Sean's Dilemma

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

Featured Review on this writing by jeremysfaggot

This is an extreme story of an 18 year old who leaves home and falls into the clutches of an perverted writer or erotica, who forces the young man to live a life of filth and degeneration.

Sean’s Dilemma by dale10



This work is Copyrighted to the author. All people and events in this story are entirely fictitious.

All characters are over 18 years of age. The author does not condone any of the activities in this story. Warning: this story is quite extreme and contains toilet humiliation.



 I have not been forthcoming with you about my continuing escapade with the boy Sean with whom I had been working for some time. That is because events moved very rapidly. Remember he first contacted me saying he was a senior in high school and had an unnatural interest in dominance and submission and the kind of sex I describe in my stories.  I saw an opportunity to develop my relationship with the teenage cunt in a much faster timeframe than previously planned. Ruining his reputation at school, getting him in trouble at home, getting him to try drugs, masturbate with other jocks and to eventually suck dick and other things, all led to him making an important decision in his life. He decided to quit school, not graduate and to run away from home and his very strict conservative parents. The ultimate test for him was for him to video sucking his drunk sleeping father’s dick. Once he’d done that, I knew I had him. I had some friends of mine in his area provide him with drugs, as I don’t directy deal with drugs, but once he used and then sold, he would go to prison if caught and charged…and of course I had proof. So, he was pretty fucked up. Ultimately, he ran away.  I was kind enough to offer him temporary shelter and some further guidance into his future life.

Sean is a really cute boy, the kind any sane pervert would pay well to fuck. He is athletic of build but small of stature and looks younger than his 18 years.  So he came to live with me. Of course, young, cute Sean had to find a way to earn a living and pay for his upkeep. He also had developed by now an expensive drug problem, and that needed to be paid for. The following is a conversation between myself and Sean that took place a few weeks ago. (This is a reconstruction of the chat...not a literal transcript.)

Sean is seated across from me in an arm chair. He is bare assed naked of course. He is sitting, as he has been taught, with his legs spread and up and over the arms of the chair, so that I have a  totally clear view of his nice heavy, fat cock, his big teen balls and his darling puckered asshole. I have taken all of Sean's clothing, and he is required to be naked when at home at all times. When he goes out working, (looking for dick) he wears clothing that I provide for him. This can be something as skimpy as gym shorts, flip flops, and a tank top, or no top at all. Eventually he might even be required to wear a sixth grade girls cheerleader skirt with no panties underneath.

Sean: I feel stupid going around the malls wearing these tiny gym shorts. Everybody stares at me like I was a retard. The whole shape of my dick and balls shows, and in the back it rides up my crack. They are so small that about two inches of ass crack show in back and my pubic bush shows in front.

Dale: They help you with your work. They help to attract the right sort of gentlemen. Perhaps we can shave off your pubic bush, and that will solve that problem.  Sean, I pay for your food and give you sleeping quarters. I also pay for two Viagra a day for you, and help you pay for your nasty little habits of drugs and booze that you have developed. You have no home, and I was nice enough to take you in. You are also wanted by the police for three separate drug incidents. (which I helped orchestrate) You should be grateful.

Sean: I am grateful. It's just that it's not how I thought it would be when I left home. I thought somehow it would be, I don't know. I’m so unhappy. I’m so depressed.

Dale: This is not some dream world, Sean, this is reality. You wanted to be sexually dominated and trained when you wrote to me. You expressed a desire to experience all of this. I took a risk with you, and now you have to deal with it. I want to go over the rules of the house with you. Spread your legs wider apart Sean whenever you sit. From now on I want your legs and ass totally shaved of all hair each day. I don’t want to find a single hair around that puckered pink hole. Now, I want to see you jerk your dick and play with your asshole while I talk to you. (He does this with some shame and shyness. It is so beautiful seeing a humiliated 18 year old boy behaving in this filthy manner.) Get a couple of fingers up your asshole. Sean. Show me some enthusiasm. Get them way up there.  I have let you pretty much just kick back and take it easy until now, but now you have to earn your keep. First of all, I expect you to clean the house, top to bottom. Since I expect a totally germ fee, spotless bathroom, you will clean that with your toothbrush, so you can get in every nook and cranny. If I find even a spot on or in the toilet, your allowance will be withheld and you will be punished.

Sean: You want me to use my toothbrush... that I brush my teeth with?

Dale: If you keep the bathroom clean, there should be no problem... then the toothbrush will also be clean enough to use on your teeth. I will also from time to time have you insert the toothbrush up your ass, to ensure that your hole is totally clean as well. You will brush your teeth directly after.  I feel that corporal punishment is in order for boys who do not do an adequate job. For any mistakes you make in following the house rules, you will be punished with swats from a cane on your bare ass globes or on your balls or your asshole itself. We will also use a taser and electro-torture punishment from time to time, but only for extreme punishment in the case of really bad behavior. Pins, needles, tacks, and other household implements will also be used in your punishments. I do not enjoy punishing you, Sean, you know I really care for you, but if you are going to live here, you need to learn to follow rules. You will dust the house thoroughly every day. You will dust the house by taping a feather duster to your hard dick and dusting things that way. You will be watched and punished if the work is not good enough. You will not use your hands when you dust.  We may also stick a second feather duster up your ass. Whenever I have guests in the house, you will not walk, but you will crawl on hands and knees. When you do, make sure your legs are far apart so we can see your nice full teenage scrotum swing. Also, make sure your back is arched so your ass is high. When you crawl, you should also have your tongue hanging out of your mouth. Any infractions will be severely punished. Now on to your daily diet. I am putting you on a special diet to help get you in shape. This diet consists of dry dog food. Because I want you to have some choice and some say in the decisions we make together, I will allow you to choose which brand of dry dog food you wish to eat. You can only pick one, as we can save money by buying a large bag.

Sean: I have to eat dog food? (You ought to see the look on his cute face. Fucking pathetic)

Dale: For now. To save money and also for your special diet. If you do a good job, the diet can improve.  I am providing you with a special bowl to eat out of. This is Sean's bowl. It is an extra- large doggie bowl. You see, your name is on it. Isn’t that nice?  You will use the bowl in two ways. You will eat all your meals out of the bowl. You will also use the bowl as your toilet.

Sean: Huh? What?

Dale: You will squat over the bowl and piss and shit in it.  Then, when given permission,  you will empty and clean it. You will make sure it is very clean because it is also the bowl out of which you will eat your meals. This will teach you to be clean and tidy.  At my meal time, I will also feed you table scraps, but I will probably put these in your bowl as a special treat. I will also, to add variety to your food, chew and spit some of my food into your bowl for you to eat.  Most of your meals will be dog food moistened with a bit of my piss.

Sean: That's sick. That is really sick!!!!!

Dale: That is not for you to decide. Sean, you ran away from home. Everybody back home knows you are a fucking dirty law breaking faggot. If you are caught, you will be sent to prison.

Dale:  You also have developed a bit of a drug habit. You are hooked. You need your daily drugs or you will lose your mind. You need my help. You have no place else to turn. I suggest you start to be grateful. Remember, you are the one who loved my stories and wrote to me and begged me to make them a reality for you. Now, where was I? Oh, yes. You will also not use your bowl to shit or piss unsupervised. Myself or one of my friends must always be there to observe and monitor when you shit or piss.

Sean: You're going to watch me?

Dale: And take photos and videos. You need supervision. You will squat and spread your legs wide over your bowl. When you piss, you will announce loudly, “Pissing, Sir.” When you shit, you will announce, “Shitting, Sir!” Those who watch you on video will enjoy that. If you are good, we will allow you to wash your bowl after you shit and piss before you eat. If you are bad, you will have to eat your meals out of an unwashed bowl. That is not a very appetizing prospect, so I suggest you comply with good humor and enthusiasm. Now… masturbation. When at home, you will masturbate continually from eight in the morning until ten at night. Myself or my friends will monitor you and we will have cameras on you as well.  You may have a ten-minute break once every four hours to allow your dick to rest. At all other times, you will maintain a full hard on. If your hard on goes down even a fraction, you will be punished. You will be measured by my friends with spot checks. Both the length and the thickness of the dick must be full at all times.  But you will not cum. I hope you understand this. YOU WILL NOT CUM. If you cum without permission, you will be punished in the worst ways imaginable. Cumming without permission is one of the worst crimes you can commit. At least once every half hour, you will bring your dick to the point of leaking pre-fuck. You will deposit this pre-fuck in a container we will provide for you. It may be added to your diet. If you are a good boy and do as you are told, you will be allowed to cum every now and then as a reward. Perhaps once a month or so. I know most boys your age cum three or four times a day, but you will learn discipline.  Do you understand?

Sean: (looking down at the floor, about to cry) Yes. Sir.

Dale: Good boy. Now as to your work.  You will work away from home every other day. You will be expected to suck between fifteen and twenty dicks a day on those days. Because we care about you, we will help you set up hook-ups over the internet and through local channels we have. It will not be difficult to find fifteen or twenty men who want to get sucked off by a cute athletic twink teen each day. You will build up repeat customers. You will suck all ages and all kinds of men. You will have no choice and no right to refuse.  Each man will pay you one dollar for you to suck them. A suck will always include you licking their balls and assholes for them, as you have been taught. A thorough rim job will be part of your service. You will also kiss and lick the dick to show respect and deep throat of course.  Of course, you will be expected to suck more on weekends... twenty-five to thirty dicks a day. This does not count sucking my dick or the dicks of my friends. Do you understand?

Sean: Thirty dicks a day? but that is more than one an hour all day and night. My jaw and tongue will get raw. I can’t swallow that much cum!

Dale: Well you will also need time for your house chores, to take care of me and my friends, and to rest, so, you will have to do three cocks an hour or so... you can probably get it up to five cocks an hour, if you really do a good job and become an excellent cocksucker. And my friend will help get the dudes and we get them lined up properly. One will pull out after he shoots, and the next one can shove his prick in.  It's a matter of getting them in and out and arranging the schedule. We'll help with that too. We like you and want the very best for you. So, you should be able to do your daily dick sucking quota in five or six hours if you really work at it. That leaves plenty of time for your ass fucks.

Sean: My ass fucks?

Dale: Yes, I expect you to get ass fucked at least five to eight times a day on the days you are working. That of course does not include me fucking you or my friends fucking you which will happen every day.

Sean: My mouth and ass will be raw!

Dale: Only at first. Like most things the human body adapts. Your cunt and mouth will get used to it. Of course, if a client wants something special like a piss or shit session with you, then I will allow more time. I am not unreasonable. Certain dudes may also want s/m sessions with you, and they take more time, so the client can enjoy your pain. You will charge five dollars for a dude to fuck you. The money you make will go toward your room and board and your nasty habits. You will also be posing for web cast shows and private sessions, where fans of yours will be able to request certain activities and you will comply. Men like to watch teenage boys doing really nasty, perverted, filthy things. Your web shows will be on Sat. or Sunday nights. (He is crying hard now. This always makes me really aroused. Something about watching an 18 year old teen trying to be all manly, reduced to little boy tears. )

Sean: What kinds of things will that involve.

Dale:  Do you want a tissue to dry your tears? And keep masturbating your dick and working those fingers in your asshole. You don’t want to make me angry.  Don't be nervous...the special requests are nothing too serious. Mostly stupid stuff like fucking your ass with a banana and then eating it, putting candy up your asshole and then eating the candy. Making yourself vomit and then licking it up. Just mostly things to show what a complete fuck pig you are. Or rather, what a  filthy fuck pig you are becoming. Guys can send in their used condoms with their names on them, and you will suck them out and give a personal message to the dude. Guys can send in dirty jock straps and underpants with piss and shit stains, and you will suck them clean for them during your web show. Dudes will send you Tupperware dishes filled with piss and shit and cum and snot, and you will eat and drink it for them on the web show so they can feel they are interacting with you. They will suggest things they want to see you shove up your ass. They might want to see you do stuff with animals. I have some good friends who will help you learn all about that.

Sean: You are really going to make me do this sick stuff? (crying uncontrollably now.) I can’t. I just can’t!

Dale: Sean, right now, you don't have any other option except going to prison. So, I think you should be grateful. You'll get used to your life here. You have no future, Sean, except by doing what we say. Later on, when you and your clients gets used to the routine, we will spice things up a bit with tattoos and piercings. We had one cute teen last year, just your age, with COCKSUCKER tattooed on his forehead. He used to wear his hair over his forehead to cover as much of it as possible.  We will also be doing special workshops at which we help to make your balls hang lower and open up your pisshole, things like that. To make you more attractive.  Of course, you will be entertaining at private parties for me and my friends as well, and those should be lots of fun. You have to get used to toilet games. I know that still repulses you somewhat, but I am going to help you. It is essential that you are able to ingest both human and animal waste. We will mix some shit in with your dog food to help you slowly get used to the taste. You'll be amazed how soon you get used to the taste. Pretty soon you won't be sick at all by eating turds right out of dude's assholes. I know certain men who think there is no thrill better than squatting over the face of a young cute boy. A boy can get used to almost anything with the proper training. Part of the fun is to take something shocking or repulsive or humiliating or disgusting, and then make you adapt to it and get used to it until it no longer freaks you out at all. Then move on to something even more revolting.  I promise you Sean, soon you'll be eating dog shit off the street and thinking nothing of it at all. How proud of you we'll be then. You'll get used to the fact that friends of mine will blow their noses and spit into your mouth, and you will happily chow it down. You knew when you wrote to me that corrupting boys is what I live for, and you wanted it. There is no thrill in the world like totally fucking up an eighteen year old boy on the cusp of manhood,  destroying any sense of self-esteem and destroying him mentally and physically.

Sean: What's going to happen to me? What will become of me?

Dale: The thing to do Sean is to try to enjoy this and have fun. If you just relax and take it easy and go with the flow and do as you are told, it can be lots of fun for all of us. After a couple of years, we will re-assess your position, probably tire of you and throw you out on the streets.  Because I can't always devote the time to you that I would like, you will mostly be staying ometimes with friends of mine. They are good men who know how to train a boy properly. They are harsh and strict and very kinky, but also can be loving. They are experts at fist fucking a boy, and will help you with that.

Sean: Fist fucking?

Dale: Don't be scared. They have successfully fisted boys your age many times, so you will provide no problem. First single, then double fisting. The trouble with fisting is not the actually fist fucking itself. It is in getting a boy to do the proper exercises after, to get his asshole muscles to work to tighten up the cunthole again. Otherwise the boy becomes a useless loose fuck who can’t control his own bowls, and who wants that?

Sean: Don't I have any say in what happens to me? (He is almost hysterical. I love it.)

Dale: No. You mentioned before what you thought of, as an unattractive skimpy mall outfit we made you wear. We will often entertain ourselves by making you go out in public in various costumes. We may want you to wear a tee shirt bearing the logo "I SUCK COCK!" or perhaps we'll take you through the drive-thru of a fast food restaurant totally bare assed naked in the car, playing with your dick and we will cum on the burger we buy you. We like to have fun, and you should relax and become part of that fun. Sometimes at the mall or health club or swimming pool, you will be given assignments like, "You have thirty minutes to get ass fucked!" Your job will be to go and pick up some dude and accomplish the task. This can be a fun and exciting challenge. We may turn you loose in the toilet of a mall and say, “You need to suck ten dicks in the next two hours." In these cases, your costume will surly help as it will attract clientele. It will also give you the thrills you sought when you first wrote to me asking me about being made to feel humiliated and degraded. I intend to help you out, Sean by keeping you totally degraded as much as is humanly possible. I am going to make your teenage wish come true. You will be laughed at, made fun of, spit on, called names, beaten up, abused, molested and tortured. Your ever wish made a reality. And all because you wrote to me less than a year ago. Just think how far you have come. You have dropped out of school. Been mouth and ass fucked. Actually sucked your drunken dad's dick when he was passed out. Run away from home. Everyone back home knows you are a fucking homo perv. I’ve sent photos of you to all your schoolmates and to your parents and to the priest at your church. You are now starting a new life as a fuckpig. How proud I am of you and how proud you should be. Can you get more fingers up your asshole for me, please?

Sean: Can I have some pills please. I feel nervous and sick.

Dale: You can have a little something right after we film you shoving that plastic water bottle up your ass for us. Put on your best smile, Sean, you have lots of fans.

Submitted: December 26, 2021

© Copyright 2023 dale10. All rights reserved.

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Can't wait for a followup chapter on this one! EXCELLENT!

Wed, January 5th, 2022 12:43pm

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