Young Master Ch. 01

"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 stretched 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...