2. A Sissies Journey - Maid Made to Serve

 

That first night in locked chastity at home in my flat I had squirmed all night. The device was slightly different to the other sissies devices as it didn’t cover my balls or my sissy plums. And didn’t as yet have the urethra tube. But both would come soon. And it wasn’t quite as tiny as the other sissies devices. I had flattered myself that it was because I was larger than they were. But all sissies were kept as tiny and flaccid as possible and that would come soon. What had I gotten myself into, over and over again in my mind, I just go back and insist She remove the device and walk away. Even though I knew there was zero possibility of me backing out now. Ms and the other dominant Ladies were experts in captivating and manipulating potential sissies into feminized maids. Just like real Men sissies are led by their cocks, and the prospect or possibility of sex. Even though there was little or no chance of me ever being allowed sex again, and even though I already knew that was the inevitable case for me.

And then with  the new butt plug again all night but I didn’t dare to remove it unless I was going to the

toilet. All night I kept looking at my phone, but there was no message from Her. However I must have been finally able to drop to sleep because when I woke up for work there was a message telling me.

“Enjoy your day, sissy.” And She had reminded me that I was now to wear the thongs with my slacks.

The other guys and girls at work had looked at me slightly askance, the thong was pretty obvious, but over the last month or so they had gotten used to my slightly odd behaviour and dress sense and pretty much left me to it. One of the girls who I had a dalliance with though and still fancied me made a point of smooching up to me and feeling my bottom. I felt myself swell up in the cage and blushed, before She giggled and left me alone.

Ms had given me tablets to help with my inappropriate tumescence. They were actually strong hormones, that after a few days kicked in powerfully and made me feel very emotional and vulnerable all the time. The locked chastity device was already having that effect. The first week is usually the hardest but then nearing the first month is very intense. Emotionally like having your first and a heavy period. And it doesn’t go away, just builds and swell the longer you are kept in chastity. The hormones didn’t stop me trying to swell in the cage but I got smaller and softer with each day and even if I had been allowed out of the device I wouldn’t have been able to get anywhere near hard. In fact the only time I was allowed out of the cage now was when Ms quickly and expertly swapped it for a smaller device, this was happening weekly.

When I had asked Ms about the effects She had patted my bottom and pooh-poohed my concerns. She arranged to take me to a  doctor who examined me and listened to Ms rather than my concerns then doubled my dosage and prescribed me an ever increasing dosage to help me with the transition.

 The hormones also made my skin feel very soft and hair free (it was mostly very soft light down now)

But I was waxing regularly too. And the hormones made me develop a thin layer of very soft fat over my skinny body and diminishing muscle mass. I didn’t notice at the time but the tablets were also slowly reducing my height too. As time progressed the newer cages covered my very diminished cherries too and the urethra tube was put in place. Meaning that when I peed, sitting down now of course all I felt was a trickle rather than any gushing sense.  As the chastity got smaller my butt plug got bigger and thicker too seemingly exponentially to me at least, as I squirmed and squelched on the plug in helpless sexual arousal. Ms said I looked quite sweet, especially when I clenched my fists weakly in frustration.

I had been expected to attend the club every evening for some time now and Ms had after a couple of days given me a proper uniform to wear. A very glossy wet look black satin maids uniform with a white satin apron and headpiece, white stockings and patent pink maids boots. The boots had a short 12” strap between them, so I minced gracefully as I served. There were several variations on a theme for the maids  uniform and was changed daily and chosen for me when I arrived, I wasn’t given any choice in the matter. I wasn’t given any of the pastel latex waitress uniforms to wear, they were for just some of the sissies, but some of the maids uniforms I was given to wear were latex. Under the uniform I wore my pink panties, they were very tight and tiny but not thongs, I was expected to wear thongs with my slacks. I was also given a pair of black patent leather maids booties to wear outside the club. The kitten heels were slightly lower and there was no hobble strap.

For the first evening in my uniform I had attended Ms. But on the second evening She had called me into one of the rooms and told me I would be serving and cleaning with the other maids. And that I should be obedient and submissive, curtsy and say thank You whenever I was spoken to, and that if anybody was displeased with me I would be ‘spoken to’ later. As if to emphasize this, She had me fetch the canes from the corner of the room, bent me over and administered 6 hard strokes with the thick cane. Each stroke with the thick rod thudding  & pummeling into the soft muscles and flesh of my backside. After the first stroke I was nearly  sobbing uncontrollably and already pleading for Her to stop.  Casually She pulled my panties down and stuffed them into my mouth then continued. Each blow carefully and very deliberately timed for maximum effect. 

She paused and put the thick cane down. I could feel rather than see Her behind me surveying Her work My rump, my bottom and backs of my thighs  felt like it on fire  with welts forming (actually the canes are designed to avoid the external appearance of wealing as it is considered unsightly. Then Ms picked up the second thin springy cane and continued. Each stroke seemed to cut into my bottom and agonizingly  through the welts as it criss crossed them, I was now squealing into the pantie gag for her to stop. Often Sher likes 6 with the thick rod then 12 or more with the springy cane to follow up. But on this first occasion She was feeling lenient, She told me.

Then with my rear inflamed throbbing and smarting I was told to put my own panties back on & fetch Her a chilled wine and a change of panties for Her from Her handbag. It was so satisfying but made Her thirsty disciplining sissies She smiled as if to sooth my tears. Her panties were quite damp I think She was very satisfied. Often superiors  would gag sissies with their own panties, especially as the exercise of sexy dominance and power is very arousing so removing one set of silk panties for a fresh pair and gagging sissy with silk warm and moist with arousal is a perfect way to enhance the submissives punishment.  But Ms and I were not at that intimate stage yet.

The crop which I would taste later is much more brutally painful. Its leather thudding and ripping into your behind, both excruciatingly blunt and sharp at the same time. The hurry crops used so casually by superiors in the club were different again, designed to severely sting and then smart & throb. Being spanked by Sir open palm was also very painful. The general wide and broad  application of pain by His wide flat palm deepening and suffusing  as the spanking continues. Or the paddles with their wide flat impact.

There were so many ways for the superior to punish and discipline sissies with the deliberate application infliction of controlled pain. But most effective of all was the physical realization of superiority and inferiority. How She or He had the perfect right to punish sissy and moreover enjoyed doing so with no recourse from sissy. Of course this power dynamic sometimes is sometimes exciting for sissy too, at least the abstract thought of it, but the physical implementation, made the satisfaction and pleasure of the interaction purely for the superior cane or whip in hand. Sissy after her first spanking or caning is kept in a state of constant highly sexualized fluster and fright.    

  

My bottom reddened and smarting terribly I was dismissed and sent out to work with the other maids. I was so very anxious and nervous, just a s as sissy should be to be pleasing to her superiors. The patrons seemed to  very demanding tonight, even though they were not.  I felt like I was rushed off my feet fetching drinks and snacks and attending to the superiors every wish and whim. The Men would often slap my bottom or the backs of my legs as I bent over to serve drinks. and fondle my bottom and chastity cage either through my panties or with their large hands inside my briefs. Although my underwear was pink, I still wasn’t pink pantied, so that was as far as it went, but they all told me what a nice little squelch I had as they fondled me. The ladies liked to pat my bottom and make me curtsy deeply several times, causing me to be very aware of my enlarged plug and chastity.

It was intensely embarrassing and humiliating being groped and slapped on the bottom by the Men, and

the ladies, especially by the Men though, but at the same time I was constantly rushed off my platform booties and breathlessly flustered, just like the other sissies.  

When I wasn’t hurrying to serve the superiors I joined the other sissies cleaning and polishing every surface of the club. The maids were not allowed to be stop or be still, while our superiors relaxed, a sissies work is and should never be done.  I took my cues from the other sissies all working diligently and perfectly, no shortcuts whatsoever and at a brisk eager pace, and whenever a superior was nearby or might be watching at a breathlessly hasty pace. The sense of fearful fright and subjugation was palpable and also at the same time highly sexual.

I wasn’t ‘spoken to’ again that night but I was on multiple occasions on the next nights, for what seems like the most trivial or even imagined defect in my service or demeanour. The superior was always right, and Ms’s canes were always very painful and correcting. Ms hadn’t used the leather riding or sissy crop on  me yet but it was always a fearful presence and Ms said She was reserving it for when I need truly punishing or disciplining, or when She felt like using it. The other sissies were often also pulled over the Men’s laps and spanked or paddled, with their panties pulled down and often with their panties stuffed into their mouths. Usually in front of everyone. Ms pondered aloud amused if I would like that as I squirmed with fright and embarrassment. Maybe when I’m pink pantied She told me.

Most of the other sissies were pink pantied and were often taken into the rooms by the Ladies or the Men and would emerge sometime later looking very flushed and sometimes with traces of cum on their faces around their mouths. Their uniforms were always perfect though. I quickly learned the painful importance of keeping my uniform perfectly straight & crease free and spotlessly clean no matter how hard I was working.

On some occasions I was told to fetch drinks to the rooms and would often find one of the sissies serving intimately, either on her knees performing fellatio or bent over and penetrated by one or more of the Men. Despite my fluster I was expected to maintain my composure and serve perfectly, curtsying when spoken to and always saying thank you. Sometimes I was handed a pair of panties to wipe one of the Men clean with.

On rarer occasions sissy would be intimately serving one of the Ladies, kneeling between Her thighs. I so constantly longed to serve Ms that way.

At the end of the night I was allowed to go home. Ms was often otherwise engaged, had gone home or out somewhere else. I went into the changing room and got changed into my thong, slacks and blouse. Then after I had hand washed my uniform. One of the Men would call me a taxi and wait with me. Quite often He would feel and pat my bottom as we waited. And I had been told that I was to nestle into his hand and wiggle appreciatively, even if I wasn’t pink pantied just yet and to curtsy and say thank you Sir every time He spoke to me.

The taxi service was a special service and was seemingly run by dominant Ladies who had a fondness

for uniforms. They would escort me all the way into my flat where I would curtsy and thank the before they left. I always made sure my flat was spotless and tidy now, because I knew that the taxi service would report back to Ms and I would be caned if my flat wasn’t perfect.

Although I was still working Ms had taken control of my wages and She paid my flat and for taxis and I was left with a little bit of pocket money for food. Even that I was expected to account for everything, nothing fatty or meaty, just plain low calorie food for sissies.

Then after around 3 months or so Ms decided that I should have a new job. And She had arranged to have me transferred to an office where I could be kept under female supervision.

It was just announced one evening and the next morning I was to report to the office. It was on the top 3 floors of one of the office blocks downtown. A short trip from my flat but it would involve me using the subway I wasn’t to be allowed to drive anymore. Ms had told me that I was now frequently too emotional and tearful to drive safely, and in any case sissies should be allowed to drive, it was too complicated for our pretty little heads.

I was very obedient and submissive now and did as I was told  without question. However wearing my slacks and thong on the subway was very embarrassing as their were lots of rude Men who weren’t too bothered about being seen to be curious about me. I was frequently stared at and even brushed up against quite rudely. When I had told Ms about this She had said yes a lot of Men are just too boorish, but never mind once I was domesticated sissies are not usually allowed to leave their superiors household. Unless they are being taken to ‘special parties’ She told me teasingly. Later I was to find out that special parties meant being pimped out to parties of Men who wanted a sissy to fuck for a couple of hours.

And in any case the ‘girls’ in the office  as Ms called them would soon look be looking after me.

The office was on the top floor out of 3 and I reported to my new supervisor. She was one of the regular  Ladies from the club and lots of the other Ladies were regulars at the club. I never did find out what they all did there I wasn’t told and curiosity is not becoming in a sissy. Best not to bother pretty little head with these things I was told. My role was purely menial, constantly cleaning and polishing, fetching coffee, sandwiches, and snacks all day.

Ms had also informed me that Miss or any of the other office Ladies could punish me as they saw fit so I had better be a good sissy and behave impeccably. Even so I was regularly summoned into Miss’s office for a caning. She favoured the thin springy cane, I didn’t naturally. But it was slightly less painful than the more frequently used 2 cane method, the thick rod cane then the springy cane as follow up.

On my second day I was given a uniform to wear in the office a little formal maids dress with peter pan

collar and a slightly glossy sheen. It was very short with lace trim and matching apron. The Ladies liked it and the Men who visited the office seemed to approve as well, I was constantly blushing.

One of my jobs was to fetch sandwiches meals and snacks regularly and when I had asked if I was to be allowed to change into my slacks before going out I was looked at incredulously and told of course not and to straighten my apron before going out. I was also expected to fetch drinks and food for the two floors mixed offices below, for both the Ladies and the Men, which was very embarrassing as I was expected to curtsy and say thank you to each of them as I delivered their snacks.

On one occasion I was summoned into the office and Miss had Her boyfriend, the head of the office below, sat there. I was told that the sandwich shop had gotten some of the orders wrong recently and his staff were complaining. Then He put me over his lap and spanked me very soundly. I was so shamed and his large hands hurt by now very soft bottom so much. Afterwards I was told to go downstairs and apologise to the people who’s orders had been wrong. To tell them I had been punished and that it would not happen again. Some of the Men in the office leered at me and some of them looked rather anxious, I wonder if some of them were being singled out to be sissified as well.

I was often punished for this as there was nothing I could do to correct the mistakes in the sandwich shop, apart from run out and change the sandwich or drink by which time it was already too late. On that first occasion after I had been downstairs to apologise I reported back to Miss and Her office stank of sex, both She and Sir looked very pleased with themselves as I tidied up and aired the room. I was very tearful on that occasion. Miss had a picture of Her sissy at home on Her desk, in a very pretty maids uniform smiling & busy at some housework. I couldn’t stop thinking about how the sissy would feel. After Sir had left Miss told me to pour Her a brandy and perched me on Her lap. She patted my bottom and told me not to be so naïve and silly, I would understand soon enough.

“Yes Miss, thank You Miss.” I curtsied, but I was still tearful

Miss didn’t cane me for my silliness on this occasion though.

When I told Ms about my first spanking She had laughed and said She very much approved. And if any of the Men in the club saw fit to they could of course spank me too. Which they now started to do frequently.

Another of my chores in the office was hand washing all the girls panties. They all brought in a small bag each day and I had to individually wash, hang and iron them. Then scent and fold them perfectly giving them back to the Ladies, who just tossed them casually into their bags. I had been doing this for Ms at the club for some time now and it felt very intimate and submissive for Her and also for the office Ladies. Though quite humiliating when all my careful dedicated work was just tossed so casually into their bags.

As promised Ms did arrange for my travel arrangements to be improved. One of the office Ladies would

come to collect me from my flat in the morning. Which meant I had to be up even earlier to make sure my flat was spotless & perfect. I would make and serve the  Miss some coffee I wasn’t allowed coffee or any stimulants anymore. Then we would leave together. Still getting the subway but my chaperone was always quite adept at staring down rude looks. I was still embarrassed though but I felt protected and grateful. When I thanked my chaperone it was often met with an icily but amused response.

“Never mind sissy.”

“Yes Miss thank You Miss.”

In the evenings one of the Ladies would drop me straight off at the club. Or occasionally I would go home with Miss until She was ready to take me to the club.

She had Her own sissy at home and whenever I came home with Her we were both kept gagged, so there was no gossip while I helped with the sissies housework. Miss had  a couple of large cock gags for this purpose. The house sissies was considerable bigger than mine, I would find the reason for this much later again after I was pink pantied. We both worked very hard and diligently but even so Miss still found reason to cane us both frequently.

On a few occasions sissy was put between Miss’s thighs while I attended and served drinks. Then was told to wait facing the wall listening to Miss’s loud moans and climax. I so wanted it to be and Ms in that position. Another time Miss’s boyfriend came to visit and me and sissy ironed Miss’s panties and underwear while the pair had passionate and loud sex in the bedroom. Sissy was summoned and to change sheets and lick the pair clean. And I fetched drinks. Sir sat there on the bed naked while sissy licked Him clean. He patted my bottom and said hello. I couldn’t reply as I was still gagged, but I curtsied sweetly as both He and Miss laughed at my evident blushing.

The most humiliating part was to come as both me and sissy washed and ironed his clothes while He and Miss napped after sex. Later when they both woke up Miss and Sir took me to the club for my evening duties. For some reason I found cleaning his clothes very degrading and emasculating, Ms said that was both interesting and very amusing.

Sometimes Sir would visit and sissy would perform fellatio, or Sir would split and penetrate her ass, while I either hurried on with the housework or attended and served drinks.

The office Ladies also took charge of my depilation and beauty regime. A couple of them would accompany me to a special salon where I would be painfully waxed all over while they sat being pampered drinking wine. Then the uncomfortable electric Electrolysis pads were used to kill off any lingering roots. This went on for some months until by body and face were completely smooth, not just lightly downed but totally squeaky clean. The only way to bring the hair back would be through expensive and intensive male hormone treatment, which wasn’t going to be allowed to me. When the treatments were finished Ms and Miss, and Her boyfriend examined me nude apart from my chastity in the club and Sir had patted my bottom and said He was looking forward to me being pink pantied.

Ms had smiled and told me to get dressed and back to my chores.

I was also moved out of my flat to a small studio flat, to save money even though I never saw any of my

wages anymore they were paid directly to Ms, who didn’t even give me an allowance anymore all my meals were provide at the club and coffee and flowers were provided by a nearby shop where Ms paid in advance for. It was still a subway ride to the office but situated in a quieter part of town. My new room was just big enough for my single bed, the kitchenette and small dining table. There was no TV or internet as I was no longer to be allowed this. There was also a built in enema machine in the small tiled bathroom for my daily ablutions.

I was expected to keep  the flatlet spotlessly clean and tidy, with fresh flowers every day. The flowers were actually for the benefit of the Miss who collected me every day while She enjoyed Her coffee. I didn’t spend any time there apart from sleeping and cleaning as I was at work or the club all day and evening and working at the club all weekends.

I wasn’t to be allowed my slacks and blouse anymore, instead just my formal office maids uniform was to be worn to and from work. And at home just a short satin chemise. And a selection of glossy maids uniforms at the club. At least this meant that I wasn’t expected to wear the thongs anymore. But one of the Men who had usually waited with me for the taxi from the club commented that He missed my tight little butt cheeks so well defined by the thong under the slacks, but my bottom in the tiny panties felt quite nice too. especially when He put his hand under my the very short hem of the maids dress. 

I looked up and curtsied thanking Him. I was flattered and embarrassed, ashamed that it excited and pleased me that He enjoyed feeling my bottom. And wishing that I was still wearing the thong he enjoyed.

He slapped my bottom quite hard but also to him playfully. 

"Keep your eyes lowered sissy, below your superiors belt line."

"Yes Sir, thank You Sir." I blurted my bottom beginning to sting.

He patted my bottom again and I wiggled my bottom for His enjoyment, as I was always expected to.  

"Thank you Sir." I had curtsied, squirming in hot shame.

I did wonder why Ms did not have me move in as Her maid, as I so longed to be now, but She never said anything about it and I didn’t dare question Her.