To love & obey

 

Now I was now longer a sissy virgin and ‘pink pantied’ Mistresses friends came over a lot more frequently with their boyfriends and Mistress and Miss would often just bring round one of their male
friends so he could enjoy my lips and bending me over.

Mistress said it was good way to keep me very submissive and besides which She very much enjoyed watching me be ‘en femme’ with a real man.

I was expected to act coquettishly around real men, leaning very in close to serve them. Bending over fully at the waist, which lifted my very short dress hem and exposed my pink panties,  to serve drinks or snacks. Squealing weakly with mock shock, fluttering my eyelashes when &  if they fondled me or  slapped my bottom as I went past. To which Mistress & Miss would give me cool disdainful but amused looks. And Sir would laugh patronizingly

and be greatly encouraged.

Mistress superciliously told me not to be such a sissy bimbo, after all I was easy and available to any man She chooses to bring home. But I knew She enjoyed making me act like a boy toy even though & especially as She knew how uncomfortable and humiliated it made me feel.

When I had dared to demur even in the slightest. That I wanted to serve Her not men  Mistress had cropped me severely & as I sobbed in fear and pain, instructed me between stinging lashes that a good sissy should always know how to please men. After all most men have quite demeaning desires, like blow jobs and anal sex. And in the past women were expected to be submissive & satisfy those lusts. But now it was only proper that sissy takes care of those demeaning demands not only obediently but with evident desire to satisfy Sirs lusts.

Likewise with housework. In the past women had to do these mind numbingly menial chores. But now these were perfect tasks for sissies to perform and without all the silly labour saving devices.

‘The only house cleaning tools a modern woman needs are Her canes’ Mistress often  said. And ‘Nothing smells as fresh and clean as sissy clean, you can almost smell her  delightful fright in the air and on every scrubbed and gleaming surface.’

I was expected to keep myself pretty and my delicately fussy  uniform spotless as I worked and smile happily with each new task.

Mistress had also started me on an advanced cooking class, so far She was being quite lenient at my attempts but I knew I was expected to improve rapidly.

But by far the biggest change was that Mistress started having Her boyfriends over to stay regularly.

When He stayed over I would serve them as a house maid during the evening. Then later when they went to the bedroom, I would sometimes go upstairs to undress Mistress, or sometimes to give Sir a very quick sucking so that He could last longer for Mistresses pleasure. Otherwise I was sent or would stay downstairs. Mistress liked me to iron and fold Her panties while She was in bed with Her boyfriend. I would also launder & iron His clothes, polish his shoes.

Mistress would generally leave the doors open so I could hear the throes of their passion and I would squirm and grind haplessly on my plug while I worked. My plug was always kept at maximum size when Sir & Mistress were in the bedroom.

I would often be summoned upstairs with the maids bell Mistress kept at hand.

I would serve them drinks, lick both of them clean, take away sticky damp sheets and swap them for clean meticulously ironed smooth sheets. To take away  Mistress’s used nightwear and dress Her again in fresh sexy lingerie. Sir would often wander around confidently naked or just in His boxers. I found this most disconcerting as He was very well built and manly, as were all of Mistresses boyfriends.

Mistress & Her chosen Sir would often fuck 2 or three times until Mistress was fully satisfied. She wasn’t too bothered if He was. He would often wake up in the middle of the night and come into my room for my lips, or to bend me over. I would have to beg Sir afterwards to unbind me so I could get dressed and start my chores in the morning before they woke. Otherwise I would get the cane or crop when Mistress woke. Usually they did though as Sir also liked to be woken by my oral service, with breakfast ready downstairs.

Mistress incidentally preferred Her boyfriend to be woken early and have them leave before She woke or got up. She not wanting to be bothered at breakfast by a  man about the house.

Even though it was mutual pleasure for both parties it was always strictly on Her terms. She always chose well built handsome ‘pretty boys’ She sometimes called them. And they always had to satisfy Her needs before theirs.

I had been quite shocked to realize that Mistress had more than one boyfriend and would casually replace a lover She was bored with. Mistress said She wasn’t interested in a long term relationship with a man, or at least not one She had met so far.

I on the other hand was to be kept strictly for Her and  in strict monogamy for Her. Letting Her male friends play with me didn’t count to Her. She was the only woman I was ever to be allowed to have sex with and that would be always sissy sex and totally & only for Her pleasure & needs. She loved the fact that I had never had sex with another person before Her and as far as She was concerned it would only be with and for Her. Serving Sirs didn’t count, that was just for Her amusement and foreplay.

Mistress also considered corporal punishment as intimate and only between us. The only woman who was allowed to cane or crop me was Her best friend Miss, and even then in very limited controlled circumstances. There would be other times when I was under strict supervision, but that was another matter again.

Mistress also enjoyed cunnilingus and pegging other single, or un-owned as yet  sissies. She also enjoyed anilingus, or rimming with other sissies but very rarely with me.    

One of my first jobs in the morning after Sir and Mistress had left for the day was hand washing Her silk sheets and lingerie. Often if they had been particularly energetic there would be several sets to be washed and ironed. Mistress said She particularly enjoyed the thought of me squirming on my plug in my tiny cage, scrubbing Her boyfriends cum from Her sheets, while She drove into work.

Every morning when She was ready to leave the house I would curtsy and kiss Her bottom, then usually I was allowed to kiss Her pubic mound through Her skirt or trousers of course. I wanted to cling to Her and for Her to stay in for the day. And She would pat my head as I kissed Her quite lovingly but patronizingly and tell me to enjoy my little chores.

& I would say goodbye for the day barely holding back the tears.

Often in the late afternoon when She came home, I would be allowed to kiss Her bottom, fetch Her a drink then be sent back to my chores. But often She would come home and send me immediately for Her strap on. Or depending on if my chores, deportment  or appearance was  unsatisfactory sent for the canes or crop. After I had been punished I would usually be sent back to my chores, until the evening or late afternoon. Or unless we had visitors for me to serve.

My day to day domesticity  of housework, and Her mood and whims.

I loved and obeyed Her totally

Deflowering sissy maid

 

Mistress still hadn’t milked me again more than 3 months later and Her boyfriend & Miss’s Sir were now coming over regularly for oral sex before they went out.

I had to call all real men Sir.

Mistress told me that soon Her boyfriend would soon be stopping overnight & when he did I would be waking him up with my soft lips.

‘Wont that be  a lovely way to start your day sissy ?’

‘Yes Miss, thank You Miss.’ I replied haplessly, almost in tears.

‘Do you want to go and fetch my crop sissy ?’

‘No Miss, Yes Miss, please no Miss.’

‘Well show a lot more eagerness then sissy.’

‘Yes Miss, thank You Miss.’

‘In fact you may go fetch my crop anyway sissy.’

‘Yes Miss, thank You Miss.’ I had sobbed.

One afternoon Mistresses boyfriend, came round even earlier and Miss came round too.

After Sir had cum and He had given me permission to swallow, Mistress said. ‘I think Sir wants that tight little ass you have been teasing Him with sissy.’

I looked round horrified, I was still in the cuffs and my mouth was still sticky with His cum.

I opened my mouth to demur, feebly, but I couldn’t speak and Mistress took Her panties off and stuffed them into my mouth. They were very damp, quite soaked in fact.

‘I think Sir will love your little pink sissy pussy wont He sissy.’

Mistress had, insisted that I had my anus bleached and coloured pink, for when She started pegging me

I had looked at them in tears of humiliation gagged and muffled into silence as I was.

‘Take sissy to Her little room, you can fuck spread that tight little ass of hers in there.’ Mistress said.

“That way she will think about  you when she goes to sleep at night, or your nice big cock at least.’ Miss said

Open handed Sir slapped my bottom and the backs of my thighs to hurry me along. I could tell He was quite eager and excited . Almost as much as  I was quite flustered and numb with fright.

In my room Sir pushed me down face down on my bed, onto my glossy satin sheets and pulled my panties slightly down and slapped my bottom again.

My buttplug was unlocked and removed and with another slap He started pushing inside me.

The more I tied to push back and wriggle free. Crying and whimpering into the panties gagging me. The harder He just pushed me face down onto the bed, enjoying my struggling.

‘Sometimes they moan and whine, just ignore them.’ I heard Mistress say.

 ‘She never learns, she struggles just a sweetly, when I’m pegging her. The more she does the more I enjoy  it.’ Mistress said

‘Oh they never do, my sissy is just as pathetic.’ Miss laughed.

Then Sir started breathing and thrusting very quickly. The panties in my mouth choking me as I struggled to pant for breath.

He exploded inside me massively, I felt like He had suddenly filled me up completely with His cum as He lay on my back breathing heavily.

Mistress later told me it was very sweet that I felt like real men  always came so massively, in my bottom or my mouth, even though it was just a little more than average. It was obviously so much more than I could manage if I was ever allowed. And it showed that I wanted to please Sir and was thinking about His pleasure. 

As Sir pulled out He pushed my butt plug back in and locked it in place.

I was pushed  down onto my knees and His sticky still swollen manhood was pushed into my face.

Mistress pulled Her panties from my mouth and put tossed them aside nonchalantly. ‘Lick Sir clean sissy.’

‘Yes Mistress, thank You Mistress.’ I whispered still gasping ‘Yes Sir thank You Sir.’ I was suddenly very glad of the hot enema that Mistress made me have every day.

As I was licking Sir He suddenly had a spasm and a last spurt of cum, shot into my mouth.

“Oh look sissy another little treat for you.’ Miss laughed.

After I had finished licking Sir clean we went downstairs and I served my superiors fresh drinks, then I was dismissed back to my chores.

Miss had commented on my squelch and mince of shame, as I curtsied and hurried away.

‘Yes Miss, thank you Miss.’

‘Hurry along now sissy.’

‘Yes Miss, thank you Miss.’

‘Sticky panties sissy.’

‘Yes Miss, thank you Miss.’

They had all laughed as I blushed and squirmed, then curtsied again and left the room.

Later I was told to start preparing snacks and drinks for a little party this evening.

When Miss & Sir  had left in the late afternoon Mistress had thankfully allowed me to change my sticky panties and clean my myself and my uniform.

Mistress had laughed about me squelching and mincing about with my sticky knickers, saying how She always enjoyed leaving me in sticky panties after a pegging but a real mans cum is so much more intimate and humiliating for me.

Just before the evening & just before I dressed Mistress for the party. I had been given a new set of panties to wear in the future these were now pale pink. I didn’t realize it but this meant that real men visitors  would know that I was there to please them fully if they wanted it, which they usually would.

I was allowed to keep the panties I had been wearing unwashed but folded carefully in my pantie drawer.

That evening Mistress organized a little party to celebrate the taking of my virginity. We hadn’t really celebrated the first time Mistress pegged me, or the first time I had orally pleased Sir, Mistress had had  a drink with Her friends naturally.  But this was a special celebration, She told me. I was now Her fully effeminized  sissy and there was no going back.

She also later told me that, that after today, She would not be indulging the messy pointless business of milking me. Instead my anxious desire and denied need for release or milking would continue to keep me in a constantly submissive and attentive frame of mind. Meaning that I would serve Her and Her friends so much better, and so much better intimately.

Not only that but She had noticed the tiny leaks I had when I was squelching on my dildo, when I was between Her thighs or on my knees before Sir and that was more than enough, even though I never felt the slightest thing, until I noticed the very faint wet patch. And She would decide whether or not She wanted to punish me for such infractions and nocturnal infractions according to Her whim at the time.

The party was for Her and Her friends. I was as you would expect just there as Her sissymaid serving drinks. None of the guest spoke much to me except to order me to fetch fresh drinks or to comment on how sweetly I minced now, now that I had, had a real man inside me. There were a lot of pats on my bottom too, and smirking comments on my pretty pink panties.

I had been so helplessly hot, needy and and tearful for Mistress after Sir & Miss had left. And although none of ladies at the party wore anything particularly exciting by their standards at least. I couldn’t help but be totally and helpless aroused and frustrated just to see them and be in their presence. I had confessed this to Mistress, fearfully expecting to be punished, but She had laughed saying that was only natural now, that I had been penetrated. The further I was away from having real sex , as a man or boy, the more I would be unable to control my feelings of arousal.

 

I had been a little surprised that Mistress didnt send me for the pink cushion earlier because although I could tell She was very aroused. She said She could orgasm at  any time & when She felt like it. So She was savouring Her enjoyment.

That night though after all the guests had gone She was very demanding & rampart She came several times with multiple orgasms, and the next morning too.

Not only did the aftermath of having a real man inside me make Her very horny, but it also made my intimate service so much devoted and hotter somehow She said.

The next day Miss brought Her boyfriend round and He fucked me too. He didn’t take me to my bedroom though but into the laundry room and used me on top of all the clean laundry which I then had to clean all over again.

Mistress had told Her male friends not to worry about my struggling and protests. It wasn’t coercion or rape because She allowed and enjoyed my forced service. Besides which effortlessly overwhelming my feeble struggling added to the enjoyment.

My wants & needs, or my protests & objections were completely unimportant compared to Her wishes and Her enjoyment, and the enjoyment of Her male guests.

Miss was always teasing me about my curtsy and how I would smooth my apron prettily down in front of me after I straightened up. My fingertips would stop, just for an instant  at the very slight bulge of my chastity cage, then I would continue. Miss said it was very cute & that if I were Her sissy I would be hurrying to fetch Her strap on very frequently indeed. This made me blush every time I did it after that, which delighted Miss & Mistress and embarrassed me even more.

Miss said that Her boyfriend thought that my curtsy was very cute too, but that seeing me hesitate and squirm when my fingers brushed my cage made him think about fellatio first. It was watching me bend over, and exposing my bottom, as Mistress had insisted I do,  to serve drinks, that made him want to bend me over for other purposes.

Mistress told Her that I fetched the strap on quite a lot with Her anyway. And Miss said, the strap on or Her crop, as I was so cute, too cute not to be kept under strict discipline. Mistress said She agreed with that too. Although Mistress usually preferred, but not at all exclusively, Her canes. 

Mistress and Miss constantly teased me about the way I would squirm and visibly tighten my bottom on my plug in whenever a real man was mentioned. Just the thought of such a visit made me feel flustered, totally vulnerable and defenseless. They said it just showed how excited I was to please a real man, like a good sissy should be. And just think how lovely it will be when Mistresses other friends brought their boyfriends round, to see my pink panties.

After I had served them snacks and drinks I had been dismissed to my housework. I could still hear their laughter and amusement ringing in my ears. 

Mistress nearly always hurriedly sent me for the pink cushion after one of the Sirs had finished with me and left 

When Sir cums sissies swallow obediently (with permission of course)

 

Mistress and Her best friend, & Sir were having drinks one afternoon, when Miss asked me if I thought it was time I learned how to please a real Man.

I had blushed and flustered with embarrassment looked at Mistress much to Her amusement.

Miss continued, that especially since I couldn’t take my eyes of Sirs erection when he came round. And especially since I kept teasing Sir with my shiny lip gloss. She  enquired coolly.

And especially as I always stood close to where Sir was sitting when He was visiting. Mistress & Miss had told me, that whenever there was a real man in the room I should stand near Him ready to serve Him.

“Please Mistress, no Mistress.’ I had begged

I was told to fetch Mistresses crop.

Then I was bent over Miss’s lap face down on Her leather skirted lap while Miss locked my wrist in the pink leather belt and cuffs, holding my wrists against my back.

Mistress often used the cuffs when caning me, or if I was between Her thighs and She wanted my hands locked out of the way.

Mistress had stuffed a pair of Her soiled panties in my mouth and I was given 6 severe lashes with the crop.

My rear was burning with pain. Sobbing and in tears I curtsied to Mistress and kissing the leather tab of the crop thanked Her for keeping me under strict discipline.

Then I was asked again.

Sobbing in pain through my tears I replied.

‘Yes Miss, Yes Mistress, thank You Miss, thank You Mistress.’

‘That’s better  Sissy, now curtsy to Sir and ask Him if He wants to let you please Him.

I curtsied awkwardly, still locked in the cuffs set.

‘Please Sir would you like sissy to please you Sir ?’

He looked down at me then told me to get across Hip lap.

Then pulled my panties partially down He spanked me hard until I was sobbing again.

He unlocked my cuffs and I was sent to fetch Him a cold beer and the Ladies fresh wine.

‘Maybe next time sissy.’ He told me curtly

‘Yes Sir, thank You Sir’ I blurted partially in relief and partially in humiliation

I was sent back to my chores, I could hear them laughing as I worked in the kitchen.

That night Mistress told me that if She is ever going to milk me again I would have to please Sir and other real men first.

And that the next time I hesitated I would be cropped again. Not only that but I would have to show Sir that I really wanted to please Him and strive to maximize his enjoyment. The crop will be an excellent tutor for you sissy She told me.

Then I was told to fetch the pink cushion and remove Her panties.

She was very hot and wet tonight and very loud when She climaxed.

The next time Sir came round with Miss I had to curtsy and to beg to be allowed to please Him.

Mistress cropped me again because I wasn’t effeminate and submissive enough in my pleading.

Sir had put me in the cuffs & over his lap again and spanked me.

I was always to be spanked or paddled before oral sex with a real man, it was to put me in my place under His discipline to serve His pleasure.

I was then sent to fetch Him  a bottle of beer and Mistress & Miss more wine, put back in the cuffs.

Sir pushed me to my knees in front of Him, then opened His trousers.

His erection was in my face as I looked up at Him. The smell of him and the warmth coming from his manhood dominating my other senses.

He was very big and hard especially looking up at Him with His erection right in my face.

I felt so tiny and soft in my cage. Mistress increased the size of my plug so it felt like it was filling me up and almost splitting my bottom cheeks.

I was told to kiss and lick Him slowly.

As my lips touched the crown of his glans the taste of Him was sickeningly fleshy and overwhelming. I felt like I was about to throw up at any moment.

“Look up at Sir, sissy let Him see that you want to please Him.’

‘Yes Mistress, thank You Mistress.’

I wanted to look anywhere else but up into His eyes, as He looked down at me expectantly, and expecting to be obeyed.

‘Suck His head in and out sissy, slowly and bob your head  deeper with each suck.’

‘Yes Mistress, thank You Mistress.’

He felt even bigger inside my mouth as I my head bobbed and the motion pressed my lips wider and wider.

I heard him sigh and smile. Then a hot spurt of precum in my mouth.

He pulled out of my mouth briefly

‘A little treat for you sissy.’ Mistress said

Sir and Miss both laughed.

Sir took a swig of his beer and said ‘You may swallow that little pretaste sissy’

I gulped and swallowed the precum ‘Yes Sir Thank you Sir.’

Then He pushed back between my lips forcefully and seized a fistful of my hair as He pushed deep into my mouth.

I was panicking and choking. He ignored my gagging and pressed deep until I could feel Him in the back of my throat. Mistress had been training me to overcome my gag reflex with Her strap on but having a real man push his throbbing pulsing manhood so deep and powerfully into my mouth penetrating me, was completely different.

“Suck him tightly and bob your pretty little head back and forth sissy.’

Mistress had taught me, using the strapon, that the best way to overcome the gag reflex was to swallow as He pushed. The swallowing was extremely pleasurable for Him. And just pulled Him deeper and deep and excited Him so he increased His the tempo of His thrusting .

‘Look up at Sir, sissy, let Him see how much You want Him to cum in your mouth.’

I struggled to look up at Him all I could see was His stomach and feel His manscaped but still hairy balls on my chin. With each swallow He thrust still  harder & deeper forcing me to gag and splutter and swallow Him deeper.

Then with a final push and groan of pleasure He exploded in my mouth. Spurting and thrusting filling my mouth with his thick sticky cum.

When he had finally finished spurting into my mouth and pulled out from my lips.

I had to suck lick the remaining semen from His meatus until He was totally clean  

Mistress said ‘Open your mouth sissy’

I opened my mouth

‘What a lovely thick load sissy, what a treat for you.’

‘Do not spit sissy and do not swallow until Sir gives you permission.’ Mistress said.

I looked up Her unable to speak with my mouth full of Sir cum

I waited on my knees with my mouth full looking up at Him while Sir fastened His trousers and sat back relaxed, chatting with Miss & Mistress.

Then after a few minutes He said ‘You may swallow sissy’

It took me two sticky gulps

‘Remember to say thank you sissy.’ Mistress told me.

‘Yes Mistress, thank You Mistress.’

‘Yes Sir, thank You Sir.’

‘Tell Sir how much you enjoyed tasting His manly cum sissy.’

‘Yes Mistress, thank You Mistress.’

‘Thank you Sir,  For allowing sissy to please You Sir and to swallow your Your cum Sir. It is so sticky, thick and manly Sir, Thank You Sir.’

‘The pleasure was all mine sissy.’ He laughed patting my head.

‘See sissy I told you a real mans cum is so much thicker and creamier, especially when its hot and fresh sissy.’ Miss told me with evident amusement.

‘Yes Miss, thank You Miss.’

‘So much better that your pathetic thin leaks sissy.’ Mistress told me

‘Yes Mistress, thank You Mistress.’

‘Fetch Sir a fresh beer sissy and wine for us  sissy.’

‘Yes Mistress, thank You Mistress.’

I brought them fresh drinks with a curtsy.

‘Hurry along back to your little chores now sissy.’

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

Sir slapped my bottom loudly as I turned to leave.

‘Thank You Sir.’ I squealed as he always managed to hit the base of my plug.

That evening Mistress told me to fetch the pink cushion, She was very excited tonight. After She had climaxed with multiple orgasms, She kept me between Her wet thighs kissing Her lovingly, as we talked.

Next time Sir came over I was to flirt, coquettishly and stay close to Sir. I was to ask to please Him and He would always put me over his knees and spank me before fellatio.

He was always to cum in my mouth and never all over my face, that was Mistresses preference, and while I was sucking Him I was to squirm & grind on my plug as I sucked. Keeping the rhythm, just as i did when i was between Mistresses thighs kissing Her intimately. And although my performance had been adequate today I was expected to improve greatly and excel so that Sir would want lots of oral pleasure.

‘Dress me for bed now sissy and when you have your little nightie on you can please me again. I do so love watching you on your knees before a real man.’

‘Yes Mistress, thank You Mistress.’

The next time Miss came round She had a present for me. A wide pink leather paddle. With a raised detail of little lovehearts and pursed lips. For when Sir didn’t want to spank me.

Sir was a regular visitor but even more humiliating was when Mistress started having Her own boyfriend over for drinks before they went out together. One evening Mistress told me to get between his knees and please Him, while She was getting ready. That way he wouldn’t  be horny all evening when they were out.  After that first time Mistresses boyfriend would often collect Her from home and enjoy my oral service.

Although Mistress had told me I would only be milked again only after I had learned to please a real Man properly I was still waiting and desperately waiting to be milked again 3 months later.

Mistress also gave Her boyfriend and Sir a copy of the key for my chastity devive. It was only proper, She said, that if I was to please them they should know that I was properly locked up.

Although Mistress had told me I would only be milked again only after I had learned to please a real Man properly I was still waiting and desperately waiting to be milked again 3 months later. Mistress enjoyed teasing me saying it would be that day then postponing it at the last minute, or bringing Sir or Her boyfriend round and telling me it was much more important that Sir came then my little leak.

Even though I knew I wouldn’t be allowed to cum, after 3 months so needy, emotional & tearful all the time that Mistress said it was like I was on my sissy period permanently.

Mistress said that it was quite lovely for me to be so vulnerable, submissive and attentive.

 

Mistress called to me from her bedroom. I was still in my pink satin nightie as it was very early and notyet  time to start on my chores. Sometimes Mistress allows me to sleep with Her in Her bed but usually not. As soon as I entered her room I could sense She was aroused. As a sissy kept in permanent chastity you become very attuned to the signs of your owners arousal. The very faint warmth in the  atmosphere and the scent of Her. I squirmed in my tiny chastity device . Even though I was kept permanently tiny and soft, by chastity and hormones,  the tiny silicon lock suddenly felt very tight.

I was allowed to kiss her bottom and her thighs. She kissed my cheeks fondly.

‘Fetch me some coffee and my cigarettes, sissy’ I was told.

‘Yes Miss, thank You Miss.’ She liked to be called Miss when we were alone. She said it was more intimate and naturally more submissive that way.

I quickly fetched fresh coffee and Her cigarettes. She was already waiting for me, sat on two silk pillows with a snug gap between them.

I served her coffee and curtsied then slid between the pillows facing  up and She lowered herself onto my face. She was very wet and warm.

‘Open your mouth wide sissy’

‘Yes Miss, thank You Miss.’ I said from underneath Her.

She let loose a stream of hot urine into my mouth and down my throat.

I swallowed it all not losing a drop.

‘Thank You Miss’ I whispered.

“Good sissy.’ She said happily I heard Her light a cigarette then take  a sip from her coffee.

‘Yes Miss, thank You Miss.’ 

She lowered the hem of Her black silk night robe over my head and straddled my face.

I kept my fingers  on the hem of my pink nightie as if ready to curtsy. She took the remote control for my butt plug and increased its length and girth so I felt very full & penetrated by Her. Usually it was kept at 10” but She often liked it to be 12” if I was serving Her or if we had guests over & especially if we had male guests.

I whimpered and squirmed under Her and She patted my chastity cage and giggled happily. 

I continued to lick Her lovingly as She rode my face and relaxed. Then after 20 mins of service I felt Her breathing & pace quicken. She tightened Her thighs around my face moaning and gasping with pleasure then to climax, several juddering orgasms. I continued kissing and licking Her until Her pleasure subsided. She lay back and faced me. Taking the black silk panties from Her night dress She wiped my face and then gave me them to hold.

After a short while She whispered sultrily .

‘Go and get dressed for your chores sissy.’

‘Yes Miss, thank You Miss.’

I got up gracefully struggling to hide my awkwardness. The cage felt so tight and the butt plug so huge and invasive as I went into my little room and put my maids uniform on. Then quickly did my makeup and nails.

I helped Mistress get up and undressed for Her shower. Then tidied the room quickly before taking her night wear and silk sheets downstairs to wash. I started preparing Her breakfast then hurried back upstairs to dry Her from the shower.

She came down in a robe for breakfast.

When She had nearly finished eating I was allowed to sit next to Her at the table and eat a piece of dry toast and small cup of tea. Although science had neutralized fatty unhealthy food and you could eat whatever you liked these days. I was always on a very strict sissy diet. I was always very happy to be allowed to sit besides Her.

Then after breakfast we went back upstairs and I helped dress Her for work. She always had  a selection of outfits to wear. And often wore leather skirts or trousers to the office. She always looked very much in charge and also to me very sexy.

I kissed Her bottom at the door as She prepared to leave for the day. Suddenly very emotional i looked up at Her, quite tearfully.

‘I love You Miss. I wish You didn’t have to go to work today Miss.’

‘Of course you love me sissy, and I love my sissy.’

‘Yes Miss, thank You Miss.

‘And I don’t have to go to work sissy but its my choice to and I do very much enjoy my career.’

Mistress never actually told me about Her career or what She did, except that it was very important and very satisfying. Apart from that  it was none of a sissies concern.

 ‘Yes Miss, thank You Miss.’

‘And you have your housework sissy.’

I wasn’t never allowed outside the house nor any news about the outside world. My life was one of submissive domesticity. As a sissy maid/wife my only concerns. were my housework and pleasing Mistress.

 ‘Yes Miss, thank You Miss.’

“And this morning was a lovely way to start my day sissy I do love our intimate mornings sissy.’

‘Yes Miss, thank You Miss.’

‘And you can start your day by washing my sheets and my night things sissy.’

All by hand of course.

‘Yes Miss, thank You Miss.’

‘That way you wont miss me too much will you sissy ?’

‘No Miss, Yes Miss, thank You Miss.’ I curtsied, tears welling in my eyes again knowing that these chores made me miss & long for Her especially so.

She lifted my eyes to Hers and smiled.

‘Have a nice busy day sissy, lots of chores.’

‘Yes Miss, thank You Miss, have a lovely day Miss. I love You Miss’

The door closed and locked behind Her.

My first day as Her maid

 

Miss A had collected me from my flat and driven me round to Mistress house. It was quite an imposing 3 story apartment block. Also with a service basement.

Miss A went inside via the front door.

I was sent down to the basement entrance.

Mistress was wearing a rather severe looking leather pencil skirt and black silk shirt. It made me feel weak just glimpsing at Her.

Mistress let me in and took me to a small dressing room. I was told to undress completely. And a rather hot enema was administered.

Mistress then removed my chastity device and replaced it with an even smaller apparatus the tiny cage also enclosed my cherries for the first time.

I was given a new butt plug.

This new plug was  lockable and quite rigid.

The plug was also much longer, stouter and pronouncedly if not exaggeratedly phallic in shape.

And could be expanded by remote control.

Once both devices were locked in place I was given my new underwear and maids uniform.

It was quite lovely, in black glossy almost wetlook satin, with chiffon and organza detailing. Even the apron was lovely.

With a white petticoat to fluff out the very short skirt and white tights. My maids booties were however pastel pink patent leather, and joined together by a very short strap.

I was to be expected to keep my uniform immaculate whilst performing my chores, without exception.

When I was fully dressed Mistress had me double curtsy, once on each foot, ten kneel down.

I was then allowed to kiss Her  bottom for the first time. Once on both cheeks and then once between the cheeks.

Soft, respectful, kisses.

I was then permitted to kiss Her on the front of Her leather skirt on the pubic mound.

Mistress then instructed me to follow Her upstairs.

It was quite difficult to follow Her confident strides, in the hobble boots and the new very thick, rigid plug.

I was quite breathless and flustered by the time we reached the living room.

‘You will have to be much quicker than that sissy unless you want to be fetching my canes on your first day.’

‘Yes Mistress, thank you Mistress, sorry Mistress.’ I curtsied

‘Fetch me and Miss some chilled white wine sissy’

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

After I had fetched wine I was sent to the kitchen, where there was a long list of household chores to start on.

My housework was frequently interrupted and summoned by the little maids bell to fetch fresh drinks or snacks an ashtray, anything the 2 ladies wanted.

At one point I was summoned so that Miss A could take a photo of me on Her phone in my new maids uniform, which She sent to the women in the office.

A short while later I was summoned again so She could tell me that the women in the office all sent me best wishes and hoped that I was enjoying my house hold duties.

Miss A then live videoed me curtsying and saying thank you. There was lots of laughing and teasing in reply.

Later that afternoon I curtsied to Miss A as She left. I was also instructed to kneel down and kiss Her bottom, but only on both cheeks, not between  them.

Mistress would have lots of guests and unless they forbade it I was to curtsy and kiss their bottoms, to welcome them and to say goodbye.

Miss A mentioned they would soon be getting a new office sissy to wear my apron and maybe this new sissy could greet the women in the office by kissing their bottoms. Depending on the prospective owner of the sissies  wishes of course.

I was then sent back to my chores whilst Mistress relaxed in the living room.

It was  a long afternoon and list of chores was seemingly never ending.

In the early evening I served Mistress a three course dinner. Luckily I was not expected to cook, just to prepare the precooked gourmet food, but it had to be served immaculately.

I ate a small sandwich with  a glass of water alone in the kitchen after Mistress had finished eating. Before resuming my chores.

Later in the evening Mistress summoned me to the living room to fetch more wine.

I was told to fetch a small pink heart shaped cushion and kneel in front of Her.

She opened Her thighs spreading Her skirt and told me to remove Her panties.

Then She pulled me between Her legs and pulled the skirt down over my head.

It was the first time I had performed cunnilingus and in actual, fact the first time I had been with a woman.

But Mistress had sent me lots of reading materials and instructions for practicing. As I heard Her moans and squirming increasing She stopped me suddenly and expanded the butt plug, so that it suddenly felt even more massive and invasive.

Then I continued to lick Her steady long slow licks while She wriggled and moaned.

She came but told me to continue licking and She came again and again till She subsided. She kept me under Her skirt in the damp darkness, kissing Her softly for quite some time.

Then I fetched Her some fresh panties and a different skirt. After putting the panties and skirt on Her I kissed Her bottom again and fetched Her some more wine.

‘That was very pleasing sissy, and I’m sure you will improve greatly over time.’

‘Yes Mistress, thank you Mistress.’

‘And in future you will learn to grind and squirm on the plug while you lick sissy’

‘Yes Mistress, thank you Mistress.’

‘Mistress please may I say, I loved serving you that way Mistress, and I am very aroused Mistress.’

She looked down at the cage bulging under my maids dress.

‘That is very sweet sissy.’

‘Yes Mistress, thank you Mistress.’

‘You may go and hand wash my panties now sissy.’

‘Yes Mistress, thank you Mistress.’

‘And I’m sure you still have lots of chores to finish before bedtime too sissy’

‘Yes Mistress, thank you Mistress.’

My plug was left expanded whilst I washed Her panties. There was actually a few pairs to wash and each pair was to be washed individually.

Then the plug was reduced for the rest of my chores.

At bedtime I helped Mistress into a lovely black silk chemise. She did have an extensive range of lovely silk sleepwear and loungewear.

I was given a glossy pink satin babydoll with matching panties to wear. Mistress then took a couple of photos of me on Her phone then pulled me down between Her thighs.
After She climaxed She took more photos of me. On my knees in front of Her.

‘This will have to get much smaller sissy’ She told me tapping on my cage bulging in the satin panties.

‘Yes Miss, thank you Miss.’ She preferred me to call Her Miss when we were intimate like this.

‘And if you tell me you are aroused or feeling horny ever again sissy, you will be caned sissy.’

‘Yes Miss, thank you Miss.’ I whispered frightened but still awfully excited.

Then I changed the silk sheets for Mistress as they were slightly damp and smelly with sex She had said. And dressed Her in fresh lingerie.

Mistress then went to bed and I was sent to the small box room next to Her walk in wardrobe to sleep.

The next morning I was up very early, as every day. Cleaning and preparing the house for Her. Then waking Her and dressing Her, serving breakfast. Curtsying and kissing Her bottom then waving goodbye to Her as She went off to Her high powered career.

That evening I was caned twice once for having a tiny crease on my uniform when I greeted Her. And later when She found some dust in a hidden corner of the room.

After She had caned me the second time She told me that the cane was a very appropriate and satisfying way to discipline sissies.

I was then told to fetch the pink cushion.

In the office, club and cafe.

As well as working in the office, Mistress had me working as a waitress maid at the club most evenings.

And during the day at weekends in a café that catered to dominant ladies.

She said this was to get me familiar serving my superiors in menial & quite trivial roles. And also to get me accustomed to wearing my cage, and plug in public, in tight revealing maids uniforms.

My uniform was the same vinyl PVC maids uniform from the club. I was told that this uniform was best because it was easy to wipe clean. Mistress didn’t tell me at the time but it was especially easy to wipe clean when a Sir had blown in a maids face, or on her uniform, or if a Miss had been particularly excited. I was always given a fresh uniform starting each shift at the club or café. And the pvc always smelled as if just freshly wiped down both inside and out then sprayed with cheap perfume. All the other sissies too wore similar uniform that they were handed out before the start of the shift.

We were not allowed to chat with each other. When we weren’t serving or cleaning we were told to stand facing the wall in silence. Some of the sissies were kept gagged the whole time. I later learnt that the gags were deep and substantial cock gags. To keep sissy quiet and to train her gag reflex.

I had been given a small padded bra to wear under my uniform, until the increasing hormone dosage to develop small buds of my own. We were also being trained to walk prettily with the ever present butt plugs & heels. A sissy had to mince prettily and gracefully, even though you were still constantly, terribly self conscious of your sissy waddle, and how you always felt your were grinding and squelching on the plug. Especially as many of the women were accompanied by men in the café and they would pat or slap your bottom as you walked past and the ladies would comment on your squelch, or your effeminate mince, that was teasing the boys.   

Many of the ladies from the office would come to the café with their friends or boyfriends at the weekend. They would often comment how much more natural it seemed to see me in a pretty uniform. Although the office ladies were usually friendly I wasn’t allowed to chat much, my service was expected to be coyly obsequious and self effacing.  

This wasn’t helped by Mistress choice of footwear for me. High heeled boots with a short chain joining the ankles. This would get shorter and shorter over time, & eventually my maids boots would be joined by a short leather strap. I was very glad not to wear this chain in the office but the Ladies there would always make me walk in dainty careful steps as if were still hobbled.

We weren’t allowed a break during the day, not even to go to the toilet. But I did notice several times during the day some of the men taking one of the sissies into a special private area that I wasn’t allowed to go to at all. And afterwards the sissy would seem quite flustered and, usually quite tearful and appearing especially vulnerable. And her uniform would be freshly wiped and scented.

Next to this area was the discipline room, where some sissies were taken to and caned if their behavior  had been deemed disobedient or displeasing.

I was never taken to this room as Mistress only wanted to discipline me Herself. And only started to use

the cane on me when I became Her resident sissy maid. If I was to be punished She would put me over Her knees and spank me in front of everybody in the club. This was particularly embarrassing and humiliating for me. Because in spite of the cage and the hormones I still felt myself get very aroused, although still soft, in the tiny cage and could sense that spanking me excited Her too.

This public spanking was often done in front of the Lady who had reported my misbehaviour, or videoed on a phone and sent to a Miss or Sir who had felt I deserved corporal punishment. And was often done at the same time Mistress was given my wage packet for Herself.   

At the end of a shift at the café we would all clean up and then line up to collect our pin money. The cleanup before and after the shift was not paid. We were also deducted from our wages a fee for the loan and cleaning of our uniforms. If a sissy had been punished there was a deduction. Some sissies who had been in the special back room were given an additional wage packet.

When we had collected our pin money it was then taken off us and kept for our Mistresses and owners to collect. Likewise with my wages in the office this was handed to me then taken away and given to Mistress. I was just given vouchers to spend in special approved shops for my day to day needs.

We also were informed of any tips that had been added to our bills, the café kept half and the other half given to our owners.

In the club I would usually be paid and then sent home by Mistress towards the end of the night. She would collect my wages then send me home in a special late night sissy taxi. Seemingly staffed by the same ladies who delivered my various special packages. The windows of the taxi were kept curtained and I was not allowed to open the curtains. The driver would escort me to my door and I was expected to curtsy and thank Her before going inside.

There were also usually some men in the club, not sissies but quite casual confident well built men. I was expected to call the ‘real men’  Sir and they were all  usually very friendly with Mistress and the other ladies. Like in the café I found it very embarrassing to be around the real men and Mistress found that extremely amusing.

Mistress, Her friends  and some of the other sissies would stay late in the club, but I was only to find out about the later entertainment when I was a resident maid. Mistress loved the fact that I was very innocent and naïve and just for Her to open and mould to Her needs.   

Despite the fact that I was working nearly all of the time at the office, café & club. And that I was often

unable to sleep, feeling very frustrated in my cage, uncomfortable on my plug and very emotional & tearful because of the hormones. And lonely when I wasn’t with Mistress or under supervisory female company. I was very happy & very much content to be taken charge of & be constantly told what to do and how to do it. Even content to be frequently criticized and punished for my failings, patronized by my superiors. Although I still found it extremely embarrassing and humiliating when a Sir patronized or corrected me.

Mistress said that pleased Her a lot and She was very pleased how Her sissy was coming along. This made me long for Her even more.