Young Sissy Ch. 01


Author's Note: This is a follow up to The Young Master series. You can start here if you aren't interested in Belle's misadventures as spoiled young man turned out by his own sissy slave and eventually enslaved by his step-father, but it does introduce a lot of characters you'll read about in this series.


I don't know how long I was under...days, weeks...who knows, maybe even months. Reality blurred with nightmares as I felt my flesh being cut into by cold scalpels and stuck with needles, filling me with horribly persuasive dreams of a beautiful new body. I tried to imagine myself as a man, just to see if I still could, but it was futile. Every dream I had featured me with bouncing breasts, an hourglass figure that told everyone when it was time to fuck me...which was all the time, and a face of an angel..or a succubus. I just became more and more alluring in my dreams...more fuckable, and to my surprise, I no longer considered that a bad thing. In the heady twilight between reality and dreams, I didn't have the capacity for self deception I'd relied on so doggedly as a man. I couldn't force myself to feel guilty for relishing the thought of being every a waking wet dream, even if I wasn't 100% sure when I was awake...

My favorite dream was The White Room. In it, I woke up in a room where the walls and floor were all painted a solid, textureless white. It reminded me of my secret place, the place I could hide when my brain melted from trying to process too much pleasure at once. A place beyond reason, dignity, or morality. A place I didn't have to wonder why some of my proudest moments where when I was being humiliated. Where I didn't have to explain to anyone...especially myself, why the word 'surrender' sounded so musical to me; why it made me want to sway and writhe to its rhythm. Where pleasure didn't come with a price tag, and the cost wasn't always going up.

In my dream there were strange, phallic protrusions jutting out of the floor and the walls. Different lengths and thickness, with all sorts of different curves and ridges. No two were alike but they were all smooth and hard and slid in my ass with an almost eerie ease, as if I was perpetually lubed up. As I bounced up and down the studly stalagmites, I felt my body come to life, my hands hungrily devoured my new curves, seducing myself and making me want to fuck that slutty little bimbo even harder. My breasts had started as soft little peaches, juicy and tender from what I could only assume was hormones. In time they swelled to the size of small melons. I was at least a D cup now, although I never seemed to wear a bra in The White Room, or any clothes for that matter. Clothes would only get in the way of my eager little fingers, twisting my sensitive nipples until jets of cum escaped my shrunken clit in a sticky coo of satisfaction. I would thrust my head back and see myself in the mirrored ceiling, the only part of the room that broke the illusion of the void, feeling absurdly grateful to my captors for making me the gurl of my dreams. My golden hair crashed in waves against my alabaster skin, my bee-stung lips formed an ecstatic 'O', my already feminine features had been surgically softened, accentuating my button nose and big doe eyes. I probably should have been alarmed to see myself so changed so drastically, so permanently, and in such a short period of time. But there was no fear in The White Room. And as long as I could stay there, I would never have to face the reality my reflection hinted at. I never wanted to wake up...

"Wake up, Belle. You can't ride the decorative dildos all day. It's your first day as an official member of the harem, and I'll be damned if you're going to get me in trouble for letting you fuck yourself all day instead of showing you the ropes." I probably would have shit myself in fear if I hadn't been given daily enemas...or was that part a dream too? Standing in the doorway I didn't even know existed, stood the sissy that got me into this, the stunning raven haired goddess, standing almost six foot sexy, with soft skin and generous curves hiding hard muscle and a cold heart. Her dark eyes constantly smoldering, her full lips always slightly tilted in a sinister smirk. She had the face of a Madonna and the soul of a succubus. To see her was to want her, and to want her was to be damned. All I wanted now was to hate her, after all, she was the one who did this to me. I was supposed to be her Master, but she saw something else inside me, and teased it out of me one squirt at a time. Now that I had the body to match my inner beauty and I'd become just another sissy slave in my step-father's stable, I wondered if she would continue to tease and torment me, or if the affection she had so cruelly faked to bring me low would grow into something real. I said a silent prayer that this was still a dream, because if it was, maybe we could have something real inside my fantasy. "Are you even listening to me, you stupid slut? Or have you gone dick dumb from riding faux phalluses for hours on end?" wasn't a dream. Instead, my nightmare was just beginning.

I followed Isabella out of the room and into a nondescript hallway. I opened my mouth to ask her how long I'd been out, but before I could utter a sound, she said, "First off, don't bother to ask how long you were being 'perfected'. I don't know and if I did, I wouldn't tell you. Time is fluid down here. We know when to eat, sleep, and fuck based on a series of chimes. You probably never paid attention to it when you where upstairs because you never had to meet a deadline in your life, but there are no calenders or clocks upstairs either. So get used to not knowing even the most basic things and accepting whatever you are told." She spoke with a bitterness that I hoped wasn't all directed at me. I realized with a pang of guilt that she was right about me, no one had ever depended on me for anything, so I guess time had always been fluid for me.

I opened my mouth to speak again, and again she cut me off, "Don't bother asking anymore questions. I've heard them all before and I'll tell you everything you need to know to be a good little sissy, which is precious little. That's rule number one by the way...a sissy never asks questions. If she needs to know anything, her Master will tell her." I nodded and followed behind her, walking past a mind boggling number of rooms with different plaques on them...The Locker Room, The Prison Cell, The Count's Chambers, The Classroom...and countless other fantasy themed rooms. I bit my tongue so that I wouldn't let a question slip out, not wanting to upset Isabella before we had a chance to talk about all that had happened.

"Sigh...okay, I can see this is killing you, and you make a really annoying face when you're trying to think, so I'll tell you what the rooms are for. You might have noticed that the basement is pretty big. That's because it's not a basement, it's an underground complex your father built to live in after World War III or Armageddon, or a race war or whatever horrible old rich white men plan for." I felt a twinge of sadness at the mention of my horrible old rich white man father. I had never met the man, he died during my conception, a casualty of his own vanity. He married my mother at age 89, a ridiculous attempt to recapture his youth with a vapid trophy wife. He didn't make it past the wedding night, cumming and going at the same time as his heart gave out. I wonder if that's why I'm so weak? Maybe his sperm wasn't potent enough...

"But to make a long story short, Master Darren saw the potential of the 'basement' and has turned it into a fantasy brothel and sissy re-education center. Even I don't know how big it really is, or where the guests come and go from, but you'll meet them eventually. It's an expanding operation and you're the newest, but certainly not the last sissy to join the team." Suddenly, I felt even more insignificant, if that was even possible. Not only had my identity, my manhood, my fortune, freedom, and future been stripped from me, but I wasn't even special...I was just another sissy out of many to come. Isabella must have noticed my hurt expression, because she consoled me by saying, "Don't you dare get mopey around me. I will give you a reason to cry and then beat the tears out of you. A good sissy is a happy sissy. That's rule number seven. Dammit, look at you making me skip ahead."

"I'm sorry, Mistress Isabella." I didn't dare talk back to her, even if I did think she was being needlessly cruel...after all, she had me wrapped around her little finger when I was still technically a man, still officially her Master...I didn't want to find out what she could do to me now that I was just a sissy. I sucked up my sniffles and followed her without a word until we got to the showers. Before I could even eep, she pushed me against the wall, her hard cock crushing my tiny clit as it struggled to rise to its full two inches...

"Now listen up, because I'm only going to say this once. You're going to learn a lot of rules about being a good little sissy soon, but there's one lesson you need to learn right now. When the Masters aren't around, I'm in charge. If you stupid little sluts get in trouble, I get punished too. So you'd better believe I will keep you in line." Her hand closed around my throat. It was soft and warm, but it felt like it could crush my larynx with a single squeeze. I just kept nodding dumbly, not wanting to give her a reason to give me a demonstration of how she kept naughty sissies in line...

"Now down in the basement the rules aren't as strict. When we have free time, they don't mind us getting off in whatever way we can. But let me warn you, you won't always have a choice in how you get off, or more importantly, how you get the other sissies off. It's not my job to keep the other sissies from picking on you or making you their personal pet and fuckhole." I remembered the casual cruelty with which the voluptuous Latina Lola had fucked the tattooed, pierced, and shaved sissy, Cunt. And the other gurls had eagerly watched as Isabella had fucked the cum out of me. I had a terrifying vision of drowning in a pool of sissy cum that poured out of my well fucked holes. Or was that a tempting vision? The idea of submitting to another sissy made my sissy clit throb, but it also frightened me. If they had even an ounce of the pent up frustration I had at times, they would tear me apart like tissue paper. But without Isabella's protection, I didn't know what I could do.

"If you don't want to end up the bottom bunk bitch of a harem of sissies...and I'd be surprised if you weren't already drooling at the thought, you better assert your dominance and fast. If you don't pick a sissy to overpower and dominate, trust me, one will pick you. Who knows, maybe even you can boss around one of these born and bred bimbo bitches. But first things first, you stink of sweat and cum. Take a shower and then meet me in the dorms so I can finish your reorientation." I nodded yes emphatically, so terrified that I looked like a bobble head doll just to make sure I didn't upset her. She rolled her eyes and let out a sigh of disinterested disgust. I hung my head and made my way into the showers. I was starting to think this whole, forcibly feminized fuck doll gig might not be as glamorous as the brochure made out. Worse still, Isabella only saw me as an annoyance. After all we'd been through, I thought she would at least hate me, but this coldness was so much worse. I was beginning to understand why Dante put the traitors in the lowest rung of Hell in a frozen wasteland. I had betrayed Isabella, just as she betrayed me, and now a wall of ice separated us in Hell.

I was so lost in my thoughts that I didn't notice anyone else as in the showers, that is until I walked right into her. "Hey! What's the big idea?" I almost apologized reflexively, but I swallowed my sorry before I could utter it. I didn't want to appear weak, not when my entire future in the basement was at stake. I had to prove I wasn't at the bottom of the pegging order, and as I saw the hurt look on Cunt's face, I realized I had already found someone I could easily dominate. Her entire body was an advertisement for her weakness, filthy slurs tattooed in ornate lettering across her hairless body, topped off with 'CUNT' written on her forehead. She looked so vulnerable as the water cascaded over her skin, I could just imagine there were tears running down her cheeks. I hated myself for it, but I knew I had to put them there if I wanted to show these sissies I could be tough, or at least tough for a sissy... "Who do you think you're talking to, Cunt? I'll walk where I goddamn want, and you'd better watch where I'm going from now on." I sneered at her as I puffed out my chest, which wasn't quite as intimidating as I'd intended considering I was basically shoving my pendulous breasts at her, but I kept my nerve up. I knew it that it was now or never. I had to establish my dominance immediately so that her natural instinct to submit to someone stronger would kick in and I would have my first bitch. I thought of the various sissies in the harem. Obviously I couldn't make Isabella my bitch, that ship had sailed once I let her fuck me...five or so times. And I knew Lola could kick my ass just as easily as she could fuck it, but I didn't see why I should submit to Bambi or Sakura. I figured that even I could boss around a living kewpie doll and a school girl geisha. But first I had to see to Cunt...

"My CONTESSA!" I smirked as I saw her normally docile face scrunch up into a mask of diminutive rage. It was so cute...that is until she pounced on me, knocking the wind out of me as she hit me square in the stomach with her shoulder and used the full weight of her body to knock me to the floor. I struggled to regain my composure, to try to figure out what just happened, to try and regain control of the situation. But with her steely fingers pinning down my wrists and her powerful legs weighing down on my shapely but weak stems, I realized I never had control in the first place...

"So, you thought you were going to make me your bitch, is that it?" Her modest but shapely B-cup breasts crushed against my almost ridiculously well endowed tits. I squealed like a tortured mouse. I don't know if it was the steam rising from the hot water hitting the cool tile floor or if my new curves were making me feel even more submissive and sex starved than ever before...which before I found myself writhing underneath Contessa's firm grip, I would have never thought possible. "What were you going to make me do...suck your shriveled little clit? Or where you going to try and get it hard enough for a few pathetic pumps inside my sexy ass?" Her lips caressed my ear, her breath hot on my cheek, her teeth closed around my tender ear lobe...

"AIEEEEE!" pain shot through my head as her teeth cut into by flesh, I tried to scream, but she struck with the speed of a cobra, her mouth seizing mine, forcing my scream back down my throat with her nimble tongue. I soon forgot my pain as her tongue wrestled mine to the floor of my mouth and her nipples scraped against mine with a frustratingly frantic friction. Her smooth leg slid between mine, and despite my terror...or maybe because of it, I found myself desperately thrusting my hips, rubbing my swollen clit against her thigh, humping her like a bitch in heat. She released my mouth for a moment and I assumed she wanted to hear me whimper wetly, but then she jammed her leg violently into my baby-soft balls. "EEEEEEEEEE!" my scream would have made a castrato jealous.

"Ooh, I'm going to like playing with you. I haven't even broken the skin and already you're singing like a dying bird." My body was wracked with pain, starting from my bruised fruit and taking root up inside my guts, were it found fertile soil to plant pain....but just as suddenly as she thrust me into Hell, she delivered me into Heaven, moving with a feline speed and grace down between my legs, taking my swollen sack into her mouth and gingerly sucking on it, nursing it back to health as I fought back tears of anguished relief. "You see, Belle, I can be a loving Mistress...but only to bitches that show me respect." Her voice went from silky soft, a soothing whisper that sneaked into my ear to the cold, merciless monotone of an executioner, or her Master, Darius. She got up off me, satisfied that I wouldn't try to resist any further. She stood up and held her dainty foot in front of me, wriggling her little toes. I saw that B-I-T-C-H was tattooed on them with an ornate flourish and I felt a pang of shame that I would have a bitch for a Mistress. But I knew it was pointless to resist, and more than anything, I wanted to find out how loving she could be. I kissed the sole of her foot, licking from heel to toe and taking her dainty toes in my mouth one by one, alternating between sucking on them and sliding my tongue between them. I heard her laugh, it sound like broken glass falling to the floor...

"That's a good little long as you know your place, we'll get along just fine. And I'll only have to hurt you a little..." I looked up at her with a look of awe struck submission, not bothering to try and hide the fear and lust wrestling in my eyes. I knew that was what she wanted to see anyway. "You probably thought I was easy prey, didn't you? You saw the way my Master treated me, see my shameful submission literally written on my face, heh you even saw Lola riding me like a little fuck pony, didn't you?" She took her foot and placed it under my chin, lifting my head up closer and closer to her erect sissy stick. I'd never seen it from this angle, it was an intimidating sight, it had grown to at least a full five inches, and not terribly thick, but dotted with metal spikes that had been embedded in her tender cock. I imagined what it would feel like in my throat and I swallowed hard. I realized with a stifled sob that I was about to find out...

"Well I've got some news for you...I'm the toughest sissy in the basement. You could torture me all day and you'd only end up begging me for mercy. My Master has made me the strongest, sickest, sexiest sissy alive, and you little bitches belong to me when you're in my basement. I let your snobby sissy slut pretend she's in charge because she doesn't try and fuck my bitches, but make no mistake...she may enforce the rules, but down here...I make them. So if I want to order Lola to fuck me with her fat prick, then that's my business. But get this straight, she is a kept sissy, just like me, so that makes us better than you community don't you ever try and fuck me again. Get it?"

During her threatening tirade she kept rubbing her cock all over my face, the smell of lavender and sweat making me swoon and her hard steel grazing my soft flesh making me tremble in fear...and anticipation. I realized what a terrible mistake I'd made, and I was surprised at how guilty I felt. I don't know if it was the shock of processing all these new sensations and the onslaught of changes all at once, or if I was simply adjusting to my new role as a sissy slave, but I didn't even question why I was so eager to please her. Submitting to the strong just made was the natural order, it was my moral duty to honor the gods of Domination and Degradation, even if they were arbitrary and cruel. And the worst part was, I think a part of me wanted her to be unfairly malicious. I felt like I deserved to be punished for being so weak, for throwing my life away for a kiss...and who better to condemn me than another sissy? "Please, Mistress, please punish me for being such a stupid slut. I want to be a good slave!" Even as I was saying it I was cringing, my words far braver than I was. Maybe I deserved it, but I didn't know if I was strong enough to take my punishment.

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