I began to think things might not be so bad as their sissy.
Oh diary, how wrong I was. They then opened their robes further to
reveal matching satin and lace waist cinching corsets pulling in and
accentuating their slim waists and garter straps, which held up matching
laced topped black silk stockings enhancing their sleek sexy legs. The
garter straps also perfectly framed their COCKS ! Oh no, no, no. Oh dear
diary, they had cocks ! Large erect cocks. They weren't real girls !
They were t-girls and I had been trapped by them. Kerri proceeded to
walk behind me and pull my panties down to my bent knees while Alexa
walked towards me and began outlining my lips with her cock while Kerri
rubbed the face of the paddle over my naked butt. Mistress Alexa then
asked if I knew what a good sissy does. Knowing what the response was, I
proceeded to tell her that a good sissy sucks cock Mistress Alexa, but
the humiliation at my position didn't prevent me from weeping and
stuttering as I answered. She then asked if I was a good sissy and I
knew all I could do was answer yes Mistress Alexa. With Mistress Kerri
still rubbing my butt with her paddle, and the padded neck brace
preventing me from moving my head at all, I did the only thing a good
sissy could do. Oh dear diary, I parted my lips and accepted Mistress
Alexa's cock into my mouth, becoming a sissy cocksucker.
As Mistress Alexa's cock slid back and forth across my lips and tongue
and in and out of my mouth, she said that I needed to suck harder if I
was a good sissy, to which Mistress Kerri gave me a slight tap on my
butt with her paddle, nothing painful, but certainly attention getting.
As tears again began streaming down my face, I obediently complied and
sucked her cock as hard as my little mouth could, my lips wrapped around
such a big cock in a perfect "O" like a good sissy cocksucker. Mistress
Alexa was obviously quite pleased with my performance and began moaning
her appreciation and remarking that I was an excellent sissy, the
perfect little sissy that they were looking for as a roommate. As I was
dutifully sucking Mistress Alexa, I heard Mistress Kerri retrieving
things off one of the walls but couldn't see her, my head forced by the
neck brace and Mistress Alexa's cock to look up adoringly at her. But I
soon found out what Mistress Kerri was up to, as she first moved the
unbuckled strap to the empty butt plug holder out of the way and then
again began lubricating my anus, my sissy pussy or sussy as she called
it with some sort of large syringe, injecting lube into my sussy and
rubbing it around the entrance. She then began sliding increasing larger
size butt plugs in and out, moving to a large size when she felt my
sussy could handle the current one. Each time she did this, I moaned in
pain but could say nothing with Mistress Alexa's cock in my mouth.
Eventually she reached the largest size plug and then positioned herself
behind me and slowly worked her cock into my sussy. By then I was all
out of tears and just moaned in pain into Mistress Alexa's cock, which
she apparently appreciated, remarking that I was indeed the perfect
sissy for them. Soon they were each working their cocks into me at each
end with a steady pace, with Mistress Kerri smacking me lightly on my
butt with her paddle and encouraging me to grip her cock with my sussy
muscles like a good sissy. Eventually, I was able to comply somewhat
with her request, even though I had been a virgin sissy, and she stopped
spanking me and just enjoyed fucking my sussy.
Oh diary, I lost track of time as they fucked me, my mind spinning in a
confused and humiliating spiral of emotions as I dutifully sucked the
cock in my mouth while the one in my sussy began to actually feel quite
pleasurable. Soon I was gripping Mistress Kerri's cock much tighter as I
began having my first sissy orgasm. Oh diary, as if my embarrassment and
humiliation couldn't get any worse, I actually enjoyed being fucked like
a sissy bitch. But it was only a release, I was still horny and aching
for a real orgasm but the sissy chastity cage prevented that. Still
Mistress Kerri remarked that I was indeed that perfect little sissy they
were looking for and eventually orgasmed as well filling my sussy with
her cum. Mistress Alexa wasn't far behind and soon orgasmed into my
mouth, shooting some directly down my throat, but mostly filling my
mouth, to which she commandingly said I was to swallow every drop like a
good sissy if I knew what was good for me. Of course dear diary what
else was I going to do, so I obediently swallowed the cum in my mouth.
With both of them spent, they withdrew from my mouth and sussy, with
Mistress Kerri locking the butt plug holder strap back into place, but
this time holding what felt like the largest butt plug they had. They
then both knelt in front of my face with the biggest smiles on their
faces and were positively overjoyed with my submissiveness and
obedience. They said that I was going to make a lovely sissy roommate
and each kissed me on the cheek and said not to go anywhere, as if I
could, as they had some things to do. With that, they left the room but
not before wheeling a video monitor in front of my face. While they were
gone a video loop of my sexual humiliation and debasement played before
my very eyes and ears. Everything I said and did had been recorded
giving proof that not only was I a willing participant, but the video
proof of my sissy orgasm was also included, that I was a natural sissy
slut, and that they had brought it out of me in just a little over an
hour or so. The conclusion was obvious to me. I was theirs to do with as
they pleased or the video evidence would be available to destroy me
entirely. As if that wasn't humiliating enough, the butt plug that
Mistress Kerri had locked into me vibrated for a couple minutes at
regular intervals as I watched the video loops. It also seemed to grow
in length and girth, stimulating me just as if I was being fucked by
Mistress Kerri's cock. Soon I was moaning and voicing my appreciation at
the sensations running through my body until I had several more sissy
orgasms. This made me even more horny and I was dying for a real
release.
When both mistresses returned, they stopped the computer program which
was remotely activating the butt plug in me. They said it was a lovely
little gadget that they said would certainly keep me in sissy
submission, but also keep me as an enthusiastic little cock sucking
slut. They could also control it with a hand-held unit and demonstrated
it, which instantly had me moaning like a sissy slut. I begged them to
please release me from my chastity cage but they said I'd have to earn
such a privilege, but they'd discuss such things later. Then they showed
me what they had been doing while I was gone and I knew I was never
leaving this place without their permission. They began to hold up items
from my sissy wardrobe. They had my drivers license so they had gone to
my apartment to retrieve all my sissy clothing and accessories. A few of
my outfits were of particular interest to them and they expressed great
interest in these. These outfits were my sissy maid uniforms. They had a
very demure satin bodice on top with a peter pan collar and short puff-
ball sleeves but with a very short skirt made even shorter with a full
petticoat and that also had an attached apron which tied into a very big
sissy bow in back. When I wore these uniforms, not only the tops of my
lace covered stockings and garters were visible but also the ruffled
lace on my sissy panties. Mistress Alexa remarked that she could
understand why I went by the name Prissy-Sissy now as seeing these sissy
maid uniforms certainly would make me feel like a very Prissy-Sissy, and
asked if that was true. I could only reply that it was true Mistress
Alexa. Her face lighted up even more than it had already and said that
she and Mistress Kerri were looking for a sissy maid and that they were
sure I'd love to be their sissy maid wouldn't I. Of course I readily
agreed, that I'd love to be their sissy maid but wondered if I'd still
be keeping my boy job. They laughed at that and wondered why I'd want to
keep such a boring boy job when I could be their sissy maid 24/7. To
that I just said that that was just a foolish sissy thought, and that
I'd love to be their sissy maid forever. They both were quite pleased
with my response as if I could've responded any other way. Mistress
Alexa then remarked that the name on my license wasn't Prissy-Sissy but
that would soon change to which I just obediently agreed and thanked
her. They then reviewed the footage of my solitary training at the hands
of the remote butt plug and were very impressed with my enthusiasm with
being fucked like a sissy slut. They also noticed all the cum that I had
released onto the bench and said that I truely am the sissy slut they'd
been looking for.
After that, Mistress Kerri released me from the training bench, removed
all my restraints and took me to the bathroom to clean me up. I was so
exhausted I just followed her like the defeated sissy I was. The shower
felt good on my already hairless body and the scented body soap smelt
wonderful. Mistress Kerri was then standing outside the shower with a
big plush towel to dry me off and when I stepped into it, she pulled me
close and looked right into my eyes. She was very happy that I had
agreed to be their sissy maid, as Mistress Alexa can be very dominating,
and now that I was their new submissive sissy maid, that she wouldn't be
on the receiving end of all of Mistress Alexa's perverse desires and
pleasures. All I could do was say yes Mistress Kerri and thank her, to
which she gave me a very warm intense kiss. I melted in her arms and was
glad to be out of the chastity cage, but that was short lived. She soon
had me locked back into my chastity cage and the butt plug harness with
the large remote controlled butt plug. She then led me to what would
become my room, a room fitting for a sissy maid. It had a pink and white
vanity, a matching little bed, and a wardrobe for all my sissy maid
uniforms which were laying on top of my new bed along with my other
sissy dresses, lingerie and accessories. She then sat me at my vanity
and over the next hour or so we worked on my make up. She was very
impressed with my make-up skills, having me do up a very slutty look,
with long false eyelashes, heavy mascara, eyeliner and deep plum shadow.
She had me do my lips with a matching deep plum lipstick and an even
darker lip liner, which made my lips look very plump and full. Some
rouge and face powder completed the very trampy look that she wanted.
She then had me dressed in my black satin and white sissy maids uniform,
with matching waist cinching corset and lingerie. She even had a
matching chastity cage cover which she had me put on. That's when I
began to wonder if this was fate all along. To complete my sissy maid
look, she had me tie my long light brown hair into two pig-tails high on
the top of my head with large black satin bows and little white lace
flowers with my bangs hanging down in front to my thin feminene eye-
brows. I then attached my maids cap over the top of my head in front of
my pig-tails. As I stared at my reflection in the vanity, the reflection
of a dainty girly sissy maid stared back and I knew that I was to be
such a sissy maid to my two mistresses for as long as they wanted. I put
on my black satin high-heeled sandals and was led to Mistress Alexa for
her approval and the start of my life as a submissive sissy maid and
sissy slut to my two mistresses.
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