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Status: In Progress  |  Genre: Humiliation Sex  |  House: The Humiliation Board

This is the short story of high school senior Ben who went down the wrong path and found his entire life totally ruined. The story contains humiliation and rough sex.

BEN'S TALE by dale10

All characters in this fantasy are 18 or older. the author does not condone any of the action in this tale.


(Check out my brand new novel called "THE MASTER SINGER" on Amazon. it is about gay love, opera and the Nazis. You can find it and my other books under D.H. Gutzman.   I rely on your support to allow me to continue to write these kinds of stories as a hobby.)  



I was distracted from my reading of anew translation of “The Odyssey” by the boy’s grunts and moans and occasional screams coming from the next room. C.J. was working on stretching high school faggot Ben’s asshole.  Many of you have asked me for more information and photos of my time training Ben, one of the highlights of my varied and colorful career.


I was remembering him just the other day and dug out some photos. Ben was special to me and I have often written about him. He started out as many a high school boy did, questioning his own sexuality and enjoying my stories. Don’t get me wrong, Ben was a girl fucker when I first met him, and that was one of the things that attracted me to him. He fucked his girlfriend sometimes several times a day, but he was also hypnotized by my boy-fucking stories, so I knew there was potential there for some training. I had no idea that Ben would eventually have one of the most stretched out ruined, assholes we had ever worked on. Especially because he was a kid who was small in stature with a beautiful compact little ass. We could have been satisfied just fucking the hell out of him, and for a while we were, but something compelled me and my buddies to really rip that boy hole to pieces and turn it into a gaping cunt, thus ruining Ben’s entire life, and turning him into nothing but a freakish fuckhole.


It was at least partly his own fault. He had such a cute ass, and the way he wiggled it and tempted and teased with it, it was almost like he was begging us to destroy that boy pussy. Ben loved my erotica, as I said, and wanted some advice on writing. So, I met with him.  I was not interested in teaching him about writing, but only in his teenage mouth and ass pussy. But there was more to it. He had that kind of carefree, fun-loving, self-confidence in a boy that makes you want to break him, train him, and totally fuck him up. Seeing him out with his high school girlfriend, and knowing that he was fucking her, made me want to turn him into a pathetic faggot creature who would never fuck a cunt again.


Drugs and booze and partying helped of course. My buddies pretended to respect him and accept him, even though he was so much younger than we were.

We told him how mature he was, and when we got him drunk or high, we began to rub his cute ass globes, or slid our hands under his tee shirt and tweak his nipples. I finally got him to pose for a naked photo for me… one with his guitar. He has some fucked up dreams of being a musician like many kids his age do.


Well, once we had a naked photo of him, he was ours. What would happen to his family and his future if that photo go out? What if it went to every boy and girl at his school? Well, that would never happen, as long as Ben did a few things for us…like sucked our dicks, and let us shove our big wet cocks up his tender little teen ass. The kid was pretty stupid, or he would have known from my stories that he read that this was a distinct possibility. That is why I felt that deep inside, this is what he wanted. He did not want to become a teenager with an asshole stretched so huge that he could no longer every control his bowel movements. That, I admit, just kind of happened. Ben was like a drug to us. Once we started on him, we just could not stop.


He begged me over and over not to turn him into a fuck hole, and sobbed, which of course only turned me on more. There is nothing like watching a cute, healthy teenage boy fall apart. It started with just me fucking him, telling him it would all be okay, and soon he could go back to his old life. I made him drop his girlfriend, because as far as I was concerned he would never have his dick in a cunt again. He learned to accept sucking my big wet prick and taking it up his ass.

Some days I would just show up at his school and even fuck him between classes. He never knew when might have to suck cock. I often sent him stumbling off to class with a horrible pain in his asshole and cum running down his legs.


And then, I let him know that he would also have to let my friend and colleague C.J. fuck him. And a few weeks later my buddies Luke and Chris.

So now there were four of us regularly fucking this formerly innocent teenage boy.  He became a nervous wreck. We were taking turns fucking him twice a day…that was eight times a day he had to take large peckers up his boy rectum.

He tried to refuse, but he was becoming terribly submissive and the slightest threats would get him back in line. Then I added my buddies Nathan and Max to the mix, so six of us were regularly using his boy hole and turning it into a cunt.

He begged us to let him rest, to let his sore asshole heal for at least a few days, but by now, I had this obsession of wanting to see him continually fucked. I wanted to see this cute teenage boy fucked all day and all night, every day.

We would meet at my friends’ apartment after school and fuck Ben until ten o’clock at night. He told his parents he had join a drama club.


I had my friends invite their friends, and soon guys were lined up outside the bedroom waiting for their turn up his ass. We were stuffing him in both his mouth and asshole at the same time now, also making him clean off the dicks that had spent up his ass with his mouth. He kept crying that he just couldn’t take any more, which made us only want to increase the number .


When we finished with him for the night, he could hardly walk, and the cum just poured out of his asshole…we made him lick it up.


The idea of actually actively stretching his asshole happened when one day C.J .and I decided to double penetrate his teenage hole. The first time, it was so painful for him, he passed out twice. Chris slapped his face with his dick and pissed on it a little to revive him, so he would not miss any of the fun.


After that, double dicking his hole became a regular thing. Someone, I don’t recall who, suggested that when the boy went home at night, he should sleep with a large dildo up his cunt to keep it nice and open for us. This graduated to making him keep a large dildo up his no longer tight ass during the day at school.

He had to drop out of the school sports program, because he was pretty much in constant rectal pain. His hole gaped permanently, the ass ring stretched now to the point of tearing some of the muscles. He began to worry about losing his shit.

I comforted him by telling that that would not happen unless the inner ass ring was also ruined, and we had not gotten that far yet. The kid was like a zombie, like the walking dead in our control.


We wanted to get him out of his home, so as soon as he graduated, we had him move in with us, and that way, we would work on him 24/7.  It was around this time, that I think he began to realize that he would never go to college, that he would cut off communication with his family, and become pretty much, just a faggot fuck hole. We kept him naked and taught him to crawl around the apartment instead of walk.  He ate his meals out of a dog dish on the floor, and the contents of the dish became dog food, with our cum splattered on top. A second bowl filled with our piss was for him to drink.


We had him cut off ties with any of his contacts, and wrote a nice nasty faggot break-up letter to his family, sending them a photo of him sucking dick and taking it up the ass. I’m sure it broke his mom’s heart.


To keep stretching his young ass, remember his body was quite small, as you will see from the photos, we put him on a fucking machine, and increased the size of the rubber dicks fucking him to thirteen inches. Eight hours on such a machine would turn him pretty much mindless.


He went hysterical when we informed him that it was time to teach him how to endure fist-fucking. By now, Ben hardly spoke anymore. He was descending into being a kind of fuck animal, and this was a boy who six months before had gotten decent grades in school and had hopes of a bright future.


As we opened his ass with our hands, our other games became more sadistic. I am not sure why. Something about his sweet nature, just made us want to ruin him. When the Great Dane of one of my buddies sadly died, my buddy castrated the dead beast, and we made Ben eat the dog’s dick and balls.  We used cattle prods and tasers when Ben was reluctant to comply. Sometimes, just for fun, we’d shove a cattle prod up his asshole and turn it on to zap him.

Ben was not getting fist fucked four or five times a day, with really muscular dudes shoving their whole arms up inside the kid. There was nothing he could nto take…long, thick loaves of French bread, bottles, a rolling pin, a baseball bat. He would scream bloody murder and blubber that he could not take any more, and I would tell him that we had faith in him, and that he could take more. He had to trust us, we knew what was best for him.


Two fists went up him, then two baseball bats. The fun of course, was watching him struggle in extreme pain to accommodate whatever we decided to use on his poor wrecked teenage ass. It was at this time that we also started making him have sex with dogs. Not only sucking and getting fucked by three or four dogs in a row, but also drinking dog piss and eating dog shit. I’ll never forget him on the ground, his eyes red and his cute nose running looking up at me with his mouth ringed with a coating of foul brown dog shit, and me telling him what a good boy he was and how proud I was of him. He began to live for those compliments. “Good boy, Ben, you sucked those doggie balls real good, now lick up all the spilled dog jizz.”  Of course, we also introduced him to eating human waste, and for some time, he became our total toilet. When he could no longer  control his own bowels because of his ruined rectum, and he would now and then defecate on the floor, we made him eat it to teach him to not be a messy boy.


Eventually we became bored with him. He no longer responded much to electric shock, his nipples had been stretched beyond belief, He had trouble getting an erection, he whimpered and moaned all the time, and I knew it was time to get rid of him. Fortunately, I knew of a ranch near Cancun, Mexicao where they did boy/animal sex shows and boys got fucked by horses. Ben’s hole by now could easily take a horse dick, and it had become an ugly thing to look at.

He had lost his sweet, boyish, youthful charm. He was a fucking mess, so a friend of mine took him down to the Mexican ranch and sold him.


Because I was always fond of Ben, I did go to visit him. He was quite a star, doing three shows a day in which he could suck a large stallion’s balls and asshole and dick and then take the almost twenty inch prick up his mess of a boy cunt. After the horse came, the sperm would pour out of Ben’s ass and he would lick it up. He was a big hit with the crowd. So you see, some stories like this do have a happy ending.

Submitted: May 21, 2023

© Copyright 2023 dale10. All rights reserved.

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Add Your Comments:



What a beautiful story!

Sun, May 21st, 2023 11:45am

svartur fugl

I'm so envious of Ben. He was lucky to find his proper place in this world. Wish I had happened across the author when I was at high school.

Sun, May 21st, 2023 6:04pm

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