tagTranssexuals & CrossdressersYoung Master Ch. 03

Young Master Ch. 03


"That's a good little, sissy. I told you that you could take the whole thing." I feel a sense of ashamed accomplishment as her smooth balls rest on my chin and I smell her intoxicating mix of pomegranate and a hint of musk as my nose crushes into her flawless, taut torso. This was the last time. It had to be. We couldn't keep sneaking around waiting for a chance for a furtive fuck or speedy suck. And if I got caught...no, I didn't even want to imagine what it would be like to be stuck in that sissy hell down in the basement. At least not until after I came inside her pretty lace panties...and then never again...

Of course, I had promised myself that before. The first time was when my step-father left me alone with her in an eerily quiet basement after giving me a guided tour of Hell. His words still rang in my ears even as she whispered dirty nothings inside them. It all whirled together, "Get caught sucking or getting fucked one more time, and you'll end up another sissy in my harem...so we better not get caught. One more time...suck and fuck...one more time..." I relented, the fear and tension of the day breaking down my resolve, making me desperate for the escape of pure animal lust. She pulled my pants down and pinned me to the wall, my ass still well lubed with her earlier deposit. Then she fucked me hard against the wall, each thrust squishing my little cock against the even harder brick squeezing the cum out of it like a roll of toothpaste, my girly moans echoing throughout the halls even as my orgasm echoed inside me, bouncing back and forth as she continued to pound my ass, more concerned with her own release than with my dick dumb drooling state of cock induced catatonia. When she finally erupted in my ass, I felt like I had burst free from that terrifying underworld and exploded into the heavens.

When I came down, she was sucking the last remnants of her cum from my ass even as I sobbed shamefully. "Don't worry your pretty little head about it, Master. I'm just getting rid of the evidence." I blushed as I saw my cum staining the pure white walls, and realized I had to get rid of some evidence of my own, licking them clean with a piggish grunt. I knew I shouldn't have, but I told myself since it was going to be the last time, I might as well enjoy it. So when Isabella told me to open my mouth and fed me the rest of her cum baby bird style before thrusting her tongue inside my mouth and painting my lips, tongue, and the back of my throat with it, I just cooed...But after I pulled myself together and silently followed Isabella back upstairs where I belonged, I swore to myself that I would never do that ever again...

I felt better once I got out of the basement. I was sure I never would have let her take advantage of me like that if I wasn't so nervous and out of sorts. I decided I would bring Isabella back up to my room and fuck the shit out of her. I had an extra spring in my step as I led her back up to my room and closed the door behind us. It felt a little strange not being able to lock it since my step-father busted it, but in a strange way, it kind of bolstered my spirits imagining that someone might walk in on me fucking her this time. I even managed a little sneer when I told her to strip for me, remembering the cocky little bastard I used to be before my step-father moved in and made me feel like a weak little boy.

When she was completely naked, I marveled at her beauty, as if seeing her again for the first time. She looked so different when I wasn't staring up at her, and mischievous smirk or no, I knew I could put her in her place. I told her to get on her knees and suck my cock, and she giggled a little as she lunged for it. She was treating it like a kinky little game, but I told myself it was one I would win. All I had to do was bust a nut in her face and then one in her ass and I'd restore the natural order...of course, I would have had been able to get an erection for that to work.

It was so frustrating to feel her lips on my soft skin, to shudder at their touch, but to feel nothing stirring down below. I blamed it on nerves, on exhaustion, on having cum more in one day than I ever had before...on her. That emasculating little giggle, sure it was her fault. Even now I can see that. Just another one of her games. I told myself that he who laughs last, lasts best and decided to turn in early, telling her that she'd better wake me with a blow-job if she knew what was good for her. It didn't take long for me to slip into a troubled fitful sleep, populated by nightmarish visions of life in the basement. The last coherent thought I had before tumbling into unconsciousness was that next week would be different...


Just before waking, I had a more pleasant dream than the nightmares of sissy slavery, but in a way, it was much more frightening. In it, I was giving Isabella a long, loving blow-job, more making out with the cock than anything, and I felt safe and free. Somehow I knew no one would find out about it, and somehow I knew there was nothing wrong with enjoying it. It felt so real...I could taste her on my tongue, feel her cock-head kiss my lips sending sparks all across my body, I could even breathe in her smell, making me too dizzy to care about the greater symbolism of sucking off my sissy in a dream. I'm sure Freud would say it represented unresolved feelings of abandonment, but sometimes a sissy cock is just a sissy cock. It was all so real...by the time I realized it wasn't a dream, I could feel her ready to explode inside my mouth, so I figured what the fuck, why stop short of the finish line.

I felt the bottom of her cock throb against my tongue and I knew what was cumming. Worse still...I wanted it...needed it even. In that single moment I needed it more than my dignity, my manhood, or my freedom. I felt a wet burst inside my mouth as she unleashed a full load into my ravenous maw. I felt it tingling on my tongue, the taste again reminding me of some half remembered exotic delicacy, not a cheese, no maybe morels? I wanted to savor it on my tongue, but my mouth was filling up too fast to hold it all. I tried to swallow it all as quickly as I could, but there was too much and it began to drool down my chin. Before I could even whimper in lustful shame, Isabella was lapping it up and feeding it back to me with her soft, sensuous tongue. I sucked her tongue clean only to feel more cum running down my cheeks. Now I had plenty of time to whimper...and moan...and pant breathlessly as she slid her tongue across my flushed face and shared her cum with me until I was all clean, but feeling dirtier than ever.

When she finally rolled off of me, I was left reeling. It was a good thing I was already in bed, because after that, I probably would have collapsed anyway. I still couldn't fathom how her cum could make me feel so good. Some kind of strange chemical reaction was occurring, but I didn't know if it was her cum or my brain that was to blame. It caused the strangest mix of drunken alertness. It was more exhilarating than a hot cup of coffee followed by a shot of brandy, making me feel light and frisky and filled with mindless giddy glee.

But it was a double edged sword, as the alertness brought a rush of self recriminations with it, and the dick dazed haze leaving me unable to put together the pieces of my shattered psyche. My mind was like a dog chasing its tail, racing in circles, snapping at itself, feeling more frustrated and confused with each passing moment. I went from high to low in a few breaths and I was beginning to understand that if her cock was a drug, then the cum down would be a bitch. And to make things worse, I had to change underwear. Sucking her cock had made me cum again, and I was so lost in the dreamy moment, I hadn't even noticed it. But Isabella sure did, "Aww, you came for me again. That is so cuuuuute. I thought this might happen, so I sneaked out while you were sleeping last night...oh and by the way, I loooooove that you still suck your thumb...and just look what I got for you!"

She held up a pair of ivory colored silk panties, with a cute little boy-cut design. She looked at me expectantly, as if I was supposed to eagerly snatch them out of her hand and put them on with a sissy squeal of delight. I guess I couldn't blame her for thinking that, but that only pissed me off more. "Let's get something straight, Isabella. I am a man. And I am your Master. So you need to start treating me like it." I tried to keep my voice steady and my eyes cold and hard. Even I was a little impressed with how hard I sounded...

"You've got a little..." she wipes a bit of cum she must have missed with her tongue and sucks her finger clean. I blush and shrink into myself, just hoping she'll leave me be, but I'm not that lucky. She began nibbling on my neck and teasing my nipples. This was an awful time to find out I have sensitive nipples and that when someone sucks on my neck it makes me moan involuntarily. "Pleassssse. Master? I only want to make you happy. And I know wearing my panties all day will make you happy. I felt so bad for you last night when you...well, you know...So I thought if you wore these all day, you'd be so frustrated and pent up by bedtime that you could fuck me for hours. You know, really put me in my place..." She punctuated her little speech my taking one of my nipples in her mouth and sucking on it hard, rapidly flicking her tongue across it like it was the head of my cock...

Deep down I knew she was toying with me, I mean, she wasn't even being clever about it. I think that's why I agreed to put on her panties again, I wanted to beat her at her own game. I wanted to wear them all day, and instead of begging her to fuck me at the end of the night like she expected, I'd have her begging me to fuck her. And besides, they were boy shorts, so they were almost men's underwear.

I told her that I needed some "me time" but gave her permission to roam the estate. I just couldn't imagine sending her down to the basement after I'd seen what it was really like, but I knew that if I let her follow me around all day, she'd find someway to get me in trouble. I felt a little more at ease when I saw her walk away, and boy, I could watch her walk away for hours. But it didn't take long for me to realize she already had gotten me in trouble. I was kicking myself for letting her talk me into wearing her panties. Every step was a maddening caress to my tightly hugged cock. I felt conspicuous and was sure someone could see the outline of her panties under my slacks. It was bad enough wondering who knew about my little sissy snafu, now I had to worry that they knew I was still on her hook. And what if my step-father found out?! I'd be back down in the basement, but this time to stay...

Luckily my step-brothers greeted me with their usual contemptuous indifference. I know they would never let me hear the end of it if they knew the truth, so Darren must have been good to his word and kept my sissy secret. That made me want to prove myself even more. If I could just find a way to tame Isabella, it would be like this shameful saga never took place. I took a deep breath and then made another solemn vow to walk the straight and narrow path to manhood...and then I took my first step and a silky swish almost made me double me over as a result of frustrated friction.

I managed to make it until noon with out losing my cool, although I'm not sure if cold sweats count as keeping my cool, but I guess it does on a technicality at least. That's when I saw Bambi, skipping along without a care in the world...and I mean literally skipping. Who even skips anymore? I realized I could make up for my poor choice in my pet sissy then and there. She might not have been my personal property, but as a house sissy, any Master could take her anytime he wanted. And I wanted...I wanted very badly. I followed her out to the garden, where she was actually smelling flowers and swooning. I'd never seen anything so girly in all my life. But my attention soon turned to her more mature attributes, the way her short baby blue party dress lifted up as she bent all the way from the waist to stop and smell the roses. Her white ruffled stockings drew my eyes up to her ruffled rumba shorts. I was a little proud of myself that instead of wondering what they would look like on me, I wondered what the cute little rosebud hiding between her cheeks smelled like.

I made my over to her with an exaggerated swagger, psyching myself up before taking one of her perfectly plump ass cheeks in hand and squeezing it. She jumped up with the most adorable little yelp, and I caught her in my arms, her blond curls caressing my cheek as I whispered in my ear, "Are you ready to get stud fucked, Bambi?" I felt my cock hard between her cheeks, and I was even able to ignore the fact that it was straining against silk to do so. My breath was hot and ragged, a predator's grin cut across my face. I had never felt this dominant, this powerful...and then she burst out laughing...

"I'm sorry...tee hee...really I am...I'll hee...I'll stop....I snnrt snicker...I can't EEE HEE HEE HEEEEE!" She doubled over in peels of a laughter and I let her drop to the ground writhing as loud cackling screams tore through her tiny frame. Just when it looked like she might stop, taking deep panting breaths and dropping to a low titter, she looked back up at my perplexed frown and burst out laughing all over again. "hee hee Stud fucked....gah ha HA HAAAA HAAAAAA!"

"What's so funny?!" I yelled, trying to sound intimidating but coming across more petulant and hurt. Probably because I was. I thought I was a zipper away from proving my manhood, that I'd dominate this training wheels sissy enough times to work up the game to take on Isabella. And instead, the biggest sissy in the house was laughing uncontrollably at my attempt to sound butch. I wanted to cry, and when I realized how unmanly wanting to cry was, I wanted to sob...

She finally managed to compose herself, pulling herself off the ground and on to her knees, wiping a tear away as she sighed, "Oh my...thanks, Byron, I needed that. I know, I know, I shouldn't laugh. And look I got my dress all dirty...oh poo! But you have to admit, the idea of you stud fucking anyone is pretty funny. I mean, considering you let a sissy stud fuck you down in the basement. And right after Master Darren told you if he caught you again he'd add you to the Harem. I'm sorry, I know it's none of my business, but hee hee the basement has really good acoustics...Hee hee oh golly, I'm about to go off again...but...hee hee you couldn't even wait to haa haa you got to your giggle own room. Hee heee heeeee I'm so sorry but HAAA HAAAAAAA!"

All the blood left my body, and I thought for a moment I might actually faint. The ground tilted and I had to stumble in place to keep my footing. She knew...they all did...every sissy in the Harem thought of me as one of them...I'd never be able to start over...I would always be a sissy to them. And if I couldn't change a sissy's mind, how would I ever change my step-father's? On the other hand, if I could make her think of me as a stud, then maybe I could make everyone see me in a new light. I felt cold and hateful and just plain ugly inside. I knew that it was all directed inward, but I decided to use every sickening ounce of it, my words dripping with venom when I said, "I'll make this simple. I am a Master. You are a sissy. Either suck my cock right now, or I'll take you down to the play room and we'll see how good the acoustics are when you scream so loud that you go deaf."

I looked down and saw that hazy glaze of lust start to fill her eyes. I could barely believe it, but my step-father had been right. If you show strength, sissies will instinctively submit to you...and as Bambi feverishly fumbled with my zipper, I felt stronger than I ever had. My cock throbbing, aching to be sucked, ready to plow into her throat and paint her face with my seed. It felt like it was going to rip through its pantied prison...and that's when I realized I was fucked...

"HEEEEE EEEEE HEEEEEE Cute undies! Ha HA HAAAAAAAA HA AHHHHHH!" She fell back onto the ground laughing like mad. I couldn't listen to it for one more minute. I stormed off and ran up to my room, not even having the courage to drag her down to her cage as punishment. How could I torture someone who couldn't even keep a straight face if I spanked her? I buried my head under the covers until I felt the urge to sob pass. I couldn't imagine facing Bambi again that day, much less Isabella, but it was only mid afternoon. So I did what any manly man would do. I went over to my dresser, found my flask in the underwear drawer, and drank myself unconscious. As my brain swam into the whirlpool of black out drunkenness, I told myself tomorrow would be a better day...


I woke up with a hang over and a sissy's cock brushing my lips. I brushed it away, not wanting to puke on her dick. "Lemme up..." I mumbled and stumbled toward the bathroom, hoping a shower would clean out the cobwebs in my head. I almost fell face first to the ground, so I didn't object when Isabella propped me up and helped me get to the shower. I slumped against the tile wall and slid down to the ground, more dead than alive...but when Isabella pulled the shower nozzle down toward me and started to rain warm water down on me, my body came to life bit by aching bit.

I was too groggy to protest as she soaped me up and scrubbed my soft skin, and besides, there's nothing wrong with a sissy washing her master. I even allowed myself to hope that she was coming around to my way of thinking, showing me the respect I deserved. That is until she stuck two soapy fingers up my ass and cooed into my ear "mmm This spot's especially dirty...it looks like it needs a deep clean." I tried to protest, but before I could even moan a refusal, she thrust her tongue in my mouth and had me sucking passively on it as she pinned my tongue down to the bottom of my mouth, claiming dominance over both of my holes.

I would have stopped her if I wasn't so hung over, half drunk really...or at least I hope I would have. But as two fingers became four, and her kiss swallowed every wet moan down her eager little throat, all I could manage the strength to do was beg her to fuck me. She helped me to my feet, holding me in her arms so I wouldn't fall back down. The warm water cascaded down our smooth skin, making us slide against one another like seals fucking..."Grab the shower rail, sweety. I'm going to show you how sissies cure their hang overs." I grabbed the rail for dear life, my body pressed against the frosted glass, my hips held tight in her hand as she aimed her cock head at my winking little rosebud...

I felt her slide into me slowly, I felt slippery inside and out, soft and smooth and warm, and I was too fucked up to worry why that felt so good at the moment. "Thank yoOOoOooOoooh!" A low, lustful moan fogged up the glass in front of me. I wasn't exactly sure what I was thanking her for. Was it getting me squeaky clean and washing off the filth of my drunken night sweats? Was it for aiming her cock right at my sweet spot every time she sloooooowly filled my asshole with her cock, sending a hot throbbing pulse pumping in my veins, burning out all the poison and replacing it with undiluted sissytonin? Or was it just for the immense kindness she showed in not teasing me while she fucked me? Instead she draped her body against mine, her breasts crushed against my back, her mouth nibbling on my neck and shoulders, her legs sliding slickly against mine, stirring them to life. She wasn't fucking me like I was her bitch, she was fucking me like I was her lover. In retrospect, maybe that was even crueler than when she taunted and teased me...

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