tagTranssexuals & CrossdressersYoung Master Ch. 04

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!"

Report Story

bysmittysimon© 6 comments/ 35957 views/ 15 favorites

Share the love

Report a Bug

3 Pages:123

Forgot your password?

Please wait

Change picture

Your current user avatar, all sizes:

Default size User Picture  Medium size User Picture  Small size User Picture  Tiny size User Picture

You have a new user avatar waiting for moderation.

Select new user avatar: