Teddy's Humiliation Part Five

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

Poor Teddy is almsot broken but not totally yet. His concerned father is brought into the picture, and some humiliation is dealt to him as well.

Teddy’s Humiliation Part Fiveby dale10


Handsome popular, eighteen-year-old high school senior jock Teddy had become a pathetic wreck, a shadow of his former self. After his inability to sexually perform in front of a party full of men, including some boys from his own class in school, he more or less fell apart. As well as getting photos of him on the mattress with the hooker, I and many of the guests got close-ups of his tiny useless teen dick, make sure his face was also in the shots. We also took some photos of him naked and crying which included his high school mates, so the boys could verify that the pathetic jock with more of a clit than a dick was indeed Teddy.


But don’t think for a second that I was through with the miserable twat boy. Oh no, we were just getting started. He was just too cute to not want to totally fuck him up for good.


It was after the arty when he was llying naked and sobbing on a bed upstairs, that we gave him some drugs to knock him out, and I had one of my doctor friends perform a little minor surgery on him. Nothing serious.  A minor botox injection in his lips, so they looked a bit like whore lips, some injections in his big pouty jock nipples to make then swell like whore tits. Another set of injections into his ass lips, to make his rear hole look a bit more like a cunt. And a tongue piercing.  That is right, a silver ball.  That way, he would find it impossible to speak without quite a lisp. I felt Ted’s new personality required a lisp.  He would not object of course, or the photos of him unable to fuck a female would be sent to his parents, his grandparents, his little brother and others.


You can imagine how miserable he was when he came around, and I told him the tongue piercing had to stay in permanently. He was a broken boy. He had developed a stutter beside the new lips, which was really cute. I reminded him that the college scholarship reps were coming the following week, and he had to be on his very best behavior. I know he felt tht if he could just get over this hurdle, he would be okay.  


I wanted to end the school week with a bang for Ted, so learning that Friday was to be “out of uniform “day, I pitched in.  It was a day when the kids could abandon their dress codes and come to school as casually dressed as they wanted. I chose a really nice ensemble for Teddy. Pink short shorts and a pink crop tee shirt that only came down slightly below his nipples. He still had his tight jock tummy, and it looked very appealing.  I made sure the shorts were four sizes too small so they barely closed and rode only about an inch over his dick root in front and that two inches of ass crack showed in back. I completed the outfit with pink platform shoes with a four-inch cork sole.  He had to kind of shuffle in them.

To try out the outfit, two of my friends and myself took him to a fast food restaurant. We made him get up and order and fetch the food.  About thirty kids in the place roared with laughter at him, not even trying to hide their scorn. And when he spoke to order with his new lisp, the place rocked with laughter and kids all over the restaurant began to talk with lisps.


We were drugging Teddy n ow, just enough to keep him disoriented, but not enough to ease any of his shame. When he returned to the table, I reached over and broke the top button and zipper tab on his shorts. Now if he was not careful, the pants would slowly open to reveal his tiny dick. He had to constantly tug at the pink shorts. I did mention did I not, that we had shaved his entire crotch, so he was bald as a new born babe down there. We also shaved his ass and his legs.


We doused him with cheap perfume., and happy with our choices, that is how we sent him to school. 


Of course, he was now the laughing stock of his school.  Word had gotten out from the dudes at the party that Teddy had such a tiny dick he could not even fuck. So, girls stopped talking to him.  Imagine, here was the leading athlete in the school, the boy that all the girls had been hanging on and chasing after, and now they just snickered at him.  He heard them whispering behind his back and laughing at him.


In gym class, the boys wanted a good laugh too, so they began to ride him about why he never wanted to shower with them. They reported him to coach for not showering, and the teacher told Teddy that he could not go through the school day unshowered after gym class. It was bad hygiene.  So he was ordered to shower.  All the boys in the gym class lined up to watch Teddy pass them to go into the shower room. He was trembling so badly he thought he would pass out.

One of the braver boys reached out and tugged the towel off Teddy, leaving him totally naked.

The boys roared wildly when they say his pathetic tiny dick. Teddy started to cry. Here he was, the star athlete and leading student at the school, sobbing as he walked naked into the shower room, followed by his whole gym class.


“Jesus, he must use a tweezers to jerk off… “ one boy said and they all laughed.


“Don’t be stupid, Rick, you don’t jerk off a clit, you rub it.” 


“My girlfriend’s clit is much bigger than his!”


“Please, guys, just leave me alone,” Teddy sobbed, bug with his new lisp, it caused gales of wild laughter.


“Hey, don’t his tits look bigger too?  Maybe the dude is turning into a cunt.”


It was true. The botox injections had swollen up his nipples until they looked ready to explode off his pecs. They had become so sensitive; he could hardly wear a shirt. The boys stood around telling him to make sure to wash his clit and titties.

He begged them to leave him alone. He wanted to run away, to leave school and leave home and never come back. He no longer even cared about the  scholarship. He couldn’t take the abuse any longer.


I know we had promised the boycunt that if he was a good tiny dick twat for us, we would keep our fun with him private. That he had to only serve six months as our toy, but it was just too fucking precious to watch him exposed to the kids at his school to follow our own rules.  And thus, the “costume dance.”


I should mention that that weekend was the first time Teddy was ever benched  for a game.  He was trembling so badly and so broken, he couldn’t even play decently. Coach and others suspected the boy was on drugs.  Such a shame with all the scholarship scouts coming to town in the next few weeks.


Teddy’s parents didn’t know what to do.  Time for me to enter the picture.  I approached them as a “teen counselor” who had been approached by the school.This was bullshit of course, but they were desperate to try anything. I told them I felt I had to pull the boy from school for a week, and take him on a “Self Worth Retreat.”  They heartedly agreed. This of course would give me and my buddies a full week to totally fuck-up and wreck the kid. 


But first, the school “costume dance.” This was an annual event at the high school. Kids would spend tons of money on amazing costumes. Some of the more creative ones made their own. Parents and faculty would visit the dance to take photos and enjoy the extravagant fun.  Jocks came as everything from Prince Charming to James Bond to marvel super heroes. Girls came as princesses, “Wonder woman,” and “Super Girl.”  


Teddy begged to not be forced to go, But I told his parents that he needed healthy social interaction. And I had the perfect costume for him. He had no idea when he showed up at my place before the dance. I had ten of my buddies over to help “dress” our favorite small dicked jock. We ordered him to strip naked.

I always got a hard on at the look of shame on his face.  And it was really funny when he begged us, “PLEATH”  with his pierced tongue. A side note. His dad had confided in me that he feared his son was gay. I told the worried gentleman, that it was possible, and I would work with him to clarify his sexual identity.


“Please help him.” Teddy’s father had begged. “I don’t want a faggot son!”  


I told the poor man that part of Teddy’s sudden faggot turn might because of his amazingly small dick. I said that boys with pathetically tiny dicks often revert to becoming cocksuckers.”  This hurt the dad even more, and he teared up. I decided to push a little.  I asked Ted’s father if he had a normal sized dick. The man blushed and said yes, his dick was healthy and normal.


“I hate to do this, Sir, but in order to help your son, do you think you might show me your dick?”


Ted’s dad turned beet red. He said that really wasn’t necessary, but I told him that I had encountered many troubled boys whose problems stemmed from father complexes, and I had known several fathers to lie about their own inadequate dicks. Paul, that was the name of Ted’s dad, assured me that his dick was more than adequate. But I insisted that medically I simply had to make sure in order to help his son.


So, much to my perverted delight, the man unzipped and took out his dick, which I must say was most impressive.


‘ I can’t see it clearly, Sir. Would you please tug your pants and underpants down and lift your shirt, so I can give an accurate medical opinion?” 


The man’s fucker hung six inches flaccid. over huge hairy balls.  I could see how embarrassed he was.  I took out my phone and snapped a few pictures which made him even more uncomfortable. 


“I know this is not easy, Sir, but think of it as helping your son. He feels inadequate in every way.” 


The fit thirty-eight year old reached down to tug up his pants and underpants.

“Oh no, Sir, please.  I have to see it erect”


He blinked.  “You’re kidding me, right?”


“I’m afraid not, Sir.  You see, Teddy may be suffering from what we professionally call a “Daddy Dick Complex.”  His own inadequate smell penis may create an obsession with your seemingly large cock. For all you know, he may even be spying on your in the bathroom or even God forbid when you fuck your wife.” 


The handsome man shook his head. “Not Ted,  he has always been such a good boy. He wouldn’t do something like that.”


“You have to admit, he has fallen apart lately. Just as he was about to get a scholarship and everything.  He could be under serious mental strain, and some of it may have to do with his sexual identity and his feelings about his own father’s dick.  Now please, sir, help me to help your son. Please get erect for me.” 


It is so easy to fuck up loving, worried parents. Ted’s father stood there masturbating his dick in front of me. Oh God, it was so hot to see how ashamed he was to have to do this. And what a nice fucker he had.  I am certain he stretched out Ted’s Mom when they first married. The man was hung rather like a horse. It reached eleven inches hard and thick as a beer bottle.  He certainly had nothing to be ashamed of. Well, not yet anyway.  He stood there, red in the face, his huge hunk of fuckmeat swaying and bouncing in front of him over huge hairy balls.


“Thank you, Sir. I know how hard this must be for you.’ I stepped back to snap some pics of Paul. “Just for our records. I swear, this is going to help in our work with your son.  You have no idea how teenage dick envy can affect a boy’s performance and self-image.Sir, I’m having a bit of trouble getting a good shot. Could you please open your shirt, so we can see your chest and stomach. You look to be in great shape, Sir.  That’s better.  Your hard dick is going down just a bit. Give it a few pumps for me, will you?” 


Ultra-conservative Paul, Teddy’s caring dad was going through this humiliation for his son. Because he loved his son. He stood there masturbating his dick, his huge balls dancing, as I snapped photos. How would I use these revealing photos? 

How would I use them in Teddy’s destruction?  Well, that was all part of my plan.


But next I want to tell you about our fun costume for Ted at the high school costume dance. We decided to make him attend as a “BABY” in diaper and bonnet and plastic pants and sucking on a huge cock shaped pacifier. This would  totally destroy him in the eyes of all of his schoolmates. Especially when the  Exlax we fed him went to work! More about that next time.

NOTE:  This story is fantasy. the author does not condone or support any behavior in this work.

Submitted: September 05, 2021

© Copyright 2023 dale10. All rights reserved.

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Still loving this. Looking forward to the next part.

Wed, September 22nd, 2021 10:55pm


Thank you for your support and enthusiasm. It certainly helps a writer to get positive feedback. dale10

Wed, September 22nd, 2021 4:10pm

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