Mid afternoon Mistress had come home from work with one of Her friends, well actually from shopping and drinks after finishing work at lunchtime. Her senior position meant She could choose Her own office hours. The pair had arrived by the chauffeured taxi service and the driver was smirking at me as I opened the door and curtsied to the Ladies. Already knowing about sissies and sissy maids were, Mistresses friend had actually patted His bottom and told Him to stop staring.
The chauffeur taxi service was just that, an exclusive taxi service for the wealthy and in this case the wealthy Mistresses, Sirs and Masters on the scene. Most of the male staff were vanilla as were some but not all of the female staff. They wore very formal uniforms although the female drivers wore leather miniskirts and very sexy figure hugging jackets. The male drivers were well built and their uniforms well cut to show off their physique too. These drivers were also used transporting sissies around, usually in the back of a van or SUV
minibus, with darkened windows so the sissies could see out. But Mistress also enjoyed the eye candy. On more than one occasion She had brought a driver for sex, male or female. And on occasion for a BJ from me. Today though it just the ordinary chauffeur service, though they were also very aware of their more decadent indulgent wealthy clients and their chastity sissy maids.
Most people no matter how vanilla would have attended stags, hens, events & parties where a sissy had been booked to perform intimate services, after they had watched a very highly paid female stripper or lap dancer, who did not perform such personally demeaning services with strangers, for fees or otherwise, but rented a sissy for just such a purpose, for Her shows as an extra entertainment for the patrons or Her guests and increase Her earnings. Many seasoned Mistresses were pleased to send their sissies out to earn tips, to partiers or with sissy Masters/pimps even if they themselves didn’t have any financial need. Serving real Men made sissy much more delightfully pliable and submissive than usual for Her and the cunnilingus was delightful.
Inside the door I had taken their shopping and jackets and curtsying again, twice, once on each leading knee, in greeting I also kissed their bottoms. Miss (the visitor) on each cheek softly and respectfully. Most of the Ladies like to lean back and wiggle slightly teasing me when I kiss their bottom. And Mistress on each cheek and then between the cheeks very intimately. If we are alone often I am allowed to kiss Mistresses pubic mound through Her skirt but not today. Both Ladies smiled as I stood up again and smoothed down my apron, my fingers hesitating every so slightly over my tiny chastity bulge.
And then watching me again after I had served them drinks in the lounge.
“I do hope you didn’t get too excited in your little chastity kissing my bottom sissy.” Miss said smiling.
“Yes Miss, no Miss I didn’t Miss, thank You Miss.” I curtsied feeling very excited now.
“Yes you don’t want to be fetching the canes again later, do you sissy.” Mistress said icily but amused
too.
“Yes Mistress, no Mistress, please Mistress I don’t Mistress, thank you Mistress.” I almost whimpered, blanching with fright at the mention of the canes.
“They are so sweet & pathetic when they squirm so.” Miss laughed
“Of course I preferred the chastity tubes with spikes for my sissy in the beginning.” She laughed and paused thoughtfully “It didn’t really stop him trying to get erect but it was very enjoyable to watch him try.”
Miss’s husband had cheated on Her & when She found out She had put him in chastity and cuckolded him with a very dominant alpha male. Then She had found She enjoyed having him so tamed and subservient She decided rather than take all his money and assets then divorce him. She decided instead to take all he owned & then feminize and sissify him. The wedding contact was legally converted into a sissy contract which was totally binding when it came to Her control of him & everything ‘s/he’ had once owned. Not
only that but She did it in front of all of his and their friends, his work colleagues, and even the lovers he had cheated on Her with. She even then made a play on cheating on, or cuckolding him with His male colleagues & friends but that was actually just a pretense, not that he knew that. And it was not that any of them talked to him again after they found out he now lower case she had been sissified.
I knew this because Mistress and Miss often chatted about this in front of me. Either not caring what the maid heard or more likely to titillate and tease me. Mistress titillated Herself would often send me for the little patent leather heart shaped cushion after Her guests had left. Not so much to protect my knees as I squirmed so intimately, but rather to protect my stockings, my uniform had to be immaculate at all times.
Miss had actually enjoyed being dominated by the bull, as terminology in that cuckolding/hotwife scene
goes. At first Her sissy was just left at home while Miss went out with Her lover. Cut soon sissy was the attendant maid, while Miss cuckolding Him in their bedroom. Her sissy wasn’t actively participating the sex at the time, but She was expected top serve drinks and change sex soiled sheets. Or sometimes if the bull needed to leave after sex sissy would sleep in the very large wet patch besides Miss who wasn’t. Afterwards sissy would clean her Mistress, Miss with Her tongue. And later as the relationship developed sissy would also lick the well endowed bull clean too.
Sissy was always very aroused by this. It is quite interesting that often couples who had no prior interest in cuckolding find it very satisfying if they accidentally or deliberately find themselves experimenting. Satisfying for Her at least and increasingly very satisfying for Her, not allowing or delaying any satisfaction for sissy. Eventually curtailing it completely for him.
“Oh I did allow Him a little squirt, and it was a tiny squirt occasionally.” She had told Mistress.
“At first maybe once per week, then once a month and then every few months.” She had continued with complete disinterest. “Oh do look at your sissy blushing.” She laughed
Mistress had looked on with an air of disdain & indifference.
“More wine sissy.” She told me sharply, just to watch me blanche at Her tone. Both of the Ladies glasses were more than half full.
“Yes Mistress, thank you Mistress.” I curtsied, feeling that horrible very warm but also cold sensation of total fright between my upper thighs.
“Of course you have never allowed your sissy a little squirt have you.” Miss said.
“No of course not, she is much better without.” Mistress replied
“Or at least you are.” Miss said “And I do quite agree, nowadays.”
Mistress had insisted, even before we first met in person, online that I stop masturbating until Her device arrived. I didn’t have long to wait. The next day a courier arrived with my package. It was one of the chauffeurs performing special carrier duties. She was wearing a leather mini skirt as part of Her uniform and was so utterly sexy, I had wanted to masturbate as soon as She left before putting the small chastity cage on. But She had stayed and supervised me as I locked the device taking the key with Her. She had made a point of trying to decide where to put the key before opening a small leather purse containing lots of other keys and dropping it in there, as if it was completely unimportant, which to Her and Mistress I suppose it was. Much how Mistress often makes appoint of displaying the ever present tiny key nestling in Her cleavage, or dangling from an ankle chain, or a on waist circlet, if She is wearing an outfit that shows Her exquisite midriff. The d
river had patted my bottom almost comfortingly but definitely patronizingly after that. I was lucky, often this carrier service is a woman and a male chauffeur just to add extra sexual humiliation for the sissy. And sissy once locked might get a firm slap on the bottom from Him. I’m told, or teased rather, that in these cases the Man often will wear quite tight trousers showing His very evident bulge. And on at least one occasion the drivers have decided to have sex while sissy attends them in sissies own apartment, before leaving with the keys, but I think this might be somewhat sensationalized retelling.
The driver had also given me a catalogue and list of shops from where I was to buy a selection of panties from, at Mistresses instruction. Even the pictures in the brochure made me swell in the locked chastity cage, as was Her lovely perfume, as She leaned in, not at all caring or minding my personal space, knowing I was just a sissy. The panties and the chemise style slips I was to purchase were glossy cream satin because I was still a virgin, to Mistress She had commented rather gaily.
And at first I had very much hoped & foolishly expected this situation to change shortly. It did of course
but not at all in the way I so longingly anticipated. To be allowed a release every so often as a reward, especially as my feminization regime improved. And then later when I entered domestic service as Mistresses maid and sissywife, I had hoped and longed fruitlessly in vain for the occasional squirt. But Mistress had never allowed this. Moreover after around 3 months or so, of teasing and half promises, I was milked & shamed in front of Her friends. But this only made me immensely more desperate to cum or squirt. But even that very limited empty disappointing release if you can call the total empty feeling of a successful milking that, this too was for the last time.
Mistress had often told me that She would envision a future utopia or femtopia, where sissies would never have been allowed to masturbate or cum nor ever even be allowed a full however tiny erection. Chastity & flaccidity strictly and legally enforced.
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But femtopia aside, it was as Her friends laughed and speculated around this ideal for them at least. Very enjoyable to have sissy long for what they once enjoyed so inappropriately, when they should have been dutifully busy with effeminate housework and chores. Even if it was a tiny pathetic squirt or splash. And it seemed that the tinier and weaker the splash the more desperately sissy longed for their return.
Even when as most sissies are, she was gelded or snipped, She still ached and hoped to be permitted to masturbate, just one more time, constantly. The tiny inadvertent often nocturnal leak or splash in her panties was a humiliating reminder of that.
In fact that was one of the reasons the physical snip has fallen out of favour. Not to be confused with circumcision or frenectomy (to improve oral agility and intimate service for Mistress) incidentally as all generally sissies have these both these procedures as standard. However after a physical gelding a sissy often loses her libido and just becomes unsatisfying, for Mistress, and very docile. So nearly all
these procedures have been reversed and reverted to the chemical process where no such docility or loss of libido occurs. In fact the libido is dramatically increased in chemically snipped sissies, seemingly in inversion to them being able to ever satisfy their denied needs.
The physical procedure can always be revered as it is part of the sissy legislation, that any physical change must be at least theoretically reversible even if the dominant party rarely, never, permits it. There is no stipulation that can this be compelled, incidentally, just that it is a possibility. Similarly it is perfectly legal to cane or whip a sissy, as punishment or just if it pleases the dominant, but no permanent physical damage or change is allowed. In fact on this scene drawing blood is seen as vulgar or distasteful and any wealing or welts are usually subcutaneous. Although it is quite pleasing to see sissy wincing ever so delicately and still perfectly, fearfully graceful as She minces prettily. With Her bottom and upper thighs puffy and pink smarting and stinging from a canning spanking or cropping. The only permitted legal physical change and commonly used is a very discrete ownership brand or tattoo
on sissies rump or upper thigh. It is discrete but if sissy has been marked as Her owners property very evident to anyone who knows or suspects what it is.
Miss had also eventually disallowed Her sissy, her releases, substituting them instead for milkings. Which left Her sissy feeling vacant and vaguely numbly unsatisfied, but still very horny and desperately attentive, as if somehow she might still be somehow granted a reprieve or release. At this point Miss had insisted that sissy perform fellatio on Her boyfriends and sissy could only earn a release by satisfying the bull and swallowing the bulls often considerable wad. Then when Miss had insisted that sissy also bend over for Her bull, She had completely curtailed the milking too. After all sissy was no longer by any description a male and did not deserve to cum, squirt or be milked. It was all just too messy, inconvenient for Her and now inappropriate.
It was also around this time this Miss had stopped being totally submissive to Her bull and insisted that if He wanted oral or anal He should call sissy.
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“It was just too submissive and degrading I began to find, even though the sex was still enjoyable.” She told Mistress.
“And after all sissies do love submitting to a real Man sexually.”
“Or at least we enjoy watching them perform & do so.”
Mistress & the other dominant Ladies and Hotwives who kept a sissymaid or chastitymaid insisted that when sissy was pleasing a real Man at least orally, sissy should look up obediently and submissively. Smiling and showing loving devotion to pleasing Him and being flattered & gratitude for being allowed to suck Him. And awe at his size and the thick load as if sissy had never seen such a big erection, such swollen balls or a thick load of cum. Even if sissy hated it as we did, or at least we tried to keep telling ourselves, even as we felt our tiny clitties swelling in our chastity at the thought of His huge throbbing erection.
Of course it was ok to struggle feebly with distress when Sir or Master bent you over and spread your bottom before splitting you with His very evident manhood. Moaning and whimpering in humiliated misery as He forcibly penetrated you. It wasn’t rape of course because Mistress allowed it. Because He so enjoyed sexually dominating you, as you whimpered into the panties stuffed into your mouth to quieten your pretty little protestations. Much as Mistress also relished pegging you in a similar fashion.
Shortly after that Miss had also stopped enjoying being dominated by Her bulls. Her increasing domination over Her sissy had completely changed the dynamic for Her. On the scene there were still dominated Ladies who enjoyed being occasionally dominated by their lovers. And lesbian situations where one lady dominated the other always or occasionally and sometimes switching. But in all cases sissy was always at the bottom and in strict enforced chastity.
In fact some Men who start out as bulls or lovers can also be gradually cajoled or otherwise tricked or enticed into being feminized. Some dominant women really enjoy this as
well as seducing cheating boyfriends and husbands and making them into good obedient sissies. The hormones, treatments and auto suggestion techniques work just as well on them too if they are found to unsatisfactory in other ways. In this scene for the main the emphasis is on Her pleasure, His is secondary, and for the chastitymaid, sissy simply does a she is told.
This had been the case with Miss’s first lover although it hadn’t been Miss who initiated and finished the process. Miss had however been invited to a very special pegging party though where all the former very hunky bulls former partners enjoyed taking turns pegging the now very petite submissive sissy.
“You still ache for a little splash, don’t you sissy, especially when you are kissing my bottom.” Mistress teased
“Yes Mistress, thank You Mistress.” I curtsied
“And mine too I think sissy.” Miss laughed
“Yes Miss, thank You Miss.” I whispered frightened but not daring to fib.
Mistress knew this and often teased me rather testily about kissing Her visitors bottoms in greeting as She insisted I always do, unless the visitor forbade it. And often She might send me for the canes afterwards feigning or sometimes not feigning jealous annoyance. But in any case nearly always enjoying intimate service after my punishment. She would gag me with Her panties so I knew how aroused She was. The injustice and unfairness of the situation adding to Her enjoyment of my piquant distress.
“And it is so sweet sometimes sissy, I just love sending you off to wash my panties post climax.” She paused “Mine of course.” Both women chortled.
“Knowing you are aching so, is just so lovely, anticipating your tongue and your loving attentiveness, but also enjoying feeling the dominance & power of holding the key.”
“Yes Mistress, thank You Mistress.”
“Such a little splash too, even when we milked you it was a weak little squirt at the bottom of the wine glass, wasn’t it sissy.”
“Yes Mistress, thank You Mistress.”
It was a very small puddle in the glass, I was surprised how little there was after at least 3 months of teasing and frustration.
One of Mistresses friends had laughed, watching me purse my lips as I swallowed.
“Don’t worry about the weak taste sissy, my own sissy informs me that its much thicker and stronger fresh from a real Man.”
“Yes Miss, thank You Miss.” I had answered naively not realizing what She meant. It was shortly after that that Mistress and Her friend had started my fellatio training. Although until that point I had lost my oral and anal virginity to Mistress, there was still all that to come, or cum, with the Sirs before I was pink pantied.
And in fact when Mistress had first decided to take a lengthy vacation, I was fully pink pantied by then, and nearly fully feminized. Although I was still to be snipped and to grow small breasts under my uniform. When I was sent to the sissy hotel, where I was to serve as a sissy chambermaid whilst Mistress was away.
Mistress had teased me that the sissies chambermaids spend so much time on their knees and swallow so much real cum and testosterone. That the house Misses very generously give the sissies their own pee to counter this with their own female hormones. To drink in glasses at room temperature of course, rather
than hot and direct from Mistress as at home. This is not really true of course as we are on a regime of very strong hormones and estrogen and our dildo and chastity cages are infused with strong estrogen. The pee myth is just to tease us, not that empty headed sissies know any better. And that sissy should be very submissive and grateful to the Misses for this kindness. And do their very best to earn good tips, from intimate services, for the owner of the hotel, the house Misses and Mistress to share.
Of course there is no fear of that not being the case as on arrival, usually in small groups the sissies are given the hotel uniforms to wear, tight glossy, wet look satin maids uniforms. And then taken out and paraded for the guests. The new maids have to
each of the guests present and offer Her domestic and intimate services to each in turn. Sometimes rather embarrassingly the Sir might already have a maid between His knees when I introduce myself but that didn’t seem to spoil His enjoyment of her service or of my blushing introduction.
The chambermaid debutantes, so to speak, spend most of the afternoon swallowing cum and with sticky panties. On the first afternoon even extremely healthy tips are earned. As do they spend most afternoons, mornings evenings and nights. In between chambermaid & hotel duties. The Misses do seem to enjoy bossing and hurrying us a round with the aptly named very springy stinging hurry crops. And on occasion, though very rarely we might see the hotel owner, although only Her own sissies, who also serve as chambermaids are ever permitted to attend Her. There are female guests too but most sissies are not permitted to serve them intimately, although we do perform domestic and laundry duties. Mistress has teased me that because I loved hand washing Her panties so much I would enjoy hand washing all the other Ladies panties as part of my duties. In fact part of the ‘pleasure’ in the laundry room was that in the mornings at least one or two of the guests would come in and push one of the sissies face down into a mound of still to washed panties. Pull her panties down to gag her with,
then penetrate sissy, in front of all the other maids who would have to keep on working dutifully, the Misses would usually come and watch too. To add to sissies humiliation She would serve the misses and the male guest coffee afterwards before being dismissed, back to her pile of panties .
As such the atmosphere in the stuffy laundry room, was always one of expectant sexual excitement, even though we didn’t dare admit this even to ourselves, and fright, sex and fear.
The sissies boarding actually pays for itself with the guest paying premium fees for the luxurious hotel and service, And generous tips for the intimate service of the sissies making a nice profit to be shared. The sissies should always bear this is in mind while being permitted the privilege of serving and pleasing the male guests. Grateful that their superiors will be enjoying holidays of their own and luxuries with the tips earned. When we return home we are given a tiny pink leather handbag no bigger than a purse, containing a receipt of the breakdown all our tips and Mistresses share. The purse is locked and only Mistress opens it after we hand over our ‘pin money’ to Her.
We are teased that an additional benefit accrued from the experience of serving all those different Men and sharing experience and techniques with the other sissies. When the sissies are allowed to chatter, sometimes when working they are limited in the topics permitted, to serving their Mistress, domestic service and serving the Sirs as well as their own little slave girl fantasy stories. A well trained and subjugated maid has little room in her, pretty head for anything else anyway, even though she is also an air headed little bimbo too. So that when sissy returns to her owner house sissy will be able to please her own Mistresses boyfriends and male guests with all the new tricks she has learnt. Which is lovely for her, as she wants to be a good girl or good maid for her superiors especially during sex, but more importantly for Him and His sexual enjoyment of course. And for Mistress the cunnilingus is fantastic for the next week or so.
“Ah yes.” Mistress sighed happily thinking about Her vacation and Her welcome home.
I glanced down seeing Her wiggle excitedly which made me suddenly even more aroused.
“More wine sissy.”
“Yes Mistress, thank You Mistress.” I curtsied
“And lots more lip gloss sissy my boyfriend will be here soon sissy.”
“Yes Miss, thank You Miss.”
Mistress also increased the size of my dildo. It was so engorged now So I felt like it was throbbing and I was about to burst.
“Nice and squirmy sissy, so you will mince & squelch prettily for Him.”
“Yes Mistress, thank You Mistress.” I curtsied feeling myself squidge and squelch wetly.
“So sweet, I could fuck you myself sissy.” Miss said.
“But I will just have to settle for gagging you with my, I must quite frankly say soaked panties when my boyfriend fucks you, sissy.”
“Yes Miss, thank You Miss.”
“Are you getting a little exited in that tiny chastity cage sissy,” Miss teased
“Oh that is very flattering sissy, but you can fetch the canes later sissy.” Mistress said.
“Yes Mistress, thank You Mistress.” I gulped &
curtsied, knowing that Mistress was aroused Herself and would be even more aroused caning me before and afterwards.
“Life is just so
wonderful, especially my sex life.” Mistress said happily,
“Yes Mistress, thank You Mistress.”
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