The Breaking of a Maid

"Kitti, you need to learn to walk like a girl, so today I will teach you. Try hard and you can avoid my cane, boi."

"Yes, Princess," I squeaked back.

"Walk back and forth. Slowly. Hmmm. No. You need to use smaller, daintier steps to walk in heels. Bend your knees less, sissy, but don't straighten them right up. That's it, good sissy. You see, you're a natural. Remember, heels are all about forcing you to walk in a showy, impractical way, a way that says "I am Kitti and I am a pretty little maid". Try repeating that in your head.

"OK, so you're moving a bit better now. Now, pull in your belly and push out your bottom. Better. Straighten your spine a bit. Now, chin up slightly, shoulders back. That's good, that'll show off your breasts more while improving your balance. Oh, Kitti, you're a natural.

"Now, imagine a straight line in front of you. Make sure you're walking along that line - bring your feet around in an arc and step as close to that line as you can manage. Do you feel your hips and bottom swaying? It looks so cute, sissy! You're really getting the hang of this. Now, put it all together and keep practising."

An hour later she let me stop. I sat on an armchair, my knees demurely together (as ordered) and watched one of her petmales enthusiastically lick her out right there on the sofa. When he had finished, she had him fuck the other petmale on the floor, and then had them swap positions. They did everything with no hesitation, no shame, no self-consciousness at all. They were as close to animals as I've ever seen humans be.

"Come, Kitti, let's have lunch."

I cooked for Princess Octavia in the kitchen while she read, and she had me eat 'with' her, right at the other end of the table. The guards kept a very careful watch on me, and two extra flanked me when I was chopping and cutting. They left nothing to chance. The meal was declared adequate but I was told I would need a lot of practice and to do a lot of reading to do that part of my work properly.

We went through into a parlour room and Princess settled down to read. She handed me a magazine to read and told me she thought I would like it, then she pointed me to an armchair and lost interest in me for a while. The magazine was for teens and young women, all tips about makeup, boys, sex and clothes. I was a university graduate, and the reading material was clearly chosen to show me my place was no longer to have higher thoughts.

Another round of walking training followed an hour later. Princess made me practise going back and forth, around corners, bending over, and standing still while being hit with a crop - which she handed to a guard. Every time I fell she awarded me a demerit, and my future punishment mounted quickly. I focused my mind and made a great effort to move like the sissy maid I was, and especially not to fall, but a few more demerits followed.

The real catastrophe happened in the evening. I had been trusted to bring Princess Octavia and Queen Seraphina a bottle of champagne, which I carried on a silver tray from the kitchen, through the long corridors, and into the same parlour where we had spent the afternoon. As I entered, Queen Seraphina hurled a dog-toy for one of her human puppies to chase and he clipped me as he ran past, breaking my careful balance. I panicked, overcompensated, and fell. The champagne and my dignity were both lost.

"Not good enough, Kitti. Not good enough at all. I'll have another slave fetch more champagne, but boisterous pet-slaves are part of this house and you have to work around them. No excuses. Guard, take Kitti to her room and put her to bed. Kitti, you may read one of the books I've left in your room for the rest of the night. Go."

The guard whisked me back to the frilly bedroom I was kept in, and she unshackled me through the barred doors once I was locked in. Princess had left me some trashy romance novels and some chick-lit, so I picked the one that looked the least bad and to my surprise I got quite into it. For a few moments I forgot the punishment that was coming to me.

Day 4

My diary will not record much about this day, save to say that I was chained up in the basement and then caned and spanked repeatedly. A typical conversation went like this, while Princess beat me with some new implement and I whimpered and cried.

"Bad sissy!"

"Sorry, Princess! I'm sorry!"

"I will tolerate no brattishness from you, boi."

"No, Princess!"

"This new bottom of yours isn't just for fucking and looking at, you know. It will also be reddened regularly."

"Yes, Princess."

"When you serve in our home, you will be constantly watching for problems and accidents, and actively avoiding them. You will think ahead, consider your next move. You might look like an airheaded cock-loving bimbo slut, and sometimes you'll be one, but really you need to be a bright little sissy to serve me well."

"Yes, Princess."

"These ten are for dropping the champagne, and the next hundred are for falls while sashaying."

"Yes, Princess."

"Count them..."

"Yes, Princess..."

That carried on for a while, then I would be left in pitch-dark isolation for an unknown time, before she came back and started it all over again. I learned she could be utterly, mercilessly cruel, and I learned that her words carried with them a great threat of pain and anguish if not listened to. Truly, she made an impression that day.

Day 5

We tried again with basic domestic service. I was dressed up in a pink frilly maid's uniform and both Queen and Princess referred to me exclusively as 'sissy' for the whole day. I think they wanted to knock some of the remaining maleness out of me, and my aching bottom was a constant reminder that they could back up their words with exquisite force.

I simpered, I sashayed, I curtseyed and I smiled vacantly. Everywhere I went I scanned for things that could knock me over or cause me difficulties, and a few times that saved me from another slip up. The petmales carried on their games around me, perhaps giving me just a little more space than normal, and the day passed without a major incident.

In the evening, Princess Octavia had something different in store for me. She sent me back to my room and told me to open the package on my bed, then put it on. Inside the brown paper was long stripey socks, a pair of pink pyjama shorts, and a pink pyjama vest with a rainbow across the bust. I put them on and returned to her, shackled again, in a small room dominated by a huge TV and couch.

I was made to sit on the floor in front of the sofa, on cushions. Princess sat behind me, on the sofa itself, and she wore white silk pyjamas that were far more sensible and less revealing than mine. I was given popcorn, even a glass of wine, then made to watch first a very girly romantic comedy that was nonetheless somehow entertaining, then another rom-com, then a short porno about a sissy maid being fucked by a big muscly hunk.

Princess masturbated on the sofa, but I was left locked in my chastity cage and not even allowed to look round at my owner. I heard her moan and whimper as the scene unfolded, then I heard her climax quite noisily as the film neared its conclusion. Between the film and the sex act going on behind me, I could only grit my teeth and try to bear the pain of my cock constantly thrusting against its prison.

My traitorous mind felt quite at home in the girly pyjamas my Princess had given me, and while I ached to be allowed some release, I did not fantasise about fucking her. I wanted her to fuck me, to take me into her bed and slip her strapon inside me, then make love to me while she jacked me off and let me cum.

I was acutely aware that while I fantasised about that, I had pictured myself in those same pyjamas Princess had put me in. I tried to overwrite it with me bare-skinned, but something in me rebelled. I could not forget that I had juicy breasts and curvy hips now, after the enforced surgeries, and it was hard to picture myself the old way when the new reality was so present every time I moved.

When Princess's orgasm was over, she sent me off back to my cell to get some rest. I flopped down beneath the pink duvet and got comfy; no one had told me to take the pyjamas off, and I didn't dare remove them without permission, so I fell asleep wearing the girliest and silliest set of clothes I thought I'd had yet, and I dreamed in a glossy rom-com style, except with my Princes as the lead character, who kept winning me over and then pegging me hard.

Day 6 - Pool Party

"OK, Kitti, it's time for a party! A pool party! Let's pick you something to wear."

Princess Octavia had a few friends who were part of the 'real scene' as she called it: slave-owners who all were participants in the criminal enterprise of taking and keeping other human beings. She had invited a few around and was most excited about the prospect of a pool party where I could be shown off. She and a guard were in my room, while I stood naked with my hands on my head.

"Hmmm, what will we have you wear, Kitti? What indeed? There are so many choices to make. We could go full maid but then I'm not sure you'd be able to swim. But we don't just want you naked, at least not straight away, because I think you know that you need to tease a bit first. I think we'll have to try on some costumes first. OK, let's see.

"Classic black two-piece, put that on. Well... No, it hides your cock too well, doesn't it? You actually look female with that on. I don't want my guests getting confused, do I? Everyone needs to be able to see what you are. Here, put this on, it's the skimpiest one there is. Oh, turn around. Hmmm, now, the g-string really brings out your bottom, but the front is too thin, too obvious, you can actually see the cock-cage poking out.

"No, take it off. Here, let's try something else. Here, a full one-piece. Oh, yes, that rather works you know. Your lovely little cock is so obvious at the crotch, and the demure look it gives you really turns me on. Take that suit off, try this one. It's extra frilly, you see. Now, then. Yes! That's it."

I offered no resistance and surrendered to the confident power of her singsong voice. I wore a red one-piece swimsuit with a deep cut for the cleavage, and sewn-on frills that went all the way around the suit in circles. You could tell just by looking that I had a cock in a chastity cage, for the lump protruded from beneath the crotch and the lines of the suit drew the eye down to it. I looked so girly, so young, wearing it. I blushed but there was nothing I could do to change things.

I served drinks by the pool as Princess Octavia's friends and their slaves filtered in. She had invited six close associates: five female and one male. They all arrived in possession of some slaveboys, some general-use, some pets, and a few sissies like me. I had to wear a pair of cuffs with a long chain, and guards were stationed all around, but I noticed that the other slaves were watched just as closely as I was.

So I was beginning to be trusted, then. It was clear to me already that I didn't have it in me to inflict pain and possibly death on another random slave. It was clear that I could not stomach doing that to another of these victims, and it was actually becoming quite clear that they all seemed to enjoy their lives with our owners. The slaves who were visiting us were the same: happy and anxious only to please.

All of Princess Octavia's friends took a chance to inspect me. I stood still while they fondled my body and I didn't object when they exposed my tits or got my cock-cage out from under the suit. I was fair game for them, I had been told, but I wasn't going to be allowed to service them sexually.

A game of sissy volleyball was set up, and four of us played together under the hot sun. All of us were short slaves, all quite young, and we all had the same implanted breasts and altered hips and bottoms. The boi called Flower wore a 1950s-style one-piece that suited his plump build, the boi called Poppy wore gold shorts and a matching halter neck top, and the boi called Sweetheart wore only a white g-string. His small tits didn't need as much support as the rest of us.

All of us made high-pitched squeals and yells as we dashed around the volleyball court. Our owners egged us on, already a little drunk, and promised rewards for the team that played the best. We all knew what that meant: the team that made the best show of being sissies playing sports.

In my mind, I made a box for my shame and closed the lid. I pranced across the court, leaping in a way that would show off my bottom and breasts as best I knew how. I pirouetted, I scampered, I moaned when I hit the ball, and I made sure to always stand with my bottom thrust out and my cleavage on show.

The other sissies gave it their best too. Not one of us ever dared try to act like men. We tottered, we squealed, and we made a display of ourselves while the rest of the party looked on. The match was close - none of us had much skill at it - and by the time we were finished we were all hot and tired.

"Sissies, take a break together. Have a drink - just one each - and swim if you want. Kitti, you can keep your hands unbound for the time being, and the four of you will have the pool to yourself."

I was given a pink cocktail and I drank it down quickly, then I followed it up with a glass of ice-water. Poppy went into the water with Sweetheart, and the plump sissy called Flower sat next to me at the pool's edge. He shuffled next to me until our bottoms were touching, then he downed his drink and started to talk to me.

"You were great out there, Kitti," he said in his sweet high voice.

"Thank you!" I sang back.

"You've really got the way of moving down, you know. How much did you practise before you were enslaved?"

"Never, really. I just tried it out in private a few times."

"Get out of town, honey,"

"No, for real. I'm still learning as I go."

"You're a stone-cold natural sissy. I bet you even kiss like one."

"Huh?"

"Do you like me?"

"Sure I do," I replied. The alcohol was loosening me up.

"Do you know we're allowed to fool around?"

"I know - Princess said."

"Why not then?"

"I mean ... OK."

His plump lips were soft and warm, and his tongue was lithe in my mouth. We heard wolf whistles and claps when we kissed, but we didn't stop. I slid my hand around his waist, and he put his on my thigh, then slid it up. I realised he was showing me how to touch like a sissy - softly and teasingly, so I let my own grip loosen and used my nails to stroke him. He purred.

We went into the water together and continued our heavy petting. I let my self-control go and surrendered to the first real intimacy I'd been able to feel in a long time. At some point, Poppy and Sweetheart got in on the act, and then we were all together in a clump of bodies. I got to know every curve and fold they had, and they found mine. We all were soon dry-humping each other, pressing our caged cocks into each other's bodies, and quite forgetting where we were.

Some time later, I was back serving Princess Octavia. Under the gaze of a guard, I covered her back with suntan lotion, and then I was made to lotion her front too. I gasped when I covered her breasts with the oil - my cock was trying hard to escape the cage that held it and the pain was hard to cope with. She laughed when she saw what was wrong.

"That's OK, Kitti. Your little thingie must have been really suffering today, huh, sissy?"

"Yes, Princess!"

"Well, let's see what we can do about that. Who wants Kitti to cum on their feet?"

"I do!" said a curvy, short girl called Sylvia - she owned the plump sissy called Flower. "But, I want him and Flower to kiss for me while they both jerk themselves off. Come over here, darling!"

We were both unlocked from our chastity cages, and made to kneel in front of Sylvia's sun lounger. Flower leaned over to me, and there was a spark between us when our lips met. We both started to jerk our cocks towards Sylvia's feet, as she lay there looking down at us. I closed my eyes and just let the feel of someone else's lips on mine push me forward.

Flower came first - he was less inhibited than I, and he had just as much need as I did. His seed spurted over his owner's feet and she giggled at the sounds that Flower made when he orgasmed. I saw that he had cum and then I looked into his eyes and saw the lust that still burned there. Lust for me.

That sent me over the edge. I climaxed onto Sylvia's manicured feet and then I whimpered and moaned as more waves of the orgasm rose up through me. I tried to push away how aroused I was, because to admit that was to admit that I was enjoying that day. I thought instead of how I needed the release because I was under great stress, but I could not quite believe it.

"Good boys. Puppy! Come here and clean me up," cried Sylvia.

One of her petslaves answered the call and licked up our mess from her feet, then he bounded back off to play with the others of his kind.

"Does he give blowjobs yet, Octavia?" asked the male slave-owner who was attending.

"Not safe yet, Horatio. But you can fuck him if you like?"

"Yes! Come here, Kitti, and kneel down on all-fours at the poolside."

Horatio had come prepared. He rolled on a condom and lubed me up, then he slipped his long, thin cock inside me with an audible moan. I was still wearing the swimsuit, he had just pulled it to one side to get access to me. I realised I hadn't even thought about disobeying, I had just gone along with it and got right in position to let him take me.

I whimpered with pleasure as he fucked me. He was a good lover, quite gentle, but he held my hips with a firm grip that had real strength in it. He was obviously enjoying himself immensely, and it took him little time to reach his climax. His thrusts had been careful, and he had said not a word to me the whole time, so I gave silent thanks that he had been invited.

In the end, Princess let all her guests fuck me by the poolside. I was made to shuttle between sexual service, fetching food and drink, playing with the other sissies, and resting. The last of the guests left just before sundown, and I ate a big meal in the slave-kitchen before I was put to bed. I collapsed into the sheets, and was unconscious in seconds.

Day 7

On the seventh day I dressed in a standard black and white sissy-maid's uniform while a guard watched me through the cell door. She waited while I rolled on my fishnets, slid on my black satin g-string, then shimmied into the little dress and raised its skirt to expose my chastity cage. I quickly applied makeup and finished the outfit with a glossy black wig in a classic bob, and a pair of shiny black heels.

When I got to the barred door of my frilly room, the guard arched an eyebrow, and I remembered how to greet a superior. With a sudden blush flaring on my cheeks, I curtseyed to her and made sure I lifted my skirt high enough to give her a good view. A thin smile crept across her face, and she beckoned me to turn around.

Through the bars, she first cuffed my skinny wrists and then buckled a ring gag into my mouth. I was far too scared of her to risk a bite, and she had to coax me to close my mouth around the metal. With it in place, I had no way to close my mouth or use my teeth at all. The cell door swung open on its well-oiled hinges, and she led me through the mansion to a bedroom.

It was a red room - red velvet and red silk everywhere. On the red-sheeted bed lay Queen Seraphina and one of the guards, both quite naked and enjoying each other's company. My Queen's dark wavy hair glowed with a fine lustre in the sunlight that came in through the big open window. On the floor were two petmales, both quite young - one belonged to the Queen and the other to the guard.