The Young Master

The Young Master Chapter 1 Transgender/Authoratarian Smitty Simon (www.smittylmsimon@gmail.com)

This is a work of fiction, any and all resemblances to people living or dead are purely coincidental. The author, Smitty Simon is the creator and sole owner of this content and any reproduction of this material either in whole or in part must first be approved by him.

All characters in this story are aged 18 or above.

On a personal note, this is my first text only story. I generally make illustrated stories, photo comics, and caps with a TG theme at http://smittysimon.blogspot.com/ If you have any suggestions or comments, feel free to send them to my email posted above.

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 cantalopes 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 supressing 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 authorative, 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 cockhead. 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 intoxicatingly sweet perfume, making me dizzy and hungry and horny..."It's not a puppy, so don't just cuddle with it. Suck it!"

"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 strecthed 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...

"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 electricty 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...