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

Poor young Teddy faces a big test to prove if he is a man or not, but the test is rigged so he cannot perform. Even worse, it is witnessed by some boys from his school.



IT was the big night of our next HTM (Humiliate Teddy Meeting.)  What poor teen jock Teddy didn’t realize was that I’d invited two seniors from his high school to the party. I told them to stay at the rear of the room until the appropriate moment. When you plan to slowly sexually, emotionally and mentally destroy a boy, you have to orchestrate the steps very carefully. You want to break the boy, step by step, slowly break down and self-esteem and self-worth he may have. At the same time, you want him to have to experience ultimate humiliation and degradation. If you move to fast, he will crack too soon and ruin all the fun.


I’d recently seen a new story of a teenage boy in Japan who was bullied. The clever boys who worked on him had kept up their torment all year, driving the boy further and further into despair. They arranged to meet the boy every day before school. They forced him to strip naked and masturbate while they watched. When he came, he had to shoot the wad onto his hand, and then eat his own cum. After a few weeks of this, they upped the game, but jerking off themselves into a cup and making the poor teen drink that as well as his own cum. They took photos of him masturbating naked, and threatened to send them out over the internet if he did not obey them.


Next, they invited more kids from their school to watch the fun. Soon, there was quite a crowd everyday waiting for the special show. The more the boy sobbed and begged them to show mercy, the more the crowd got off on it. It was ready to take the game to the next step. They handed the boy an eight-inch dildo and told him to stick it up his virgin ass.  If he refused, naked pictures of him whacking off would be sent to his father and mother. As you might know, the Japanese have an acute sense of shame, and the boy could not imagine his parents seeing those photos, so he painfully shoved the eight-inch dildo up his smooth young teenage ass.  The crowd loved it. They wanted to see him walk around and dance with the dildo up his ass. The more the boy cried, the more members of the watching crowd became sexually aroused. This happened every day before school. Every day became a nightmare for the poor teen.


A week later, they increased the size of the dildo to ten inches. The poor kid was in extreme pain. It was agony just to get the huge dildo up his tender teen hole, much less have to dance with it up him. The bullies made him do a special show, to which the invited some girls from his school. His mortification was complete. The girls saw him naked. They watched him masturbate. They saw him shove a dildo up his ass. Word would spread through the school.


One day before school, as the Japanese teen walked to the appointed spot head hanging in submissive shame, his entire life now a shambles, the bullies produced a large gallon jug. Then, each of the bullies took out his penis and pissed into the jug. When each of the eight boys had urinated into the jug and it was filled with strong yellow piss, they ordered the bullied teen to drink it. A few days later, he was forced to perform oral sex on the bullies. He would have to go to classes with the thickness of cum clogging his throat and coating his mouth. The bullies invited other boys from the school to get blow jobs from the poor picked on teen, and soon he was sucking off ten to fifteen boys each day before school.


His grades welt to hell, and his family thought he was on drugs. He developed a tick in his right cheek and began to stutter. Still, the abuse continued. He was warned by the bullies that he had better not try to run away or harm himself, or they would take out their anger on his family, so he was trapped.


The dildo up his ass was increased to twelve inches, and he was forced to keep it up himself all day in school. For lunch, he drank boy piss from a milk carton and his food was coated with the cum of some of the students. He was so broken by ow, he just accepted the abuse. The bullies went on line and ordered jars filled with bull and dog and horse semen and made the boy drink these. Someone bought a chastity device online, and they put it on the boy’s dick, so he could no longer get an erection. They began to beat his testicles almost daily with bamboo rods.


None of the boys having their fun stopped to think what this poor boy must be thinking or feeling. In order to have this kind of fun, you have to think of the victim as an object, a toy, not something human. At last the boy had a total  mental breakdown. It was only when he was hospitalized that the whole story came out.


I can’t tell you how often I masturbated to this news story. I wanted this same kind of thing to happen to Teddy. His small dick was a way in…a way to work on the handsome teen, to totally destroy him. When we finished with  him, Teddy would be a mere shell of a boy, terrified to even go out in public, a total failure in school and in life. The only person who would give him any sympathy would be me, and he would pay a terrible price for that.


You will recall that to dis-orient and humiliate Teddy more, I had given him some brochures on sex change operations. I had ordered him to memorize the information, and since his dick was so small and useless he should consider such an operation. I told the muscular young jock that he might be happier as a cunt!  I  had even squeezed and rubbed his fine jock muscular pecs and said that I thought with some implants, they might make fine tits. He did have more than decent nipples.


So, this week’s meeting was to further destroy the boy’s self-esteem and any linger thought he might have that he could perform as a man. In the bedroom upstairs at the mansion where we held the party, I made Teddy sit naked on the bed. I handed him a dish and ordered him to masturbate and shoot his discharge into the dish.  It was quite funny watching how he did it. He took his little dick between two fingers and kind of rubbed and rolled it back and forth. I took out my phone and filmed it, in spite of the kid’s teary-eyed protests. Of course, each time he let us film him, we had more material to use against him.


You’d be amazed the number of perverts on the internet who would love to see a really good looking teenage jock with a tiny dick masturbate.  Finally, he groaned and shot quite a good amount or cum into the dish. He looked up at me, standing there filming, thinking his humiliation for the moment was over.


“Again! Do it again!” 


“Aw, come on, please!”  he begged, but I was adamant. So, he spread his strong young thighs and masturbated again, eventually shooting a second load into the dish.  I remind you, we were alone, so my “club members” were not watching this. It really took all he had, but as he began to get wearily to his feet, I pushed him back down on the bed.


“Again!” I ordered him. I knew that most horny high school boys could cum three times in a row…shit, even more. But Teddy’s third ejaculation was actually painful for him, and only a tiny dribble came out. That was what I wanted.

“Good boy, Tiny Dick!” I said, ruffling his hair. “Now be a really good little boy and lick up all your cum!”  I held the plate up to his face. With tears running down his cheeks, and a look of infinite sadness on his face, he stuck out his tongue and began to lap at the plateful of cum. He gagged a bit and made one sound like he might puke. I warned him that if he vomited, I’d have to make him lick that up too, so he kept it down.  He looked so fucking pathetic, that I got a huge erection.


When he’d finished his sperm meal, I told him it was showtime, and he should stand up. What I’d made him do achieved the desired effect. His dick was not shrunken to a tiny nub, smaller than ever in its spent flaccid state.


“Oh, Teddy, look at that,” I said, holding a mirror, so he could see his pathetic penis. “Isn’t that sweet?”  I loved how his full young lower lip quivered and his sad eyes begged.


“Now, Teddy, remember, tonight is your big test. You have to prove to the club members that you are a real man, and that you can fuck a girl!” 


All at once, he understood what I had done. Making him cum three times, had almost depleted him. Now it would be more difficult than ever to respond to a girl. “We’ll all be watching you, Teddy, as you fuck the girl we’ve brought in. Make sure you fuck her hard and deep!”  I laughed out loud at my own joke.


I took him out of the bedroom and brought him to the top of the grand staircase.  At the bottom, there were twenty-five men waiting to see the show and two boys from his own school.


I gently nudged Teddy on the should and told him to descend the staircase, reminding him to keep his hands at his side and not to try to cover himself.


They applauded. At the sight of his smaller than ever dick, they actually cheered and applauded. I knew the poor teen wanted to die. I could see it in the way his shoulder slumped. I watched his muscular ass cheeks roll as he descended the stairs, and I couldn’t wait until we started to work on them. Oh yes, a pretty, young girl needs to be fucked, everybody knows that. And since Teddy didn’t have much of a male dick, he might as well be treated as a cunt, right?


The watching audience began to point and laugh at Teddy’s tiny shrunken dick. The naked youth began to tremble all over. I actually feared that his legs wouldn’t support him.


He was led into the large living room, where the furniture had been moved to make room for a large mattress. On the mattress lay a beautiful naked young woman., sexy enough to drive any high school or college boy crazy. She looked up at Teddy, playing with her nipples and then fingering her cunt, as she spread her legs.


“Gentlemen, tonight Teddy will prove to us that he is a man. He will prove to us that even with his pathetically small dick, he can still fuck a beautiful woman.” 


“I don’t want to…I don’t want to… “ Teddy sobbed, knowing he would not be able to perform. Even if I had not drained him, he still would have had a difficult time in front of a crowd of over twenty watching.


“Go on, Teddy, get it hard for her. If you can fuck her, we might even go easy on you.”


The kid tried. I have to give him credit for that. He rubbed and yanked on his little nub, but it just wouldn’t respond. He fingered his balls and even pulled on his nipples, but his body just didn’t want to.  He knelt down and sucked on the girl’s tits, licked her pussy, and rubbed his body against her. She told him she would love to help him by sucking his dick, but he was just too small, and it was rather gross. The crowd roared. She said that his dick was smaller than her clit, and by God, in his flaccid state, it was. The whole thing ended with Teddy lying curled up on the mattress, sobbing uncontrollably, and the room erupting in wild laughter.


While he lay on the mattress naked and rattled with sobs, I had his two high school mates squat near him, and I told him to look up. They snapped photos of him, and I snapped photos of all three of them. When he recognized them from school, he so freaked out that he fainted. I told the two boys to be sure to share the photos with other senior boys at the school.  I also told them to pass on the address of the website we were creating about Teddy.


But please don’t think that Teddy was now totally broken. Boys that age are resilient, and after all, our fun was just beginning. Now that we knew Teddy couldn’t respond as a man, why not see if he could respond as a cunt?  And also, since he had such baby equipment, why not turn him into a baby? Wouldn’t he be cute in a video of him in a diaper? I had so many ideas for our sweet little teenage Tiny Dick!

Submitted: August 17, 2021

© Copyright 2023 dale10. All rights reserved.

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