5. More conversations with Sir/Master, on His Lap

 

“Please Sir, may sissy ask You a question please Sir, thank You Sir.”

“Yes you may sissy and you may call me Master, while I am in charge of you sissy.”

“Yes Master, thank You Master.” I gushed

Calling Sir, Master was an even bigger confirmation of my total inferiority to Him both in status and sexually. It somehow made me squelch on my dildo and feel even tinier in my chastity.

He smiled “Eyes down sissy, unless I allow you to raise them.”

“Yes Master, thank You Master.” My eyes were already lowered but He enjoyed admonishing me, feeling me tremble with obedient fright on His lap.

I had served Him breakfast, and waited on Him obediently. I loved serving Him breakfast, it made me

feel so effeminate and such a  50’s wife. In Miss’s house He would often have 3 or even all Miss’s sissies waiting on Him & serving Him breakfast. The sissy who had woken Him with fellatio would be left facing the wall though until after He had finished His breakfast and then He would permit her to swallow. She might receive a squeeze or slap on her bottom as a little reward before He sent her and the other maids back to their chores. Often it was me who woke Him when I stayed over. Apart from the hotels where I was boarded, as a chambermaid  when Mistress went on longer vacations, Miss’s house was the only place I was  allowed to go to, taken to rather outside of Mistresses house.

Sometimes He might find reason to put one of us over His knee for a spanking or much worse bent over for the crop. If His coffee was not just a He wanted it, or His toast cut wrong. While the other maids all carried on with their duties, glad that it was not them over His knee. But also desperately wishing that it was them. Even the crop we so desperately ached for His attention, His domination.

He was very strict, we were punished with the crop for the slightest of reasons His crop was very well worn, just to see it with the leather smoothed and shiny with use, made my knees go weak with dreadful fright. Miss too, and She was always encouraging Mistress to be stricter with me. Mistress preferred Her canes mostly. The thick rigid one firs then to follow up with the springy thin cane. These were dreadful too, especially as Mistress enjoyed knowing exactly how to punish me, it was so intimate and painful . But the crop in Mistresses hand was much, much more it was so terrifying and dreadful. For anyone apart from hormone and estrogen soaked sissies, they could get used to pain, build up a tolerance even defiance. For sissies it was the opposite, each time we were punished or were sent to wait terrified anticipating punishment it felt immeasurably worse than the last time. Even for a spanking, let alone the cane or crop.    

And it was so horrid and upsetting to watch another maid being

punished. Watching her bent over in cuffs and gagged, squealing and sobbing with each blow. Struggling helplessly, writhing in pain and fear but easily held down. She deserved to be punished, you wanted her to be punished, she was a disobedient minx, a slutty teasing bimbo always seeking attention, who deserved to punished. You were glad it was she and not you, but it could easily be you next. And you had to continue with your chores as the maid was punished as if nothing extraordinary was happening. Trying not to glance around at her muffled cries of misery. You felt so powerless and feeble. So small and tiny in your chastity, in your glossy satin panties, so effeminate. How could you have ever thought of yourself as a man to be so utterly dominated and sexually humiliated. But so thrilled and shamefully excited too.

Just as in the hotels where Mistress sent us to work as chambermaids when She went on vacation at the

sexual beck and call of the male guests. Seeing one of the maids raped over a pile of lingerie in the laundry room while you and the other chambermaids continued working in flustered breathless silence. Or seeing one of the maids hooded and taken to one of the rooms for a group of Men to enjoy. Or being that maid yourself in the darkness of the hood, not knowing who or how many would be fucking you, or face down in the pile of laundry.

You were so glad it was she and not you, but so thrilled and envious that it could be you next.    

Then after His breakfast He would often want another BJ before setting off for work. Sir, or Master, I blushed hotly even thinking of calling Him Master, was quite insatiable sometimes. The lucky sissy would kneel on the kitchen floor while the other maids carried on with their chores. Sometimes though He would allow each of His to kiss His still erect still cocky cock after He had cum, before the lucky sissy finally sucked Him clean and dried Him. Just sometimes though, often we just worked in envious silence.

We would all be a flutter after He had lefty for the day, but working in silence so as not to disturb Miss who liked to wake later. Sometimes the sissy who woke Miss got to please Her in the morning, but not very often, both Mistress and Miss were not interested in the morning. But just sometimes the ecstatic sissy would be pulled under the hem of Misses nightie, or queened using the pillows as a makeshift queening seat. This was never me incidentally I was intimately exclusive for Mistress. We would all be dreadfully jealous of sissies with Her still damp face. All of us trying to linger close to the lucky sissy so we could smell the superiors scent still on the maids face and hair.

Mistress if She wanted it preferred to queen me in the mornings while She enjoyed Her first coffee and

smoke. But sometimes on very special days it was under the silk sheets and hem of Her damp lingerie, while She wrapped Her legs around my head.

I had served Him breakfast in Mistresses kitchen then He had sat me on His lap to swallow obediently and gratefully.

“Please Master, did I please You last night Master.”

He patted my bottom and I took this as my cue to squelch on my dildo for Him.

“Yes sissy you were an enjoyable little fucktoy.”

“Yes Master, thank You Master.” I squirmed happily

“Just like all the other fucktoy maids.”

“Ohh Yes Master, thank You Master.” I replied my eyes welling

“Please Master may I also ask if I pleased You this morning Master ?, thank You Master.”

“What a needy little bimbo you are sissy, but yes your mouth was very enjoyable this morning.”

“Yes Master, please Master may I say I love pleasing You with my mouth Master. thank You Master.”

“You are all always very obedient and enjoyable, after a good hard spanking.”

“Yes Master, thank You Master.”

“And if you are not pleasing you will bent over for the crop wont you sissy?”

“Yes Master, thank You Master.”

“And you will deserve the crop, if you are not pleasing wont you sissy.”

“Yes Master, thank You Master.”

“And you will thank me after the crop wont you sissy.”

“Yes Master, thank You Master.”

“So soppy and desperate to please me in each and every tiny way.” 

 “Yes Master, thank You Master.”

“And especially so at your special time of the month sissy.”

“Yes Master, thank You Master.”

“I do enjoy the time of the month at Odette’s (Miss’s) house.”

“Yes Master, thank You Master.”

I squirmed imagining how pleasurable it would be for Miss & Master to have 5 maids so desperate to please them. And how wonderful it was, when I had stayed over at these times to be chosen by Master, or even I must admit to not be chosen and to squirm in helpless humiliated jealously. When I stayed over and it was Miss’s time of the month somehow I was in sync with the other sissies. Mistress would often arrange for me to stay over for a night or two so She could enjoy my hot eager tongue when She had me collected and brought home.

“Your Mistress also made a good choice denying your pee pee sissy.” He said squeezing my bottom.

“Yes Master, thank You Master.”

“It always does make you so deliciously squirmy.”

“Yes Master, thank You Master.”

“And what is more important your discomfort or my pleasure sissy ?” He asked squeezing my bottom,

He had still not allowed me to toilet I would have to wait till Mistress came home later. And my plug was still at maximum length and girth.

“Yes Master, Your pleasure always Master, thank You Master.”

“Good girl He said squeezing my bottom again.”

He and Miss, and the other superiors, Mistress too often enjoyed leaving us waiting till the very last minute when we were expected to be allowed to pee, and then to cancel our toileting for one reason or another. And smiling watching us curtsy and thank them for being so strict with us. It was a pleasant little game for them, denying us little things, in their eyes, things we so desperately wanted or had been looking forward to. Then watching us curtsy just about holding back the tears and curtsy thanking them. Watching us hurry back to our chores often with soft tiny fists clenched in helpless powerless fury.

And the intensely humiliated shame of knowing that when we curtsied, on the verge of  bursting into tears we were truly thankful to be so strictly controlled and well dominated.

He took a sip of His coffee and fondled my bottom.

“And sissy tell me truly if you were given the choice right now, the choice of a little sissy squirt or splash rather, that you sissies all long and hope for, or to never be allowed ever again, but instead to give your Mistress a perfect orgasm. Multiple climaxes of course sissy. Or to look up at me your soft glossy lips around my cock to give me perfect fellatio, and filling your mouth and your face with my pleasure. Which would you choose sissy?”

I squirmed on His lap

“Yes Master, thank You Master….”

“Remember sissy think back to a time when you last thought you were to be allowed to cum, How desperately hot and needy you were sissy.”

“Yes Master, thank You Master….”

“Or even just to be milked, how needy you always are, imagine being allowed to,  just once or  maybe

occasionally. Or instead  to give me or your Mistress a perfect orgasm. A one time forever decision sissy, which would you choose sissy ?.”

“Please Master, sissy would choose to give her Mistress a perfect orgasm or You perfect fellatio Master, thank You Master.” I looked up emotionally tears welling in my eyes.

He smiled then said “Eyes lowered sissy.”

“Yes Master, thank You Master.”

Several times He had asked this before as had Mistress, I remember the last time kneeling with the other sissies in Miss’s house and answering the very same answer in hot emotional shame, so needy. The other sissies looking down or away flushed with the same hot shame. Then He would choose on of us for His BJ.

“This is why you will always be kept locked in chastity sissy, not just because you of course deserve to be, but because it keeps you so lovely, pliant and obedient for my and your superiors pleasure sissy.”

“Yes Master, thank You Master.”

“And nonetheless, the choice is not yours and never will it be your choice sissy.”

“Yes Master, thank You Master.”

“You will always strive and ache to give me a perfect BJ, and each and every time longing for it to be the best I’ve ever had yet wont it sissy?”

“Yes Master, thank You Master.”

“And you will always do your utmost to perform your chores and housework, faultlessly wont you sissy, both your domestic and intimate service, devotedly and lovingly to perfection.”

“Yes Master, thank You Master.”

“And strive to be always be seen to be doing so wont you sissy.”

“Yes Master, thank You Master.”

“Or be punished as you deserve and know you deserve to be sissy.” He patted my well squeezed and fondled bottom firmly.

“Yes Master, thank You Master.”

“You will want to be punished if you are not pleasing wont you sissy.”

“Yes Master, thank You Master.”

“And be thrilled to be kept under a perfect and strict discipline, so you are always a good maid.”

“Yes Master, thank You Master.”

“Even though the crop and the canes are so fearful and painful.”

“Yes Master, and Your palm too Master thank You Master.”

He laughed “Yes of course sissy but that is so intimate and enjoyable, isn’t it sissy.”

“Yes Master, thank You Master.”

“For me at least sissy.”

“Yes Master, thank You Master.” I must confess I did love to be spanked for the first one or two at least, but Master and the Sirs knew that, which is why they always spanked so hard till we were in tears, squirming in distress over their laps desperate for them to stop. The paddle was very painful too, like a spanking but much wider and harder.

He was hard in His trousers now, and I was breathing heavily as I slipped just a little closer to Him, on

His lap. He groaned ever so slightly and I was so pleased, to be exactly where I deserved to be.

“Thank You Master.” I whispered

“What for sissy?”

“Yes Master, for being so strict, and…firm with sissy, thank You Master.” He patted my bottom again as I wiggled softly against His erection.

“One day all of Odette’s sissies will have sweet little breasts, would you like sweet little breasts for me sissy?”

“Oh Yes Master, thank You Master.”

“I think double D’s would be a nice size for you sissy.”

“Yes Master, thank You Master.” That didn’t sound so small to me

“A nice bouncy cleavage as I look down at you, jiggling for my pleasure.”

“Yes Master, thank You Master.”

“With nipple bells, or a belled chain.”

“Yes Master, thank You Master.”

“Or to cum all over too sissy, as well as blowing in your face.”

“Yes Master, thank You Master.”

“Of course that would mean you might never see your tiny little thing again sissy.”

“Yes Master, thank You Master.”

“But we will probably have had you branded and fully snipped by then sissy.”

“Oohh …Yes Master, thank You Master.” I looked up distressed, then quickly down again frightened.

Miss has often discussed with Mistress that eventually She will have Her sissies totally and fully

effeminized, with natural breasts and gelded, maybe with just a tiny nub left, that can still be kept locked up just for the pleasure of keeping us locked even though it will be fully and permanently flaccid. or it might pushed and held  inside us, in little labial fold, maybe also belled. Then She might finally gift or trade Her sissies to Sir, or Master, for His household. Then She can start the process over again enjoying the chase, process and teasing, feminizing new sissies for Her pleasure. Or She might decide to have  a normal family life and just to enjoy sissies in the clubs if She so desires. Mistress has said too She might consider gifting me to either Miss, or to Sir, eventually but not for a long time.

I imagined myself in Master house, all His maids kneeling with our branded bottoms trembling  in the air, waiting fearfully to see if He would punish us, or jiggling our breasts for Him hoping to be chosen for His pleasure. During the day we would wear standard black and white latex maids uniforms. But in the evenings maybe a selection of pastel pink uniforms and for His bed latex pink babydoll outfits and bedwear. Master might choose to share us with His male friends, but I suspect He would keep us for himself exclusively so we constantly ached and competed jealously for His sexual attention. Of course if Miss visited Her sissies might be allowed to please Her if She so wished, and if Mistress visited She might enjoy my tongue or pegging me. And of course that would be as frequently as She desired. For the rest of the time I would be for Masters pleasure when He selected me.

He had my key as well the key to all Misses sissies. He also had the keys to other sissies belonging to other Ladies too, who He regularly enjoyed and especially so at their special time. He was exclusive for Miss though, She would stand for anything otherwise. Mistress had several boyfriends and dalliances, though not usually at the same time, though She might sometimes enjoy a new guy in the office if He looked hot. They always had a copy of my key, just so they knew I was kept locked and to remind me of my place when they were with Mistress. But when Mistress and they parted ways the keys were handed back. Mistress has said eventually She will find a nice long term Man. And I would either be a maid for them, or not, as She and He chose.     

“But don’t worry about your tiny thing sissy, without it you will still be able to please me perfectly with your hot soft lips and that tight squirmy ass

sissy.”

“And all that will matter will be pleasing me wont it sissy ?”

“Yes Master, thank You Master.”

“Just as it is now sissy.”

“Yes Master, thank You Master.”

And as I had been told gelded sissies still ache, even more so to cum and are evermore attentive and

obedient because of it.

He smiled and told me to lie across His lap now, to be spanked.

“Yes Master, thank You Master.”

After my hard spanking He pushed me between His knees, He was so hard when I opened His trousers and He came powerfully almost as soon as I had deep throated Him. He was always so big to me and I always gagged and spluttered choking on all real Men but especially Him. He always came so massively and thickly too. In the morning after His coffees and cigarettes the taste and smell was so overwhelmingly strong. Some Men enjoyed the fact that we found the taste and smell of their strong cum overwhelmingly unpleasant and distressing, and some simply didn’t care. Master usually  didn’t care and I loved that He didn’t care. Why should He be concerned about my discomfort, I was there to serve and please Him. Of course He should enjoy a beer or coffee, a cigarette and I could enjoy the strong taste of His cum. Just as Mistresses pee is very strong tasting in the morning or after She has been enjoying wine. I looked up at Him adoringly, as always in awe of His powerful male pleasure & domination. He allowed me to swallow then told me to polish & buff His work shoes with my satin panties while He had another coffee and cigarette.

He always told me that this was a perfect way for a sissy to start her day. It didn’t matter that I had been awake since the very early hours in my uniform cleaning, polishing and preparing so that everything would be perfect for when He woke. A sissies day starts when their significant & superior other wakes. He would be going to work and I would be starting my chores again. He had cum and I was still so desperately needy and so nearly orgasmic, and would be all day.

Mistress loved to send me to start hand washing Her panties after Her orgasm had subsided. She especially enjoyed it when She came home with Her panties soiled from sex with one of Her lovers, giving them to me crumpled dismissively to wash. Knowing that I had hand washed each and every pair lovingly, curtsying and kissing each pair, ironing and scenting, folding them adoringly. And She or Her lover would just peel them off and toss them to the floor. Sometimes She came to watch and tease me as I washed them. I hated and loved that She simply dismissed me after oral sex, made me so long to kneel for Her again. Or sometimes She would come home and I would be sent for the strap on to be pegged. Then after She had cum simply be told to get on with my chores. Or for one of the Sirs after He has fucked me, slapping my bottom and dismissing me in tears. Master though often liked to have me polish His shoes with my panties, before dismissing me.

I was squirming so hotly on my knees now, knowing that my arousal wouldn’t subside all day. Rather it

would build and build until I felt like I would almost burst. I would be squelching and squirming in my chastity on my plug, in my satin panties as I hurried about all my housework. Knowing that when He went to Miss’s house later and chose one of Her sissies to serve Him I would still be busy with my chores. And I would be totally and hotly  jealous of that moment, as would all the other sissies who were not chosen. And so totally wish that it had been me on my knees all last night in the horrible humbler, waiting, squirming in erotically charged fear and pain , just so I could please Him at this time.  And I would ache and fantasize about that moment all day squirming and throbbing on my plug, busy with housework locked in chastity.

“Wont that be enjoyable for me sissy?”

“Yes Master, thank You Master.”

“And so lovely for her too, looking up at me, as she sucks me so sweetly and lovingly anxious to please me.”

“Yes Master, thank You Master.” I was blushing furiously now, nearly in tears of helpless arousal.

“And then swallowing my thick pleasure.”

“Yes Master, thank You Master.”

My mouth and face was still thickly sticky with His cum.

“Eyes down sissy and continue polishing my shoes.”

“Yes Master, thank You Master.”

When He had finished His coffee He allowed me to clean my face and uniform with my panties before

putting them back on.

He slapped my bottom. “Enjoy your day and your little chores sissy.”

“Yes Master, thank You Master.”

But then He had humiliated me again in front of the vanilla repair Man. Mistress mainly tries to employ workers from within the scene, or who are sympathetic to the scene. But there is often some need that cant be fulfilled.

At first the repair guy hadn’t realized I was  a sissy, but when He did and He saw the blob of cum He had smirked and looked at me with a mixture if disdain but also lust. Sissy prostitutes are quite popular for stag, hen  and other party nights. Female prostitution is considered to be too demeaning. And an owned effeminized sissy is very eager to please with her mouth and bending over, or be punished by her owner. Nonetheless it was the first time, I think He had come across  a sissy housemaid, and at first He was uncomfortable which made me very embarrassed standing there eyes lowered while Master & He chatted,  until He started smirking and then I was even more embarrassed.

Master had sent me into the lounge to wait for the crop. And after 12 lashes I had sobbed on all fours kissing the leather tab of the whip. Kissing the hard leather, in pain and fear. Covering the leather in sobbing kisses, pathetically grateful that He had stopped and terrified He might decide to punish me some more. The leather was slick with my sweat and fright, pungent with the strong taste and smell. Of sex and fear. And also I so shamefully wanting to suck Master again to please Him to thank and placate Him.

It was Mistresses crop, He didn’t bring His own, He saw no need to. Even that had felt like a violation at first. Mistress only occasionally allowed Her boyfriends to punish me with something other than a spanking or the paddle. Occasionally a long term boyfriend could use a thicker rod like cane to discipline me. But never the thick and thin set She reserved for Herself, that was far too intimate between us. Like Her crop, but She allowed Him to use it. Telling me not to be so silly. It was newer than His and Miss’s crop, the crack of leather was louder and snappier, somehow different more terrifying and at the same time equally awful.  

Sobbing on all fours I had glanced around and saw the repair guy looking and watching through the

window. Master had noticed too but wasn’t particularly concerned. In fact I suspected He had deliberately left the blind open so the repair guy could see. And the window open so He could hear too.

The repair guy was again watching as I curtsied to Master at the door, saying goodbye. Please Master my eyes were brimming with tears silently begging Him to stay so I could fellate Him again or He could spread my legs and fuck me. The amused twinkle in His eyes said He knew exactly how I was feeling, and He was pleased. In fact He was even thinking about it but He had to go to work.

And all day now I was conscious of the repair guys stares at my reddened bottom and legs. All day while my rump throbbing and smarting terribly. My rear inner thighs throbbing terribly every time I moved causing my inflamed puffy flesh to rub together. And then the next day when He had to come back and I was left cock gagged by Mistress. The clearly exaggerated pursed lips embossed on the gag inviting fellatio. The delivery Ladies had seen it all before of course but it hadn’t stopped them laughing and commenting with the repair guy. And calling on me to fetch them coffee while they took a break. I had to curtsy and serve them perfectly, still cock gagged.

But then later that first day when Mistress had come home and I had so wanted to be with Her to kneel between Her thighs and serve Her, or just to attend Her and bring Her drinks. And I think She had quite clearly wanted kneeling for Her intimate pleasure too but was enjoying watching me squirm then sending me back to my chores, that much more. After all She could enjoy my tongue whenever She pleased.

She had at least allowed me to pee later that evening before my shower and enema.

But then rather than putting me to Her intimate pleasure, She had wanted penetrative sex and had invited Her boyfriend over, for the night. She had cropped me in front of Him. Then I had knelt between His open knees to suck Him. Fluffing Him making Him cum quickly, so that initially relieved He would last longer for Mistress in bed. He was rock hard after watching my cropping. I often would suck Mistresses boyfriends before they went upstairs or before they went out, so He and Mistress could enjoy their night out and He wouldn’t be too horny until later. Mistress knew how to manage Her boyfriends as well as She knew how to manage Her sissies. But of course real Men got to cum.

I had listened to them upstairs through the open bedroom door as I lovingly ironed a pile of  Mistresses

freshly washed panties. Then breathlessly hurried to fetch them drinks whenever Mistress rang the maids bell for service. And to change the sheets  and or Mistresses lingerie. Licking them clean between sex, then hurrying back to my ironing, blushing furiously. I could see Sir, Mistresses boyfriend watching me watching my bottom as went about my chores and curtsying. I knew He would most likely want to fuck me later, when Mistress was asleep. I had clenched my bottom on my plug vulnerable and frightened which made me squelch and squidge even more, visibly so for His enjoyment too.

While I continued the ironing I was thinking about Master and one of maids in Miss’s house of His sticky fellatio.

But much more longing to serve Mistress with  loving adoring cunnilingus. Hearing Her climax and orgasm with sexual bliss as I squirmed on my plug helpless in near but denied ecstasy, loving Her totally. Listening to them having sex as I carefully and devotedly  ironed Her panties I so wanted to kneel intimately for Mistress always and forever, I  so loved Her and I was so glad to be Hers.