tagTranssexuals & CrossdressersYoung Master Ch. 01

Young Master Ch. 01

bysmittysimon©

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!"

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