At the start of Mistresses vacation, or business trip, We are collected and taken to the hotels by the delivery chauffeur service. I had been packing Mistresses things for few days now, as She has been telling me snippets about Her intended trip, and of course chatting to Her friends. Not really telling me too many details or for how long She will be away, as that is not really any concern of Her maid. She might have left aready leaving me in tears to tidy & clean the house, waiting to be collected. I will often be one a few maids being delivered at the same time. Today there were 5 of us in total, I was second to last being collected. The drivers or chauffeur team was a Man and a Lady. He driving, She sat in the bucket seat, watching and supervising us maids all squeezed onto the rear seat. She was wearing a rather lovely uniform with a business like but short leather skirt. He in a very well fitting traditional uniform that clearly showed how well endowed He was. The male staff even if purely vanilla are often chosen for these attributes.
The Miss was rather offhand and disinterested but strict, we were to sit in prim silence, unless we
wanted to be gagged with our panties. We were all tearfully anxious and upset at the thought of being separated from our Mistresses, some maids might also have a Master as well as a Mistress, for this length of time. But Mistress knows best and any superior knows better than a sissy, She deserves Her vacation time.
And think of all the new tips we would earn so She could buy Herself nice new treats. We might even get a pretty new apron, uniform, or nightwear too. And think of all the tips techniques we could learn, to better please Her, Him or Her boyfriend.
We were sometime allowed to chatter and catch up when we were working together, as long as it didn’t interfere with our duties or disturb the guests. There were always titillating little stories to share, even if they weren’t quite true they were all very exciting. At first with other sissies a new sissy is very shy and embarrassed. Especially as she must always greet fellow sissies with a curtsy and a squeeze & full kiss on the lips, always hold hands when walking closely together, very effeminately. But quickly she will learn that she has no choice but to effeminate and girly, girly. And even though we are still always not only uncomfortable with other sissies remembering that we were once ‘males’ in the loosest sense of the term, and also now very jealous of each other and competitive, it is still comforting to share a whispered moment or even a comforting cuddle after you have been punished or dismissed in tears.
When we had arrived on site, the Lady chauffeur had led us all into the general kitchen area while the male driver watched. There was a loud crack of leather on bare thighs and a squeal of pain and fright, then another loud crack followed by another frightened squeal.
“Do hurry sissy I don’t have all day.” The driver said testily.
“Yes Miss, thank You Miss.” The poor maid replied you could hear the tears and misery in her voice, but none of us dared look around.
We were so glad it was her and not us, and terrified it could be us next.
“Face the wall sissies, do hurry.” The driver said
“Yes Miss, thank You Miss.” We all chorused together.
We all stood perfectly upright straight. Toes, noses, nipples & chastity cages, just touching the wall. Holding the hems of our dresses in curtsy cuffs.
There was another crack of the whip but this time just on Her boots as She looked us over. Then finally
satisfied he left us standing facing the wall.
It was just before lunch and all the other chambermaids were all busy. A couple of the male guests had made various unnecessary trips just to see the newly arrived maids all facing the wall as we waited.
One of the house Misses came in to the kitchen.
“C****” She said warmly “How are you ?”
“V****, how lovely to see you.”
We could hear the conversation, but auto conditioning prevented us from hearing the names of our superiors, it was just a blur.
“I thought I heard your voice and whip crack.”
“Yes quite, one of the maids was just a little slow this morning.” She laughed.
“Oh, our chambermaids aren’t allowed to be slow at their chores, busy, busy like good little maids.”
“Time for coffee ?”
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“Oh yes of course, always time for coffee and a chat.”
A small service bell was rung and a chambermaid hurried into the room to serve coffee.
The female chauffeur and House Miss sat down for coffee cigarettes and gossip.
“And how is your wife ?.” The driver was in a lesbian marriage
“Oh She is doing very well, career is keeping Her very busy.”
“And your new sissy ?”
Some chastity sissies were only allowed domestic service, & maybe to clean up after sex, in the beginning. Although they might get to serve Sirs or Masters in the hotels or clubs. And maybe as time went on be expected to perform more intimately in the home too.
“Oh S****** is getting used to the sissy now, She wasn’t sure at first, but She loves coming home to an always spotless house cleaned by our sissymaid.”
“Yes it is lovely and perfect to come home to a sissy clean house.”
“I cant imagine how demeaning it must have been to be a 1950’s wife, having to keep everything even nearly like that for a boring husband, or any Man for that matter.”
“Yes quite, but maid service for those otherwise boring husbands and unsatisfying ‘men’ is so appropriate.”
“And the cane is such a perfect cleaning incentive.”
In a household with a sissy maid there is no need for any labor saving devices as sissy performs all her
chores , or as many as physically possible, by hand. ‘The only tool a modern woman needs for a spotless house is Her cane’ as the popular advertisement slogan goes
“And nearly always satisfying too, after a long day.” She laughed “Speaking of which S****** is actually taking an interest in acquiring a nice big strap on.”
“Ohh.” The House Miss almost giggled “And how do you feel about that ?.” She teased
“Not for me, or Her of course, but for sissies tight little ass.”
“How perfect.”
“Oh yes just thinking about that has made me a little moist.”
“Even more perfect, something to look forward to later.”
“Hmmm, yes.”
She had two chastity devices to deliver and supervise fitting later, but those sissies could wait. The anticipation would only increase the sissies sense of anxiety at being locked up for the first time. And making the little dears wait was a good foretaste of their very inferior station in life. And although neither of the sissies was available for oral service, except to their future owners. It was always arousing to lock a sissy in her first but not her last chastity device.
The male chauffeur obviously not totally vanilla or at least immune to the charms of very feminine/effeminine chastity chambermaids had called over another chambermaid for coffee and fellatio.
Even most vanilla Men enjoy fantastic fellatio with sissies, once they get over that initial stage of seeing us not as males but as a third effeminate submissive sex. We are trained and eager to be as totally obedient and pleasing as possible, everything at that moment is for His pleasure, like an animated compliant sex toy.
In fact I supposed the driver might have been vanilla as He didn’t spank the maid before fellatio, often vanilla Men are reluctant to spank us & need encouraging, whereas most of the Masters always spank us before a BJ and often before anal too. Of course it might mean that He was just to eager to cum in Her face too. Most Men whether vanilla or not enjoy blowing our faces and watching us swallow when given permission.
He was sat very close to where we were standing, and we could hear the maid telling Him how big His
shaft and glans were and how full and swollen His manly balls felt as she sucked and kissed them. How wonderful He tasted and smelt, and how wonderful it was to be chosen by Him, and how she hoped she would be able to please Him. That is until He finally splashed precum in Her mouth and face and silenced Her properly by pushing His engorged cock deeply into Her mouth. In the background we could hear the lady driver and the house Miss drinking coffee, chatting and gossiping casually.
We were all so jealous but didn’t wouldn’t dare ever to admit it even to our selves. And after He had finished and she had finally been permitted to gulp & swallow, thanking Him through sticky lips. We were all quietly but helplessly squirming on our plugs as He slapped Her bottom and dismissed her.
Then He had joined the lady chauffeur and one of the Misses having coffee, laughing after enjoying His freebie or staff perk.
It reminded me and I’m sure some of the other maids, of the times before were fully domestic. And often lived in special apartments for sissies in training. The chauffeurs or delivery drivers would often visit to bring us new chastity tubes, treatments, underwear plugs, lots of different things. Although it was mainly lady chauffeurs who brought and supervised us locking new smaller intimate devices, often there would be a male driver too. And we had heard stories about how one time, one sissy had been locked then the drivers had decided to fuck on sissies bed, leaving her to clean up the wet patch after they had left. Or how a male driver had wanted & forced fellatio from sissy. And/or been anally violated, sometimes even pegged, and sometimes by a couple of lady drivers in turn. Sissy wouldn’t have known this but her future Mistress would have allowed and approved this as part of how She wanted Her sissy trained.
Later when sissy ashamed and distressed confessed to Mistress what had happened sissy would be punished for bothering the superior with such nonsense.
We had all wanted to taste Him, to look up at Him as we swallowed His thick sticky load and thanks
Him. And we all knew it and much more embarrassingly knew that all the other maids knew we wanted to as well.
He had actually slapped one of our bottoms as He left too, I had been so jealous, listening to her squeal of shock, her false protestations of modesty, but also thanking Him.
“Be quiet chambermaid.” The house Miss said sharply
“Yes Miss, thank
You
“And all of you maids wait quietly.”
There was a loud swish and crack of leather on leather as the crop landed on the side of the couch.
“Yes Miss, thank
You
“Oh you are so strict with them.” The lady chauffeur laughed.
“You can never be too strict with chastity maids.” She paused and laughed “But oh yes, I am.” The chauffeur laughed .
After the chauffeurs had finished up and left, the house Misses left us waiting for quite a while longer.
We were finally allowed to turn round and were inspected. Not before the maid who had served the chauffeur was summoned back. There was a tiny spot of cum on the seat He had been sitting on. She hadn’t seen it because He was sitting on it before He left. Nonetheless sissy was bent over holding Her ankles and given six strokes with the crop before licking the cum off the chair and polishing the chair with Her panties. All this in front of us as if to serve as a swift mnemonic for our expected service. And even though we had all been chambermaids before, we all looked on aghast and frightened.
Our new chambermaid uniforms were handed out and inspected for correct fit and length. At least 2
sizes too small and very short at the hem. The bottom of our panties visible under our skirts when standing still, breasts nice and buxom, seemingly ready to spill out at a moments notice. The uniforms were all black with white trim and apron, but with pink panties. In some hotels and clubs the maids wear pastel colours with matching panties, chastity, plugs and maids booties, even the maids hair is dyed to match. Usually with white or cream trim apron and maybe maids headpiece.
The Misses watched us coolly as we shimmied into the tiny glossy uniforms, watching us curtsy and smooth our aprons down, slightly smirking as they watched us trying in vain to smooth the hem down just a little bit further on our thighs.
Like the pretty slavegirls in our fantasy stories, suddenly being dressed in very skimpy slips or wrap skirts, and embarrassed at the brief diaphanous clothing trying to
Pull the hem down a little, especially as slavegirls are not usually permitted panties. And the neckline up a little higher. Only then to be told by their Masters that the outfits are a little modest for slavegirls And the hem shortened dramatically , and the sides slit and the cleavage opened up as vividly as is significant. Or being given much tinier and impossibly more glossy and diaphanous garments to wear, to their utter dismay. Or I suppose being stripped nude to serve. Whereas the pretty little imports might have worn sexy little outfits, when they foolishly thought they deserved the choice in how they should dress, before they were ‘acquired’ intended to subtly titillate and tease, here they would be expected to tantalize and fully satisfy the Masters lustful intentions aroused when pretty slavegirls entering a room with their Masters or be punished. Just like sissymaids in our so very short uniforms.
“Wiggle prettily maids.” We were told as the Misses walked around us examining us, lifting the hem of our skirts with their crops, having a feel of our chastity locks and the base of our butt plugs. Making us feel even more helplessly vulnerable.
“Yes I think you will all be very popular with our guests”
“Yes Miss, thank
You
I heard a little laugh from one the Misses.
And eye candy for the Female guests, even though we would only be serving the Ladies domestically.
“A pretty little fantasy for our guests.”
“Yes Miss, thank You Miss.”
“And you will satisfy that fantasy fully wont you maids.” She said toying with Her crop
“Yes Miss, thank You Miss.”
We were to address all the male guest not as Sir but Master, now that we were all fully snipped, and even for Mistress to regard Her as Miss, as that is a more effeminate and appropriate form of domination for chastity sissies. Although still in company She was still Mistress and all other Ladies were to be addressed as Miss.
Our plugs were to be kept fully enlarged while we were serving as chambermaids enhancing our wiggle and mince for the Masterful guests. Again this was auto suggestion as the plugs didn’t vary in size at all in reality. But felt positively bulbous now. The ultra slippery estrogen infused silicon, felt like it was pure KY jelly and incredibly difficult to hold, as well as feeling massively invasive & penetrated.
The effect was to make us constantly & desperately try to squeeze our buttocks and upper thighs together as we walked. Mistress and Her friends used to tease me terribly when they were expected male company who would nearly always want at least fellatio but also anal. Watching me as I quaked and shivered with vulnerable fright at being bent over by Him, involuntarily trying to clench my bottom on my plug in vain.
“What a pretty little squelch sissy.” They would laugh “I’m sure Sir will be pleased to see you are so looking forward to serving Him.”
“Yes Mistress, thank You Mistress.”
“I will tell Him you need a good firm spanking for getting so excited sissy.”
“Yes Mistress, thank You Mistress.”
“After all you are for His pleasure not your own silly needs sissy.”
“Yes Mistress, thank You Mistress.”
The effect of the plug, combined with the very tight pink panties was to make us mince and squidge even more delicately & very prettily. The satin panties were highly glossed on both sides of the material as were all our petticoats and uniforms, for a very shiny sexy and slippery look and feel. As the slave girls in their tiny tunics, from our stories, would exclaim felt like being more naked than naked.
After the two Misses were satisfied we allowed to fix our nails, cosmetics, rouge blusher & lots of lip gloss, then spray ourselves with cheap but sensuous perfume.
Our makeup is somewhat water resistant. Mistress can get rather moist for cunnilingus and soaking for queening, and She does enjoy dismissing us back to our chores, still soaked with Her arousal, tasting and smelling it all day. We love it too, even though we might require a slight touch up. Similarly the male guests like to blow in our faces and dismiss us, with sticky breasts, décolletage and faces shining needful, and in tears.
Of course the House Misses will take us into one of the side rooms and we will fix our make up quickly, supervise us while we wipe down our uniforms, apply lots of lip gloss. If needed administer a very quick hot scented chemical enema, Everyone likes to dismiss a sticky pantied maid, well most do anyway. But no-one wants to be served by a used and sex soiled maid, unless of course it’s a group of Men enjoying a sissy together. Even though the enema leaves us very clean the effect of the enema and the lube still leaves us feeling very sticky, squelchy and self conscious.
We would be allowed to shower and have a proper enema every morning and evening. And toileted once in the evening, this was usually just pee as our strictly controlled diets did not generate much if any fecal waste. Being allowed to pee was a privilege and could be delayed, postponed or even cancelled for the day if the Misses felt they were busy, or if they wanted to humiliate or punish us. Not being allowed to pee in the morning would make us very squirmy and enjoyable for the Masters, when they groped and fondled us.
Another aspect of the dildo plugs is they press against and massage your prostrate constantly as you
hurry about your chores. This is very good for the glands health, but you constantly feel as if you are just about to, on the verge of cumming, which is not permitted for chastity maids. And constantly feel as if you need to, or are about to pee, or wet yourself, which again is only permitted when the superiors allow it. This as well as the constant penetration makes you feel even more vulnerable and adds deliciously to your mincing wiggle.
“And after all what is much more important, to chastity chamber maids, your Masters pleasure and enjoyment, or a little discomfort for you sissy ?”
“Always Masters
pleasure Miss, thank You
But then one maid blurted out and burst into tears. As soon as she spoke, you hear the absolute panic and fight in her voice, now wishing more than anything the world would swallow up her feeble little protest.
“Please Miss, my Miss didn’t allow me to pee, pee last night or this morning Miss, She said She was too busy and that I must wait till I get here Miss.”
There is always one silly maid, with a silly question, and quite often it is myself but thankfully not today. I had noticed her in the car, squeezing her thighs together. Maids do get very attuned to each others distress and she had made me need to go quite desperately too, and I suspect the other maids.
“Well no doubt your owner was too busy sissy, and that was Her concern wasn’t it sissy.”
“Yes Miss, She was with Her boyfriend Miss, thank You Miss.”
“Your owners boyfriend, sissy, Sir or your Master, sissy?”
She was trembling and feeling so very small and powerless, utterly regretting saying anything at all now.
“He is my
Master, Miss, Yes Miss, thank You
Miss slapped the side of Her boot with Her crop and made a sharp tsk sound.
“And did you think to bother them with your trivial distress, sissy.”
“Yes Miss, No Miss I did not Miss, thank You Miss.”
“And your superiors did not think to mention it, sissy ?.”
“Yes Miss, No Miss they did not Miss, thank You Miss.”
“Well no doubt it was of little unimportance to your superiors, sissy.”
“Yes Miss, thank You Miss.”
“Anticipating their vacation as Mistress and Master would be, maid.”
“Not your silly needs and desires sissy.”
“Yes Miss, thank You Miss.”
“As trivial and unimportant as they are to me sissy,”
“Yes Miss, thank You Miss.”
“And to our guests, sissy.”
“Yes Miss, thank You Miss.”
“But you accompany me to the toilet sissy as I do need to go, and don’t require permission.”
“Yes Miss, thank
You
She would be wiping Her after She had peed with a paper towel off course. But not as is sometimes the case kissing or licking the superior clean. This was usually just for pee of course, excrement was a little vulgar to most. And in any case were only allowed to clean the Misses with paper or silk towels, or to kiss them through their skirts or panties, never on bare flesh as that was for only Mistress.
When they returned the sissy was holding a rather large tumbler of warm & quite yellow pee. It was thick and a little stinky too, as Miss had been drinking strong coffee all morning.
“And you may drink that sissy, all for you this time at least.”
“Yes Miss, thank You Miss.”
“Quickly now sissy.”
“Yes Miss, thank You Miss.”
Mistress tells me that the best hormones for sissies is Her fresh pee, failing that Her pee stored at room
temperature, and although I am sometimes allowed a weak cup of milky very sickly sweet tea in the morning, with my unbuttered crustless toast, for breakfast. For most of the day and evening I have Her pee. This isn’t quite true or even remotely true of course compared to the very strong hormones and estrogen, but She enjoys telling me and She enjoys peeing directly into my mouth especially after pegging me, or if She is enjoying multiple cunnilingus sessions.
I will bring Her a fresh wine or whatever She is drinking and She will reward me with Her lovely pee. And I do love it so fresh from Her, it feels so very intimate.
But here in the hotel as we will be performing our duties and serving the Men, performing oral duties. The chambermaids will swallow so much cum, that there might be some testosterone feedback. Especially as it is so thick, sticky and copious from real Men. There is so much fellatio, as well as licking the Masters clean after anal, sometimes as many as 20 thick full mouthfuls per day, that it really isn’t necessary to feed us very much and also not much need for break times, unless it is to quickly refresh our makeup. Sissymaids are not generally permitted breaks or days off and the hotel is always very busy. But there is so much cum to swallow, and although you have to quickly refresh your mouth with wash after fellatio, you still feels sticky and gummy all day. The house Misses also very generously agree to pee into containers for us sissies to drink, during the day, and we must be very thankful. This reminded me of my training time in the office, when the Ladies would give me jars of their pee to drink, and their panties to hand wash as well as my other office duties.
This is of course all nonsense but if Mistress says it is so it is always so.
Incidentally we are never allowed to drink the Men’s pee, although we can often taste traces when we are sucking the glans. But naturally we are allowed to gratefully swallow His precum, which it is stressed has an element of pee and is a perfect drink for a sissy.
Bringing Sir or Master a cool beer or whatever He snaps His fingers for and kneeling and swallowing His hot splash precum. It is nowhere near as thick as His cum, but is still much thicker and more copious than a sissies pre chastity splash, ever produced. & we are so happy, even though we are totally shamed to swallow this as it is a confirmation that we are pleasing Him, and a taste of His pleasure to cum.
“Thank you Master.” We will whisper through often glistening lips, He does like to smear the precum on our already highly glossy lips.
“The pleasure is all mine sissy.” He might say, often He might say that after fellatio or sex, and you have thanked Him, when He dismisses you.
“Yes Master, thank You Master.” You always reply, with a curtsy and if you are on your knees with a
little symbolic curtsy, even though you are cuffed you are still expected to hold the rear of your dress in your fingertips as best you can, and squelch on your dildo.
He might slap your bottom loudly if He is dismissing you, or simply say nothing, you are only a maid in chastity for His pleasure and firmly in your place.
The maid finished the large tumbler of pee and curtsied
“That’s much better isn’t it sissy, nice and topped up now.”
“Yes Miss, thank You Miss.”
“You may lift your dress and petticoats now sissy and hold your ankles.”
“Yes Miss, thank
You
“The rest of you may face the wall.”
“Yes Miss, thank
You
She was given six lashes then another six for good measure.
“That will do for now.” The Miss said with an air of satisfaction
“Yes Miss, thank
You
The other maid who had been lashed earlier was told to bend over holding Her ankles, She was sobbing as a pair of soiled panties were pressed into Her mouth.
She also received six, then a short delay, while pain from the first six bloomed and spread over her exposed behind another further six lashes. I say six but because of the effects of the hormones and treatments sissies are not able to count above 2 or 3 without everything becoming confusing and hazy. Nonetheless it still feels like an awful lot. Similarly although we can just about with some difficulty now read recipes, reading slowly aloud, anything else is just a blur. In fact Mistress has on occasion shown me something on Her tablet or newspaper and I have looked blankly at the random but pretty patterns. Until She has laughed and remembered
“Oh of course, I forget sometimes, never you mind your pretty little head sissy.”
This feels so patronizing but comforting too, as I curtsy and say quietly
“Yes Miss, thank
You
Mistress has said that ideally it wouldn’t be necessary for sissies to learn to read or write at all, just taught domestic subjects. Also we should never have been allowed to masturbate, even before chastity. How this might be achieved is another matter but this is what She would want if possible. Even though She does enjoy the thought of us longing for what we once so very treasured. Even while real Men, not just sports jocks but manly intelligent spontaneous confident Men, were having sex with beautiful young women we would be furtively masturbating and longing with those same hot girls.
We could all now smell the sex and fear in the air, and waxy smell of Miss Her exertion and arousal. She looked very satisfied, with the results.
“We cant have tardy chambermaids here can we sissies.”
“No Miss, yes
Miss, thank You
“So I think as a lesson to you all, it will be tippy tiptoes for you all today & until further notice.”
“Yes Miss, thank
You
“And a short hobble strap, lets say 3 inches for now.”
“Yes Miss, thank
You
“After all the Men do enjoy chasing you a little but not too much.”
“Yes Miss, thank You Miss.”
“And a little struggle is always quite winsome for chastity maids, isn’t it maids ?.”
“Yes Miss, thank You Miss.”
In actual fact all the chambermaids always had their hobble straps at 3 inches and always hurried about on tiptoes. The effect is like having our panties wrapped around our ankles, which they often were. The pretty slavegirls in our fantasies are often kept in toe cuffs for the same purpose.
“That’s all very good then. Now lets introduce you to our guests, I’m sure you are as eager to start cleaning and serving as the Masters are to start enjoying your intimate services.”
“Yes Miss, thank You Miss.”
We were instructed to hold hands prettily and were led out
into the Mens main lounge. There were several lounges some for couples Mistress & Masters, or
Mistress and vanilla guest or vice versa, and some which were specially for the male guests who wished to be entertained by the sissies. There was already quite a few Men seated waiting there, and there was an intimidating cheer and few whistles as we minced into the serving area in front of them.
As I saw the full room, by bottom tried to clench around my plug, which felt huge but I just felt a wet squidge, I wanted to run away and be taken home already. The other maid was holding my hand very tightly, feeling exactly the same.
Curtsy
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