Young Sissy Ch. 01

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...