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Young Master Ch. 01

By: smittysimon



It was supposed to be the best day of my life...and maybe it was, but definitely not in the way I planned. 

My 21st birthday...my first day as a man, as a true lord of the Manor...my first day as a Master. I was so nervous I threw up my lunch. Not very manly, I know, but just the thought of having my very own sissy to play with had me teetering between the giddy excitement of a kid right about to open the biggest present under the tree, and the stark terror of officially being a man in my step-father's eyes...how could I measure up to him? I felt destined to disappoint him...and I didn't even know why I cared so much. He isn't my real father...he's isn't really my step-father when I think about it. He's only been married to my mother for a year, so I was already a full grown man when I met him...well, not according to him. But that was all going to change today...the door to the study seemed especially heavy as I pulled it open and stepped in to meet my fate...

I should have felt at ease in the study, after all, it was still the house I grew up in, and as an heir to a vast fortune and a name with an unquestionable pedigree, no door was closed to me. I was denied nothing...not until HE came along. Darren Harrow, my step-father, had very different ideas than my mother on what "privileges" I should be allowed. That's what he called them...privileges. Up until then, I considered them part and parcel of my birthright. It was so frustrating to have the door to the study closed to me...to have every door in the house other than my own and the common areas closed to me. Especially after my mother was checked into a "wellness clinic" for "exhaustion". I guess when you're rich enough you don't get put away for pill addiction, you just take a permanent vacation. And with her gone, my step-father wasted no time in filling the house with his living trophies.

It had become something of a secret fad to take beautiful young men and turn them into even more beautiful young women. Of course, they had to keep their most telling trait, or what use would it be to have a sissy without her shameful secret nestled in her panties as a permanent reminder of everything she gave up for a taste of the sweet life. I'd longed for my very own sissy for years, it was the first thing my mother ever denied me...I was beside myself with frustration...how dare she?! I was Byron Templeton III I had fucking Roman Numerals after my name and she was telling me I couldn't have a sissy?! 

I have to admit, as much as I loved mommy, I was glad to see her go once I saw the exotic creatures that took her place. But this too was only a source of frustration, as Darren had very different ideas than I did on what was mine and what was his. Apparently everything my mother owned was his, and all I had was his name. I considered that a very poor bargain...mine was much better than his, but he isn't the sort of man you argue with. So I stood by in tantalized frustration watching as his two older sons, Darius and Dirk, treated the sissies as their own personal chattel. My only consolation was that Dale, the youngest son, was given the same restrictions as me. And I'd show that arrogant little brat who the real man was once I paraded my new sissy around the mansion while he was stuck jerking off for another two years.

So when I stepped through the door to the study, I wasn't just entering a room, I was stepping into a whole new world...a new life...maybe even a new me. I noticed my step-father first, and since the room was littered with the sexiest sissies money could buy, that is saying something. But he's the kind of man that commands your attention. His eyes are the first thing you notice, intense, blazing...with passion or madness I'm still not sure...but once he has you in his gaze, you can't escape. His body seems sculpted to contain such a powerful fire, a strong, brooding brow...a Roman nose, a satyr's smile, and a chiseled jaw that seemed perpetually cocked so that he could look down on you from his impressive six feet. His body was just as awe inspiring, every immaculately tailored suit seemed barely able to contain barely able to contain his frame. Even pushing 50, he exuded the raw animal magnetism of a man half his age, his perfectly coiffed hair blazing like a fire with a few specks of ashen gray. So I wasn't surprised when my gaze turned to him first, looking for the nod of approval to begin selecting my sissy, just as I wasn't surprised to see his eyes travel shortly across my meager five feet of soft slim features and find me wanting. But I swore today was the day that I would prove myself to him and in doing so, to me as well. Of course, before I found myself withering in his gaze the first time, or squirming under the cruel smirks of my step-brothers, I never felt the need to prove anything...but now it was all I thought about.

So when I saw the three angels standing in the middle of the room, I knew I had to pick wisely. A sissy says so much about a man. Looking at the middle child, Dirk, I saw a voluptuous Latina named Lola curled in his lap, sucking lazily on his fingers. Lola had breasts like ripe cantaloupes and an ass that you could set a beer on. I know because it was one of Dirk's favorite party tricks. Dirk had inherited his father's frame, and chiseled good looks, but not the brightness in his eyes. No his where dull and clouded, either with lust or rage, the two emotions he seemed capable of. His sissy was as simple and obvious as he was. And I knew I had to be more than that. I could never be as powerful as Dirk, so I would have to be wiser. That's part of being a man too I figured...

Looking at Darius chilled my blood, his sissy, Cunt, said more about him than I ever wanted to know. He took a Master's right to brand or pierce a sissy's body anyway he sees fit to an art form. Her entire body covered in piercings and intricate barbed wire pattern tattoos trailing to her most tender flesh from her shaved head down to her shaved namesake. One look at the lovingly named Cunt, would tell you all you needed to know about Darius. He didn't inherit the strength his younger brother did, but he still cut an intimidating figure, standing at least six inches taller than his father, with taught solid muscle covering his swimmer's build. His features were more angular, sharp like a blade, and his eyes seemed to stare right through you...you didn't have to look at his sissy to know he was completely without mercy.

I didn't have his capability to inflect horror upon the flesh of an innocent sissy, but I hoped I could show my strength in dominating one without the need for violence. So when I looked over the remaining three, I looked for one with a spark of vitality left, a little wildness I could rein in. Some wild game I could bag and claim as my trophy...

On the right was Bambi, a doe eyed blond bombshell dressed in taffeta and lace, a living porcelain doll with flawless skin, perfectly plump Clara Bow lips, a kissably cute button nose, and lashes that seemed to wave you over, perpetually fluttering over brilliant blue eyes...

She looked like she could be mischievous, maybe even bratty, but I could tell it would only be a pretext to beg for a bare bottom spanking. No, breaking this doll would have been too easy...

The sissy on the left was Sakura, an exotic ladyboy imported from Japan, her sloe eyes always down cast, her ivory smooth cheeks always threatening to break out in a blush, her slender nose leading your eyes to her soft, tiny mouth. I imagined swallowing it in mine, ripping off her school uniform and ravaging her petite, but pleasingly proportioned frame. But that would be even easier than breaking Bambi. Sakura was a fragile blossom, I was almost afraid to stare too intently, worried she might shatter under the weight of my gaze. No, I needed someone stronger, someone like Isabella.

Standing proudly in the middle of the room, Isabella virtually dared you to tame her. A dark haired Italian with face of a Botticelli and body of a tigress. She was at least half a foot taller than me, with soft supple skin only just concealing the taut muscles underneath like snakes hiding under silk sheets. A perfect hourglass shape telling me I'd be spending all my time with her...her eyes blazing almost as brightly as my step-father's, her full haughty lips wearing a similar smirk. I didn't understand how a kept sissy could be so cocky...until I looked down and saw what she kept in her black silk panties. Even soft she was bigger than me...no wonder she walked around in black lingerie while her sissyters hid their shame under skirts. I looked at her and knew she was more woman than I'd ever dreamed of...and maybe more man. I had to break her. My finger trembling, I pointed her out to my step-father, who almost seemed begrudgingly impressed with my choice.

As usual, his booming voice made me flinch, which was hardly the reaction I wanted to have to his announcement "Byron has chosen a slave. Let all present acknowledged that Isabella now belongs to Byron, for so long as he shall have her. Every inch of her body belongs to him, and only he may decide how it shall be used. Anyone that touches his slave without permission will have to answer to me. Is it so agreed?" 

A jarring "YES!" explodes from the crowd in unison, and I jumped a little before I collected myself and walked up to my step-father. My hands shook as I reached for the collar that would claim my prize. "Comport yourself, Byron. You are a man now. Act like one." His words steeled my resolve, with a staggering amount of effort, I managed to still my nerves and look him right in the eyes as I took my collar. It was beautiful...jewel encrusted, it caught the light magically, forming a halo around Isabella's neck as I reached up to clasp it in place, sealing her fate as my slave...and as it turns out, sealing my fate as her master.

There was perfunctory applause as I led her out of the room, first attaching a leash to the golden ring on her collar, and then pulling her out the door. Every step I felt a firm little tug. As if she was telling me that I couldn't budge her if she didn't allow it. I pushed the thought out of my mind. I was in charge here. I fucking OWNED her...and I planned on proving it all night long. The walk to my room was a long, torturous one. My anxious excitement seeming to swell inside me with every step. For a second, I thought I might throw up again, but the sight of Dale's boyish face scrunched up in a jealous pout calmed me down some. He was the runt of the litter, about my height, maybe a little taller, but slender as a reed. I tossed him a friendly shit eating grin, knowing he wouldn't dare talk down to me again after this. With a spring of confidence propelling me forward with each step, I finally reached my door. This was it...no turning back...I had to prove I was just as much a man as this new family that had stolen my birthright.

I opened the door for Isabella and waited impatiently for her to step inside. She just stared at he haughtily, as if she was just barely suppressing laughter. "wuh wuh cough Why aren't you going inside? You are my slave. You have to do what I say." Even after my sputtering start, I'd hoped to sound authoritative, commanding. Instead I ended up sounding plaintive and petulant, but Isabella responded as if she didn't notice. 

"Forgive me, young Master, but a sissy is not permitted to enter the room before a man. However, if you so order, I will dutifully breach this custom for you." Her formal tone belied her bemusement at my ignorance. 

I felt blood rush to my face at dizzying speed, managing to bluster, "I knew that. I was just testing you!" I stormed inside and yanked on her leash with all my might, feeling it go taut in my hand, almost pulling me back. Then I felt it go slack as she decided to step forward. I stood speechless as I stared at her, my mouth slack as I tried to imagine a scenario in which I could tame her. Nothing came to mind, so I decided to wing it and hope for the best, closing the door behind us and locking it tight. Locking her in with me...or was I locking myself in with her? It was all so confusing. I'd always considered myself powerful, because I could get anything I wanted just by asking for it...but now, face to face with desire itself...I felt powerless. She was so beautiful, so confident, so wild...I knew I had to make the first move...but I didn't know what it should be...finally I couldn't stand the tension any longer. I reached up, taking her head in my hands, and pulled her forcefully down into a passionate kiss.

Or at least, I tried too...I ended up pulling her nose down into my eye, making me stumble back onto the floor, hearing her musical laughter fill the room. It sounded like a champagne toast amongst the demons in Hell. I was crestfallen, humiliated, and when crossed over to the room and sat on my bed, her legs spread wide to reveal her silk encased hardness, I was strangely hungry.

"Well, young Master, it appears we have a bit of a problem. It appears you have a perfectly good sissy, and you don't know what to do with her. Or maybe, you know exactly what you want to do with her..." she stood up, then bent over to pull off her panties, slowly, one smooth curvaceous leg at a time, her breasts hanging perilously low, threatening to spill out of her bra any moment. She sat back, down her cock standing proudly at attention. It had to be at least seven inches, twice the size of mine. I'd always tried to tell myself I was "almost average" but looking at this curvaceous concubine with a cock that dwarfed mine, I knew the truth...

"Strip" she said flatly. It wasn't a request. A blush caressed my cheeks as I found myself obeying her without question. I tried to compose myself. After all, I did have to take my clothes off to fuck her...so it wasn't really like I was letting her boss me around...or so I told myself. But when she saw me naked, her laughter cut down any teetering bravado I had left...

"Oh my...isn't that the cutest little thing? Now I know why you picked me. You wanted to see what a real cock looked like, didn't you? Or maybe...what it TASTES like?" She began openly stroking her cock with one hand while holding her panties up in the other, a precious pearl of precum formed on her cock-head. I licked my lips involuntarily, only noticing it when I heard her cruel playful laughter. I buried my face in my hands, wishing I was dead. How could things have gone so terribly wrong? I just wanted to prove I was a real man...and I was proving was that I wasn't as manly as my sissy slave...

"Oh no need to blush. I'm a kept sissy, your private plaything. You don't have to pretend to be a man around me. You can be the delicate little fawn you were born to be. And with a sissy, you never have to feel ashamed. Unless, being degraded by your big dick sissy slave was what you have in mind..." I hear a whimper escape my parted lips, and cup my hand to my mouth to stifle it, but it's too late...

"Ooh looks like I hit the bullseye there. Is that it, would you like me to hit your "bullseye", young Master? Or do you prefer young Mistress?" I squirmed on the floor, feeling smaller and more vulnerable than I ever had before. I couldn't understand it...I didn't want these things...I wanted to be manly, strong...not the soft little fawn I looked like...but when she talked to me like that, I felt something melt inside me, something sweet and sticky and oh so wet...it was like she was putting these ideas in my head, branding them onto my brain, so that they seemed like something I'd wanted all along, but just couldn't admit...

"Tell you what? Why don't I show you how to put on your makeup so you can see how beautiful you really are? And then you can smear your lipstick all over my cock. And if you don't fill my panties with your sissy squirts, I'll even show you how to fuck a sissy so you can feel all tough and butch,"

Every word dripped into my ear like poisoned honey, so sweet, so deadly...I wanted to say no...even Hell no...but all I could manage was "buh buh nuh..." And that didn't seem to convince her of my manliness...

"But I warn you. If you spill so much as a drop of your dirty boi cream inside my silken soft panties, I'll give you the spanking a pampered brat like you has been pining for all your life. And then I'll teach you how to get fucked like a sissy." This was too much...I couldn't let her fuck me...I was the man...the Master. I told myself to walk over there and slap the smile off her face, but when I heard her say..."Ohh the crawling is a nice touch." I knew I was lost...

Suddenly I was staring up at her, her cock looming before me like some profane monument, a monument surrounded by the hills and valleys of Paradise...her balls so smooth and hairless, everything about her seemed soft and inviting, from her long, luscious legs, her torso danced like a velvet python, her breasts swayed hypnotically...every inch of her soft and demure, but hiding a strength that made me tremble and quiver and kneel...

A stinging pain brought tear to my eyes and I hear a loud thunderclap. "Bad sissy! I told you make up first, cock second." I realized with a cringe that my sissy had just slapped the smile off of MY face and that up until a second ago, I had been absent mindedly stroking her cock...I felt so emasculated...so I didn't see the point in fighting it as she led me over to my full length mirror and sat me in a chair. "Close your eyes, I want you to see yourself for the first time, but only when I'm finished."

Her voice had a surprising tenderness to it now, so I meekly accepted her commands, trusting I was in good hands. It seemed like an eternity that my face was teased and tantalized, caressed and covered, my mind imagining what I might look like. Certainly I would look ridiculous, I told myself. Sure, I was short for a man, and I never could seem to grow much in the way of facial hair, but I was still a man. My features weren't that feminine, were they? My light blonde hair might make my down body hair seem nonexistent...but it was there...surely I'd look silly in her clothing, like a boy playing dress up. God, how I wished to look ridiculous..."You can open your eyes now, precious..."

A half choked sob fell from my painted lips, pouty bee-stung lips, now fetchingly glossy and pink. My cherubic cheeks blushing so brightly that the rouge was almost unnecessary. My sea blue eyes wide and wet and suddenly covered in come hither lashes. My scruffy Devil may care hair cut now resembling a cutesy tom boy look, only accentuating what was already so obviously feminine to begin with. Soft, strong hands pulled me up, holding me as I stared in stunned silence as she beckoned me to slip into her soft panties, the silk stirring my already throbbing erection, the lace rubbing maddeningly against the top of my diminutive member. I felt so inadequate standing next to her, and for reasons that were far more frightening. I found my ass almost filled her panties up, and instead of being horrified to learn I had a bubble butt, I was worried she's notice I didn't measure up to her curves. When he bra cups hung empty against my chest, I couldn't help feel insecure about my chest...worse still, what started as curious inspection turned into me pawing myself as I panted in front of the mirror...

"That's enough of that, sissy. If you want to get off over how pretty you look, do it on your own time. I want to see those pretty pink lips drooling all over my cock, not all over your chin." I meekly nodded, embarrassed that I made myself drool and yet also confusingly proud. She pushed lightly but firmly on my shoulders, and I knew what was expected of me. I lowered to my knees, her cock brushing up against my cheek. A slight hint of musk mixing with her intoxicating sweet perfume, making me dizzy and hungry and horny..."It's not a puppy, so don't just cuddle with it. Suck it!"


Young Master Ch. 01



"I...I...I don't know how..." I stammered shamefully, both because I can't please her and because I'm trying to be a good little cocksucker in the first place. But before I can reconsider, she slaps her cock aside my face making me yelp in surprise...

"It's not cocket science! Sigh...little rich bitch hasn't ever had to work a day in her life. I guess it's no surprise you aren't good at anything. Fine, forget it. Just take all of this off and I'll jerk you off or something...Master." I couldn't believe it...I really was a failure at everything...not good enough to be a man...or a sissy. Well, I didn't see much hope in proving myself as a man from this position, and since I was dressed for the part, I dove down to her feet, kissing and suckling her toes, desperate to prove myself as a sissy at least...

"Please, Mistress! I beg you! Please teach me! I promise to listen and I'll do whatever you say!" I looked up hopefully, my fear momentarily overwhelming any fleeting feelings of dignity or self worth. And the answer I saw practically dripping from her lustful look of condescension made it all seem worthwhile.

"Very well. Since you asked so nicely. You can start by giving it a soft kiss on the head and thanking me for letting you suck my beautiful cock..." I stare at it for a second, my mouth watering at the sight of it. I didn't know what to think, did this make me gay? It couldn't, not when it was attached to such a vision of femininity. But I couldn't deny the allure of it...and I had to know...

I closed my eyes and placed a gentle kiss on her cock head. I was surprised at how smooth it was, almost spongy, not nearly as hard as the root appeared to be. It felt so warm and virile against my lips, and before I could even think about it, my tongue darted out of my mouth to slurp of the pearl of precum I'd been coveting for what felt like an eternity. She tasted of an almost pungent saltiness, like some rare cheese or other exotic delicacy. I wondered what was in it that made my heart race and my head swim. I felt almost drunk, but also keyed up beyond belief...it was like I discovered the perfect drug..."Thamph youph!" I mumbled around her cock as I took her head in my mouth and began nursing like a greedy babe, eager for more drops of her nutty nectar. 

I whimpered as she pulled me off her cock by the hair, my tongue thrust out for just one more lick. I looked up at her pleadingly, wondering why she wouldn't let me have my treat..."I didn't tell you to suck it yet, sissy. You have to romance it first. I should punish you for this, but I like your enthusiasm, so I'll let you off with a warning. You are not to so much as breathe on my cock without permission, is that clear?"

I felt so humiliated...but what could I do? Even if she was my sissy, I couldn't exactly order her to let me suck her cock...it just didn't feel right on my tongue. But her cock sure did...and at that moment, I would have said anything to feel it again...."Yes, Mistress! Anything you say!"

"Mmm...Mistress...I like that. Very well, First off, show my adorable little balls some love and suckle one and then the other. Then take your tongue and run it from base to head. Then you may give it another kiss..."

I didn't wait a heartbeat before nuzzling my face between her soft thighs, feeling them hug my face tighter as I took her left ball in my mouth first, sucking it as I ran my tongue slavishly around it trying to taste every inch, to suck up every bit of sweet salty musk..."nnh That's not bad, but try rolling your tongue a little slower...that's better, now work it around my testsissycles in a sloooow circle...ah Good...now the other one..." I listened intently to every word, wanting to be the perfect cocksucker for her. I wasn't sure why I needed her approval so badly, but I knew that it was the first time I had to struggle for anything, and I didn't want to fail. I could feel her cum surging in her sissy sack, I sucked harder, as if I hoped I could drain it right from the source..."ooh Okay, enough of that. Now give my cock a tongue bath..."

I ran my tongue across her scrotum, then up against that comely crevice where her cock met her balls. I slooooowly ran my tongue across the bottom of her prick, savoring every sizzling inch, forcing myself to go slow, to follow instructions when all I wanted was to devour the delicacy that kept tantalizing me with it's robust flavor. When I finally reached her cock, I was rewarded with another drop of her pre-perfection, lapping it up in a passionate french kiss, barely managing to pull myself off so that I could receive my next instructions. "What do I do next, Mistress?"

"Sigh...do I have to explain every little thing to you? Alright, you stupid little sissy. See this here?" She rubbed her cock across my lips drawing a sickly moan, "This is a cock. And this..." she forced her cock past my soft lips pushing a wet whimper back into my mouth, "is your cock hole. The cock..." she pulled her cock out of my mouth, and rubbed it on my lips, bringing me to the verge of tears, "goes in the cock hole..." she pushed in again and I let out a contented sigh as I began sucking her spongy mushroom head in earnest. Until..."And the wetter the cock is, the easier it will slide in and out of the cock hole..." she pulled out one more time, this time slapping my cheek with an embarrassing wet smack. "So slobber all over my cock, you spoiled princess punk ass!" 

I squirmed under her cruel insults, but it only made me more desperate to please her. I ran my tongue up and down her cock, swooning at the taste and texture, falling in love with every vein that throbbed against my tongue, my lips clamped tightly to her flesh giving her horny wet hickeys, hoping any moment she would say..."Hmmph. Well I guess that will have to do." Well that wasn't exactly what I hoped she'd say, but it was close enough. And when she leaned down bringing her lips kissably close to mine, my wildest hopes were exceeded. I just knew lips would taste even better than her cock...and that was saying something. So when she told me to open my mouth, I closed my eyes and waited for my first kiss ever...

"Ptuii" a thick, wet glop of spit hit my tongue and slid down my throat before I could even process what happened. Isabella's less than romantic explanation "Lube." left me reeling. She really was treating me like nothing more than a cockhole. Me, once an heir to a massive fortune, a man no one ever dared say no to, now having his throat lubed by his own personal sissy. So why did it feel like the spit sizzled against my brain? Whirring a mile a minute and ready to blow, I was far too stimulated to make sense of the sensations, much less why they felt so good. And when she said "Now suck my cock, you fucking sissy bitch." I ceased thinking all together...

At first all I could do was fit as much of it in my mouth as possible and suck as hard as I could, running my tongue along every scrumptious inch I could reach. But I realized that she was expecting more than a sloppy suck. I slowed down, moving my head in a corkscrew motion on her cock as I ran my tongue across the head, flicking her pee hole to get at the gooey goodness dripping off of it. I heard a slight moan and felt prouder than I ever had in my life. I moved my tongue below her cock, undulating it against her throbbing member as I took her deeper inside me. And when I heard a full blown whimper, I could have died of happiness. I was starting to work up a good rhythm, enjoying the many ways I could bring her pleasure and draw out her imminent eruption. 

I caught a glimpse of myself in the mirror out of the corner of my eye. A little flat chested, but breathtakingly beautiful, and with my skin shining with a sheen of sweat and reddened with a fetching flush, I looked as fuckable as any cocksucking succubus I ever dreamed up. I felt oddly confident and self assured...that is until she grunted, "Deeper...NNH take it all."

I was afraid she would want that...and I was sure I'd mess it up. I had the worst gag reflex. I don't know what caused it, but even the slightest tickle in my throat made it lurch...but I had to try. I focused all of my attention to her blazing eyes, hoping to borrow the strength in them. I felt her push against the back of my throat, and for a second I felt her hardness slide past my tonsils...then I sputtered and coughed and squelched obscenely...

"Christ...it was barely even in. Spoiled little shit. You finally get me all horned up with a passable blow job, and then you can't even finish me off with your tight throat. Oh God...are you going to cry now? Don't you know there's nothing more annoying than a crying sissy?" 

It's funny, up until that moment, I really was going to cry. Weep even, baby girl bawls were going to tear through my frail frame leaving me a shaking, sobbing, snotty mess. But instead, I pulled myself together enough to say. "No, Mistress. I can do it. See! It's all lubed up now." I cooed, pointing out the sticky strands of snot and spittle coating her cock after I gagged all over it. I didn't know how, and I was almost certain it would kill me, but I had to try...

I gave her beautiful prick a long lingering kiss...for luck, and then I pushed it past my throat, past every natural urge in my body, past every instinct I ever had as a man, past every fear and insecurity and doubt I ever had...and once I got it about halfway down my throat, reality kicked in and I gagged even worse than before. My entire body seized up in paralytic terror...painted tears streamed down my face, and I was sure I was going to die a miserable failure until I heard "nnh Yessss sssooo tight!" 

A shotgun blast of sissy spunk coated my battered throat, calming me immediately as some infantile instinct kicked in and I milked the rest of her cum from her cock with my throat. Through the tears, she shimmered, looking like a living angel, the Goddess of Love. I could feel her orgasm rocket through me, making every loving inch of me shiver and spasm in response. I thought for a second that my throat actually came, and as she pulled out and the oxygen returned to my brain I remembered that it was her cum sliding down my throat, filling me up, pooling in my mouth...

It tasted so much better than the pre-confection, richer and stronger and filled with the ecstatic joy of her release. I think I purred a little when she wiped the last of it on my cheek. It felt like a perfect kiss, hot, wet and lingering long after it's over. I stared up blissed out, blank and still buzzing from the filthy fucked up excitement of it all. She finally broke my reverie, "C minus. Too eager, to obvious, and too shallow. But I can see potential in you. If you pay attention, I can teach you to be a world class cocksucker." I shifted uncomfortably in a mix of shame and pride. Both in only barely making my marks, and in wanting to in the first place. As my cock high faded, all the shame and self recrimination started to come crashing down on me. I had just sucked a cock! And I fucking loved it! That made me a cocksucker...as in forever. How was I ever going to look a man in the face ever again? I was wrestling between never doing this ever again and cursing myself for licking my lips to get one last taste. Finally, Isabella broke through my cloud of confusion, lifting my heads to hers, and giving me a soft kiss on the lips. 

I felt that same spark hit my lips when her cock spread them wide, shorting out my self loathing for a moment and leaving me open mouthed, lost in her eyes. I could have sworn I even saw gentleness in them for a moment when she said..."Now, are you ready to learn how to fuck a sis-" and then the gentleness was vaporized in a white hot blaze..."What the fuck?! Did you cum in my panties?"

I was about to protest, but before I could protest my innocence, she dragged me across the room by my hair, and through the pain and fear, I noticed the stickiness between my legs and felt my gut lurch...

We finally reached a chair across the room. She let go of my hair long enough to sit down, and the white hot needles stabbing at my scalp let up for a moment. I looked up at her tearfully, hopeful for a sign of reprieve...but she just looked at me expectantly. "Well, what are you waiting for? Stand up and take those soiled panties off. It's time for your spanking." I couldn't believe my ears...it all seemed so unreal. How had things gone so wrong so fast? Couldn't I put a stop to this? Even if I was a cocksucker, I was still a man. I was still her master, technically anyway...wasn't I? 

But I didn't feel like her Master...and I didn't feel like a man. I felt like a naughty little boy...and that was being generous...Maybe it was because she was so unflinching, maybe it was because she looked so ravishing when she was furious, or maybe it was just because I had never had a spanking in my life...and I really was due for one. Whatever the reason, I bent over her lap meekly, my ass totally exposed...my heart racing a mile a minute, my cock threatening to stir against her soft creamy skin...I shuddered and pushed the image out of my mind, not wanting to make more trouble for myself. 

"Now, there's nothing more annoying than a sissy that can't control herself when she's being spanked and screams and sobs...but since this is your first time, I'll let you cheat. Here, put this in your mouth..." She handed me my cum stained panties, and with every ounce of me screaming not to, I put it in my mouth. The taste wasn't as exciting now...it tasted like shame and failure. 

I flinched when I felt her hand on my back, which drew a little giggle from her. "A little advice, sweety" she said stroking my ass, making me squirm against her hand..."try not to anticipate the blow too much. If you don't think about..." THWACK!!!

I heard my muffled cry before I felt it, a thunderclap of pain striking my soft sensitive skin. Before I could process this unique and novel sensation of agony, another blow came crashing down. THWACK!!! I bit down on my creamy panties, swallowing a scream sideways. I tried to fight back tears as I feel the throbbing start to sink in from my skin down to my very core...I couldn't imagine enduring another "I know it's your first time, so we'll make it an easy ten..."

I'd never faced such a daunting task, but something told me that if I had to, that it was important...it didn't matter that it didn't make sense, or that I didn't really have a choice in the matter anyway. At that moment, all I cared about was taking my spanking like a man. THWACK!!! THWACK!!! THWACK!!!

Agony is just a word, nothing, nothing in my 21 years of pampered privilege had come close to preparing me for pain on this nature. It was an epiphany of torment. If a spanking hurt this much...what would it feel like if she really decided to hurt me? I realized that I would be powerless to stop her if she did...and somehow, that realization felt freeing somehow. If I was so weak as to be completely outmatched by a sissy, why fight back at all? Why struggle to be a real man when it was so clearly impossible. Why not try to strive for a goal I might actually achieve? I knew that if only I could endure the rest of the spankings, I would have atoned for my transgressions, and I would have proven myself to Isabella...

THWACK!!! THWACK!!! THWACK!!!THWACK!!! Hell rained down a fiery vengeance on my poor innocent ass. I sucked on my panties like a babe, finding some comfort in the creamy taste. I writhed against Isabella's legs, trying to feel some softness, hoping it would dampen the pain that seemed branded permanently into my flesh. I could barely breathe...there wasn't an untouched inch on my tortured tushy. It looked and felt like an overripe tomato ready to burst. I didn't know how I could survive another strike...I just knew I HAD to...

THWACK!!!

It exploded before my eyes, a constellation of brilliant colors danced before me as my mind seized from trying to process the overwhelming rush of sensations flooding it. I felt detached from myself, as if it where someone else writhing on the lap of their sissy slave, begging her for forgiveness, promising to be good from now on...

It was only when I felt her soft hands rubbing lotion onto my cheeks that I started to become aware of my surroundings again. Every nerve was raw and frazzled, making the slightest contact send shivers throughout my body. I couldn't fathom why it felt so good. Was it the adrenaline and endorphins pumping in my veins in response to my torment? Or was it merely the joyous relief that it was over? Maybe I was just proud to have taken my punishment. Whatever it was, I noticed with a blush how hard I was against her soft legs, and then she noticed too, saying, "Ooh it looks like someone needed that spanking more than she new? Have you been waiting for a big strong mommy to make you behave?" 

Of course I wasn't. The very idea was ridiculous...until I heard her whisper it into my ear...and then it seemed so obvious. So...right. It didn't even occur to me to object when she slid a well lubed finger up my virgin asshole... 

"EEP!" a mousy little squeal managed to work its way past my now clean panties much to the delight of my 'mommy'. "Tee hee that's so cuuuuute. My little gurl loves having her pussy fingered does she? She could have been fucking me right now, but instead she was such a naughty slut she couldn't even give a blowjob with out squirting. Or maybe, she wanted to get spanked...maybe she wanted to get FUCKED...is that it pretty gurl, do you want to get fucked?" 

As she teased me with her sing song voice, she did even worse with her finger, sliding it inside me, moving it around causing sharp pangs to bite into me as she stretched my virgin hole. I wanted to tell her to stop, that I didn't like this, but then she found a spot inside me that hit that same spark her cock had hit on my lips, only inside me this time, and much much stronger. Was she right? Did I love it? "NooOOoOooOOOhhhh!"

"Heh heh Well I'll take that as a yes. And if you love one finger, imagine how TWO will feel?" Another finger slid inside me, sending an almost welcome stab of pain. I wanted it to hurt, I'd rather it was agonizing than the shamefully confusing jolts of pleasure. It should have hurt, nothing was supposed to slide up my ass. I was a man, and I was glad that this felt so unnatural, so wrong...but that was until her fingers found that spot again, and doubled the voltage racing to my brain, tickling every inch of my writhing body all the way up to my brain, overloading it, rewiring it, until her fingers felt so right...

"Pleasssse muh muh muh more!" the words fell half formed from my lips, along with my damp panties. I couldn't help myself. I didn't want to want it...but I needed it...she was touching something inside me that I never knew existed...something I knew shouldn't exist, something that filled me with roiling waves of hot shame. But the more she tickled and teased it, the more my asshole started to transform into the pussy she kept calling it. Every nerve came alive, ignoring the pain and drowning the shame in an ocean of boiling bliss. It was so confusing, the only way to escape the shame and doubt was to allow myself to get fucked...to beg for it...to do anything to feel more...

"Well since you asked so nicely..." she added a third finger, laughed as I bucked my hips back to get her deeper inside me, to feel her fuck me faster, harder...wincing past the pain and reveling in the chemical cocktail that took me higher and higher the more I hurt myself to get at the ooey gooey goodness buried inside me. In a way, the spanking had helped, it had stripped me bare, beating down my inhibitions and squeamishness and preparing me for the pain of penetration, planting the pervasive seed that if I accepted my punishment, something beautiful would happen. I felt like my trust was vindicated when she managed to write four of her skilled little fingers inside me, opening me up, readying me for the main course...and then I felt the profound emptiness of an unfilled asshole when she pulled her fingers out and waited for me to beg. I must have held out all of three seconds...




Young Master Ch. 01



"Pluh pluh pleaaasssse...I want your cuh cuh cock!" I struggled to spit out every word, a sloppy stuttering mess, begging to get fucked. So beaten down and horned up that the degrading depravity of it only turned me on even more. She smiled as she peeled me off her lap dragging me back over to the mirror and pushing me down to my knees. She was going to make me watch myself lose my virginity...I closed my eyes to block out the image of the cum splattered sissy, make up ruined, face flush and panting like a bitch in heat, but one glimpse was enough to forever burn the image on my brain...

"Open your eyes, slut. I don't want you to miss a second of this." She grabbed a fistful of my hair and yanked it excruciatingly hard, forcing my eyes wide open so I could watch as she rubbed her cock up and down my ass crack, so I could see my ass as it wriggled hungrily against it, so I could see the face of pure lust and total submission as I surrendered my asshole to her cock. The pain was worse than the spanking...it was punishing me from the inside, where I was much more tender and vulnerable. But her fingers had loosened me up...and once I stopped fighting it, she slid in slowly but without resistance, my pussy wet and ready from her magic fingers. I moaned as she slid further and further into me, never imagining I could take this much inside me. Inch by inch, she opened me up, reshaping my body to fit her cock. All massive seven inches, and at least an inch or so thick. I guess that doesn't seem so big in retrospect, but it was a damn sight bigger than mine, and to my inexperienced hole, it felt MASSIVE.

So when I finally felt her soft hips caressing my sore cheeks, I felt a surge of relief and pride like I'd never experienced before. Starting with that special spot inside me, traveling up my spine, melting it as the electricity coursed up my body, kissing me all over, finally it reached the puddle of bubbling gleeful goo that had replaced my brain, sending back the signal throughout by body in the form of a euphoric birdlike wail, setting my lungs ablaze and traveling to my quivering limbs, dropping me face down on the floor as my body flopped like a dying fish, finally it reached my clit, which blossomed into a flower of paradise, it's nectar coating my legs in spurt after hot hedonistic spurt. 

"Oh my, I haven't even started fucking you and you already came. Hee hee I think I'm going to like being your slave..." she finished her taunts by pulling out slowly, every vein and contour of her cock fucking me in reverse, my pussy clamping down possessively to feel it tighter, harder against me. She must have taken this as her cue, because she thrust back into me, making me wail again, a scream that must have pierced the Heavens and made the angels jealous of my hallelujah fuck high...my earlier orgasm stretched out to one long continuous throb, the pulse of her cock radiating throughout by body, turning it into a sensitive overstimulated clit from the inside out. I was incoherent, giddy, seeing myself for the first time in the mirror and wishing I could fuck the depraved slut staring back at me with glazed eyes and her mouth agape, drooling all over herself like the little animal she was...I realized it was me in the few flashes of sanity I had, but that just made me want to fuck her harder...

I was going insane, my mind, body and soul fucked on a level I had never dreamed possible. I was sputtering nonsense. "Please, fuck me harder, Mommy. I'll be a good girl, just please spank me with your cock, Mistress. Yessss! Mistress! Mommy! Mommy Mistress MommEEEEEEEE!" My Mommy Mistress laughed at my gibberish and pulled me off her cock, giggling as I sobbed for her to put it back in. I cooed like a babe when she sat down and motioned me to sit in her lap, penetrating myself on her cock while she enveloped me in her silky strong arms...

I felt so close to her like this, she was inside me, filling me with her love, but also around me, smothering me in her softness. She kissed my neck, my ears, and finally, when I turned my head to moan appreciatively, full on my open lips. She shoved her tongue down my eager mouth, my own tongue sliding against her as she penetrated my mouth again and again, even as her cock plowed wet sticky spasm after hot throbbing burst inside. Eventually I couldn't take anymore. It was more of a seizure than an orgasm at this point, a true love heart attack, a stroke of luck, as I heard my chest pounding harder and harder, my heart threatening to burst..finally it did, erupting from my clit in a clear stringy explosion, dying and being reborn with every breath as my pussy milked every last drop of her cum from her cock. I collapsed back into her arms, feeling brain dead and beautiful and praying I could hold on to the feeling as long as possible. But even as I tried to drift off into merciful unconsciousness in her arms, I heard the pounding louder than ever. Only I realized I was mistaken before. It wasn't my heart...IT WAS THE DOOR!

"I SAID LET...ME...IN!" CRASH!!! 

The door splintered as it was hurled open...my step-father's massive frame charged into the room, no doubt curious as to why he heard two sissies moaning in my room instead of one. He stood there, his wide shoulders shaking with rage, his face a death mask of hateful disgust. Waiting for me to say something, anything to explain why I was made up like a sissy, sitting on my sissy's cock, coated in her cum...

"I...I...I fell?" Somehow, I don't think it was very convincing...



Young Master Ch. 02



There I was, still impaled on a shemale's cock, one belonging to what was supposed to be my sissy slave, wearing her bra, her cum on my cheek along with my post-fuck smeared make-up, and my cum running down the full length mirror. "I fell" wasn't the best explanation for what happened, but it was all I could think of with my step-father's hulking frame looming over me. I knew I was fucked...well more fucked than already had been, but I still hoped for some miracle to save me. 

"You...fell? I'm not even going to begin to catalog the many reasons that is the most insultingly stupid lie I have ever heard. I'll give you one more chance to tell me the truth, and then I'll ask Isabella. And, Byron, you had better believe she will tell me the truth, so lie at your own peril."

I didn't know what to tell him. I was so ashamed, every doubt and reservation I had before my mind seemed to shut down came screaming back at me. I just wanted to crawl in a hole and hide from his contemptuous eyes forever. But I knew I couldn't hide from those blazing eyes; they'd scorch the earth to find me, and when they did...I shuddered to think of the countless ways he could hurt me, and my entire shameful story came spilling out...

I tried to explain it in a way that didn't paint me as a natural born sissy, tried to explain that all I wanted to do was to prove I was a real man, but it's hard to do when explaining how your personal sissy slut seduced you, sissied you up, mouth fucked you, spanked you, fingered you, and fucked the cum out of you. What I finally managed to stammer out as a final, flimsy explanation was "I'm sorry...she's just so much more experienced than me. I shouldn't have let her trick me...but I swear, none of this was my idea and I never would have done any of it if she hadn't gotten me so mixed up." 

As excuses go, it was pretty pathetic, and it didn't exactly make me a candidate for man of the year, but at least it didn't paint me as the sissiest sissy that ever sissied, and I hoped that might be enough. Even I could believe it if I tried hard enough. All that was left to do was wait and see if this immovable mass of malice would accept it. "Well, Isabella, is this true? Was this your doing?"

She had already slipped out of me and crawled over to his feet, curled up around his legs like a kitten. I wondered where this submissiveness was when I needed it most, but mostly I wondered if she'd sell me out to save her own downy soft skin..."Yes, Master. I seduced the confused little virgin, and it was sooooo easy. I know it was bad, but please forgive me, Master. He's just so cuuuuute." 

I heaved a sigh of relief that quickly turned into a horrified gasp as my step-father savagely kicked Isabella in the stomach, knocking the breath out of her and making her curl up into a tight little ball of pain. I tried to say something, to beg him to stop, to tell him it wasn't really her fault, anything to stop him from hurting her. But I couldn't breathe. Finally I saw her stirring again, looking up at him with a manic smile, her eyes glazed over with lust..."Thank you for punishing this worthless slave, Master. Please, hurt me some more...I deserve to be punished." 

It was so strange...this was the same sissy that had me completely twisted around her little finger...and then shoved it up my ass. But around Darren, she seemed to get off on being slapped around and put in her place. Is that why she teased and toyed with me? Was she just fucking with me to get me to push back? I started looking at her in a whole new light, and from the perspective she wasn't quite so cute. Maybe it was just easier to blame her than to accept what I let her do to me, but anger felt so much better than guilt, so I nursed on it like a baby...

"Hmm...Normally I'd have both of you in stocks for a week with a fuck machine pounding your ass the entire time. But perhaps you have a point, Byron. Isabella was just being Isabella, and maybe I could have done more to prepare you for the world of Men. So I'll let this pass this one time and we shall never speak of it again. But I warn you Byron, by marriage or blood, I will have no sissy carry my name. Do you understand?" His rage seemed to have tempered, but that just left him rigid as cast steel. It was all I could do to nod without shivering.

"Good, because you know I don't like to repeat myself. Now, I want you to pay close attention, because I am about to teach you how to keep your sissy in line." His tone was just as calm as if he were talking about changing the oil, and with the same casual authority, he pulled Isabella up by her hair until she had to stand on her tippy toes to avoid being lifted into the air by her thick, luxurious locks. He pulled her into a savage kiss, practically swallowing her mouth with his. There was no affection in it, no romance; he was merely claiming her mouth as his own personal hole. And for her part, she seemed all too willing to surrender it, her eyes rolling back in her head as she passively accepted him raping her mouth...

I heard a pathetic little yelp as he dropped her to the ground, saw her crumpled on the floor as she looked up at him with slavish devotion. I knew I couldn't toss her around like Darren could, she was taller than me and everything. But as I saw her running her tongue over his wingtips, sucking on the tips, her eyes glued to his the entire time, I knew I wanted to make her do the same to me. I wanted to make her pay...and I wasn't going to miss a single second of this hands-on demonstration on exactly how to do it...

"You're sucking the wrong tip, bitch." He pulls her up by her hair again, twisting it in his hand so that she can't budge with out losing a fistful of hair right from her sensitive scalp. With her lips right at the top of his pants, he says, "Your smart mouth got you into this trouble, let's see if it's smart enough to get you out." I stared in perplexed nervousness wondering how she could possibly free his cock using just her mouth. I almost started feeling sorry for her. I know she probably would have been giggling if our roles were reversed, but I just get squeamish when I see someone in pain. Maybe because I can't help but imagine what it would feel like. I held my breath, hoping for a miracle...

"The fuck..." I closed my hand over my mouth, not wanting to interrupt with another outburst. But I could barely contain myself. She was using her teeth to bite the slack of his belt and moving her head ever so slightly to work it out a little bit at a time. I couldn't stifle a gasp as she finally got it loose, but my step-father seemed unimpressed...

"Today would be nice." he said with a yawn. I couldn't believe it, this was the hottest, most submissive human pet trick I'd ever seen, and he was treating it like it was chore to watch. Again I felt sorry for her against my better judgment, hoping he'd acknowledge her skill as she bit down on the button of his pants and worked it through the eyelet by tilting her head. But he just looked at her with frustrated boredom. Finally she took the zipper in her teeth, whimpering as she tried to move her head down just a little further, just far enough to free his cock, but he wouldn't give her an inch...or twelve as the case may be. 

She looked up in desperation, surrendering her pride once more as she begged, "Please, Master, please move my stupid whore head down so I can get to your cock. I'm too weak and pathetic to do it on my own." She had the look of one who had to deliver this speech many times before. I wondered how she still kept the fire in her eyes when my step-father doused her flame with his callous games. I was remembering why I hated him, why I feared him...why I'd do anything to prove myself to him. And when I saw him move her head down with the zipper in her teeth as casual as if he were just unzipping his pants, I understood the hopeless frustration Isabella must have been feeling at that moment...

When she finally manage to unzip him, his cock sprang forth like a wild beast. I couldn't believe it...I never knew they could come that big...that thick...I don't know how he could get a hard on that size and not pass out from the loss of blood flow to his brain. Hell...I felt lightheaded just looking at it. She seemed to be in a daze too, her mouth open so wide it looked like her jaw had come unhinged. And then without a moment's notice, he crammed it in her throat, burying at least six inches down her gullet in one ravaging thrust. 

I held my hand to my throat, remembering how rough a few inches had felt, unable to stop myself from imagining what it would be like in her place...She gagged on his cock, even her well practiced throat unable to take his full length dry. 'Luckily', her spit seemed to make the second thrust a little easier, she managed to get two thirds of his massive member before choking helplessly. This time he held her in place until her face turned red, her eyes rolling back in her head...he snapped her out of it with a hard cockslap to her face, and I couldn't help but imagine myself moaning as I drooled all over myself just like she did...I shuddered as I realized what I was imagining, and tried to force it from my mind...

Instead I tried to imagine myself as my step-father, now managing to bottom out in her throat, and then yanking her off me by her hair, holding her just out of reach as she tried to get back on it, the veins in her neck looking like they would burst any minute...and then slamming her right back onto it. Before long it was a sloppy blur of spit and hair bobbing back and forth on his prick. But try as I might, I couldn't see myself doing that to anyone, even to the sissy that used and abused me. And even if I could manage to keep her in line long enough to force her to suck my cock, even if I ignored how much stronger she was than me, what would be the point? Is forcing three and a half inches of hard meat really that demeaning? Honestly I think it would just make her laugh...

But she wasn't laughing at Darren, she was too drunk off her own humiliation. I didn't get it...even though I was the same way with her. Why would anyone want to be treated that way? To be used like a cock sleeve? To hear my step-father call me "A cock sucking sissy bitch, a cunt mouth whore, that's it, fuck hole, get ready for my seed." I mean...call her that...I got a little caught up in the moment. And when he finally pulled her off and exploded in her face, coating her with a thick layer of white mucousy shame, I had to bite my lower lip to prevent from whimpering along with her. 

My step-father looked right at me, but it felt more like he was looking inside me, judging me silently. I opened my mouth to say something in my defense, but I didn't even know what I had been accused of. Either way, nothing came out but a raspy breath. After an eternity of crushing silence, he said. "So you see how you are supposed to get a blowjob from a sissy. First and foremost, they should be the ones with a face full of cum. And that's just the warm up..."

Isabella was hungrily sucking his balls as he gave me his lesson on Master/sissy etiquette. She was clearly trying to get him hard again as soon as possible, but I didn't see how that could be. If I sprayed that much cum, I'd be dry for a week. Even with all the squirting I'd done today, it wasn't half of his giant load. But to my everlasting horror, his cock managed to rise in defiance of gravity and all that is holy. Apparently, I was the only one surprised, as Isabella didn't blink before turning around and hiking her ass in the air, wiggling it invitingly...I imagined how lucky I would feel to be in his shoes right now, to see someone as beautiful and confident as Isabella offering herself to me so completely like that.

I guess he didn't feel so lucky, as he kicked her hard in the ass, sending her in a tumbled heap onto the floor, just barely managing to keep wet, jagged sobs at bay. "Undress me, you vapid cunt." I would have killed him if he did that to me...well, I would have wanted to. But Isabella just looked up totally apologetic and wasted no time pulling his clothes off and neatly folding them before setting them aside. I guess it's easier to feel guilty than angry after all, especially if the man you'd feel angry at could snuff you out like a candle. If anything, that impotent rage would only make me angrier at myself for being too weak to stop him. No, I'd much rather convince myself I was wrong and work tirelessly to make it up to him...if I was her I mean.

When he was completely nude, I couldn't help but notice his physique. He had the body of a man half his age, if that man had a great fucking body anyway. He was tall and wide, but virtually every inch of it was covered in taut, bulging muscle. The only exception was a little looseness here and there, as time couldn't be beaten down entirely. If anything, these minor imperfections merely added to his appeal, as it gave him the kind of august authority of an elder statesman. He had nothing to prove...he had already forgotten more conquests than I ever dreamed of having. Every little detail, from the wry wrinkles around the corner of his eyes, to the salt peppered in his lush mane of chest hair, all of it painted the portrait of a living legend. Not that I notice those kinds of things, but when it stared me in the face, I just called it like I saw it.

He lifted her into the air like she was weightless, and I realized with a blush that he could lift me even easier. She squealed with girlish glee at the gravity-defying rush of total helplessness. And then he shattered her illusion, showing her the full weight of gravity as he let her sink down onto his cock, moaning incoherently all the way until she nestled at the root, her arms were flung around his neck, her legs wrapped around his hips. She had more Real Man inside her ass than I had inside of my entire body, and of the two of them, it only made sense to put myself in her place. After all, I'd never been balls deep inside a sissy, but I had felt my asshole stretch and surrender to a superior cock, enduring the pain, then ignoring it, and finally worshiping it, knowing it brought the exquisite explosions of pleasure along with it. 

But this...this was a cock of a whole different breed. This was no sissy cock like I had been so impressed with earlier, this was a Real Man's cock, and I just knew it would kill me if I ever tried to slide up and down it in a furious flurry of whimpers, moans, and wet smacking the way Isabella was. Not that she had any choice, the way my step-father manhandled her, she was little more than a cum-rag doll for him to play with. But even though she was being used with no regard to her comfort or pleasure, I could tell she wouldn't give it up for the world. Maybe it was because she had no choice in the matter. If she really had just held me down and raped me, would I feel so stomach-churningly guilty about it as I did right then? Or would I feel freed from all guilt and responsibility by the powerful arms of my step-father? Using me so savagely, forcing me to love it, enslaving me in his embrace, freeing me from reason and dignity and manhood, making me a thing, not even a sissy really, just a long continuous screaming orgasm. My head was swimming, I couldn't stop 'sympathizing' with her, but I knew I had to try. I had to think about fucking her instead. "Ha, I can see you like this, boy. Alright, come over here and get a closer look. I want you to see her face when she offers her soul to me."

He put her on the ground and flipped her over unceremoniously. He lifted her ass in the air and spread her legs as far as they would go. He didn't even have to tell her to hold her ass cheeks apart. I saw her now gaping hole and wondered if I could survive feeling that empty. And when I got down on my knees in front of her and he began fucking her in earnest once again, I wondered if I could ever survive being that full. Even an experienced sissy like Isabella looked like she had trouble taking it. In a way, I suppose she didn't survive. Her eyes went totally blank, her mouth started dribbling gibberish, and I could see the soul get fucked out of her body. She was just a fuck husk now, and there wasn't even enough left of her to tell me how much she obviously loved it. That was the part that scared me the most. What happens after you die? That's the easy part, it's coming back to life that's scary. It's like bringing back demons from Hell clinging to you, corrupting me, damning me forever to see the world through a bitch's eyes. To have an asshole that twitches and aches when it sees a fat cock. To feel an emptiness where I know nothing should go in the first place. To watch the most beautiful creature I've ever seen get the life fucked out of her and to be reborn in a newborn wail of ecstasy, and to cover her face in cum as I jerked my tiny nub, dreaming of being her...

"That's more like it, stud, cover that sissy's face with cum. Show her who's boss. Unh unh FUCK!" Every muscle in his body surged as he emptied a gallon of jism inside her burning cock hole. Her own cock jumped around like a fire-hose that got away from the Firemen, spraying ribbons of cum all over her legs and stomach. I fell back, spent. Cursing myself, cursing my step-father, but most of all, cursing Isabella. I remembered my anger now and I vowed never again would I feel sorry for her or put myself in her shoes.

"The important thing to remember, is that whether your cock is too big or ahem....too small, with sissies it doesn't matter. They exist for your pleasure. And if you show them confidence and inner strength, they will surrender gratefully. Do you understand now, Byron?" He looked at me expectantly, patiently even. I almost fooled myself into seeing embers of kindness glowing in his eyes as well.

I took a deep breath and steeled myself. Confidently as I've ever said anything, I replied, "Yes, sir. I've learned my lesson and then some. I can't wait to show this bitch who's boss." I felt an angry energy building inside me, and at that moment, I really believed I could be a Master after all.

"Good, because now I want you to get cleaned up, put on some normal clothes, and follow me. I'm going to show you what's behind door number two. I'm going to show you what it's really like to be a trophy sissy."

I was a little perplexed by his ominous tone. I thought I already knew what it was like to be a trophy sissy. Honestly it wasn't much different from the life I already had. You got to lay around all day doing nothing, enjoying all the luxuries someone else has striven so hard to work for. About the only differences I could see was you didn't get to leave the premises unescorted and you got fucked all the time. Still I was doing a pretty good job of convincing myself that last part was a bad thing. And as I looked at myself in the mirror, having just washed my face of the make up and cum, I vowed once again to find a way to prove my manhood. 

"I don't have all day, Byron. Unlike yours, my time is actually worth something." I jumped in a rather unmanly fashion as his voice bursts through the door and hurriedly get dressed in a plain white button up shirts and khaki slacks. I didn't want anything too colorful sending the wrong message. I gave myself one last pep talk and emerged from the restroom with my head held high. Well as high as I could at five feet three inches. 

"Finally. Now don't dawdle. Byron. We'll start off by showing you the sissy's quarters." I nodded, resolutely I hope, and followed my step-father, with Isabella trailing closely behind. Her perfume teased my nostrils, reminding me of her tantalizing taste, but I shook the image from my head and focused on our little tour instead. I was perplexed, we had already passed all of the guest wings, and each of my brother's personal wings. The rest of the grounds were common rooms and I couldn't figure out where we were heading. When we finally reached the door to the basement, my heart stopped.




Young Master Ch. 02



"Why do you look so surprised, boy? Surely you didn't think we let sissies live upstairs with us. Some liberal, lawless households might allow that, but most men of means recognize that a sissy's place is out of sight until their services are required. The only way they can come upstairs is during designated walks or if a Master calls on their services. Sissies like Isabella, Cunt and Lola can stay in their Master's room at his discretion, but a good Master doesn't spoil his sissy with too much attention or comfort." Every word hit like a nail on my coffin, burying me alive as I entered the dark, claustrophobic corridor. I had always been terrified of the basement; it was the one part of the house no one ever had to bar me from. But I didn't want Darren to see me shiver or to know about my fear of the dark and tight spaces. I held my breath, counting each step as I tried not to imagine living down here, finally able to exhale when we got down to a more open area and he turned on the lights...

"Gasp!" My relief was short lived as the sight of the 'sissy foyer' loomed before me. Cages hung on the walls...enough to house an army of sissies. Sleeping snugly in the cages were all of the family's sissies save for Cunt, and if she was with Darius, I'd almost rather be locked up. Isabella smiled wickedly at me, as if to say 'Like what you see?'...

"As a Master this room is your own personal candy store. You can select as many unowned sissies as you'd like and let them loose. You can imagine how grateful they will be for your attention. As a sissy however, it is a long torturous grind of dull nothingness. But don't feel too bad for them, we do allow them plenty of playtime during the day as well." He leads me down another corridor, plain white walls and halogen lighting giving it the air of an abandoned hospital, or a morgue. Finally I come to a large open room, filled with stocks, locks, and a barrel of fun...if you were the Marque de Sade. There were chains hanging from the ceiling, attached to the walls, and bolted down to the floors. Everywhere I turned there was another more painful looking device to hold me firmly, leaving me helpless and exposed to any pleasure or pain anyone might capriciously inflict upon me. "This is the playroom. If they are good gurls, we let them play with the toys on their own. If they are bad gurls, well...I don't think you're quite ready for that image. We wouldn't want to disturb your beauty sleep."

He leads me to another room, almost as big as the playroom, this one filled with exercise equipment. I suddenly realized how the sissies kept so perfectly fit. God, they must have to exercise an hour a day. A month's worth would be more than I'd exerted in my entire life. "The sissies are expected to keep in perfect shape, as decided by their owners. They exercise a good four hours a day, every day, well except Christmas of course. We only make them exercise two hours on the holidays. We aren't monsters after all." I thought I might collapse from the strain of just imagining all that effort. I was feeling more and more lightheaded, the tour taking the shape of a waking nightmare. The walls seemed to be sliding closer and closer, the lights dimming...I prayed silently that the tour was almost over...

"The tour is almost over, which should tell you something about the spartan simplicity of a sissy's life. Only two more stops. First, on your left you'll see the shower room. Communal of course." I hear an evil giggle from behind me and I know I never want to be in those showers surrounded by a bunch of frustrated sissies looking to blow off some steam. "And on the right, is our world class cafeteria." 

I step inside the plain room. A few tables with benches are bolted to the ground. I follow him back to the kitchen where I see giant pots warming on the stove. "Now you might have imagined sissies dining on the same delicacies you regularly enjoy. And to be sure, when entertaining at parties or serving their master, they might get to enjoy sucking the scraps from a man's fingers. But in order to keep within their desired weights and figures, they eat from these." I noticed the pots all had names engraved in them, no doubt with different dietary supplements and who knows what else. I looked at the gray paste like texture and smelled the smell of sour oats and couldn't keep from gagging a little. 

"Now you see what a sissy's life is truly like. And this is just the tip of the iceberg. They live to please others and the only pleasure they get is in service to that goal. But don't think I showed you this to give you some misguided sympathy for them. They are pets, toys, holes...and if I EVER see you getting used like a sissy cum dump again," He pulled me by my shirt so I'm at eye level, my feet dangling just above the ground, "then this will be your new home. I don't care who you think you are. Trust me, I can make you disappear. And no one will bat an eye at the vaguely familiar looking new addition to my harem. Is that understood, boy?" He dropped me to the ground, sending me sprawling into Isabella's waiting arms...

"I...uh...yes...I mean, yes, sir, I understand." He simply nodded and walked off, leaving me down in the dark with my new pet. My mind reeling as I tried to process all I'd just seen and heard. I couldn't let this happen to me...I wouldn't. I would ignore the heart wrenching empathy I felt towards Isabella and force myself to treat her the way she seemed to want to be treated. I sighed as she stroked my hair, holding my tight against her...

"You heard him, Master. If you get caught sucking my cock or taking it up that tight little ass again, you'll be one of us." Hearing it from her lips made it sound even more terrifying. I wanted nothing more than to run from her tender touch and never see her again. But I didn't know my way back on my own. Besides, she seemed to understand my predicament so I figured she wouldn't try the same tricks on me twice...that is, until she started sucking softly on my ear, flicking her tongue in and out of it before whispering, "So we'll just have to make sure we don't get caught..."

I felt her erection pressing up against my cheeks...I struggled to sound forceful, to respond with an unwavering refusal, to put her in her place, but all that came out was..."whimper."



Young Master Ch. 03



"That's a good little, sissy. I told you that you could take the whole thing." I feel a sense of ashamed accomplishment as her smooth balls rest on my chin and I smell her intoxicating mix of pomegranate and a hint of musk as my nose crushes into her flawless, taut torso. This was the last time. It had to be. We couldn't keep sneaking around waiting for a chance for a furtive fuck or speedy suck. And if I got caught...no, I didn't even want to imagine what it would be like to be stuck in that sissy hell down in the basement. At least not until after I came inside her pretty lace panties...and then never again...

Of course, I had promised myself that before. The first time was when my step-father left me alone with her in an eerily quiet basement after giving me a guided tour of Hell. His words still rang in my ears even as she whispered dirty nothings inside them. It all whirled together, "Get caught sucking or getting fucked one more time, and you'll end up another sissy in my harem...so we better not get caught. One more time...suck and fuck...one more time..." I relented, the fear and tension of the day breaking down my resolve, making me desperate for the escape of pure animal lust. She pulled my pants down and pinned me to the wall, my ass still well lubed with her earlier deposit. Then she fucked me hard against the wall, each thrust squishing my little cock against the even harder brick squeezing the cum out of it like a roll of toothpaste, my girly moans echoing throughout the halls even as my orgasm echoed inside me, bouncing back and forth as she continued to pound my ass, more concerned with her own release than with my dick dumb drooling state of cock induced catatonia. When she finally erupted in my ass, I felt like I had burst free from that terrifying underworld and exploded into the heavens. 

When I came down, she was sucking the last remnants of her cum from my ass even as I sobbed shamefully. "Don't worry your pretty little head about it, Master. I'm just getting rid of the evidence." I blushed as I saw my cum staining the pure white walls, and realized I had to get rid of some evidence of my own, licking them clean with a piggish grunt. I knew I shouldn't have, but I told myself since it was going to be the last time, I might as well enjoy it. So when Isabella told me to open my mouth and fed me the rest of her cum baby bird style before thrusting her tongue inside my mouth and painting my lips, tongue, and the back of my throat with it, I just cooed...But after I pulled myself together and silently followed Isabella back upstairs where I belonged, I swore to myself that I would never do that ever again...

I felt better once I got out of the basement. I was sure I never would have let her take advantage of me like that if I wasn't so nervous and out of sorts. I decided I would bring Isabella back up to my room and fuck the shit out of her. I had an extra spring in my step as I led her back up to my room and closed the door behind us. It felt a little strange not being able to lock it since my step-father busted it, but in a strange way, it kind of bolstered my spirits imagining that someone might walk in on me fucking her this time. I even managed a little sneer when I told her to strip for me, remembering the cocky little bastard I used to be before my step-father moved in and made me feel like a weak little boy.

When she was completely naked, I marveled at her beauty, as if seeing her again for the first time. She looked so different when I wasn't staring up at her, and mischievous smirk or no, I knew I could put her in her place. I told her to get on her knees and suck my cock, and she giggled a little as she lunged for it. She was treating it like a kinky little game, but I told myself it was one I would win. All I had to do was bust a nut in her face and then one in her ass and I'd restore the natural order...of course, I would have had been able to get an erection for that to work.

It was so frustrating to feel her lips on my soft skin, to shudder at their touch, but to feel nothing stirring down below. I blamed it on nerves, on exhaustion, on having cum more in one day than I ever had before...on her. That emasculating little giggle, sure it was her fault. Even now I can see that. Just another one of her games. I told myself that he who laughs last, lasts best and decided to turn in early, telling her that she'd better wake me with a blow-job if she knew what was good for her. It didn't take long for me to slip into a troubled fitful sleep, populated by nightmarish visions of life in the basement. The last coherent thought I had before tumbling into unconsciousness was that next week would be different...

Monday

Just before waking, I had a more pleasant dream than the nightmares of sissy slavery, but in a way, it was much more frightening. In it, I was giving Isabella a long, loving blow-job, more making out with the cock than anything, and I felt safe and free. Somehow I knew no one would find out about it, and somehow I knew there was nothing wrong with enjoying it. It felt so real...I could taste her on my tongue, feel her cock-head kiss my lips sending sparks all across my body, I could even breathe in her smell, making me too dizzy to care about the greater symbolism of sucking off my sissy in a dream. I'm sure Freud would say it represented unresolved feelings of abandonment, but sometimes a sissy cock is just a sissy cock. It was all so real...by the time I realized it wasn't a dream, I could feel her ready to explode inside my mouth, so I figured what the fuck, why stop short of the finish line. 

I felt the bottom of her cock throb against my tongue and I knew what was cumming. Worse still...I wanted it...needed it even. In that single moment I needed it more than my dignity, my manhood, or my freedom. I felt a wet burst inside my mouth as she unleashed a full load into my ravenous maw. I felt it tingling on my tongue, the taste again reminding me of some half remembered exotic delicacy, not a cheese, no maybe morels? I wanted to savor it on my tongue, but my mouth was filling up too fast to hold it all. I tried to swallow it all as quickly as I could, but there was too much and it began to drool down my chin. Before I could even whimper in lustful shame, Isabella was lapping it up and feeding it back to me with her soft, sensuous tongue. I sucked her tongue clean only to feel more cum running down my cheeks. Now I had plenty of time to whimper...and moan...and pant breathlessly as she slid her tongue across my flushed face and shared her cum with me until I was all clean, but feeling dirtier than ever.

When she finally rolled off of me, I was left reeling. It was a good thing I was already in bed, because after that, I probably would have collapsed anyway. I still couldn't fathom how her cum could make me feel so good. Some kind of strange chemical reaction was occurring, but I didn't know if it was her cum or my brain that was to blame. It caused the strangest mix of drunken alertness. It was more exhilarating than a hot cup of coffee followed by a shot of brandy, making me feel light and frisky and filled with mindless giddy glee. 

But it was a double edged sword, as the alertness brought a rush of self recriminations with it, and the dick dazed haze leaving me unable to put together the pieces of my shattered psyche. My mind was like a dog chasing its tail, racing in circles, snapping at itself, feeling more frustrated and confused with each passing moment. I went from high to low in a few breaths and I was beginning to understand that if her cock was a drug, then the cum down would be a bitch. And to make things worse, I had to change underwear. Sucking her cock had made me cum again, and I was so lost in the dreamy moment, I hadn't even noticed it. But Isabella sure did, "Aww, you came for me again. That is so cuuuuute. I thought this might happen, so I sneaked out while you were sleeping last night...oh and by the way, I loooooove that you still suck your thumb...and just look what I got for you!"

She held up a pair of ivory colored silk panties, with a cute little boy-cut design. She looked at me expectantly, as if I was supposed to eagerly snatch them out of her hand and put them on with a sissy squeal of delight. I guess I couldn't blame her for thinking that, but that only pissed me off more. "Let's get something straight, Isabella. I am a man. And I am your Master. So you need to start treating me like it." I tried to keep my voice steady and my eyes cold and hard. Even I was a little impressed with how hard I sounded...

"You've got a little..." she wipes a bit of cum she must have missed with her tongue and sucks her finger clean. I blush and shrink into myself, just hoping she'll leave me be, but I'm not that lucky. She began nibbling on my neck and teasing my nipples. This was an awful time to find out I have sensitive nipples and that when someone sucks on my neck it makes me moan involuntarily. "Pleassssse. Master? I only want to make you happy. And I know wearing my panties all day will make you happy. I felt so bad for you last night when you...well, you know...So I thought if you wore these all day, you'd be so frustrated and pent up by bedtime that you could fuck me for hours. You know, really put me in my place..." She punctuated her little speech my taking one of my nipples in her mouth and sucking on it hard, rapidly flicking her tongue across it like it was the head of my cock...

Deep down I knew she was toying with me, I mean, she wasn't even being clever about it. I think that's why I agreed to put on her panties again, I wanted to beat her at her own game. I wanted to wear them all day, and instead of begging her to fuck me at the end of the night like she expected, I'd have her begging me to fuck her. And besides, they were boy shorts, so they were almost men's underwear.

I told her that I needed some "me time" but gave her permission to roam the estate. I just couldn't imagine sending her down to the basement after I'd seen what it was really like, but I knew that if I let her follow me around all day, she'd find someway to get me in trouble. I felt a little more at ease when I saw her walk away, and boy, I could watch her walk away for hours. But it didn't take long for me to realize she already had gotten me in trouble. I was kicking myself for letting her talk me into wearing her panties. Every step was a maddening caress to my tightly hugged cock. I felt conspicuous and was sure someone could see the outline of her panties under my slacks. It was bad enough wondering who knew about my little sissy snafu, now I had to worry that they knew I was still on her hook. And what if my step-father found out?! I'd be back down in the basement, but this time to stay...

Luckily my step-brothers greeted me with their usual contemptuous indifference. I know they would never let me hear the end of it if they knew the truth, so Darren must have been good to his word and kept my sissy secret. That made me want to prove myself even more. If I could just find a way to tame Isabella, it would be like this shameful saga never took place. I took a deep breath and then made another solemn vow to walk the straight and narrow path to manhood...and then I took my first step and a silky swish almost made me double me over as a result of frustrated friction. 

I managed to make it until noon with out losing my cool, although I'm not sure if cold sweats count as keeping my cool, but I guess it does on a technicality at least. That's when I saw Bambi, skipping along without a care in the world...and I mean literally skipping. Who even skips anymore? I realized I could make up for my poor choice in my pet sissy then and there. She might not have been my personal property, but as a house sissy, any Master could take her anytime he wanted. And I wanted...I wanted very badly. I followed her out to the garden, where she was actually smelling flowers and swooning. I'd never seen anything so girly in all my life. But my attention soon turned to her more mature attributes, the way her short baby blue party dress lifted up as she bent all the way from the waist to stop and smell the roses. Her white ruffled stockings drew my eyes up to her ruffled rumba shorts. I was a little proud of myself that instead of wondering what they would look like on me, I wondered what the cute little rosebud hiding between her cheeks smelled like.

I made my over to her with an exaggerated swagger, psyching myself up before taking one of her perfectly plump ass cheeks in hand and squeezing it. She jumped up with the most adorable little yelp, and I caught her in my arms, her blond curls caressing my cheek as I whispered in my ear, "Are you ready to get stud fucked, Bambi?" I felt my cock hard between her cheeks, and I was even able to ignore the fact that it was straining against silk to do so. My breath was hot and ragged, a predator's grin cut across my face. I had never felt this dominant, this powerful...and then she burst out laughing...

"I'm sorry...tee hee...really I am...I'll hee...I'll stop....I snnrt snicker...I can't EEE HEE HEE HEEEEE!" She doubled over in peels of a laughter and I let her drop to the ground writhing as loud cackling screams tore through her tiny frame. Just when it looked like she might stop, taking deep panting breaths and dropping to a low titter, she looked back up at my perplexed frown and burst out laughing all over again. "hee hee Stud fucked....gah ha HA HAAAA HAAAAAA!"

"What's so funny?!" I yelled, trying to sound intimidating but coming across more petulant and hurt. Probably because I was. I thought I was a zipper away from proving my manhood, that I'd dominate this training wheels sissy enough times to work up the game to take on Isabella. And instead, the biggest sissy in the house was laughing uncontrollably at my attempt to sound butch. I wanted to cry, and when I realized how unmanly wanting to cry was, I wanted to sob... 

She finally managed to compose herself, pulling herself off the ground and on to her knees, wiping a tear away as she sighed, "Oh my...thanks, Byron, I needed that. I know, I know, I shouldn't laugh. And look I got my dress all dirty...oh poo! But you have to admit, the idea of you stud fucking anyone is pretty funny. I mean, considering you let a sissy stud fuck you down in the basement. And right after Master Darren told you if he caught you again he'd add you to the Harem. I'm sorry, I know it's none of my business, but hee hee the basement has really good acoustics...Hee hee oh golly, I'm about to go off again...but...hee hee you couldn't even wait to haa haa you got to your giggle own room. Hee heee heeeee I'm so sorry but HAAA HAAAAAAA!"

All the blood left my body, and I thought for a moment I might actually faint. The ground tilted and I had to stumble in place to keep my footing. She knew...they all did...every sissy in the Harem thought of me as one of them...I'd never be able to start over...I would always be a sissy to them. And if I couldn't change a sissy's mind, how would I ever change my step-father's? On the other hand, if I could make her think of me as a stud, then maybe I could make everyone see me in a new light. I felt cold and hateful and just plain ugly inside. I knew that it was all directed inward, but I decided to use every sickening ounce of it, my words dripping with venom when I said, "I'll make this simple. I am a Master. You are a sissy. Either suck my cock right now, or I'll take you down to the play room and we'll see how good the acoustics are when you scream so loud that you go deaf." 

I looked down and saw that hazy glaze of lust start to fill her eyes. I could barely believe it, but my step-father had been right. If you show strength, sissies will instinctively submit to you...and as Bambi feverishly fumbled with my zipper, I felt stronger than I ever had. My cock throbbing, aching to be sucked, ready to plow into her throat and paint her face with my seed. It felt like it was going to rip through its pantied prison...and that's when I realized I was fucked...

"HEEEEE EEEEE HEEEEEE Cute undies! Ha HA HAAAAAAAA HA AHHHHHH!" She fell back onto the ground laughing like mad. I couldn't listen to it for one more minute. I stormed off and ran up to my room, not even having the courage to drag her down to her cage as punishment. How could I torture someone who couldn't even keep a straight face if I spanked her? I buried my head under the covers until I felt the urge to sob pass. I couldn't imagine facing Bambi again that day, much less Isabella, but it was only mid afternoon. So I did what any manly man would do. I went over to my dresser, found my flask in the underwear drawer, and drank myself unconscious. As my brain swam into the whirlpool of black out drunkenness, I told myself tomorrow would be a better day...

Tuesday

I woke up with a hang over and a sissy's cock brushing my lips. I brushed it away, not wanting to puke on her dick. "Lemme up..." I mumbled and stumbled toward the bathroom, hoping a shower would clean out the cobwebs in my head. I almost fell face first to the ground, so I didn't object when Isabella propped me up and helped me get to the shower. I slumped against the tile wall and slid down to the ground, more dead than alive...but when Isabella pulled the shower nozzle down toward me and started to rain warm water down on me, my body came to life bit by aching bit.

I was too groggy to protest as she soaped me up and scrubbed my soft skin, and besides, there's nothing wrong with a sissy washing her master. I even allowed myself to hope that she was coming around to my way of thinking, showing me the respect I deserved. That is until she stuck two soapy fingers up my ass and cooed into my ear "mmm This spot's especially dirty...it looks like it needs a deep clean." I tried to protest, but before I could even moan a refusal, she thrust her tongue in my mouth and had me sucking passively on it as she pinned my tongue down to the bottom of my mouth, claiming dominance over both of my holes.

I would have stopped her if I wasn't so hung over, half drunk really...or at least I hope I would have. But as two fingers became four, and her kiss swallowed every wet moan down her eager little throat, all I could manage the strength to do was beg her to fuck me. She helped me to my feet, holding me in her arms so I wouldn't fall back down. The warm water cascaded down our smooth skin, making us slide against one another like seals fucking..."Grab the shower rail, sweety. I'm going to show you how sissies cure their hang overs." I grabbed the rail for dear life, my body pressed against the frosted glass, my hips held tight in her hand as she aimed her cock head at my winking little rosebud...

I felt her slide into me slowly, I felt slippery inside and out, soft and smooth and warm, and I was too fucked up to worry why that felt so good at the moment. "Thank yoOOoOooOoooh!" A low, lustful moan fogged up the glass in front of me. I wasn't exactly sure what I was thanking her for. Was it getting me squeaky clean and washing off the filth of my drunken night sweats? Was it for aiming her cock right at my sweet spot every time she sloooooowly filled my asshole with her cock, sending a hot throbbing pulse pumping in my veins, burning out all the poison and replacing it with undiluted sissytonin? Or was it just for the immense kindness she showed in not teasing me while she fucked me? Instead she draped her body against mine, her breasts crushed against my back, her mouth nibbling on my neck and shoulders, her legs sliding slickly against mine, stirring them to life. She wasn't fucking me like I was her bitch, she was fucking me like I was her lover. In retrospect, maybe that was even crueler than when she taunted and teased me...




Young Master Ch. 03



All I know for sure is that her hangover cure works miracles. I went from a three quarters dead shambling wreck to feeling my heart pounding as she pounded my ass, my lungs opening up to force my mouth into a lewd moaning oh face, my muscles taut and strong as I bucked back against her cock, no longer satisfied with slow, gentle love. I needed hard, fast lust and I needed it five minutes ago. Thankfully, she took the hint, pushing me against the glass, pinning me helplessly as she began deep dicking me. Each thrust a retreat as she moved in a wet blur, the heat building inside me, the pressure cooker of my pounded prostate crying out for release, my cock spewing out every impurity left in me along the shower wall as she stoked the fires of my orgasm, burning me alive so I could rise from the ashes, my birdlike wail echoing in the shower as I fell back into her arms. She exploded inside me, pushing out another ribbon of my cum to make room, leaving me thrashing on her cock, her loving embrace the only thing that kept me from crashing to the floor. She eased me down and stroked my hair, kissing the tears off my cheeks even as I tried to tell myself it was just the shower. 

Finally she spoke, maybe to cover the shameful sound of my hiccup like sobs. "It's okay, Master. This time didn't count. You were drunk and I took advantage of you. Why don't you put me in my cage today as punishment and tonight you can show me how a man treats his sissy." I couldn't believe she was saying this, I thought it had to be another trick, but I chose to believe the kindness in her eyes. I was about to tell her I didn't want her to be caged, but there was a kind of quiet pleading in there that told me I'd better just follow her lead.

I simply nodded and stood up, feeling the strength returned to my limbs and feeling strangely virile after my 'hangover cure'. Neither of us spoke as sucked her cum out of my ass, causing me to whimper ever so slightly. and cleaned my stains off the shower wall. After that she dried me with a towel and helped me dress in a pair of black slacks, a black vest over charcoal shirt, and a blood red tie. I cut an almost impressive figure in the mirror when it was all said and done, and I was beginning to push the morning's events out of my mind, like a half forgotten dream. Today was going to be my day, I just knew it...

I decided to explore my home freely for the first time since my new step-family moved in. It gave me a sense of pride to walk through the stately halls, knowing it was all mine once, and if I had my way, would be again, if only a sizable share of it. I passed Darius in the halls and he seemed to notice my new found confidence, giving me a non-committal nod as he passed by me. It wasn't much, but considering I usually didn't inch by him without him snickering at my obvious discomfort, it was huge. For once, I really didn't feel afraid of him. As far as the household was concerned, we were equals now, and I allowed myself to hope that I was on my way to proving my worth.

And just when I thought the day couldn't get any better, smarmy little Dale came pouting past me, muttering "pussy" under his breath. I'd waited a long time for this moment, and I wasn't going to let it pass after he had given me the perfect opening. I grabbed him by his collar and spun him around, landing a slap on his indignant face before he could even protest...

"What did you just call me, boy?" my voice almost cracked under the weight of my contempt for him, but it managed to hold. He just stood their, shocked and sputtering, his boyish face twisted into a tight knot of rage, his fists clenched into balls of impotent white knuckled fury. Sure he could hit me, but he's be breaking his Daddy's precious rules. And he wouldn't dare do that. And with the way I was feeling, I didn't think I'd need his father to protect me. I felt like I could swat him like the gnat he was.

"I...you...you hit me! You just wait. You just wait! I'll show you. Just because you're older, you think you can boss me around? You think you deserve your very own sissy while I wait for another two years? TWO FUCKING YEARS!" by the time he finished his tirade he was almost snarling. But despite all of his rage, he looked about as intimidating as a pissed off poodle. I just smiled calmly, infuriating him even more. I saw his shoulder buck, saw him consider throwing a punch...but he just looked in my eyes, a look of surprise registering in his, and he turned and walked away. 

I spent the rest of the day a living breathing strutting hard on, just waiting for my chance to show Isabella what a man I was. I envisioned every position, every act. And I was sure that I'd have the stamina to last all night. By the time night rolled around, I had already fucked her in my head so many times that I almost expected her to be limping when I saw her. She was wearing a tight leather miniskirt that might as well have been a belt for how high it was cut as well as matching tube top so small it left the succulent swell of the bottom of her breasts hanging out. I could tell she was happy to see me from the outline of her cock ruining the line of her skirt and her hard nipples tenting from her top. She smiled kindly at me, the gentle look from earlier in the morning was still in her eyes, without a hint of mischief or defiance in them. Her voice still surprisingly kind as she said, "I've missed you so much today, Master. Thank you for showing me my place and punishing me." 

I didn't understand it, but I didn't want to ruin the moment. I just nodded and pointed to a spot on the floor right in front of me. I don't know what she saw in my expression, but I saw the beginnings of her wild abandoned lust forming like clouds in her eyes. She knelt on the ground in front of me. "You may use your hands to free my cock, Isabella. But after that, you will get me off with just your mouth." 

Without a word of protest, she unzipped my pants, and pulled my cock out of my plain white boxers. I looked down at her and felt ten feet tall, the look of complete submission in her eyes making me feel completely dominant. My entire body felt like it was coursing with masculine energy, my veins pumping extra strength testosterone to every flexing muscle in my body. All the way down to one special muscle, which throbbed with the sweet painful pleasure of a day's worth of pent up cum. I took a deep breath...despite how desperately I wanted to cum, I NEEDED to prove to Isabella that I was a powerful man, with discipline and self control. I steeled myself as she took my cock in hand...

"Whimper" my muscles seized up as her soft hands sent my lustful need careening out of control, every last drop of extra strength testosterone flooding down to my cock and spewing out in a gushing geyser across Isabella's face. It felt like one of those pees you get when drunk that you begin to worry will last forever, only with cum shooting out of my cock making my cock feel like it would burst into a million chunks of blissful bits at any moment. When I finally felt the last shuddery spurts drip from my cock, I slumped to the ground in rapturous relief. My relief was short lived...

I was on my knees looking up at Isabella's smirking face, the cruel mischievousness had returned in earnest, and I was having trouble remembering what her face looked like with out it..."Aww, poor Master, did you save all that cum for me? That was so generous of you. I think I'll let you lick it of my face and titties before you suck my cock." She held my face in her hands and pulled it closer to hers, I could smell my cum on her, pulling me closer like one of those cartoon pies, I wanted to kiss her so bad. She couldn't smirk and kiss me at the same time after all...

I swallowed her lower lips, sucking on it until she moaned, then I teased her tongue out of her mouth by flicking it flirtatiously with mine. I don't know what I expected to happen, but I didn't fight it when she bullied my tongue with hers, pinning it down and tongue fucking me before biting my lips until I cooed...I don't know why I began licking her face clean and dutifully offering my tongue to her to suck my seed off, sharing my nutty nectar. Maybe I was just getting addicted to the taste, although mine wasn't as robust as hers, it had a certain salty appeal. Maybe I just wanted to figure out why the taste was so exotic and yet so hauntingly familiar, was it cucumber and coriander? Or maybe I really had shot out all of my pent up testosterone for the day, and I had nothing left to fight her off with...

I do know that sucking my cum off her smooth supple breasts and firm swollen nipples was the most sexually confusing thing I'd ever done. I didn't know where it fell in between sissy and stud, but I knew I was finding my second favorite thing to suck on ever and I prayed I'd find one more drop so I would have an excuse to keep kissing every inch of her perfect breasts...but nothing good lasts, I knew that better than anyone after my one pump performance, so I didn't protest when she stood up and touched my head lightly, letting me know it was time to suck her cock.

In a way, I didn't consider it gay to suck her cock anymore. I mean, she didn't look like a guy. And she made the most spine meltingly feminine moans when I did it, and I know from watching my step-father fuck her throat that men didn't make that sound when they got sucked off. So I told myself it was like eating pussy, or more accurately, like sucking on her clit. Her fat, veiny, tonsil pounding clit...

I kissed her cock head, slurping up a dollop of sweet cream, before licking from the head to the base, I wanted to get it covered in spit, hoping to take it all the way this time. But I didn't have enough spit, so I swallowed my pride and looked up at her pleadingly, begging, "Please spit in my mouth, Mistress." 

"God, you're pathetic...but that's why I love you so much..." she shoved three fingers down her throat and worked them in and out viciously until a viscous stream of spittle drooled down my eager throat. I grunted piggishly as I spat some back on her cock and worked it up and down with my hand, loving the little moans she made when I added a corkscrew flourish as I got to the head. I was ready as I would ever be, and mercifully so lost in the haze that the sheer wrongness of the act only made it hotter...

I gave it one last kiss for luck before taking her into my mouth, pushing my head further and further, feeling a gag rising just as she reached my tonsils and pushing it back with her fat cock. I felt my throat open around her cock, felt it throb inside me. There was something about her being inside me like this, feeling her pulse block my airways, as if I were about to give my life for her pleasure. I don't know if it was oxygen deprivation or the sheer depravity of the act, but I swooned around her cock. When she pulled me off her cock by the roots of my hair, I felt the cool air rush into to put out the fire in my lungs. I didn't waste anytime, and dove right back onto her cock. I felt it getting closer and closer, until I could see her belly just an inch away. It was so close, like the soft plains of paradise, leading up to the heavenly mountains...but it was like there was this soft wall that wouldn't budge, no matter how hard I pushed...

I pulled off as the constellation of colors before my eyes told me in ancient hieroglyphics that I was about to pass out, and then I jumped right back into the fire, my throat scorching with the raw friction of her cock sawing in and out of me, faster and faster in a frantic attempt to reach the end. But as I felt her cock expand in my throat, I knew she was about to finish the race before I could go the distance. I didn't fight it as she pumped a gallon of her seed right down my stomach then coated my throat with the best sore throat remedy I'd ever tried and finally pulsing in my greedy mouth. I surprised her with my gluttony as I grabbed the base of her cock and jerked it off into my mouth, guzzling as quickly as I could to keep every drop for myself. Even after I felt the last precious pearl squeeze out, I sucked on her cock and jerked her off until she pushed me off with her foot. 

"Damn...you never can quit while you're ahead, can you? You give me at least a B minus blow job and then ruin it all by not only getting greedy and keeping all of my tasty cum for yourself, but by yanking on my cock like you wanted to take it with you. If I didn't think you'd get off on it, I'd spank your right now. Instead, I'll really punish you. I'm going back to the basement. And don't even think of getting any of this until tomorrow night, when for your sake, I hope you do better than this." She left me sniffling on the floor, a last watery drop of cum leaking from the tip of my cowering cock wondering which made me feel more ashamed, that I couldn't please her as a man or as a sissy...I didn't find the answer in a night of fitful sleep and frighteningly real wet nightmares.

Wednesday

I woke up and true to her word, Isabella was not there to take advantage of me. I was disappointed that I wouldn't be able to use grogginess or drunkenness to justify getting a load of her cum in one of my hungry holes. I felt my cock twitching ready and eager to play and my asshole itching deep inside where only a cock could scratch it. I thought for a moment about trying to find my gee that feels good spot with my fingers and having a nice morning wank to pick up my spirits, but then I realized I'd only feel worse afterward. I had to do something to break out of this pattern of fruitless attempts to be the ultimate man and surrendering to the sissy splendor of forbidden fruits. 

If trying to be a man like my step-father made me feel weak and giving into being a sissy because it seemed easier made me feel guilty, maybe I wasn't either, and maybe I didn't have to be. I made a different vow that day. I vowed not to try to be an atavistic anachronism of male machismo or to escape into some ridiculous fantasy of deviant delights. I decided to be myself, and hoped that was enough to skate by...

I realized as the day passed tortuously slow, that the real me was pretty dull. Something about being constantly pandered to makes it hard for anything to hold your interest. I'd spent the last year waiting in bored frustration to have full reign of the house back and all my perks and privileges, but now that I had them, I realized what a waste of time it had been. I didn't want them. I didn't know what I wanted, but it wasn't something I could just reach out and grab. The only problem was, I didn't know how to get anything else, I didn't know how to do anything else. So I just watched the hours slither past as I got progressively bored and horny. I was seriously considering drinking myself into a stupor when I saw Sakura walking towards me.

I tensed up as she got closer and closer, fearing a repeat of my humiliating encounter with Bambi. But There was something about her walk, tense and fearful, wringing her hands as she mouthed whatever speech she was working up the courage to give...she seemed so vulnerable, so pent up...I couldn't help but relate. She finally stood before me, still not daring to look me in the eyes, her bangs hiding her delicious almond eyes, a beautiful blush painted in light strokes across her pale ivory skin. I regretted not choosing her as my kept sissy, but regrets didn't change what was. I focused on what was in front of me instead of what was behind me and asked Sakura, "Is there something I can help you with?"

She still didn't look up as stiffly she answered "Yes, most honorable Mastersan, this lowly sissy begs a thousand pardons, but would you show her the ultimate benevolence of showing her the smallest of kindnesses?" I had forgotten how deferential and self effacing Sakura was. I couldn't tell if it was for my benefit, or if she really did consider herself that far below me. Considering she had to know about my little tryst with Isabella in the basement, that was saying a lot...I thought the least I could do was hear her out...

"Okay, tell me what you want, only please, hold the honorifics." I waited for her to gather the courage to speak again, and felt a little guilty for sounding so dismissive. I knew I wouldn't want to be in her place...or at least I hoped I didn't want to be in her place...

"Yes, Mastersan, this lowly sissy will try to make the greatest of haste. My need is vast as the ocean and twice as deep. But my tongue can not express my need, only by sharing my great dishonor may I hope to find relief. Please, honorable Mastersan, may I show you my need?" She threw her words to the ground as if they were diseased animals, it seemed physically painful for her to form them and force them out of her delicate mouth. Her body was shaking like a leaf from the strain, and I wondered how I would cope with all I was going through with the added burden of using a foreign language as well. I couldn't watch another minute. I stood up and closed the gap between us, taking her head in my hands and lifting it so that she could see the compassion in my eyes...

"Sakura, please, you don't have to act like this with me. I'm not like the other Masters. I don't want you to feel ashamed. I just want to help you. So please, show me your need and I'll see what I can do." The furrows on her brow smoothed out and the corners of her lips turned up ever so slightly. It was the happiest I ever remembered seeing her, which made me feel even sorrier for her. But that was nothing compared to the pity I felt for her when she lifted her tartan skirt and revealed a gilded cage around her cock. "I...I'm sorry, Sakura. I can't imagine how painful that must be...but, what do you want me to do about it?" 

Now she was the one taking my head in her hands, pulling me so close that a breeze couldn't fit through the space between our lips, "Please do not make light of this poor sissy's burden. On the very same keyring that you were given to lock your sissy's collar, there is a key for each of the common house sissy's chastity cages. The honorable Master Darriussan put me in this cage a week ago on a whim, and since no one has used me since, I have been denied the tender mercy of release. If only Mastersan would release this undeserving sissy, she would offer you her humble skills and common body." 

I fumbled for my keyring, cursing my lack of curiosity about what the other keys were for, desperate to release Sakura, as much for her sake as mine. I fished it out of my pocket, and finally found the one I was looking for, a tiny key with a cherry blossom on it...I got down on my knees and carefully aimed the key at the hole, holding my breath as I slid it in and turned it, fearing the entire time it wouldn't work. When I heard a click of release, I barely suppressed a whoop, and I removed the cage from her cock, already stirring to grow a good three inches. I stood up hurriedly, afraid she might be under the mistaken impression I freed her to get a taste of her sissy clit. 

She was openly stroking her clit to full hardness, her precum making it slick and shiny, she made tiny stifled yelps as if she were in pain, I supposed from the dishonor she felt in me seeing her like this. This was my idea of what a sissy should be, eternally chaste, pristine and perfect, and a true slut. Never losing her innocence so that it could always be plundered and defiled. But at the same time, I started to sympathize with the sissy's point of view. I wondered how she could endure it...I was tormented by my few indiscretions, but that's all her life was now. She was living my ultimate nightmare, so how could I take advantage of her need? It was strange to think that only a few days ago that I all I wanted in the world was a sissy to use as my very own toy. Now that I had one, all I wanted was to hold her close and tell her everything would be alright...but it wouldn't. So I did what little I could, I told her, "You don't have to do anything for me, Sakura. I just want you to get some relief. I'll hold onto your cage, you just do whatever you need to do to cum."




Young Master Ch. 03



She looked at me as if I had just spit in her face, I couldn't understand it, there I was, trying to do her a favor and she looked horrified and betrayed. I didn't know what to say, what to do. She couldn't say anything, it was up to me to figure out what I did wrong....and then it hit me. I felt like someone took my guts in their hand and twisted them in a knot...she couldn't cum. The cage was off, but she didn't dare cum on her own, and after all this time of putting the Masters' pleasure first, she might not even be able to get off without a Master there to use her. I was so hard, but I hadn't been able to get off on my own either. Suddenly I felt closer to her than ever before, and I wrapped my arms around her, pulling her head on my shoulder, whispering "I want you to take my cock out, and rub it against yours until we both cum."

She yelped again as she unzipped my pants and pulled out my cock with the skill and speed of a ninja. My cock was already dribbling precum as well, so there was no resistance as she took both in her hands and began sliding her hips up and down. Soon our throbbing pricks were sliding against one another like snakes in love, feeling like a million needles coated in honeyed heroin were kissing my tender flesh. I felt something powerful welling up inside me, something even more urgent than the surging rush of cum boiling in my balls ready to blow any moment. I pulled her head up, saw the look of pained ecstasy in her eyes, and crushed my lips against hers in desperate attempt to burn away the shame...

She whimpered into my open mouth and our tongues danced, sliding against one another faster and faster keeping time to our slick sexes, our whimpers, moans, and yelps the music we waltzed to. It was a painful moment, haunting in its beauty and its paradox of perfect pleasure and pointless pain. If only the moment could last forever, our perfect union, a connection based on kindness and a mutually selfless expression of sensuality. It would be Heaven...and Hell...

Because even as we ascended closer and closer to Heaven as our bodies were grinding against one another, the flames of Hell possessively refused to let us go, the pain of unrequited lust creating an emptiness deeper than any love we could hope to fill it with. What I wanted was to stay like this forever, what I NEEDED was to cum right away, before I suffered permanent brain damage. Heaven and Hell, a pleasure chased that can only be attained when you let it lose, a connection more profound in the separation than in the union...it was all so fucking zen. But I didn't have time for philosophy, and neither did Sakura, apparently. She cried out, "Please, Mastersan, please humor this sissy's inept efforts and cum. I can not dishonor myself by cumming first, but oh fuck me sideways, I need to cum so fucking bad!" 

Hearing her voice tear apart as a raw savage beast ripped itself free was all it took to send me careening over the edge, my cock kissed by a million angels, their burning lips sending my spirit soaring, all across Sakura's blouse. A millisecond later, Sakura sobbed as her body shook violently, a thick load shaking free and landing on my polo. We both just held each other until the tremors stopped, my skin tingling as I came back down gently to the earth. I wanted to enjoy this moment free from shame or doubt for as long as I could, but Sakura landed a little harder than I did. She cried out, "Please, most generous and magnanimous Mastersan, please forgive this lowly sissy for desecrating you with her vile waste. I will commit seppuku at once!" 

I didn't wait to find out if she meant a metaphorical disembowelment, reassuring her, "Don't worry, Sakura, I have plenty of shirts. I'm just glad we were able to help each other. If you like, I can hold onto this cage for you so you can breathe a little easier." She seemed immensely grateful for my forgiveness, which made me feel a little uncomfortable, as it reminded me of the yawning chasm between our roles. But when I offered to keep her cage, her expression turned to one of horror, as if I'd casually suggested she sleep in a snake pit.

"Please, Mastersan, this pathetic sissy is not as brave and powerful as you. She does not dare invite the wrath of Darriussan upon her if he finds her without a cage. I beg you with all my soul, please lock me back up." and as I silently locked her cock back in its painfully confining chastity cage, I was reminded of the even greater gap between men like Darius and men like me. But for the first time, I couldn't say if he was stronger than me, or just crueler. I suppose it didn't matter to Sakura, that knowledge wouldn't protect her from his sadistic whimsy. As I gave her leave and watched her walk away with those tiny, shameful steps of hers, I hoped I would find a way to truly help her someday...but first I would have to find a way to help myself.

I spent the rest of the afternoon and most of the evening lost in thought. I kept asking myself how could I help myself, and was there anyone who could help me? I wanted to believe Isabella could, but I didn't know which side of her to trust. Was she the malicious minx that loved nothing more than leading me on and letting me down, or was she the kind and gentle soul that took care of me when I was in my cups? Maybe she was both, maybe she played her vicious little games to help herself, a defense mechanism to keep her from giving in completely to the siren call of surrender. If that was the case, maybe we could help each other. I was resolved to try, and I now thanks to Sakura, I knew just how to connect to her...

When she came into my room she was wearing a too tight school girl outfit that I immediately recognized as Sakura's. While on Sakura it was cut to give the impression of a demure innocence, on Isabella her extra height made the skirt shockingly short, and her more prominent attributes made it impossible for her to button the top of her shirt, leaving her cleavage all but spilling out. She seemed to enjoy the effect it was having on me, "Sakura told me how you played sissy chicken with her today, so I thought maybe you wanted to play the same game with me. I can't wait to see who lasts the longest."

I didn't know what she meant by a game. I was just helping Sakura out, it wasn't a competition. And I sure wouldn't have played it if I knew they called it 'sissy chicken'. I still wanted to do the same with Isabella, it wasn't to prove anything about who was stronger, I just wanted to be closer to her. I decided to take a gamble in hopes that if I played the game her way, maybe we would connect the way Sakura and I did, and then she wouldn't care who 'won'. "Alright, I'll play. But, isn't there anywhere safer to play than here? We can't keep doing this in my room, the door won't even lock."

I regretted my prudence when she told me that the safest place to play sissy games was in the basement. No one ever went down there at night and we'd have the place all to ourselves, not counting the eager sissy audience. So with all the courage I could muster, and a damn sight more I was just faking, I followed her into the basement. I was surprised to see there weren't any sissies in the cages and more than a little relieved. If they were all gone too, then maybe this wouldn't end in embarrassment. But she just smiled and took me by the hand further into the basement, further than my step-father had taken me on his threatening tour. I wondered just how big the basement was and started to think it was more like an underground compound when the winding tunnels finally led us to a room filled with whispered giggles. 

We stepped into a room filled with cots, enough to hold a sissy army. I wondered just how many sissies Darren planned to own. All the other sissies were there...Sakura wearing only her cage. blushing and looking away as we made eye contact...Bambi practicing pouting in front of a mirror, turning with a giggle as she saw me in the reflection....Lola a look of haughty passion on her face as she sat on Cunt's back, slapping her ass to get her to carry her around the room...the look of serenity on Cunt's slack face telling me it wasn't entirely forced...they all turned to me in stunned surprise, and Isabella finally broke the silence. "Well Master, this is where we sleep. They would probably just keep us in the cages overnight, but they don't want our skin getting those nasty grid marks now do they?"

"I...I guh guh guess not..." my stuttering sputter was returning with a vengeance. I didn't like the hungry look the sissies were giving me and all of the sudden I wondered what the stakes of this not so little game where. "Uhm what eh eh exactly is the gah gah game, Isabella?"

She took me by the hand, and led me to the center of the room, I felt surrounded by sissies, crowded by their eyes, I just stared dumbly as she started unbuttoning her shirt, when she saw the clueless expression on my face, she laughed and said, "What are you waiting for, Master? We both have to be naked to play sissy chicken."

I started pulling off my clothes as fast as I could, I had no idea what sissy chicken was, and yet there I was, standing before her absolutely naked, my cock already aching, dripping precum on the floor at the sight of her so soft and so hard at the same time, I hoped she wouldn't notice, but of course she did, "Oh this won't do at all. If you want to win at sissy chicken you'll have to last longer than this. The rules are simple, we both rub our cute little clits together in a race to see who cums first, only who ever finishes first, comes in last. I'd tell you what happens to the sticky little loser, but I don't want you to cum before we can even get started."

I saw the fire burning in her eyes again, threatening to melt me on the spot, I looked around the room, and saw that they were all waiting for it to happen. Licking their lips in anticipation of what was to cum. I don't know why, but I had the craziest notion that I might actually be able to win this time. I had lost every battle of wills I'd ever had with her, but in a way, that gave me an advantage. She wouldn't be expecting a challenge. And I gambled everything on that, hoping not only to win the game, but hopefully her heart. Somehow I just knew that if I could only connect with her as equals, just once, we could put all the games aside.

I stepped closer and she took my cock in her hand, smearing my copious leakage all over her smooth sissy stick, and then began rubbing it against mine. I knew from the moment she put her other hand on my chin and lifted my gaze to hers that I was doomed. The sharp angle of her smirk cut me down to size...the tip of her tongue stuck out of the other side of her mouth, ready to lap me up...her nostrils flared like a savage beast stoking the fires that made her cheeks flush with anticipation, a single bead of sweat running down her smooth skin, making me wish I was tall enough to lick it off...her eyes held me prisoner, the reflection of a simpering sissy trapped inside them. I tried to look away in one last futile effort to hold out just a little longer, but that only made things worse. I saw her cock dwarf mine as it crushed against it, pushing it into my soft stomach, her cock-head poked my belly button with every thrust of her hips, making me feel penetrated and helpless. My puny penis was covered in my slick juices, it gave no resistance as her superior member mashed against it, squeezing more and more out until I was thrust my hips back against her, not to try and make her cum first, but to end this sorry spectacle my legs buckling as every muscle went rubbery in response to my sticky spasm. My tiny prick oblivious to the shame of it ecstatic eruption sending a warm buzz throughout me that lasted just long enough for Isabella to pick up my limp body, her muscles popping from underneath her silken skin, and hover me right over her cock. 

I came to my senses in time to realize my asshole was puckered around the tip of her cock and I was about to get stud fucked by my sissy in front of a live studio audience. "Please, I AIEEEEEEE!" My leakage had made her cock slick, and my tight little hole was no match for the forces of gravity. I cursed Issac Newton as my legs wrapped themselves around her and my face buried itself in the nape of her neck, hiding my shameful blush in her raven locks...

"Tee hee Make him your little fuck dolly, Isabella!' Bambi bubbled, reaching into her panties and stroking herself feverishly as Isabella pulled me off of her cock, every inch a revelation. Every time I got fucked I discovered something new about my treacherous body. How the slightest angle could be the difference between Heaven or Hell, and take me that much closer to the place where they were one and the same. 

"Si, pound this puta's culo until she cries for her papi" Lola had gotten into the show with a frightening zeal, taking poor Cunt by her ears and rubbing her tanned cock across her face until she began obediently taking it all the way down her throat. The look in Cunt's eyes terrified me more than anything, it was one of recognition...seeing the bitch in me surrender to the physics of a phallus pushing into me all the way down to the hilt, pounding my prostate and sending a chain reaction to every raw nerve in my ass. I clenched down on it, felt my asshole milk her hard hot flesh for more sensation. I needed to feel more, to drown my mind in dick doped drool, to escape this nightmarish reality for just as long as she could keep fucking me...

I looked to Sakura for support, hoping to find a single pair of kind eyes in the crowd. Instead I saw the same hazy hunger. I wasn't a Master to her anymore, wasn't even an equal, I was just a sissy chicken and she had no sympathy for anyone weaker than herself. "Yes! Fuck her harder Isabellasan! Send this sissy to the Hell of Never ending Cum!" I thought I might already be there, I couldn't tell if I was cumming anymore, her cock had truly transformed my asshole into a wet cunt, and my body into a vessel for unholy orgasms. Possessing me like foul mouthed demons, twisting my lips into a lewd moan, screaming "fuck me Mommy! Fuck me MOMMMEEEEE! Make you your little cum dump whore! EEEEEEEEEEE!" 

Time slowed as she swelled inside me, her cum shooting up inside me sending me careening off her cock and through the basement ceiling, blasting through the floors and out the roof, piercing the sky and cutting through the clouds, burning up as I broke through the atmosphere like some reverse comet, streaking past the speed of light past the edge of the universe, reaching that perfect place where nothing exists, not even me. Everything was empty...it was Nirvana...

I crashed back down to Earth just as suddenly, Isabella dropped me to the floor and laughed as the sissies scrambled to suck her cum out of my abused asshole, to lick her clean in tribute to her triumphant victory. I curled into a little ball, trying to block out everything trying to get back to that wonderful nothingness..."Hee hee Look! He sucks his thumb! I thought only I did that!" Bambi tittered. Luckily I must have hit my head when I landed, because I blacked out, finally escaping.

I came to in spurts, feeling Isabella pick me up and check to see if I was okay..."Jussssst a liiiiiittle buuuuuump. Whaaaaaat a sssssssissssssyyyy" Carrying me out of the basement....sneaking me back up to my room...tucking me in...and giving me a little kiss on the bump when she was positive I was already passed out...It had been a good day after all...

Thursday

I woke up sore, and sorely vexed, with Isabella's morning wood sliding up and down between my ass cheeks as she cooed in my ear "Gooooood mooooorning, Master. Were you dreaming of me? Dreaming of my fat sissy sausage sliding up your cute little boi pussy? Well guess what, you're dreams are about to cum true..." 

I leaped out of bed, angry at how she used me last night and afraid I was about to let her do the same this morning. She looked amused at my sudden outburst and I saw that she had changed outfits for me again, this time wearing a much too small Girl Scouts Uniform, only bright pink with 'Sissy Scouts' emblazoned on the shoulder. I saw various badges for anal and crafts, ass to mouth respiration, cumminity service. In one hand she held up her lacy pink thong, and the other a new badge, "Aww, don't you want to earn your deep throating badge today?"

She wasn't even trying to trick me anymore. She thought I was so broken that I'd willingly surrender without even the illusion of a fight, and as I licked my lips, I saw where I might have given her that impression. But I drew a line, then and there. Whatever I was...man, sissy, or something else entirely, I deserved better than her. And I let her know it. "No, Isabella, I don't want anything from you. Now or ever. I don't want you to come near me. So why don't you..." I was about to tell her to lock herself in one of those horrible cages, but just the image of it twisted my guts into a knot. No matter how much she hurt me, I still couldn't bring myself to hurt her back. "why don't you clean up around the house?" 

I turned my back on her sullen pout before I couldn't stop myself from kissing it off her face...and with that, I was free...or so I'd hoped. But with every step I took away from her, the closer she was to my thoughts. All I wanted was for her to look at me with those kind eyes all the time, that soft smile melting into mine in a never ending kiss. But I knew that would never happen. If I did see her softer side again, it would only be to play another sick little game. I was tired of being her Charlie Brown, always giving her another chance to pull the football away at the last moment...only instead of landing on the hard ground, I fell onto her hard cock.

I spent a good ten minutes trying to shake THAT image out of my head, and decided to do something to keep it out. I headed down to the gym for the first time in my life, determined to make something of myself. I changed into a tank top, workout shorts and sneakers, and I was fired up, I was raring to go, I was chewing up matches and spitting fire...I was completely lost...where was I supposed to start?

I decided to try something simple, that even I could figure out, and grabbed some free weights to do curls. I looked around for the lightest one, but all I could find was fifty pounds. So taking my good right hand and gripping it as tightly as I could, I lifted with all my might. Pain steadily stabbed it's way up my arm, but I tried to push through it, knowing that with punishment comes reward, and managed to lift it several inches off the ground before feeling it pull me down to the ground. It was strange, there was only room for one hand, but how was anyone supposed to lift fifty pounds with one hand?

I looked around for something more humanly possible, and settled on a treadmill. I fiddled with the controls until I found the slowest pace and easiest virtual track and began running in place as the belt moved below my feet. I felt the impact travel all the way up to my buttocks and I set forth to see how far I could push myself. But after a ten or so minutes, the routine was still somehow going...my legs felt like knives were dragging up and down them and my lungs felt like I was breathing battery acid. And then the machine sped up...set to a blistering 'jog' and hurling me to the ground, landing right on my pride...

It wasn't fair...my step-brothers made exercise look so easy. I briefly considered asking one of them to help train me, but immediately rejected it. I could just imagine what Dirk would say if he saw me failing at the lowest levels of fitness training. "Holy shit. You're even more pathetic than I thought. How can you even call yourself a man?" I looked up at the towering mass of muscles leering down at me and realized with a start that I wasn't just imagining his voice...




Young Master Ch. 03



"YEEP! I uh I mean hi, Dirk. I was just...well I was trying to...I don't know..." and I really didn't know. Suddenly I didn't know anything. Dirk was pulling me up to my feet, his usual shit eating grin plastered on his aggressively handsome face his eyes looking at me with the same casual contempt as always, but there was something new in them today as well, something I didn't want to put a finger on..."Well, I uh buh buh better be going." I spoke into the ground and waited for him to let go of my reed like arms.

"I know what you need..." he said, his hands moving up and down my arms, squeezing them slightly as if to feel for nonexistent muscles. I yelped in pain, but he just pulled my hand and placed it on his twitching pecs, his skin tan and slick from his warm ups, he moved my hand further down the rocky path of his chiseled abs, down towards his tight fitting work out shorts already bulging with him still soft. "You need this body, don't you?"

I could barely speak. What was he saying? I didn't want his body. I was straight...ish...I mean, sure I was in love with sissy cock, but that was attached to a soft angel faced succubus, not some huge muscle bear of a man. But once he said it, I did start to have my doubts. I couldn't deny that a part of me got off on being humiliated and dominated...okay, a frighteningly large part of me. And if a sissy could bully the cum out of me, I could only imagine what Dirk could do. But I didn't want it, not really..."I...do?"

I felt his laugh roll through him like thunder. "Of course you do. And if you do every last thing I tell you to do..." he spun me around sending my head into a tailspin, "and fight every instinct your body gives you telling you to stop..," he pushed me down so my body slumped over, but with his hands on my hips keeping my ass up and out, "then I'll work you hard and long..." he kicked my legs apart until my thighs burned with the strain, my heart was beating a mile a minute. I thought I might end up the first man to overexert himself from a warm up. "Then I'll give you what you need." His groin pressed against my ass...I was terrified. What was he going to do? Why wasn't I telling him to stop, well besides it being pointless? And why wasn't he hard? If he wasn't about to rape me, then what was he talking about?

"So, let's start off with toe touches and then do some jumping jacks. Once we've got you nice and limber we'll move onto some weights. Trust me, Byron, with me as your personal trainer you'll have a body like mine in no time." I like to think I was more relieved than disappointed. Either way, there was no way out of the gym but through Dirk, and that meant touching my toes. Which was easier said than done...

Pain gnawed at muscles I didn't know I had, every joint aching and ready to snap like a twig. But I remembered feeling Isabella's thick rod in my throat, and thinking I couldn't go another centimeter, then pushing past the pain to go another few inches..."Another...few...inches...UNNGH!" I managed to graze the tops of my sneakers with tips of my fingers and rose in a triumphant roar. "YES! I did it!" I turned around to see Dirk staring at me in bemused surprise.

"Well normally, you do at least twenty, but since this is your first day, we'll let you off easy. Now let's see those titties bounce." I was burning up at his condescending tone and the way he talks about me as if I was a women, but I figured it was just Dirk being Dirk, and I did need the help. I began jumping up and down throwing my limbs in all directions and Dirk stood their laughing for a moment before saying, "Stop, stop, stop. You're doing it all wrong. Here, I'll show you." He started into his jumps, his legs and arms pulling out to a perfect star in the air and moving back down straight as he landed. After starting off slowly, he told me to join in.

I was able to get the hang of it quicker than I expected, and it wasn't as rigorous as touching my toes. Soon I had gotten into the same slow, steady rhythm he was in, feeling the soreness start to weigh down my limbs just as he started to speed up. I tried to keep up, but he became a blur of taut muscles and sweat flying, by the time he was finished I was collapsed on the floor wheezing, watching him bounce hypnotically. "Pathetic, but admittedly, a little less pathetic than I expected. Now, get up, sissy, it's time to get pumped."

I blushed when I realized he meant lifting weights. And tried to ignore the confusing signals this model of manhood was sending out. He motioned me to lay back down on a weight bench and moved right behind my head, so that his balls were almost resting on my temple. He pulled out a bar with two tiny weights at the end saying, "Normally, these are for going up gradually from something like 350 to 375 before jumping straight up to 400, but for a little while at least, we'll need to build you up on these." he dropped them into my hands, and they almost crushed my chest, before I managed to keep them hovering just above me.

"Come on...you can do it, feel those titties burn and lift that mother fucker. I'll spot you if you can't do a full rep, but just lift it up once." I wanted to prove I could do that much. I felt like my arms would split open at any second, but I managed to get them up to his waiting arms. And then I did something that surprised even me. I held them in place, and lowered them slowly down to my chest. "There you go. There might be some hope for you yet." I swelled with pride and felt a surge of strength travel through me, lifting the bar in one powerful thrust. 

I wanted to see how far I could take myself, and again lowered the bar, and again raised it. After a while the pain became just another sensation. And I looked up at Dirk to see how I was doing, immediately regretting it when I saw his bulge looming over me. Every time I did a rep, I imagined what his cock might look like. It looked fatter than his dad's, would it be as long? I knew I shouldn't even be curious about it, but it was literally staring me in the face. In the end, I said, "Can't take it any more..." and handed Dirk the weights, hoping he'd think I was talking about the exercises...

He peeled me off the table effortlessly with one arm and said, "Not bad for your first time. Now for the best part of the work out, feeling that adrenaline wash over you as you take a nice hot shower and ease those sore muscles. Come on, follow me." I was a little surprised to see our gym came with it's own showers, but with the size of the place, I suppose I shouldn't have been. I was extremely self conscious about showering in front of Dirk, so I couldn't believe my luck when he said. "Well I think you can handle this part by yourself. I'm going to go start my workout." 

I peeled off my rank sweaty clothes and turned on the hot water, letting it hit my skin with a hiss, burning away the stink of sweat. I turned it down to a warm downpour and began soaping up my aching muscles. It felt so good to feel something soft and slippery after working so hard, and before long I was struggling to stifle a moan as I cupped my plump buttocks and slid them up and down against one another. I imagined what Dirk would say if he saw me like this, "Ha! I always knew you were a sissy." and when I felt his hard cock slip between my ass cheeks and his hand close around my neck, I realized I wasn't imagining it.

"No...I...I..."I tried to protest, but I could barely breathe...I could feel his muscles pressed hard against my back, and I struggled against him, but that only made my ass writhe around his fat cock, hugging it tightly. I stopped before he thought I was doing it on purpose. With his free hand, he reached around and tweaked my nipple forcing a pained moan out even past his grip on my throat. 

"I always knew you wanted my cock, your fear filled eyes were just begging me to pop your cherry, but after seeing the way you've been swaying those hips lately, I'd say someone beat me to it." I started to panic...he knew! He was going to tell my step-father and I was going to end up in the basement! I tried to calm myself, he had no proof, he was just bluffing...or so I hoped.

"Look at you...scared stiff are you?" His hand closed around my cock, as horribly hard as it's ever been and leaking in his grip. "Maybe I'll do you a favor. Maybe I'll force my fat cock up your ass and you can tell yourself it was rape. No one would ever believe you if you told of course. Hell, I could drag you still with your ass still leaking cum to my dad and tell him you begged me for it, and he'd believe me. Shit, by the time I'm done, you will be begging me for it..."

I felt the head of his cock pushing at my entrance, threatening to tear into shreds. I'd never had anything this wide up inside me before, and I didn't know if it would fit...or if it would be worse if it did. I just knew that whether I wanted it or not, I was about to get fucked until I did want it, and then dragged like the spoils of war and laid at my step-father's table, doomed to a life of slavery. So why was I still so hard? Why couldn't I fight past the haze to at least whimper a customary objection? I closed my eyes and waited for the inevitable...and them I heard the low roll of thunderous laughter...

"Sorry, sissy, but you just aren't my type. I like a sissy with a figure, not a flat chested little girl like you." He dropped me to the floor in a sobbing heap, his laughter echoing off the tile walls as he left as suddenly as he came and echoing in my head long after that. After what seemed like an eternity, I pulled myself up off the floor feeling beaten and violated. The fact that he didn't actually stick his cock up my ass was just a formality. I had been well and truly fucked. And the cherry on top of the shame sundae? I was still hard...

I wasted no time going up to my room and drinking myself into a stupor, half hoping I'd get alcohol poisoning and would never have to see Dirk's smug smirk ever again. I knew it would leave me vulnerable to Isabella if she surprised me in the morning again, but that seemed like a minor embarrassment at that point. I pulled the covers over my head and held onto my pillow tight, curling up into a fetal position and feeling the room rock me like I was back in the womb...and then...nothing...

Friday

I woke up screaming, not sure if it was from the nightmare already dissolving in the light of day, or the realization that I wasn't going to wake up from the nightmare my real life had turned into. I felt like hammered shit that had been left in the sun all day, and somehow I knew this would probably be the highlight of my day. But I didn't want to think about what the day might bring, about having to avoid every living soul in the house for fear of humiliation or worse. And I sure didn't want to consider how long I expected to last at this rate. I just wanted to keep my throbbing head down and take it one agonizing step at a time...

Which wasn't made any easier due to the fact I hadn't cum in 24 hours. And with all the 'action' I had been getting lately, that was like dog years, the more I got, the more I missed it when it was gone. I made the first of what I was sure would be many stupid decisions that day and went to look for Isabella. I needed a cure for my hangover and she always carried one with her. I looked high and low for her and finally found her on the first floor, conspicuously dusting the floor in a French Maid's outfit by bending at the hip and showing off her gorgeous garters biting into her ass, her black lace cheeky panties showing off the seductive slope of her ass while leaving enough covered to make me want to see more. I walked up behind her and gave her a slow squeeze...

"ooOoooh. Master! I knew you couldn't stay mad for long." She turned and pulled her mouth into mine, kissing away the dismissive comment on the tip of my tongue and painting it with her own, putting sweet words of surrender in my mouth as we fumbled into an open room. I checked to see if it locked behind me...thankfully it did. Now all we had to do was moan quietly and we'd be home free.

I couldn't stop caressing every inch of her with my eyes. I don't know if absence made the heart grow fonder, but it sure made the cock grow harder. And she had to pick my biggest weakness...maids. My first erotic fumblings both set my lifelong fascination and the lifelong ban on maids, my mother finding me nursing on a buxom young maid at age five, a hundred dollar bill in her blouse and milk dribbling off my lips. I'm sure Freud would say that all of my problems stemmed from my mother refusing to breast feed me as a child, but sometimes paying a maid to let you nurse on her is just paying a maid to let you nurse on her. Whatever the cause, they were my Achilles' heel, only of Achilles was soft all over and just extra soft on his heel. Unfortunately for me, Isabella noticed...

"It's about time! I'm been wearing the cutest outfits all week waiting for you to find one you just had to try on. And I finally found it. Do you want to be my sexy little maid, Byron? Or should I call you...Belle?" She began slowly stripping off her clothes and flinging them at my feet. I tried to tell myself I just liked seeing her in them, but as each piece fell to the ground and my eyes followed it instead of ogling her naked flesh...I knew there was no point kidding myself...

"Yes, Mistress. Please...call me Belle." I don't know if it was another case of her planting a virulent seed or if I was already too fertile, but lost in the moment, I didn't care. I was ready for one more try at kicking that football, as I slipped on her panties and felt the lace rub my cock maddeningly...her stockings kissing my legs continually with softness...the garters she helped me put on tugging at them in constant reminder...a corset clinched tight around me in a lover's embrace giving me a slightly womanly curve, making me light headed and giddy from lack of breath...the short ruffled skirt and low cut top, made for only just covering my girlish ass, that is until I twirled to turn around or bent over to pick up things...the little bonnet, so innocent and erotic at the same time. I could barely sit still, squirming in manic desire as she put on my make up, making me the perfect vision of domestic slavery...

By the time she said, "Belle, my cock is dirty. I need you to clean it," it was already in my mouth...and before long, I heard her say, "That's a good little, sissy. I told you that you could take the whole thing." I feel a sense of ashamed accomplishment as I feel her smooth balls rest on her chin and smell her intoxicating mix of pomegranate and a hint of musk as my nose crushes into her smooth taut torso. This was the last time. It had to be. We couldn't keep sneaking around waiting for a chance for a furtive fuck or speedy suck. And if I got caught...no, I didn't even want to imagine what it would be like to be stuck in that sissy hell down in the basement. At least not until after I came inside her pretty lace panties...and then never again...

It didn't take long for either of us, apparently I wasn't the only one that didn't get to cum the night before...I felt her throbbing inside me, and heard a perverse voice shout, "No...on my face...please, cum on my face!" That I realized with a whimper belonged to me. Before I could change my mind, and I'm not sure I wanted to, she had pulled out and was ready to blow...time slowed to a crawl as I saw the veins in her cock pulse and then everything went white. 

My eyes stung as a hot load of cum coated my face, but I obediently waited for her to lick them clean. Enjoying the frustration and wanting this moment to last as long as possible. When I finally felt her soft tongue petting my face, I just melted into her arms. Completely submissive and accepting what ever delicacies she decided to share with me by spitting them slowly into my mouth. Was that asparagus roasted in duck fat that I detected hints of? I swore I'd pin down that taste some day, I just needed more samples. 

My hangover cured, and the buzz still keeping me floating above the pit of despair and regret, I wanted to make this last as long as possible. After all, it would have been a shame to waste a good French Maid outfit. "Please, Mistress, please fuck me...I'll be a good little maid slave, I swear." She laughed as she led me over to a nearby desk, so that she could fuck me standing up. I expected her to tease me more, but I guess she needed it almost as much as I did at that point. She simply greased my boi pussy with spit and cum and stretching me while I moaned around her fingers, and then pushed her cock inside me. I wasn't sure if she whimpered or I did, but either way, we both knew what we wanted at that moment. She wanted to fuck me hard and I wanted to get fucked...hard

That was when I noticed I was looking out a window and that we'd forgotten to close the blinds...and when I saw that twerpy little runt, Dale, stating through the window with a sadistic smile carved across his face. That was when I knew I was about to get fucked...hard...and that it would never end...



Young Master Ch. 04



"I can explain..." I was standing in a French Maid outfit, with a sissy's cum still dripping from my chin because as usual she missed a spot, and I had just been caught bent over a desk getting pounded from behind...all I needed to make it the perfect shit storm was for Dale to notice my cock was stick disturbingly hard in my panties for some mind boggling reason...

"Heh...this should be great. Okay, explain yourself." If Dale's grin grew any wider, his face would have split in two, but I wasn't so lucky. The runt of the litter amongst my domineering dickhead step-brothers, he was savoring this opportunity to feel like a real man instead of a bratty twerp. He stood there looking at me as if he actually expected me to explain myself. Isabella looked on with the same morbid curiosity, still stroking her hard cock waiting for a chance to use it..."well, aren't you going to explain why I just saw you getting fucked by your sissy?"

"Oh...sorry, I didn't actually think you'd give me a chance to explain...uh, I've got nothing...it's exactly what it looks like...what else could it be? But please..." I was about to ask him not to tell, and then I realized how stupid that was. Even before I got my very own sissy slave he hated me like poison. And since I made the sublimely stupid decision to slap him in his snotty little face, I think it's safe to say he wouldn't piss on me if I was on fire. Then again, maybe he would piss on me, but only so he could set me on fire again afterward.

"Please what? Please don't tell anyone? Please don't drag my sissy ass out of this room and show my step-brothers what a perverted little pussy boi I am?" I cringed as I imagined what Dirk would do if saw me dressed like this. He probably would have made an exception to his 'no flat chested sissies' policy just to put me in my place. The thought of what his bludgeon of a cock would do to my asshole made me wince...and whimper shamefully. As for Darius, I couldn't begin to imagine what he did to poor Cunt that made her screams ring out from his room at night, but I had a feeling he wouldn't hesitate to enlighten me if he saw me dressed like this. But even as I tried to block out the image of his dead eyes leering at my tortured flesh, I couldn't stop thinking about the look of almost religious fervor in Cunt's eyes when she looked up at him. A tiny, twisted part of me couldn't help wondering what it felt like to be so completely devoted, so totally destroyed. Lately, it had come to seem a tempting alternative to facing reality.

"Is that not it? Hmm maybe it's please don't tell my monomanically masculine step-father that I've spit cum all over his family tradition...but then again, I'll bet you're more of a swallower, aren't you?" I swallowed a gulp as I saw my step-father using my sissy like a piece of fuck meat, and I couldn't help but shudder and squirm now that it was the image of him doing the same to me, only much less gentle twisted simmering in my mind. I tried to picture myself as hating every sweat slick second, but with all I'd been put through in the last week, all I could see was my lost little gurl look staring back into the mirror that tortured lust stamped across my face advertising to anyone that saw it that I was a dick desperate sissy and that I'd do anything to cum. I couldn't decide which would be worse, the cold hard reality that my step-father would deliver me to Hell personally to ensure I did not enjoy a single whimper of my punishment, or if my demented day dreams came true, and I really did love being turned out by the man that had robbed me of everything. 

"Or maybe, just maybe, it's please, Dale, show me how a real man treats a sissy. If you do, I'll make sure you never have a dry hard on ever again. Is that it? Because honestly, as much fun as watching dad tear you apart with his bear hands, it's not enough. I would still spend another two years a walking hard on. But now...if you want me to keep your little secret, you'll provide me with my very own kept sissy to use and abuse whenever I feel like it." Throughout his entire tirade, Dale puffed his chest, curled his pouty lips into an almost impressive snarl, and tried to add so much weight to his voice that I thought his diaphragm might pop under the strain. He was a little boy, playing at being a man...and that frightened me even more than both his brothers and father combined. They had nothing to prove, but Dale, I shuddered to think what he'd do to poor Isabella to prove himself a 'real man'... 

"Sigh...fine, you can use Isabella whenever you want. As long as you never tell anyone what you saw today." I felt like I was chewing out a piece of my own heart. I still didn't know why Isabella played the games she did, and I still didn't know if the kindness she'd shown me was little rays of the real Isabella shining through the clouds or just more smoke and mirrors, but I knew one thing for certain...when she looked at me with her eyes filled with wet contempt, I knew I'd lost whatever it was we might have had. She could never respect me as a Master now that I'd proven myself the worst kind of coward, the kind that would let someone else suffer in his place, and I'd lost any sympathy she had for me as a sissy as well for delivering her to such a pale imitation of a real Master. I didn't things could get any worse. But of course, things could always get worse...

"Who said anything about using your sissy..." Dale grabbed a clump of my hair and pulled my neck back with a sudden painful lurch, before I could scream, his lips had formed a seal against mine, I screamed futilely into his mouth as his tongue wriggled against mine like a diseased worm. His free hand slipped below my absurdly short skirt and groped my buttocks clumsily. He had all the finesse of a thirteen year old's first fumbling with his cock, and half the discipline. He slobbered on my cheek as he broke the kiss and then looking at me with a confused mixture of absolute lust and hatred, spat at me, "God damn you for being so beautiful..." And then his hand was a blur, I heard the blow before I felt it, my eyes stinging as I left an arc of tears following me to the ground. 

Dale stood over me, panting, his face red with rage and desire, and I didn't know which to be more afraid of...or which one was starting to make my cock stir to life in my panties...I begged my body...not him...anyone but him...but she is a heartless bitch...or maybe a ruthless bastard...either way, I knew things were about to get even worse... "Well...what are you waiting for, sissy? We both already know you're a little cock sucking slut...so pull out my dick and show me what you've learned from your sissy!"

I was hesitant, but not for the reasons I thought I'd be. Not because he was technically family...if anything, that paper thin distinction only made it seem more taboo and illicit. And not because he was an asshole...no, the worse someone treated me, the faster I seemed to melt. And it wasn't because he was a man...which was pretty terrifying to realize. Was I gay? Bi-sexual? Did it count as bi-sexual if I was attracted to both sissies and real men? Whatever the answer, I couldn't keep denying the sheer throbs of power I felt radiating off my step-father when he pounded my sissy in front of my lust glazed eyes, or the way my asshole quivered when Dirk teased and humiliated me in the gym. Maybe that's all it was, the thrill of surrendering to a stronger force, losing all control and feeling free to just enjoy the mindless bliss that followed. And that's why I hesitated, not because Dale was a man, but because he most decidedly wasn't...

With Dale I couldn't give myself the easy excuse of submitting to a stronger force. In an extremely fucked up way, it felt natural to perform disgustingly unnatural acts at their bidding, because I'd always been raised to believe that inferior people existed to serve their betters...only I used to think I was one of the betters. But Dale wasn't better than me...I refused to believe that. He was just a snotty spoiled shit smear that reminded me so much of myself that I wanted to strangle him...and yet there I was, fumbling with his zipper on his leather pants, which I can only assume where his failed attempt to look more intimidating, about to choke on his cock..."Come on, sissy! If you don't have my cock in your mouth by the time I count to three, then I'm telling my dad on you!"

"One.." I wanted to punch the tattletale right in his nuts, but instead I was pulling his cock out, cursing myself as I can feel it stirring in my hands, knowing just from one squeeze that it was bigger than mine. "Two..." much, much bigger. A little bigger than Isabella's even, and just as thick. I wished he could have had an average sized three and a quarter inches like me, but no, he had to be hung like some kind of freak with an almost eight inch cock..."Thr-" I didn't think as I ran my tongue slowly up his cock and swirled it around his soft, spongy head. I blushed as I realized that even though he tasted different than Isabella, I didn't savor the flavor any less. He was a little more robust, and I found myself wondering if every cock had its own unique taste, and if so, what it would take to become a true connoisseur. Then I remembered who that delicious dong belonged to and I felt my stomach lurch. I pushed the thought out of my head even as I slipped Dale's dick into it, my lips forming a tight seal around the head to make sure it didn't go anywhere before I could swirl my tongue around it.

I decided to just switched off my brain and let Isabella's lessons kick in. That made it easier for me to enjoy the taste of his pre-cum as I sucked it from his piss-slit, my hand pumping his spit slick shaft to try and get more of his gooey goodness. Again I was flummoxed in trying to place the taste. This had the same qualities as Isabella's pre-delicacy, but also some more complex notes...was there a trace of sea urchin? Whatever it was, I knew I needed more to make an informed decision, preferably coating my face, mixing with what was left of Isabella's earlier eruption. I had hit a natural rhythm, operating on muscle memory and a natural instinct I would have been appalled to realize I had if I was still capable of rational thought. Instead I surrendered to the tender mercies of mindless pleasure; feeling my cock throb painfully in my panties as if I vicariously got off on making a superior cock throb and swell in my mouth. And then Dale had to open his big fat mouth...

"NNH Damn, I was going to start fucking with your head, you know, call you a sissy cocksucker and all that, but fuck if I you wouldn't take it as a compliment right now." I tried to ignore him, hating him for being so right. I felt his cockhead tickle my throat as he forced his way deeper inside me. His prick was curved upward, a different shape than Isabella's which produced a different sensation scraping my throat: more raw, more intense. I tried to drown out his words with the wet squelching sounds coming from my throat but he kept talking, "I mean, isn't it a little more traditional to at least pretend you aren't loving this? I was kind of looking forward to pushing my cock past your reluctance and fucking away every last bit of resistance. But look at you, with that dick drunk sissy stare, all you need is some tits and no one could tell you apart from any of the other harem gurls." 

I couldn't look at him anymore, his sharp tongue and piercing stare where cutting through my dreamy haze, making me acknowledge the reality of what I was doing. Unfortunately, when I turned my eyes to the right, I saw Isabella stroking her hard clit, her eyes burning with contempt and predatory lust. I couldn't bear seeing that look in her eyes, not with my step-brother's balls resting on my chin as my throat closed around his hard manhood, making me feel like the dizzy little sissy bitch was calling me. I threw my gaze to the left, hoping to find some small corner free from eyes that seemed to see me all too clearly, but instead I found the worst pair yet...mine...

There I was in the mirror, my mascara running as tears filled my eyes. Not for the reasons they should have, because I was so ashamed of what I was doing that my soul was screaming out for forgiveness and my eyes were trying to wash away the filth. No, I just was so desperate to be a good little cocksucker that I was letting him use my throat like a cock sleeve, forcing tears as my blood pressured reached a boiling point. My flush face did wonders for my make up, accentuating the smeared lipstick across my cheek and his cock and bringing out the lovely contrast of my pale comely skin. I saw the look of mad lust in my eyes, the shame turning into something worse, something sick and depraved and sickly sweet delicious. I didn't see myself anymore; I saw a sissy slut maid: a living, sucking sex toy made to be used and abused. I wanted to see her body go tense as Dale filled her with his arrogant seed. I wanted to see her stain her panties with sticky sissy spurts. But more than anything, I wanted to believe that she wasn't really me. But I had the most terrible suspicion that she was more me than I'd ever been. I felt Dale's cock surging in my throat and I knew it would be soon. I bobbed my head back and forth in a frenzied fervor, frantically chasing the brain dead high that would let me escape my reflection for a few precious moments. That's when Dale grabbed my hair in his hands and pulled me off his cock in one savage yank...

"Jesus H Fuck! What the Hell happened to you? A few days ago you thought you were man enough to slap me in the face, and now you're whimpering because I pulled you off of my cock. Is this even blackmail anymore? You look like a sissy, walk like a sissy, you dress like a sissy, and you definitely suck cock like a sissy. Seems to me like you'd want me to tell on you. Maybe then dad will throw you down in the basement with the other sissies where you belong." Without his pulse pounding deafeningly on my tongue, I was beginning to hear myself think more clearly. As I did, I couldn't help but wonder if he was right. This week had been one humiliating experience after another, wearing me down to a soft smooth little nub leaking in my panties at the thought of being collared like the naughty little bitch I was. I would immediately recoil in horror at the thought of being sent down into that living Hell, only to wonder if it might be my salvation. Dressed as I was, humiliated and horny, it was impossible to think straight, and I was too scared of where it might lead if I started thinking sissy. Which left only one alternative...I had to stop thinking altogether. But to do that, I'd have to convince Dale to stick his cock back inside me.

"Please..." I looked up at him, stupidly searching for some semblance of mercy for a moment, "please..." I could barely form the thought, much less the words. The idea of debasing myself even further for the amusement of a little boy made me want to vomit...but he was a little boy with a big cock, and I needed it to escape the shame of wanting it in the first place. So I vomited up the words, "Please, please fuck me...muh muh gah guh" I couldn't say it; couldn't call him Master. Not with that razor sharp gleam in his eyes, ready to cut me to ribbons. I knew I'd never live it down if I submitted so completely to him, but then I realized that sucking his cock and begging to get fucked was probably not going to be laughed off as madcap shenanigans either. In for a penny, in for a pounding..."Please, Master, please fuck me...I need it."

I yelped as he pulled me off the ground by my hair and dragged me over to the bed. I tried looking over to Isabella for some sign of support, but all I saw was contempt. She looked at me like I was just another needy little sissy slut, the kind she had to play den mother too down in the basement. I knew in that moment, that I would never be a Master in her eyes, never be a man, and as a sissy, apparently I left a lot to be desired...but judging by the way he tossed me on the bed and leapt between my legs, I was desirable enough for Dale.

I tried to suppress a girlish squeal of delight as Dale lifted my legs over my head, pulled off my panties, and aimed his cock at my quivering hole, but I guess I didn't do a very good job. "Holy shit...you even giggle like a fucking sissy. Really...it's pathetic, but also kind of hot. I almost wish you really were one of the harem gurls so we could get you some fat titties and whatever to complete your look. But then I wouldn't get to plow your ass for another two years, so I'll take a flat chested step-sissy over none at all." I squirmed in an almost unendurable mixture of pride, embarrassment, and aching need. I knew I would regret it just moments after I came, and a tiny part of me regretted it even then, but the hunger was too great...not just for the escape of a mind melting orgasm, but also my vanity's voracious appetite. I had always been praised and adored without ever having to do anything to deserve it. That is, until these step-mother-fuckers moved in and took away my life. So why was it that they were the ones I wanted to prove myself to? I wanted it so bad that I was willing to accept the pimp handed compliment of being passable enough as a sissy to fuck. Faced with the realization of how pathetic I had become, I did the only thing I could do...I bit my lower lip invitingly and fluttered my eyelashes at Dale, beckoning his cock inside me.

I made a sound like a wounded mouse as he used the full weight of his body pressing down on me to slide his cock into me in one steady push. Time slowed and the fabric of reality stretched thin and distorted. Every second seemed to slide past like sweet, sticky syrup and every inch he slid into me seemed to go on for miles. Isabella had already opened me up, and his cock was well lubed with my slobber, so he found no resistance as he spread my asshole to fit the shape of his cock. I cooed helplessly as the upward slope of his cock hit my sweet spot harder than Isabella's ever had. I was torn...I wanted to get to off, to escape to my own personal paradise, but I didn't want it to be as good as it was with Isabella. I didn't want his cock to slide back out slowly, teasing my eager little nerve endings and sending throbs of pleasure all the way up my titillated torso, past my achingly hard nipples, finally hitting my head with a burning blush. 

I knew I hated him. All the evidence I needed was in his smarmy smirk and the way his eyes bored into me with their disdainful lust like I was getting eye fucked. But then he slid back into me, miles and miles of cock stretched out over am impossibly long span of seconds, painful pangs of pleasure eating away at me from the inside, threatening to tear me apart. Sure, I knew I hated him...but my brain was telling me another story. Every time the hungry bliss bit into me, it's poisonous fangs would infect me, sending out a chemical cocktail of adrenaline, serotonin, and dopamine...a love potion #69 that drugged my senses and sent me spiraling down into a sissy haze. Looking up at him from leagues beneath a sea of lust, all I could see was the way his muscles popped out from under his smooth skin every time he plowed into me, the way he sheen of sweat made him glimmer, the way his eyes hungered for me, wanted me just as I was...and I needed him to want me. 

There was nothing left of the real me at that moment but a tinny little voice in the back of my head repeating the filthiest slurs, calling me "a nasty little fuck hole, a dick desperate diva, a flaming faux female, a humiliation junkie hooked on junk, a bitch, a slut, a cunt, a gash, a cum catching cooze, a tiny dick little boy playing dress up and taking a cock up his ass so he could hide from the truth...a sissy." They were angry indictments from the one voice I couldn't ignore...but then Dale's began picking up the pace, hitting my sweet spot and kissing it goodbye in a blur of movement that filled me up with soul searing love one moment, and left me achingly empty the next, only to fill me back up before I could take another breath. Suddenly, the voice in the back of my head was nothing but a vulgar valentine, a cruel compliment, a glob of spit on my soul that felt like a long, lingering kiss. My legs wrapped around Dale like a lover, pulling him deeper inside me as his polluted love pumped through my veins like battery acid, sending savage shockwaves across my body, every tender muscle contracting at once to all the way down to my throbbing clit, forcing its way out it in a declaration of pure lust, catching my chin with my sickly seed. Oblivious to his laughter, I lapped it up with my tongue and moaned for "MoOoOoooooore!"




Young Master Ch. 04



"You selfish little slut...how dare you cum before me? Don't you know the first thing about being a sissy? Then again, I guess I should be surprised, after all, you were a total fuck up as a man, it figures you would be a half assed sissy." He held me in place, with his cock kissing my heated hole, fueling its hunger but refusing to fill it. "Maybe I should just throw a load into Isabella instead. I know she'll put my needs first, and she's so much prettier than you." His words stung, bringing me to the verge of tears, but I knew that if I started sobbing he would just laugh and toss me aside. I was so close, that first eruption was merely a hiccup to the pleasure that lied just beyond the door to my sanity. I had to get him back inside me...and fast.

"Please, I beg you, Master! Please fuck me, breed me, brand me with your burning seed. I'll do anything you ask me to! Give you my allowance between my teeth like a dog, clean your room and polish your knob, I'll do your homework with your cock up my ass...anything! Just please fuck meeeeeee!" Every word tears out of me in a painful sob, taking sticky chunks of my dignity along with it. By the time I finished, I was little more than a panting puddle. I waited with bated breath, hoping he would reel me in and feed me the cock that had me hooked. He waited for maybe a full minute, give or take an eternity, rubbing his rubbery head against my hungry hole. All I could do was whimper and snivel, sending out sweltering waves of submission, and hoping it was enough to goad Dale back inside me.

"Okay here's the deal. You'll do everything you just offered for the next two years, and in exchange I'll let you be my personal fuck sleeve. But you do what I tell you to, and you make sure I cum first. Now, climb on my cock and go for a pony ride. My arms are getting tired." I should have told him to fuck off or spit in his face; instead I spit on his dick and told him to fuck me as I hovered my winking rosebud over his hard shaft. I sank down with a sigh; impaling myself on his manhood.

"OoOoOOooOHHHH!" his cock forced a moan all the way from my ass to plump lips, touching off the nerves that were just starting to cool after those interminable seconds deprived of hot flesh on tender tissue. It felt so right to slide down to the root as he laid back down on the bed, his hands crossed behind his head in an expression of effortless control. My ass had already grown accustomed to his cock; having been reshaped to take his full length and girth, now it felt empty without him all the way inside me. I clenched my sphincter and hugged his cock with my soft anal walls, feeling his cock return my affection, kissing every frazzled nerve all the way up to my melting mind, sending that true love COCKtail all the way back down and curling my toes. I looked down on him, trying to remember a time when I hated him and finally giving up when all I could see was the man pumping me full of dirty love. 

But being full of love wasn't enough anymore, I wanted to explode, and I knew how to lite the fuse...I peeled myself off his cock, feeling my spit dripping back down to his rosy head, and slamming back down onto him with a shuddering force that sent a quake of quivering pain that rang in my teeth and left a dull buzz in my ear. It was a welcome hurt, like the prick of the needle about to flood me with sticky sweet heroin. I wanted to savor the toothache-sweet hurt for as long as possible, slooooowly sliding up and down his throbbing sex, but I NEEDED him to hit my golly-gee spot faster and harder to take me to Shangri-La-La land. My legs throbbed as I bounced up and down at an increasing pace, his perfectly curved cock pounding my prostate even harder at that angle and I was soon lost to the building drum beat of orgasmic bliss.

"NNH That's right! Keep riding that pony! I'm about to fill your sissy pussy with a real man's cum!" I felt Dale's thin fingers dig into my fleshy buttocks, squeezing out an animal moan as he pulls me down hard onto his surging sex. I felt his heartbeat inside me, and at that moment, I forgot that he was a bratty, blackmailing bastard and saw only the best in him, or maybe I just felt the best of him in me. Whatever the reason, I couldn't resist taking his head in my hands and pulling my lips into his, sucking his tongue right out of hit mouth and making out like prom dates. I felt his heart flutter as I slammed my hips down as hard as I can, causing his heart to swell and burst inside me, coating my raw, ravished guts with his cum. My heart exploded too, sending a flood of pure love shooting from my clit and onto my stomach. He got over his initial shock at my sudden aggressiveness and immediately reasserted his control, grabbing me by the hair and pulling me off his succulent lips. I laid on top of him, my mind lost, my tongue straining to taste his again. He just sneered as he spit in my face...and then he pulled me back down into a hateful kiss, the passion of his contempt making me melt into his embrace as I laid on top of him, my whimpers pouring down his throat like a sweet wine. 

I had reached that perfect place of nirvana nothingness, floating on cloud nine in a state of harmony and peace, blissfully blank and euphorically empty, free from the fear and the shame and the pain. Time was meaningless there...I floated forever and ever...and then I came crashing to the ground "What the fuck?! Who told you to cuddle with me?! Shiiiiit! That's really fucking gross, dude. I might have to rethink this whole secret sissy business if you're going to fall in love with me." I looked up at Dale from the floor, aching everywhere as feeling returned in hot sobs of regret...I looked at myself in the mirror, the well fucked sissy maid...but underneath the smeared makeup, I could see Byron dying underneath. How could I let him do that to me? HIM?! How could I beg for it?! I looked into his eyes, my lips struggling to form the words strong enough to convey my hatred for this little boy playing dress up as a man...but they were too big to get out. I just ended up sputtering, my eyes blazing...

"Now that's what I like to see..." He pulled my face close to his, our lips mere microns apart, I flinched helplessly in his hands, desperately trying to pull away as my face contorted in disgust. "Yes, I think you're even more beautiful this way..." he pressed his lips against mine, I tried to turn away, but he held me firm, kissing and sucking on my lips no matter how tightly I pursed them. Finally he threw me back to the ground, a sob trailing behind me..."Heh heh. Alright, this might work after all. One more rule. You always wear the underwear I last fucked you in. You can wear your man costume over that if your feeling kinky, but I don't want you forgetting what you are underneath, not even for a moment. And anytime I text you, I want you to hurry up to my room and ready to serve. Understood?"

I didn't have a choice. I tried to tell myself it was because he was blackmailing me...and for the most part it was. But another part of me was grateful I could use that as an excuse. I meekly whimpered into the floor, "Yes, Master." and Dale left without looking back, his hyena-like cackle trailing behind him a parting gift. I just curled up into a little ball, rocking back and forth, crying like a little sissy, hoping Isabella would wrap me in her arms and tell me everything was going to be alright. I heard her make her way over to me, felt her hand stroke my hair, and screamed as he grabbed a handful and pulled...

"You will never be my Master now! And for promising me to a boy..." she spat the word out like it was poisoned pig shit "I will never trust you as a sissy. So I'll keep your sick little secret for as long as you can manage to hide it, because that's the sissy code...but if you ever try to treat me like your slave again..." she cupped my balls in one hand and firmly squeezed, "I'll show you how I deal with disobedient sissies." I could only nod as tears welled up both from pain and regret. That's how she left me, sobbing, sticky, and shaking, wondering how things could possibly get worse.

...

It only took a day for me to find out just how much worse things could get. I was lying in bed, wishing I could stay there forever. Then I got my first text from Dale, reading, "Cum on up to my room. Isabella found a special outfit for you to wear." I cringed to think of what it might mean. I cursed my cock as I felt it throb in my lacy panties, hoping I could show more self restraint than I this when I got to Dale's room, but not betting on it. I slip on some clothes that I don't plan to be wearing long and take a long, hard look at myself in the mirror, telling myself I'll do whatever he wants me to, but only because he wants it. I told myself I would not beg, I would not kiss him, and I would not cum. I kept telling myself that all the way up to his room, and I had almost convinced myself I could do it. After all, I genuinely hated Dale, and I was pretty sure I still hated being humiliated and abused...the fact that it made me so horny I couldn't think straight was just a fucked up defense mechanism; one I planned to ignore this time. I would just have to suffer all the frustration, all the agony, and all the shame, and without the sweet escape of mindless pleasure...

My brave pronouncements fell to pieces the moment I saw what Dale had planned for me to wear and heard his plan for what I would do in them. "Aren't they cute? Isabella borrowed them from Bambi". He held up a pair of pink, ruffled rumba panties and one of her tiny, sexy-tea-party dresses. I realized I was going to get to find out how I'd look in her panties after all. And things just went downhill from there...

...

"Oh pwease, Daddy Bear Sir, pwease punish your naughty widdle gurl with your big, bad Daddy-dick!" It wasn't my proudest moment...but after three hours of playing sissy surrogate for Bambi in his twisted fantasies, I began to get into the role. I had promised my self I wouldn't beg...and I really meant it at the time. But after breaking my promise not to cum at least eight times over and my promise not to kiss him an hour ago...and I broke it again and again and again...one more promise didn't seem to matter. Maybe it was Bambi's fault...I'd never realized how freeing it was to be a child-like whore, how strangely reasonable the contradiction seemed once I embraced it. Of course, my reasoning may have been influenced by a constant flow of pure 'wuv' gushing through me with every flutter of my heart. It went on for so long that time became as meaningless as dignity or manhood and I went in and out of the blank place so often that reality and unreality blurred. Every cell in my body hummed along to pornographic lullabies. I didn't so much break my promise, as fulfill Bambi's...of course I was the one that had to clean up Bambi's mess once the haze cleared.

It was like scraping myself off the walls. Slimy globs of me, pale and weak in the light of harsh reality. Dale's grating voice bouncing around in my head like a .22 caliber bullet. I couldn't stop crying, couldn't stop telling myself to stop crying, couldn't stop from hating myself when I couldn't. But I hated Dale more. And I vowed to myself that I would remember this the next time he had an outfit spread out for me, that I wouldn't forget it when he spread me out. That every time he forced me to cum I would hate him even more. I had to...it was my only hope...

...

He gave me a day off. It was almost worse that way. Constantly worrying that any moment the phone would vibrate and I'd be summoned to his room. The bitter sense of relief and disappointment when I wasn't. The frustrating and emasculating realization that I couldn't even jerk off anymore. Fear and self disgust rendered me paralyzed...impotent...so when a second day was almost over and I hadn't gotten a message, I began to worry. I realized that when I fumbled for the phone desperately at the first buzz that I had already broken my promise. "Cum up to my room. Time to help me with my homework."

I wasn't surprised to see one of Sakura's many school girl uniforms hanging from the door, or the Hello Kitty cotton undies. Somehow their lack of sexiness only made them squirmier as I slid them up. He patted his lap and put his homework in front of him on the desk. I realized with a shudder that I was going to be keeping a promise after all, just not the one I wanted...

...

"Oh most honorable Dalesan, please to be fucking my most humble asshole harder. Ah ah AIEEEEEE!" I had just triple checked his calculus homework and verified there were no errors. Funny thing...I barely passed calculus when I was in high school, and that was after buying the answers to the final. I guess that cute little ribbon he tied around my cock to prevent me from cumming was all the incentive I needed. When he finally took it off, I felt my soul shoot out of my body in a hot milky jet. I looked down at my face, flush and empty, but ecstatically happy. I realized why Sakura constantly humbled herself, how beautiful it could be to deny the self, to become one with the universe...to become a purpose instead of a person. I looked beautiful from that angle, flopping on his lap, my head thrown back across his shoulder, my tongue lolling out the side of my mouth as he sucked on my neck, tasting my pulse. It was only when I finally had to return to my body that I understood how ugly it was from the inside...

It wasn't as much fun finishing his homework after that. Sitting in squishy panties, flinching as he flicked my ear or blew on the back of my neck every moment worse than the last and knowing you aren't even half way done. By the time I finished his essay on 'The evolution of gender roles in post-modern America', it was all I could do to drag myself to bed and hope that things really couldn't possibly get any worse...

...

The problem was...they didn't...at least not right away. No, Dale decided he'd rather make me suffer, rather see me squirm while I waited for the other foot to drop. Actually that's probably just wishful thinking. The truth is, Dale didn't think enough of me by that point to go out of his way to torture me. He knew all to well how willing I was to torture myself for his amusement. And boy oh boy, did I have a grand old time of it. Three fucking days without a so much as an "lol" texted to me. Three days of white knuckle terror wondering how he'd top his last stunt and blue balls wishing he'd get it over with. By the time he finally texted, "Cum up to my room. Time to pay me." I couldn't stop myself from running, but what he had prepared for me stopped me dead in my tracks.

I wondered when Dale had picked up a pair of silicon breast forms, that is until he showed me my credit card bill. So much for my little discretionary income I had left, instead I had liquid assets. Their weight felt strangely exhilarating, like I was stepping into Lola's skin, only with the safety net of knowing I'd lose the extra gravity when this was over. I could barely stuff them into a DD bra and the leather halter he had me wear just barely covered them, creating the illusion of a pair of very real, very large breast, straining to spill out. When I slipped into the leather mini skirt that gave a peak of the bottom of my perky ass and stepped into a pair of fuck-me-fishnets, it was pretty obvious this was going to be a ten-dollar-whore/belligerent john fantasy. But of course, it was much worse than that...

...

"Si, papi, y then he filled my culo up while the other two took turns making mi boca into a fuck-hole. The one stretching my ass had a nice cock, but not as grande as yours, papi." I was only telling him what he wanted to hear: fantasy encounters of a ten-dollar running a half off sale telling her pimp every dripping detail about her workday. Thank goodness I took Spanish in high school so I could stay in character. And that's all it was, staying in character. It started as the most humiliating ordeal he'd put me through, making me come up with increasingly degrading fantasies and telling him how much I loved them. To make it worse, I had to hand him over a little more of my allowance each time, as if I actually had earned it sucking cocks down at the bus station. But once he hiked my skirt up and starting fingering my asshole, I discovered my character's motivation and things came easier....

In a way I liked being Lola better than I liked being me. She wasn't ashamed of who she was, quite the opposite. Calling her the dirtiest whore on the eastern seaboard wasn't an insult, it was an accomplishment. Like winning the Nobel Piece of Ass Prize...or at least, that's how I imagined her to be. Latinas are fiery passionate lovers after all, and the way she beamed when Dirk slapped her ass, you'd think she owned him. At any rate, the more stories I told, the more I found her voice, and the more I got into sucking Dale's cock while he counted my money. Even when he laughed at me and called me a "puta punk bitch" after he coated my face with his cum, all I could do was smile and lick my lips. Maybe it was the pride of coaxing the biggest load from him yet, maybe I was just in Lola Land, or maybe it was that the moment his seed hit my face it sent a chain reaction of giddy glee all the way down to my own squirting sissy stick. Whatever the reason, all I wanted to do was tell him an even filthier story so he'd get hard enough to fuck my ass...

Which is what brought us to the senior center gangbang and my last five dollars. At the time I considered it money well spent as every shuddering blow of his hips drove his cock deep inside me, sending ravishing ripples across my flesh and making my 'breasts' slap hard against my chest. As I came, I became Lola completely, and in that one perfect momento, I felt bonita, and I loved it. 

It was so perfect that I got almost half way back to my room before my cum glazed haze wore off and I started to relive the stories as me, and retch at the thought of the filth inside me. And Dale, considerate as ever, was kind enough to send me texts of some of the 'choice bits' that made him 'lol'. I tried to see further than a day or two in advance, tried to fathom enduring this for even a month longer, much less two years, but I didn't have the courage to continue. I just pushed it out of my mind and tried not to ask myself if things could get worse...but life has a funny way of answering the questions you don't dare to ask. Yeah life can be real fucking funny sometimes...

...

It was a week before Dale texted me again. I was a raw nerve, my guts felt like broken glass and my balls felt like water balloons filled to the point of bursting. I was beginning to debate going up and knocking on his door unbidden, asking if he needed any help sucking his cock. Even considering it filled me with a revulsion that made me want to scrub my skin with steel wool and sulfuric acid. But 'fortunately', Dale decided to call on me before I could sink that low. "Cum on up to my room, Cunt." If only I had known the soul crushing deprivations I would be subjected to when I got to Dale's room, I wouldn't have bothered to worry about the last tiny shreds of my self respect. 

...

"Oh come on, Cunt...you've still got plenty of room on that baby smooth skin of yours. You can't have run out of slurs already." I was staring into a mirror, getting a reeeeal good look at myself, seeing what kind of faces I make when instead of running from the reality of what I'd been reduced to, I instead embraced it...or at least surrendered to it...

The outfit Dale had picked for me was much more conceptual this time. He had me go into the shower and put on some foul smelling lotion that made what little body hair I had fall out. I thought being dressed up was emasculating...but that was nothing...NOTHING compared to seeing myself as I was, having to face that even without the clothes, even without the makeup, I still made a fairly fuckable sissy. Now that I was silky smooth and naked, Dale had me as his own personal canvas, and little shit that he is, he was only interested in scrawling graffiti. 




Young Master Ch. 04



The worst part, and its funny how subjective 'worst' gets after awhile, was that he made me come up with the slurs he scrawled on my pale unblemished skin. I never truly understood how much I despised myself until I saw it in all caps written across my forehead. But after enough abuse and self recriminations, I guess I finally learned to accept myself because the filthy truths that covered me didn't seem so unbearable anymore, but maybe it was just because I was riding a near constant cock high as Dale deep dicked me against the mirror. He must really get into his art, because he lasted longer with Cunt than he did with any of the other sissies. When he finally filled me up so full that I could swear it was his cum spurting out my cock, I didn't even hesitate to lick the mirror clean. And I knew that at least I had finally hit rock bottom...

God...one of these days I'm going to be right about that, aren't I? I mean...there has to be a bottom...there just has to!

...

THREE...FUCKING...WEEKS...

After the first week I thought I was going to go insane if I Dale didn't use as his surrogate sissy again, which I guess meant I already was insane by that point for needing it so bad. I did manage to find some relief, fucking a pair of cum-caked panties while I thrust my fingers in my ass, pounding my sissy spot until I managed a weak, whimpering squirt or two. But in the end, it only left me dissatisfied and hungry for more. I would see the other sissies prancing about the grounds, and instead of imagining unleashing a torrential flood of cum in their tight holes, I'd imagine being them, bouncing from one hard fuck to the next with mindless glee. 

Finally, the effort in fighting for the table scraps of my soul just didn't seem worth the effort. It's not like Dale could think any less of me than he already did, and I wasn't far behind him in that regard. So with a sigh of resignation and relief I knocked on his door. After an interminable wait, he cracked the door, covered in sweat, his face flushed, and his well coiffed hair in disarray. He seemed annoyed, snarling, "What do you want, Byron? I'm busy."

I couldn't speak at first. I was taken aback by his lack of interest...and why did he call me 'Byron'? But I didn't come this far to give up, not when I was so close. I summoned every ounce of strength I had, stuttering, "wuh wuh Well, yuh yuh you haven't asked me to uhm err clean up after you or do your homework for a few weeks. And I uhm, owe you a lot of allowance...so I was uh wondering if you wuh wuh wanted me to whimper suh suh suck your cock or anything." It took every ounce of willpower I had to force the words out, and to look him in the eyes the entire time, seeing them dance with cruel mirth and they saw the naked hunger in mine.

"Oh man, you've got it even worse than I thought. Come on inside, I'm sure I can think of a way for you to help me after all." I nodded submissively, eagerly accepting whatever price I would have to pay to get what I needed, already drooling over the images flashing in my head...but I wasn't ready to accept the image before my eyes...Isabella, looking at me with a mixture of annoyance and disgust, completely naked save for a leash that was tied to Dale's bedpost. This was why he hadn't called for me in almost a month...he had traded up. I thought I was going to hyperventilate, ragged, vicious sobs welled up in me...I looked over to Dale, and he laughed, saying "Ha ha! Look at you, jealous of your own sissy. I never dreamed that not fucking you would be more devastating for you than fucking you. Sorry, Belle, but Isabella is a way better lay than you. She actually knows how to fuck me back, instead of just taking my meat like a selfish little slut. But I tell you what, maybe there's room for you in this new relationship dynamic after all. See, you killed my boner when you interrupted me, so why don't you get me nice and hard for Isabella's tight ass?"

He wanted me to be a fluffer for my own sissy. To sit obediently and watch while he proved that I would never be man enough to fuck her, or sissy enough to get fucked by him. To my horror, I didn't even consider saying no...that's how low I had sunk. Even the slightest possibility of getting off was enough to make me fall to my knees and obediently nurse on Dale's succulent sack until I felt his cock rising, caressing my cheek like a lover. I tried to draw it out as long as I could, slooooooowly sliding my tongue up and down his cock, pursing my lips against his hard, hot flesh and running them back and forth his shaft, taking his silky, smooth head into my mouth and softly sucking until I was rewarded with a single drop of pre-cum, marveling in its flavor...I'm sure I noticed notes of fresh goat's milk. But it ended almost as soon as it began, his cock pulled away from me, drool and whimpers trailing after it. "That's enough!" he said sternly, "If you want to stay and watch, you will be a good little gurl and be quiet." I opened my mouth to protest, but forced it closed with my hand, nodding mindlessly and following behind him on all fours, looking up at him as he climbed over my sissy...

"Not to speak out of turn, Master, but I think it would do Bella good to get a closer look. Maybe she could crawl onto the bed with us and help you stick your dick in me...or maybe even keep it nice and lubed with her tongue as you fuck me." I looked up at her, too stunned to hide the hurt stamped on my face, but she didn't even give me a second glance. That was the worst part of her latest variation of cruelty...how utterly detached it was. She didn't even think enough of me to hate me...at least that would involve some passion. Instead, I was just another sissy to her, and not much of one from the looks of it. I couldn't blame her, as much as it tore me up inside, the only reason I hesitated to jump up on the bed and become my own sissy's cuckold, was because Dale hadn't given me permission yet. All he had to do was nod...

I was a giddy jumble of nerves, like butterflies were throwing up inside my stomach; the fumes making me drunk and dizzy. I wanted to get it over with, to jump into the void head first, but at the same time I couldn't help feeling the painful pull of regret. I had lost Isabella, I couldn't kid myself about that anymore...but to officially offer her up to the man I hated...and needed...more than anyone else in the world...it was a tough pill to swallow. Then again, I'd swallowed worse. I felt Dale's cock throb in my hand, and suddenly my only regret was that I wasn't sliding it into my own neglected asshole. Still, the sheer wrongness and weakness of the act had me throbbing in my panties. I did a swan dive into the void and aimed Dale right into Isabella's dark tunnel...

"UNH Fuck yes! You see that, Belle? The way she swivels those hips and milks my meat with her soft, but oh so tight muscles? Fuuuuuuck...she could crush a walnut with her ass or carry an egg without breaking it, that's how much control she has of it. That's why you're the fluffer and she's my number one gurl. Speaking of which, why aren't you sucking my balls?" I listened intently to every callous word, hoping futilely that maybe if I learned well enough, he'd throw a fuck my way every now and then. But then I remembered what I was here for, and with a blush, I crawled underneath Isabella so that my head was right below Dale's balls. I took them into my mouth one at a time, swirling my tongue around them and sucking on them dutifully, trying my best to time my sucks with his thrusts, to maximize his pleasure. Suddenly, he bucked forward too quickly for me, and my tongue was running across his perineum and between his firm round buttocks. "Ooh...someone wants too earn brownie points. Alright, I'll let you eat my ass a little if you want to prove what a good little sissy you can be."

I was stunned...just when I thought I'd hit rock bottom, the floor fell out from under me...but of course I didn't resist. I only paused long enough to close my eyes and said a silent prayer to the god of cleanliness. I spread his cheeks as far apart as I could, indulging in a guilty thrill of squeezing the taut globes, and ran my tongue around is starfish is slow circles. It had a slight tang to it, but it wasn't unpleasant, almost like sun-dried tomatoes...so decided to go whole hog and speared my tongue inside his tight hidey hole. I heard Isabella moaning louder as it fueled his piston-like thrusts, and felt that strange mix of filthy pride, one which seemed less and less contradictory with every surrender. My own member was leaking in my silken hiding spot and I felt the long awaited release of a squirty subby shamegasm simmering inside me, but apparently Isabella saw the slight bulge in my slacks, because she thumped my cock hard enough to scare it back into hiding. I whimpered into Dale's asshole, which made him fuck Isabella even harder. 

"Fuuuuck! Okay, I'll admit it, Bella. You finally found something you're good at. Now get that filthy tongue back up to my cock and lube it up for your sissy." It was the next best thing to cumming...hearing Dale begrudgingly admit that I did a good job...that I was good at something...anything. It was almost worth the pain radiating from my cock up into my guts like a hot lump of coal. I thought that maybe if I did a good job licking his shaft as it sawed in and out of Isabella's sissy pussy, just maybe he'd praise me again, maybe even Isabella would be impressed. It's funny how low you set your sights when you've been face down in the gutter long enough. Yeah, it's fucking hilarious.

I had to dart my tongue really quickly to get between them, straining and stretching for a fleeting flick of their flesh. Tantalizing bursts of flavor...her ass on his cock...my own drool dripping back down into my throat...the sounds of moans and the slap of flesh on flesh filling the room...it was the most erotic experience I'd ever had without being allowed to get a hard on. Heaven and Hell danced on my tongue, I was close enough to taste the objects of my desires, but not to get my fill. And of course, Dale had to show off his endurance, cocky bastard lasted an hour before he finally filled exploded inside her. He gave her a loving slap on the ass saying, "Good work, babe. Now you two clean up and get the fuck out of here by the time I finish my shower." 

Before I could even move, Isabella was sitting on my face, smothering me with her plump, perfect ass. I panicked, screaming into her ass, but she showed no mercy, hissing "I don't care if you can't breathe! You'll suck every last drop of cum out of my ass before I let you up...and don't you dare swallow a drop of it!" She didn't have to tell me twice...I planted my lips around her succulent sphincter and dug every delicious drop out of her luscious love tunnel. I was surrounded by soft flesh, light headed and swimmy, my mouth full of ambrosia, but not daring to keep any for myself. She finally rolled off of me and pulled me up by my hair so that my mouth hovered over hers. I opened my mouth and let my hard earned reward spill into her mouth and down her throat. For a moment our lips grazed each others and our tongues drew ever closer...I dared to dream we might even kiss...but then she just tossed me aside like wet garbage. She didn't say a word, just left me sissy shocked and sniffling and went on her way.  

I waited until I was sure I wouldn't have to cross paths with her in the hallway and I scurried down to my room, racing to my shower so I could caress my clit with this shameful pride still fresh in my mind and lingering on my tongue. I moaned as I painted the shower wall with a weeks worth of pent up sissy squirts and fell to my knees. It was awful, almost unbearable...but maybe it was still just good enough...

...

It went on like that for another month...and maybe it would have gone on like that forever. It's amazing what you can accept when the alternative is even more unacceptable, but then came the straw that broke the sissy's back. In my case, it literally was a straw. Dale had just finished pumping my sissy so full of semen I could practically hear her sloshing, and she was lying in well fucked coma her ankles over her head and her hands cuffed to the bed frame as part of Dale's latest obsession. I was waiting eagerly for my chance to prove what a good little cum cleaner I could be and then Dale handed me a straw. "Get to work, Belle." Get...to...work...Belle...the words didn't seemed to fit right in my head. The straw felt awkward and alien in my hand. Dale had already headed into the shower, not even questioning whether or not I'd take the straw and slurp up his spooge. How could he just take that for granted? Just because I'd already done it like twenty times or so...but not with a STRAW! I don't know why, but that just made the whole thing seem ridiculous.

Still...I probably would have done it anyway if Isabella hadn't picked that time to ask, "Well what are you waiting for, you little idiot? I can't clean myself if I'm handcuffed to the bed, can I?" There she was, the sissy of my dreams and nightmares, the one that had laid me low and kicked dirt on me, the one I wanted to love me more than anything and I hated almost as much as I hated myself, and she couldn't even imagine a scenario in which I would strike back at her. Not even when she was completely helpless...then again, I think I was more surprised than she was when I started fumbling with my belt to get my pants down. "Wha-what the fuck do you think you're doing? You don't have the balls to fuck me, you little shit!" My gut knit into a tight ball of sick fury...

I saw her face go from a rage to shock and then twist into a scream of agony. I didn't know what was happening until I heard the hard 'thwacks' over her scream and felt the impact run up my arm. I looked down to see myself raining down blows with my belt along her fair skin. Terrible red welts crisscrossed over her thighs and up her smooth stomach and heaving breasts. I felt a wet warmth swallow my prick, massaging it, milking it as one hateful shudder after another ran through me. The knot in my guts grew tighter causing stabbing pains that only seemed to fuel my frenzy. I knew I had to stop...but the only way I could stop was if I finished. I saw the haze of dick doped submission drift over her eyes and for a second I let myself believe that this is what she wanted, that somehow in my mindless madness, I had found a way to win her back, to get her to look at me the way she looked at my step-family. I began screaming a garbled mess of words, a junkyard of hate clattering out of me, "CUM FOR ME, YOU CUM SLUT, CUM! FUCKING FUCK YOU! I WILL FUCK YOU, YOU FUCK! CUM CUM FUCKING CUM!" until I was just screaming "CUM!" over and over. 

When she finally did it cum, it shot out hard enough to hit my chin, and my cock vomited its filth inside her. There was no joy in it...the my guts twisted inside out and my whole body burned with the hateful bile seething in my veins. I saw something I'd never noticed in her eyes before. Something I'd missed in the haze, something I could only see from this angle...pure, unadulterated hatred. She hated my step- father and his foul spawn, not despite the helpless lust they inspired in her...but because of it. Now she hated me too, and as I saw my reflection in her eyes, I did too. 

"Please...I...I didn't mean...I'm sorry...please...please...I'm sorry...I'm suh suh..." I broke down sobbing as I begged her forgiveness, but I could tell she couldn't even hear me. I felt Dale's arms pulling me off of her, shaking me, trying to get me to snap out of it. I tried to calm down, tried to explain what had happened, tried to do anything but let out hoarse screaming cries of useless remorse. Dale was beside himself, throwing a tantrum and on the verge of tears himself, not prepared for a situation he couldn't threaten his way out of. Even through the veil of tears, I could see what a fool I'd been. I was right when I called him a boy, and I'd let a boy reduce me to this. I began to calm down, and I was just about to explain myself when I heard the voice.

"I can't tell you how disappointed I am in you. Within two months you're having a threesome with your step-brother...and I don't even want to know who's semen is dripping off your chin." my step-father stood in the doorway, filling the frame with his towering physique, his hard, handsome features betrayed no signs of mercy, if there were any to be found in the first place. He looked like a vengeful god, and at that moment, it only seemed appropriate that I would be cast into Hell. Then flashes of my tour in the basement came to me, and I remembered what Hell really was, and I didn't have the courage to accept my just desserts. 

I began to stammer out a defense, "nuh nuh No! You don't understand. This isn't...well yes it is, but it's not what it looks like. I didn't let her...I mean I didn't suck or...see I fucked it out of her." My words tripped over themselves as they raced out of me, but I began to see a small glimmer of hope. I really had just fucked her, and it's not like Dale would admit what was really going on, not if he would have to admit to flaunting his father's rules these past two months. I know it seemed implausible. I knew it was true and it still sounded like bullshit. But if I stuck to my story long enough, he would have to believe me. 

"Hmm...that's certainly one possible explanation. And I pride myself on my fairness, so I wouldn't want to condemn you to a life of sissy slavery if there were any doubts. So if you can clear up just one minor detail for me, I'll be on my way." I heaved a sigh of relief, "Why are you wearing a pair of cum stained panties?" My jaw went slack...I was still wearing panties! I had gotten so used to wearing them that I didn't even notice I had them on, but my step-father obviously did, and now there was no explanation on earth that was going to save me. I felt the walls closing in on me, I couldn't breathe, the floor rushed up to meet me and everything went black...

Things can always get worse. 



Young Master Ch. 05



I was running through the mansion, being chased by something so horrifying that I didn't dare to turn around and see what it was. I tried to find my room, but the once familiar hallways were now disjointed and strange, as if the building had be rearranged and some pieces had been replaced with imitations that had a sinisterly artificial look to them. My pursuer was getting close, its hot, rancid breath scalding the back of my neck. I kept running, even though I knew I'd never escape. Even a second spared from its horrible embrace would be worth the hopeless attempts to escape. Suddenly, out of the corner of my eye, I saw a soft shadow dart into a far hallway...somehow, I just knew it belonged to a friend. For a moment, I dared to believe their might be an escape, or at least a place I could rest for a moment and delay my inevitable damnation. I turned down the hall, almost falling as the tile became slippery, some thick, milky liquid coating the floor. I just kept running, knowing each step would be my last and still taking it anyway, constantly proving myself wrong for just a moment longer. And then I hit my dead end...at the end of the hallway...something worse than whatever was chasing me... a mirror...

I was beautiful...heart breakingly, soul crushingly beautiful. My features had grown even softer from my cherubic chin to my button nose; my lashes longer, fanning my cum hither sea blue eyes; my lips plumper and shinier, open and panting at the sight of the vision before me. My hair was falling about my face, flaxen curls of spun gold, with a lacy cap keeping it somewhat in order. My breasts were flush as they rose and fell in my panicked arousal the red set off alluringly by my pale, creamy cleavage. The french maid outfit was even more fetching now that I had the figure to fill it. I felt my stockings rub against one another as the sight of my shapely legs barely covered by my short, ruffled skirt, made me squirm and shiver. I reached out to touch my reflection, tentative and fearful...but my reflection wasn't so timid, she reached back and pulled me in, screaming as I fell deep into the darkness...into the basement...

I was completely surrounded by darkness, a void I had a terrible premonition was far from empty. I was too terrified to even run, after all, where was there to go? All I could do was stand paralyzed, petrified as I awaited whatever horror would reach out of the abyss to claim me as its own. I almost welcomed it at this point, at least then I'd know things couldn't get any worse. But there was still that lingering doubt that they just might get worse than even I could imagine...so I prayed for an end and prayed for one more second, my thoughts chasing each other down the drain. And then I saw it...faint and ghost-like, the smallest glimmer of light. I was sure I was imagining it, my mind inventing phantoms to keep me company, but I also knew I didn't care. I ran for the light, getting closer and closer and feeling a welcoming warmth as I saw it take on a woman's shape. When I finally reached it, Isabella was standing before me, shining in the darkness like an anger come to deliver me from damnation. 

She took me in her arms, her skin so soft against my cheek. I felt safe with her. It didn't matter that I was in the darkness with no sight of an exit, it didn't matter that I would never be a man again. All that mattered was she was lifting my mouth to hers, thrusting her soft tongue into mine, claiming me as her own with a kiss. A long, loving kiss...so wet...even after she finally broke our lip's embrace, I felt the wetness...warm, sticky wetness...I looked at her full lips as they curved into a haughty smile...I saw something shine from inside...something sharp...she opened her mouth and razor blades fell out by the handful. I opened my mouth to scream, but all that came out was a gush of hot blood...I crumpled to the ground as her maliciously mirthful laughter filled the void, flames bursting from the ground to illuminate the twisted architecture of Hell. I crawled back from her still, squirming on the floor, desperate to get just a little further away from her razor blade smile and predatory laugh. That's when I felt the breath again...hot rancid...and hovering right over me...the monster lunged for me...and I could scream again...

"AAAAAAAAAAAAAAAAIIEEEEEE!"

"Good, you're awake. Now we can get on with the ceremony." I open my eyes and see my step-father cutting an even more imposing figure than usual in a shiny black rubber robe, the cowl casting a shadow over his strong brow but not dimming his burning eyes one bit. The light fell on his powerful, chiseled jaw cocked up as usual, but his seductively sadistic smile replaced by a tight lipped grimace. Isabella was draped at his feet, content as a kitten, completely nude...my collar was nowhere to be seen. I had lost her completely, I couldn't even claim the lie of ownership anymore. 

My eyes darted across the room, hoping I'd see something...anything that would give me a glimmer of hope in this abyss of despair. But all I saw were two more hooded figures, my step-brother Dirk smiling broadly as he licked his sensual lips, and Darius staring with a hunger I'd never see before, his sharp features twisted into a razor-sharp smile. I tried to place the room, a hardwood floor of dark teak, red velvet drapes surrounded the large circular room, empty save for us. I tried to see an exit, but everything was covered, the whole effect was dizzying and disorienting. I couldn't place this room in my head, I could have sworn we didn't have a room like this anywhere in the mansion...and then it hit me...I was in the basement!

I clutched my chest instinctively, and let out a tiny yelp...I was wearing the french maid outfit! I didn't fill it out nearly as well as in my nightmare, but I had no doubt that I was all but unrecognizable as a man...I looked like a petite, poorly developed young woman...or more accurately, I looked like a sissy. No...I was a sissy, I just wasn't able to hide it under my clothes anymore. I couldn't help but run my hands up and down my hips, feeling the contours my corset was giving me. I was snapped out of my reverie when I noticed my outfit was rubber too...it struck me that whatever they planned was going to be very, very messy. I felt my clit twitch reflexively and felt it crush painfully against cold steel. They had caged me! I shuddered to think of what they had planned...that's when I noticed the drain in the floor, and I started begging, "Please, please, don't do this to me! I'm sorry...I tried being a man, but I'm just not cut out for it...but just because I'm a sissy doesn't mean I want to be a slave! I beg you, just let me go!"

Laughter filled the room, heavy and dark like ominous storm clouds gathering over me. My step-father's thunderous voice finally said, "You are in the wrong place if you are looking for mercy, and you are definitely asking the wrong men. Mercy is for the weak. Do we look weak to you?" It was a rhetorical question, but I still couldn't help but shake my head dumbly. There was nothing about them that was weak, and as much as it terrified me, I had to admit that it seemed fitting that they were in control. But everything was happening so fast, and I could sense a dreadful inevitability rushing towards me...one that would seal my fate forever...

"Remember, none of this was forced upon you. And from what Dale tells me, you are quite the needy little slut. Really we're doing you a favor. Out on your own you'd probably be scooped up my some diseased pimp, and you'd end up turning tricks until disease and drugs ravaged your pretty looks and you'd be left to die in a gutter. As our slave you will be well cared for. We will make you even more beautiful than you already are, educate you, teach you marketable skills, and most importantly we will protect you from your own weakness." I wanted to protest, but I knew it would be pointless. I was surrounded by men that could hurt me in ways I probably couldn't even imagine, and I could sense both Dirk and Darius were waiting for an excuse. But that wasn't the real reason I didn't argue with him. The real reason was that it all sounded so terribly true.

"Of course, I don't give a single, solitary fuck about what happens to you, but I will not allow anyone that carries my name to sully it in public. I gave you a chance to stand at my side. I gave you the opportunity to honor my name, to join the family business and experience true power for the first time in your pampered life. And what did you do? You SPIT on my name! You became a sissy's bitch, and then you tried to corrupt my youngest son, getting him to break my rules and betray my trust. At least he used a sissy properly, which is the only thing that spared him from sharing your fate. But make no mistake, blood does not protect my sons any more than your pathetic heritage stood in your way. All you had to do was prove yourself...and I suppose you did after a fashion." As insane as it sounds, I actually felt guilty as I listened to his tirade. His voice was so authoritative, it left no room for disagreement. I started thinking that maybe I did deserve to be punished. I couldn't bear to look at his accusing eyes any longer, I felt like they were burning me on the stake, so I looked at his feet instead. And that's when I saw the true source of my woes, and tried one more time to plead my case...

"But, you don't understand. Isabella tricked me! She played mind games with me, made me think she loved me to get me to lower my guard, subtly eroded my confidence and then preyed on my indecision and inexperience. She's the reason I'm like this! She made me a sissy!" I saw a satisfied smile curl up on her face and I seethed with rage. Darren reached down calmly and picked Isabella up by her throat. Even after all she'd put me through, I couldn't stop from yelping sympathetically as my step-father held my ex-sissy up by the neck, with her toes dangling precariously above the ground. 

"Is what she saying true? Did you intentionally manipulate and corrupt my step-son?" I held my breath waiting for her to answer, silently begging her to deny it, praying for forgiveness for unthinkingly tossing her to the lions. To my horror, Isabella's smile only grew wider, her face was growing splotchy and purplish as she nodded yes. I closed my eyes, not nearly brave enough to see what horrible fate would befall her..."That's a good gurl, Isabella. I knew I could count on you." He gave her a kiss that looked like it would have taken her breath away if she had any left, and then he lied her gently at his feet. She looked at me with a heartbreaking mix of haughty pride and the hazy lust of a submissive sissy.

"Look at you...you never had a clue did you? Of course Isabella was acting on my orders, she wouldn't dare defy me. I told her to test your willpower...and you failed miserably. So now, you will join the other sissies down in the basement. Now that we have the begging and blaming out of the way, we can get on with the ceremony. Are you ready to take the brand of the Harrow house?" I was utterly destroyed...all of it, every tender kiss and hard throb...it was all a game, and worse, it wasn't even her game. I was just another chore to her. And then I saw what he meant by a brand. I guess it's because I never got to see much of Isabella from behind, but I never noticed the tramp stamp she had burned into her flesh. But it was all I could see now, an ornate 'H' knotty and pulpy from where it was seared into her soft skin just above her ass. Stark panic made me brave enough to defy them.

"You can't do this to me! I'm rich! When my mother gets home she'll see to you! You hardly have any money of your own! You just have your shitty name! Well I don't want it! Not on my skin or anywhere else! I'm Byron Templeton III. You can keep your fucking name!" I was spitting by the time I was finished, out of breath and shaking. The speech had been almost too big for me, it took what little courage I had found with it, leaving me hoping that bringing up my mother's money might save me from their wrath.

"GAH HA! Listen to him, dad, he's actually proud of the name Byron. He's named after a sissy poet and he thinks he can shit on our name! Ha! You know, Belle, normally I don't grudge fuck you flat chested sissies, but personality counts for a lot, and you just made it to the top of my 'to do' list!" I cringed at every braying word of Dirk's tirade. He took a step toward me, and I felt my asshole flinch in fear, remembering how thick he felt pressed against me in the shower, and knowing he wouldn't be a gentle lover. Surprisingly, Darren stopped his advance by simply lifting his hand in the air. For a second, I allowed myself to hope that my threat had worked. But then he spoke... "Your vapid, pill popping mother isn't coming home, Belle. She'll stay doped up and dreaming her life away at the asylum for as long as I use 'her' money to pay the doctors exorbitant fees." I realized with a sob that I hadn't worried about my mother once since she was sent off to get treated for 'exhaustion'. I wondered if that meant I was a terrible son or she was a terrible mother...probably a little of both. But I was far too scared to process any guilt at that moment, especially when my step-father continued, "Your mother named me the executor of her affairs, so I control all of the money. Since you are penniless now, I can do anything I want to you, that's the privilege of power. And if you are hoping for an inheritance to come along and save you someday, think again. You will sign away all legal claim to your mother's estate before I allow you the honor of joining our stable."

The tiniest glimmer of hope lit a long path ahead of me, one of suffering, servitude, and shame, but one that ended in freedom and splendor. I couldn't sign my rights away...it was my only hope to ever escape their clutches..."You can't make me sign anything. Someday I'll get my share of the inheritance and then we'll see how easy it is to keep me locked up." I felt the strength return to my legs and I did something I never in a million years imagined I would have done...I stood up to my step-father. Sure, I was a little unsteady on the high heels I was apparently locked into, but I was on my feet, tottering right over to him and looking him square in the eye. I could swear I saw a hint of admiration in there just before he laid me flat with backhand I could only register as a blur, a thunderclap, and an explosion of pain that knocked me to the ground.

"Father, I'm getting bored. Let me break her so we can get on with this. I'll have her begging to sign in her blood withing five minutes flat." Darius' tone was cold and dead. But his threats didn't have the intended effect...if I surrendered, I'd be at his mercy for the rest of my life. If I resisted, one day I would be free from his sadistic embrace, and from what I'd seen of his handiwork, he would torture me for fun even if I never defied him. 

"Not yet. Remember, son, there are rules to this game. We go from youngest to oldest which means Dirk gets first shot at getting our stubborn little sissy to see the light." It says a lot about how completely fucked my situation was that getting hate fucked by a gorilla was a relief compared to the alternative...and that was only a temporary 'reprieve'. He made his way over to me and opened his robe, revealing his hard, naked flesh. His cock was even more fearsome than I had imagined it...and I had spent a lot more time picturing it my head than I cared to admit. It was almost as long as his father's...at least ten inches long...but much thicker...it was a fucking bludgeon...so thick I couldn't even put my hand around it. I realized with a whimper that I had my hand on his cock before he even asked...

"Now I've got to be honest, I'm not a very creative guy. I leave that kind of stuff to my older brother and my dad. But with a cock like this, who needs imagination? So here's the deal, and its going to be the best one you get all night. You sign the papers like a good little slave and I'll unlock your chastity cage. If you don't, I won't even use your spit for lube." My body didn't seem to appreciate the gravity of the situation. I was drooling for a chance to lube his cock, wondering if I could fit him in my mouth. My soft sex tried to grow hard, but only crushed against the unyielding bars of its cage. 

I squirmed as my body begged me to beg him to let me sign, to feel his hands sliding over my rubber encased body, to taste him throbbing in my throat, to have him inside me, slooooowly and gently as he pushed my boi pussy to new limits. All I had to give him was everything...and at the moment it sounded like a bargain. But then I thought better of it...the single sane sliver of my mind that hadn't been paralyzed with lust or terror telling me I had to hold on for as long as it took. For once in my life, I had to be strong. "I...I...I won't sign. Do your wuh wuh worst." 

"Oh no, little sissy..." He pulled my head up painfully as he leaned down into a kiss, crushing my soft lips against my teeth as sucked on my mouth. "I'm going to do my best." He thrust his tongue inside me without warning, it was thick and insistent, almost making me gag as it plunged down my throat. There was nothing loving about his kiss, but there was nothing sadistic about it either. It wasn't that he was trying to hurt me, after all, he could have broken me into pieces with his bare hands if he wanted to do. He just didn't care what happened to me as long as his ravenous appetites were sated. I trembled to think what he would do to my tender little hole if he was this rough with just his tongue. He dropped me to the floor, panting and flushed, and I knew I wouldn't have to wait long to find out. 

I felt his thick fingers dig into the soft yielding flesh of my buttocks, I whimpered as he effortlessly pulled me to my knees and casually flipped my skirt up, leaving my asshole exposed and vulnerable. Despite the heart pounding panic coursing through me, my cockette was still trying desperately to get hard. It seemed no matter how often the metal bit into my tender flesh, it wouldn't take the hint. I bit my lower lip and said a silent prayer to anyone that would listen...I felt his fat cockhead press against my rosebud, trying to force it to bloom. I felt his muscles kiss my skin as he draped over me, whispering, "Hey, Belle, I just wanted to say thanks for not signing the papers before I got a chance to fuck you raw." 

"AIEEEEEEEEEEEEEEEEEEEEEE!" He forced his gigantic helmet through my taut ring, every millisecond seemed more impossible than the last. It felt like giving birth in reverse...like being impaled on a burning log...like a fat cock stretching out my asshole without the mercy of lube. Every cell inside me screamed in agony. He was slowly deforming my body, stretching it past a point the human body was ever intended to go. It was surreal...it didn't feel like flesh...flesh doesn't burn like hot coals or cut like jagged glass. Every time I thought he couldn't possibly go any longer, more fresh agony would force its way further inside me. I closed my eyes, and told myself over and over again that it was almost over...almost over...almost over...

"Well the head's in...that wasn't so bad, now was it?" Dirk's hand came crashing down on my ass, sending a shock-wave of pain that reverberated with the agony inside me, screeching a duet like some lullaby for demons. If he noticed, he didn't make any mention of it...he just kept driving his monster deeper inside me, devouring me from the inside with every impossible inch. His fingers gripped my hips, pulling me back towards him as his freight train carrying an overload cargo of heated Hell kept rolling along. I couldn't breathe to beg him to stop, couldn't think to consider signing my soul away to save my life, couldn't do anything but process pain so profound it would confound a poet. And he just kept coming...




Young Master Ch. 05



"Fuuuuuuck...this is soooooo fucking tight! Shit...I'm not even sure you can take my full length, but it is going to be a blast finding out." Dirk was a true monster, and not just because of his ogre cock and gorilla hands...he had a satyr's soul. He wasn't even trying to get me to surrender at this point. If he was, he would have pulled out so that I could beg him not to stick his pet lamprey back in me, or at least stop to let me catch my breath. If he had...I don't know...but its hard to imagine willingly agreeing to let him continue if I had the capacity for choice at the moment. And he wasn't doing it to torture me...as inhumanly intense as it was, he wasn't going out of his way to hurt me. Even spanking me was just a show of ownership, and possibly even affection. He was a monster because my living Hell wasn't even a consideration for him...it never even crossed his mind. Once his dick was hard, he was going to find something to fuck. He was a simple beast...the world was just a wonderful collection of holes to him...and asking whether a hole wanted to be filled was far too philosophical a question for him to ponder.

"Damn...all the way in. I should get a t-shirt made for you sissies that manage to fit my full length. Something like 'I got stabbed by the Dirk and lived to tell about it'...then again, maybe we should wait and see on that part..." I took a deep breath to prove to myself I wasn't dead yet. He was inside me...and I wasn't dead yet. I allowed myself to hope that maybe the worst was over. As he pulled out slowly, he raised my hopes even further, the pain lingered like a ghost's cock behind him, but it was ethereal, insubstantial compared to the unreal reality of his flesh. When he was all the way out, I let out a sigh as long as his prick, proving I could exhale as well. I could breathe again, and that told me I had survived. And when he shoved a fourth of his cock back into me in one thrust, and then kept hammering away a few invasive inches at a time...I learned I could scream again as well...

"AaaaAAaAAaAAAAAAiiiIIIIIEeeeEEeeeEEEEEE!" his cruel cock forced out what little air I had left in a scream so large I was amazed it fit in me in the first place. The pain had been slow and constant before, but at least it had been predictable, getting progressively worse the more he warped my tenderest tissue. This was like being gored by a wild boar from the inside. Savage, unpredictable attacks that left me panicked and waiting for the next strike, forever guessing wrong and paying with my ass. 

He began to pull out, and I dared to take another breath again, then just as reached the half way point, he changed course and slammed his weapon inside me all the way to the hilt. "EEEEEEEEEEEEEEEEEEEEE" a birdlike wail flew out of me, free from the torture chamber housed inside my skin. I envied it...I was stuck inside my treacherous flesh, cursed with a body that seemed to feel everything a little too much...skin that surrendered to pleasure a little too easily, and felt the sting of the inevitable punishment even more keenly. I tried to think through the pain, but it was like there were shards of glass cutting into my brain, making my thoughts alien and disjointed. Things like...I wonder if Dirk will get grounded if he fucks me to death...if I had Dirk's body, would I be fucking a sissy in the ass right now...God, I hope they don't put 'fucked to death' on my tombstone...is this really worth my inheritance...or maybe I'd just be a really ugly sissy...how much does a new asshole cost, anyway...it went on and on like that as Dirk continued pounding me at an erratic pace.

But pain is a strange beast, it can tear out your guts from the inside one moment and began playfully nibbling the next. I don't know if its because my asshole finally stretched wide enough to take his strange beast, or if my blood was acting as some sort of primitive lube, or maybe my brain finally said 'fuck it, I'm not processing this shit anymore. If you want to get fucked by a rhino horn or whatever it is, that's your business.', but whatever the reason, the pain lessened to the point that it felt like pleasure compared to what came before. The adrenaline and endorphins flooding my body probably didn't hurt either, making me feel high, doped and wired at the same time, without a shred of shame or sanity to prevent me from rolling my hips back onto his cock just so I could feel him slam them back down. I giggled and grunted as I felt his freakish manhood swell to grow impossibly thicker in response. 

"Damn...who...ungh...taught you...nngh that?" A sick thrill kissed its way up my spine sending icy-hot shivers that made me melt. Of course I hated him, there were enough scraps of me left to remember that even as I squeezed his cock with my aching asshole and winced through the reminder of how bad it could hurt.,,but hating him was what made it so hot...so forbidden...so kinky. I was a novice to surrender, but I was learning fast, and I loved to study...especially since I had just discovered the ironic sense of power in controlling how much pleasure he would receive. A slight roll of the hips, a subtle squeeze, a sudden thrust backwards, all drove him closer to the brink of oblivion, or slowed him maddeningly. Sure he, could have held me down and pounded away at me and there would have been nothing I could do to stop him. He could make me into a weak, whimpering hole, but if wanted more pleasure than he could drill out of me, he would have to let me work my magic. 

"Fuck...that's it...GGRAAAGH...you earned it!" Dirk's savage roar shook the room, traveling down his mountain of a body like an avalanche, gaining momentum until I exploded out of his cock, practically punching me with a torrent of his man mead. Thankfully, his scream drowned out my own, as every muscle in my body seized up and sucked out every last drop of his cum. Maybe it was some sort of instinctive attempt to put out the fire still blazing in my abused ass. Maybe I was responding vicariously to his pleasure as I always seemed to do, my body recognizing a superior animal's right to pleasure and rejoicing that I brought it about. But most likely, it was just the chemical waste my brain was shitting throughout my body after suffering through the sustained brutality of Dirk's love making.

Whatever it was, if faded as soon as it came, leaving me to feel the cool air hitting my inflamed guts as my asshole gaped lewdly. I felt paradoxically empty and full the same time...my boi pussy ruined, maybe forever stretched wide and hungry, while at the same time, the outline of his cock lingered in the form of every throbbing nerve in my ass crying out in pain. It was a dull, stabbing throb, a hurt that had faded, but refused to leave my side...like a possessive lover wanting to hold me close as long as he could. Still it wasn't half as bad as the throbbing ache pushing insistently against my chastity cage, confused and betrayed that it hadn't gotten to cum after such a rough fuck. Maybe if he had pounded my prostate a little bit longer...but I pushed thoughts like that out of my head, not wanting to want the man that was trying to enslave me. Instead I gathered tiny shreds of my willpower of the floor and looking up at Dirk asked, "Do you surrender now?"

I cringed as his hand raised high in the air, ready to strike me down..."DIRK DANIEL HARROW! You will not lay a hand on her. You have cum, and thus your turn is ended. Now calm down and control yourself. Let's see if Darius fares any better." Relief turned to horror as Darius made his way over to me. If Dirk was a monster out of carelessness, Darius was one out of dedication. All I had to do was look at the scars on his sissy's skin between the ink and piercings to know what kind of man he was. Every step he took brought me one step closer to the gallows. I held my breath and closed my eyes, stupidly acting as if it would make a difference, as if I'd open my eyes and see anything but Darius' sadistic smile. 

"Aww, look at you, you're shaking like a leaf. Don't worry, my beautiful Belle, I'm not going to hurt you. Hurt you? Heh...you should be so lucky..." He took my head in his hands and lifted me into a kiss, softer than I expected, our lips merely grazing one another. I didn't know what to do with a kiss like that. Even when Isabella was playing at being romantic, her kisses were powerful, passionate. I kept expecting him to take advantage of my confusion my forcing his tongue down my throat, but to my surprise, he just kept gently pressing his lips to mine, never opening his mouth or more importantly, mine. His fingertips stroked my cheek and I started to squirm in his arms. He held me close, but allowed me to writhe in perplexed frustration, never gripping me to tightly or taking advantage of the obvious strength housed in his taut muscles. In a moment of weakness, I found myself sucking on his lips, trying to part them with my tongue, trying to coax out a real kiss from him, the kind that hurt. I just wanted things to make sense again...

"Now, now, Belle, this is supposed to be torture, remember? So I can't have you acting on those nasty little urges of yours. You will behave yourself and meekly accept whatever I do to you or there will be consequences." His tone was gentle, but in a practiced, artificial way that was even more terrifying than his usual serial-killer cold affect. He held my head firmly as he held me with his lips hovering over mine, but he didn't hurt me in the slightest. My imagination ran wild, I was on the verge of tears just from trying to picture what agonizing abomination he would perform if I didn't obey. I knew that was exactly what he wanted, to twist my fear inside me like a knife and let me torture myself, all while being gentle as a lamb...but knowing his game and being able to prevent it from working on me were two very different things...

"puh puh Please duh duh don't huh huh hurt me." I immediately regretted pleading for mercy, giving him that much more power over me. He paid no attention to it, mercy being a concept as alien to him as fire is to a fish. Instead, he pulled me into his lap and pulled my top down over my shoulder, and began covering my exposed flesh with tender, teasing kisses...my skin sizzled and I felt myself melting into his lap despite myself. I couldn't control my body, this was everything it wanted, to be controlled and helpless and loved...all at once. And it was too stupid to know it was all a sick game. I rubbed my ass against his lap feeling his impressive hardness against my soft skin, I imagined how tender he would feel inside me...and my cage closed in around my swelling flesh, sending a spasm of pain from my groin to my gut, where it stewed and festered. Now I knew his plan...to kill me with kindness. "I know what you're trying to do, Darius, and it woOoOooOOOOOHH!"

"Sorry, you trailed off there at the end. Something about this not working?" I'm putty in his hands as he toys with erogenous zones I never knew I had. He was rubbing slow circles around my nipples, running his tongue along the outside of my ear and darting in and out like a thief, and lightly nibbling on my neck, my pulse pounding so hard he could probably taste it. By the time he peeled off my leather dress and left me naked save for my maid's cap, stockings, and cockette cage, I was a whimpering mess. I didn't know how long I could take it. Every sweet caress was followed by the increasingly brutal bite of cold steel. And if I understood the fucked up rules right, he got to play with me until he came. But he showed no sign that he was going to fuck me...which meant I was fucked. And then things got worse...

"NoOOoOOOOh pleeeeeeeasssssse doOOOooOOOn't!" His fingers found there way inside my gaping hole. I wish I could say I was moaning for him to stop because it was still sore, but the stabs of pain where a welcome respite compared to what followed them. Darius proved himself an artist with his fingers, manipulating my sissy spot with a skill and dexterity that would have impressed the world's finest watchmakers or bomb defusers. He was certainly winding me up, hitting sissy spots I didn't even know I had, making my entire body an exposed nerve, every inch of flesh soaking up the slightest physical contact. My own sweat trailing down my trembling flesh like teasing fingers, his hard swimmers physique rubbing against my soft, yielding flesh...well, more like my soft yielding flesh rubbing up against his hard body, but same difference. My genitals stubbornly refused to yield to its prison. I was starting to think it had more fight in it than I did. But then I felt a familiar twinge, like a chord being struck inside me...that bubbling bliss building to an ecstatic eruption. My body leapt on the shred of hope like a feral dog lunging for a scrap of raw meat. And that's what I was at that point...raw meat. Mindlessly racing towards a goal my mind was telling me I'd never reach. Because even if I could find a way to cum with this cage on, Darius would never have given me the satisfaction. True to form, the moment before I exploded, he pulled back, defusing me with expert finesse.

"You probably think I'm cruel, don't you? It's okay, you don't have to answer, I know how you sissies whisper behind my back, how you always scurried away to avoid me in the halls. As if I was your step-boogeyman. But if you could see through my eyes right now, you'd know I am the most compassionate man you've ever had the honor of meeting." As if to 'prove' his point, he begins playing me like an instrument again, one had on my nipples, the other inside me, and his lips raining down a barrage of soft kiss along the nape of my neck. He composed a symphony of whimpers and moans as he continued to string me along and hang me out to dry. The longer he played and the more crescendos he cut off, the more the pleasure turned to pain. It got so bad I was getting nostalgic for something as sweet as a raw ravishment. I was willing to do almost anything for a little relief...but not anything.

"NNH nev uh uh Never...suh uh unh surrender. Nnh nuh not to yuh yuh yoooOOoooOOH!" Darius' plan had backfired. Sure I was so exhausted I didn't know if I would have the strength for the next moan, sure I was dying to taste ever last inch of him, sure his loving treatment had left me in a state of Purgatory I'd gladly have cut off a pound of flesh to escape, but that was his mistake. HE was the cause of it all. And all I had to do was nothing and he couldn't win. It was a daunting task, but I had a lifetime of practice at doing nothing, and I intended to use it to my advantage.

"Sigh...and now you're blaming me for your own stubbornness. Making me the villain in your dime store dreadful so you don't have to face the truth. You want to be our slave just as much as the other sissies, you just want it forced upon you so you don't have to admit it. That's why I am the kindest man you'll ever meet. I'm willing to play the heavy for you, to make you do things you would never dare admit you wanted to do, things you beg me to stop until your throat grows so hoarse you can't even whimper. And then I'll make you do things you never even knew existed, and I will make you love them. And yes, you will hate me for it, but that is a price I am willing to pay." Throughout his self-deluded tirade, Darius, continued to torment me with suffering I apparently wanted but was too afraid to admit. Funny, I just thought I hated his living guts.

I knew I had to do something. Darius was hard, but showing no hints of an impending orgasm. And as much as I hated him, I doubted I could withstand his abuse as long as he could dish it out. I didn't think, if I did, I probably would have cowered from the idea like a scared little rabbit. Instead, I reached inside the boiling pit of bile that made up my innards and pulled out a scathing onslaught, "Fuck you, you wimp! At least, Dirk had the balls to fuck me. You're so afraid I'll make you cum before I surrender that you are just fingering me like a virgin on prom night." 

Darius threw me to the ground, towering over me, his voice lost it's gentle polish and was left with the cold steely tone of a sharp knife. "I don't know which is worse, that you would insult me like that, or that you think I'm stupid enough to fall for it. I tried doing this the easy way. I thought you would appreciate the creativity of my approach. But if you want it more traditional, then so be it. I'll bring out my toys and have you begging to be our slave inside five hours." I was scared stupid for a moment. All I wanted to do was hide under a rock and never come out. But there was nowhere to hide, and Darius was reaching down for me, his hand looming larger and larger over my face until it blotted out everything else. Mindlessly, I blurted out, "I can make you cum in under five minutes! I'd bet my freedom on it!" He paused, perplexed, and for a moment, I heaved a sigh of relief...and then it hit me...I had no idea how I was going to make him cum!

"Hmm...my way is much more certain, but what's life without a little risk? Very well, the timer starts from the moment I stick my cock in your gaping cunt and you have five minutes to make me cum or you sign your fortune and freedom away?" I just sort of nodded dumbly, hoping whatever part of my brain shit out that challenge would come up with an idea on how to win it. But all I could think of is what it would feel like hanging in one of those cages in the basement. I could taste the gruel already, feel the dark close in around me...no, not the dark, Darius' arms, pulling me to my knees, spreading me wide as his cock slid inside me without the slightest resistance.

Minute one...I was surprised at the length and girth of Darius' cock, it was only a little bigger than the 'runt' of the families. Sure, it was a nice size, but nothing compared to Dirk's or his father's, and it didn't have that comely curve that Dale's did, so he couldn't hit my sweet spot nearly as hard. I was beginning to understand why he got so good with his fingers...I stifled a laugh, knowing mocking his prowess wouldn't be the best way to make him cum...

By minute two I was ready to take back everything I didn't dare say about his endowments. He wielded his rod as masterfully as he had used his fingers, churning up my abused ass and sending those familiar sparks of mind melting bliss much sooner than I was prepared for. If he kept up like this, I might actually cross that threshold I'd been denied for so long, but all thoughts of making him cum had melted into a thick drool that ran down my chin.

Minute three stretched out into infinity. Every eternal second an inch closer to paradise as I crawled up from miles down in Hell...but still, Heaven was in sight. My body knew what to do even if I did not, rolling my hips as I thrust back onto his cock...milking his manhood with my soft, tight muscles...using every technique I learned from getting Dirk off in a desperate attempt to make him cum. I felt a little throb, but I knew there was no way I'd make him cum at this rate. I could feel a leash bite into my neck. I imagined him leering down at my bloodied body...and then it hit me...

Minute four was a decisive moment, I didn't plan it, I would have never been that stupid, or that brave. But something inside me knew what Darius wanted even if the rest of me was too terrified to contemplate it. I slammed my head into the hard oak floor, sending blood gushing from my nose onto my plump, shiny lips. Darius paused, paralyzed with shock as I looked back up at him, gave him a cum hither look and smiled even as the blood dripped from my chin...and squeezed...

"NNH! Wait...NO!" Darius erupted inside me like a water balloon popping every last drop of cum bursting out of him in a shotgun blast of sticky seed. I cooed in frustrated satisfaction, knowing I would be denied release that much longer, but momentarily content with my meaningless victory. To Darius' credit, it did not take him long to regain his composure, he covered his shame in his robes, stepping back into the shadows without a word of reproach.




Young Master Ch. 05



"My my...I must say I'm impressed. I half expected you would outlast, Dirk. After all, the shock carried you through the ordeal more than anything, and Dirk's approach has always been, shall we say, direct? But to best Darius? That I did not expect. I'll have to reconsider my opinion of you...slightly. For that, you deserve a small boon. You are the only one in this room that isn't 100% certain that you will beg to be our slave. And I suspect that deep down you know you will too. So, I could walk over there and work my wonders, but that would be too easy. You've earned something a little more...poetic. So I will allow Isabella to take my turn. Isabella, you have five minutes to make her beg. If you don't...ah but why dwell on such an ugly thought?" 

My jaw dropped as Isabella slowly crawled towards me, her eyes growing hungrier as she slowly sauntered over...but there was something else in them too, something I wanted to believe was regret. But when she smiled and ran her tongue slowly across her sensuous smirk, it was hard to imagine she felt anything but pride in what she'd done to me. I steeled my defenses, ready for any of her usual tricks. I figured she'd boss me around, fuck me silly, maybe feed me all of the cum pooling in my asshole baby bird style. Whatever she did, it would all be a part of the same sick game she had played from day one. Seduce and destroy...I was wise to it, and I wasn't going to let her push me around anymore...no matter how much I craved it. All I had to do was last five minutes...

What I didn't expect...what I wasn't prepared for...what I had no defense for...was for her to wrap her smirking lips around my earlobe, whispering, "I'm so sorry, Belle. But I had no choice...I still don't. And neither do you...at least this way, we can be together..." her voice was low, and ragged, full of a hurt I had never heard from her before. It wasn't until I heard the fear in her voice, the profound hopelessness, that I realized how pointless it was to try to resist. Sure, I could last long enough to ensure that Isabella suffered for my stubbornness, but surprisingly, the thought of that only made me feel guilty. And if I could, which I wasn't so sure of, what would be the point? After they finished their little game, they wouldn't just let me go. They had the rest of my life to make me sign whatever they wanted to. I had already lost whatever game they wanted to play the moment they made the rules. Four minutes were only a formality...

I took her head in my hands, my lips tingling against hers, tears streaming down my cheeks, I begged, "Please, just give me a little longer...please pretend with me, for just a minute..." She didn't say a word, but I saw something soften in those hungry eyes of hers, and felt her hands pulling me into a kiss. Our mouths wrestled as if they were trying to swallow one another, our tongues wrapped around one another, sliding and twisting as if trying to get a good grip. She drank down my sobs and fed me moans with her slick little tongue. We fell to the floor, every limb frantically wrapping around each other as out sweat slick bodies slid against each other. We desperately clung to one another, trying to hold onto the lie for just one more second, to pretend there was still love somewhere underneath all the hurt and betrayal...to pretend it was there to begin with...but our time was running out...only three minutes to go...

I knew she didn't really love me. I knew this was just another chore for her, a way to stay in her Master's good graces. I knew that once I was down in the basement, I would be just another annoying sissy she had to keep in line. But that was okay, because the truth didn't matter in her arms. All that mattered was that I could believe in the lie just a little longer. This was the only thing I could do for her, the only way I could ever help her. And as long as I could pretend she loved me as much as I wanted to love her, it was worth any price. I pulled my mouth off hers reluctantly, crying out, "Please, let me sign!" I was pretty sure I still had two minutes, but I didn't want to risk cutting it too close.

"See boys? Never send a man to do a sissy's job. Give Belle the papers. I'll get the branding iron ready." He made his way over to one of the red velvet curtains and pulled an iron out of a brick oven cut into the wall. It glowed white and it lit his cowled face with a Hellish light. I couldn't take my eyes off it, even as Isabella handed me the papers, stroking my hair as I laid my head in her lap, signing every page she told me to. I moaned a sigh of relief as I heard the click of my cage freeing my sore sissy clit. I stroked it feverishly, hoping for a little escape even as the walls were closing in on me. My new Masters stood over me, their arrogant pricks turning their noses up at me as they delighted in my despair. Master Darren walked behind me firmly ordering, "Up on all fours, Belle. I want to make this a memorable occasion for you."

I doubted I would ever be able to forget it, no matter how hard I tried, and I buried my face in Isabella's bosom, not wanting them to see my cowardly sobbing. I was in agony imagining how much it would hurt, but instead of the hot hiss of the iron, I felt a much more welcome heat sliding in my well prepared hole. Despite Dirk's earlier abuse, I was at least well lubed with two loads of cum, and with my pathetic clit free to throb and leak all over the hard wood floors, all I cared about was feeling him hit my sweet spot as hard as he could. I flashed back to my room that first day with Isabella...watching him force his cock into her eager hole, not being able to imagine what it would feel like to be her. It turned out my imagination was woefully lacking. His experienced thrusts made Darius seem like an amateur, and his inexhaustible passion made Dirk look like a two-pump-chump. I had already given up everything I ever had or ever would have, so pretending I wasn't in love with his cock seemed like a moot point. "Yeeeeeeeeeesssss! Fuck me! Please! Fuck me harder! I'm so close...I'm so...EEEEEEEEEEEEEEEEEEEEEEEEEEEEEEEE!"

The hours of torture and teasing, the terror and torment, the hopelessness and heartbreak...all of it left me in hot sticky squirts, my body finally getting the release it had been begging for. Mindless, animal, pure, perfect pleasure...I almost felt sorry for them...they would never know such wonder, never feel every goosebump on their smooth skin become a throbbing clit, never cum so hard they went to that place no one could touch them...and stay there as long as a hard cock sawed in and out of them, breaking down the gates of Heaven with relentless pounding so I could sneak in. The voice of God spoke to me, sounding surprisingly like my new Master, "That's a good gurl. You're going to be so beautiful when the surgeons finish with you. You've had a fine head start, but wait until we give you the body to match your slutty soul. You'll see, you'll learn to love being a slave. Your kind always does..."

Who was I to argue with God? Especially while he was fucking me? I looked up and saw an angel smiling down on me and I knew I'd made the right decision. I was in Heaven...and then I felt the brand. At first I thought they made a mistake. It was ice cold...how was it supposed to burn their mark into my flesh? It seared my nerves on contact, making the initial heat too powerful to process, but luckily, there was so much more pain that followed, so I wouldn't be confused. I was cast into Hell, paying for the only sin in my step-father's eyes...weakness. I was damned, screaming up into the face of a succubus as she looked down at me with hollow eyes. Then again, maybe there was something in them, I hoped I was wrong, that it was just the pain blurring my vision...making everything go fuzzy and dark until I fell into a void even darker and more desolate than in my nightmare...

I was disappearing...being murdered, the last of my manhood and will burned alive and screaming. Byron was dying, and what little mind I had left was telling me that whenever I opened my eyes next, it would be as Belle. I would no longer be the Young Master...

I would be the Young Sissy...