Young Master Ch. 03

She looked at me as if I had just spit in her face, I couldn't understand it, there I was, trying to do her a favor and she looked horrified and betrayed. I didn't know what to say, what to do. She couldn't say anything, it was up to me to figure out what I did wrong....and then it hit me. I felt like someone took my guts in their hand and twisted them in a knot...she couldn't cum. The cage was off, but she didn't dare cum on her own, and after all this time of putting the Masters' pleasure first, she might not even be able to get off without a Master there to use her. I was so hard, but I hadn't been able to get off on my own either. Suddenly I felt closer to her than ever before, and I wrapped my arms around her, pulling her head on my shoulder, whispering "I want you to take my cock out, and rub it against yours until we both cum."

She yelped again as she unzipped my pants and pulled out my cock with the skill and speed of a ninja. My cock was already dribbling precum as well, so there was no resistance as she took both in her hands and began sliding her hips up and down. Soon our throbbing pricks were sliding against one another like snakes in love, feeling like a million needles coated in honeyed heroin were kissing my tender flesh. I felt something powerful welling up inside me, something even more urgent than the surging rush of cum boiling in my balls ready to blow any moment. I pulled her head up, saw the look of pained ecstasy in her eyes, and crushed my lips against hers in desperate attempt to burn away the shame...

She whimpered into my open mouth and our tongues danced, sliding against one another faster and faster keeping time to our slick sexes, our whimpers, moans, and yelps the music we waltzed to. It was a painful moment, haunting in its beauty and its paradox of perfect pleasure and pointless pain. If only the moment could last forever, our perfect union, a connection based on kindness and a mutually selfless expression of sensuality. It would be Heaven...and Hell...

Because even as we ascended closer and closer to Heaven as our bodies were grinding against one another, the flames of Hell possessively refused to let us go, the pain of unrequited lust creating an emptiness deeper than any love we could hope to fill it with. What I wanted was to stay like this forever, what I NEEDED was to cum right away, before I suffered permanent brain damage. Heaven and Hell, a pleasure chased that can only be attained when you let it lose, a connection more profound in the separation than in the union...it was all so fucking zen. But I didn't have time for philosophy, and neither did Sakura, apparently. She cried out, "Please, Mastersan, please humor this sissy's inept efforts and cum. I can not dishonor myself by cumming first, but oh fuck me sideways, I need to cum so fucking bad!"

Hearing her voice tear apart as a raw savage beast ripped itself free was all it took to send me careening over the edge, my cock kissed by a million angels, their burning lips sending my spirit soaring, all across Sakura's blouse. A millisecond later, Sakura sobbed as her body shook violently, a thick load shaking free and landing on my polo. We both just held each other until the tremors stopped, my skin tingling as I came back down gently to the earth. I wanted to enjoy this moment free from shame or doubt for as long as I could, but Sakura landed a little harder than I did. She cried out, "Please, most generous and magnanimous Mastersan, please forgive this lowly sissy for desecrating you with her vile waste. I will commit seppuku at once!"

I didn't wait to find out if she meant a metaphorical disembowelment, reassuring her, "Don't worry, Sakura, I have plenty of shirts. I'm just glad we were able to help each other. If you like, I can hold onto this cage for you so you can breathe a little easier." She seemed immensely grateful for my forgiveness, which made me feel a little uncomfortable, as it reminded me of the yawning chasm between our roles. But when I offered to keep her cage, her expression turned to one of horror, as if I'd casually suggested she sleep in a snake pit.

"Please, Mastersan, this pathetic sissy is not as brave and powerful as you. She does not dare invite the wrath of Darriussan upon her if he finds her without a cage. I beg you with all my soul, please lock me back up." and as I silently locked her cock back in its painfully confining chastity cage, I was reminded of the even greater gap between men like Darius and men like me. But for the first time, I couldn't say if he was stronger than me, or just crueler. I suppose it didn't matter to Sakura, that knowledge wouldn't protect her from his sadistic whimsy. As I gave her leave and watched her walk away with those tiny, shameful steps of hers, I hoped I would find a way to truly help her someday...but first I would have to find a way to help myself.

I spent the rest of the afternoon and most of the evening lost in thought. I kept asking myself how could I help myself, and was there anyone who could help me? I wanted to believe Isabella could, but I didn't know which side of her to trust. Was she the malicious minx that loved nothing more than leading me on and letting me down, or was she the kind and gentle soul that took care of me when I was in my cups? Maybe she was both, maybe she played her vicious little games to help herself, a defense mechanism to keep her from giving in completely to the siren call of surrender. If that was the case, maybe we could help each other. I was resolved to try, and I now thanks to Sakura, I knew just how to connect to her...

When she came into my room she was wearing a too tight school girl outfit that I immediately recognized as Sakura's. While on Sakura it was cut to give the impression of a demure innocence, on Isabella her extra height made the skirt shockingly short, and her more prominent attributes made it impossible for her to button the top of her shirt, leaving her cleavage all but spilling out. She seemed to enjoy the effect it was having on me, "Sakura told me how you played sissy chicken with her today, so I thought maybe you wanted to play the same game with me. I can't wait to see who lasts the longest."

I didn't know what she meant by a game. I was just helping Sakura out, it wasn't a competition. And I sure wouldn't have played it if I knew they called it 'sissy chicken'. I still wanted to do the same with Isabella, it wasn't to prove anything about who was stronger, I just wanted to be closer to her. I decided to take a gamble in hopes that if I played the game her way, maybe we would connect the way Sakura and I did, and then she wouldn't care who 'won'. "Alright, I'll play. But, isn't there anywhere safer to play than here? We can't keep doing this in my room, the door won't even lock."

I regretted my prudence when she told me that the safest place to play sissy games was in the basement. No one ever went down there at night and we'd have the place all to ourselves, not counting the eager sissy audience. So with all the courage I could muster, and a damn sight more I was just faking, I followed her into the basement. I was surprised to see there weren't any sissies in the cages and more than a little relieved. If they were all gone too, then maybe this wouldn't end in embarrassment. But she just smiled and took me by the hand further into the basement, further than my step-father had taken me on his threatening tour. I wondered just how big the basement was and started to think it was more like an underground compound when the winding tunnels finally led us to a room filled with whispered giggles.

We stepped into a room filled with cots, enough to hold a sissy army. I wondered just how many sissies Darren planned to own. All the other sissies were there...Sakura wearing only her cage. blushing and looking away as we made eye contact...Bambi practicing pouting in front of a mirror, turning with a giggle as she saw me in the reflection....Lola a look of haughty passion on her face as she sat on Cunt's back, slapping her ass to get her to carry her around the room...the look of serenity on Cunt's slack face telling me it wasn't entirely forced...they all turned to me in stunned surprise, and Isabella finally broke the silence. "Well Master, this is where we sleep. They would probably just keep us in the cages overnight, but they don't want our skin getting those nasty grid marks now do they?"

"I...I guh guh guess not..." my stuttering sputter was returning with a vengeance. I didn't like the hungry look the sissies were giving me and all of the sudden I wondered what the stakes of this not so little game where. "Uhm what eh eh exactly is the gah gah game, Isabella?"

She took me by the hand, and led me to the center of the room, I felt surrounded by sissies, crowded by their eyes, I just stared dumbly as she started unbuttoning her shirt, when she saw the clueless expression on my face, she laughed and said, "What are you waiting for, Master? We both have to be naked to play sissy chicken."

I started pulling off my clothes as fast as I could, I had no idea what sissy chicken was, and yet there I was, standing before her absolutely naked, my cock already aching, dripping precum on the floor at the sight of her so soft and so hard at the same time, I hoped she wouldn't notice, but of course she did, "Oh this won't do at all. If you want to win at sissy chicken you'll have to last longer than this. The rules are simple, we both rub our cute little clits together in a race to see who cums first, only who ever finishes first, comes in last. I'd tell you what happens to the sticky little loser, but I don't want you to cum before we can even get started."

I saw the fire burning in her eyes again, threatening to melt me on the spot, I looked around the room, and saw that they were all waiting for it to happen. Licking their lips in anticipation of what was to cum. I don't know why, but I had the craziest notion that I might actually be able to win this time. I had lost every battle of wills I'd ever had with her, but in a way, that gave me an advantage. She wouldn't be expecting a challenge. And I gambled everything on that, hoping not only to win the game, but hopefully her heart. Somehow I just knew that if I could only connect with her as equals, just once, we could put all the games aside.

I stepped closer and she took my cock in her hand, smearing my copious leakage all over her smooth sissy stick, and then began rubbing it against mine. I knew from the moment she put her other hand on my chin and lifted my gaze to hers that I was doomed. The sharp angle of her smirk cut me down to size...the tip of her tongue stuck out of the other side of her mouth, ready to lap me up...her nostrils flared like a savage beast stoking the fires that made her cheeks flush with anticipation, a single bead of sweat running down her smooth skin, making me wish I was tall enough to lick it off...her eyes held me prisoner, the reflection of a simpering sissy trapped inside them. I tried to look away in one last futile effort to hold out just a little longer, but that only made things worse. I saw her cock dwarf mine as it crushed against it, pushing it into my soft stomach, her cock-head poked my belly button with every thrust of her hips, making me feel penetrated and helpless. My puny penis was covered in my slick juices, it gave no resistance as her superior member mashed against it, squeezing more and more out until I was thrust my hips back against her, not to try and make her cum first, but to end this sorry spectacle my legs buckling as every muscle went rubbery in response to my sticky spasm. My tiny prick oblivious to the shame of it ecstatic eruption sending a warm buzz throughout me that lasted just long enough for Isabella to pick up my limp body, her muscles popping from underneath her silken skin, and hover me right over her cock.

I came to my senses in time to realize my asshole was puckered around the tip of her cock and I was about to get stud fucked by my sissy in front of a live studio audience. "Please, I AIEEEEEEE!" My leakage had made her cock slick, and my tight little hole was no match for the forces of gravity. I cursed Issac Newton as my legs wrapped themselves around her and my face buried itself in the nape of her neck, hiding my shameful blush in her raven locks...

"Tee hee Make him your little fuck dolly, Isabella!' Bambi bubbled, reaching into her panties and stroking herself feverishly as Isabella pulled me off of her cock, every inch a revelation. Every time I got fucked I discovered something new about my treacherous body. How the slightest angle could be the difference between Heaven or Hell, and take me that much closer to the place where they were one and the same.

"Si, pound this puta's culo until she cries for her papi" Lola had gotten into the show with a frightening zeal, taking poor Cunt by her ears and rubbing her tanned cock across her face until she began obediently taking it all the way down her throat. The look in Cunt's eyes terrified me more than anything, it was one of recognition...seeing the bitch in me surrender to the physics of a phallus pushing into me all the way down to the hilt, pounding my prostate and sending a chain reaction to every raw nerve in my ass. I clenched down on it, felt my asshole milk her hard hot flesh for more sensation. I needed to feel more, to drown my mind in dick doped drool, to escape this nightmarish reality for just as long as she could keep fucking me...

I looked to Sakura for support, hoping to find a single pair of kind eyes in the crowd. Instead I saw the same hazy hunger. I wasn't a Master to her anymore, wasn't even an equal, I was just a sissy chicken and she had no sympathy for anyone weaker than herself. "Yes! Fuck her harder Isabellasan! Send this sissy to the Hell of Never ending Cum!" I thought I might already be there, I couldn't tell if I was cumming anymore, her cock had truly transformed my asshole into a wet cunt, and my body into a vessel for unholy orgasms. Possessing me like foul mouthed demons, twisting my lips into a lewd moan, screaming "fuck me Mommy! Fuck me MOMMMEEEEE! Make you your little cum dump whore! EEEEEEEEEEE!"

Time slowed as she swelled inside me, her cum shooting up inside me sending me careening off her cock and through the basement ceiling, blasting through the floors and out the roof, piercing the sky and cutting through the clouds, burning up as I broke through the atmosphere like some reverse comet, streaking past the speed of light past the edge of the universe, reaching that perfect place where nothing exists, not even me. Everything was empty...it was Nirvana...

I crashed back down to Earth just as suddenly, Isabella dropped me to the floor and laughed as the sissies scrambled to suck her cum out of my abused asshole, to lick her clean in tribute to her triumphant victory. I curled into a little ball, trying to block out everything trying to get back to that wonderful nothingness..."Hee hee Look! He sucks his thumb! I thought only I did that!" Bambi tittered. Luckily I must have hit my head when I landed, because I blacked out, finally escaping.

I came to in spurts, feeling Isabella pick me up and check to see if I was okay..."Jussssst a liiiiiittle buuuuuump. Whaaaaaat a sssssssissssssyyyy" Carrying me out of the basement....sneaking me back up to my room...tucking me in...and giving me a little kiss on the bump when she was positive I was already passed out...It had been a good day after all...

Thursday

I woke up sore, and sorely vexed, with Isabella's morning wood sliding up and down between my ass cheeks as she cooed in my ear "Gooooood mooooorning, Master. Were you dreaming of me? Dreaming of my fat sissy sausage sliding up your cute little boi pussy? Well guess what, you're dreams are about to cum true..."

I leaped out of bed, angry at how she used me last night and afraid I was about to let her do the same this morning. She looked amused at my sudden outburst and I saw that she had changed outfits for me again, this time wearing a much too small Girl Scouts Uniform, only bright pink with 'Sissy Scouts' emblazoned on the shoulder. I saw various badges for anal and crafts, ass to mouth respiration, cumminity service. In one hand she held up her lacy pink thong, and the other a new badge, "Aww, don't you want to earn your deep throating badge today?"

She wasn't even trying to trick me anymore. She thought I was so broken that I'd willingly surrender without even the illusion of a fight, and as I licked my lips, I saw where I might have given her that impression. But I drew a line, then and there. Whatever I was...man, sissy, or something else entirely, I deserved better than her. And I let her know it. "No, Isabella, I don't want anything from you. Now or ever. I don't want you to come near me. So why don't you..." I was about to tell her to lock herself in one of those horrible cages, but just the image of it twisted my guts into a knot. No matter how much she hurt me, I still couldn't bring myself to hurt her back. "why don't you clean up around the house?"

I turned my back on her sullen pout before I couldn't stop myself from kissing it off her face...and with that, I was free...or so I'd hoped. But with every step I took away from her, the closer she was to my thoughts. All I wanted was for her to look at me with those kind eyes all the time, that soft smile melting into mine in a never ending kiss. But I knew that would never happen. If I did see her softer side again, it would only be to play another sick little game. I was tired of being her Charlie Brown, always giving her another chance to pull the football away at the last moment...only instead of landing on the hard ground, I fell onto her hard cock.

I spent a good ten minutes trying to shake THAT image out of my head, and decided to do something to keep it out. I headed down to the gym for the first time in my life, determined to make something of myself. I changed into a tank top, workout shorts and sneakers, and I was fired up, I was raring to go, I was chewing up matches and spitting fire...I was completely lost...where was I supposed to start?

I decided to try something simple, that even I could figure out, and grabbed some free weights to do curls. I looked around for the lightest one, but all I could find was fifty pounds. So taking my good right hand and gripping it as tightly as I could, I lifted with all my might. Pain steadily stabbed it's way up my arm, but I tried to push through it, knowing that with punishment comes reward, and managed to lift it several inches off the ground before feeling it pull me down to the ground. It was strange, there was only room for one hand, but how was anyone supposed to lift fifty pounds with one hand?

I looked around for something more humanly possible, and settled on a treadmill. I fiddled with the controls until I found the slowest pace and easiest virtual track and began running in place as the belt moved below my feet. I felt the impact travel all the way up to my buttocks and I set forth to see how far I could push myself. But after a ten or so minutes, the routine was still somehow going...my legs felt like knives were dragging up and down them and my lungs felt like I was breathing battery acid. And then the machine sped up...set to a blistering 'jog' and hurling me to the ground, landing right on my pride...

It wasn't fair...my step-brothers made exercise look so easy. I briefly considered asking one of them to help train me, but immediately rejected it. I could just imagine what Dirk would say if he saw me failing at the lowest levels of fitness training. "Holy shit. You're even more pathetic than I thought. How can you even call yourself a man?" I looked up at the towering mass of muscles leering down at me and realized with a start that I wasn't just imagining his voice...