Sean's Dilemma Part Two

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

A few weeks into Sean's training, the author reviews his work and informs the boy of his punishment. He forces the boy lower and lower, turning him into some kind of sexslave animal.

Sean’s Dilemma Part Twoby  dale10


  This story is fiction. All characters are 18 yrs of age or older. The author does not condone any of the activities conducted in the story, and it is for fantasy purposes only.


Dale10’s novels “Agitato” and “Debauched Genius” written under the name D.H. Gutzman may be purchased from amazon.


Part Two:  Punishment


I want to thank those of you who have taken such a direct interest in my work with eighteen-year old high school drop-out Sean. It warms my heart to learn that there are so many folks out there who care about the future development and training of a boy like him. A few of you, very few, felt that my rules and discipline for Sean were too harsh and severe. But most of you understood that to totally break and destroy a healthy, athletic eighteen-year old boy takes extreme measures. You must also understand that I am working with a boy who has a bad drug habit and who is wanted by the police. (I confess that I orchestrated most of that.)


Sean tried hard to adapt to the many new demands made upon him. I knew that I had piled too many new rules and tasks on him for him to accomplish, and this was intentional, as for each rule he broke or task he didn’t complete, he would be punished. There are very few things I enjoy in life as much as punishing a teenage boy. Of course, he must be well built and beautiful. An innocent face helps. I like my boys on the slender side, tight young tummies, well-formed, but  not overly developed pecs, tight round asses, strong legs, feet with nice arches, and so on. I also appreciate a full fat teenage dick and nice loose large balls. Boys who come from conservative and religious family backgrounds are also quite appealing, as there is so much more to destroy. To turn such a boy into a dirty, filthy, fuck animal is a real accomplishment I’m sure some of you have tried it with boys in your lives, perhaps even one of your own children. My heart was filled with joy at some letters I received upon publishing the first part of this story, from  dads who had taken such discipline and sexual control measures with their own teenage sons.


One friendly dad wrote to me to say he makes his son watch porno for four hours each night, making the boy play with his dick while he watches but not cum.

The boy has not cum for over a year. He is caged to go to school. The creative dad has not ever allowed his son to go on a single date or mix with girls. Just watch porn. I am fascinated with what this may do to the mind of an eighteen-year old, and I may visit the guy just to meet the fucked-up son. The father taunts the kid by saying that if he obeys every command, he may be allowed to date girls when he is twenty-one. Then again, of course, he may not! The boy is also fucked nightly with dildos of increasing sizes. The dad sent me some lovely photos. The boy is really cute, and especially appealing when he is in pain.


Another interested reader wrote to me that a teenage boy named Jason had fucked his daughter pregnant. The poor girl had a kind of nervous breakdown, and Dad who is quite conservative and religious had the boy arrested. Now, the cool thing is, the girl’s father works in the corrections department for the state, and he made sure the judge threw the book at the 18 year old fucker. He was sent to a severe detention facility and put into a block with rapists of the most violent kind.

The boy, who was a rather short, slender blond kid, was mouth and ass raped by the guys in the block non-stop from his first hour there. He became the cell block pussy and even toilet. Some of the inmates stopped taking showers and made the boy lick their bodies clean! He had cock in him from both ends for hours on end each day. I applauded the inventiveness of the dad, and told him I hoped his daughter would come out of the trauma ok, and that the boy would be punished even more seriously. He told me he was arranging with some of the inmates to tattoo “COCKSUCKER” and “FAGGOT” on the boy’s face and chest. He was also making sure the boy broke some rules, so that his incarceration time would be increased.


I shared each of the many responses I got with Sean, hoping he would feel proud to be the inspiration for such communications. I’m afraid Sean has not adjusted properly to his new role in life. He has become sullen and depressed, both of which make him look very cute. He know he needs the drugs he takes, and that I am his only source. (I do not deal in drugs, but have acquaintances administer to his needs in that area.) since my last communication with you, Sean has  lost some weight, which is fine with me as I love slender boys, and has also lost much of his energy, which is not good for his cocksucking and ass fuck duties. Because his face is thinner now, his constantly frightened eyes look larger. He has developed a slight tremor in his hands due to the anxiety of having to meet his daily chore requirements. He now stands before me naked for his weekly punishment session. His full lower cocksucker lip trembles. Tears already cloud his eyes, and we haven’t even started yet. He knows these sessions never end very well for him. However in spite of the pain he may have to endure, what he fears most is me withholding his drugs. The drugs are the only thing that keep his young fragile mind from totally cracking.


With his body now thinner, his big fat teenage dick looks even larger. I was lucky this time to get a boy with a really beautifully full thick hunk of fuckmeat.

He keeps it erect at all times as ordered, with only a few breaks during the day.

The dick looks red and angry and the pisshole bubbles pre-fuck, teen boys are often such wonderful leakers. He has not cum since m last missive to you, as that would be the ultimate infraction of the rules, so he is edging constantly and spends most of the day in extreme sexual agony. His balls hand low in the sack, but now and then as he approaches an unwanted orgasm, they draw up under the dick. I taught him the trick of slapping his own nuts really hard to dispel the impending cum. He is monitored constantly to see he does not secretly try to unload his needy nuts. How, you ask, can a teenage boy live in constant sexual need and agony?  How indeed. That is half the fun.


About a week back, the boy seemed to stop being on a tormenting constant sexual edge. He seemed to be coping with the throb and leak and strain and fuck need. I h ad to up the game a bit. So I took to lightly sandpapering Sean’s dickhead to increase its sensitivity. Sandpapering especially around the pisshole, makes him almost orgasm each time he pisses or even lightly rubs his dickhead.

So it is not unusual to see the boy tighten his gut and buck his hips every now and then in an incontrollable sexual pulse. Five or six times a day, he will break down and plead with me to allow him to cum. He says it is driving him mad, and I believe it. I don’t mind if he loses his mind, as long as he can continue to suffer. I don’t want him to lose that capacity. My friends and I will stroke him for hours, until our hands are coated with dick pre-fuck slime, which he then licks clean for us. He now stands ready for our punishment session.


Dale: Sean, are you ready for your weekly punishment session?


Sean: Please, Sir… I tried to do good this week.

Dale:  Just because you are a fucked-up piece of shit, Sean, that is no reason for you to misuse grammar. You may say you tried to do well, or you tried to do a good job, not you tried to do good.


Sean: Please, Sir, don’t hurt me.


Dale: Sean, you know that when we hurt you or make demands on you that seem disgusting, filthy, perverted or unreasonable, it is for your own good. We have gone way beyond the stage of arguing with you whether you must or must not do what we say. Stand up straight, Sean, your shoulders are slumping. I see your hard dick is twitching just a bit, does that mean it is losing some of its erection?


Sean: No Sir! It’s just that when I get scared my dick starts to lose some of its power.


Dale: You know, Sean, there are some men and boys who actually get harder dicks when they feel pain or are punished. Maybe we need to help you to become one of those boys. Make sure you try to stay hard during your punishments. Now let’s look at your list of demerits this week.


First: On Monday, a stray hair was found growing out of the left side of your asshole. You know you are to keep your asshole area absolutely free of hair and you are to pluck it every morning.  Many of the men who fuck you want the boy’s asshole to look as smooth and pink as a baby’s pussy. To that end, we will also bleach your asshole so it stays nice and pink and bright. For that stray asshole hair, you will be punished. Your balls and legs and other parts of your body have been kept nicely shaved and plucked. So, you are doing better, Sean. I remember just a few weeks ago when one of the gentlemen who was fucking you saw several unsightly ball sack hairs.  Still one asshole hair is one too many. Wipe that drop of pre-fuck off the tip of your dick, Sean and lick it up.


Second: You have been having trouble eating your meals lately. You actually complained that you couldn’t stand the little bits of shit mixed in with your dog food diet. You actually vomited several times. Of course we made you lick it up, but still, it is quite rude to treat our kindness that way.


Sean:  I try, Sir, I really do. But sometimes the taste of shit still makes me sick, especially mixed with my food. (He starts to cry) I ate the shit out of your ass this week and didn’t get sick or complain.


Dale: Sean, what a fucking stupid thing to say. Of course you ate my shit without complaint. That is your job. You are a fucking toilet. But that does not excuse you gagging and getting sick over your meals. We spend good money on high grade dry dog food for you, and mix shit in so you will get used to the flavor. We are bending over backwards to help you adjust. For the next week, you meals will consist off nothing but vitamins to keep you healthy, and bowls of fresh shit mixed with human vomit. My assistants will take turns puking into your bowl.

You will learn to eat whatever we say without complaint. Do you understand?


Sean: (really crying hard now.)  Yes, Sir. I will try. (he is very very defeated)


Dale: You will not try, you will succeed! Nothing less than excellence will be accepted. If you are a good boy, some of us will jerk off into your food bowl for dessert.


Sean: I am so sorry sir, sometimes I just don’t think I can stand it anymore.


Dale: Nonsense, Sean, we are just getting started. We haven’t even scratched the surface yet of the things we are going to do to you. You just need to learn to accept it and not think for yourself. Just do as ordered. Now,


Third:  On Wednesday, when sucking off your eighteenth dick, you gagged and spit up some pre-fuck and puke onto the ground. You licked it up at once, but it was too late. You showed disrespect to the gentleman’s dick. He was highly offended. He expected, enthusiastic eighteen-year old teen to gleefully suck his cock, and instead he got a sullen, recalcitrant, boy who gagged and spit up! Think of how that reflected on me and my work!


Sean: So many of the men that day had such big loads, my stomach just couldn’t handle all the cum, and I got sick.


Dale:  We shall have to extend your stomach’s capacity for cum. I am scheduling you for several stomach-filling and pumping sessions. At the same time, we will expand your enema-tolerance level. We will fill you with soap water until you looknine months pregnant and then make you hold it for over an hour. Five or six sessions a day for ten days should help you. If you leak even a drop of water, we will add two extra sessions per day.


Fourth: On Thursday, while you were being ass fucked, you made an ungrateful sound, as if you were in pain.


Sean: Oh, Sir, he was so big. It was like he was deformed or something. He had a dick over a foot long and these large bumps on it. I couldn’t help it. Please try to understand.


Dale: I do understand, Sean, believe me. I sympathize. Sometimes in our work, we encounter situations that are less than pleasant…certain special problems that we have to work with. You need to learn to adapt. That gentleman was a bit of a sexual freak, I grant you, but does that mean he should not have the best possible experience? In Victorian time, rent boys in London, some of them quite young, frequently had to suck extremely diseased dicks.  Venereal disease ran rampant in those days. Boys had to suck puss and open sores and all kind of nasty things. Think how lucky you are, Sean. If a big, slightly malformed cock hurts you so much, it simply means your anal canal needs to be stretched. How else do you ever expect to be a suitable lover while being double fist-fucked? By the way, I sent a photo of you sucking that huge deformed dick to your mom. I thought she might enjoy seeing her son at his new career.


Sean: Oh God, no please! I don’t want her to see me this way! PLEASE! 


Dale: Too late, Cunt Face, it’s already done. Poor woman probably had a heart attack. Oh well.  What if I sent your mom and dad the selfie I had you take of you  sucking your drunken, sleeping dad’s dick? We haven’t shared that with them yet.

That might even ruin their marriage.


Sean: You made me do that. I didn’t want to.


Dale: Back in those days, Sean, before you were an addicted druggie, you still had some free choice. Now, I’m afraid you are my fuck toy.


Fifth:  You complained and cried over the nice outfit we had you wear to the mall to suck dick on Friday.


Sean: How could you expect me to go in public dressed like that? I would be arrested and then because of the drug charges put in jail.


Dale: You must learn that it is not your decision to make. You will dress as we tell you to, and act as we tell you to. You will shit, piss, eat, sleep and live by our orders. What is wrong with a see-through mesh thong and a crop top tee shirt saying, “I SUCK COCK.”  There are no laws about what can be printed on a tee shirt, and you were covered by the thong. Yes, the flesh of your dick could be seen through the mesh, but it was still covered. But you actually fought with us over that. For that you will receive a very serious punishment. On your next public work day, you will also dress as follows, a short skirt with no panties or undergarments beneath. The hem of the skirt will fall no lower than half an inch below your ball sack. You will wear a female bikini top. On your legs, fish-net stockings and a garter belt. You will wear four inch spiked heels.

(At this  news, poor Sean fell to his knees sobbing uncontrollably and trembling”


Get up you pathetic piece of shit. I told you to stand at attention! And by God, your useless dick has lost its hardon! I warned you about that. You fucking loser, now your punishment will be so severe, I swear you will never forget it.

(He climbs back to his standing position and masturbates his penis, but has difficulty getting it hard.)


 If your dick is that fucking useless, perhaps we should just have it surgically removed. After all, you can still suck dick and take it up the ass with no cock.

I have never seen a boy of eighteen so pathetic. (I tossed him a ten-inch pink rubber dildo) Here shove this up your asshole. It might help you get hard and stay that way. (he stared at it as if it were an alien object from another planet. It was as thick as a beer can and quite imposing.) 


Well, don’t just stand there like a fucking twerp, lift one leg and work that dildo up your fucked pussy hole of an ass. (it was amusing watching him trying to gain a stance which would allow him to insert the thick rubber dick up his round young teenage ass. He spread his legs and raised one foot but could not get enough purchase to open his cheeks enough to shove the dildo into the asshole. The then spread his legs wide, bent over and tried to push the dildo in that way. He grew more and more frantic and more and more beautiful in his fear and anxiety. His young sinewy muscles strained. He began to pound the plumb sized rubber dick head at his rosebud, so eager to please me that he no longer cared if he hurt himself. I liked that attitude. His hairless ball sack swung, and his half hard dick bobbed. He grunted and groaned and gritted his teeth and pushed the thick dildo at his asshole.)


Jesus Christ you are useless. All right put the dildo on the floor and sit on it! Go on, squat over it and then sit down, shoving it all the way in!


 (Remember, it was ten inches. In the future, he would learn to take far larger ones up his boy hole. Twelve, thirteen, fourteen, fifteen inches. He would stuff his hole until he blacked out from the pain, and we had to piss on his face to wake him up. But ten was enough for today. He had trouble with the last four or five inches, so I walked over and pressed on his young smooth shoulders to forced more rubber dick up into him. He at last sat down flat on the floor, stuffed with dildo. He looked hysterically funny, sitting with his legs spread, feet out, the dildo forced up into his teen guts. His eyes were blurry and unfocused. His damp hair plastered to his forehead. God, how pretty.  And we hadn’t even started his punishment yet!)  

Submitted: January 18, 2022

© Copyright 2023 dale10. All rights reserved.

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