“How are you enjoying your little break or vacation sissy ?” He asked
“Though I suppose its been extended somewhat.” He laughed.
At which point sissy had burst into tears and had become quite inconsolable.
One of the Misses had quickly led her away to be punished.
Candi had hurried back from Her very publicly audible beating, as the lounge erupted into laughter and clapping. The punishment-crop, rather than the hurry-crops are very painful, similar in intensity to your Mistresses own house crop. The hurry crops are similar the canes, in between the thicker rod and the springy cane in sting. Any of these disciplinary implements are horrible as intended for the punished. But just the mere mention of the punishment crop, made any sissy numb with fear.
And she had been punished quite severely, but only as much as any naughty maid deserved, when a
superior loses patience with an errant misbehaving chastity-maid. and in between receiving lashes made to recount and apologize for her naughtiness in between further lashes. No matter how much she was our rival, and how much a naughty maid deserved punishment, all of us felt terrible for her none of us would want to be her at this moment. Shamed and in pain the eyes and laughter from the guest all around the dining room as she hurried back to serve.
Her bottom and rump looked raw and inflamed. The unsightly redness quickly went away, but the stinging puffiness wouldn’t for some time. She stood beside me and I could feel the heat from her thighs.
She curtsied to the Mistress. The Mistress who had been his or rather now her former wife, in a previous life, before she had been put in panties and chastity, by her dissatisfied partner.
“Please Miss, this maid wishes to apologize for her naughtiness and disrespectful behaviour Miss, please forgive this maid Miss, thank You Miss.” She curtsied, I could see the tiny but not quite imperceptible wince as she curtsied.
The Mistress
ignored Her for a few moment then looked the chambermaid up and down.
“Yes Miss, thank You Miss.”
“And I trust its kiss hurts you a lot more than it does me,”
“Yes Miss, thank You Miss.”
“But I think its much more important that you apologize to Master, isn’t it candi, I’m sure you cant have forgotten that you need to show respect to your former business partner and I suppose much more importantly from your perspective my chosen lover.”
The Man was a former associate of the sissy, the lawyer at the firm , who had cucked him and assigned all his assets to his wife, when She decided She wanted much more than just a divorce settlement, from the sissy. The Mistress had long since decided She didn’t want sissy around anymore, and transferred sissies service contract (effectively
ownership of sissy as chattel) to another Mistress
“Yes Miss, no of course not Miss, thank You Miss.”
“Well then sissy.”
Candi turned to Master and curtsied.
“Please Master, candi is sorry Master, she was feeling overwhelmed at seeing you again Master, please forgive a naughty silly maid Master, thank You Master.”
He patted Her bottom firmly, making Her wince again, glancing at His crotch I could see Him bulging already.
“I’m sure you can placate me much more satisfyingly with that hot mouth of yours siss…” He looked at the nametag on Her ruffled chambermaid collar “candi, come along little chambermaid.” He said rather impatiently, slapping Her rump again as He hurried Her away to a private room.
She whimpered and curtsied “Yes Master, thank You Master.” Mincing prettily but trying to hurry so as not to incur Him slapping the backs of her thighs to hurry her along, too much a least.
He as well as cucking His former business partner, with the sissies now ex wife,had also been the first Real Man, sissy had, had to suck and the fist Man to spread and penetrate sissy anally.
The Mistress rolled Her eyes as if slightly exasperated and bored, She turned to me.
“More coffee sissy , and bring me that cake trolley, while I’m waiting.” She told me.
“Yes Miss, thank
You
“You are a pretty one in that dress and such a cute little ass too.” I’m sure my boyfriend might want to
have a little time with you later as well. The Ladies and Misses always teased and half flattered us about how sweet and cute we were, and we always fell for it, as if they didn’t say exactly the same thing to all the sissies. After all we all had to stay slim and feminine in that sissy way, lovely for the Sirs and Masters to enjoy.
“Yes Miss, thank You Miss.”
“The other dress might have been prettier though,” She said referring to the dress candi was wearing “Maybe my boyfriend might have picked you instead.” She teased with a little knowing smirk.
The Misses watched us closely in the mornings, as we got dressed. We would be hurrying about putting our make up on and getting dressed. Although all the maids dresses are all slightly different in detail, they are all very lovely and pretty, we get attached to the look of one of the dresses and the Misses take delight in pairing us up. Knowing that
one maid wanted the other dress and deliberately swapping the choice over. This would make us terrible jealous, feeling very small and petty too, the Misses would note this , and make the rivals work and serve together. The close proximity and added humiliation making us strive to please the guests that much more.
The Misses would often enjoy watching the impotent but furious jealousy simmer and nearly boil over into tears, then call us both over and ask us why we were getting our panties in a bunch, or a twist ? And then make us swap panties as telling us that there was no real difference inside those sissy panties is there sissies ?. We would have to kiss the warm crotch as we swapped over. Then make us hold our ankles for a swift criss cross with the hurry crop before sending us on our way.
As well as several other maids, It had been myself and candi this morning, I had been so taken with the pattern of lacy detail on the dress She was now wearing, and She with the organza frill on mine. And of course we had been made to work together all
morning first kneeling and polishing shoes together, then hurrying about taking away smelly sticky sheets in the bedrooms. I had also been a little upset that I wasn’t chosen for the panty laundry today, but there were other new chambermaids who had been chosen for that today.
So even though we always protested about the interruptions in the laundry room, as the guests would come in and push one of us face down in the still smelly pantie pile to be raped, while the other maids carried on working, obediently. I had to admit I was feeling needy now.
Then we had been called over to serve this couple together. I wasn’t sure if they had recognized candi or not at first, or whether it was just a delicious coincidence, for the superiors at least. To the superiors we must seem like a collection of, pretty maids, nameless in the hotel except for the use name assigned to us for convenience. Apparently some hotels used numbers which sounded horrid, plus most maids in advanced stages of treatments & hormones are completely illiterate. Even now when I saw writing or numbers I mostly just saw random patterns, not realizing what it was by
design of the treatments and autosuggestion. Maids must think only about domestic duties and pleasing their superiors, not bothering their pretty heads with things they don’t understand that might upset them, and in any case these matters are for the superiors.
“Yes Miss, thank You Miss.”
“Oh look at you squidging so helplessly, with just a tiny bit of flattery.” She said disdainfully.
“Yes Miss, thank You Miss.” I curtsied smoothing down my apron prettily.
“I’m sure Master might want you to taste Him later too, or He might want to enjoy that little peach of yours, cherri.”
“Yes Miss, thank You Miss.”
As if on cue Master and candi came back from the private room, both looking very flushed, but He
looked very satisfied and she looked very shamed and needy too.
“How was your trip down memory lane dear.” The Mistress asked candi ?
“Yes Miss, it brought back a lot of memories Miss , thank You Miss.” She almost mumbled wistfully. My heart melted for her even though she was wearing my dress.
“And I am feeling rather hungry now, go and fetch me an English breakfast sandwich candi, you know how I like it.” The Master told candi.
She did know exactly how He liked it for years it had been both of theirs mid morning breakfast staple in the office, a thick doughy bread roll with bacon sausages and an egg on top. The sort of food that would have led to a heart attack in the past but now as healthy as fruit and vegetables. Of course He
could still enjoy a breakfast sandwich but housemaids and chambermaids would never be allowed anything like that ever again.
“And you maid is that coffee fresh.” He said turning to me
“Yes Master it is Master, thank You Master.” I whimpered, very glad that I had just swapped the carafe over.
“Well what are you waiting for maid.” He told me patting my bottom firmly “an invitation ?”
“No Master, at once Master thank You Master,” I curtsied and quickly poured the coffee feeling very flustered.
After breakfast, well it was more like brunch by that time, the Mistress announced She was going to enjoy a massage at the spa, before the couple went out for the afternoon. I was quite envious of the maids in the spa. The masseurs for the female guests were not maids but highly paid skilled female masseurs. They did dress in rather nurse like uniforms just for
effect though, and not quite as scandalously short or skimpy as the sissies wore. There some sissy chambermaids in attendance too, but just to assist. And there were also special rooms were the Men could get a much more intimate massage from just the sissies.
“Will you be taking a swim in the pool, or at the beach ?.” She asked Him “Or taking a dip elsewhere ?.” She said arching Her eyebrows over Her sunglasses and looking at us.
He smiled, eliciting another look of amused exasperation, from Her. “Oh never mind I sometimes wonder why I bother asking.” She laughed.
I sometimes wonder
why the dominant Ladies tolerate such behavior from their lovers in this FLR
scene, but I suppose real women enjoy real sex and it is so much better for
them with a nice manly real
In any case She stood up kissed Him on the lips and almost flounced to the spa. After we both curtsied to Her of course and thanked Her for allowing us to serve Her breakfast. Needless to say She didn’t acknowledge our curtsies and thanks.
Turning to us both He patted our bottoms and pointed us towards the private room again.
“Yes Master, thank You Master.” We both curtsied and tottered just ahead of Him, no-one in the room paid us any attention now. We were just a pair of maids going to one of the service rooms.
Inside the room it was stinky and thick you could almost taste the sex and fear. I realized that this was the same room candi had been whipped in earlier, and the same room Master had raped her in after Her corrective beating. We both realized this at the same time rather. And He knew already sitting down on the plush leather armchair, not particularly bothered or affected by the smell
“Pour me a drink candi , you remember my favourite don’t you sissy, then you may face the wall.”
“Yes Master I do Master, thank You Master.”
“Yes Master ‘this maid does Master’, thank You Master.” He corrected her.
“Yes Master, this maid is sorry Master, this maid does remember your favourite drink Master, thank You Master.”
It was a little early for whisky I suppose but it is vacation time, She poured Him a whisky on ice with just a dash of water and brought it to Him on the silver serving tray.
He took the glass “Face the wall, curtsy cuffs sissy.”
“Yes Master, thank You Master.” She obeyed quickly.
There isn’t really much need to instruct us curtsy cuffs, as that is how we must stand in readiness anyway. Standing upright, back straight, head slightly bowed, eyes lowered respectfully below the superiors waistline, and holding the hems of our dress with our fingertips ready to curtsy. But the superiors enjoy imposing the instruction on us anyway.
He patted my bottom and pulled me closer to Him, so I was in His personal space, or rather He was in mine. “And you sissy, did you think I did not notice your little glances and furtive squelching earlier, why were you so excited and distracted sissy.”
“Yes Master, please Master, this maid cannot help it Master she is very needy Master, thank You Master.” I curtsied blushing.
“So you were needy sissy?”
“Yes Master, thank You Master.”
“Like those hot and wet slavegirls in your pathetic little fantasies ?”
“Yes Master, thank You Master.”
“And are their hot needs or your needs of any importance maid ?”
“Yes Master no Master they are not Master, thank You Master.”
“What is important sissymaid?”
“Yes Master, only your pleasure Master, thank You Master.”
It was always a very humiliating realization and one the superiors enjoyed leading you into. No matter how desperate and needy you were, and housemaids and chambermaids, chastity-maids in general were always so emotional & needy, nearly in orgasm during their every day duties let alone in the presence and close proximity of their superiors, your needs were completely unimportant only the superiors pleasure and satisfaction mattered.
You should be desperate to be chosen but never for your own hot desperate need but only for His pleasure.
“Get over my lap sissy, I think you need to be punished before I decide I might enjoy your service or not.”
“Yes Master, thank You Master.”
Over His knee He locked me in the cuffs set easily, He was quite a big strong Man with very large hands.
“I think you deserve to punished no less severely than candi, maybe even more so for bothering me with your little needs.”
“Yes Master, thank You Master.”
“Don’t you agree cherri ?”
“Yes Master, thank You Master.” I sobbed.
“A nice firm spanking, to redden your behind ?”
“Yes Master, thank You Master.”
“Maybe spank some of those needs out of you.” He laughed
“Yes Master, thank You Master.”
“Hand me your panties candi,” He told the other maid.
“Yes Master, thank You Master.” She curtsied and obeyed quickly
“Remain facing the wall, curtsy cuffs.”
“Yes Master, thank You Master.”
He held the panties in front of my mouth under my nose.
“Don’t these warm little satin panties, smell of sex and need sissy too?.”
“Yes Master, thank You Master.”
He stuffed them into my mouth. Although the lubes are actually totally dry, but the silicon just feels incredible wet and slippery, and also rather non smelly. The auto conditioning made the panties to us, made the taste and sensation of wetness was overwhelming.
He spanked me very firmly, with His huge flat palms, until I was sobbing in pain over His lap. Sobbing, blubbering and pleading into the pantie gag desperate for Him to relent. But of course He would not and did not until He was totally satisfied.
When He was finally finished He pulled the panties out of my mouth tossing them to floor next to candi.
“Put them back on, candi and fetch me another drink.”
“Yes Master, thank You Master.”
He pushed me to my knees in front of Him and I kissed His hands
sobbing and thanking Him for disciplining me so I would serve Him more perfectly. He didn’t bother to reply to me. He just took the drink from candi and put Her in cuffs too, pushing Her to Her knees beside me.
He undid His trousers and eased His swollen cock out.
“You may look up and kiss me, together.”
“Yes Master, thank You Master.” We chorused, as He took a sip of His whisky.
He was huge and very erect. All real Men seem so big to sissies, and most enhance themselves to 8” or more He was 10”. Glancing at candi from the excitement and fear in her eyes I could tell He must have always quite naturally well endowed.
We both kissed and sucked on His balls and around His shaft, kissing but not sucking yet on His glans. He seemed to be getting even harder and
more erect with each kiss.
He wanted to tell us, or rather for candi to tell him and me how She had been cucked and put into panties by candi’s Mistress and Him, reduced into total penury as well as becoming a sissymaid, by the lawyer and the former wife. With Him interjecting adding pertinent details.
Like how, one time the former friends had been having a drink together and the former he had confided to the lawyer, that there were problems with the marriage, and how he suspected his wife was having an affair. All the while, the lawyer had been fingering a pair of the wife’s panties in His pocket, listening sympathetically, but disinterested. Laughing about it with the wife later in bed or in His office while they stripped all the assets from him. Or how after the sissy was put in chastity, but still hadn’t realized she was being cuckolded, the sissy asking the wife about cum stains on Her (the wifes) panties as sissy hand washed them. And when the lawyer had finally come home with the wife to the now sweetly feminized sissy, (the hormones worked very rapidly, in the initial stages, days and weeks, rather than months) and sissy had been taught to suck the lawyers cock, and then
penetrated by Him.
I had to also
ask her lots of salacious emotional details and Him lots of respectful questions.
And to imagine myself in her position and embellish the details, so that I felt
her humiliation and shame. And to add details of my own story into chastity
& sissification. Though not quite as abrupt and jarringly disconcerting as
her story, still equally humiliatingly exciting to confess in front of a real
With each detail and confession He seemed to be becoming more impossibly erect and obdurately harder, but in truth He was shifting and squirming in His chair too. And also although it seemed like a bottomless well or labyrinth of questions to us maids it was only a couple of minutes really.
Some Men when they first enter the scene are not so confident or enthusiastic with sissies. There is still a residual trace of reluctance about homoeroticism even though we are kept very feminine, in a sissy way, in our dresses, nightwear & maids uniforms. There is still that slight sense of distaste or revulsion after they have cum. But gradually some Men either leave the scene altogether (some may end
up being sissified if they fall foul of the wrong Mistress) or become totally comfortable with sissies who are much more girly, girly, and totally submissive, awe stricken and fervently so. Much more than any true female ever pretended She was no matter how subjugated She was.
Especially after hormone gelding and the sissy has grown small pert breasts. When that happens the sissies must call all real Men Master and be totally pleasing and obedient, much more so than they ever felt possible before, nearly orgasmic at pleasing Him. And apparently some Men take to I straight away like a duck to water, like candi’s former Sir and Master.
He reached down and pushed my lips over His glans and His cock. Then lowering the top of candi’s dress pressing Her breasts around His shaft, massaging Her cleavage up and down and into my mouth. We were both looking up at Him desperately needy while I bobbed my mouth up and down around the swollen throbbing bulb of His glans. Candi was gasping and telling Him how big and manly He was as I sucked. Then He lowered my dress and switched us around, massaging His cock with my breasts as candi sucked. Before He pulled out Her mouth splashed a hot spurt of precum in both our faces.
“Thank You Master, Yes Master, thank You Master.” We both chorused before He took a fistful of my
hair and pressed His cock firmly into my mouth. I spluttered and gagged choking as He went fully deep into my throat His balls on my chin. Then just as quickly He pulled out and did the same to candi as I gasped. Then me again and this time He felt so very hard and urgent, before He exploded into my mouth filling it with thick cum, and then filled candi’s mouth too, before pulling out and splattering our faces and breasts too. Pushing us back kneeling on our heels, both candi and I were still squelching on our plugs in unison.
It always awes me how much real Men on the scene can cum and so repeatedly, but this time He had filled both our mouths with some to spare. Again though this was also due to the auto conditioning, our faces filled with submissive awe adding to His satisfaction.
“Anther drink candi.” He told Her gruffly unbuckling Her from the cuffs.
He hadn’t given either of us permission to swallow yet so she couldn’t say yes Master, candi just obeying Him with Her mouth full of His pleasure .
“I haven’t quite finished with either of you yet.” He said.
“Mmmff” we still hadn’t been given permission to swallow. He lit a cigarette and sipped His whisky, looking down on us.
His cum was very thick and thick tasting and equally smelly,
“I think little fucktoys look so sweet silenced with my enjoyment, don’t you agree maids.”
We nodded prettily in agreement, He smiled as we bobbed our heads.
“I used to enjoy seeing you squirming in your tiny chastity cage, waiting obediently to swallow and thank me, do you remember.” He told the candi, she bobbed her head, in shame.
“I sometimes think it is rather a pity, those days are all finished now.” He said lifting both our skirts to reveal just the tiny locks where the chastity cage had been before the hormone gelding.
We bobbed our heads
“But it is also much cuter seeing you this way, properly snipped and sissified, especially as it makes you
so much more desperate to give your Masters what you cannot ever have again, nor ever truly deserved.”
We bobbed our heads again.
“Would you like to swallow now and thank me?”
We bobbed our heads choking now on the thick cum as it thickened in our mouth and throat.
“But I have not allowed it yet have I?”
We shook our heads, He took another sip of His whisky, then a deep drag of the cigarette.
“Do you both beg to swallow my cum, like good little chambermaids.”
We bobbed our heads quite desperate now.
“Such pretty bobs reminds of how you bob your heads around my cock, isn’t that fetching.”
We bobbed our heads again.
“Very well you may both swallow.”
It took us 3 sticky gulps each before we could breath properly again and speak.
“Yes Master, thank You for allowing us to please you Master, and to swallow Your thick manly cum, thank You Master.” We said together.
“You may kiss and thank each other.” He told us
While He watched we kissed each other fully on the sticky lips.
“Thank you candi/cherri for pleasing Master, this maid hopes He was pleased with your service as He was with this maids service.” We both said together fervently in between kisses. We were still in the cuffs.
He reached out to the wall at side of His chair and picked up the tawse hanging there, slapping it loudly
on the palm of His hand, We jumped in frights and saw him smiling at the fear in our eyes as we saw what He was now holding. He leaned forward to press the horrid leather blade to our lips to kiss.
“I told you I hadn’t finished yet didn’t I sissies ?”
“Yes Master, thank You Master.” We sobbed kissing the whip very distressed now.
“I think both pretty maids need some corrective discipline, for thinking of their needs and not solely of my pleasure, and for teasing me with those tight little peaches.”
“Yes Master, thank You Master.” We continued kissing the tawse fearfully.
The tawse was so horrible, so fearsome, like Mistresses crop. Just the sight of that flat thick strip of leather, to be wielded by a mans strength, and your whole world seems to stop and stand still, You are totally stricken and numb with fear.
The only thing stopping you from being completely paralyzed with fear is the fear that your punishment will be that much harsher for any slowness or disobedience.
“Both of you get over the bench.” He told us lifting us to our feet. Not giving us a chance to comply He pushed us face down over the leather bench, securing the strap across our waists, as we sobbed in misery. The bench was designed sloped slightly, so that your bottom was held up and ready for punishment or penetration, He stepped behind us and peeled down our panties to gag us with each other satin briefs. Hers seemed soaked with hot damp fetid erotic fear, as mine must seem to Her.
He stepped behind me and gave me six very well timed blows, as I squealed and sobbed into the pantie gag, overcome with fear and pain.
There is no way for a sissy to hold back the blubbering and pleading even before the first blow lands. As you engulfed with fear then pain and misery, knowing waiting for the next inevitable lash.
After 6 He stopped, but told me He wasn’t finished with my ass.
As I waited in terror as candi was beaten next with 6 fearsome lashes. The tawse is nearly as horrible to listen to as was when it hits your own bare flesh.
We were both sobbing in pain now as He opened His trousers. I heard Him remove her plug and place it on the bench besides her head, between our faces. He was very quick and rather urgent. Almost roaring with pleasure as He came, as He withdrew He splattered both her bottom and back, and part of mine.
He stepped behind me again with the tawse, telling me that it was only fair, in His opinion that I should receive some further lashes, after all candi had been cropped by the Misses for her disobedience, whereas I had so far gotten off lightly for my impertinence.
I sobbed into my gag.
Unless you can think of any reasons why you don’t deserve it sissy.
Unable to answer I sobbed into the gag, my pleading and begging completely muffled. Candi looked at me as wild eyed in fright as I must have looked to her.
He gave me another six, then candi another 2, and finally another 2 for me.
Then roughly removing my plug and spreading my cheeks He entered me with a grunt of pleasure. He was very forceful and urgent, but possibly only as much so as He had been with candi, but I had been too engrossed writhing in discomfort and pain to keep track.
Then with another grunt of satisfaction He spurted massively inside me, then lying on my back for a moment before pulling out pulling out and pushed my plug back into place. We could hear Him slapping and jerking His cock about behind is as He sprayed the last bit of cum on our upturned bottoms. The hot spray doing nothing to cool the welt like sensations from the tawse, if anything making it feel hotter and stickier.
The door opened and although we couldn’t see who it was we knew it was the Mistress.
“Oh there you are, have you almost finished, catching up ?.” She sounded impatient but amused.
“I think I might be.” He said quite relaxed.
“Well do hurry up dear, and have a quick shower, you are all sticky from these slutty maids, I have
booked us a table at the seafront restaurant in the village.”
“Coming dearest.” He told Her.
Not bothering to push us down from the bench so we could lick Him clean He just wiped His sticky cock on the back of my dress and the apron, then slapped both of our bottoms causing us to squeal in pain into our pantie gags.
“Goodbye girls and don’t worry I’ll be sure to leave a good tip for the memories and for the service.” He laughed.
We heard the door partially close behind Him.
A short time later when one of the Misses came with another maid to uncuff us, I think She was a little surprised and amused by the state we were in.
“Oh dear, you are both in little bit of a state.” She said as we gave each other a quick douche. She also gave us a little extra time to clean and tidy our uniforms, fix our hair makeup, before cleaning up the service room. As she sat on the armchair smoking, not particularly watching us too closely while we preened and fussed.
When the room and we were spotless again She took us out into one of the hallways and set us both
busily cleaning for a short while. I think I saw or heard the Mistress and lawyer leaving at the other end of the grand hallway, but didn’t dare glance for too long.
It wasn’t long before we were called into the main lounge as there were plenty of guests this afternoon.
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