tagTranssexuals & CrossdressersYoung Master Ch. 02

Young Master Ch. 02


There I was, still impaled on a shemale's cock, one belonging to what was supposed to be my sissy slave, wearing her bra, her cum on my cheek along with my post-fuck smeared make-up, and my cum running down the full length mirror. "I fell" wasn't the best explanation for what happened, but it was all I could think of with my step-father's hulking frame looming over me. I knew I was fucked...well more fucked than already had been, but I still hoped for some miracle to save me.

"You...fell? I'm not even going to begin to catalog the many reasons that is the most insultingly stupid lie I have ever heard. I'll give you one more chance to tell me the truth, and then I'll ask Isabella. And, Byron, you had better believe she will tell me the truth, so lie at your own peril."

I didn't know what to tell him. I was so ashamed, every doubt and reservation I had before my mind seemed to shut down came screaming back at me. I just wanted to crawl in a hole and hide from his contemptuous eyes forever. But I knew I couldn't hide from those blazing eyes; they'd scorch the earth to find me, and when they did...I shuddered to think of the countless ways he could hurt me, and my entire shameful story came spilling out...

I tried to explain it in a way that didn't paint me as a natural born sissy, tried to explain that all I wanted to do was to prove I was a real man, but it's hard to do when explaining how your personal sissy slut seduced you, sissied you up, mouth fucked you, spanked you, fingered you, and fucked the cum out of you. What I finally managed to stammer out as a final, flimsy explanation was "I'm sorry...she's just so much more experienced than me. I shouldn't have let her trick me...but I swear, none of this was my idea and I never would have done any of it if she hadn't gotten me so mixed up."

As excuses go, it was pretty pathetic, and it didn't exactly make me a candidate for man of the year, but at least it didn't paint me as the sissiest sissy that ever sissied, and I hoped that might be enough. Even I could believe it if I tried hard enough. All that was left to do was wait and see if this immovable mass of malice would accept it. "Well, Isabella, is this true? Was this your doing?"

She had already slipped out of me and crawled over to his feet, curled up around his legs like a kitten. I wondered where this submissiveness was when I needed it most, but mostly I wondered if she'd sell me out to save her own downy soft skin..."Yes, Master. I seduced the confused little virgin, and it was sooooo easy. I know it was bad, but please forgive me, Master. He's just so cuuuuute."

I heaved a sigh of relief that quickly turned into a horrified gasp as my step-father savagely kicked Isabella in the stomach, knocking the breath out of her and making her curl up into a tight little ball of pain. I tried to say something, to beg him to stop, to tell him it wasn't really her fault, anything to stop him from hurting her. But I couldn't breathe. Finally I saw her stirring again, looking up at him with a manic smile, her eyes glazed over with lust..."Thank you for punishing this worthless slave, Master. Please, hurt me some more...I deserve to be punished."

It was so strange...this was the same sissy that had me completely twisted around her little finger...and then shoved it up my ass. But around Darren, she seemed to get off on being slapped around and put in her place. Is that why she teased and toyed with me? Was she just fucking with me to get me to push back? I started looking at her in a whole new light, and from the perspective she wasn't quite so cute. Maybe it was just easier to blame her than to accept what I let her do to me, but anger felt so much better than guilt, so I nursed on it like a baby...

"Hmm...Normally I'd have both of you in stocks for a week with a fuck machine pounding your ass the entire time. But perhaps you have a point, Byron. Isabella was just being Isabella, and maybe I could have done more to prepare you for the world of Men. So I'll let this pass this one time and we shall never speak of it again. But I warn you Byron, by marriage or blood, I will have no sissy carry my name. Do you understand?" His rage seemed to have tempered, but that just left him rigid as cast steel. It was all I could do to nod without shivering.

"Good, because you know I don't like to repeat myself. Now, I want you to pay close attention, because I am about to teach you how to keep your sissy in line." His tone was just as calm as if he were talking about changing the oil, and with the same casual authority, he pulled Isabella up by her hair until she had to stand on her tippy toes to avoid being lifted into the air by her thick, luxurious locks. He pulled her into a savage kiss, practically swallowing her mouth with his. There was no affection in it, no romance; he was merely claiming her mouth as his own personal hole. And for her part, she seemed all too willing to surrender it, her eyes rolling back in her head as she passively accepted him raping her mouth...

I heard a pathetic little yelp as he dropped her to the ground, saw her crumpled on the floor as she looked up at him with slavish devotion. I knew I couldn't toss her around like Darren could, she was taller than me and everything. But as I saw her running her tongue over his wingtips, sucking on the tips, her eyes glued to his the entire time, I knew I wanted to make her do the same to me. I wanted to make her pay...and I wasn't going to miss a single second of this hands-on demonstration on exactly how to do it...

"You're sucking the wrong tip, bitch." He pulls her up by her hair again, twisting it in his hand so that she can't budge with out losing a fistful of hair right from her sensitive scalp. With her lips right at the top of his pants, he says, "Your smart mouth got you into this trouble, let's see if it's smart enough to get you out." I stared in perplexed nervousness wondering how she could possibly free his cock using just her mouth. I almost started feeling sorry for her. I know she probably would have been giggling if our roles were reversed, but I just get squeamish when I see someone in pain. Maybe because I can't help but imagine what it would feel like. I held my breath, hoping for a miracle...

"The fuck..." I closed my hand over my mouth, not wanting to interrupt with another outburst. But I could barely contain myself. She was using her teeth to bite the slack of his belt and moving her head ever so slightly to work it out a little bit at a time. I couldn't stifle a gasp as she finally got it loose, but my step-father seemed unimpressed...

"Today would be nice." he said with a yawn. I couldn't believe it, this was the hottest, most submissive human pet trick I'd ever seen, and he was treating it like it was chore to watch. Again I felt sorry for her against my better judgment, hoping he'd acknowledge her skill as she bit down on the button of his pants and worked it through the eyelet by tilting her head. But he just looked at her with frustrated boredom. Finally she took the zipper in her teeth, whimpering as she tried to move her head down just a little further, just far enough to free his cock, but he wouldn't give her an inch...or twelve as the case may be.

She looked up in desperation, surrendering her pride once more as she begged, "Please, Master, please move my stupid whore head down so I can get to your cock. I'm too weak and pathetic to do it on my own." She had the look of one who had to deliver this speech many times before. I wondered how she still kept the fire in her eyes when my step-father doused her flame with his callous games. I was remembering why I hated him, why I feared him...why I'd do anything to prove myself to him. And when I saw him move her head down with the zipper in her teeth as casual as if he were just unzipping his pants, I understood the hopeless frustration Isabella must have been feeling at that moment...

When she finally manage to unzip him, his cock sprang forth like a wild beast. I couldn't believe it...I never knew they could come that big...that thick...I don't know how he could get a hard on that size and not pass out from the loss of blood flow to his brain. Hell...I felt lightheaded just looking at it. She seemed to be in a daze too, her mouth open so wide it looked like her jaw had come unhinged. And then without a moment's notice, he crammed it in her throat, burying at least six inches down her gullet in one ravaging thrust.

I held my hand to my throat, remembering how rough a few inches had felt, unable to stop myself from imagining what it would be like in her place...She gagged on his cock, even her well practiced throat unable to take his full length dry. 'Luckily', her spit seemed to make the second thrust a little easier, she managed to get two thirds of his massive member before choking helplessly. This time he held her in place until her face turned red, her eyes rolling back in her head...he snapped her out of it with a hard cockslap to her face, and I couldn't help but imagine myself moaning as I drooled all over myself just like she did...I shuddered as I realized what I was imagining, and tried to force it from my mind...

Instead I tried to imagine myself as my step-father, now managing to bottom out in her throat, and then yanking her off me by her hair, holding her just out of reach as she tried to get back on it, the veins in her neck looking like they would burst any minute...and then slamming her right back onto it. Before long it was a sloppy blur of spit and hair bobbing back and forth on his prick. But try as I might, I couldn't see myself doing that to anyone, even to the sissy that used and abused me. And even if I could manage to keep her in line long enough to force her to suck my cock, even if I ignored how much stronger she was than me, what would be the point? Is forcing three and a half inches of hard meat really that demeaning? Honestly I think it would just make her laugh...

But she wasn't laughing at Darren, she was too drunk off her own humiliation. I didn't get it...even though I was the same way with her. Why would anyone want to be treated that way? To be used like a cock sleeve? To hear my step-father call me "A cock sucking sissy bitch, a cunt mouth whore, that's it, fuck hole, get ready for my seed." I mean...call her that...I got a little caught up in the moment. And when he finally pulled her off and exploded in her face, coating her with a thick layer of white mucousy shame, I had to bite my lower lip to prevent from whimpering along with her.

My step-father looked right at me, but it felt more like he was looking inside me, judging me silently. I opened my mouth to say something in my defense, but I didn't even know what I had been accused of. Either way, nothing came out but a raspy breath. After an eternity of crushing silence, he said. "So you see how you are supposed to get a blowjob from a sissy. First and foremost, they should be the ones with a face full of cum. And that's just the warm up..."

Isabella was hungrily sucking his balls as he gave me his lesson on Master/sissy etiquette. She was clearly trying to get him hard again as soon as possible, but I didn't see how that could be. If I sprayed that much cum, I'd be dry for a week. Even with all the squirting I'd done today, it wasn't half of his giant load. But to my everlasting horror, his cock managed to rise in defiance of gravity and all that is holy. Apparently, I was the only one surprised, as Isabella didn't blink before turning around and hiking her ass in the air, wiggling it invitingly...I imagined how lucky I would feel to be in his shoes right now, to see someone as beautiful and confident as Isabella offering herself to me so completely like that.

I guess he didn't feel so lucky, as he kicked her hard in the ass, sending her in a tumbled heap onto the floor, just barely managing to keep wet, jagged sobs at bay. "Undress me, you vapid cunt." I would have killed him if he did that to me...well, I would have wanted to. But Isabella just looked up totally apologetic and wasted no time pulling his clothes off and neatly folding them before setting them aside. I guess it's easier to feel guilty than angry after all, especially if the man you'd feel angry at could snuff you out like a candle. If anything, that impotent rage would only make me angrier at myself for being too weak to stop him. No, I'd much rather convince myself I was wrong and work tirelessly to make it up to him...if I was her I mean.

When he was completely nude, I couldn't help but notice his physique. He had the body of a man half his age, if that man had a great fucking body anyway. He was tall and wide, but virtually every inch of it was covered in taut, bulging muscle. The only exception was a little looseness here and there, as time couldn't be beaten down entirely. If anything, these minor imperfections merely added to his appeal, as it gave him the kind of august authority of an elder statesman. He had nothing to prove...he had already forgotten more conquests than I ever dreamed of having. Every little detail, from the wry wrinkles around the corner of his eyes, to the salt peppered in his lush mane of chest hair, all of it painted the portrait of a living legend. Not that I notice those kinds of things, but when it stared me in the face, I just called it like I saw it.

He lifted her into the air like she was weightless, and I realized with a blush that he could lift me even easier. She squealed with girlish glee at the gravity-defying rush of total helplessness. And then he shattered her illusion, showing her the full weight of gravity as he let her sink down onto his cock, moaning incoherently all the way until she nestled at the root, her arms were flung around his neck, her legs wrapped around his hips. She had more Real Man inside her ass than I had inside of my entire body, and of the two of them, it only made sense to put myself in her place. After all, I'd never been balls deep inside a sissy, but I had felt my asshole stretch and surrender to a superior cock, enduring the pain, then ignoring it, and finally worshiping it, knowing it brought the exquisite explosions of pleasure along with it.

But this...this was a cock of a whole different breed. This was no sissy cock like I had been so impressed with earlier, this was a Real Man's cock, and I just knew it would kill me if I ever tried to slide up and down it in a furious flurry of whimpers, moans, and wet smacking the way Isabella was. Not that she had any choice, the way my step-father manhandled her, she was little more than a cum-rag doll for him to play with. But even though she was being used with no regard to her comfort or pleasure, I could tell she wouldn't give it up for the world. Maybe it was because she had no choice in the matter. If she really had just held me down and raped me, would I feel so stomach-churningly guilty about it as I did right then? Or would I feel freed from all guilt and responsibility by the powerful arms of my step-father? Using me so savagely, forcing me to love it, enslaving me in his embrace, freeing me from reason and dignity and manhood, making me a thing, not even a sissy really, just a long continuous screaming orgasm. My head was swimming, I couldn't stop 'sympathizing' with her, but I knew I had to try. I had to think about fucking her instead. "Ha, I can see you like this, boy. Alright, come over here and get a closer look. I want you to see her face when she offers her soul to me."

He put her on the ground and flipped her over unceremoniously. He lifted her ass in the air and spread her legs as far as they would go. He didn't even have to tell her to hold her ass cheeks apart. I saw her now gaping hole and wondered if I could survive feeling that empty. And when I got down on my knees in front of her and he began fucking her in earnest once again, I wondered if I could ever survive being that full. Even an experienced sissy like Isabella looked like she had trouble taking it. In a way, I suppose she didn't survive. Her eyes went totally blank, her mouth started dribbling gibberish, and I could see the soul get fucked out of her body. She was just a fuck husk now, and there wasn't even enough left of her to tell me how much she obviously loved it. That was the part that scared me the most. What happens after you die? That's the easy part, it's coming back to life that's scary. It's like bringing back demons from Hell clinging to you, corrupting me, damning me forever to see the world through a bitch's eyes. To have an asshole that twitches and aches when it sees a fat cock. To feel an emptiness where I know nothing should go in the first place. To watch the most beautiful creature I've ever seen get the life fucked out of her and to be reborn in a newborn wail of ecstasy, and to cover her face in cum as I jerked my tiny nub, dreaming of being her...

"That's more like it, stud, cover that sissy's face with cum. Show her who's boss. Unh unh FUCK!" Every muscle in his body surged as he emptied a gallon of jism inside her burning cock hole. Her own cock jumped around like a fire-hose that got away from the Firemen, spraying ribbons of cum all over her legs and stomach. I fell back, spent. Cursing myself, cursing my step-father, but most of all, cursing Isabella. I remembered my anger now and I vowed never again would I feel sorry for her or put myself in her shoes.

"The important thing to remember, is that whether your cock is too big or ahem....too small, with sissies it doesn't matter. They exist for your pleasure. And if you show them confidence and inner strength, they will surrender gratefully. Do you understand now, Byron?" He looked at me expectantly, patiently even. I almost fooled myself into seeing embers of kindness glowing in his eyes as well.

I took a deep breath and steeled myself. Confidently as I've ever said anything, I replied, "Yes, sir. I've learned my lesson and then some. I can't wait to show this bitch who's boss." I felt an angry energy building inside me, and at that moment, I really believed I could be a Master after all.

"Good, because now I want you to get cleaned up, put on some normal clothes, and follow me. I'm going to show you what's behind door number two. I'm going to show you what it's really like to be a trophy sissy."

I was a little perplexed by his ominous tone. I thought I already knew what it was like to be a trophy sissy. Honestly it wasn't much different from the life I already had. You got to lay around all day doing nothing, enjoying all the luxuries someone else has striven so hard to work for. About the only differences I could see was you didn't get to leave the premises unescorted and you got fucked all the time. Still I was doing a pretty good job of convincing myself that last part was a bad thing. And as I looked at myself in the mirror, having just washed my face of the make up and cum, I vowed once again to find a way to prove my manhood.

"I don't have all day, Byron. Unlike yours, my time is actually worth something." I jumped in a rather unmanly fashion as his voice bursts through the door and hurriedly get dressed in a plain white button up shirts and khaki slacks. I didn't want anything too colorful sending the wrong message. I gave myself one last pep talk and emerged from the restroom with my head held high. Well as high as I could at five feet three inches.

"Finally. Now don't dawdle. Byron. We'll start off by showing you the sissy's quarters." I nodded, resolutely I hope, and followed my step-father, with Isabella trailing closely behind. Her perfume teased my nostrils, reminding me of her tantalizing taste, but I shook the image from my head and focused on our little tour instead. I was perplexed, we had already passed all of the guest wings, and each of my brother's personal wings. The rest of the grounds were common rooms and I couldn't figure out where we were heading. When we finally reached the door to the basement, my heart stopped.

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