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

As Teddy is degraded even more because of his small penis, his body is violated and abused.

Teddy’s Humiliation Part Eleven by dale10



(The following story is fiction and fantasy. The author does not condone any of the activities in the story. All characters are 18 years of age or older.

To may purchase dale10’s novels “AGITATO” AND “DEBAUCHED GENIUS”

On Amazon. He writes there under the name D.H. Gutzman )



Teddy’s eighteen-year old asshole would never be the same. We had him on the Fucking Machine for almost a week straight. The dildo’s pumping in and out of his cute young ass became larger and larger in both length and girth. I kept reminding him that since his dick was so uselessly small, we had to help him find anal or what we professionally called “cuntal” pleasure. Oh, he sobbed of course and screamed himself hoarse that his asshole was not a cunt, and I gently reminded him that he had been created with a dick that was more of a clit, and so his asshole inside was really more of a cunt. He was a freak of nature. The hormones we had been injecting him with had made his nipples so sensitive he could no longer even touch them. So of course, I worked on them constantly, until he screamed himself hoarse, and the nipple nubs stood out over and inch from his pecs.


You realize by n ow, in order to get him to submit to all of this, I had had to seriously fuck with his mind. That had been the purpose of those first easy humiliation games to which I had exposed him. By now, his head was fucked and he pretty much went along with whatever my perverted friends and I wanted.  However, I didn’t want him so fucked up that he no longer felt the humiliation and degradation. I had to carefully calibrate his decline, so that he always felt more and more shame.


And that is the reason I wanted him fucked by his own father. You can imagine how both father and son felt about this. It is certainly one thing if Dad is a pervert and wants to shove his thick dick into his teenage son’s asshole, or the teenager is a fucking pervert and wants Daddy’s dick in his mouth and hole. But that’s not fun. How much more exciting to make a daddy who is appalled and disgusted by the idea, force his fat fucker into the asshole of his basically unwilling son.


With the drugs I had given both and some hypnotism and the general nature of their mixed up concerns, I had both of them ready. Dad had been brain fucked

Into believing that if he fucked his son, the boy might be sexually and mentally helped.


Teddy stood naked in the middle of the room. He had a tiny pink bow tied around his little dick. I was streaming the event for my many subscribers. Teddy’s eyes were kind of dead, and I had to get some life into him. I slapped his pretty ass and ordered him to put one foot up on a chair. The move made his balls jiggle and his ass open up a bit. I put my four fingers and thumb together and lifted them to show the cameras, and then I forced all five up into Teddy’s stretched asshole. The boy gasped and whimpered a bit but did not move. I roughly worked the fingers up into his stretched asshole. Way up…way in…until his mouth opened in frantic gasps. I was not quite fist fucking him, but pretty close. The fucking machine dildos had really obscenely stretched that shithole. Of course, it wasn’t opened near enough yet to satisfy me I wanted him to be able to take two giant hands up his hole at the same time. I wanted him so anally ruined, that he would no longer be able to control his bowels. Imagine how humiliating that would be for the poor eighteen-year old.


“Ahhh… please, no!”  Teddy moaned as I worked my hand around in his hole.


“Shut the fuck up, Faggot!” My tone toward him was also changing. I was no longer playing the caring, loving, doctor or the partying fun-loving dude who had first kiddingly gotten him to show his tiny dick to my friends. I could not actually abuse Teddy openly.


Just a few days before, I had taken Teddy out in public dressed as a cunt. This had really damaged his fragile mind. I had forced him to wear mesh stockings with a garter belt, six-inch high heels, A really short cheerleading skirt which came down to only half an inch below his ball sack. No panties of course. On top, he wore a mesh bikini top, so that his roughed sore extended nipples showed through. We smeared lipstick on his mouth and rouge on his cheeks.


And then I had gone one step further, which had really totally freaked him out. He actually sobbed so hard, he fainted. I pierced his nose and attached a large ring. He looked so pathetic, like a circus side show freak. I did not take him to gay bars or grunge bars dressed like this. Oh no, I took him to conservative places, so everyone could stare at the fucking freak!  I took him to fast food places, crowded with teenage boys and girls and made him sit with his legs spread wide, so the skirt rode up and Teddy’s tiny prick and teen balls were on display.

I took him to malls and parks.


I was not finished decorating Teddy. Oh no, not by a long shot. After his dad fucked him, I would take him to a friend I have who would put rings through the boy’s nipples and through his ball sack and tiny dickhead. I explained this to Teddy in great detail, while he trembled and moaned.


“I want you to feel a part of the therapy we are doing with you to help you adjust to yourself. So, I want you to have some input. Tell me, Teddy, which tattoo would you prefer to have across your chest in five-inch high letters, FAGGOT COCKSUCKER, or DADDY’S FUCKBOY, which do you prefer?


Teddy would hang his head in shame, and to keep him alert, I would lift it by the chin and spit all over his cute young face. I loved the way his lips trembled.

“You know, Teddy, you have such cute full cocksucker lips, you really need to start sucking some dick regularly. I think after you suck your daddy’s dick to get it ready to fuck your boy ass, I will start a regular routine for you. Something like having you suck ten to fifteen dicks minimum each day.”  His big eyes that had been so bright when he was one of the most popular kids at his school and were now dull  and clouded grew even larger.


“I know you have been kicked out of your school for good and will not graduate, but I think it would be good for your mental stability if you sucked some of the cocks of your former jock schoolmates. I am trying to work this out with your former high school varsity football team. It’s not easy because some of the healthy normal boys don’t want to let a fucking freak’s mouth near their girl fucking dicks, but when I pointed out how you had disgraced the school, they began to come around. They are signing up fellow school jocks now to have a good mouth fucking session with you. There are twenty names on the list so far.”

I grabbed a handful of his hair and jerked his head back further. “Remember, we are doing this for you. For your own good. You have to accept that you are a fucking perverted tiny dicked freak piece of shit. Am I correct?”


“Yes, Sir,” he mumbled, totally defeated. Such a pathetic boy.


‘I didn’t hear you. Say it louder. Say ‘I am a pathetic faggot tiny dicked freak.” 


“I am a tiny dicked freak!” He sobbed.


“No, no, fuck face! You forgot ‘pathetic faggot!’”  


Spit ran from his mouth and dripped from his chin. His nose ran. “I AM A PATHETIC FAGGOT TINY DICKED FREAK!” he screamed.


“That’s a good boy. The more you accept that, the happier you will eventually be. Look at how nice your titties are coming along. Your nipples look like the titty-tips of a high school girl!”


Before I took Teddy in to be fucked by his father, I had him face the camera and read a little speech I had prepared for him.


“Hello everyone.  My name is Teddy. I am eighteen years old. I am a dirty perverted cocksucking faggot teen. I am a freak of nature with a tiny dick that is more like the clit of a teenage girl. I need constant abuse and humiliation. I need to be corrupted and molested and abused in every way possible. I am now about to be cunt fucked by my own father, who is trying to help me. I used to be a high school jock and made my daddy so proud, but now he is totally ashamed of me, and knows that I need huge cock up my asspussy to help me. I am a filthy degenerate who will never be able to ever date a girl, much less have sex with one. “Tears began to roll down his face. “I used to think I was a normal boy, but now I know I am a laughing stock of an almost dickless piece of shit. I apologize to the former jocks at my former high school for pretending to be a normal boy like they are. All the while I was a sick, perverted freak with a clit. So if any of you  nice gentlemen out there want to punish me for being such a disappointment to  my family, former friends and schoolmate, please contact me at the numbers you see on the screen. I will be available for your punishments and discipline sessions.”


“Turn around, bend over and spread your ass cheeks for the camera to show your teenage fuckhole!”  With shaking hands, he spread his ass globes and revealed his stretched, red, raw dildo fucked asshole to the cameras. I had another camera trained on his face, because the pathetically sad, sick look on his teenage face made my dick rock hard. He looked so sweet and innocent, I began to leak pre-fuck in my pants.  I moved the cue cards so that the boytwat could continue to read.


“This is my faggot fuckhole. This is where my own father will shove his huge manly dick. He will fuck me like the cheap, sick, disgusting whore I am, and that will help me. If any of you want to fuck me to help me, contact me at the number on the screen.  I want to be cunt fucked by as many real men as possible.”


“Now stand up and turn around. I want the cameras to move in and take a close-up look at that tiny dick of yours with the pretty pink ribbon on it. Let’s give everyone a really good laugh.”


I carefully watched the boy’s chest heave with shame and anxiety. I didn’t want him to have a heart attack. That would cut all of our fun short. We had come so far with him. And there was so much more still to do. I wanted to see him dragging heavy weights across a gym floor by clips attached to his freakishly distended nipples. We had not even started to stretch his ball bag yet, and a long full nut sack would make his tiny dick look even smaller. And then there was the fist-fucking still to come. And the gang rapes and animal sex.  So much fun for me and so much pain and humiliation for Teddy!


I now slowly walked the disoriented boy into the next room to greet his father.

We switched to the cameras in the fucking room. It was quite a sight.


Teddy’s handsome father stood drugged and dazed and totally naked in the middle of the room. One of my assistants had his hand encircling the thick penis of the man and was gently pumping it. Teddy stopped dead in his tracks when he saw his own father being prick-pumped. The man’s dick was red and so hard that it vibrated. Large veins ran down the length of the prick shaft, and the cock head looked the size of a plumb and was leaking. Another of my assistants  stood behind the man and reaching around, pulled and twisted his nipples.


“Okay, Teddy, time to be turned into a fucked cunt of a girl by your daddy’s big swollen dick!

Submitted: February 27, 2022

© Copyright 2023 dale10. All rights reserved.

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Add Your Comments:



Excellent, as usual. I have been a fan for QUITE a long time. I especially enjoy your "race-play" stories. Being from a racially diverse family, I would like to see more if you decide to do so.

Mon, March 7th, 2022 9:19pm


I still do race play stories from time to time but not on Booksie for fear of infuriating some readers. I do them on my private fan list. thanks for the nice comment.

Mon, March 7th, 2022 10:40pm

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