Billy's Challenge

(Mm) (anal) (humil, viol) (nc)

I am really so sorry that we had to get rough with young Billy. We broke his nose and never really meant to. I would really hate to mess up that beautiful slender face, at least until we were finished messing with him. And let’s face it, a broken nose, clogged with blood means that the cunt cannot properly breathe when he is taking a big dick down his throat, so it fucks that up too.

But the asswipe just would not listen. It was a simple request, nothing serious, no big deal. We were in between fucking him at both ends, ten of us, and we were resting our dicks and having some beers. One of the guys got the fun idea of seeing just how much young Billy could take up his ass, but not with us holding him down and forcing it into him and him crying his teenage eyes out. No, we wanted to see how much he could force himself to take. It’s always lots of fun when a boy willingly hurts himself and puts himself through great pain to please us.

I love to push a boy’s pain limits, and then reward him by saying to him, “You see, and you thought you couldn’t do it. You see what a little persistence accomplishes. Boys nowadays don’t push themselves hard enough. They don’t want to go that extra step just because it hurts.”

So, whom the fuck cares if it hurts, it is a task that must be performed. I stupidly thought that Billy had learned that lesson. I thought I had impressed on him that he had no option but to do whatever the fuck I told him to do. I mean, Billy seemed like understood. Even though he has a steady girlfriend at school, he took all of our big leaking dicks into his cute mouth, he licked our balls, he ate our asses.

After you’ve sucked ten sweaty masculine shitholes several times, it changes a boy forever. I told him, when he was in a drugged and impressionable state, that his girlfriend might smell the stink of our shitholes on his breath for a few weeks, and perhaps it was best if he did not kiss her while he was playing with us. This really saddened him, but I think it made an impression on him.


I guess he really thinks he loves the teenage cunt, but I hope he learns to love dick up his asshole and down his throat as much. I love breaking in a teenage boy virgin ass. The rectum is so tight and pretty, and the ass lips so sweet and appealing.


And, let’s face it, a straight boy’s asshole is sacred to him. He does not like to contemplate men shoving their fat dicks up it and filling it with baby batter, treating him like a fucking cunt, which is precisely what his asshole will become in time, a fucking cunt to fuck.


You know, I work very closely with my fellow theater associates, and after I am finished filling a boy’s tummy and asshole with my cum, I often offer him up to my friends. This is for the boy’s sake, as well as the pleasure of my buddies. The boy learns that he is not just the special fuck toy of one man (me) but that he must get fucked by anyone I want him to. That I own his new boy-pussy, and I can give it to any of my buddies. The boy must accept that to become sincerely submissive. I decide who fucks him or who fills his mouth with piss. That is my decision to make. He does whatever I tell him to do. I thought young Billy, an aspiring actor, understood this until the dildo game.


We had some innocent fun writing on his cute tight tummy with a magic marker and fucking the shit out of his ass and mouth. As I say, we were resting but decided that while we rested that Billy should entertain us. Why the fuck not? Billy had been a good fuck boy. His tittie exercises were coming along fine, and he had shaved every inch of hair from his smooth young body.


I nicely suggested that while we were resting up for the next fuck round with the boy, that he entertain us by shoving some dildos up his ass pussy to keep it open and ready for us. Billy was a bit resistant. He said he was exhausted from taking so much cock up his hole and down his throat, and could he not rest too? Why, why the fuck should he rest. We had done all the work plowing his pussy and mouth. We had worked up a sweat banging into him as hard as we could. Billy had it too easy, and he was spoiled.


He did all right at first. He took the eight-inch dildo just fine and fucked himself hard on it at my orders. It was a sweet sight, a straight teenage boy fucking his own asshole. His nice full young dick actually started to respond a bit. I do not allow Billy to shoot his load except when given permission, which is not very often.


Anyway, the nine-inch rubber dick gave him a bit of trouble, as it was so fucking thick. A thick dick or dildo can often be harder for a boy to take than a longer but thinner one. As you know, from my work with Ben and others, I am usually fascinated with stretching a boy’s fuckhole as much as humanly possible, but I had not even gotten into that with Billy yet. This was just a simple game to pass the time.


The ten-inch dildo gave him real trouble, and I could not figure out why since he had taken ten inches of a real prick. Again, perhaps, it was the thickness. By twelve inches, he was crying and protesting. He was complaining that he just could not take it.


“I’m trying as…as hard as I can…I just can’t…my hole can’t take it.”


“You simply have to try harder. I’m not going to accept any nonsense from you!”


Well, we finally got the twelve-inch wrist-thick one all the way in. He lay there, panting. We told him how proud we all were of him and encouraged him to fuck it in and out of his boy-pussy. After a bit, he did an acceptable job.


However, it was the big fucking thirteen incher that stumped him. It is quite thick and would cause anyone considerable pain. That is to be expected.


“Of course it hurts,” I told Billy. “If you pass out from the pain, we’ll piss on you to revive you.”


I even let him suck on my flaccid dick a bit, just to comfort him, but he still would not do it. He just moaned and groaned that he could not take a thirteen-inch dildo.


“My hole’s too small…I just can’t…it’ll rip my guts up…really, sir, it’s too big.”


He was being foolish, and I fully admit I lost it. I just lost patience with him. I hauled off and punched him in the nose, broke the fucking thing. Oh, not a bad break. It hardly swelled at all, but we heard the crack and saw the boy writhed in pain. We got some ice and bandaged the bridge of his nose where it had been split a bit.


After we stemmed the flow of blood, I nicely told him to commence with shoving the big red thirteen-inch dildo up his boy-cunt. I warned him that if he disobeyed me again, he would get a lot worse. I repeated that his pain and discomfort didn’t matter; only my pleasure mattered. The essential thing was for him was always to do what I said, no matter how uncomfortable or painful or humiliating or degrading.


I think I finally got through to him because he got that big fat thirteen-inch fucker up deep into his guts. We felt it pushing out his slender tummy. He almost did pass out from the pain several times, but we spit in his face to keep him alert. Getting the big head in was not, in the long run, nearly as demanding as shoving the thirteen inches deep enough. He pitifully kept asking if it was deep enough. Of course not! It had to go all the way in! He kept crying.


I showed him a photo of another boy of mine, from a few years ago, sitting on and impaled by a traffic cone! Now that is commitment.


“It’s going to ruin me.”


I said, “Probably, but that is no concern of mine.”


By the time any real damage was done, he would be a mindless fuckhole, and I would probably have moved on to something newer and younger anyway. Fortunately, before the fucking had started, Billy had been given four enemas, so he was really clean except for the loads of cum up his hole that helped to lube the dildos. And as you may have guessed, knowing how thorough and complete I am, Billy had to lick the dildos clean of ass scum.


And then, after all of that, with Billy mentally and physically wiped out, we were ready for another round of fucking! He realized he had no choice. He simply had to take it.