tagTranssexuals & CrossdressersYoung Master Ch. 05

Young Master Ch. 05

bysmittysimon©

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...

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