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.