Category: Transsexuals & Crossdressers Stories

Young Master Ch. 04

by smittysimon©

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

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

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

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

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

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

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

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

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

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

...

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

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

...

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

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

...

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

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

...

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

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

...

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

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

...

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

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

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

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

...

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

...

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

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

Category: Transsexuals & Crossdressers Stories