I had started to notice that the hormones & treatments as well as reducing and softening and my muscle tone and body, were also diminishing my stature slowly. At first I didn’t pay it too much attention, so much else was going on with my emotional state as well as my body. But then just after I had performed fellatio for the first few times I noticed just how much smaller and petite I now was. I was smaller now than Ms and so slender yet softly curved at the same time. Just like the other sissies the only thing that gave us a little height was our platform maids boots. And if anything although they increased your height they made you feel that much smaller and tottery as you hurried about your duties.
Ms dominance seemed so physical and powerful
now. Of course this was emotional too. But the Sirs were so very intimidating,
you felt so vulnerable as you curtsied in your very short dress, or if, and
often did, they felt you up and slapped your bottom with their huge hands as
you served them.
Ms said that it was only natural and very sweet. And also that it made me and the other sissies so
submissive and attentive when we served Her, especially intimately.
And now that at I had learned to please Her
with my tongue and the Sirs with my soft hot mouth. It was time for deeper sex.
I had gasped and looked up inadvertently, but aren’t we already having sex I
had asked innocently. She corrected my gaze downwards but softly, and me. No
She had laughed, penetrative sex, She told me. Naively I had thought She meant
releasing me albeit temporarily from my chastity. In any case not tonight I was
told, and dismissed to my chores. And not for the next few nights. I was so
very hot and horny, I felt like my cage must be bulging out under my apron. It
wasn’t incidentally, by design the cages limit you very effectively.
The patrons of the club and the girls seemed to
be in on Ms’s plan or at least it seemed so to me. As every thing they said to me was seemingly
heavily tinged with innuendo.
Then I was bent over the bench and locked into
my pink cuffs. There was a mirror facing me so I could see Ms behind me as I
squirmed anxiously still plugged on my dildo, until She removed it pulling it
out with a loud wet slurp. Then the pressure of Her pushing as She very slowly
but deliberately pushed inside me.
“Please Miss, please
“Oh do be quiet sissy.” She told me and stuffed
Her soaked panties into my mouth and continued to spread me with the cock.
I was sobbing & whimpering into the gag, when She laughed sweetly and told me She was halfway in
and pushed so deep. I almost felt like She would start to come into my throat from below, silly I know but She felt so big. Unlike the dildo, with each inward thrust I spasmed and tried to push backwards. Trying to grip and hold onto the well lubed shaft in vain. But my involuntary spasms and backwards grinding pressed and massaged Her with the smaller intimate end of the strap-on. With each thrust I whimpered and moaned and She moaned and sighed with pleasure and thrust deeper and deeper. The massive phallus also intensively massaged my prostrate which made me feel so very horny and also like I desperately needed to pee. I felt like hot jelly down there looking into the mirror seeing Her mounting arousal and pleasure. She took it slowly but very firmly, She wanted to fuck or peg me very deliberately. To totally dominate me with Her penetration and totally for Her pleasure. Then Her pace started to quicken and become more frantic and the passion on Her face so fierce as She thrust so hard and deep now, until moaning and gasping with pleasure She lay on my back still deeply inside me, and me still grinding and squelching on Her strapon as She lay panting in orgasmic bliss.
Pulling out eventually She immediately put my plug back in, sissies must be penetrated at all times. I was uncuffed and allowed to pull my panties up, then She sat back on, almost lying on the couch and I brought Her a fresh chilled wine. She was always thirsty after pegging or caning me. Sometimes I would also get a warm golden drink after a pegging.
Then She put my wrists back into the cuffs and
pulled me between Her thighs. Lowering Her skirt over my head as She liked to
do, so I could bring Her to a second slower orgasm with my tongue. After She had climaxed several times this
time. I licked Her clean and dried Her with a silk hand towel, I would hand
launder that along with Her panties later. Then I brought Her a fresh pair of
panties and another drink and I was dismissed to my other chores in the club.
My face was still wet and my panties sticky with lube, and I felt so tender physically and emotionally.
The other sissies recognized my ginger gait and curtsied sweetly to me. The patrons of the club saw my vulnerable tearful state too and recognized it for what it signified. They enjoyed patting or slapping my bottom as I hurried serving them.
Sissies feel especially vulnerable after a
pegging and naturally after their first time. The Men were quick to exploit
this and I was taken to the rooms for fellatio several times that evening. I
didn’t see Ms again that night as She must have left shortly afterwards without
bothering to say goodnight to me as She often did. Why would She after all ? I
was just a sissy maid.
The next time She pegged me, She just sent me away after I had cleaned Her. And the time after that She had me kneel between Her thighs again and let me kneel there kissing Her while we chatted for the rest of the evening and wanted cunnilingus several more times that night. It all depended on Her mood whether it was perfunctory or extended pleasure for Her. Much like a caning or cropping sometimes it was short and swift and at other times it was a prelude to Her pleasure. Always it was Her choice and for Her enjoyment. And always I curtsied and thanked Her after a pegging or cunnilingus and went away in tears feeling so desperate to love Her and so emotionally vulnerable.
This went on for a few weeks and with each passing day I felt even more emotional and dependent on
Her. So desperate just seeing Her for few moments at least each night. It was almost like my first few weeks on hormones and in chastity, but multiplied at least ten fold. In the office Miss was especially strict with me and I was often caned for the slightest and tiniest of things, or sent to the office to be caned by one of the office girls. They were allowed to cane me themselves but preferred the drama and ritual of sending me to Miss’s office. Where I would have to stand outside the door in full view of the office, though I would be facing the wall, till I was summoned inside. To be caned or spanked by Sir.
This was partially to keep me under firm
discipline in my state of constant emotional fluster. And also because it was
quite enjoyable to tease and punish the office sissy. In the club I was often
spanked by the Men and often taken to one of the rooms for fellatio, sometimes
by more than one Sir at a time. I like the other sissies kept my lips well
glossed and pouting prettily as we served. It was important to please and
titillate the Sirs unless we wanted to punished, my mouth felt constantly
sticky and thick with the intimate taste of Ms, or the Sirs cum.
Then one night it happened. I was told to go one of the rooms to serve drinks to a group of Men. The serving tray had 4 glasses and bottles of chilled beer. The rooms usually have a fridge and bar section anyway but it is considered good etiquette for the maid to bring the first drinks and wait outside the room until she is permitted to enter and curtsy holding the tray. Sometimes this is seen as a kindness to the sissy so she knows how many Men she might be serving and sometimes this is meant to make her feel more vulnerable and anxious. I knew that usually if I brought 4 drinks I would be spanked soundly & probably have to fellate all fours Sirs, while they laughed and chatted cumming in my mouth all over my face. I was already squelching and clenching on my plug anxiously as I waited outside the room. Other sissies hurried past me anxiously, there was always a strong atmosphere, almost a taste and smell, of sex and fear in these corridors.
I was called in but the room was in total
darkness. The tray was taken from me and my dress pulled up over my head so I
couldn’t see at all. I was cuffed and bent over the padded leather bench, all the
rooms have these benches for punishment or pleasure. There was also a thick
buckled strap to hold me down on the bench. Mistress liked to use the strap when She pegged me. I was to find out later that some of the men liked to utilize the strap, but mostly they liked to hold me down as I struggled, it made fucking me more enjoyable.
I was so very frightened. I couldn’t speak and in any case my panties were pulled down and stuffed into
my mouth.
“I think you have teased us enough with your
pretty little ass sissy.”
“Please Sir, please I am not fully pink pantied
yet Sir.” I wanted to sob and plead but all I could do was whimper muffled into
the gag.
“That tight little ass has been asking to be split ever since you arrived in
the club sissy.”
“As well as for a nice tawsing first.” I was told
I sobbed helplessly. The tawse is a thick wide
strap preferred by some of the men for punishing sissies and is very painful. I
had tasted it before and feared the leather nearly as much as Ms’s crop.
I couldn’t tell how many Men were present from their voices but I guessed at least 4. One of then stepped behind me with the tawse and gave me six stinging blunt blows with the straps across my buttocks then a different Man gave me another 6 across the backs of my upper legs. All the while the rest of the Sirs drank beer and laughed and joked lewdly.
My plug was roughly removed. There was a slurp
as the massive phallus was pulled out to applause from the Men. Then a very hard
slap across my bottom and big firm hands spreading my buttocks. With a loud cry
of pleasure He pushed inside me. My whimpers and moans of protest matched by
the laughter of the Men.
“Listen to those moans, see how much she wants it.”
“Such a hot little bimbo, teasing us with that
tight little bottom.”
“Well she isn’t teasing us now.”
More rude laughter.
Pressing my face down on the bench, He thrust deep inside me and began to fuck me quite urgently. His
living throbbing cock felt so much bigger and invasive inside me, even though the Ms’s favourite strapon was much bigger in both length and girth than He was. I imagined I could feel every vein of His thick cock, pulsing with His lust. Obviously I couldn’t but the thought of His huge bulbous glans and the thick veins on His throbbing shaft, filled my head as He raped me.
I could hear Him panting in exertion and pleasure as He relentlessly pumped my ass. Then suddenly feeling Him tense and stiffen behind me and deep inside me and then the wet thump of His orgasm. Erupting with pleasure inside me. He pushed my face down to the bench and pushed deep inside me pumping and spurting. Then finally He pulled out and splashed more of His hot cum all over my rear. I was now fully pink pantied. The bench underneath me was also slimy & sticky now. Almost immediately the second Sir slapped the backs of my legs and my bottom then thrust inside
me. All four of them eager to fuck me as quickly and urgently as possible. And all came quickly and powerfully. To me my ordeal seemed to last for hours but at the same time was so forceful and so unstoppable. When they had all finished my plug was pushed back inside my ass with another loud sticky slurp. One of the Men slapped my ass loudly as if to seal me shut, or signify His lusty approval and the others laughed.
I heard the door open and the voice of another
sissy. She was told to serve beers and then to kneel and lick each of them
clean. In the future I would have to kneel and clean the Men thanking them and
maybe fetching them refreshing drinks. In this first instance I was just left
face down on the bench, sobbing gagged with my panties still stuffed into my
mouth.
There was a rude laugh and cheer as one of the Men must
have spurted a last thick splash of cum into the sissies face as she licked Him
clean. I would later learn that this was quite common, as was a hot spurt of
precum, before Sir deep throated your mouth.
“You may swallow that sissy.”
“Yes Sir, thank you Sir.” Her voice was high
and anxious
“Be quiet and hurry up cleaning us sissy.”
“Yes Sir, thank you Sir.” We always had to say thank you even when we are told to be quiet.
Then as I heard the Men starting to leave. Sissy
was told to uncuff me and dismissively I was told to tidy & clean the room.
Sissy uncuffed me and hugged me, then curtsied
and left me to clean the room. I couldnt even look up into her concerned gaze. I
wanted to just sink in the corner and sob. The look on her face would have been
a mixture of concern and thinking I had gotten just what I deserved, and
jealousy too, sissies do crave any sort of attention from their superiors no
matter how demeaning.
As she left I was in tears totally overwhelmed.
Sobbing feeling totally used and discarded too, I sank to the floor for a few
moments crying.
But I knew what I had to do and get on with my chores. With my panties I quickly wiped up all the stray splashes of cum, then put the now even stickier satin briefs back on. And got on with hurriedly tidying and cleaning everything. Then I polished the leather bench and the leather couch
and sprayed scent around the room. 10 minutes later everything was perfect again, I straightened my apron and the bows behind me then left the room. I knew I had been a little slow because I was still reeling and upset and also a little physically sore and sticky. So I knew I would have to hurry back to serving in the club and not knowing who had first taken my sissy cherry.
However in the corridor I heard Ms call me from
one of the half opened doors. She was
sat smoking on the couch.
She could obviously see my state of upset and
distress
“Fetch me a fresh wine sissy.” She said coolly
“Yes Miss, thank You Miss.” I brought Her the drink and curtsied
“Tell me sissy why did it take so long tidying that room ?”
“Aren’t you supposed to serving in the club
with the other sissy maids ?”
“Miss…..” I really didn’t know what to say
“Well sissy ?”
“And why is your hair & uniform so disheveled
sissy?”
“Miss…I was taken into one of the rooms and
raped Miss, by four Men Miss, please…” I stammered
She chortled and looked at me incredulously as
if She couldn’t believe what She was hearing.
“Go and fetch my crop sissy.”
“Miss….Yes Miss, thank You
She put me in the cuffs and over the bench.
How could I have been raped?
When are sissies ever allowed to say no to a
superior, or disobey a superiors wishes?. Especially when a real Man wants to
enjoy a sissies mouth or ass.
And in any case She had arranged this with Her
friends, not only was it a special occasion for 2 of the Men. I was not told
what the special occasion was. But also it is another monthly anniversary of me
being in chastity.
Ms had thought it would be special for me to
feel a real Man cum.
And how dare I take so long tidying the room and it still not perfectly
clean for the next user? how disrespectful.
And why is the bow of my apron not perfectly
symmetrical behind me, and stray hairs
sticking out from the maids headpiece, cum stains on the back of my tights on
the upper thighs?
How disrespectful, and to the Men of the club especially.
Sissy must always be spotless, even if She is
still sticky in Her panties.
She stepper behind me and pulled down, peeled
down my panties. In the mirror I saw the look of exaggerated disgust at the congealing
sticky cum. Turning them inside out, sticky side out, She stuffed them into my
mouth and stepped behind me with crop now in Her hand.
I was given six stinging lashes with the crop and She sat down for a minute for a drink of Her wine then another six across my bottom and upper thighs.
I brought Her another wine after my punishment.
I could tell She was aroused but She wasn’t going to allow me the intimate
privilege of pleasing Her tonight. I was told to hurry back to the room and
finish tidying it. Then to return to the club. To celebrate my losing my sissy
cherry and now being fully pink pantied She had bought all the Men in the club
tonight. A beer and whatever expensive short they wanted.
I was not to be told who my first 4 ravishers
were, nor would I ever be told. Only the other sissy knew but She had been
given a drug that made her forget the details of tonight, so everything and everyones faces would just be a confusing blur
to her.
“You may go now sissy.” I was told
“Yes Miss, thank You Miss.” I curtsied frightened but not daring to show my tears, I smiled obediently.
“Oh and lots of lip gloss tonight & every
night sissy, let the Men see how eager you are to please them now you are pink
pantied sissy.”
“Yes Miss, thank You
Outside the door another sissy was already
waiting to enter and serve Ms.
The Men sitting in the club were very
dismissive and patronizing to me tonight. There was a few more than four now.
One of them sat me briefly on His lap, so I could thank Him.
“Thank you for what sissy, if I had taken your
cherry the pleasure would have been all mine wouldn’t it sissy.”
“Yes Sir, it would have been Sir, thank you Sir.”
“They are so pathetic and needy after you fuck them for the first time.” Someone said behind me. I realized that I was clutching and clinging at His arm weakly without thinking.
“Each and every time you fuck their tight
little asses, you mean.” Someone else replied.
He pushed me of His lap and slapped my bottom.
I squealed and pouted coquettishly but looking
down obediently.
“Go to the room sissy.” He told me.
“Yes Sir, thank you Sir.”
He only wanted to spank me and a BJ, and there
was lots of fellatio tonight but no more anal penetration tonight at least.
I now felt totally vulnerable and exposed in my
very short dress. As were all the other sissies as we hurried about serving.
Squelching in sexual fright on our plugs as we served and curtsied obediently. There was no going back from this point and no
getting used to it either. Sissies are kept in constant state of sexual funk
and fluster. So amusing and pretty to see, for our superiors at least.
The already extremely short dress felt impossibly that much shorter, like a constant invitation to the Sirs to enjoy my ass. Each slap and grope that much vulnerable. And in spite of my self I so wanted to please the Sirs so much, especially with my mouth, and to cling to the Sirs in tears after penetration. usually though after I had licked Sir clean and brought Him a fresh drink I was dismissed in tears with a slap on the bottom. This only made me want to serve & please them more perfectly, more desperately. I could barely meet the eyes of the sissies let alone the eyes of m superiors (when permitted, or instructed to look up) but I knew that all the other sissies felt like I did. All the other pink pantied sissies at least. There was a couple of new maids, who were still maids (in that sense). and in all fairness although I felt sorry for them, with their naïve tearfulness but also I was envious, they still had that special first time to come, even though i never found out who had first parted my legs, nor the second, third or fourth.
Ms had told me that this state was only natural. that the longer a sissy is kept in chastity and sexually enjoyed by her superiors. the more desperate she is to please them sexually and the more she tries to please them so totally perfectly. This was very satisfying for Her, as was fitting, and also very enjoyable for the Sirs. A sissy kept in chastity only becomes more obediently attentive and eager to please. To be kept in pretty dresses and serve beautifully and alluringly.
At the end of the night when I had hand cleaned
my uniform and was waiting for the taxi. The usual Man waiting with me, had
fondled and patted my bottom.
I had hoped Ms might come out and say
goodnight, but She rarely did normally and did not tonight.
“Those temptingly glossy lips of yours were
nice and busy tonight sissy.”
“Yes Sir, thank you Sir.”
“And your pretty little ass.”
“Yes Sir, thank you Sir.”
“Make sure they are glossy and slippery for me tomorrow sissy.”
“Yes Sir, thank you Sir.”
"And that ass nice and squelchy for me sissy."
“Yes Sir, thank you Sir.” I whispered already feeling Him inside me
“And
every night sissy.”
“Yes Sir, thank you Sir.”
He slapped my bottom as the taxi arrived.
“Goodnight Sir, thank you Sir.” I curtsied.
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