A sissy love story

 

She was 25 now and I was just 21, She  had been a friend of my older sister and by far the most clever and popular girl in school, with both the boys and the girls.
My father had simply left us when I was very young and I was brought up by my mother and 2 older sisters. I was a quiet boy more into listening to music with my oldest sister music than sports or playing out. I remember Mistress with my sister once when I was around 13 jokingly teasing me that I should try on one their dresses and let them them do my hair. I had run away embarrassed. My sister had been joking but Mistress hadn't been.   

 Meeting Her again a couple of years later it wasn’t surprising that She was now partner/owner and joint head of a very influential legal think tank. As well coming from  a very wealthy and supportive family She had always been so  smart, determined and ambitious.

What really surprised me was that after meeting Her again was that She took an interest in  me. Right away She was very forward and suggested we start dating. Right from the start there was lots of sexual tension & teasing but no sex for me. Then equally as sudden She had suddenly decided that I should move in with Her. I was totally smitten & in love with Her, how could I refuse. After I moved into Her house, there was still lots of sexual tension and teasing and arousal,  She was very affectionate but in the end She always somehow  postponed sex.

Then very Shortly after moving in  She confessed that I was a little too small for Her. Physically and also importantly insignificant down there. And that what she really wanted from us was a female led relationship FLR. And because I was so sweet and open emotionally, not very mannish, I would be perfect for Her. She had said it in such a sweet confident way though, that I had reluctantly succumbed to Her wishes. And then later accepted Her suggestion of gentle feminization & chastity for me. These lifestyle choices were uner the mainstream but was increasingly popular for the female led relationship lifestyle.

Almost as soon as I had agreed She ordered a small chastity device for me. it was obvious She had been considering this for some time. & as soon as it arrived I was locked up & She took the key.

She also insisted that I practice oral techniques with my tongue for Her pleasure, and we finally started to have sex, well cunnilingus and lots of orgasms for Her but no release for me.

Her next step was to insist I leave my boring unimportant job and live in and do all the  house work

for us for Her. All the cleaning, cooking, laundry and other domestic tasks while She went out to Her important career. Very soon She started referring to me as Her little housewife. Then we started the hormones treatments She had ordered for me. Full body shaving then waxing , super soft moisturizer and cosmetics for me. And then satin panties and the little dresses for me to wear, then a little satin maids uniform. I was to be Her maid and wife.

As befitting my new status She had brought home a medium sized strap on and we finally had regular penetrative sex, when She wanted & with me being penetrated by Her. The strap on  got bigger and bigger and much more realistically phallic. She now insisted that I be penetrated with  a locking cock shaped butt plug all day and night  as an addition to  my locked chastity cage. 

I was to start calling Her Miss at all times, and never use Her name I was also to curtsy whenever speaking to, serving  or greeting Her.

Weekly the chastity cage got smaller, the butt plug bigger, more phallic and my skin became softer and smoother with the hormones.  Although I would still swell and ache haplessly in the tiny chastity cage, when serving Her  I never felt anywhere near hard these days.

She also started spanking me over Her knee if She was annoyed with me. Then She bought a leather paddle, which was much more painful. And I was informed some canes and a riding crop were next on Her shopping list. The cane was very painful but she said very satisfying as  a method of disciplining me & She loved it. The riding or 'sissy' crop was extremely painful and She kept that for reserve mostly. 

She would milk me once every couple of months, wearing black latex surgical gloves. But only if I had been very good with my tongue, and very good at my chores. I always made sure I was. She had multiple orgasms every time I served Her intimately, and the house was always spotless. She often found reasons to punish me though, depending on Her moods at the time. And I never felt any sort of pleasure from the milking just a vague unsatisfying emptiness and I was still always totally horny and attentive to Her afterwards.

She was also going out a lot more now with Her friends and sometimes staying out all night. I hand

washed all Her underwear and did sometimes notice white stains on Her expensive  silk briefs, but never dared to ask Her about this. We had never discussed infidelity or other people. Miss simply took it as her right to have other partners, just as it was Her right to keep me locked in chastity and to enjoy my tongue whenever it pleased Her. Cuckolding was such a silly term I had heard Her laughing on the phone to one of Her friends one evening, but again I was both embarrassed and didn't dare ask. And I was supposed to close my ears somehow when Miss was on the phone with Her friends.  
She also insisted I wear Her discarded panties after She took them off for the evening so all the next day I would be wearing Her soiled but lovely silk panties all day. Often when they were so stained. and my own body heat while I worked made the panties feel so damp. I would get so hot and horny with the sensation and Miss said She loved coming home to my tongue when I was like this.

It had been a long year now since I started chastity and She was often very rampant wanting my tongue or to use the strap on, and I was always very aroused and needy but kept frustrated.

She did constantly tell me how lovely and attentive I was after a pegging, and how much She enjoyed my tongue. Which always mollified and flattered me, the hormones, chastity and plug  were making me feel very emotional now and I was a such  silly sissy maid

It was vacation time for Miss and I would be going with Her. With a shock I realized that this would be

the first time I had left Her house and its walled gardens in nearly a year. I would be going as Her maid and wearing my little dress and apron  and my chastity and plug. Her friends in the city were very rich and they had sent private jet to collect us, as we were going to NYC. It was  only a couple of hours drive, but much quicker in the jet. Mistress could also have afforded private jet hire & possible even one of Her own, but Her friends were very generous, so She said it seemed rude not to accept the invitation. 

I was to call Her Mistress in public and company, denoting Her ownership, other ladies were to be referred to as Miss. 

I was also given a very pretty new maids dress and apron set to wear, the wet look satin  was highly glossy and also cut very short. The matching glossy petticoats and panties were clearly visible as I hurried about my chores.

When we got to NYC All I really saw of the city was through the heavily tinted back windows on the short drive from the private airfield and outside in the street briefly when carrying all the luggage inside Her friends house. Mistress of course would see lots of the exciting city & be out socializing and shopping a lot with Her friends, I would not be.

The household was another FLR lifestyle house, but sapphic and S&M in nature. Mistresses two friends were in their late 20’s and were a couple. There was  also a House Miss to supervise and discipline the servants & 3 lovely female maids. The House Miss was Mistresses age. And the 3 maids were the same age as me give or take a month or so and although they were employees were subject to discipline and corporal punishment if they were displeasing as part of their conditions of employment, they seemed to be turned on by this as well actually fearful of Misses cane. The house Miss for Her part also seemed to really enjoy this aspect of Her role and was very strict with all the maids and would relish being so with me.

On arrival the House Miss  took me and the other maids into Her office and told me to go over to the wall & take Her cane

from where it was hanging &  to bring it to Her, holding it across  both hands, open palmed and to curtsy. She left me standing for a few seconds then took the cane very deliberately from my hands And examined the implement, and flexing it. Then I was told to return the cane to its hanger. I was to be in no doubt that the next time I brought the cane to Her it would be for discipline. Mistress had only just started to use the cane at home but this one looked  thicker but springy at the same time, and very well used. I was trembling when I returned the cane to its place hanging prominently on the wall. & the other maids said I had quite paled with fright. It was so very well used shiny and worn in parts.

I was the only sissy in the house and the other maids were always giggling at my pretty and very revealing uniform. Their uniforms were also short and pretty but not quite as glossy, and not as difficult to keep clean and uncreased as mine. All our uniforms, hair, make, nails had to kept spotless at all times.

I was to call all ladies Miss, and the maids miss with a small M

For our month long vacation I would be joining the maids in their duties. I would also be given the extra task of hand washing and ironing all the maids and ladies of the house underwear. And as a special treat I would be allowed to wear the maids unwashed panties for the day after they had worn them. Also if I was to be caned the house Miss would gag me with a pair of the maids unwashed as yet, panties. Mistress adopted this practice when we got home for punishments and for pegging, using her own just removed panties.

The maids panties were a little smaller and tighter than mine and even though the pink chastity cage was quite tiny the small briefs made it feel even tighter. On seeing this Mistress had immediately ordered me some new smaller panties, for when we got home.  

The maids all shared a bedroom and two double beds in

the attic room and I was to sleep there too. Later that afternoon one of the maids had taken me upstairs to use the toilet. Mistress usually supervised me but on this trip insisted that one of the maids took me and made sure I sat down properly, like a good sissy. When I had finished the maid sat on the big bed took down Her panties. I was told to kneel between Her thighs and She peed into my open mouth. Only Mistress had ever done this before. Then I was told to lick Her clean and continue to kiss and lick Her intimately. She came very quickly and passionately, clamping Her thighs around my face squirming with pleasure. She had been horny all day ever since She saw my little dress and pink chastity cage, She told me. I had started to protest but she pressed a finger to my lips and asked me if I wanted her to tell Mistress if I was being a good sissy or not ? The answer was plainly obvious.

Mistress had already decided that I was to serve the maids as, when & how they pleased, as long as it didn’t interfere with their or my household duties.

The pretty maid smiled satisfied told to fetch Her a clean pair of panties and put them on Her. She was even prettier after she had climaxed, just like Mistresses flushed with sexual satisfaction. As I was kissing Her still warm bottom afterwards the other 2 maids came into the room giggling. One of them was touching herself, but the other maid stopped her and said there was no need for that while I was here. I gave me her wet finger to lick clean. 

 They told me to stay on my knees and took turns with my tongue, while the other 2 watched. After all three had loud orgasmic climaxes, they kissed me on my cheeks and sqirmed and wriggled while cuddling me. I was squirming helplessly in my chastity much to their enjoyment and satisfaction. But I did feel very sisterly and cared for in their affectionate embraces.

Because as a sissy  I was the least in the household the maids were also to be allowed to spank me if they wanted to and in future they often seemed to enjoy this before intimate oral service. Either over one of the maids laps who was spanking me, while other two watched.  Or over one of the other maids whilst another spanked my bottom soundly. I could always smell their hot excitement after a spanking and that and the spanking itself made me feel very tight in my chastity.

After one of them had spanked me for the first time, I told them quite tearfully that the hormones kept me exceptionally sensitive down there. They had giggled and kissed me sweetly. The maid who had just spanked me sat me besides Her and told me soothingly that they would only spank me if they thought I needed it, or if they really wanted to, but I had best be on my best behaviour with them.

So they still found a reason nearly every night to softly spank me before I pleased them with my tongue and it was very arousing for us all and very satisfying for them. Though I must confess their spankings were less severe than Mistresses were and seemed much more like fun and foreplay to the maids pleasure. I shared a bed with one of the maids and the other two the other bed. it was nearly always the last maid I had performed cunnilingus on and she always wanted to cuddle and to rub herself on me and especially my tiny chastity cage as she drifted off to sleep. They never wore panties with their nightwear but I had to always wear a pair of tight satin panties for bed. When the lights went off, you would hear, giggling and increasingly excited sighs and moans from the other bed. The maids were very naughty with each, even without me there. And the maid who I was sharing a bed with would cling to me tightly,  actually we would cling to each other, listening, usually until the other two finished. Or the maid would either push me down to her intimacies or touch herself. Quite often they would swap beds or my tongue. most nights when everyone had finally gone to sleep I would be squirming in the beds wet patch, listening to their contented naughty sighs. I would have to wash the sheets and the maids nighties in the morning.      

One morning the House Miss caned me because I was a little bit slow doing the laundry. And also because She simply wanted to. She was also visibly aroused by this and after this first occasion  She often found a reason to cane me for the tiniest of things. And I knew that She would be sending me not for the canes later but for Her strap on, for  a pegging. Or maybe for  a caning and  a pegging if She so pleased.
Only Mistress had ever pegged me before and the experience with Miss was equally erotic and emasculating, I felt so vulnerable and needy afterwards. She loved to penetrate me very vigorously until she came gasping and moaning behind & inside me. Sometimes I was immediately sent back to my chores at other times Miss would allow me to bring Her a a drink afterwards then stand facing the wall until She dismissed me. Often another maid would come into the room to see Miss and I would hear little giggles and sense the smirks, as well as smell the arousal, behind my back. 

Miss didn’t however often want cunnilingus from me, seemingly She preferred that with the blonde maid, who I think was Her favourite. She  would smile at me with Her lips still glistening, kissing me on my lips and tell me my turn with her would be later. 

The maids too could use the  strap on if they wanted to, but after a little experimenting they much preferred my oral service. They were after all submissive, except with me 

The 3 maids were always very sweet about my chastity and said the pink medical silicone device looked very pretty and at least I could bring them orgasm, which was lovely.

Between the maids and the House Miss My bottom was kept very busy as was my tongue. At night the maids, them took turns until they were happily exhausted and ready to sleep. I was so desperately and helplessly horny in my tiny cage, I was constantly emotional & flustered. The house Miss took a great deal of pleasure is making sure I served perfectly though & I was often caned. The three maids were also often caned, but not as much as I was I thought.

Mistresses 2 friends were not very interested in me sexually apart from  a little teasing, they were much more interested in Mistress and it was mutual for all three of them while we were here. 

In the evening  Mistress and Her friends would often have visitors, both male & female & we maids were in attendance. However I was often sent to bed earlier than the other maids

Then one evening one of the men followed me upstairs to the attic. He pushed me down onto my knees and pushed His fully erect cock into my face, pressing it between my lips. He was so demanding and dominant that I didn’t dare disobey Him. Then after He had cum all over my face and ordered me to  swallow. I felt so humiliated swallowing His cum but then He tied my hands up, took my panties off and gagged me with them and forcefully anally raped me. Then He left me face down sobbing on the bed until one of the maids came upstairs.

She took me down to Mistress. Mistress was very annoyed at my tearful state

 “It wasn’t rape because you are mine  & I allowed it sissy.” She told me sternly and I was to go into the reception room and continue serving. Moreover I was to bring Him a drink  curtsy and thank Him, and ask if He was pleased with my service. Unless I wanted to be caned in front of Him  and everyone else beforehand. I dried my tears and hurriedly obeyed.

That night I was allowed to Her bed with Her for the first time this vacation. She said the oral sex was absolutely delightful.

The next afternoon the maids took me upstairs and taught me how to give a good BJ and overcome my

gag reflex using the strap on. You must always keep suction and allow Him to go as deep as He liked. And He liked it if you seemed to gag and splutter a little when He went deep. You must always look up at Him when you were bobbing your head on His cock. And always wait for His permission to swallow after He has cum in your mouth. To always say thank you to Him. And yes swallowing His cum was icky, but good girls and sissies always swallowed obediently. Mistress also told me that sissies should be grateful as that was as close to cumming she would ever allow me to be.

When He bent you over He liked it if you struggled and moaned when He penetrated you. I said I wouldn’t have any difficulty with that ever. The maids giggled and said probably not with that tight little sissy bottom. She gave me  a playful slap on my rear.

There was still another 2 weeks of vacation to go and there would be lots of male visitors for me. They

were friends of the ladies and previously one of the  maids would  serve them discretely, as part of the scene, house hospitality, so to speak. 

But for a feminized sissy the men would always pay and pay handsomely. Mistress said we were so much better at fellatio because after a little insistent coaching and cajoling we instinctively knew how to please a real throbbing cock. And also the sissies pretty, lovely tight bottoms were perfect for penetration. All the visitors were all rather buff and well endowed too, further adding to my total emasculation.

The visitors kept coming and asking for my services. Asking Mistress and the house ladies rather than asking me.  The maids would constantly tease me saying I was having all the fun, and all the icky taste too, but they still all enjoyed my oral submission nearly every night.

By the time the vacation was over all my visitors said I was a very good little whore and my service had improved considerably. Mistress and the ladies made  a point of counting out all the money I had 'earned' and sharing it out, even the maids got a little bonus 
When we went home Mistress, had decided that after our interesting little trip. There would be some  immediate changes in our lifestyle & relationship.

She had decided that we would be relocating to an apartment in NYC. And shortly after our move She very soon started bringing Her boyfriends & girlfriends home rather than always meeting them for sex when She was out. And having Her lovers sometimes staying the night. I was left in no doubt that this was Mistresses prerogative  and I had no right to be upset or object in any way. Though Mistress did enjoy the fact that I was jealous. 

I wasn’t expected  to serve the boyfriends usually as they were Mistresses lovers but they sometimes wanted fellatio and Mistress said She enjoyed watching, especially as I was locked up and not allowed to cum as they enjoying spurting into my mouth and face.

Mistress also now started to take lots more vacations & extended business trips. And  whenever She did I was usually sent over to stay in the townhouse with the maids and the House Miss with Her scary cane. Often collected by a rather scary looking chauffeur in a limo with blackened windows & a couple of times in the back of a van. One time I had to thank him with fellatio but he wasn't really interested in me after that. He did like the maids though. There were always lots of male visitors arranged for me. The maids teasingly told me that all the boys would ask when was the next time I would be coming over, much to everyone’s amusement, except mine .

Then after a 2 more years without me ever being unlocked,  and kept in total chastity, Mistress announced She would be marrying one of Her boyfriends and planning to have a family. I was heartbroken but it was Her decision to make.

She would provide me with an income and help me find a nice job & I could go back home and to normal vanilla life. Or I could choose to  be sent permanently to the townhouse. Where eventually one of the other Mistresses on the scene might choose me as Her own  personal maid. I had been very well trained and was totally feminized, obedient  and lovingly submissive now. If I chose this option, it would be up to the two ladies to decide who my new owner might be.

I didn’t want to leave Mistress but It was Her choice as always, and I couldn’t leave the scene  after 4 years of chastity and the FLR scene. When She said goodbye to me in her lounge, Her new future husband was sitting with Her. I had curtsied tearfully and She had patted my bottom  and told me She knew I would soon find a new Mistress, who would be very loving and strict with me. Or a new Master or Sir, She said patting my bottom again as I minced away with the driver who had come to collect me, and my little collection of uniforms, aprons and panties. 

The Ladies, House Miss and the maids were all very pleased to welcome me. And actually after the first few months the House Miss took me home to be Her personal maid for about six months. And then one of the maids & I went to live with  a Master for around a year. But eventually we both came back to serve and live in the house until an owner could be found for me. There were a few intimate viewings and examinations, both Mistresses & Masters, until eventually a very strict Mistress decided I was exactly what She & her husband was looking for and took me home to live with them. 

For a  life of strict domesticity and blissful sexual obedience. From me and for Her and Her husband. The couple were not interested in having a family so I was just for them. And although they did have lots of visitors both dominant and vanilla, male and female. Even Mistress and or the 2 ladies on occasions. And there was lots of teasing and sometimes fondling I was strictly for the couples sexual enjoyment. I was also never allowed to leave the house and if there were trades people in the house I was locked in the basement while they were there.

Mistress and Master eventually employed a  female maid to act as a head maid and House Miss for me. She was the same age as the  3 maids and was friends with them. Miss never did much work around the house but She often shared little bits of gossip with me, while I worked. She also disciplined and punished me as She saw fit, spanking and paddling me, the canes and crops were just for Mistress and Master.  She also had a very painful leather tawse and She could enjoyed my oral service, whenever She wanted to,

penetration or pegging was strictly only for Master or Mistress to enjoy.

Master would usually arrive home before Mistress and I would greet Him with a whisky and

fellatio, before saying goodbye to Miss for the day. Mistress would arrive home  a little later and would want a hot bath ready and my attendance. And sometimes if I was very good intimate service. Ready for their evening, with me in rapt obedient attendance.

 

 

  

 

    

     

Cock gagging your sissy maid

 

Mistress was enjoying early afternoon drinks with one of Her friends. It was  a hot sunny day and the balcony veranda doors were open, the intelligent air con was on full too. The sissy attending them was grateful for the cooler air, although she was expected to stand in the background where the room was warmer. Often sissy would be stood facing the wall until needed, but for now Mistress and Her guest wanted attendance. The two sissies in the hallway were busy scrubbing and polishing, stifling in the stuffy air. The intelligent air con which could be set to follow you around was only for the superiors. In any case Mistress had decided She would be cock gagging them later. They had both been cropped earlier, but the cock gagging was just for Her own amusement. I was the sissy attending Mistress and Her guest today and would also be cock gagged after some delightful cunnilingus. We would stay that way until they were sent down to the hotel to serve the male guests. Plugged both anally and orally with large phallic dildos and always kept tiny in chastity. Most Mistress kept their sissies fully anally penetrated all the time, & some both anally and orally, but Mistress enjoyed the additional pleasure and humiliation of imposing the cock gag as punishment, discipline, humiliation, or simply because it pleased Her.

Like the butt plugs the cock gags were overlarge and exaggerated phalluses. Realistic feeling but very

stiff and inflexible. The taste and aroma too was realistic, so we would be gagging and half chocking not only on the size and taste but with humiliation too.

Mistresses guest had commented on how lovely all the sissies were as usual. But especially on this occasion, mincing so sweetly and gingerly. So breathlessly flustered and anxious to please, as sissies should be. Emotionally overflowing, on the verge of tears.

Mistress had laughed and told Her guest that Her sissies were always like that around Her and Her female friends. And also naturally around male guest at the hotel. Nonetheless She continued the Misses hadn’t toileted us this morning, saying it was too hot and sticky, and bothersome.  And they had wanted to enjoy their break in the early morning sun. A little distress on our part was unimportant, to interfere with our superiors wants and needs.

   

Also as this was high season we sissies were always  a little more dainty as we minced about our chores. We were always a tender and slightly sore from serving all the additional guests. Who being Men were often very enthusiastic at this time too. So afterwards were very careful to keep our posture and gait perfect despite the soreness. & the House Misses were always a little stricter too, so were perfect for the guests. We were given  extra lube at these times but the slippery lube was for the Mans pleasure and kept us very tight for them.  

The silicon based lubes always felt so incredibly slippery And we felt very wet down there but it wasn’t really wet. It made our butt plugs feel so slippery and difficult to hold, meaning we couldn’t help but  wiggle and mince as we hurried about our chores. Constantly grinding and squelching haplessly on the overly  large rigid phalluses that kept us totally & properly penetrated.

Some Mistresses liked to use lip shaped  O gags both orally and anally keeping a sissies pleasure zones fully and wide open for a mans use. The very large O shaped rings were usually kept filled with large dildo until service was demanded. Mistress sometimes experimented with these devices, If a guest requested them, often it would be a group of guests who requested this, but generally She preferred us to be kept tight so the man could enjoy opening us, with His cock, or Mistresses with Her strap on.

The lubes ensured  our bottoms were kept super tight and extra virginal feeling for the mans pleasure. And ensured we always moaned prettily in helpless distress as they penetrated us, just like virgin sissies opened for the first time, every time. Every new season Mistress & the Misses would say they have a nice new lube that will make us feel even tighter for penetration, but in reality its just auto suggestion to make us sissies feel more vulnerable when we see or feel Sirs huge erection.

The extra lube at this time made our bottoms generally even more sensitive especially to the  stinging open palm slaps that the Men were so fond of. And we would squeal so prettily for them.    

We sissies all had a hot enema first thing in the morning and late afternoon before the evening duties, so our bottoms were nice and clean, fresh for the Sirs enjoyment. Sometimes if we were very sticky after a group of men we might be allowed another enema during the day too.

Mistress and the Misses often cancelled our toileting on a whim, they found it quite amusing watching us squirm with need. Especially as the overlarge phallic but plugs constantly massaged our prostrate gland makes us constantly feel the need to go.

This also had a  desirable effect of making us even more extremely attentive and

very sensitive when touched, slapped and fondled down there as we often were. Mistress smiled as Her guest patted my bottom rather sharply with an appreciative laugh.

She explained to Mistress She also often accidentally on purpose neglected to remember allowing Her sissy to toilet in the morning. And would often suddenly remember but decide that She needed to pee instead before leaving for the day. Using sissies mouth at these times was so pleasurable, She was often tempted to stay a bit longer and enjoy oral service. But usually opted to wait and combine it with a pegging when She came home.

I had squirmed uncomfortable at that and Mistress had patted my bottom again. She often used our mouths to pee. As She had done with my mouth after punishing the 2 sissies in the hall, Her panties when I removed them had been quite damp with arousal too.

Casually Mistress agreed, it was very pleasurable indeed She said with  a little laugh.

“Isn’t that so sissy?” She asked me.

“Yes Mistress, thank You Mistress.” I curtsied blushing.

“Isn’t that sweet.” Miss commented.

“Yes Miss, thank You Miss.” I curtsied again.

The male guest often commented  favourably on the change in our demeanour as had the Misses, on these occasions. Mistress has often considered making this a permanent change to our routine, but like the cock gags She and the Misses enjoyed imposing it for their amusement and pleasure.

When you were allowed to go it was always just a faint watery leaking sensation rather than any surge of relief or gush. The deep urethral tube made sure of that. We were not allowed to experience that male pleasure. And always sitting like good sissies.

Mistress had also recently decided that in future sissies would accompany the Misses and female guest

to the toilets and if the Superior  so desired wipe them with either scented paper or soft silk towelettes. Just for pee, most Mistresses did not enjoy being wiped or licked at the rear by sissies. Or only enjoyed being licked there for sexual pleasure. And we would not be licking them clean that was only for Mistress. We already attended the superiors to the toilet, wiping it perfectly for them clean before and afterwards. Mistress guests watched me curtsy and squirm a couple of times. Then reminded me that when I was speaking to any woman who wasn’t my owner and Mistress I should always think of myself as kneeling behind Her and kissing Her bottom while I was talking and at that point, that my dildo plug was Her deep penetration.

“Yes Miss, thank You Miss.” I curtsied squirming on my plug.

And of course when talking to a real man I was to visualize looking up into his eyes ever His massive erect cock, my lips and mouth still creamy with the remnant of his thick cum, that I had just swallowed with His permission of course.

Mistress and Her guest chatted about how it now the busy season of high summer and we had lots more guests and parties. The beach area and the other wing of the hotel was open and staffed by sissies whose Mistresses or Masters were away and they were being boarded, earning tips for intimate service whilst their owners were away. The sissies at the beach cafés all wore a variety of lovely tight latex/vinyl pastel waitress uniforms, with matching panties. The uniforms looked ever so tight and sticky but also quick to wipe down after intimate service.

And it was rumoured that their chastity cages, dildo plugs and other sissy paraphernalia  were also all in matching colours.

Some of those sissies, being boarded or kenneled for the summer also served women guests intimately, if their owners permitted it.

We were never allowed to mingle with these sissies as Mistress liked to keep us very exclusively for Herself and the guests of and in this more expensive part of Her hotel.

Busy season, high summer, spring and winter holiday periods usually meant we were at least twice as busy all day, evening and night, and regularly 4 or 5 times as busy as normal. Most days we intimately served the male guests often in excess of 20 and parties of men all day. And as the Misses often commented we minced about so prettily at these times. Mistress always laughed and patted our bottoms patronizingly, just because we were obviously a little bit sore and  uncomfortable down there, we should still be kept fully plugged. And never daring to be anything other than perfect delicately prim and graceful as we hurried about our maids duties and serving the guests.

This was  a good time for  Mistress and the Misses. The Misses would get very good bonuses from all

the extra services and extra tips we sissies earned for the hotel. Of course these bonuses were for our superiors to enjoy and not us sissy maids. We were there to obediently love & serve our superiors and were never allowed to even see any of the money. The Misses would take time off for expensive vacations once the season had finished. & tell us sissies all about the wonderful times they had and all the lovely things they bought. Mistress would often buy Herself lots of new expensive clothes and luxuries too. We sissies were sometimes rewarded too with pretty new maids uniforms and lingerie to wear to perform our domestic duties, and to excite & intimately serve the Sirs in.

Mistress and the Misses always commented on how lovely it must be for us effeminized sissies  to wear such pretty new uniforms for the real men knowing that it was partially paid for by your intimate service. His cock so large and erect, so big in your mouth or your bottom from his enjoyment at your pretty uniform. While you were kept plugged and tiny in chastity of course. And you must always look up deferentially thank Him so sweetly for allowing you to suck His cock and to swallow His creamy manly cum. In sissy awe at His strong lusty pleasure and its thick sticky taste.

And Mistress was always experimenting with new hormone treatments and lots of new techniques to enjoy Her sissies more. In these days of easy, convenient but expensive cosmetic treatments. Some Mistresses liked their sissies to have implants but Mistress preferred the effects of the strong hormones She gave us. Giving us soft tender swelling buds that had a  sweet bulge under our satin uniforms in a push up bra. The hormones kept our tight little bottoms shapely and our waists flat and well shaped for Sirs enjoyment. The treatments also gave us pretty effeminate faces with nice full plump lips for fellatio.

Reduced our heights and body mass if we were too tall and nice slender soft musculature. And of course lovely completely smooth soft skin and nice soft textured hair, for styling in sissy bobs. Mistress liked us to have enough pretty hair for Herself or a Man to take hold during intimate service. Although Mistress often favoured lifting putting the hem of Her skirt over our heads when we were granted the privilege of pleasing Her. And it was so lovely in the intimate moist semi darkness serving and loving Her. Mistress sometimes liked us to keep our eyes closed when serving Her. And sometimes She likes to see us gazing up adoringly. 

When we were serving the Men orally we were always to look up submissively,  showing Him that we are eager and attentive to His pleasure and enjoyment. Sometimes Mistress liked to blindfold us for a pegging and at other times liked us to be facing a mirror so we can see Her enjoyment. & of course so She can see our faces as She spreads and opens us with Her massive strap on. The same for the Sirs some liked to see our faces as they fucked us, enjoyed watching and listening to our pantie gagged cries and moans of distress. And some of the Sirs paid extra to use a tight leather fully closed hood bag, keeping us blindfolded when they forcefully penetrated our tight behinds.

These hoods were patent leather both inside and out, but were cleverly fully breathable, though very hot and stuffy, Stinking of sex and fear The hoods buckled closed around our throats, with a D ring to attach a short leash if needed. Like all our restraints the hoods could also be locked with pretty but secure heart shaped padlocks too

Incidentally one of the first treatments imposed on  feminized sissies, is total reduction of the Adams apple, for cosmetic reasons and so our voices are soft but breathlessly high and squeaky, but also very low and deferential in volume. The other treatment is a frenectomy, combined with extensive tongue exercises, for additional flexibility and for Mistress pleasure during cunnilingus.

A sissy chosen for this service would locked in the waist cuffs securing her wrists behind her against the small of Her back.  The helpless sissy would then be hooded in the snug black hood, its buckle closed securely around her neck. Often leashed and taken, led blindly stumbling, but trying to mince prettily through the crowded main room. She might hear some cat calls or calls of encouragement to the guest who had selected her. Often She would be hurried along with a few snaps of the crop on the rear of Her legs and bottom. Ordered sharply not to keep Sir waiting between snaps with the stinging crop.

Sissy would arrive breathless and flustered then left in  one of the rooms to wait, cuffed and hooded face down, cheek on the padded leather surface of the bench or a floor mattress. Her tight ass displayed exposed and vulnerable. Visibly squirming involuntarily on the enlarged phallic plug. She might similarly be left standing or kneeling facing the wall. Or perched anxious and uneasily on the edge of bench. Waiting for Him to arrive and command her.

The door might be left ajar or open so she could hear the hubbub from the lounge & knew she could be observed. Or closed so she waits in the loud silence for Sir. Her sexual funk growing by the second. This would naturally also always be the case hooded or not, gagged or not.

Inside the room, as outside the room, when sissy is serving Sir she was His to do with as He pleases, and she was to please Him perfectly and ardently, or be punished. The private room just added to her sense of  vulnerability and her sexual obedience to His pleasure.

 Waiting in vulnerable sexual fright for around 10 minutes or so, but to sissy it always felt much longer. She might already have Her own or another pair of soiled panties stuffed into her mouth, or she might be left ungagged. So she could cry out in fright when she hears Him arrive, closing the door firmly behind Him. When He arrives, enjoying roughly removing her pink satin panties to gag the sissy with.

Often we were never even allowed to see who were serving in this way, just hooded and led blindly to

one of the serving rooms. And not permitted to know who it was afterwards either. This was also very  popular with groups of  men. Fucking us urgently, roughly with lust, then dismissing us used and still sticky with their pleasure. Hooded, panting, breathlessly, hot in the closed hood, and led away by the Misses to hurriedly clean up and get back to serving. Blindly leashed through the public room so all the guests could enjoy our shame and the other sissies could see too, wondering if or when they might be next.

Due to the anonymous nature of this service. Sissy might not lick Sir or the Sirs clean afterwards, as she is normally expected to do. Cleaning and thanking Sir for being allowed to serve and clean Him, looking up from her knees. Or the hood might be partially undone, loosened and pushed up slightly so she can lick Sir clean, without being able to see His face. Most often though through a special glory screen in a side room or the toilets, by her or another sissy, called in to kneel and lick the Men clean. Often when licking the men clean in the room or through the glory hole, He might spurt a hot  extra splash of cum into sissies face, which of course sissy would thank Him for. She would  suck His shaft deeply and fully so He was totally clean. Which might also produce an extra spurt for of His pleasure for sissy. She need not necessarily wait or ask permission to swallow on these occasions, however she might be punished if Sir decides she should have done. Though usually Sir is very dismissive and not generally interested in punished sissy, deservedly or otherwise immediately after He has cum. He might though choose to tell one of the House Misses who would punish sissy.

The sissy who had served in the hood and so publicly dismissed. Led away as through the room, still hooded & in cuffs, disheveled and sticky, maybe still also without panties, as they were still in Her mouth. Was also very popular for public fellatio immediately after she had tidied and cleaned herself and her uniform, and breathlessly hurried back to her chores, lest She be punished for laxity, or dallying.

The sissy would curtsy & ask trembling how she could serve Him, as He fondled her intimately. She might be sent to fetch Him a drink, then put over His knee and spanked. Then on her knees as He opened His trousers  look up over His massive erect cock. To all sissies a real Man erect looks impossibly large, especially from her knees, where she should be before Him.

Looking up tearful & submissive into His eyes, wondering if Sir was one of the men who had only just enjoyed penetrating her ass. The remnants of whose thick cum might still be in her sticky panties. He would never tell the sissy adding to His pleasure of the moment and to her submissive service.

The Men who frequented these clubs and hotels often used special supplements so they could enjoy cumming multiple times copiously. And often being naturally dominant just had very high insatiable sexual appetites generally.

This also suited  the dominant Ladies. Mistress and the Misses also enjoyed this extra male vigour. The modern Woman expected satisfaction from sex.  From Her sexual partners boyfriends & lovers. And not unsurprisingly totally from Her sissies.

Sometimes if not frequently this increased sexual predilection from Her boyfriends was slightly bothersome to Her. She might summon sissy to serve Him, or send Him to sissies room. And sissy was always expected to serve Sir when required and to ensure to please Him perfectly. Often in the night Mistress might have a lover staying over. And when She was sleeping, Her lover might go and wake sissy for a nocturnal BJ or penetration. One game the Men liked to play was sneaking into where sissy was sleeping and removing her plug without waking sissy, so sissy would only wake when He was inside her. This was very difficult to do as sissy was nearly always attentive even when sleeping in case Mistress might want service. But the Sirs enjoyed the game. And sissy would have to pretend to be surprised and alarmed for His pleasure.  

More so than fellatio, being penetrated by Sir also had the highly desirable effect of making sissy feel even more needy and attentive to Mistress. And if sissy was in  any way deemed too bothersome, or too needy, a swift and usually satisfying if not enjoyable application  of the cane was perfect for that.

Sissy would also feel very needy towards Sir, even though also feeling used and shamed. And it was amusing to see Sir send the tearful sissy away with a dismissive slap on the bottom or backs of Her legs. And if sissy looked too tearful Mistress might send her for the cane too.     

Sticky panties might be changed immediately after service or not. It really depended on the preferences of the next guest. Or the house Misses liked to keep this random and unpredictable for the sissy, for their own amusement. Sex soiled panties are often swapped & licked clean, or used to gag another sissy. In any case there is always a nice little sticky pile, slimy and stinking of sex, left at the end of the afternoon for one of the sissies to hand wash and iron while the others are busy with other duties and getting ready for the evenings.

The evenings were often quieter. As most guests went out for the evening meal and entertainment. But

the sissies were kept very busy cleaning the hotel from top to bottom and were allowed some supervised pampering time to wash themselves, have an enema and clean their uniforms. Freshen their make up and hair ready for the when the guests returned for the night. Getting dressed in glossy satins and latex nightwear ready for the Sirs to choose for intimate chamber maid service

In the quieter seasons sissies might be sent out in the limos for parties and service in the clubs, to earn extra money for Mistress. But in the busy season there was just too much cleaning and preparing to do. 

Mistress of course loved to see us serving Her prettily both domestically and intimately in Her quarters usually in the late mornings and early afternoons.

We were often caned by Mistress at these times too as She often enjoyed punishing us for the slightest,

or imagined fault. If you were especially fortunate to be chosen you could serve Her in the evening and night time too, though Mistress often had one of Her boyfriends or girlfriends staying over at night. She loved the daytime service though, getting us ever so flustered & excited then sending us down afterwards to serve Her male guests. 

Mistress guest said we always had such lovely uniforms to wear. She satin so glossy and shiny. The maids uniforms so difficult to keep clean and perfect as we worked.    

With lots of ultra femme detail. Far too ultra feminine for any real Woman to consider wearing, but perfect for sissies and always finished off with a lovely apron to remind us of our place. And our chores so menial and domestic, far too demeaning for a real Woman to think about, but perfect for sissies. And performed so perfectly full of sweet sissy sexual obedience and in fright of Mistresses canes.

And it was so enjoyable for Her to see the look on our faces when we were sent for the canes or for the strap on. So enjoyable to hear our little muffled cries of pain or helpless arousal. Muffled by Her wet panties, that She just removed to gag us with them.

But it was so much better to be sent for the strap on than the canes wasn’t it sissy, Miss asked me sweetly.

“Yes Miss, thank You Miss.” I curtsied.

“You may stand and face the wall now sissy,  until we want you again.”

“Yes Mistress, thank You Mistress.” I replied obediently

“Curtsy cuffs and eyes closed sissy, your superiors have things to discuss.”

“Yes Mistress, thank You Mistress.”

Later when Mistresses guest had left I was sent for two cock gags and the canes. The two sissies were cock gagged, then caned and sent back to their chores.

I went with Mistress to Her bedroom to help Her choose an outfit, as She was going out to meet some friends and one of Her boyfriends later, so wanted something both classy but also very sexy.

Mistress always had so many lovely outfits to try on. And each  She tried on would need to taken to the

laundry room, hand  washed and ironed again. Everything had to be absolutely perfect for Her. Today because it was very warm She chose a pair of black leather culottes, that were very short so looked like shorts, and a matt silk shirt and strappy sandals. Mistress also usually liked to wear the keys to our chastity, even though She had no intention of ever unlocking us on a chain or necklace. Sometimes nesting in Her cleavage or an ankle chain. Today it was on a silver chain around Her waist.   

Then Mistress gagged me with Her freshly removed panties and also caned me. 6 with the thick rod like cane and 12 with the springy whippy cane. Mistress always enjoyed using the springy cane especially on the backs of our legs. She sat down and knelt me between Her thighs for intimate service. She climaxed loudly and strongly with multiple waves of pleasure. Then She followed me into the small washroom lit a cigarette and watched me hand wash Her panties.

Afterwards I helped Her dress in Her chosen outfit then was sent for another cock gag, for myself. I took Mistresses unwanted outfits to the laundry room then I was  and sent to work with the other 2 sissies. My plug was left fully enlarged as were the anal plugs for the other two sissies. We squirmed helplessly as we worked, our bottoms and backs of legs stinging and smarting,  and were constantly gagging and spluttering on the massive cock gags, that pushed deep into the back of our throats. I was also blissfully happy having served Her, hotly aroused and frustrated in my tiny chastity. My pink satin panties, always very small and tight felt even tighter and hotter today.

Later in the afternoon we would be taken downstairs by one of the house Misses. Hurried along with the

stinging crop on our still tender rears.

The Miss who came to collect us was amused to find all three of us cock gagged, in the stifling heat, and She made a point of parading us through the main lounge so all the male guests could see us, making sure we would be quickly selected for service. The other sissies glanced  at us with distress, making us feel even more shamed and humiliated.

Our time with Mistress both domestic and intimate making us even hotter and needy, ready to serve the male guests, it was going to be a long hot afternoon.

It was still mid afternoon and in the evening there would be lots of parties. Working hard and prettily. All the sissies sobbing with sexual fright whenever one of the men fondled us or we heard a loud slap on the bottom and the tearful ‘thank You Sir.’  and curtsy.

The men did enjoy slapping our bottoms as we minced past them performing our chores. We would stop and look over our shoulders with a little pout and squeal. Then curtsy, thank Him and ask sweetly if we serve Him. We would be blushing with hot shame. He might pull you closer and fondle you, the men often liked to feel our tiny locked chastity cages, just so they knew we were fully locked. Of course we always were but the effect made you feel very small and it was always very humiliating.  

Most of us had been effeminate chastity sissies for quite some time and quite  few seasons as sissy

chamber maids. But it always reminded us of that very first time, usually in a club accompanied, by your female superior chaperone, trainer or prospective owner. Serving for possibly the first time in a short maids uniform. When one of the men at the table fondled or slapped your bottom, felt and examined your chastity, either through your tight satin panties or His big male hand inside your briefs. When you looked up in alarm to your chaperone and saw the amused delight in Her eyes. And She told you to curtsy sweetly and thank Sir for His attention, and offer to bring Him  a drink or offer service to Him. On these first occasions it usually wasn’t intimate service but He may want you to kneel and polish His shoes, or to perch on His lap while He chatted with His friends.

Of course back then the chastity device would be a little larger. But the comment would be how tiny it was with the usual giggle from the ladies that it should be much smaller. Which in time it would be, with the hormone treatments it would so tiny and barely noticeable, to our superiors at least. Mistress might cane or spank you later, or right there and then for being so reticent and disobedient in front  of a superior. Or worse might get Him to spank you in front of everyone.

The guest may just want to enjoy the slap or to fondle you, then send you away to your domestic duties. Or you may be sent to one of the intimate serving rooms. Or fetch Him a drink and orally serve Him there in the room in front of everyone.

The real Men and some of the Female guests were very good at getting a loud & stinging slap, especially on the backs of our thighs where is would redden and smart terribly. And all the sissies would redden with shame and wince at the sound.   

One popular entertainment for the guests was coming into the laundry room in the morning when some

of the sissies were hand washing the female guests and Misses underwear, and fuck the sissy on a table

face down in a pile of panties or slips. While the other sissies in the room hurried on with their chores. Afterwards of course the sissy would be told to get on with her chores. But throughout the morning she would often find Herself summoned upstairs for fellatio with the other guests. So she would spend the morning working in the sultry laundry heat with sticky panties and  a sticky face and mouth. If Sir or one of the Misses hadn't told us to clean ourselves were not allowed to wipe our faces or uniforms until given permission. You would spend the morning hot and red with shame trying not to meet the other sissies furtive glances and them not daring, shamed to catch your tearful eyes for more a fleeting glimpse. The Misses would sometimes come in and tease us making us look at each other and whisper to each other how exciting it was for us sissies to serve the Sirs so obediently and be left soiled with His pleasure, while we worked.  Most of the Misses found these morning sessions fun & particularly entertaining and often took a break and came in to watch with a coffee and cigarette. Afterwards they would make sure that the windows & doors were firmly closed so that we would work in the sticky heat of the laundry and the stink of sex.  We were not allowed to slacken our pace at these times and often one or more of the sissies would get  a couple of stinging strokes from the crop to quicken our work tempo.

Mistress also made lots of money from online video of these sessions, as they were  very popular, and often the muffled cries of distress and dismay were also popular & sometimes streamed on sissy radio, as lessons for other sissies. The devoted house sissy maid or sissy wife busy at her chores waiting for Mistress, or Master to come home.

Wondering if the next time her owner went on a long vacation this might be her. Squirming with fright and secretly shameful arousal too. So secret that we never admit it even to ourselves and most Mistresses prefer to tease and hint, to torment sissy with her sissy desires rather than openly admit it.

Nearly all sissies now were kept in permanent chastity. The most they might experience is a emotional shattering anal orgasm. Sometimes when pegged or sometimes with Sir. Sissy is extremely docile and needy after penetration with or without such an orgasm. And even this Mistress usually kept under Her strict control.

Most sissies were no longer milked after the first few months in chastity It was deemed unnecessary and troublesome. And there relief after a milking sometimes led to a slacking in attentiveness, correctable with corporal punishment but not desirable. And if sissy wasn’t milked it added to her sexual frustration and thus her servility to her owner & superiors.

Sissies sometimes experienced a slight involuntary leakage. Especially with the deep urethral tube that prevented nearly all sensations down there. Not directly but they would become aware of the dampness in their panties. Waking in the night or if they were serving intimately, or during pegging. This was especially humiliating if it happened while serving Sir. But humiliating for sissy at all times too.

Mistress would laugh at the weak dribble of precum. and say it was to remind sissy of all the times they had masturbated without permission, when they should have been busy performing chores or learning how to make themselves pleasing to Mistress or Sir. And how perfect and appropriate it is that this was no longer allowed but sissy got to give Mistress an orgasm whenever She wanted one, or suck Sir on demand.  Sometimes sissy might be punished for these leakages or just teased and humiliated, Mistress liked to decide depending on how She was feeling at the time. 

The Misses liked to keep us very busy and very visible to the male guests, even when we were cleaning the individual rooms the doors were usually kept open and we were hurried along, often with the sting of the crop. That sharp crack of hard leather on soft flesh also hurried all the other sissies along with fright and as Mistresses often laughed a delightful sexual funk.  

We would always be more intensely aware of our overlarge phallic plugs at these times and squirm helpless on our  penetration with vulnerable fright but also helpless arousal too. 

Looking up from our knees obediently when He came in our mouths and all over our face. Swallowing obediently and prettily, hoping that Mistress and the Misses would, enjoy buying nice things and vacations, and  have a good time with all the extra tips we were earning for them.