The vacation

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A visit from the office.

 

Mistress had come home excited again. It was Hers and our time of the month and She was nearly always extra rampant at this time of the month. I was also extra horny and intensely emotional, squirming constantly in my cage and on my plug.

For extra intimacy She had ordered me to Her bedroom and fucked me on Her bed. Then I had gone down beneath Her thighs for a longer slower follow on orgasm.

While She showered I changed the sheets for freshly ironed sheets tidied the room  and took Her discarded clothes down to the laundry room. Then I had hurried back to dry Her with soft towels and help Her to dress. Kissing Her bottom as She put on fresh panties and a soft leather mini skirt, it was

pastel blue and very modern and stylish. I found the way the sheen of the leather hugged Her thighs very sensuous and very exciting. 

We were having guests over. I got quite a surprise when I opened the door and Miss A from the office was there. After curtsying and kissing Her bottom I took Her jacket and brought Her and Mistress chilled wine and snacks. Miss a liked small form fitting leather jackets with matching skirts, matched with white silk blouse She looked very businesslike but sexy too.

Miss A took Her wine with an indulgent  smile and dismissive wave. Around sissies ladies act naturally

and justifiably very entitled. This is only  just and proper after all we are there to serve them and should expect to be punished if we fail to please. She patted my bottom &  told me how lovely it was to see me in a proper maids uniform and with my chastity bump so tiny and unobtrusive now.

How long had it been She asked. And in all fairness I was surprised to think that nearly 2 of Mistresses birthdays had been and gone while I had been Mistress sissymaid & sissywife. When Mistress had first taken complete control of my chastity I had counted every day, in fact sometimes it had felt like I counted every minute of every hour of the day. But Mistress had only permitted me to be milked then stopped that too and now I just ache constantly & helplessly for what is appropriately denied to a sissymaid owned by a Mistress.

I wasn’t allowed to watch the TV or read newspapers and being Mistresses maid was 24/7 so I had lost count of the weeks and months. It had been well over a year since Mistress had stopped milking me and hadn’t decreased the size of my cage since that time either. Any tinier and it would look like it had been already clipped  sissy She told me.  Mistress liked to tease me with stories of sissies who had been clipped or gelded, usually sissies who were owned by men, but not exclusively. It was the dominants choice after all. Which terrified me even though I knew in my heart of hearts that Mistress would never let me out of the cage unsupervised. But also that She preferred me in the cage when pleasing Her or one of the men. Because tiny and soft as I was my clitty still gets very swollen and tight in the cage when I am serving intimately or thinking about Mistress. And makes me very attentive & obedient afterwards. Plus Mistress loves knowing She wont allow me to cum while She orgasms on my face. For the real men, they  like to know I am totally locked up when I am on my knees performing fellatio or for anal, it totally reinforces that this isn’t a gay thing and that I am there for their pleasure as a sissy.

Mistress and Miss were working on mentally conditioning me to get excited in my cage when thinking about a Sir coming over. It was working and I didn’t like it at all, much to their amusement. 

Miss A had me stand near Her and curtsy then laughed loudly at my apron smoothing gesture. Patting my bottom firmly She said that Miss had told Her all about it and it was indeed very cute and quite pathetically sissy too. She took a video of my curtsy for the girls in the office and then showed me all the amused comments as they came in. Some of them were from the girls boyfriends and were quite lewd.

Still patting my bottom Miss A and Mistress discussed pegging. Miss A said She absolutely loved it and pegged every sissy She got the chance too. She said She wished Mistress had allowed Her to peg me when I was ‘working’ for Her in the office, and being supervised by Her. Some Mistresses allow other ladies to enjoy their sissies but for most sissy is strictly monogamous to theier female owner. Serving Real Men doesn’t usually count.

Miss A said that they had a couple or three office sissies to be trained since me. Since then most of the sissies had been kept in formal maids uniforms rather than trousers like me. My tight fitted matt satin slacks and shirt were Mistresses choice so that I felt uncomfortable and sissy around the men in the office. 

One of the recent sissies was pegged every day in the office by at least Miss A and usually a couple of the girls. Although She was no longer in the office but was Her Mistress house sissy now.

They also had a sissy who was subject to corporal punishment and was caned, but not cropped  regularly. Of course the sissy who was pegged regularly was also caned regularly too.

Mistress also kept that for Herself as caning and cropping  me was intimate between She & I. The only other woman who was allowed to punish me was Miss when She was looking after me when Mistress was away. But I have been told that eventually if & when Mistress goes away for an extended holiday I might be employed as a room and daily maid in one of the clubs or hotels and the house Mistress there could and would punish me as they pleased. This hadn’t happened yet but I was dreading Mistress that time.

 

Miss A had asked My Mistress to show Her the canes She used. Mistress told me to hurry and fetch them. Behind me I heard both ladies laughing at my panic stricken mincing steps.

Miss A examined the canes and expressed satisfaction that they appeared to be well worn and used. She sat there flexing the cane while I stood in attendance squirming in front of the two ladies.

‘I always thought you should be well caned sissy.’ She told me.

‘Yes Mistress, thank you Mistress.’

‘Are you kept well caned sissy ?’

‘Yes Mistress, I am Mistress, thank you Mistress.’

‘Excellent I do like to see a sissy kept in perfect discipline and fearful of the cane.’

‘Yes Mistress, thank you Mistress.’

‘I keep my own sissy is so sweet and timid, so fretful of the cane.’

‘Yes Mistress, thank you Mistress.’

‘The cane is natural complement to a sissies housework, isn’t that so sissy ?’

‘Yes Mistress, it is Mistress, thank you Mistress.’

‘And so it should be isn’t that so sissy.’

‘Yes Mistress, thank you Mistress.’

Mistress and Miss A continued to chat relaxing waiting for Miss A’ boyfriend to arrive.

Sissies should perform all their individual household chores fearfully almost choking with fright and fluster, at the caning they will receive if anything is unsatisfactory. Nothing is as lovely and clean as sissy clean, you can almost smell the fright in every polished gleaming surface, Mistress would often tell me.

This corporal punishment wasn’t cruelty, but for my own good and for Mistresses happiness. An obedient, intimidated  sissy is an good sissy.  

Mistress told Miss A that She wouldn’t allow Her to cane me, mainly because Miss A would enjoy it too much but that as Her boyfriend was coming over shortly He could cane me instead of spanking or paddling me.

That was a lovely compromise Miss a and Mistress laughed. I saw both ladies shift in their seats excitedly at the prospect while Miss A laughed and patted my bottom again.

Then would hand launder them for Her afterwards. As a thank you to Her for bringing Her boyfriend round so I could serve a real man.

Miss A showed Mistress and me a couple of photos of the latest office sissy. She was very pretty and petite, with very short dark hair cut very short and elfin, which was an unusual style for sissies but Her future Mistress said she  looked so lovely it would be shame not to keep Her hair like that.

She also wore a very pretty but plain maids uniform very short and sweet. And Although Miss a nor none of the girls were allowed to cane or peg sissy. Mistress came by the office most days and spanked sissy over Her knees in front of everybody, including any men who were present. She also had no formal work in the office apart from serving drinks, cleaning and fetching and carrying, but every day the office girls would give her their panties to hand wash that evening, to be returned the next day washed ironed, scented and folded neatly. And handed over with a curtsy and thank you to each of the girls.

Miss A said this sissy was so virginal and innocently excited, just like I had been. And also like myself very naturally submissive and timidly shy around women and dominant men.

Already Her Mistress had a card with lots of Men who wanted to visit sissy, when she was pink pantied, a maid, made to serve  Mistresses male friends .

Not all sissies were pink pantied, but most were, once again it was Mistresses choice.

Mistress and Miss A smiled at the prospect at sissy getting Her first mouthful of cum and the prospect of seeing it all over Her shocked & humiliated pretty elfin face. Mistress didn’t usually like to see me creamed or iced with Sirs cum. But was amused by the pictures Miss had of me with Her boyfriends cum all over my face and especially on my pink nightie.

She opened up the app and showed Miss A the pictures, both women giggled with amusement.

‘Oh sissy, do you remember your first mouthful of real cum ?’

‘Yes Mistress, thank you Mistress.’

‘And the first swallow, how thick and sticky it must have been for you sissy ?’

‘Yes Mistress, thank you Mistress.’

‘I remember how excited you were, that tiny little pathetic dribble in your panties sissy.’

‘Yes Mistress, thank you Mistress.’ I blushed and squirmed in shame.

 When Sir did come over later He seemed modestly amused to see me and told me that He knew  I always secretly wanted to suck His manly cock, like all pathetic sissies.

Miss A had gagged me with Her panties while Sir caned me. And then with my mouth still sticky with Sirs cum, gagged me with a second pair of Her warm panties when Sir took me down to the laundry room to roughly bend me over and spread my legs to fuck me on top of all the freshly washed and ironed clothes. Which I would have to wash & iron all over again.

This was one of Mistresses and Misses innovations, which had become very popular with Her friends too. If one of Mistresses female friend brought one of their boyfriends over the Lady would gag me with Her still warm panties if Sir wanted to gag me when punishing me & always to gag me for anal sex, Mistress liked me to be always gagged for penetration. She enjoyed hearing my pathetic sobs of protest and moans. But enjoyed it even more so hearing them muffled.

Afterwards while I was washing and laundering Her smalls I was to think gratefully of being allowed the privelege of serving Sir, how best to improve my service to my superiors and gratitude for Miss for bringing Her boyfriend over. After all my service was Mistress hospitality.

Miss A's boyfriend was another man who came an awful lot and it was very thick and sticky, maybe even more so than Miss's boyfriend. Quite difficult to swallow and He had left my panties feeling very slimy and sticky.

After Sir finished with me and I had served Sir and the Ladies fresh drinks I was sent back down to the laundry room to wash and iron all the messed up clothes again.

Sir had slapped my bottom and told me that He enjoyed caning me & seeing me on my knees licking His cock clean after he had fucked my pretty little ass but he was finished with me now & I should get back to my housework now.

Miss A had smiled indulgently as went off in nearly in tears

‘Quite a pathetic little bimbo sissy is now.’ She said

‘Yes quite delightfully so.’ Mistress replied

‘You have trained Her so well.’  

‘ The crop helps.’

“And the cane.’ Sir laughed.

They all laughed

'But she is just another sissy bimbo to fuck.' 

'Quite so, but thank you.' I heard Mistress reply a little tartly, to more laughter

'A good little suck and fuck though.'

'Well you are most welcome to cum again.' 

I heard Mistress reply & Sir laugh

I hurried off in tears my panties sticky with his cum to hand wash Miss A panties and the rest of the laundry.

After the guest had left Mistress didn’t summon me till much later, when She wanted me to dress Her in Her evening and bedtime lingerie. Then She told me to go a put my pink nightie on and to fetch the pink cushion.

I had wanted to please Her so much that evening and She allowed me to kneel next to Her kissing Her thighs softly after She had climaxed multiple times.

That night She allowed me into Her bed to cuddle and spoon, as She often did at this time of the month.

She did send me back to my own little room in the middle of the night though as it pleased Her to do.  

I must confess i am including the video because i just love the shiny black panties and the moaning.

 

Harem App

 

Mistress and Miss were chatting. Miss had noticed that I was looking very flushed and squirmy and commented on it amused.

Was I excited to see Her that much ? She asked.

Or did I enjoy kissing Her sexy bottom so much ?

She did nearly always wear lovely leather skirts, and Her bottom like Mistresses was almost perfectly rounded and well toned. Mistress expected me to kiss all Her female guests on the bottom when greeting them and saying goodbye, with  a curtsy then kneeling behind them, for a soft respectful kiss on each cheek, and another curtsy.

Miss would always wiggle Her bottom teasingly as I knelt behind Her kissing Her bottom.  

Or was I excited because Her boyfriend would be coming over in a short while ?

Did I love looking up from my knees sucking his big manhood so much ?

Or love swallowing His thick sticky cum on my knees looking up at Him ?

Or love being bent over and penetrated, feeling Him inside me so much ?

Miss and Mistress both knew I found male visits very fraught and emotionally sexually  embarrassing. Mistress always laughed &  teased me not to be so demure & prissy. Sissies should love the privilege of serving and pleasing a real man. And Miss would point out that  I always squelched and grinded on my plug so excitedly  & passionately while sucking Sir deep in my mouth. Mistress had guided and insisted that I  squirm and squelch on my dildo when I was between Her thighs. Matching the strokes & rhythm of my tongue. And Mistress said I had started to do the same  naturally when I was performing fellatio, even before She had instructed me to. Even though She had told me to start & keep doing it, because it pleased Sir to see me so eager to please Him.  

Also Mistress & Miss pointed out that I always had a tiny bit of inadvertent watery leakage in my cage, so I must love serving real men.

And if Sir was in any way displeased, or dissatisfied  with my service Mistress would immediately send me for the crop.

I was squirming with embarrassment when Mistress had described in detail how  Her She had come home early and pegged me.

Mistress had gotten quite excited by the prospect of pegging my cute tight ass that She had left the office early and driven home. She had climaxed loudly inside me then sent me back to my chores as She knew Miss was coming over. Often Mistress likes me to kneel between Her thighs afterwards for another longer and slower orgasm. Especially as I am always especially emotional and vulnerable after She has climaxed inside me. But at other times She enjoys dismissing me back to my chores, after all She can & usually does climax later and its often the sweeter and more delicious the later.

I had just finished washing Her discarded silk panties, when Miss arrived. The ones Mistress had pushed into my mouth to muffle my moans and gasps when She pegged me. I always hand wash Her panties after She enjoys sex with me. It’s the one chore She likes to be done immediately after sex. And if She has a boyfriend over She likes to make me wait to iron & perfume Her panties while they are together in Her bedroom.

She always tells me that She takes Her panties off for Her pleasure and I take them off to wash them for Her. 

‘Oh how lovely for you sissy.’ Miss had smiled patting my bottom sharply, making sure to pat the base of my very expanded butt plug.

Being pegged then immediately plugged again, as I always was, made me feel like I needed to pee or was just about to cum for a long time afterwards. And I was never allowed to go to the loo unsupervised and without permission.

Mistress would often need to pee too after pegging me and would often have pee Her hot urine into my open my mouth.

And as a sissy even though pegging made me feel like I was about to cum I was never  ever, ever to be allowed to cum.

‘Yes Miss, thank You Miss.’ I curtsied.

‘Of course if you were my sissy you would be fetching my strap on very often with that cute tight ass of yours sissy.’

‘Yes Miss, thank You Miss.’ I curtsied ‘Especially with that sweet little curtsy sissy.’

Miss was always commenting on how I always smoothed my apron down at the front after I curtsied and always seemed to hesitate when I touched the tiny bulge made by my chastity. She had made me very self conscious about it and didn’t hesitate to mention it and make me squirm for Her and Mistresses amusement.

‘Yes Miss, thank You Miss.’ I curtsied blushing.

‘Or fetching the crop sissy, I do like to see a sissy in terms of pleasure or punishment sissy.’

‘Yes Miss, thank You Miss.’ I curtsied feeling very pale and suddenly weak at the knees at the mention of the crop.

‘And I’m sure you would much rather your Mistress regarded you as subject, or a pretty little object of Her pleasure rather than punishment wouldn’t you sissy ?’

‘Yes Miss, thank You Miss.’ I curtsied squirming with fright as Miss & Mistress smiled enjoying my intense discomfort

‘Put a little more lip gloss on sissy.’

‘Yes Miss, thank You Miss.’ I curtsied hurriedly obeying

‘You do want Sir to think of fellatio as soon as he sees those plush shiny glossy lips, don’t you sissy?’

‘Yes Miss, thank You Miss.’

‘I’m sure he will give you a good hard spanking too sissy when he finds out you’ve just had a lovely pegging.’

‘Yes Miss, thank You Miss.’ I almost whimpered, dreading being put over His knees with my clitty still awfully tight in the chastity cage, as it always was after a pegging and being teased so mercilessly.

‘I know silly sissies always cry and whimper that  they don’t like being spanked, but being put over reals

mans knee and spanked is such a good way of putting you in your place sissy.’

‘Yes Miss, thank You Miss.’

‘Its so delicious  to see a sissy disciplined by a real man.’

‘Yes Miss, thank You Miss.’

‘And so lovely and sweetly effeminine for you sissy.’

‘Yes Miss, thank You Miss.’

‘Such a lovely intimate humiliation for you sissy and you do seem to suck Sirs cock so sweetly afterwards sissy.’ 

‘Yes Miss, thank You Miss.’

I fetched them some more drinks, usually at this point I was dismissed back to my chores but Miss patted my bottom and told me too stay.

Mistress and She discussed male fantasies. Of having a harem or group of pretty girls. And usually they were very pretty sexy bimbos all desperately eager to be chosen to spend some time with their superior and to give pleasure. And knowing that they deserved to be punished if they didn’t please their owner or superior. She described in detail the shiny pretty dresses and how they all ached to serve. And how wonderful it was to have them all to choose from.

Or a harem with all the girls in skimpy glossy diaphanous outfits, with tiny little mouth veils. So that

when they pleased their owner through the veil, as they ached to do and often did.  They would smell and taste His or Hers pleasure on the veil all day after they had been dismissed often to some trivial chore.

But I wasn’t the one who would be choosing. I was a sissy, in a pretty dress, one of those aching to be chosen. Used then dismissed in tears, or worse  impotent feeble envy not to be chosen.

When Mistress went out to Her high powered successful career. In Her expensive plush car. With Her lovely expensive clothes. To Her office where there were lots of handsome men, and women to enjoy flirting with and usually more. And quite a few prospective sissies to tease and push subtly towards  the lifestyle. Or out most nights with Her friends or Her boyfriends.

I would stay at home in my pretty maids dress chastity locked and plugged busy with my chores longing for Mistress to come home, to spend some time with Her.

Busy with my chores and subject to corporal punishment with the horrid canes or the horrible crop if Mistress wasn’t satisfied.

And not only that but Mistress and Her male friends had  a little app. That rated all us sissies. The men would vote and leave comments on the sissies and their performance and how much they enjoyed, um enjoying us. Mistress was always uploading little pictures & videos of me especially in my pink nightie, and giggling at the comments. Mistress would sometimes let me see the pictures and would read me the comments. But I was never allowed to see the other sissies on the app.

One of Mistress favourite videos of me and very popular was one Miss had taken. When Mistress had been away and Miss was looking after me for a couple of days. Miss had brought Sir over and they had told me to get in my pink nightie then Sir had come all over my face. Thick white sticky cum. Miss’s boyfriend does seem to cum  an awful lot. I always nearly choke on his thick load in my mouth, desperately waiting for permission to swallow. And always struggle to swallow. I do on all Mistresses boyfriends and male friends but Miss’s Sir is especially copious. Their cum is so pungent, strong tasting and smelling.

A woman might expect and insist Her boyfriend not to too much beer or coffee if he wants oral sex.

But Men don’t care and shouldn’t care if a sissy find his cum too thick or strong tasting. Nor if sissy was seeming gagging on His cock or choking with Her mouth filled with his thick wad of cum. A good sissy should only be concerned with His pleasure when she is performing fellatio. And Mistresses crop ensured that I was always a very good sissy.   

Miss & Sir  had left me in my cuffs kneeling on my bed, while they had

a drink downstairs. Terrified as I heard Sir and Miss laugh that they should invite their friends over to fuck me. Sir had come back upstairs later on his own and took my panties down and unplugged my bottom for anal sex. And that was a another popular video. I had then been left like that all night locked my cuffs my pink satin nightie and face  sticky & soiled with His cum.

Miss said I was too see the app as a digital harem for the Real Men to choose sissies from. And how wonderful it was to be a superior with apps like that. And how lovely it was for a sissy to wait so expectantly & obediently for Sirs choice.

Miss gleefully informed me that I should be careful with my sexy photos and video’s  that I don’t get any unexpected visitors while Mistress is out.

And after Sir had taken me down to the laundry room and cum deep in my ass I was sent back to my chores.

Mistress would tell me to stop mincing around Sir like such a little bimbo in my sticky knickers and hurry back to my chores. And Sir would slap my bottom firmly sending me off in tears, as i was dismissed.

Even though serving Men wasn’t consensual for me, penetration always left me feeling so emotional & vulnerable, wanting to cling submissively to my superiors.  

Later when Mistress’s guests had left, and I had curtsied and thanked them for coming over & enjoying Mistresses hospitality. I might be sent for my pink cushion again that afternoon or later in the evening. Or simply dismissed back to my chores, while Mistress went out with one of Her boyfriends or friends.

 

    

 

 

 

 

Unexpected visitors

 

Mistress and Miss were relaxing in the lounge, they were sipping chilled wine and waiting for Mistresses boyfriend to arrive. Miss often brought Her boyfriend, or boyfriends  round to enjoy oral and anal while they chatted. In fact She and Mistress had lots of male friends who were invited round so they could enjoy my intimate sissy services. Both Mistress and Miss said it was good foreplay for me as I was always especially needy and attentive after being opened and spread by a real man, and that my licking was absolutely heavenly after I had been put firmly in my place by a real man.

Miss had told me that She often allowed a couple of Her male friends around in the afternoon when She was out at work. Usually no more than 4 as sissy did have her housework to be getting on with. Her sissy would then be so deliciously vulnerable and submissive when She got home that Miss could hardly wait to get Her panties off. Usually though She preferred to savour the moment  and have sissy curtsy and kiss Her bottom but not say very much, then send sissy back to her chores to simmer, for later. After all She could wait a short while for Her orgasm, unlike Her sissy who wasn’t allowed.

Incidentally Mistress, Miss and most of the other dominant ladies never masturbated. They had no need to with sissy on their beck and call. And naturally if they never touched themselves, sissy was not allowed to. Sissies had to be good girls for Mistress and Sir and not touch themselves naughtily. They had lots of trivial domestic chores to be busy with.

The first time Miss had allowed sissy visitors, naturally She hadn’t told sissy beforehand. And the men had left early leaving sissy to be getting on with cleaning the mess they had left and the rest of Her

interrupted chores. When Miss had arrived home sissy was in tears and desperate to tell her owner and Mistress what had happened. But Miss had shushed her and told her to be quiet. Not allowing sissy to tell Her what had happened until nearly bedtime.

Miss had looked at sissy coolly and told Her to fetch the crop. Sissy was given 12 lashes, 6 usually is considered severe with the sissy crop a particularly thick riding crop, often pink or red leather. Mistress had two, one black and one crimson leather, they were both very well worn.

After sissy had been punished She was told what a bimbo, slut she was. And how naughty she was for not telling Her owner about the visit immediately. And that the next time sissy had  a visit she was to be very obedient and submissive to the visitors as it reflected Mistresses hospitality. Sissy was to make sure that all the men were fully satisfied.

Oh and the cunnilingus had been so heavenly She had said indulgently patting my bottom, patronizingly. She and Mistress had exchanged knowing looks. I had squirmed haplessly on my plug. Which made them both laugh and for Mistress to reach for the remote to make the plug even thicker and larger.

Sometimes the men would leave sissy in kneeling & bound in her cuffs and Her face and bottom covered in cum, unable to clean up and continue Her chores. Waiting in fright for Mistress to arrive home and to be sent for the crop. There was no excuse for a messy house.

There were also occasions where one of a Mistresses friends sissy, not my Mistress or Miss, had
received an unexpected visit. This was not considered to be rape as sissy was not allowed to say no. More as a slight breach of etiquette or rudeness on the Mans part. Sissy would be punished by her owner and often by the Man as well. To prevent this from happening again the Man after a bit of a private chat and suitable admonished, He would be allowed to visit the sissy whenever He pleased. Although usually He would get bored of sissy after a short time. And only as long as Mistress approved it, sissy was Her property after all.