The Breaking of a Maid

"Doesn't he just, mummy? He's perfect. Sissy, pull your knickers down and lift up your skirt."

I hesitated. The casual nature of the order, her carefree tone, they just didn't connect with the thing she'd told me to do. She wanted me to just expose myself right there and then, like it was nothing? Like all these other slaves were exposed? I couldn't do it. Octavia - the 'Princess' I was supposed to serve, raised an eyebrow and tutted.

"One demerit. Knickers, down, now, or I'll fry your balls."

I gulped down air and realised I had no choice, so I yanked them down and then moved my hands up out of the way. The women - my new owners - got up and came over to me. I had a security guard on either side of me, and they each grabbed one of my elbows and held me firm.

Octavia was thin, with small but firm breasts, beautiful eyes and a mesmerising smile. She was a little taller than me, even in my heels, and she had elegant long legs. Her mother was shorter, plumper, but the resemblance between their beautiful faces was unmistakable. Where Octavia glided around, though, her mother stalked and stomped.

My balls were inspected, my cock-cage checked for tightness. They squeezed my breasts and made me squeal, then they laughed at the high-pitched tone I used to exclaim. The tone they'd given me surgically. Seraphina admired my dainty feet and fingers - unaltered - and Octavia squeezed my bottom.

I blushed at being so objectified. They didn't stop. Every part of me was scrutinised and judged, and they seemed delighted with 'the way I'd turned out'. They kept my knickers pulled down for a few minutes, and I was acutely aware of every waft of air and fleeting glance at my smooth, caged privates. I knew at that moment that I really was a slave.

"Knickers up," said Octavia, "and listen well. You've earned two demerits so far, which any of the other slaves would tell you is bad going this far into the day. If you want to stop earning them, follow any and all orders given the moment they are issued. We are your absolute superiors and you belong to us, and quite frankly you will learn to be a good little maid one way or the other.

"Our previous maid took the only other way out available: walking out to the perimeter and setting off his bomb collar. It caused quite a mess. And we lost one of the pets, too. Confused? Sorry, yes: your collar is paired with another of the slaves, at random, each day. That includes my father, who is perfectly expendable. If yours goes off, or the other's goes off, well, the paired one activates too. Choosing to take your own life means you're eliminating one of them too. Think about that if you get tempted.

"You will of course enjoy your life with us immensely once we break you and you accept your new role in this household. I've read all those things you wrote, so I know you desire the chance to serve powerful women like us in just the way you've been altered to. Admit that you wish to be our little simpering sissy maid, and we'll take great pleasure in each other's company. Resist, and we'll punish you. Understand?"

"Yes, Princess Octavia."

"Good. You will break in around two weeks, slave. I guarantee it. For the rest of the day, remain silent, and follow me around to see how I live. Come, I'm going to start the day with the pets."

I gathered that neither of them worked - the women who owned me, I mean. They both lived lives devoted to whatever pleasures they desired in that moment. Two security guards came with us wherever we went that day, and we went all around the mansion and even out into the grounds a little.

Octavia peppered comments to me and about me throughout her day. She started by going down to the mansion's huge basement and uncaging a new petmale who was being trained there. Two more security guards flanked him, but he was chained and muzzled in a way that already rendered him quite helpless. Octavia made him roll over, beg, jump and 'run' just like a pet, and she laughed and giggled as the boy did his best to obey her. He looked nineteen, twenty perhaps, an asian boy with a small cock.

Octavia and her mother had slaves of every race and every build. I was the only sissy, but there were slim boys too, and I saw a slave of one of the guards wearing a dress, in the distance. When Octavia was finished with the pet-slave, she handed him to a guard to keep training then went for a swim. I was made to sit by the poolside on a sun-lounger, to take the weight off my aching feet for a while.

After lunch, Octavia had a blindfolded slave with a big cock fuck her until she climaxed, and then she sat on his face so he could clean her up. She took another orgasm from him like that, then she put on a strapon and fucked the boy until he came. He thanked her so fulsomely, so sweetly, for that privilege and she basked in his adoration before sending him back to his cell. I spent the whole time trying to resist getting painfully hard in the cock-cage.

Next, Octavia read for a while, then she had a pet-slave lick her to an orgasm, and then she ate an evening meal with her mother. Once more the display had made me horny, jealous even. During dinner, I waited in the corner, then was fed quickly by a guard once the two owners were finished. With my hands still chained to my waist, I couldn't even feed myself, and I was glad they didn't make me eat from a bowl on the floor like the pets did.

Octavia had me brought through into a soundproofed room when it was nearly time for bed. I was strapped down to a spanking bench and my knickers were removed, then shoved into my mouth. I tasted the precum on them and knew that I had been aroused most of the day, and I felt the ache in my balls from not being able to climax.

Those thoughts were blasted from my mind when the cane hit my bare bottom with a whistling crack. I had earned two more demerits for poor obedience, and that meant forty strokes of the cane, which Octavia gave me quickly and without preamble. She laid into me hard, and I wept freely at the pain and the humiliation.

I stumbled back to the cell, in the company of Octavia and a guard. They locked me in the room then reached through the bars and undid the shackles that held my limbs. While Octavia watched, I was told to undress, clear off the makeup, and remove the wig. Octavia made me find a pink, floaty nightgown into which the word "Sissy" had been embroidered and put it on, then she made me come up to the barred door and curtsey to her to say goodnight.

That one curtsey sent a rush of blood to my cock, then to my head. There before me was a beautiful, dominant princess that I would spend the rest of my life serving, and curtseying to her had felt so easy and so right. She beamed at me and told me to rest well, for the next day she planned to show me how sissies took cock.

Day 2

The next morning two guards woke me in my cell. I ate a quick breakfast they provided, then I showered and returned to the pink frilly bedroom that I was to live in, for the rest of my life. I had little time to think about that fact, for the guards made me dress and they didn't wish to be kept waiting. When I hesitated to follow any order, they would deliver a short, sharp shock to my balls.

Under their watchful gaze, I was made to put on a pink frilly dress with a floaty lace underskirt, pink ruffled knickers, pink stockings, pink heels, pink lipstick and a pink wig. I was shackled again, then led down through the mansion's stairwells until we reached a dungeon in the basement.

Waiting for me there was Princess Octavia, who sat on a leather-upholstered throne in the middle of the room. To either side of her were her pet-slaves, leashed males who lived on all-fours, who yipped and yapped when I was brought in. The room we were in was wide, spacious, and the decor mixed elegant but dark furniture with cages, paddles, chains and whips. I was forced in front of the Princess, then made to drop to my knees.

"Good morning, sissy. Did you sleep well?"

The question confused me for a few seconds, until I realised that I really had. Some combination of exhaustion and finally discovering my fate had let me sleep soundly, for the first time since I'd been captured.

"Yes, Princess. Thank you, Princess," I replied, choosing my words carefully.

"Good boi. That's B-O-I, by the way, you're a boi with an i. Or I might call you sissy, as well. Do you know, slave, that I have a name all picked out for you already?"

"A name?" I said, confused. I had a name.

"Of course, sissy. You need a proper new name to replace your boring old male one. You didn't seriously think I'd keep calling you that, did you?"

"I ..."

"Hmmm?"

"No, Princess."

"Good sissy. Now, sissy, for today's entertainment, you're going to get strapped to that padded bench over there, and then I am going to fuck your beautiful bottom with my strapon. Then my mother is going to fuck your beautiful little bottom. Then, my slave-father is going ... you guessed it ... to fuck your beautiful little bottom.

"You can't be trusted not to bite, and you can't be trusted even to suck a slave-cock, so we'll get a nice big ball gag in your pretty little mouth, and then you'll be lubed up and made ready. Oh, how cute, you're actually struggling against the guards. That's a demerit, by the way. I think I'll fuck you then cane you, sissy. Ah, good, I see you remember last night's punishment still. Chain the little slut down to the fucking bench now."

I tried to wrench myself free of the guards' holds as they pinned me to the bench, bent me over it, and buckled me down to it. It was useless, a purely futile and instinctive gesture, and in short order I was unable to move my arms, legs and back. My bottom was thrust out backwards, at just the right height for someone else to take me from behind. Princess Octavia disappeared behind me.

I craned my neck back to watch what she was doing. I could just see her, fishing around in a cabinet for a strapon, which she pulled out with a flourish. She returned in front of me, and she stripped off her clothes until she was completely naked. Her eyes sparkled, while mine shone only with fear. She shimmied into the strapon and I watched her ease part of it inside her, then she went behind me again.

"You've fucked girls, haven't you, boi?" she asked.

I made an emphatic noise around the gag and nodded.

"So you know what they sound like when they get fucked?"

I nodded again.

"Good, try to emulate that kind of moaning and whimpering while you are taken today. Who knows, it might even help you enjoy it. Now, let's get these very fancy knickers down and get you ready for some nice big cock. Not too big, you know? But certainly big enough for your little boi-pussy to really feel it. A little lube, and there, you're ready to lose your virginity. Awww. So sweet."

I shook so hard that my restraints rattled, and a few tears streaked down my cheeks. Through the gag, I tried to beg her not to do this, to let me go, to forget I had ever been in her home. She laughed a beautiful, high laugh and ignored me. I felt her line up the tip of the strapon, then she paused for a moment and took a deep breath.

"Here we go, sissy."

I tried to scream when she entered me, and then I think perhaps I blacked out for a few seconds. The next flash of memory I have is of her thrusting her strapon in and out of me, slowly and gently, so I could get used to it just a little before I was taken properly. It was unexpected, and I actually welled up with gratitude to her before I realised how absurd that was.

"Good boi, good boi, take it for Princess. Good boi. Oh, your little hole is hungry for cock, Kitti. Oops! That just slipped out. That's right, sissy, your name is going to be Kitti from now on. It's cute, huh? Just like you. Kitti, Kitti, Kitti, I'm going to love saying that. Oh, and your bottom? Delectable. You're a great fuck, Kitti. A really great fuck."

I was chained to that bench for the rest of the day. Princess Octavia fucked me until she came, and then she fucked me again when she'd got some breath back. She took a cane to my backside to punish me for my earlier disobedience, then she left me under the watchful but silent care of the guards.

Her mother arrived a while later. I watched Queen Seraphina get naked and saw how she resembled her daughter. They had the same dark hair, the same piercing dark eyes, and even the same lines of slight curves around their bellies, hips and bottoms. My Queen put on a strapon of the same size that her daughter had worn, then she thrust herself inside me.

"I see you're already a little opened up, Kitti, that's good. We'll be graduating you onto bigger cocks in no time, little one. And my my, in that small pink chastity cage you really are a little one, aren't you? I do so like for sissies to have little balls - it means there's less fight in you, did you know that?

"Oh, Kitti, you are such a little slut. You moan so delightfully, like you really mean it, and those whimpers you're making? Heavenly. You are a heavenly maid, Kitti. You are going to be one of my daughter's favourite slaves, I can already tell. Me? I prefer my slaves to be a bit more manly, but that still means there's a benefit to having you around, because you can suck their cocks off when they've earned a big reward.

"Oh how you squeal. But of course you're to become a cocksucker, Kitti, how would the life of our one and only sissy-maid be complete without the occasional mouthful of cock? Some of my boys have such nice big ones, oh yes they do. And one day, you'll get to taste them all. Not yet, though Kitti, be still your beating heart. First we break you, so you won't damage any of our property."

She fucked me hard and fast. The bench rocked and creaked but it held fast, and she put plenty of effort into making me feel her cock inside me. I whimpered around the gag, but she just laughed. I think it spurred her on, because she started to thrust as deep inside me as she could get and that only made me moan harder, and she thrust harder still.

She came and by the sound of it she had a marvellous orgasm. When she had left me, I was unlocked from the bench, then given food and water and allowed to use the bathroom. One of the guards took a little pity on me, and she had me kneel on the floor in front of her, with my hands locked behind my back. Once she had gagged me again, she hugged me for a while, rocking me slowly back and forth, until I was calmer. After that, she locked me up again.

Princess OCtavia's slave-father came in a while later. It was late afternoon by then, I think, but I had no way to tell the time. The guards treated him as just another slave, but they didn't interfere with him. He walked in front of me, so that I could see him while I was strapped to the bench, and I saw immediately that his thick cock was already hard.

"Have you been fucked by a man before, Kitti?" he asked.

I shook my head.

"Well, it won't be too different from what happened before, except that I'm going to cum inside of you. You might be hoping I'd go easy on you, but my orders are to take you pretty hard, and I'm a good enough slave to follow my orders well. I've not been allowed to cum in more than a week, Kitti, and I need this. I'm going to make you squeal."

He did. He made me his bitch just as much as his daughter and wife had. I remember him starting slow but building his speed up in just a minute, maybe less. He was rock-hard inside me and he bellowed with pleasure as he penetrated me. I could hear that he was struggling to keep from climaxing immediately, and to my relief, he didn't manage to hold off for long.

He came and then left without another word. About an hour later, when I could see the sun had set outside, Princess Octavia came back and inspected me. She washed off my bottom a little and wiped away the dried cum that had trickled down my legs, then she stripped off her clothes again and put the strapon back on.

"One more for the road, Kitti, I think. Then you can go to your room for the evening."

She made a wise choice fucking me, for it started to really break me. I found myself enjoying what she was doing to me, and the shock and shame of that realisation made me cry again. When the tears stopped, I couldn't help but finally feel the pleasure I'd been denying all day. When her strapon slid in and out, I felt a tingle run through my skin and up and down my spine. She slapped my rump playfully and I grunted out real enjoyment.

"Oh Kitti, don't think i didn't hear that," she said, "you're such a little slut, aren't you? Having a good time with me on day two! You see, baby, you were born for this. Kitti needs cock. Oh, I like that. Yes, that gives me an idea."

When she had finished fucking me, she led me back to my frilly bedroom while the guards marked me. When I got inside, Princess Octavia had a guard fetch me pen and paper, then it was handed to me through the bars. I was made to sit down at the dresser and clear a space from amongst the piles of makeup and other sundries.

"Now, Kitti," said Princess Octavia, "I've given you thirty sheets of paper. I want you to practise writing the way a sissy would write, with a nice curly, flowing script, and I will be marking your efforts tomorrow. Fill all thirty sheets, front and back, with just one phrase: Kitti needs cock. See you tomorrow!"

I was beaten. I wrote my lines like a good boi would, fearing the punishment I'd get if I didn't. It took me hours to fill up those pages, writing slowly in the way I imagined a frilly, silly maid would. My old handwriting was perfunctory, clear but unremarkable, and what was needed there was something totally new. I hit upon the idea of writing hearts above the i's of my 'name', and so I spent a long evening filling up paper with just three repeating words: Kitti needs cock. I went to bed believing it.

Day 3

On the third day I awoke and immediately started crying. I rolled around in bed sobbing and heaving, then I got up and looked at myself in the mirror. I pulled at my breasts until they hurt, but I didn't know what I was trying to achieve - it wasn't like I was just going to rip them off somehow, then escape. My fingers traced a circle around the collar I wore, and I pulled at it - it wouldn't budge.

I looked myself over again. I knew that it had all been done to me, but it struck me again that I actually liked this new body a lot. I looked like I had in so many fantasies, except this was real. True, I'd never fantasised about wearing a chastity cage I couldn't remove or a collar with a bomb in it. But the rest of me - I looked the way I'd wanted to, for so long. I had to think it all over, so i sat back down on the bed,

My thoughts were interrupted an hour later when Princess Cctavia came to collect me. Her dark eyes drank me in, and it struck me again how beautiful she was. She wore a black dress cut up to the thigh, which complemented her dark hair and her smouldering gaze. Her hair was up in a bun, and she held a riding crop in one hand.

"Get washed, sissy, then come back to the main room and put on one of your basic maid outfits - that's the top drawer. Put on a matching bra and knickers - black lace I think. Get moving."

I did as she said, and fifteen minutes later, I was finishing up my makeup under her watchful eye. I wore a brunette wig that had a sensible bob, and my makeup was in dark tones to match. I finished it, stood, and put on the four-inch heels she had told me to get out. I walked unsteadily to the door, then a guard reached through the bars and started shackling my arms and legs.

Princess Octavia collected two petmales and we went downstairs into a plush lounge, with a long stretch of clear floor. Octavia and the petmales lay down on a red velvet sofa, and two guards flanked them. I was pointed to the long stretch of floor, and made to stand ready.