The Misadventures of Simon 1

By Casper Wright

Casperwright483@gmail.com

Copyright 2025 by Casper Wright, all rights reserved

[3,760 words]

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This story is intended for adults only. It contains depictions of forced nudity, spanking, and sexual activity of preteen and young teen children for the purpose of punishment. None of the behaviors in this story should be attempted in real life, as that would be harmful and/or illegal. If you are not of legal age in your community to read or view such material, please leave now. 

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Prologue



Simon Fulton was not your typical 11-year-old boy. Simon was sick, tired, and fed up with everything, but more specifically, he was annoyed that his dreams and fantasies would never come true. Nor would they, unlike what he thought most boys imagined. Simon had a specific kind of fantasy.

Upon discovery of what intense pleasure comes from rubbing his penis, Simons imagined being surrounded by people in embarrassing and humiliating moments or being dominated and told what to do and being spanked for minor misdeeds.

Simon is a bright 6th-grade kid, getting mainly A’s and B’s, although his teachers believe he does not apply himself and is far brighter than he lets on. Simon is about 4 foot 1 inches (125 cm), approximately 65 pounds (29.4 kg), with light olive skin, medium-short beige-blonde hair, and light brown eyes just outside his Greek nose. Thanks to his Greek mother, Sophia Fulton, and German father, Leo Fulton, Simon was a very fine-looking boy. 

He was standing in front of his closet mirror, looking over his naked body. Not muscular, not fat, just skinny with a light tone from growing. His butt was not significant, just lovely and round. What he likes most about himself is that which would have frustrated most kids; his 1.2-inch penis, which began stiffing as he became more aroused by his thoughts, at its peak reaching only 2.5 inches erect, which is one of the smallest from what he has seen from his class during gym, but not the smallest. 

That “honor” went to Ted Blanton, who looked to have just over an inch long penis soft, a slightly chubby black kid who looked like he was waiting to hit a growth spurt. Teb had short, black, curly hair and dark brown eyes. He was teased a bit for being a nerd and chubby. Still, it never escalated beyond mocking and the occasional pantsing (tighty-whities), not to the point where Simon could live vicariously through Ted. Plus, Simon would fantasize that he was being forced to suck Ted’s dick against his will. Though Ted was not the only kid, he would consider doing the same.

At the beginning of the school year, Simon had worn boxers, but with teasing and other kids getting picked on for wearing tighty-whities, Simon switched back. It did not work, as most people liked him, so all that was commented on in a joking manner was that he should switch back to boxers so they did not have to see his thighs. That did not go as planned; in some of Simon's fantasies, they would kick him out of the locker room in only his underwear (or, better yet, naked). Nevertheless, he was not even close; he did not tighten his gym shorts to make it easier for someone to pants him.

Simon began stroking his penis again for the third time today, getting into a fantasy where a teacher would call him up in front of the class and strip naked. They would have him face the class with his hands on his head while he got spanked. Then he would be required to choose a boy to suck off. Simon would always pick the boy with the largest dick, who, in theory, would be the one who mocked him the hardest and the most likely to produce sperm for him to swallow. 

Nevertheless, as he neared completion, Simon stopped. I am frustrated and sick of not getting the fantasy to come true. Simon knew it should remain a fantasy and that the real thing would hurt him physically and mentally, but he still wanted it. After all, if this much pleasure could come from the fantasy, then the real thing would bring even more pleasure…right? So removing his hand from his penis and collecting his thoughts, Simon decided that from now on, he would only masturbate if someone ordered him to do so. 

Now, the question was, “How would I accomplish this? How can I make any of my fantasies come true?” Most of the stories he read and researched came about in the sixties and seventies. It is 2024; how could he get kids to act like the kids in the stories? So, he sat and thought and thought. I lay in bed during dinner and use the toilet while attending school and class. Almost 2 weeks had passed, then he watched a crime show, and it hit him, “Why not blackmail.”

It is not ideal; yes, blackmail is sometimes in his fantasy. A kid having authority over him, forcing him to do things through blackmail. However, could he blackmail a person to make him live his fantasies? They would not have to know it was him. A mystery person who has it out to make Simon’s life miserable.

“So, who should I place on my list of potential targets?” Simon thought as he pulled a blank notebook paper from his binder. Sitting at his desk, he began writing. 

Initial Targets:



“Unfortunately, that will not be possible, as they would not have anything to use against them. However, it would be nice to come home and continue the torment. Stricter, less privacy, maybe spanked or paddled…... Focus.”




Each has shown that they are willing to be cruel and have repeatedly bullied Ted. On a chance encounter, Simon could take a video, without anyone seeing him, of them taking turns kicking Ted in the balls to see if he had any. This was done with Ted fully clothed, so later Simon imagined that he was Ted, stripped naked and getting repeatedly kicked in the balls. This was as bad as it ever got for the three bullies, so Simon would have to give them detailed instructions to accomplish his goal. Still, he would have to start slowly and build up from there before any sexual encounter could happen.

“Now, I need a girl smarter than the boys and might make things interesting as things progress. Someone who has issues with males would be ideal. I recall hearing something about Hope Simmon's Dad possibly being abusive.”




However, she will be a challenge as she is smart and keeps her nose in a book most of the time. Not drawing attention to herself, which makes things difficult. “Will need to get the teacher involved too, but that will require something pretty detrimental.” With the list started, Simon decides to borrow his parents' credit card and purchase a few items, but he is pretty sure they will not notice if he keeps it small.

Simon gets online and orders a paddle, thinking for future use, a few small cameras that require a cable to download footage, a hollow book, and a couple of Terabit memory sticks. After doing so, create an anonymous email (mre@bemail.com) using a proxy server. Locates each person's email via school group chat.

Well, let us begin.



Sunday (Day 0)







(Simon/Mr. E)

Dear Boys,

As you open the attached video, you will see the trouble you may be having.

After all, you can see that you are physically assaulting that boy. There is no telling how many others might come out once this gets reported. You will be kicked out of school, which from your grade will not mean much. No, the real trouble is, YOU WILL BE SENT TO THE JUVENILE DETENTION.

Now, luckily for you, I do not care about your life. My interest is in Simon Fulton. I want to ruin his life, and if you follow every task that is given to you, I will not have to use the video. You might even enjoy this.



Tomorrow, during gym, you are to pull down Simon’s shorts. I want video evidence that it occurred. Suppose I do not have a response by tomorrow evening. I will report the incident.

Sincerely,

Mr. E







Simon, having typed and sent the email, was getting hard just thinking about how embarrassed he would get with all those girls around him seeing his underwear. However, he stopped himself; no one had told him to masturbate. So, Simon pours himself into his homework and moves on. After that, play a video game before dinner. After dinner, he brings a package that has arrived in his room. Carefully remove each item and verify that it works. Simon then stores them behind his headboard in a pocket covering the back. Overly anxious, he opens his secret email, and there are three replies.







(Grant)

Mr. E

This is blackmail! You will not walk away if I ever find out who you are.

Though since you put it that we would go to jail, I am willing to do as you asked. I will pull his shorts down during gym class.



Grant



(Jay)

Mr. E

I never liked Simon, so do not worry; I will play along. I convinced the others that you would send the video if we did not go along. I will take the video to show that we completed the task.



Sincerely,

Jay



(Mike)

Mr. E 

You are lucky Jay convinced us to help you, as I wanted to go to the police. However, he says we could get in real trouble; this might be fun. 

I will distract our coach so we do not get into more trouble.



Mike







This got Simon’s blood pumping, and an instant erection. Shutting off his computer and getting ready for bed. Simon was grinning from ear to ear, knowing what tomorrow would bring. The only thing that would make it better is if he sprung an erection during the pantsing, adding to the humiliation.

Just before falling asleep, Simon mentally noted that he would need to gather evidence on Hope. There must be something about that girl he can use.



Monday (Day 1)



“Man, that was a weird dream.” Simon thought as he woke up at 5:30 to get ready for school. His 2.6-inch flag is waving for relief, which he looks at, but he is still waiting to be told he can, pulling up his secret email confirming that it will happen. Simon dressed in regular briefs, shorts, and t-shirt, ate breakfast, brushed his teeth, and followed Dad to the car to head for school/work.

Upon arrival, Simon begins his lookout for Hope. Finding became the easy part; trying to find something to use against her proved challenging. Hope seems to talk with everyone, but her attitude toward boys is direct but not aggressive. She always appears to be doing the right thing, even studying during study hall. “This might take a while; I might need to find another girl.” Simon thought. 

Just thinking about what she could do got Simon thinking about his last class of the day, gym. Anxious about the time coming closer, much like a final test that will count against you. He is thinking of all the girls in his gym class who will watch as his pants get ripped down, and he will be standing there with his underwear on display. It got so bad that Simon thought about calling it off, so he went to the bathroom between classes to calm his nerves. Being horny and not having masturbated in over a couple of weeks has gone to his head; it could be the only reason he did not. 

This moment of anticipation has arrived on his way to the gym, “Breath, calm down.” Simon is getting his nerves under control. Simon entered the locker room and changed into his gym clothes (The one item the PTO could approve for the school requirement to cut back on clothing damage), a white school T-shirt, black shorts, and gym shoes. He ensured that he did not tighten his shorts like always and entered the gym. 

They begin with a stretch; one boy and a girl take the lead and demonstrate each stretch. All the while, Simon starts to imagine what it would be like to lead and have his shorts pulled down in front of the class, with all eyes on him. It is good that he is in the back, as it gives him a semi. He adjusted it to get back in the stretch. This got Simon wondering when or if they will do their part; hopefully, they will not chicken out.

Our coach, Weatherby, announced it would be a free day, so everyone dispersed into groups. Some boys started a basketball game, while a group of girls started jumping ropes, and the others began cheering on the game or walking around the gym. Simon walks around, sticking close to the girl's group for maximum effect. Simon could see Grant, Mike, and Jay whispering in the corner. “When will they do it? The anticipation was killing me.” Simon thought as he continued to walk around.

Near the last fifteen minutes of class, Mike came out of the bathroom and went over to Coach Weatherby; in a serious tone, Mike stated, “Sir, something is wrong in the bathroom! You need to come quick.” off they went. There was poop and water all over the floor. Simon could see Mike standing at the door, and just off to his right, Jay had his phone out, clearly ready to take a video. 

Grant came up behind Simon, placing his arm over Simon's shoulder and giving him that evil smile like you knew something terrible was about to happen. “Everyone! Let's see what kind of underwear Simon has!” Grant shouted, drawing attention from everyone, as he pulled Simon's shorts to his ankles. 

Simons’ heart began beating out of his chest as he froze right in place. He felt every pair of eyes right on him, specifically his tighty-whities. Simon was mortified, embarrassment building up like he was ready to explode. The laughter erupts, and kids point out his underwear as he stands dumbstruck. Then he felt a sudden release, pulled his shorts up, and walked to the other corner of the gym. The laughter died down, and they went back to what they were doing, not trying to draw attention to themselves.

For the rest of gym class, Simon stood in the corner, conflicted over what happened. On the one hand, that was the worst moment of his life, but on the other, his penis was as hard as steel. Fortunately (or unfortunately in the other part of Simon's mind), that did not happen until after he had pulled up his shorts. “That was embarrassing; I cannot believe everyone saw my underwear. I must have looked so pathetic to everyone. I am not sure I can keep this up; all the girls were laughing at me and now have seen me in my underwear.” Simon's thoughts were everywhere, and he was red all over, not wanting to be near anyone right now. Simon began sneaking glances at everyone, but they did not appear hostile. “I kind of liked it now that it is over,” Simon thought, “but if this continues, I will have to try to calm myself more. People might start suspecting something was up.”

After going to the gym, he showered, switched back to his regular clothes, and headed out to find Hope. Trying to remember her last class, he almost missed her leaving middle school and heading toward high school. Simon thought that was unusual as she was not related to anyone in the high school, which gave cause for Simon to pull out his phone, ready for anything. Staying out of sight, he watched Hope as she approached a high schooler. Something was off; Simon brought up his camera and began recording. Come to find out that she was passing off marijuana to the high school boy, who paid her.

“Perfect! Hope is selling pot, and I got it on camera. This will work; she is going to have to work with this. Dealing drugs to a minor is a crime while having it on school grounds is also a criminal offense. This is so good.” Simon thought as he beamed with joy over his discovery. When the coast was clear, he left for the pick-up area to wait for his mother. Waiting, he watched the video repeatedly without mistaking what was happening and the items' content.

Upon arriving home, he pulled up his computer, finished his homework, and then pulled up his secret email to see a response to today's event.







Jay

Mr. E



Attached is the video you wanted to prove our commitment. I think it is to your liking. Let me know if there is any more fun that you can send our way.



Thanks,

Jay





Simon opens the attachment and, from the android video, watches himself stand there as his pants are pulled down and the look on his face of pure embarrassment; because of his shirt hanging down, you could see the bottom of his underwear and his less tan legs. Simon went from soft to a steel erect penis in no time flat and started to rub it before he realized what he was doing. He stopped himself as nobody told him he could and began typing new emails to minions.







(Simon/Mr. E)



Dear Boys,



Congratulations on completing your task and showing your loyalty. The video was ok, but the outcome was successful. Though this is more evidence of the file against you guys, you are safe FOR NOW.

Your next task will be in the gym locker room before class. While Simon changes, you are to give him a wedgie, not just any wedgie; continue to pull until his underwear rips and take them with you. I want a video recording of the event, and to embarrass him more, I want to show the remains to the girls.



Good luck,

Mr. E





Simon looked over his instructions and hit send. His tormentor side was smiling at what he had accomplished thus far. Simon had given himself a wedgie before for one of his fantasies, but never to the point of ripping. Leaving him without underwear for the remainder of the school day. Plus, Mr. E is insisting that his underwear should be unsightly for more embarrassment. Something which Simon prides himself on is his hygiene. Plus, no one is supposed to see his underwear; hence the name: they are to be worn under your clothes. 







(Simon/Mr. E)



Hope Simmons



I recommend watching the attached video; the distribution of drugs on school grounds could get you in serious trouble, and while your customers might deny the whole thing, this video alone will open an investigation that will ruin you and your reputation. 

It is good that you are not my final target, and that is where you come in. I want to make Simon Fulton’s life miserable, and you will help or suffer the consequences. You will find Simon coming from the gym after tomorrow's final class to prove your commitment. You are to force him into an empty room and pull down his pants. He will probably have no underwear, then have him place his hand on top of his head and get a photo of him in his glory. If he refuses, threaten to leave with his pants. Please send me a copy of the photo.



Yours truly,

Mr. E





Simon's nerves began to rise again, “The first girl will see me naked; I wonder how she will react. Will she laugh at me or stay silent and direct as she normally treats boys?” Simon was not sure but was excited. Tomorrow should be even better than today; here is hope. 

Simon had dinner and settled with the folks before heading to bed; after a shower, walking back into his room with only a towel wrapped around his waist. Simon pulled up Mr. E's email to check for a response.

INCOMING Message



(Jay)



Mr. E



This is getting good; I will do the honors of giving that loser, Simon, the wedgie. He will not see it coming, and man, it will hurt.

Thank you,

Jay



(Mike)



Mr. E

Jay seems more excited than usual about this, but it is not something we have done before. I will help keep Simon from struggling; it should be easier with my skills.



Sincerely,

Mike



(Grant)



Mr. E

As we agreed on tasks, I will video it and, per Mike's suggestion, will add pics of the girls holding the underwear. Mike has provided a better camera, which was given to him by his grandmother for a better picture. 



Sincerely,

Grant



(Hope)



Mr. E

I am not sure who you are, but you better pray I never find out, or there will be an empty grave with your name on it. Do not think I will not be looking.

As for Simon, I will get the photo you requested, as I am only dealing to be able to leave this town.



Your Enemy,

Hope




This is a revamp of one of my favorite Authors (Arclos). Much will remain the same, and some will change. I hope that by revamping the story, I can continue where it left off.








   
   
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