Young Sissy Ch. 01

"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...