Kiss

Kiss
To kiss softly, obediently adoringly, aching and longing to please Her

Sunday, 27 October 2024

Paid For His pleasure

 


The girl in the black wet look latex micro mini, tottered over to where her pimp was sat with His friends drinking and joking around. Tottering anxiously over on her pink patent leather 6” platform booties, she was wearing a matching pink patent PVC biker jacket, as tight and tiny as the rest of her outfit. She looked very pretty and also very frightened. The short 10” chain, heart shaped links with tiny and bells between Her ankles that made her totter even more precariously on her heels didn’t help. Nor did the sticky feeling, in her panties around her bottom and thighs, even though she had cleaned herself thoroughly. And had swallowed all the customers  cum and wiped her sticky breasts and face clean for the next customer. She still hurried anxiously to the pimp to hand over the money, well deliver the money as  it was always stuffed into her cleavage or the back of her panties, she wasn’t allowed to touch the money, it belonged to her owner.   

She was choking with fright and she was hot and damp between her legs with fear, she didn’t dare keep Him waiting though.

He stomped his foot on the middle of the short chain keeping her in place, as she bent over at the waist


to report back to him. Casually he took the wad of cash from her cleavage and counted it. He never looked pleased with the amount no matter how much or how many extra tips she earned.

trembling with fright she told Him that her last client, although he had asked and only paid for fellatio, had bend her over and forced her for anal as well, without paying extra. She didn’t want to tell Him knowing He would be angry and punish her, but she was too terrified of the consequences of not telling Him. He would always find out.  


The pimp demanded to know why she had not called out to protest. The girl in tears told the pimp that the punter had gagged her with her panties. The pimp had shouted something at the girl, then yanked Her over His lap and lashed her bottom quite savagely with a short riding crop.

The loud vicious snap of the leather and her fearful squeals of pain and misery, served to incentivise the other whores all lined up on the display stage, equally luridly dressed, each holding a circular  number card so the punters could choose them easily, gyrated and squirmed suggestively. All were evidently frightened and glad it wasn’t them this time, making sure they continued smiling prettily, or pouted suggestively  as they wiggled for the passing clients.

Angrily he told the unfortunate girl to face the wall, then got up and went to where the last client was


still standing laughing with His friends. The pimp was a big intimidating man even to the male clients. Heated but not unfriendly  words were exchanged and the punter handed over a wad of cash, double the rate for anal, with extra tips for the inconvenience. It was  a common game the clients liked to play and only the whore got punished in the end. After the money was exchanged both me laughed, she was only a whore and it was only a slight misunderstanding.

The pimp sat back down and told the girl to go and fetch Him a drink. The last client had paid for the drink and it was waiting at the bar. He could have easily have collected it as he passed the bar, but why should he when she could fetch it. Tearfully she hurried to the bar, past the last client and his laughing jeering friends. Her ass wiggling in the very short latex mini skirt. The clients would often stay in the bars afterwards, maybe one of their friends would the next client. It made the girls feel at the same time very used and  vulnerable. Often the pimp would move us along to one or other of the bars, several over the course of the evening and night, and we would see the same Men, still enjoying their nights out.


She curtsied as He took the drink and told her to get Her ass  back on the stage, with the other worthless sluts. As she hurried away He lashed the back of her legs twice in a casual criss crossing motion with the crop. She had squealed loudly, the Men sitting at the table with the pimp didn’t bat an eyelid. Some of the clients had laughed and cat called, rudely though  including Her last client.

In tears but smiling as prettily as she could She stood next to the other girl. The visible welting of stripes at the back of her legs were already fading. The crop was designed to sting and smart terribly not to mark. So the now there was just a crimson to pink flush on the backs of Her legs, that looked like sexual heat but fuller.

She squirmed and wiggled her perky D cup breasts as prettily and buxomly as she could on the stage, along  with the other girls. Squelching on her massive butt plug, as she tried to attract another client. Hoping desperately like all the other girls to appease and please her pimp.

There was an affected breathy giggle, from the lineup  as one of the other girls was chosen and led away


by her punter. Seeing one girl chosen made all the other whores desperate to be chosen next, knowing the pimp would be watching them, expecting to earn a nice thick wad of cash from each of their asses, or else.

As well as wiggling prettily for the clients, each girl watched the pimp intently, fearfully, for any signs of His displeasure, gasping and choking with fear if He looked, or if the imagined He looked  irritated or angry.

It made them squelch even prettier, and squirm helplessly in their tiny chastity tubes  for the punters.

But how did we get here.

One day a long time ago my wife had caught me masturbating into a pair of silk panties. They weren’t Hers but they were very similar to the expensive pairs She liked to wear. I confessed that I did love the feel of them. I had always kept myself very manscaped and occasionally went a little too far and if I did I loved the feel of my smooth balls and cock in the glossy silk. I also shamefully confessed that I liked to fantasize about wearing sexy clothes with very slinky underwear and being with Her, like a lesbian lover but with extra enjoyment.


But it wasn’t that, nor was it when Her best friend, who had  a reputation for seducing Her friends husbands and boyfriends and informing the cheated on partner afterwards. When She had tried to seduce me unsuccessfully, it was pretty hard She was and is very hot. When I spurned Her advances She had told my wife that I had tried it on with Her. My wife hadn’t believed Her but in that odd irrational way that  women can be, She was still jealous and acted with me as if She did.

Although I had never ever actually cheated, in my head I often imagined myself capable of casual promiscuity. Like many boys I had a roving eye occasionally.

Nor was it the fact that even though I constantly told Her I fantasized about oral sex, but rarely ever went down on Her myself. So in return She never did on me, and even when She had once or twice when we were much younger and new to our relationship, She had never swallowed and made it clear this was a rare treat when I had been very good to Her. Or when I told Her I  fantasized about anal, She had laughed quite scornfully, I had felt at the time. She had told


me that I was rather too under endowed to satisfy Her normally and far too small for anything else, especially anal.   

Nor was it when I lost my rather poorly paid and boring job, when  She realized She could make more, much more in tax breaks,  by keeping me as a house husband. The legislation designed to encourage stay at home moms was not designed for house husbands but to treat me otherwise would be discrimination. The tax breaks were very generous on Her salary, She was vastly more successful and highly paid than I was and ever would be .

Nor was it that She had caught me masturbating while She was out at work and the house was still a mess, I was never very good at housework, until things changed.


But I think rather it was a combination off all these things, so I had been told in no uncertain terms it was a choice. She was going to lock me in a chastity device or I could get out forever.

I had no money of my own & nowhere else to go. I was a single child & my dad had left me and my mum when I was little & I had no idea even if He was still alive. My mum had died when I was in college and I had no contact with any other members of my extended family if I had any still left.   Tax breaks were very generous, benefits were virtually non existent & I would most likely end up on the streets.

So I had reluctantly agreed to Her terms and She had taken the key with Her whenever She went out. I was allowed to be unlocked only when She wanted sex, and only if all the housework was done. I was very humiliated when She told me Her best friend had a spare key too, but had no intention of unlocking it and attempting to seduce me again. Especially when She found out how tiny the device actually was my wife and She had laughed.  

Increasingly my wife had started to demand oral sex when She was horny but I hadn’t been good


enough to be unlocked. And increasingly that became our default option for sex. She had started to insist that I wear panties with my chastity device, but pretty satin panties rather than the expensive silk and lace She chose to wear. Then She had insisted I always keep myself clean and smooth all over. With Veet and waxing  at first for some areas, then later as it developed She insisted on more thorough waxing and electrolysis treatment.


Then it was a full set of underwear and stockings, next a selection of summer dresses to wear around the house. My old male clothes were kept under lock and key now. If I wanted to go out I would have to ask permission to wear them, and I never went anywhere anyway She never gave me any money to go out with. She on the other hand was out quite a lot with Her best friend, so She said and sometimes all night.

Next She came home with a little satin French maids outfit for me to wear with apron and headpiece. The comfortable slip like summer dresses were gone now the way of my boy clothes. Like my new uniform everything around the house now had to be kept neat and perfectly tidy.

Normal sex had long been discontinued, and I was kept permanently locked but as I got more frustrated, She got more horny and demanded oral sex ever more frequently. Though curiously She was never very horny after She had been out on an all nighter.  

One day the washing machine stopped working, I later found She had sabotaged it,  and my wife rather


than getting it fixed had it taken away and an old fashioned manual washer and wringer was brought in as a replacement. This should keep you busy while I’m at work all day I was told. Furthermore all Her lingerie and panties were to be hand washed individually they were too delicate for the old fashioned washer. Over the next couple of weeks all the labour saving devices were gradually replaced, with manual devices. The press replaced with an old fashioned iron & ironing board. The vacuum and floor washer replaced by brush and mop, the dishwasher replaced by me.

At the same time my uniforms became even glossier and frillier and I was expected to keep them and the house spotlessly clean. Any complaints were met with, if you don’t like it you can walk away, and already I felt like we were far to far down this road to walk away.


Then She really got serious. In was told as a special treat after weeks of pleading and complaining that I had been good enough for  a release. I was overjoyed,  that is until She lubed up a latex glove and milked me, while I was still in the chastity cage. So all I felt was the dribble, and leaking feeling, no release  or even a hint of an orgasmic spasm. Never mind She had told me, don’t be disappointed at least you can still give me a lovely orgasm. And so I did She had a very powerful multi orgasm before we curled up in bed. The next time She brought home strap on and pegged me, until She had climaxed and I had finished dribbling. I had been so frustrated but also felt so loving and submissive after that first pegging. Then She announced that I was to wear, or rather be penetrated with a butt plug at all times. Weekly the plug got larger and my chastity cages were getting increasingly smaller. She also got very adept at pegging me until She could orgasm but without allowing me to even dribble unless She wanted to actually milk me.  Sometimes there would be a tiny weak splash of what appeared to be  precum in my panties after a pegging or after I had licked Her to climax. She would laugh at that and make me wear the soiled panties for the rest of day, or sometimes lick them clean and then wear them.

Whenever I performed oral sex now She expected a very long slow licking and multiple orgasms, or


else I was just not worth bothering with. It was just as I had fantasized but it wasn’t. Myself  & Her dressed in sexy lingerie, lots of sapphic sex, and lots of oral and penetration, but it was me always performing oral and She always penetrating me. And I  was never allowed to finish, never cumming. Even now when She milked me recently, I was dribbling less and less and the liquid was even more watery and weak. The newest chastity devices with the urethral insert also prevented me from the pleasant gush experienced when peeing. Wearing the tiny chastity device meant that I  always had to sit down to pee, or make  a mess everywhere, the urethral tube meant that I  always had to sit down and rather than the pleasant sense of release and relief all I felt was a leaking sensation until it was finished. She also insisted that I  have an enema every night to keep my  bottom clean for the strap on.      


I was expected to keep my whole body smooth with electrolysis IPL and waxed in places too, but increasingly there was nothing to wax. My head hair had grown soft and long enough to be kept in bob style and my wife had decided to have my hair bleached peroxide blonde as it looked pretty in my uniform, especially when I was fully made up which was throughout the day now. I had also noticed that my muscle tone had completely disappeared along with all my excess body fat, She was keeping me on a very strict diet. But instead of muscle I seemed to have developed a very thin layer of soft fat tissue all over. My skin was now super soft and I also seemed to be  developing tiny breasts. When I raised this with Her She confessed that She had been lacing my food with hormones and estrogen, which also explained that even in the tiny chastity cage I couldn’t get hard, just occasionally a little swollen. It still throbbed in the tiny cage though. When I complained She told me like it or leave, and that from now on She was so pleased with the results so far She would be immediately doubling and increasing the dose frequently.    

Furthermore I was now to stop calling Her by Her name and to call Her Miss around the house, and if


Her friend was over I was to call Her Mistress and Her friend and any other female friends Miss or Ms. We never really had any male friends thankfully over but if they came over they were to be called Sir. I was now to be called sissy, or maid, sissy maid, Mistress would call me emily in private with the maid or sissy prefix. She chose emily because I had once told Her that although I liked the name it also sounded quite weak and pathetically girly. I was also to curtsy and say thank you whenever I was spoken to by Her or Her friends, and not to speak or interrupt without asking permission.

The hormones made me feel very vulnerable and increasingly emotional and submissive. So even if I objected to all of these dramatic changes I went along with them until it was way too late to say no or demur in any way. & it wasn’t just the ever present threat of being kicked out.  Not being allowed to cum, or even get slightly erect for months now, and now very big


butt plug along with the hormones, was making me feel very naturally submissive, obedient and very attentive, especially when Mistress or Miss as I called Her when we were alone wanted oral sex, which was frequently.

Mistress also decided to introduce corporal punishment, often spanking me before sex so I was even more eager to please Her, and canes for any infractions around the house, or any even minor, tiny imperfections in my housework. Miss enjoyed watching me being bent over and punished with the cane. And She delighted in buying Mistress a riding crop for when the horrid canes were not deemed punishment enough. She also suggested that instead of listening to my blubbing and sobbing for forgiveness, that Mistress gag me with my panties, or Mistresses damp panties for punishment. And they were always very damp when Mistress decided I needed to be punished, and I had no doubt Miss’s were too when She watched. Mistress decided that She liked to gag me with Her panties when She pegged me too, getting even more excited by my squeals and heavily muffled whimpers and moans as She ignored my protests and penetrated  me.  

And I must confess it actually thrilled me the thought of being kept under Her strict discipline, which



was too bad because there was no way I could do anything about the arousal. The cane did sting and smart terribly though and I always felt very small and tiny in my chastity cage after a punishment session. The crop was something else though, burning thudding pain, that would throb and smart for days afterwards.  

And I must admit I was actually quite content to stay at home and do all the housework and was always very happy when She came home. Always ready with a curtsy and to fetch Her a drink after work, or a day out. Sometimes She would allow me to sit, or rather perch primly on the couch next to Her, or a maybe just to stand to one side in attendance, She was never interested in my day, it was always just tedious housework, and She didn’t really talk to me much about Her own work, it was much too complicated and important to discuss with a silly housemaid, She would tell me if if I ever asked about Her day. But more frequently She would send me back to my housework after I had fetched Her a drink. She would mostly keep me busy till She went out for the evening or till near bedtime, when I would undress Her and if She was in


the mood we would have sex, or rather I would please Her with my tongue, or She would peg me then want cunnilingus afterwards.

Then one day Mistress announced that the hormones were coming along very well and I was now very convincing as  a maid. I was very slender and muscle less  now, but with faint curves where it mattered. Mistress said  we would be going out in the near future and that I would be going out dressed.

She brought home a very short wet look satin dress in pink with matching 6” ankle boots for me. The


dress was very short and because it was so short I had matching panties. My push up bra made my very small breasts look quite inviting under the tight pink satin dress. Mistress was wearing a very classy and sexy leather pencil skirt, and black silk blouse. She had a matching leather jacket, I had  a matching pink pvc jacket.

The taxi driver who collected us didn’t know whether to look at Mistress or me, but He did keep looking at me as I tottered to the car on my very high heels and very short skirt. Mistress made me sit in the front next to the driver. It was very uncomfortable sitting there constantly trying to stop my dress riding up. Hoping He couldn’t see my bulge tiny as it was I was still terribly self conscious of it.


I was even more  embarrassed when we arrived at our intended destination. It was in the centre of the city in the area known as the gay village and tonight, like every week was tgirls night. There were lots of transsexual girls most  dressed up to the nines in very tarty gaudy clothing.

Mistress led me into the back of one of the  clubs,  outside in the garden where She could smoke. Miss was also already there sat chatting with another Lady, and a very slim tgirl who was stood to one side wriggling and squirming uncomfortable in an outfit that was even tighter and shorter than mine. I was sent to fetch drinks for all 3 Ladies. Then told to stand with the other tgirl, and try to look pretty.

Mistress commented that maybe I was a little underdressed for the evening but we would do better for the next time. the other women laughed at that. Every so often a Man would come out and chat to the Ladies while looking at us. Stand and pout  prettily, emily, I was told. And wiggle my bottom when the Men were looking at me. Don’t forget to curtsy sissy. I was hot with shame.

I’m not sure now why I never realized what was happening earlier, but I didn’t that first nght. Every so


often one of the Men would lead the other sissy away somewhere. And she would come back a short time later looking quite flushed and with her makeup redone. She would go over to the other Lady sat with Mistress and Miss and hand over something, then she would be sent to bar to fetch drinks, not for herself or me, just for the Ladies.  Soon a couple more Ladies arrived and some more tgirls, and the same thing was happening to those t-girls. But I was just left standing there all night, a couple of Men did come over and looked me over and casually fondled my bottom, but Mistress waved Her head at them and that was all they did for tonight at least. I was very embarrassed and glad to get home in the early hours that night. Mistress did say She had had a lovely night

The next time we went out I was given a new outfit. It was a pleated pink mini skirt in latex, and a very tight pink satin top. My patent PVC jacket and over the knee patent pink boots finished the look.


And tonight was different, this evening when one of the Men looked at Mistress She nodded and went with me and the Man to a small room, Miss came too. The room had a patent leather couch and platform. I was told to kneel down and He took His already engorged cock out and pushed it to my lips. I was horrified but the look on Mistresses face said it all. She had brought the riding crop with Her tonight too. We had practiced fellatio on Mistresses strap on, but this was totally unexpected and completely different. The hot musty smell of His still engorging flesh.  And taste of Him, the very faint but evident taste of stale urine as I began to suck His shaft. The way His cock throbbed and felt so real rather than Mistresses strap on as  licked and kissed it, till He was raging hard.

Its incredible how big an erect cock seems for the first time. And when its right in your face almost in  your lips, ready to push into your lips. Especially when you are confined and so small in your chastity cage.

Look up emily show Him how much you want to please Him sissy, I was told, cajoled. Suck Him


sweetly emily, He is your first after all. He suddenly thrust and pushed deep into my mouth. I was gagged and spluttering but He didn’t relent just held my head with a fist in my hair as He pushed fully inside me. I was holding His buttocks in my hand, usually tgirls are cuffed for fellatio but as this was my first time and first night, Mistress had decided to allow me a little ‘indulgence’. Trying to overcome my gag reflex I started to swallow like I did on the strap on with Mistress, which had the effect of sucking Him in even deeper. And apparently is very pleasurable for the man, sucking Him deep and tighter with the suction. He was quickly at the back of my throat. I heard a gasp of pleasure from Him then a groan and suddenly and quickly He exploded inside me. Filling my mouth and then pulled out and spurted more thick splodges of cum all over my face.

“Don’t swallow until He gives you permission emily.”

I was told, I waited on my knees, choking on the strong thick taste of His cum, until finally He gave me permission to swallow


“Say thank you emily.”

“Thank You.”

“Thank you Sir, emily thank Him for allowing you to suck Him and for being allowed to swallow.”

“Yes Mistress, thank You Mistress.”

“Thank You Sir for allowing emily to please You Sir, and thank You for allowing me to swallow Your cum Sir.” I whispered eyes down in shame my lips sill sticky.

“Look up emily, let Him see how bright your eyes are at being allowed to suck a real mans cock.”

I wanted to look absolutely anywhere but upwards,  but I looked up obediently.

He patted my head. She is a good girl isn’t she, He said to Mistress & Miss  and I’m sure she will


improve quickly.

“Oh yes she will, unless she wants a taste of the crop in front of everyone.”

“Take your panties off and wipe your face emily.”

“Yes Mistress, thank You Mistress.”

“And then lick them clean and put them back on.”

“Yes Mistress, thank You Mistress.”

“Then fix your make up sissy, lots of shiny lip gloss, for a pretty pout emily.”

“Yes Mistress, thank You Mistress.”

The Man then counted out some money and handed it to Mistress.


Cash was barely used anymore, anywhere but the crumpled used notes  seemed perfect to pay for my service.

We all went back out to the smoking area, and I went to fetch Mistress, Miss and the Man a drink from the bar. I had to curtsy to each of them as I fetched the drinks and He slapped my bottom when I bent over with His drink.

I was sent back over to stand with the other tgirls, on display.

And I was taken to the little back room twice more that evening, by different Men. But these times I went alone with the Sir, and instead of giving Mistress the money He stuffed the wadded up notes into my bra to take back to Mistress.


When we finally got home I burst into tears, but Mistress told me to stop being so silly and be quiet. As I lay next to Her in bed I could hear Her & Miss laughing on the phone.

But the next evening out was much worse, as well as performing blow jobs the Men were allowed to take my panties off and fuck me. I was not allowed to protest, I was put into cuffs and gagged with my panties to muffle my moaning. But I was told the me did like it if I struggled a little. Just weakly and prettily Miss had laughed. It was  a long evening and it seemed that when all the regulars knew there was  a new tgirl available for use, so I was popular. The other tgirls didn’t seem to mind though, rather they looked relieved, until their accompanying Ladies, wives, owners or Mistresses, scolded them and told them to look more attractive for the clients. Then they looked quite frightened and very eager to be chosen.

At the end of the night Mistress and Miss were very pleased with the thick wad of cash I had earned. We


can have a few nights with this emily, while you do all the housework. But don’t worry we will go out next week and you will earn plenty more for us to enjoy, isn’t that nice sissy. Mistress said flexing the riding crop in front of me.

When we got home before I was allowed change my sticky clothes Mistress wanted to peg me and then cunnilingus, before She went off to sleep. Again I heard Her and Miss chatting and giggling on the phone a I lay besides Her. Naturally I wasn’t invited to or allowed to join in the conversation.

I was very sore and tender the next day. It was one thing to be pegged by Mistress, She was very passionate, but also gentle, compared to the Men who liked to slap my bottom and push roughly inside me straight away. The lube didn’t help either as it helped them slip inside me so much more quickly and easily b


ut didn’t make it any more comfortable for me. Mistress also gave me a bigger plug in to wear. This one was 10” long and very realistic looking although highly exaggerated too. If anything the bigger dildo made me feel even tighter as I would try to clench my bottom muscles around the very slippery cock constantly. It was like constant kegel exercises while I was busy with my housework. Mistress said I did squirm and squelch prettily on my penetration while I was busy with my housework. Miss had laughed that it looked like I had a pole, or cock up my ass, while I minced about.

I was still tender and very anxious by the next week, but worse was to come Miss had ‘found’ another club where tgirls or sissies went with their Mistresses , that was open on a different night, to our regular night. And the Men paid more but were a little bit more demanding with the tgirls. When I protested Mistress had told me to fetch the crop and punished me in front of Miss. I was gagged with the new cock gag Miss had ‘bought me’ as  a ‘present’ for the rest of the day.

Mistress and Miss were very pleased with the amounts I was ‘earning’ on our nights out. They could


afford to go to expensive clubs and buy lots of nice new clothes, as well as very slutty latex, patent PVC or vinyl outfits for me to wear. Neither of them needed the money, but it was nice for us to all enjoy ourselves they told me.

On the nights we didn’t go out Mistress was nearly always out and not as I first assumed with Miss or other friends. Increasing when She came home there was always Her expensive outfits to wash or take care of. But also  lots of pairs of panties that had to be hand washed, often with faint white stains on them. Naturally from the smell and feel I knew what this was but didn’t dare ask Mistress about it.

Mistress told me I was very submissive and feminine now, effeminate rather. And also that I wasn’t really one of those aspiring tgirls, many of whom wanted to transition. But I was a silly, pathetic sissy  only fit for housework and my superiors sexual pleasure.


Then the bombshell. She informed me that She was tired of our little game and bored of keeping me in chastity and panties. She brought home the man She had been seeing. The man who’s cum I had been hand washing from Her underwear. And announced that we were getting divorced immediately, and She and He were getting married. 

Moreover  my domestic service or any other service would no longer be required. They were both professional people and could afford a cleaner to come in regularly. I had begged and pleaded. I even got on my knees and begged to fellate Him, but He had pushed me aside and away in contempt. Mistress had videoed this on Her phone and Miss took great delight in watching this moment of humiliation.

But I wasn’t to be put out on the street, Miss would be taking ownership of me. To my surprise, Her boyfriend of a long time ago was now, and had been for quite some time Her domesticated sissymaid. Her current very buff and manly boyfriend obviously was not. Her own sissy was kept in permanent chastity and plugged as I would be. We would be kept cock gagged all day so we wouldn’t waste any time gossiping or chatting, while we did our housework. Miss and Her boyfriend were very strict and quick with the crop. And if one of us was bent over to be punished the other was punished too. Sir or Master we were to call Him, nearly always liked to be woken with a BJ, and welcomed home after work with a drink and BJ too. He enjoyed our asses too, when Miss wasn’t in the mood for sex.

As humiliating as I found this,  serving Miss intimately was the most humiliating yet. She would laugh


that it wasn’t cheating and we could have all the sex we or She wanted now, whenever She wanted. As I knelt between Her hot wet thighs, or squirmed on Her strap on, She did like rather large strap ons, both me and Her sissy feared being sent for the 12” cock and harness, nearly as much as we feared being sent for the crop. Miss would laugh,  that from the looks on our faces it was always be better for us sissies to be seen in terms of Her pleasure rather than in terms of discipline punishment, but only just. But I so craved pleasing Her so much, just like sissy, we were so desperate for even the tiniest scrap of attention, affection or approval from Her.

Miss also kept us in very tiny chastity tubes with spikes on the base ring and inside the cage, so that we always tried to stay very soft and flaccid, which was also quite impossible when were plugged and kneeling under Her skirt, listening to Her moaning in orgasmic bliss.

We would be punished for that too, and for the tiny inevitable leaks, pathetic as they were. Miss did relent when we were taken out to earn money for Her enjoyment, as the spikes in our cages made some of the clients feel squeamish and uncomfortable. And were out at both clubs every week.

Mistress would visit Miss quite regularly too but apart from curtsying to Her She never really spoke to me, I was just another of Miss’s maids now.


Eventually though Miss and Her boyfriend also wanted to settle down and have a vanilla lifestyle. So both me and Her sissy were sold to one of the Mistress who owned a lot of sissies. We would work in scene hotels as chamber maids and intimate maids, or in clubs both day and night as waitresses who provided extra for a fee, paid to our owners or renters of course. Or regularly taken out by the pimps to earn money for our owners. When we were not in service we would be kept very busy with a mountain of  housework for our new owners.

But for now one of the clients was feeling and squeezing my ass. He slipped a finger inside my panties to check my chastity, the Men liked to do that. To check, it made it feel not gay for them. He brought His finger out and it was very slightly slick with  a little leak of weak precum. We nearly always leaked a tiny amount when we were being fucked or squirming and squelching on our butt plugs.

“What a naughty fucktoy you are.” He told me looking very pleased though.

“Yes Sir, thank You Sir.” I curtsied


He pushed His finger into my lips and I sucked it clean suggestively, anxious, knowing the pimp would be watching, that He chose me rather than the other sissy, He was also eying up.

He slapped my bottom sharply, causing me to squeal and told me to come with Him.

Trying to be as pretty as I could I minced off with Him. He slapped my bottom  a few times to hurry me along. I could see He was already very hard and eager.

“Yes Sir, thank You Sir.” I squealed breathlessly at each slap.

Causing lots of excited raucous laughter from Him and the other clients in the club.

I knew it was going to  be a busy night.

Saturday, 5 October 2024

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.