The Breaking of a Maid

"Capital, thank you for bringing him. Good morning, sissy. I know your hands are cuffed but please try to curtsey anyway, for I will not be denied respect. Good sissy! You already do it like a proper sissy-slut. Tell me, did you use to practise that at home? What, cat got your tongue?"

"Seraphina you are a cruel woman!" said the redhead guard who lay with her on the bed.

"Why have a sissy if you can't have a little fun with it? Well, sissy, you're mine for the day and it's time for your training to get more intimate. Before I let you loose on my daughter's private parts you will need to satisfy me and a team of helpers that you pose no threat to her, or to us. We will start with your gag on, but if you perform well enough, we'll let you graduate to gagless.

"One little warning, sissy. Your mind, such as it is, must play the part as well as your body does. Sissies are not known for their high intelligence or searing intellect, and I would have preferred a sissy with less education than you. I need to see it in your eyes that you are an empty, pretty shell who lives only for his superiors' pleasure. Can you manage that? Good boi. Well, come on over to the bed and lick my pussy then. I want a nice long warmup before you make me cum."

The guard holding me let me go, and I tottered over towards the bed. In terror of Queen Seraphina, I tried earnestly to follow her orders, fixing a grin around the ring gag and trying to smile with my eyes. I fluttered my eyelashes at her and she laughed, a big booming laugh that announced her pleasure in her triumph.

Moments later I lay on the bed and shuffled into position to get between Queen Seraphina's plump and curvy legs. I moved up to her thick dark bush and wriggled around until I was in just the right spot to reach her with my tongue. My hands remained locked behind my back, and I had never heard the guard leave. From behind me would be a great view of my bottom.

I didn't even realise I'd started licking Queen Seraphina for a few moments. Her pussy had been near my face, and like a good mindless sissy I had simply started licking. I stopped for a moment to gather my thoughts and she gave a warning growl, so I redoubled my efforts. That brought another warning to slow down, and I remembered her instruction to tease.

"Sissy, look up at me with those big pretty eyes while you lick me. Empty your mind of whatever little thoughts you were having about bows and kittens and focus on me. Show me your keenness, show me your adoration, show me your single-minded simplicity. Good girl! Sorry, boi! That's it, sissy. Big round eyes. Good!"

Through the ring gag I snaked my tongue up and down her slit with long slow strokes, finishing with a light flick across her clit that made her smile. I gazed up at her and tried to replace fear with adoration. She was curvy, sultry and beautiful, like her daughter, and her dominance spoke to me in my gut. I could not help but fear her, but I made a little space in my mind for my attraction to break through. It worked and she saw it, then nodded.

I worshipped her hairy cunt as the morning stretched on. Sometimes she looked down at me and sometimes she looked to her lover, who still lay beside her in the bed. I was spanked by the guard behind me a few times for averting my gaze or 'looking too clever', and I blanched at the reminder of my status. Nonetheless, I felt my caged cock swell every time I made sissy eyes at Queen Seraphina.

"Good boi! Oh, yes, good sissy. Now, focus on my clit and make me cum. Keep looking up at me, yes, like that. Big round eyes like saucers, darling, that's the way. Sissies aren't often my thing but you're just delicious aren't you? A pretty flower just starting to bloom. Uh huh! Oh! Good sissy! That's it, right there."

More flicks of my tongue across her clit followed. She enjoyed a slow, heavy motion that spent a long time in contact with her button, and I gave her what she asked for. With my eyes wide and my mind as empty as I could get it, I licked on and gazed at her. She nodded vigorously then gasped and threw back her head, but she snapped her eyes back down onto mine and came and came while our gazes met.

Her eyes blazed with power and I saw in them the absolute assurance of a woman who knows how to own a man. Or, indeed, how to own a boi. Her pussy pulsed as she orgasmed, and I licked across her clit with the same slow pace I had used to start her climax. She beamed, a real smile, and bit her lower lip until finally her climax subsided.

"Good sissy. Here, I'll give you a little energy drink through a straw, then you can rest a few minutes. My lover here is eager to feel the caress of a silken sissy tongue on her clit, and you are going to oblige."

Perhaps ten minutes later, the guard decided it was time for me to start. She was an athletic redhead with blue eyes and short hair, and she had long powerful legs that led up to a neatly trimmed landing strip of red hair on her vulva. She had me wriggle over to her on the bed and got me nestled in between her legs, then she started to talk and did not stop.

"That's it, boi, just lick my clit nice and slow while you give me one of your patented sissy stares. Yuh, yuh, just like that bitch, just like that. You're just another little slave for us to use and abuse, you know that? You look real pretty in that dress, bitch, real pretty. You know I like a sissy around the place, it adds class. You're a classy bitch in that fancy outfit, you know?

"Good boi! Good boi! Lick me faster now, boi! You know, Seraphina, he obeys like he's been trained for months, you picked a good one here. Easy peasy to break a boi like this. He'll fall into line in no time. Look at me, sissy. Look at your superior. Maybe you think I'm just an employee? A six-figure a year employee with slaves on tap, ha! More than you ever made.

"Get that face nice and vacant again for me. No shame in a little jealousy but you can't get distracted from my clit, you know? Yuh, like that. Uh huh. Oh, he's good. Reminds me of my first ever girlfriend, she was a little nymph like him. Maybe I'll call you that as a nickname, little nymph, I like that.

"Keep licking your Master, little nymph. That's what I am, a Master. I own two pets and they don't have mistresses, they have masters. One's out training with another guard, one's down there on the floor, waiting to serve me. Mind even more vacant than yours, he has. Creature of instinct. Broken. Like you'll be.

"Little nymph, lick me faster now. Good little nymph, like that. I'd love to have you come clean my quarters sometime like a good maid, really get it spotless and shiny. I need a sissy touch in there. Oh god you've got a sissy touch, haven't you? You lick clit so good you'd think you had one of your own, boi.

"Yus, yus, lick my clit with that pretty tongue, boi, that's how I like it. Even faster still now, I don't like to be teased for long. Make me cum, baby, make me cum. Yup, yup, like that. Oh god look at those big sissy eyes of yours, they're, they're heavenly. You're so pretty, boi. Such a doll. Such ... a ... pretty ... doll ... oh! Oh! Oh! Yeah!"

She came hard and I got my face right into her vulva to keep her going and going. She grunted and I kept on licking her; her grunts picked out the waves of her orgasm and she got louder and louder. I heard her bellowing even when she wrapped her legs around my head, and I tried with all my strength to coax the maximum climax from her writhing body.

"Good doll, good sissy," she said when she was finished. "Will he rest now?"

"In a manner of speaking. Sissy, you will serve us as a living tray while we take some champagne. Another guard will be along in a moment - ah, come in! - and you may kneel next to the bed with the champagne she has brought us. The tray attaches to your collar and your cuffs, just about turning you into living furniture. Now, my love, shall we have the pets play?"

"Yes, please. Boys, go for it."

I knelt and tried to concentrate on keeping my balance. In front of the bed, in several metres of room, the two pet-slaves who had lain silently all morning sprung into life and began to wrestle each other. Neither was in chastity, and soon each sported a significant erection. I cradled the champagne while the pet-slaves vied for position - though they raced around the room, they gave me a wide berth.

They were so thoroughly animalised it was scary. For me, I mean. They appeared to be enjoying themselves immensely as they ran into one another, rolled, tried to pin, rolled more, licked each other and barked out their enjoyment. The pets kissed and bit each other, not hard, more of a love bite, as they writhed together.

Queen Seraphina and her lover sipped champagne and enjoyed the show. I realised I had been switched off - expected to remain in position and do nothing, think nothing, be nothing. Nothing except a sissy tray stand. I shook a little at the realisation but the bottle slipped and I had to breathe in carefully to right it. From that moment on, I always had one eye on the tray.

The women drank the bottle between them while the pet-slaves fucked each other. The males had raw passion aplenty, and they wrestled and rolled from position to position while they took turns to take each other. Each had small balls and slim cocks, and they had no trouble penetrating one another without lubrication. Each howled with joy when they orgasmed. Each presented their cocks for caging without rancour.

"That got me worked up again. Time for more sissy?" said the guard on the bed.

"You first."

"Can I remove the gag?"

"I think so. Sissy, you will be tortured to death if you ever bite any woman or otherwise harm her with your mouth while you lick her. To death. That will also result in the random death of one other slave through the bomb collar system, so think on that. You may choose from eager obedience or brutal torture now, so choose well. Imagine how pleased my daughter will be once you earn the right to lick her. How do you want him?"

"On his back so I can sit on his face and look at his little package through those knickers. I just love to see a boi's little pink thing all scrunched up like that."

"I know just what you mean. Facesitting for me too."

They used me as a sextoy the rest of the day. I started on my back, with my legs spread wide so they could admire my imprisoned member and the way I wore my knickers and stockings. The guard came quickly, and even Queen Seraphina could not keep herself from a climax for long. In my nostrils lingered the scent of their pussies while they rested, then after a little food they came back for more.

Queen Seraphina had me lick her while she stood above me, and her lover used my tongue while I knelt at the foot of the bed and looked up at her. In the evening, I tired, and they took me across their knees, pulled my knickers down and spanked some motivation back into me. With tear-streaked make-up, I gave them one more orgasm each, before finally they were done.

"Well, lover, what do you think?" asked Queen Seraphina.

"He's not as good as my pets, but he's passable and I think he shows real signs of breaking. The way he gazes up at you, you could almost believe he'd been sissified years ago."

"Perhaps his mind always was."

"Could be."

"I found his skills acceptable and his devotion adequate. He will be granted licence to worship my daughter after a few more days of faultless obedience and willing submission, but only if he can be the best sissy he is able to be. I will be watching and judging. Now, Kitti, it's time for you to go back to your quarters. The guards will be along in a minute."

Just like that she dismissed me. I felt like a tool being put back in a drawer, and when I got back to my cell, I showered and ran over the day's experience. I had been so willing to pleasure those women that I practically had lost my mind. Not like going mad, I mean. My mind had just been absent, not there, waiting to be required and happy to drift along. My only thoughts had been earning a chance to serve Princess Octavia in the way I craved.

I put on some pink silk pyjamas and got into bed, then I read trashy teen romance novels until someone brought me a large meal. That eaten, I returned to the romance novels and willed myself to enjoy them. A while passed and I got into the stories, really caring about which girl went with which boy and which dress got bought for which dance. That night I dreamed of dating my Princess.

Day 8

Finally, I was awarded a day of rest. Princess Octavia came by my cell and told me I had the day off, then ordered me into a cream silk cami top and matching shorts for the day. I picked a blonde pigtailed wig to wear with it, and she blew me a kiss through the bars when I put it on and showed it to her. Then she left, and I missed her. I actually missed her, the woman responsible for my kidnap, my torture. I ached not to see her.

Resting in my cell was different from any other rest I had ever experienced. I had so few choices about how to spend my time that I had no trouble choosing between them. Soon I was settled down with another trashy romance novel, which I read cover to cover. After that I booted up my tablet and watched one of the romcoms on it, and after that I read more.

Some time late in the evening, I got out of bed and looked at myself in the full-length mirror. You could barely tell me from a girl, even with the suggestion of a chastity cage beneath the shorts. I had a nice curve to my hips and thighs from the plastic surgery, and my breasts were perky and bouncy. I wobbled them around and giggled.

I looked hot. Genuinely hot. I experimented with pouting and blowing kisses and found the display much to my liking. I wiggled my hips and shook my bottom, and watched as the round, juicy flesh rippled and swayed. Even my toes and feet looked better, for they had been nipped and tucked and generally feminised.

I thought about Princess Octavia a lot, but my caged penis always throbbed when an image of her crossed my mind. I lusted for her and about her, but in every mental image of us together, something strange happened. I started as my old self but quickly became a sissified version, tottering, sashaying, and above all, obeying. That night I dreamed of her and all the ways a maid could serve her.

Day 9

In the morning I put on a maid's uniform and walked three of the petmales around the grounds. There were high fences all around the many acres of land that the women owned, and thick lines of trees and bushes that shielded us all from view. A geo-fence and some clever defences were apparently deployed around the place, to keep out any nosey drones, but the house was a long way from civilisation. No one would ever see us.

Those pet-slaves were always happy to go outside. They seemed to think and act like dogs, but with the sexual skills of human beings - they were often called on to lick pussy or arse. They scampered around, barking and whining and jumping and rolling, and I had a hard time keeping track of them all. At least I'd been allowed to wear flats to walk them.

I took them on a long loop of the grounds, going out as far as I dared to make it back by the deadline I'd been set. The long walk gave me time to think. My new life appeared to be the only choice I had, other than death. My main owner, Princess Octavia, was both a beautiful goddess and a great threat, though that only if I disobeyed her. She was an astonishing, powerful woman, and I was drawn to her.

Queen Seraphina seemed to seldom care about sissies one way or the other, which explained why she didn't keep an extra around. So, I was mainly the property of Princess. How quickly I'd come to think of myself that way - as a piece of property. I didn't think I had broken, not fully, but I knew that Princess and Queen had gotten into my mind. Could I get them out? Could I stop their progress? Did I want to? I never found a final answer on that walk.

When I got back to the house, I was taken down to the basement and found there four slaveboys chained to a wall of the dungeon. They were not gagged, nor blindfolded, nor being punished in any way I could see. Each of them had had their cock cages removed, and they all already stood with erections. Princess Octavia stood with them.

"Surprise, sissy! It's high time we trained you to suck cock properly, Kitti. Those pretty lips of yours aren't just for pouting, you know. Come over here and get on your knees, sissy. Right where I'm pointing. Your task today is to make each of these slaveboys cum twice. In your mouth, to be precise. In future I'll teach you how to take a load on your face, but for now let's focus on the basics. Oh, and remember you always, always have to swallow.

"OK, Kitti, let's start with slaveboy number one! Given that I know you're a true little cock slut, I expect enthusiastic cocksucking right from the start. Get it in your mouth and start sucking on it."

I knew this was a threshold and that crossing it meant I was already most of the way to becoming the sissy she wanted. I couldn't see a way out. I had been shackled again, there were guards all around, and we were already in the dungeon. Better to enjoy it, if I could. I looked up at the slaveboy and smiled, then slid my lips around his cock. He gasped when he entered my mouth.

"Good sissy. A mouthful of cock really suits you. Now, keep your teeth off his shaft, and practise taking him back and forth into your mouth, as far as you can get it. I started you with a smaller cock so it'd be easier. Slaveboy number four might be a real challenge!"

So just like that, then, I was the kind of sissy-slave who sucked cock and enjoyed it. The slaveboy groaned and whimpered, and I used my tongue to tickle the tip of his shaft while it was inside my mouth. He jerked his hips and drew in breath, then he groaned some more. He looked pretty young - twenty or so - and he had a boyish charm I liked.

"Kitti, you are a real cock slut aren't you? Good sissy. Put on a show for me. Get that boy off."

I sped up, and used my hands to grip his hips and steady myself. I used my slim arms to move my body faster, and rocked back and forward on my knees to really give my mouth some travel. The boy whimpered and shuddered - he must have been in chastity for some time, or else simply horny all the time - and then he sighed and went still.

Cum spattered around inside my mouth and coated my tongue. I recoiled a little and remembered myself, then I rallied my self-control and pushed my mouth all the way along his shaft as it spasmed more and more. I swallowed, to make room, and he came a little bit more, then finally stopped. My tongue licked away cum as he went flaccid, until finally he was clean and I drew away. It had been, at most, three minutes.

"My goodness, Kitti, you are a natural and no mistake. Well, onto the next one, then, sissy. This is one of mother's general service slaves, he doesn't actually have a name, and as you can see he's already quite hard. Mother likes this boy and the one stood next to him to perform for her - she only has bisexual slaves, you know?

"Anyway, get your mouth around his cock now, sissy. Good boi. So eager to please! Good, now suck. Hmmm. Yes. You see, not as much reaction. You need to use your hands a bit with this one, sissy. Get them around his shaft and balls and play with them. Ha! Not so hard, more gently. He winced then. See, that set him back, so now you have to suck him hard again."

I let a few tears escape my eyes as I got the boy hard again in my mouth. He was attractive enough, with light muscles and dark eyes, but I had started to feel like a piece of meat there on the floor. Him going soft in my mouth shamed me even further. I focused on the task, caressing his balls and shaft with my hand and listening for his whimpers to guide me.