The Young Sissy Chapter 1 free porn video

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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. Chapter 1 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?" Sigh...it 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 name...is 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 bitch...as 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 sissies...so 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 sense...it 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. Contessa looked pleasantly surprised, which for a fleeting, fluttery moment, made it all feel worthwhile. Of course, the moment couldn't last. I must have been smiling too broadly, or maybe my mouth was slack and drooling from feeling her cock kissing my lips, but suddenly I felt hot flesh and cold steel barreling down my throat, bringing tears to my eyes and stopping my heart. For a moment there was only the shock of the alien sensation of unyielding metal traveling along with soft skin and hard, but malleable muscle. And then my brain decided to make up for slacking off by processing the stabbing sensation of pain in stark detail. I panicked, sure from the intensity of the agony shredding in and out of my throat that I must be fatally wounded. Unfortunately, this only make my throat close tighter around the studded sissy stick, spurring Contessa on as I milked her hard clit. "Hmm I've got admit, I didn't expect much from your mouth, but you've got quite the talented little throat. I'm going to have to cut this short if I want to fuck that tender little pussy of yours." I didn't know whether to be relieved or horrified as she pulled out of mouth with a wet plop and let me crumple to the floor. Drool dribbled past my lips and down my chin, hitting the tile before me as I panted, slack jawed and spent. What I saw surprised me almost as much as my throat fucking...there wasn't a drop of blood in my spit. What had felt like mortal wounds was only sensitive nerves being pressed hard by pointed, but apparently dull metal studs. In a way I felt disappointed, sure I wasn't going to die, but that meant I had caved to pain alone. I had hoped I was past that, but every fresh hurt turned me into a frightened virgin, and I never knew when I would beg for mercy, humiliating myself and bringing more well deserved wrath on my head. I'd been lucky so far, but I knew I had to steel myself if I was going to endure what came next. Contessa took advantage of me being on all fours like a good little bitch, sliding behind me with that terrifying speed of hers and forcing her cock into my ass with one forceful thrust. "NNNGGGHH!" I gritted my teeth until I thought they might crush into powder, but I did not let the scream out. Contessa's slim prissy prick slid in with little resistance. Instead of making it easier to accommodate her member, it let her long shaft me immediately, digging a trench of boiling lava into the bottom of my love tunnel while the top of her mushroom head hit my sissy spot sending muted throbs of pleasure to ease my pain. But it was like tossing drops of water into a volcano...she wasn't hitting it hard enough to give me any real release, but I worried that if she sped up any more, her spikes would be the nails on my coffin, digging a hole I couldn't climb out of as the pain boiled over until I couldn't endure it any longer. That's when Contessa did something that really shocked me... "Aww...poor little, Belle...her first day and she's already getting trenched...I remember my first day here...how frightened and alone I felt. To be honest, I expected you to beg me to stop even before I shoved Mr. Chompers up your sissy chute. I'll give you a break, just this once..."and just like that...she pulled out, leaving only warm steam to fill my hole providing a balm to my ravaged nerves. I looked up at her with puppy dog eyes, overwhelmed by the unimaginable generosity she showed by not tearing up my ass. I couldn't form the words to express my gratitude, which made them that much more profound. "Aww...aren't you the friendly little puppy? Just for that, I'm going to clean you myself." All she does is curl her finger slightly, but an 18 wheeler couldn't have pulled me towards her any quicker. Before I knew it I was kneeling at her feet, warm water cascading down on us both. She put a finger on my chin and I immediately rose to my feet, eagerly awaiting her next command. She didn't speak a word...but her hands said everything, slowly sliding up and down my curves, soap covering every inch of my quivering flesh, her skillful hands finding every nook and cranny. I wrapped my lips around her shoulder to stifle a moan, and she took the opportunity to gently stroke my hair, the wavy blonde locks sticking to my back as she caressed my crown. I was shell shocked by this sudden change in her personality. She went from the kind of girls that rips the wings of flies and then tries to staple them back on, to this sweet, loving creature. I didn't know what to make of it, but I also didn't want to figure it out if there was something wrong with it. So I just turned off my brain and let the water run down our bodies, finding the tiny crevices between our soft embrace and heating them up as they caressed them with tiny streams. Of course, this oasis in Hell couldn't last forever. After what seemed like only an instant, but which my pruning fingers told me must be longer, she broke the embrace, practically cooing, "There. Now you're all clean and you can go meet my other pets." I smiled stupidly, no longer worrying about anything, and trusting my new Mistress implicitly, as if I hadn't just been ravaged by her. This comfort made me careless, and I forgot how quickly she could turn violent. All I was thinking about was the need throbbing between my legs and radiating from my aching nipples as well as the soul deep emptiness in my sissy pussy. "Please, Mistress, will you help me get off now. I haven't cum since I woke up and I feel like I'm going to rupture something." I don't know what I expected...I should have remembered a slave lives for pleasure, just not her pleasure. But what I definitely did not expect was to see the warmth freeze in her eyes and for her face to fall into a mask of merciless malice. "I should have known...still the same spoiled brat. You're not a friendly little puppy at all. You're a filthy little fuck pig. Well we'll see how hungry you really are..." She yanked me by the hair and I couldn't keep the shameful shrieks inside me. She didn't yank especially hard or even seem to care if she was inflicting pain one way or the other. She was just using it as a substitute for a leash, dragging me into the adjacent locker room, every step further eroding my will, leaving me a sobbing snotty mess by the time she tossed me unceremoniously on the ground. "Ugh...you really are a fuck pig, aren't you? Well luckily I carry around just the thing for sluts like you." I saw her digging into her locker and each item she pulled out made my heart beat faster, the blood rushing to my face so fast I almost fainted... The leash I expected...I almost felt relieved when I felt it tightly hug my neck. At this point I needed someone to control me, I was obviously in no state to...and it beat pulling me by my hair. The next item seemed cute at first, pink perky little ears on a leather strap that she fastened tightly around my chin. I thought maybe she had a change of heart and was going to give me another chance to prove I could be a good little sex kitten...that is, until I saw the pink plastic snout in one hand, and the butt plug in the other...matching pink, and flaring wider than any cock I'd ever taken, but long enough to mash in my gooey button, with a corkscrew tail completing my fuck pig uniform...I don't know if it was nerves or brazen lust, but I couldn't hold in an excited little squeal... "Ugh...you really are a disgusting creature." I had no doubt that her contempt was genuine, which made me feel hurt and worthless, but at the same time I struggled with the overwhelming excitement building inside me as I waited to find out what Contessa had in store for me. I was torn...on one hand I wanted nothing more to please my new Mistress, on the other I NEEDED to cum. One thing was crystal clear... my new Mistress was as unpredictable as she was dangerous, and I didn't want to give her any more cause to lash out at me than I already had. I would let her humiliate me and prove whatever point it was she was trying to prove, and I would learn my lesson, even if she was the only who knew what that was... I didn't know what expression she wanted me to wear as she slipped the snout on my face, but apparently a stupid grin wasn't it...I squealed again, but this time in pain, as her hand met my buttock with enough force to make my teeth rattle. "Don't you dare smile at me, piggy. You aren't even a human being anymore, just a disgusting animal. So you look at the floor and don't you dare say a word. Piggies can't talk. So if I ask you a question, you snort once for yes and twice for no, understand?" I start to nod, but then realize that would mean I would have to look up at her, so as dehumanizing as it was, I merely stared at my hands and grunted once as respectfully as I could. "That's a good pig..." Contessa rewarded my obedience by pressing the plug up against my puckered hole...I said a silent thank you for the lube she had evidently applied to it, because it slid in without much of a struggle. There was a moment when it felt a large rubbery ball of pain was being forced up inside me, but it tapered off as my asshole swallowed up the widest part of the plug and greedily gobbled the rest until all that stuck out was my cute curly tail. I marveled in the feeling of hard, unyielding rubber against my tingling nerves, it was different from the heated friction of flesh on flesh...not as intense, to be sure, but not as fleeting either. My ass wiggled involuntarily as I squeezed to hug it tighter with my anal walls. I could feel Contessa's disgusted stare dripping over me even without looking up, but I couldn't help myself. It was a vicious circle, the more humiliated I was for acting so depraved and wanton, the hornier I got over being humiliated. I couldn't control myself, all I could do was crawl behind my Mistress as she led me by the leash to what ever delightful punishment she had planned... She led me out of the locker room and through the labyrinth of identical halls. I had no idea how she knew where to go, but then again, I didn't need to know, because all I could do was follow anyway. Along the way, she would make staccato raps to the water pipes, sending out what I could only assume was sort of sissy Morse code. I wondered vaguely what she was saying, and who she was saying it to, but again I decided it was pointless to ponder it. There's a special sort of calm in surrender. Once you accept that you are completely powerless to change your fate, you are free from worrying about it. That is, until you pass the love of your life and the mother of all heart breakers in the hall and hear her sigh "Christ, Contessa, what the fuck are you thinking? You couldn't wait a full day before making Belle your fuck pig?" Her tone was exasperated, but not surprised. My mindless calm became troubled by waves of shameful regret. It would be one thing if she sounded jealous, or even disappointed...but she only sounded annoyed with Contessa for not being more patient. She didn't doubt for a second that I'd end up as a disgusting fuck pig, she knew it was inevitable...she just wanted Contessa to give me a day or two first... "Don't get your panties in a bunch, Isabella. Your little girlfriend here tried to make me her bitch, and then when in my infinite mercy I decided to forgive my new bitch, the nasty fuck pig begged to cum. So I'm taking piggy to get fed." I risked sneaking a glance up at Isabella to see her reaction, immediately regretting it. There was the usual tired disinterest, but the moment she heard about 'feeding me', she winced and something that almost resembled pity came into her eyes. I began to worry where I was headed, and remembered with a shudder that it didn't matter where I was headed or what Contessa had planned, because there was nothing I could do to stop her...only this time the thought wasn't so comforting. Instead, my helplessness only added to the gnawing worry eating me up inside. But all I could do was follow as my new Mistress led me away from my first Mistress and towards whatever twisted fate she had planned for me... I knew we had finally reached our destination when I let out a half fearful/half excited gasp...the playroom! An impressively large room filled with all sorts of twisted toys and the restraints needed to force me to play with them. My lip trembled fearfully under my snout, making me the perfect picture of a pathetic pet. I saw Lola leaning over a stockade, licking her lips lasciviously. I didn't know whether to be relieved or even more terrified. With Contessa I didn't know where her mood with take her from one second to the next, but at least there was the possibility for small pockets of kindness, an eye in the storm of her sadistic wrath. With Lola, I had the feeling I could count on consistency, but I had a gut punch feeling that it would be consistently cruel, or at best capricious. Her greeting didn't exactly allay my fears..."Hola, Bella, you are looking muy delicioso since you emerged from your cocoon. I've been waiting to feed you mi chorizo, so I hope you tiene mucho hungry." I wanted to explain myself, ask her to be gentle, but I saw the hunger dripping from her eyes, the same I saw in her Master's gaze just before he forced his fat cock up my ass without so much as a drop of spit. Contessa was silent as an executioner as she pulled me up into the stockade, securing my hands and neck and forcing me to stand spread-eagle with my ass arched invitingly just to avoid from chocking against my restraints. I couldn't see her as her long dagger-like nails slid gently across my skin, the tenderness of it only reinforcing how vulnerable I was should she choose to cut into me. That familiar treachery stirred within me, my body building up to a full scale mutiny against my better judgment, only my new body was even more persuasive. My breasts weighed heavily as they hung against the smooth oak of my stocks, caressed by hard, unyielding wood, they throbbed with pleasure, telling me to embrace the binds that hugged me so tight. My legs shook in anticipation, sending shudders all the way up to my generous ass, which shimmied as if trying to charm any nearby snakes inside. I wanted to say something, anything that might get them to see me as something more than sexual livestock, if not a human, at least a fellow sissy. But all I could manage was to grunt once for yes...oh God yes... Contessa finally cut through the thick silence with her steely voice, "In case you haven't figured this out yet, you aren't here as a reward. I will not tolerate a selfish sissy in my service. You will learn self control, or I will teach you the wages of sin Dante Alighieri style. But, I can be an angel of mercy or the Queen of Hell. It's all up to you. If you can make Lola here cum before you do, then I'll let you go back to being almost human. If not...well, let's just say you really can have too much of a good thing." Throughout her sinister speech, I pricked my pink pointed ears up and hung helplessly on every word. Still, it was tough to focus Contessa out of sight and with Lola stripping naked before me. She peeled off her tight whorish halter top and unzipped her miniskirt letting it fall to the floor. Unsurprisingly, she was completely naked underneath, her tanned skin looking so appetizing pulled taut over her voluptuous curves. She was probably the only one in the Basement with fuller curves than me, but where mine were soft and yielding, one look would tell you that you could bounce a quarter off of her bubble butt, her thick thighs and broad hips looked like they could pop a watermelon, even as her hips curved in steeply, giving her the figure of a bronze Barbie doll or one of R Crumb's wet-dream-girls. Her cock was even more impressive, uncut, it really did look like a mouthwatering sausage, and a frighteningly filling one at that. It must have been a lucky seven inches long, and so thick my jaw hurt just staring at it. But by the time she finally pressed it to my lips, saying "Come on, puta, it's tu comida...so eat up...", I didn't so much open my mouth as I moaned around it... It was only the fourth cock I had in my mouth, but even so, I was sure I'd never get tired of tasting a new treat. Just as Isabella's was milder than my step-brother Dale's cock and Contessa's had a more flowery smell and a bite to it, Lola's had its own unique taste, texture, and shape. For one, her foreskin gave it the delightful sensation of unwrapping a piece of candy with my tongue, only it was one of those Mexican candies, salty and a little spicy from the sweat trapped underneath its hood...but far from unpleasant. And her girth was making me swoon, and not just from the lack of oxygen. Feeling her stretch my throat to cartoonish proportions sent submissive shivers down my spine. I couldn't resist wiggling my little tail and clenching down on my pretty pink plug so that it would press against my pretty pink prostate and make my entire body throb with every surge of her hot tamale. I was beginning to wonder why anyone thought being a sissy's bitch was a bad thing. I couldn't imagine ever turning down Lola's fat clit, so why should I care if I didn't have a choice? I soon found out when she began lovingly stroking my hair, softly at first whispering, "Mi amor, mi chiquita bonita, mi cochinto chinga" and all sorts of other romantic sounding serenading. But then she gripped my hair tightly, and as if she wasn't aware of what she was doing, started thrusting so fast, that my head was getting slammed against the hard wood...even as her hard wood reminded me of how bad something I loved could hurt me. She still was cooing at me, "You're such a good little piggy...es so sexy when your snout mashes against mi stomach...I'm going to ask Contessa if she minds me tying a ribbon around your tail...cute...little...tail...and...cute...little...throat..." I guess the best thing about Lola was also the worst thing. She wasn't vindictive like Contessa or manipulative like Isabella...she was just passionate. But it was a passion that burned up everything it touched, and she was its first victim, lost in mindless hedonism and completely unaware of how brutal her love was. My only consolation was in knowing that at this rate, she would fill my throat with her milk before she could even think about fucking me. I would prove my worth as a sissy and I wouldn't even have to do anything. I just hoped I would have enough brain cells to appreciate it once the drunken stupor of an oxygen starved brain wore off. And then I heard the familiar sound of Contessa's sharp voice cutting through my daze..."Pathetic. You couldn't even wait until she started fucking you, could you? No, you had to milk your disgusting toy tail for all it was worth. Well I hope it was worth it, because I don't give second chances..." I had no idea what she was talking about, until I felt my legs go rubbery and my clitty spasm and shoot, sending gushes of giddy glee throughout my rolling curves. This new body seemed even more responsive than before, with my golly gee spot bursting into a blissed out flood that pumped through my veins, my nipples radiating the happy hurt they usually only sent out for a hard fuck and my White Room closing in around me, Lola metamorphosing into an angel sent to deliver me from the darkness and lead me safely into the pure perfect light of salvation...and then she pulled out. Once I stopped drooling long enough to think and my mind chugged back to life, I remembered that Lola had delivered me evil, she had handed me over to it...dropping me into the claws of the Queen of Hell...I could only imagine what kind of unimaginable torture Contessa was cooking up behind me. I think any sight would have been better than the swirl of images pulling me down into the abyss of hopeless terror. When Lola joined her Mistress behind me, I became doubly worried. I felt a tug on my tail, and I squirmed helplessly as it was sloooooowly pulled out of me, the width of the plug bringing back that taut pain as I stretched my sphincter to make its way out. But I was surprised that it didn't hurt more, it must have loosened me up a little the first time, because I noticed the sweet stabs of pleasure more than the heated hurt. I even let myself hope that maybe my punishment wouldn't be as bad as I feared. But of course I was wrong. My punishment ended up being much, much better than I could have ever imagined...and that was the true Hell of it... "Mami, por favor with sugar on top, can I fill this piggy with leche before you punish her...think of it as extra lube..." this sounded about as far from punishment as things could get. Ever since I saw her bronze beauty thick and throbbing before my lips, I had wanted...okay, NEEDED to feel it inside my hungrier hole. And with my cute little tail cut off, my pussy was feeling excruciatingly empty. Once again I wondered what they could have done to make my new body even more wanton and willing. It's not like I had an asshole transplant...did I? Had they surgically grafted a woman's pussy into my ass? As ridiculous as that sounded, the reality seemed even less plausible, because with my asshole as sensitive and responsive as it felt in that moment, I doubt I'd even be able to fart without cumming. I waited with bated breath to hear Contessa's answer, saying a silent prayer to all the devils in Hell offering to sell my soul if she would just say yes, hoping they didn't know my step-father already had a lien on it... My prayers were answered in the form of a warm, silky smooth pressure against my throbbing hole, Lola slid in with ease, and I grunted "YES! YES! YES!" as she slid effortlessly into me, her once frightening width bringing only a playful pinch to my tender tissue. Instead of tearing me apart, she was filling me up, hitting every weak spot inside me at once. At that moment I forgot that I didn't have a real pussy, I was certain the lube that let Lola slide in and out of me at a quickening pace must have been my pussy getting wet. I struggled to make sense of it, but then I felt her hands slide up and down my pendulous breasts, teasing them with tantalizing pleasure that tickled it's way across my skin down to my swollen nipples. They were so hard and so puffy, they looked like a bee had stung them, only instead of venom, he filled them with sweet sweet honey. Now I was certain that these were my real breasts, not implants...they just had to be, it's the only way the could fill up with hot liquid lust, like two water balloons ready to burst...the only way my nipples could throb with the beat of my pussy pumping out the backed up gurl goo into my veins and out to every quivering capillary under my skin. It made sense when I thought about it...or I guess the appropriate word would be 'felt' about it...because it felt real...and feelings were so much more real than reality. Besides, if I had a pussy, I had to have breasts, and if I had breasts it made since I had a pussy. I was dizzy chasing myself deeper and deeper down a vicious circle jerk until my brain gave up even trying to work it out and deferred to my body's infinite wisdom... I should have been worried. Sex as a sissy had been overwhelming back when I was still technically a man, even disorienting, but things had never felt so oppressively unreal before. It wasn't like before, when my mind would reach a point where it couldn't process the orgasms multiplying exponentially until there was no room in my head for anything else. I mean, sure that was happening too...especially since Lola's passion was only matched by her endurance her prickette filling me again and again, setting off cluster bombs of devastating euphoria. But unlike before, things didn't just go blank...there was something waiting, some sort of back up, filling the White Room with a flood of images and thoughts too fast to comprehend...which only seemed to make them more convincing. Some small sliver of sanity was trying to reject the decadent mantra, knowing instinctively somehow that the more right things felt, the wronger they were, but all that came out of its savage scream was, "SQUUEEEEEEEEEE!" "Ooh it looks like piggy like's her food. Well here cums some more slop, puta!" Lola grabbed my buttocks, squeezing down on them so hard she forced out another squeal of delight. She pulled me back onto her throbbing member so hard my teeth rattled and I felt a flood of sissy fluids fill my hungry hole. Her orgasm traveled through me, rolling downhill like a sticky snowball into it buried me in creamy perfection...it was like I couldn't feel a part of me that wasn't cumming, even my soft, shriveled clit was spurting out a thin drool of sissy squeezings. She sighed as she massaged my buttocks, kneading them as if to milk the last shuddery spurts...each one sent shivers of sizzling delight through me. By the time she pulled out and left me hanging limply in my stocks, I felt well fucked and well filled. If this was punishment, I was going to be a very naughty gurl. "Hmm...just what I'd expect from a little piggy. She ate her meal and now she's ready to roll around in her filth and pass out. But this is supposed to be punishment, remember, piggy? Or are you ready to be a good sissy? I'll give you the choice. If you are willing to go a week with out cumming, I won't punish you. That, or I can make you cum right now. Well what will it be?" Contessa asked as if she already knew the answer, as if going through the motions for formality's sake was a tiresome chore. But how could she expect me to turn down a chance to cum for a week's worth of no cumming? I couldn't think up a worse punishment than that...and I hoped that neither could she. My mind was still hazy from my deep dicked drunken cum high, but what little rational thought that poked through the fog all told me I needed to cum...that it was worth any punishment for a little more pleasure. I didn't know if that was coming from me, my body, or the mysterious new place beyond The White Room, but at that moment, it didn't matter. I knew what I had to do. I snorted once for yes...and I snorted very politely... "So pathetic...and so utterly predictable." Contessa was still out of sight and after a few absurdly long seconds, I began to have second thoughts. I was still too horny to worry about the punishment, but I was starting to worry about the funishment. I was worried that the way Contessa liked to cum and the way I preferred were world's apart. But then Lola wheeled out the most captivating contraption I've ever seen. Lola showed it off with a grand flourishes of her arms, as if she were revealing the grand prize on some perverted game show. It was a behemoth on wheels...a giant motor attached to what looked like a powerful piston and at the end of the piston...an ultra realistic dildo, fat and long, just like I liked them. All of the sudden I saw the dark humor in her offer to let me cum in exchange for a punishment...cumming was the punishment. That machine was both a sex toy and a torture device...it just depended on how long you left it on. And from the look on Lola's face, it was going to be left on half past Hell... "Lola and I have places to be, so we'll just let The Obliterator5000 here keep you company until we get back. I'm sure it won't be more than a few hours at most...try not to have too much fun." Try not to have too much fun. I would have laughed, but I knew the joke was on me. I heard the sinister squeak of the wheels as they positioned it behind me, felt it slowly part my pussy as it slid into place, making me snort reflexively, my body happy for sloppy seconds even if my brain was running around in circles looking for a way out. The I felt a dribble of precum leak into my cunt, my lust/fear addled mind not sure if it was an inventive lubing mechanism or if they somehow got a real cock onto that infernal machine, and I knew I was lost. By the time I heard the click of the Obliterator whirring to life, I had surrendered to the inevitable. Surrender, it was beginning to become my defining trait, to the point I wasn't sure what else was left. Did anything else really matter if it could all change with a blush and a whimper? Paradoxically, I felt the familiar feeling of hopeless optimism well up inside me the moment I gave in. I thought that maybe I'm more of a slut than they ever dreamed, and this really will be a reward for me. I don't know why that was supposed to be a comforting thought, but it worked well enough to dull the sharp edges of nerves stabbing into my gut. But what made even less sense was how I could still find hope in the first place. Things were already hopeless long before I ended up in the basement, maybe even as early as birth. Maybe my new Master was right, maybe some people are destined to be slaves, but even if I wasn't, that didn't change my circumstances...and what hope did a sissified shemale slave have? I couldn't think of a single reasonable scenario that meant anything but unending torment and terror...but I could think of dozens of increasingly impossible scenarios, and I clung to them like a life raft in a tsunami. My impossible scenario seemed downright possible as the machine began pounding my pussy with pneumatic precision, perfectly calibrated to hit my G spot as well as a few I don't know if Cosmo has discovered yet. I soon climbed up to the dizzying heights of decadent hedonism I had reached earlier, foolishly believing them to be a pinnacle...but as the cock kept fucking me, the explosive force of my orgasms took me past escape velocity and into outer space...the hot friction fueled my ascent as I came faster and faster, my soul shooting like a comet as every atom in my body vibrated in a harmonic Hallelujah...blazing past Heaven and into realms of pleasure undreamt of by mere mortals. In other words...I came...a lot...more than the Surgeon General's recommended daily dose. I was more than high on my own body, I was overdosing. Whatever they had done to me had made me infinitely more susceptible to pleasure...with an emphasis on the infinite. On my journey to the edge of the universe and beyond, I had all the time in the world to ponder the indecipherable whispers surrounding me like a blanket of light. Whatever they were saying, I felt safe and calm as I listened, like an infant in her mother's womb, absorbing the sacred truths of the universe in my cosmic egg...and I could have gone on like that forever...that is until the whispers turned to screams... I still couldn't tell what the voices where screaming, but I knew that they were angry. I felt guilt unlike anything I'd ever experienced before gnawing at my soul. If the earlier whispers were letting me know that it was good to be fucked, the screams were telling me it was bad to cum without permission. I remember being scolded before, a room full of sissies mocking me as I lost sissy chicken to my own slave...the humiliating sting of my bratty step-brother, Dale, blackmailing me, buggering me, and then berating me for being a selfish sissy and cumming first...my final eruption as a man sealing my sticky fate as a slave...and now Contessa, punishing me for being a greedy little pig. It brought all of my insecurities flooding back...I had always believed the world owed me everything...and then one day I learned that not only do I owe the world everything, I have nothing to offer. A failure as a man, becoming a sissy wasn't a point of pride like with some of the other girls, it was an escape attempt...one I botched when I agreed to become a slave in a moment of weakness. Now the only thing I had left, the only thing that mattered, was being the best slave I could be...and before I even started I had already failed by being the weak willed spineless brat I always had been. Of course, none of this guilt stopped me from cumming. Not by a long shot. My body was an insatiable little cock pig. No matter how violently my mind retched in self disgust, I couldn't deny the irresistible bliss of being force fed orgasms until I burst...and burst...and burst. But unlike my earlier escapes into superego destroying euphoria, the guilt gnawing at me only grew more vicious the fuller I got. I tried to cry out knowing there was no one to here me...to beg for mercy I knew I didn't deserve...but I couldn't find the words. How could I beg to be fucked harder and to stop at the same time? Was it weaker to give into the voice of conscience I wasn't even sure was mine? Or was it weaker to give into my basest desires and eagerly accept my role as a fuck pig? Honestly if I could have done one or the other, I wouldn't have cared. It was being caught in the maelstrom I couldn't endure, but even though it was unbearable, all I could do was wait for it to end. Time was always a tricky thing when I was getting fucked...moments could stretch into infinity and hours could melt away like butter in a hot skillet. And in a place where the concept of time was forbidden, things grew even more strange, the absurdity taking root to the point that Hell grew from an abstract analogy into a very real, very physical place. Hell didn't need a lake of fire or demons or the tortures of the damned. Hell was the place you ended up when you had nowhere else to run...Hell was facing yourself and not being able to turn away. Hell wasn't other people...Hell was being given exactly what I wanted...forever, and realizing how terrible my appetites were... By the time I was finally released, I had run out of tears...or any other fluids for that matter. I shivered uncontrollably as I collapsed to the ground, my limbs useless and rubbery, my skin dripping with sickly sweat. My mouth dry, only just able to mouth the words "I'm sorry" over and over again. If Contessa noticed, she gave no sign of it...cruelly dragging me by the leash back out into the hall...forcing me back onto all fours as my limbs came alive in brilliant flashes of pain. Everything hurt...the mere absence of endorphins flooding my body sent me into orgasm withdrawal the emptiness filled only with jagged sobs. I kept pleading for forgiveness, but I couldn't form the words, I was terrified I would never recover, that I had become brain damaged and broken, a defective sissy. I wondered if she was leading me to the incinerator or the slaughterhouse...I prayed for either...anything that would bring an end to the pain. But most of all, I prayed for forgiveness...I doubt she heard me. And if she did, I'm certain she didn't care... Instead of my end, we returned to the place where our relationship began. She led me back into the showers, tying my leash to a ring on the wall I can only assume was designed for that very purpose. Then, as if turning a hose on a pig covered in her own shit, she turned the shower on full blast, saying, "You missed dinner while you were being 'fed', so bedtime can't be far off. Try not to make a pig of yourself before you turn in. If Isabella nags me for your sloppiness, then I'll take it out of your ass...and not in a way you'll enjoy." She didn't give me a chance to respond, not that I would have been capable of a response anyway. No, all I could do was let the water crash down on me, washing off all evidence of the filth festering inside me and allowing me to pretend my tears were only the water hitting my cheeks. That is how she left me, leaving me to sway back and forth under the empty caress of warm water, convinced I'd never get clean. My only consolation was that things probably couldn't get worse...or at least not before bedtime. But of course I was wrong...because Contessa had sent Bambi and Sakura to fetch me and 'tuck me in'... "Aww look at thew widdle piggy. She is like a gagillion times cuter than that Charlotte's Web piggy." I blushed at the bitchslapped compliment, staring up at the kewpie doll with a mix of fear and lust. I thought I had her pegged, what with her cotton candy pink hair...which I could only guess was her petulant reaction to having another blonde join the harem...it was spun into girlish pigtails and only added to her porcelain fuck doll allure. Her baby doll make up accented her fair skin and her long lashes fanned her bright blue eyes, giving a look of demure innocence, but it only took one look at the way her Clara Bow lips curled into a hungry smile to make me worry about the easy confidence that carried her closer to me with every bouncing step. I turned to Sakura for support, hoping the kindness I showed her when I was still a Master would be returned now that I was a sissy, but she wouldn't meet my eyes. She was humility personified, shamefully looking down at her maryjane shoes, the archetypal Japanese schoolgurl, her ivory skin painted like a geisha with her bright red blush. I noticed that she was being led by the hand by Bambi, and I realized I wasn't going to get any help from her. She was obviously Bambi's bitch...which meant that Bambi wasn't the obedient little girl I had imagined. I thought I had her pegged, but it was beginning to look like she would be pegging me instead. Her voice bubbled out in sing-song mockery as she walked towards the faucet, teasing "This little piggy went to the white slave market, and this little piggy never went home, this little piggy got spit-roasted, and this little piggy went..." "EEEEEEE! EEEEE! EEEEEEE!" Icy cold water cut into me like countless tiny shards of glass. I scurried away from the water on all fours, Bambi laughing behind me as she aimed the shower head at me and hand on the cold water tap with a kung fu grip. She giggled as she watched me try to escape from the jets of icy water while still tethered to the ring by my leash. I finally gave up running, instead crawling through the shivery shower to kneel at her feet, begging her to stop... "Oh Pooh...don't tell me you can't take a joke. You aren't going to be like Sakura are you? Pwetending you hate being my gurlfriend while secretely wuving every minute?" Thankfully she had turned off the water, but I couldn't stop shaking. Not just because of the cold...but because I looked up to see the anguish in Sakura's almond eyes as she tried to avoid my gaze. I had no doubt that what Bambi considered a gurlfriend, most would consider a prison bitch. I surprised myself with a lack of self preservation, more concerned for Sakura's well being. I didn't know where this sudden selfless streak was coming from, but I didn't want to scare myself away from it, so I just blurted out the first thing that came to mind, "How dare you? Can't you see she's suffering? How would you feel if you were stolen from you homeland and forced to come to a strange land where you barely spoke the language? Don't you know how important honor is to the Japanese? You're lucky she hasn't committed seppuku." I felt a strange sense of relief after getting it out, as if I had accomplished something even if I was just humiliated and abused for my efforts...as I was sure I would be. Maybe it didn't matter what the results were, maybe all that mattered was doing the right thing despite the consequences. Or at least, that's what I thought until Sakura spat on me... "Baka Gaijin! This humble sissy is American as the pie of the apples! I am very good speaker of English, and I am not a fucking JAP!" I crawled backwards until I was backed up against the tile wall, trying to get some distance between me and a suddenly not so submissive Sakura. I couldn't understand why she was so mad...if she wasn't Japanese, then why did she dress like that? Why did she talk like that? When Bambi laughingly explained it to me, I wished I never learned the answer... "Silly widdle piggy. Don't you know Koreans hate being called Japaneesy? Espeshually Korean-'merry-cans. 'Sides, it's a total sissy party foul to bring up who we where before we butterflyed. But you'll understan' why we talk so siwwy once you've had your grammer and electrocution lessons." Sakura looked away, tears in her eyes. I couldn't imagine what could transform someone so completely into a living caricature...but mostly I hoped she had misspoke when she tried to day 'elocution lessons'...but I had a gut-punch feeling that she knew exactly what she was saying... "Hmm...now how should I punish this bad widdle piggy for my makin' my gurlfriend all sad faced?" Bambi had finally untied my leash, only to wrap it firmly around her hand and pull me up to my wobbly feet. I knew she didn't care about Sakura, but she wasn't about to waste an opportunity to punish me for it. After my marathon session with the fuck machine, I didn't have the strength left to fight them off...and I wasn't sure I had enough before that either. So I did what anyone would do when faced with a hopeless situation...I begged for mercy... "Please, can't we just be friends? I don't want to hurt you...and I REALLY don't want to get hurt. Why can't we all just be nice to each other instead of acting like bimbo bullies?" When I finished my little speech I was on the verge of tears...it was heartfelt...it was stirring...it was utterly pointless. Trying to appeal to the humanity of a sissy is like trying to teach a cat algebra, they'll never understand it and you only look stupid for trying. The worst part is, I couldn't even blame her...she's not the one that took every last drop of humanity and rang it out of her like she was a filthy rag. I wondered how long it would take for me to become as playfully cruel as her, and if that would make me stronger. "Of course we can be friends...the bestest of friends. As long as you do whatever I say, whenever I say it. After all, I'm a pwetty pwincess and you're just a maid. Of course, if you want to upset the social high- archey, then you know what you have to do. Beat me at sissy chicken and I'll be your widdle baby bitch." The way her eyes shined when she challenged me, I couldn't tell if she was looking forward to winning, or hoping she'd lose...I doubt she really knew either. She definitely played up her spoiled little gurl persona...maybe she just wanted to be put in her place with a hard spanking? I felt my intestines unravel a little as I thought of how a game of sissy chicken would play out right now. The game was easy enough and deliciously hard at the same time...all I had to do was rub my clit against hers and make her cum before I did. Normally, this would be an exercise in futility, as I have a hair trigger squirt switch, and Bambi knew it. But what she didn't know was that I had just had every drop of cum pumped out of me and that no matter how good it felt, all she'd get was a dry spasm from me. I mulled over my options, I could even challenge Sakura to a three way match and make both of them my bitches at once. Sure, I'd still have to kowtow to Contessa and Lola, but that seemed to be the natural order down in the basement anyway. In one fell swoop I could go from bottom bunk bitch to head of the free range sissies with two sex starved bitches to attend to my every dark desire... That's when I realized I didn't want to make anyone my bitch. Not that I wanted to be their bitch...okay well maybe a little, but I'd rather have been their friend. I knew that if I beat them, I'd have to treat them as cruelly as they planned to treat me, if not crueler. If I didn't, they would resent me for it and make me their bitch anyway. No one fights more zealously for the oppressive social order than a sissy...after all, it's the only way they can justify their fate. But I was different...I don't know why...maybe I wasn't strong enough...maybe it's because I didn't have to fight my whole life like most of the other sissies probably had to...maybe I just felt too much, but I couldn't bear the thought of causing anyone the kind of pain I'd felt. I only had once choice...I lowered my head and meekly whispered, "No, Bambi, I don't want to challenge you. I'll...I'll be your gurlfriend." "Oh goody cumdrops!" Bambi lifted my gaze to hers and I saw her face light up with child-like glee. She wasn't exactly sadistic, just spoiled. She was just a big kid in a bimbo's body...which might be scarier than a straight up sadist. Whatever else she was, she was giddy with dominant delight; pulling my pink plastic snout off so she could cover my face in soft, fluttery kisses and suck on

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Young Sissy Ch 03

"Pleez...por favor...pretty pleez...fuck me..." I looked up at her with tears in my eyes, pleading to be penetrated. I didn't have to beg...nothing in the world would have stopped Lola from spraying her seed deep inside my ass...but I know it's what they wanted to hear. I regretted it immediately...well almost immediately...nothing can take away from the pure satisfaction of hot flesh filling my pussy. It made me feel...whole. Of course, it also pushed down my cum button and sent my body into...

3 years ago
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The Young Sissy Chapter 2

I was walking in a field, the cool grass crushed softly between my toes, the sun warm on my skin, the smells of spring were in the air and every deep breath I took filled my lungs with the promise of a fresh start and new hope. The sky was a flawless blue and looked clear enough to take a swim in. Everywhere I turned, all I could see was endless rows of rolling hills...there wasn't a soul in sight...and yet, for some reason, I didn't feel frightened or lonely like I usually do by myself....

3 years ago
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My Young Sissy brother for Mens Cum today

sharleesisterboyMY Young SISSY brother in Heat for Men's Cum, today!You used to prance around the house in your white underware, when Mom was gone, shaking your cute ass at me till I caught you, roughly, in My Big brothers arms and carried you to my bedroom floor. You giggled all the way, till I tossed you down on the dirt floor and you tumbled and smiled up at Me and lay on your tummy with your legs spread wide for Man-Cock. You know what I like to do to You, but, instead, I tie your wrists...

4 years ago
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Young Sissy Ch 02

I was walking in a field, the cool grass crushed softly between my toes, the sun warm on my skin, the smells of spring were in the air and every deep breath I took filled my lungs with the promise of a fresh start and new hope. The sky was a flawless blue and looked clear enough to take a swim in. Everywhere I turned, all I could see was endless rows of rolling hills...there wasn't a soul in sight...and yet, for some reason, I didn't feel frightened or lonely like I usually do by myself. It was...

2 years ago
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Young Sissys Story

Today I want to share with you my story. I’ve finally managed to gather enough courage to tell you about how I became a sissy and what has that meant to me, but before that I'd like to thank xhamster for giving me the opportunity to share my story. I’m very grateful to porn for helping me discover my sexuality and my true nature as a sissy and for helping me develop new tastes and discover new pleasures. Now let’s get into my story. So, as you’ve read in the title, I’m still a young sissy, I...

3 years ago
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Chastity Sissy Katie gets fucked by huge young coc

It had been months since I had indulged my sissy urges. I have been spending a lot of time in chastity and had been locked up for 8 days when I decided I had to have a real cock inside me. I messaged my usual older daddy and was disappointed to find out he was out of the country. Too horny to wait I placed an ad on Craigslist and narrowed it down to an older guy with a decent looking cock and made a date for the next day. I spent the morning getting ready and just as I was about to leave he...

4 years ago
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Mothers Sissy Teachers Pet

Mother's Sissy, Teacher's Pet By Sandy Brown January 15th, 2012 Dear Ms. Brown, I am Sandy's homeroom and science teacher. I thought I would mention to you that I noticed that Sandy had a small amount of nail polish on the base of his fingernails today. I assume that he was having some fun with you over the weekend, and that before he left for school you used nail polish remover, but inadvertently left some polish on. The color is very pretty, and I'm sure he looked adorable, but...

2 years ago
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Young Sissy SonBrother Part 2

Young Sissy Son/Brother Par 2 After lunch, Bree announced that it was her turn to be in charge, and she wanted to play dress up. "What?" "Dress up. You know, we try on different thing's and act (girly)." "Like what kind of things?" "Come up to my room little brother and I will show you." Up in Bree's bedroom, Alan was concerned for the first time that his sister was now firmly in "control," for the balance of the afternoon, that is. While younger than himself, Alan still...

2 years ago
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The SissyMaster

THE SISSY-MASTER CHAPTER 1 I have read many tales and stories on this site over the years; some of them 'autobiographical' and some of them complete fantasy. It strikes me that most of the stories have been written by the, either real or wannabe sissy girl and therefore is 'her' fantasy from a sissy's perspective. So I have written my stories of my experiences, beliefs and methods from the perspective of the male. This is for the REAL MEN that read this site, a guide to the...

4 years ago
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2088 Its a Sissy World

2088: It's a Sissy World Charles Pauline - Data Processor Cindy Pauline - Charles' wife Ms. Miriam Jensdotter - Charles' Boss James Marie - Charles' work friend Ms. Marysdau - James' boss Creampuff - A Sissy Store Worker Babykins - A Sissy Store Worker Suzi - The Sissy Store Owner Butterscotch - Creampuff's Roommate Supervisor Gabriellez - Creampuff's Apartment Supervisor Janice and Roger - Passengers on the Looper Ms. Hardcastle - Milking Salon Director Nurse Hamilton - Milking...

3 years ago
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The Sissy App

The Sissy App 1. Setup "This is the longest user agreement I've ever read!" thought Rick as he scrolled and scrolled through the hundreds of pages of legalese on his recently-downloaded smartphone app. The "Sissy App" User License Agreement was indeed voluminous, containing numerous sections detailing the GRA Software Corporation's exemption from penalties, payments or legal requirements, granted by authorities or statutes, for any harm that may come to a user when using the Sissy...

3 years ago
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Meinen Mann zur Sissy erzogen

Achtung diese Geschichte ist noch voller Rechtschreib- und Gramatikfehler. Jeder der m?chte kann diese Geschichte als Vorlage nehmen und sie verbessern. Jetzt reicht es mir. Ich hatte die Internet Seiten meines Freundes gefunden. Er surft also st?ndig auf Adult Baby Sissy Seiten. Ich hatte mich schon l?nger gefragt warum er im Bett nichts zu Stande bringt. Das kann er haben, ich werde ihn einfach in ein kleines Babym?dchen behandeln bzw im Grunde verwandeln. Er war eine Woche zu einem al...

1 year ago
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Chrissie The Saga of a Lovestruck Sissy Maid

Chrissie by c.w. cobblestone BOOK ONE "Mrs. Martin" Part I My right leg had a mind of its own. Rebecca frowned. "Why you keep bouncing like that? What's wrong with you?" "Um, I ... I ... nothing." "Bullshit, nothing. Something's up; you been acting weird ever since we got back from Paris. What the hell's going on, Chris?" I balled my fists. Clenched my jaw. Closed my eyes. Drew a breath. Took the plunge. "Okay. Okay. It's just ... well, now that we're...

2 years ago
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Sissy spit roast sleep over

Pt 1: Long black limoSissy Saraya was very excited because her new mistress had told her they were going to continue with her corset training tonight, she had been wearing her waist trainer and inflatable plug all day along with her favourite pink maids outfit and cute sissy 6" white heels and stockings with pretty pink bows, She had been watching BBC porn all day and was dreaming of cock while she finished her chores, Mistress text to say her driver would be arriving at 6pm sharp, Mistress...

4 years ago
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A Sissy called Jezebel Part VIII

A Sissy called Jezebel Part VIII - Jezebel has returned to hir classes at Templeton Academy: where young womyn become dominatrixes and sissies are crushed into submission. We are all getting an education on the Matriarchy in hir sissy life skills class. (Authors note: We are definitely at that world building point, where I really let my imagination fly off the hook. I am throwing out a lot of ideas, but hopefully in...

2 years ago
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The Sissy Contest

Author's Note: This is a quick one off story written from a reader request. I was especially motivated to write this as a genuine sissy training fantasy, with the hopes that somebody would read it and use it as a blueprint IRL. That certainly got my clittly interested! Enjoy! And as always, please feel free to comment here or contact me directly at [email protected] xoxox Emshoninque The Sissy Contest My phone rang just after 3am-caller unknown. I normally don't answer...

2 years ago
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Adult Sissy Little Girl World

Journey Into A Special World My name is Hannah Stone. I've been a reporter for a newspaper for years. A couple of days ago I ran into an old sorority sister and good friend Linda Hart. It's been a few years since we last saw each other and we decided to do lunch together. At the beginning of lunch we had the usual light chat. Then we sort of got on the serious side of chat, when I asked Linda how her marriage to Bob was going. "Oh, Hannah I divorced that bastard years ago. He was...

4 years ago
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Forever Her Sissy Chapter 6

This is a work of fiction for your enjoyment and all the characters are fictional. Please practice safe sex, respect others limits and know that bondage and discipline can be dangerous if done to extremes. None of the scenes in this literature are meant to be reproduced in real life. Be respectful to all women and to local ordinances and laws. I Absolutely love reading the reviews that you wonderful readers have been leaving, please, please, please continue to write and post...

2 years ago
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Training Sissy Michelle

I first became aware of "Sissy Michelle" back in the old Craigslist days. She would pop up in the T4M section, advertising herself as an older but very horny sissy looking to serve a group of kinky guys. She said she was interested in all sorts of kinky stuff, everything from group sex to watersports to hypnosis and lots and lots of bondage. She practically begged to be photographed and blackmailed into doing all of this. Here's an example of one of her ads that piqued my...

4 years ago
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Tweak Chapter Four Whats A Sissy To Do

What makes a sissy happy? What makes a sissy's Mistresses happy? It's complicated. Author's note: Although I'm posting this in serial form, I assure you, dear reader, this humble offering consisting of eight chapters, is complete. "Tweak" By: Simonne Danielle © 2008 - 2010 All Rights Reserved Chapter Four - What's A Sissy To Do "You have made your Mistress very happy, sissy Simonne. Let's see if we can't make you just as happy." She led him to the bedroom...

3 years ago
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Cocky Weewee Peepee Sissy Slut Training The Bladder Test

This is one of the sets of stories I am currently writing. The set is called Cocky, Weewee and Peepee Sissy Slut Training. These sissies are in the hands of Mistress Katrina, Mistress Heather and Mistress Satin. Sometimes Master John and Master Rick are involved in their training. Many situations await them. MANY! If these stories succeed I will add some prequels and sequels. Hope you enjoy it! English is not my native language! I will do my best! Sissy Joan Cocky Weewee and...

3 years ago
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The Sissy Diaries My Two Mistresses

Dear Diary, Things were going so good for me. I got promoted at work, even though I know most people there don't like me because I'm quiet and reclusive. It's just that I can't get too close to anyone there and risk exposing that I'm a closeted crossdressing sissy. Still, I do my work and go home to my apartment and escape into my sissy world. Still, I decided that with my promotion and my increase in salary, I could afford a better apartment in a better neighborhood and that's where...

3 years ago
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Good Sissy Girl

Good Sissy Girl. I kept pressing myself backwards. Not much further to go now, I could feel the flare really stretching my lips now and that meant I was almost there. As the plug's biggest width popped past my sphincter and went all the way in I shuddered all over. It felt so full. It felt so good. "That's a good girl. Allll the way in..." my Mistress purred at me. I loved seeing her this excited. I loved turning her on. I loved that transforming myself for her turned her...

4 years ago
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Sissy School Part 3

SISSY SCHOOL - PART 3 By Missy Crystal After Sissy Heather had swished and drooled a couple of more times, she began to give me gentle nibbles and licks to clean the cummy residue on my lips and chin. After the kitty bath, she stood up. Since her crotch was now at my eye level and since her short skirt exposed her frilly panties, it was obvious that I wasn't the only one that got turned on by her sucking my dick. She must have been aware of it too, because she pulled her panties down...

2 years ago
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Sissy tasks

Your First Sissy AssignmentThis is your first step on your journey into femininity. A journey that will change your life. You will be humiliated and embarrassed. Most of all, you will be feminised. If you don’t intend to follow all of these assignments to the letter, then turn away now.Your first assignment is to buy yourself a pair of panties. Be sure to measure your hips before you set off. You will go to a smart department store or, better still, a specialist lingerie shop. How exciting – a...

4 years ago
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She Found a Sissy

She Found a Sissy ? by: Donna Sash She had been working at Bardwell's for the last 10 years. Five years ago she Had moved to the scarf counter and had been there ever since. Sales had gone up because she really likes it here. From the time she was a little girl she always loved wearing a scarf with her outfits. Now every day she wore a different one on the job and it helped sales. Women reacted well to someone who believed in their product. Some women just wore a scarf...

4 years ago
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100 Sissy Points

Author's note. This is a work of erotic fiction, so if this offends you, please stop reading. Also, most of what's described in this story wouldn't be ethical or legal, but again, I remind you that it's fiction! I hope it's good-and-kinky fiction, and while I wish something like this had happened to me, once again, it's only fiction. Some readers think that my stories are autobiographical. I wish! Also, a fan of my work suggested this story concept. Feel free to message me if you have...

4 years ago
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Welcome Your Now a Sissy

Are you ready?Are you ready, princess?It's finally time. It's finally time, princess. It's time to begin. Are you ready? I think you are, princess. I think you're ready. I think you've been ready for so long.You've been ready for your whole life princess.It's time to drop the mask and be who you are. Who you really are. What you really are. No more lies, princess. No more games. It's finally time to reveal everything.It's time to reveal the sissy.That's right, princess. You are a sissy. Say it...

4 years ago
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Femocracy A Sissy Maids Tale

The year is 2050 and women rule the world. I should really follow this statement with a sinister laugh but there was nothing sinister in the current situation. There was no bloody coup by women to overthrow man, there was no war waged by man to wipe himself out, no it was mother nature who took a hand in helping women find there rightful place. Things started changing from the year 2012. Gradually women began to realise that they could read minds. They could easily read the mind of a man...

2 years ago
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A sissy called Jezebel Part II

Part II - Jezebel goes to school, the Templeton Academy: where young womyn become dominatrixes and sissies are crushed into submission. We meet some of hir friends, hir Instructresses, and hir bullies. I exit the gate and head to the main road. We live in a giant gated community, with families that are only 'in the know.' Families that have sissies or otherwise dominate men. A sissy waiting for the school bus, is just something you see. No biggie. One of my neighbors, Dorcas,...

2 years ago
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The 150 Sissy Rules

Rule#1: A sissy does not have a cock. A sissy has a clittyRule#2: A sissy wears a bra and pantiesRule#3: A sissy loves cockRule#4: A sissy loves cumRule#5: A sissy takes it in the assRule#6: A sissy loves pinkRule#7: A sissy loves her toysRule#8: A sissy dresses like a slutRule#9: A sissy sharesRule#10: Sissies love facialsRule#11: A sissy must have a tight assRule#12: A sissy must have perfect bimbo makeupRule#13: A sissy grows big fake titsRule#14: A sissy is a pro cock suckerRule#15: One is...

4 years ago
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407am Sissy

My phone buzzed at 4:07am. I roused myself from sleep to look at the text message because somebody only sends you a message that early in the morning when it's important. I was right. That text message would be the start of a life-changing series of events. It simply read "Good morning, sissy slut." It was followed up by a picture of me, on my knees, wearing a bra, panties and stockings while sucking on a very hard cock. A second picture followed showing my open mouth, filled...

1 year ago
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Milking Sissy

The bondage wasn't necessary. The straps are there really as more of a ritual and now something I took comfort in due to its familiarity. My make up wasn't necessary either. Well, not really. But I no longer face the day without having at least some lipstick on. Thanks to what my Master had tattooed, I usually don't need much more than that. When it's time for my milking however, I like to make sure I'm as pretty as I can be. Especially if my Master decides to make use of me while...

3 years ago
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Unexpected Sissy Transformation

An Unexpected Sissy Transformation My unexpected transformation actually began at the company Christmas party, when Jennifer, our HR Manager of all people, sauntered over to me with an odd smile on her face. "Merry Christmas, Sean," she said, never taking her eyes off my face. "Do you mind if I ask you something personal?" Here we go again. I am an out gay male living in Texas. I can't tell you how many women have quizzed me about my "fabulous" gay lifestyle. The truth of the...

1 year ago
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Sissy and Paul

The double ended dildo had appealed to her sense of humour and made her wet thinking about using it on me. Sissy and Paul Years ago life was very different to nowadays, for a start pubs shut at 10.30 unless they had and extension for special occasions, they had different bars such as the main or public bar, the lounge and sadly no longer, a room called the snug. This room was usually used by the 'older generation' or people who wanted a bit of quiet/privacy. We had married several months...

Mature
3 years ago
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Sissy School Part 6

SISSY SCHOOL - PART 6 By Missy Crystal The sissies flounced out of the kitchen in a train of swirling petticoats and went into the living room, which was also the classroom. I was the caboose, following Sissy Heather. As soon as we were all in the room, Mistress Mary appeared. Either she had ESP or she really was constantly monitoring us. Either way, I was glad I decided not to try anything for the time being. "Today we will have a deportment class," she announced. "Yeth, Mithtwith...

3 years ago
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Sissy Farm Chapter Sixteen

Sissy Farm - Chapter 16 By: Beverly Taff List of Characters. Me: Michelle - A Natural transvestite sissy; Janice: My Younger sister; Aunty Bev: Janice and My mother's Sister; Mistress Janet: Headmistress of the young lady's academy; Dr Shirley: My endocrinologist; Miranda: A very effeminate Sissy sales assistant; Miss Stern: Miranda's mistress who owns the shop; Peregrine: AKA. Uncle Penny. My transvestite uncle, (Aunty Bev's...

3 years ago
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The Reawakening of Sissy Jackson

The Reawakening of Sissy Jackson By Cassandra Morgan The memories came at night, when his consciousness was not on guard to stop them. A little boy, rushing across the playground to his mother. She laughs and picked him up, kisses him on his lips. He is a small boy, frail, too weak to play ball sports with the other kids. He plays on the swings...but not too high. He plays hopscotch. He plays jump rope. The mommy does not care. She likes having her little boy close to him, and if...

3 years ago
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Sissy School Part 4

SISSY SCHOOL - PART 4 By Missy Crystal Mistress Mary came over and stood next to us. To my surprise, her voice was calm. "The purpose of discipline is correction, not cruelty. There is nothing to be gained by punishing a sissy for behavior that cannot be improved and no profit in breaking her spirit by making her fearful of mistakes over which she has no control. I do not require perfection. Only that each sissy tries her best to be perfect. You have always done so, Sissy Heather."...

2 years ago
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My Daily Sissy Schedule Part 1

My Daily Sissy Schedule I met Daddy online a little more than a year ago. He lives about five hours away from me, but promised that despite the distance, he could help me become the perfect sissy slut if only I would agree to follow his schedule for me. I readily agreed, and started down the path to becoming his perfect sissy whore. Here's a peak at my sissy schedule, just in case there are any other sissies out there looking to add a regimen to their life. I wake up every morning...

4 years ago
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Forever Her Sissy Chapter 5

This is a work of fiction for your enjoyment and all the characters are fictional. Please practice safe sex, respect others limits and know that bondage and discipline can be dangerous if done to extremes. None of the scenes in this literature are meant to be reproduced in real life. Be respectful to all women and to local ordinances and laws. Forever Her Sissy - Chapter 5 The ride home was wonderfully uneventful. So many things had happened today, It had been confusing and...

2 years ago
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My Sissy Calling

My Sissy Calling Like many recent college graduates, I found it hard to get a job after I received my super-impressive English degree. Sure, the job market was tough and my degree wasn't going to open any doors, but part of the problem was that I still didn't have any idea about what I wanted to do with the rest of my life. I was looking for a calling--something to give my life meaning. I thought that I would find it in college, but it never came. Well, that's not exactly true. I...

1 year ago
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Sissy Farm Chapter Eleven

Sissy Farm - Chapter Eleven By: Beverly Taff List Of Characters. Me: Michelle - A Natural transvestite sissy. Janice: My Younger sister Aunty Bev: Janice and My mother's Sister. Mistress Janet: Headmistress of the young lady's academy Dr Shirley: My endocrinologist. Miranda: A very effeminate Sissy sales assistant. Miss Stern: Miranda's mistress who owns the shop. Peregrine: AKA. Uncle Penny. My transvestite uncle, (Aunty Bev's brother.) James: AKA. Auntie...

3 years ago
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The Farm School Sissy

INTRO (Skip this bit and get on with the story if you want) Like most of my writing projects this is unfinished. I seem to always get obsessed with small details to the detriment of ever finishing the work. Feel free to take over this story yourself and make it what you will. This particular story is set in a world perhaps just slightly off centre to our own. The location is a boy's only orphan farm school run mostly by strong and independent women. The world has changed in so much...

2 years ago
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Sissy Emma is turned

Sissy Emma is turnedI had been a crossdresser all my life but completely in the closet and hidden from all my friends and family. To ease my tensions, I often chatted with people on line, at first with females and other crossdressers but as I got braver with men as well. I loved to chat with them and their strong demeanour made me feel even more feminine.I had been chatting with John for a couple of weeks, about my fantasies. And let me get this straight, that's all they were fantasies. I mean...

3 years ago
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My Sissy Schedule

Author's Note: Another reader request, this one from a fellow sissy who enjoys when I write about a daily routine that helps keep me in a sissy headspace all day long. She requested that it be detailed enough to seem plausible, should somebody want to start following the schedule. And of course, it should spiral out of control so that her sissy stick throbs in her panties. I'm always happy to oblige. I'm left wondering if I could actually follow such a sissy schedule. It would sure be...

2 years ago
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Forever Her Sissy Chapter 4 of 6

This is a work of fiction for your enjoyment and all the characters are fictional. Please practice safe sex, respect others limits and know that bondage and discipline can be dangerous if done to extremes. None of the scenes in this literature are meant to be reproduced in real life. Be respectful to all women and to local ordinances and laws. Forever Her Sissy - Chapter 4 More shopping? I thought to myself. How much more of this could I take. "Mrs. Karen?" I spoke...

2 years ago
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Crowd Sourced Sissy 3

PREVIOUSLY ON CROWD SOURCED SISSY: In part 1, a man met a sissy exhibitionist while on a trip to New York. She has a website (something like OnlyFans) where her admirers request that she perform kinky acts and tip her for posting videos of her completing these tasks. In part 2, the man decides to become a sissy as well. He travels to New York with visions of sissy in his head, but the anonymous Master who is controlling his fate has other plans for our poor sissy. Crowd Sourced...

4 years ago
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Sissy Farm Chapter Eighteen

Sissy Farm - Chapter 18 - By: Beverly Taff List of Characters. Me: Michelle - A Natural transvestite sissy; Janice: My Younger sister; Aunty Bev: Janice and My mother's Sister; Mistress Janet: Headmistress of the young lady's academy; Dr Shirley: My endocrinologist; Miranda: A very effeminate Sissy sales assistant; Miss Stern: Miranda's mistress who owns the shop; Peregrine: AKA. Uncle Penny. My transvestite uncle, (Aunty Bev's...

2 years ago
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Sissy Hypnosis Fun

Sissy Hypnosis Bet I have always been something of a night owl, which means that I take a while to get up and going in the morning. My alarm generally goes off at 7am, I hit snooze two or three times, then I finally get up and hop in the shower while my coffee pot starts to percolate. I grab my coffee and try to head out the door by 7:45, which is just barely enough time to get me into the office by my 8am start time. Needless to say, I frequently arrive with my hair still wet and...

2 years ago
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Sandys Sissy Maid

Sandy's Sissy Maid By maidboy275 Mistress Sandy had given me a simple order, "When you get up Monday morning get dressed into your pink domestic maid uniform." I knew I needed to do it, I even planed on doing it. Sunday night I had added a new coat of polish to my always polished toenails and then used the deep pink nail polish on my fingernails. I had let it dry in order to be ready first thing Monday morning. I had gone over my body with a razor in the shower and made sure I...

3 years ago
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Online Sissy Training

Online Sissy Training I must admit that I was surprised, but also thrilled to get the email. "Hello Sissy Michelle;" it read. "Please excuse my impertinence in reaching out to you, but I have seen several of your posts on Craigslist, Fetlife and Adult Friend Finder. You always say that you are a sissy seeking dominant men who will train you to become a sissy cum slut. I am guessing that you have not found that man as of yet, because I keep seeing variations on the same ad week...

2 years ago
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A sissy called Jezebel

Part I - Jezebel starts her big day, serving as a sissy maid for the dominant females of hir family. We seen in depth hir morning routine, as sie gets her sisters and hirself ready for school. My alarm goes off at 5:30 in the morning. It is an old fashioned wind up alarm clock with the clapper bell ringer which would wake up the dead, or at least this sissy who had been dreaming sweet dreams of dancing in a full ball gown with hir Prince Charming. I turn on the light on my side...

2 years ago
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Curiosity Spanked the Sissy Finale

You watch Mistress Michele sway towards you provocatively her red lacy worn panties dangling from her finger. Your cock throbs painfully knowing exactly where they are going. Reaching you she takes hold of the dildo and you plead with your eyes for her to remove it. Instead she turns it until the rubber balls are resting against your chin, a wicked smile on her lips. "I never knew what a cock sucker you were..." she smirks and you blush. "I mean ten inches!.You're a pro!..perhaps I...

2 years ago
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Sissy gets a black master

Sissy Gets A Black MasterI got up wearily from my long and exhausting night being fucked andpunished by my new Black Master. As I awoke, I could scarcely believe thatall those depraved things had happened to me. One minute I had been merelyexchanging emails with a man, who could have been anywhere and the nextminute, that very man was at my door, in my home, and then inside mybody. Black Master, a man whose name I didn't even know, a man who lookedto be about ten years my junior, had taken me...

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