Teddy's Humiliation Part Three

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

Small endowed Teddy's situation gets worse when he gets a visit at school from his tormentors.




Our next gathering with Teddy was even more miserable for the poor high school jock. I was determined to totally emasculate him, to strip away any shred of self-esteem the kid might still have. He had a pathetically small dick and balls, yes, but I wanted him mentally and emotionally destroyed. I wanted to watch a healthy handsome teenage boy become a totally wrecked shell of a human being for the rest of his life.


So, before our next group meeting, I paid a little visit to Teddy’s high school Oh my what a fine healthy bunch of young boys and girls. And everywhere, out om the lawn, up and down the halls, were cocky, sexy, hunky, jocks flirting with and hitting on young females. No wonder Teddy felt awkward even at school. Some of the dick bulges in the boys’ jeans were awesome. I saw the eyes of more than one girl lingering on the bulging crotch of this jock or that. And I was certain some of the girls were getting it on a weekly or perhaps daily basis.


I’d read somewhere in an article on line that because high school boys don’t like to wear condoms and because high school girls were frightened of becoming pregnant, ass fucking had become the new high school fad. I had to laugh at the ingenuity of modern teens. I wondered briefly what the Catholic Church’s stance on ass fucking was?


I asked for Teddy at the desk, saying I was a college scout passing through town, and I’d heard of the boy’s athletic prowess. Up until a few weeks before, Teddy had been a top athlete and a top student. But his new fucked up, nervous condition had not only caused his grades to tumble, but his sports performance now sucked as well. Some teachers suspected drugs. No one suspected extreme dick humiliation.


When Ted turned up at the office and saw me, he turned white as a sheet. He Knew I possessed photos which if released would ruin his whole life. When we got alone in a conference room, he balled his fists in a threatening way, but his beautiful eyes were filled with tears.


“How dare you come here to my school? You promised. You promised!” he yelled.


“Don’t raise your voice to me, you dickless twat, or it’s all over for you right now!”  I won’t take disrespect from the boys I torment.


His handsome muscular chest heaved in his tee shirt. Spittle either from anger or fear or both formed in the corners of his full-lipped mouth. He was such a perfect all American boy… except for one thing.


“I haven’t come to hurt you. In fact, as a kind of peace offering, I went shopping and I brought you some cool new duds to wear.”  


“Huh?” he said, acting like a cute dumb jock. He frowned.


“I sent shopping and bought you some cool new clothes.” I pulled them ojt of the bag I had brought along. “Well, aren’t you going to try them on?”


“Now? Why not wait until after school?”  He sensed trouble.


“Because after school I am busy, and I want to see how you look in them. Not get undressed and try these on before I lose my patience.”


He pouted. “Gim’me the clothes. “


“Get undressed first twat. By the way, while we were waiting for you to come down, I told the nice lady behind the desk, that you had said in your college application that you wanted all your records changed from Ted to T.D. I didn’t tell her it stood for Tiny Dick. So, I want you to make it clear to everyone that from now on they must call you T.D. “


I saw him blush deeply as he peeled off his shirt. What a fine, smooth, muscular torso he had. I waved my hand for him to hurry.  He blushed more as he kicked off his athletic shoes and unzipped his jeans and stepped out of him. Now, he stood in his boxer shorts and socks. A gorgeous sight.


“Well?” I asked.

“Well?” he said, holding out his hand for the new clothes.


“Underpants, Assface!  And from now on, you wear no underpants ever! Do you understand that? You go commando under your trousers, not that it will make any difference with that peanut penis of yours.”


“Do we have to do this h ere at school?” he asked, his voice softening in defeat.


“Yes, we have to, and do you know why? Because that is how I want it!” I hoped that made it nice and clear for him.


Still breathing heavily, he peeled down his underpants and stepped out of him, revealing that sweet baby dick and child’s balls that were ruining his life. I quickly picked up my phone and snapped two pictures of him standing naked in front of a sign on the wall proclaiming the name of the school.”


“What are you doing?” he screamed, his voice sounding suddenly like a little boy.


“Just getting a photo. Someday, the school may want to put your picture on the wall, you know along with other famous graduates, as the student with the smallest dick ever.” 


He was crying again. God, I loved to see that. Big hunky boy with tears running down his cheeks. I tossed him the clothes. “Here, get dressed, I have to get going, and I imagine you need to get to class.” 


His mouth dropped open when he looked at the jeans I had brought him.  Not only were they those freaky new “ultra-skinny” jeans that more like leotards, but I’d picked a size that would fit a kid of twelve.


“Are you crazy?” he barked, but I let it pass. “I can’t fit into these.”


“Just try, the salesclerk said they really stretch.” 


It was hysterical. He had to peel them up his legs like stockings. They were so thin that every muscle in his calves and thighs clearly showed. He had to struggle to get them over his hips, and he glared at me with a “see, I told you so,” look.


I told him to keep on trying. Meantime, I took a scissors out of my bag and proceeded to shred his own jeans.


“What the fuck are you doing?” he squealed, his eyes almost popping out of his head.


‘Now, I guess, you have to make them fit.” I smiled.


The poor kid was shaking terribly. He tugged the pants up over his hips but pull as he tried, he could not get them to reach his waist. The waist band rested just a few inches above his shave dick root. He was crying pretty hard now.


“You, see, you see, I can’t wear these,” he pleaded.


“Well, you’re just going to have to. And I want you to wear them for the rest of the week.”  I laughed, watching his suck in his gut to try to button the skinny jeans, that fit him like a second skin. He finally got them zipped and buttoned. Just as I wanted, it would be clear to everyone that the poor teenager had absolutely no dick bulge at all. No profile. No lump. Nothing. His shaved pubic mound was clearly visible. I signaled for him to turn around. He could hardly move in the tight, confining jeans but managed, and I was treated to the sight of one of the most glorious young male asses I had ever seen. Not only was the material stretched so tight and thin as to reveal every dimple and crease, but they rose up so low that two inches of teen jock ass crack showed above the waistband.


“I’d call that a perfect fit. Of course, there is no room for your phone and wallet, but you don’t want to destroy the look anyway, so carry them in your book bag. Now try on the shirt.” 


He was crying pretty hard by now. “Please. I’ve come to your meetings. I’ve done everything you said. Don’t do this to me.” 


Tiny Dick, I am losing my patience. I have brought along some nice photos of you that I can easily drop in the school hallway.” 


With a sob, he put on the tee shirt. It was pink. Bright pink. And cropped so it only came down a bit below his nice muscular pecs. And on the front, was a nice big picture of “Hello Kitty.”


‘I can’t go out like this. I can’t go to class like this.” He cried.


“You can and you will. All week. And you’d better not miss a fucking class. And oh, look, T.D., you don’t have any dick lump at all. I hope the kids don’t notice that. I know these clothes are a bit young for you, but since you have the dick and balls of a third grader, you might as well dress like one, right?”


He grabbed my hand. He actually grabbed my hand. And he raised it to his face and kissed it. “Oh, please! Please, I am bagging you don’t make me do this.” He sobbed. “I’ve been good. I’ve done everything you said. I can’t help it my dick is small. I can’t help it.” 


I handed him some brochures I had taken from my bag.  ‘Here is some material I want you to read about sex change operations.  You might be happier transitioning into a girl. You will be quizzed on these at our next meeting, so you had better read them carefully. Now take off your socks and put on these flip-flops. Big boy shoes don’t look right with this outfit. Tears dripped from his chin and stained the pink tee shirt. Good. He would go out in the school with everyone able to tell he had been crying. That made my dick hard.


Remember, you wear these clothes all week, or things will go very bad for you. And don’t forget about our group meeting. Remember, I am paying a high-priced whore to have you try to fuck her. That should be a hoot.”  

Submitted: August 04, 2021

© Copyright 2023 dale10. All rights reserved.

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So pleased Teddy is back! Excellent story. Really hope we get to see what happens to him at further meetings. Have loved reading this.

Thu, August 5th, 2021 6:45am

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