The Misadventures of Simon 1 to 4

By Casper Wright

Casperwright483@gmail.com

Copyright 2025 by Casper Wright, all rights reserved

[16,975 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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The Misadventures of Simon

By Casper Wright

Email: Casperwright483@gmail.com

This story is intended for ADULTS ONLY. It contains explicit depictions of sexual activity involving minors, which I DO NOT condone and is to remain a fantasy. If you are not of legal age in your locality to view such material or if such material does not appeal to you, do not read further, or save this story.

Prologue

Simon Fulton was not your typical 11-year-old boy. Simon was tired and fed up with everything, but more specifically, he was annoyed that his dreams and fantasies would never come true. Nor would they, as unlike what he thought most boys fantasized about, Simon had a specific kind of fantasy. Upon discovery of what intense pleasure would come from rubbing his penis, Simon imagined being surrounded by people in embarrassing and humiliating moments or being dominated and told what to do, and being spanked for minor mistakes.

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. 

Standing in front of his closet mirror, analyzing the details of his naked body. Simon was not muscular, nor fat; just a slender abdomen growing into a healthy boy. His butt was not significantly large, just a lovely round tone shape. What he likes most about himself is that which would have frustrated most kids is his 1.3-inch penis, which began stiffing as he examined it, at its peak it reached only 2.6 inches erect, which is one of the smallest in his class from what he has seen 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. Ted 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, not to the point where Simon could live vicariously through Ted. Plus, Simon would fantasize that he was forced to his knee and suck Ted’s dick against his will. Though Ted was not the only kid, he had considered doing this too.

At the beginning of the school year, Simon had started wearing boxers, but seeing others getting teased or picked on for wearing tighty-whities, Simon switched back with hopes for the came. It did not work, it turns out most people like him, so the only comment made 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 even 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.  As he neared completion, Simon stopped. Still frustrated with not getting the fantasy to come true, he still wanted the real thing. 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 others to act like the kids in the stories? So, he sat and thought about it over and over; lay in bed, during dinner, use the toilet or while attending school in class. Almost 2 weeks had passed, then as he watched a crime show, and it hit him, “Why not extortion.”

It is not ideal; yes, but extortion is sometimes in his fantasy, although it normally involves them having authority over him, forcing him to do things through extortion. However, could he extort a person to make him live his fantasies? They would not have to know it was him. A mystery person who has it out for Simon, to make his 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:

Mom (Sophia, 33) Supervisor Agent for Homeland Security

Dad (Leo, 36), Chief Financial Officer for a multibillion-dollar construction company

Simon thought, “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.”

Grant Dixon (12, black hair and dark-brown eyes) Tallest in class, 5'4" (162cm). He is not very bright, but he is good with his hands. He will probably follow in his single-alcoholic father’s footsteps of working at the manufacturing plant. 

Mike Simpson (11, Platinum blond hair and sapphire-blue eyes), Slightly shorter than Grant at 5'2" (158cm), is very talented in art/photography but has yet to appreciate it, though that is one of his only good grades. He also has a blue belt in Taekwondo, but he is not someone I want to fight.

Jay Charles (11, red hair and meadow-green eyes) is the shortest of the three at 4'6" (140cm), and the smartest of the three has the highest grade of C in non-participation classes. He seems to bully others purely because he enjoys it and likes to take the lead on most torments.

Each has shown that they are willing to be cruel and have repeatedly bullied Ted. On a chance encounter, Simon had taken a video, without anyone seeing him, of them taking turns kicking Ted in the balls “to see if he had any”, their reasoning. 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.”

Hope Simmons (11, shoulder-length, light-brown hair, brown eyes), straight A’s, athletic but does not compete in sports. I believe she will leave this town behind when she graduates and never return.

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 serious trouble you’re in.

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 grades 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. So, if I do not have a response by tomorrow evening. I will report the incident.

Sincerely,

Mr. E


Having typed and sent the email; Simon’s dicklet was pointing straight up thinking about how embarrassed he would get with all those girls around him seeing his underwear. Simon began absentmindedly stroking it, but when he realized what he was doing he stopped himself; sticking to his drive that he is not allowed to masturbate without being told. So, Simon poured himself into his homework and moved on with his day. After dinner Simon took a shower and being overly anxious, he opens his secret email, and there are three replies.


(Grant)

Mr. E

This is extortion! 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 boner, which was tempting, especially having not done so in almost 2 weeks. Simon shut off his computer and got ready for bed. 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 still wants to be told to jerk-off, pulling up his secret email confirming that it was not a dream. 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 at Crestwood Private School, Simon began 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. She always appears to be doing the right thing, even studying during study hall. “This might take a while, she doesn’t appear to do anything that I can use; 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 your grade. 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; 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 took 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, which he had to adjust 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 jump-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 yanked down 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.

A package arrived for him when he got home. He brought the package to his room, carefully removed each item and verified that they worked. Simon then stores them behind his headboard in a pocket covering the back. He 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 and stopped. Simon typed out a response to his 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 until his underwear rips and take them with you. I want a video recording of the event, and to embarrass him more, I want you 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 tomorrow after the final period. 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 all his glory. If he refuses, threaten to leave with his pants. 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 hoping.

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 new we haven’t done before. I will 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 jay’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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The Misadventures of Simon

By Casper Wright

Email: Casperwright483@gmail.com

This story is intended for ADULTS ONLY. It contains explicit depictions of sexual activity involving minors, which I DO NOT condone and is to remain a fantasy. If you are not of legal age in your locality to view such material or if such material does not appeal to you, do not read further, or save this story.

Tuesday (Day2)

(BEEP. BEEP, BEEP) Simon rose out of bed, ready for today, feeling much better about his experience from yesterday. Though he was still nervous about today, he ate his breakfast, brushed his teeth, and headed out with Dad for school. On the drive to school, Simon looked over his homework/school planner, making sure everything was completed or not due yet, keeping his grades up like a good kid. 

Upon arrival at school, Simon spotted Hope getting off the bus, and his heart started racing with anticipation. “Hope is going to see me naked today… well, at least see my penis. Is she going to make fun of me; am I going to chicken out and will she take my pants? Will she leave them outside the door or leave with them? If she leaves, will I walk through the school with my penis and butt on display for everyone to see?” Simon thought as he tried getting a hold of himself. The very thought was giving him an erection; “I hope that she does, even though I did not have to tell her. Not having to do all the work would be nice and having a few surprises would make things more interesting.”

The first period consisted of English with Mr. Sato, going over the information Simon had already completed a week ago. Simon began daydreaming about later today, (Hope forced him into a room and pulled his pants down. Simon's shirt was shorter than expected and she began laughing at his tiny penis, which shrunk with embarrassment. He would try to shove his way out, but she would block every advance. This would cause Simon to give up and place his hands on top of his head. Hope would continue to laugh as she snapped a photo, then she would push him over, grab his pants and walk out, leaving Simon to run through the school with everyone laughing at him on his way to the pick-up spot for his mother) Simon's penis was now painfully throbbing. Luckily, Mr. Sato called on Simon to answer a question to get him out of his head. 

Social Studies for the second period with Mrs. Winchester was another bird class, which made for the perfect time to pretend to be sick. Mrs. Winchester smiled at Simon as she gave him a pass for him to the school physician. Unlike most schools, Crestwood School was a private school that had a great scholarship program for states and company employees. One of the requirements voted for by the PTO and the school board was a proper physician. Dr. Marjory's office was in the same building as the gym right across from the Coaching office, and since Simon is planning to continue misadventures of embarrassing tasks, bullying, and spanking. He would need to get the staff involved. If there was one thing he learned from yesterday, one of the goals for the gym would be to transition to briefs as being his only gym uniform…for now.

Now the gym/health office building consists of three locker rooms, one for the males, one for the females, and one for the staff which is only accessible through the Coach's office; then you have the health office, the gym, and an equipment room. Both the male and female locker rooms had three doors, one that led into the hall, another into the gym, and the last one only let you out for safety purposes. Upon entering the main doors to the building, Simon could hear a gym class going and no one appeared to be in the coach's office. Simon had brought with him one of the hidden cameras in a hollow book, just in case, which he added to the bookshelf in the coaches office without anyone being the wiser. 

Simon then entered the health office and told Dr. Marjory that he was feeling dizzy during class. She did a quick check-up and suggested he take a quick nap. Simon pulled his phone out and wallet out and set them on the counter with the camera facing the Doctor, then Simon closed his eyes. There was a rumor about the Doctor having been popping pills, which Simon was looking to use to his advantage if it turned out to be true. 15 minutes later Dr. Marjory woke Simon up and sent him back to class, as he stated that he was better. Gathering his things he headed back to class, and at the same time pulled up his video, and sure enough 5 minutes in she had taken some pills from the student prescription cabinet. Mr. E/Simon's fate was on his side.

Once returned to class Simon discovered they were doing a pop quiz, and the teacher was going to have him remain in the hall until the end of class, but Simon said he would like to be given the chance to complete it, as to challenge himself on the subject. With a smile, Mrs. Winchester handed him the quiz and Simon began working quickly, which he still completed before the end and most other students.

Before his next class, Simon used the bathroom and peed, purposely did not shake off when finished creating a pee stain in his underwear. Then headed to math class with Miss Korn, with nothing interesting occurring. After lunch, Simon goes to the bathroom to poop, though this time he chose not to properly wipe, making his otherwise clean underwear less presentable.

Like Hope, Simon used Study Hall to work on any schoolwork that was not completed in class and his software class that was offered through the school. 

Then on to the last class of the day, physical education/PE, Simon was still nervous about knowing what was going to happen but felt that he showed it less as he approached the gym. Heading straight in and getting changed, starting with changing his shirt and then removing his shoes, at which point he could see Grant just off to the side with the camera out. Simon pretended not to notice and as he dropped his pants Mike walked up to Simon grabbing hold of his wrists, while Jay came up behind and grabbed a hold of Simon's underwear and yanked straight up; even with prior experience, this hurt far worse. His penis and balls were crushed from the gravity of his underwear, as it continued to descend in between his sweet butt. Simon began begging for release, trying to get some relief. “Please let me go, I will not say anything. Help me, please, someone.” Mike was quick with his hand over Simon's mouth,” Shut up, loser. You get what you deserve.” Jay lifted higher and the pain intensified, and you could hear the threads tearing. The other kids just watched as they heard the rip and Simon dangling by his underwear in tears, praying that it would be over soon. 

At last, the last few threads rip, with Simon landing on his feet, only to have Mike push him over, commenting “What a loser.” Simon lay on the floor with his shirt pushed up and his penis not only on display but getting hard, hurting, and unable to move. As everyone started pointing, laughing, and making rude comments around him, Simon felt humiliated and even more embarrassed about having an erection in front of everyone. He got up and dressed quickly, not wanting to be in the same room. Everyone headed out to the gym floor to get ready for class.

During class when the coaches were distracted Simon could see Jay showing each of the girls and occasionally pointing toward him and he could see them giggling. Simon would turn red as the girls looked and giggled well, wrinkling their noses, and shaking their heads in response to the state of his underwear. This continued until the end of class. With not having underwear on, Simon showered and changed quickly.

He just entered the school heading for the drop-off/pick-up. Only to be pulled into the custodian closet and have the door locked. Still trying to recover from the humiliating class, Simon was not quite ready for this, but continued to act the part of a victim. “What are you doing? Why did you drag me in here?” Simon asked. Hope kept her composure and replied sternly “What I have too.” and grabbed his pants and pulled them down sharply to his ankles. Simon’s instinct kicked in and he covered his privates. “Why did you do that!?” turning red from embarrassment. Hope looked him over for a minute, finding it interesting that he was not wearing underwear and entertaining that he was attempting to hide his privates. “Place your hand on your head now!” Hope said as sternly as always. Simon did not move a muscle but began reaching for his pants with one hand. Hope stepped forward, which made Simon stop what he was doing, and she pushed him gente, but firm enough to cause Simon to step out of his pants. “Please, leave me alone! I never did anything to you.” Simon claimed. Hope picked up his pants and turned toward the door. “Fine, I’ll leave you alone; but I’m taking your pants with me unless you do as you’re told.” Simon did not move, and his heart rate increased. Hope unlocked the door and grabbed the handle. “FINE! Fine, I will do it.” giving up in fear that she would do it. Simon slowly raised his hands to his head, raising his shirt in the process to expose himself. Hope's eyes were drawn to his penis, with nothing obstructing her view, and began laughing. Not sure what she expected but not this. “Is that all you have? You cannot even call yourself a man, let alone a boy. I am quite sure that babies have bigger penises.” Hope exclaimed as she pulled out her camera for a photography class and snapped a photo. Simon’s eyes began watering as the humiliation and shame became overwhelming.

“This better be enough to satisfy him,” Hope whispered to herself, as she dropped his pants and walked back over to the door. Hope smiled and stated, “Have a nice day, baby dick Simon.” opening the door and leaving. “Who are you talking about?” Simon asked as Hope trailed off. Simon placed his pants on just as he got an erection, blushing from the thought of what might have been like if he had been hard, when Hope had captured him…maybe later. Since no one was around. Simon headed back to the coach's office. Seeing only the head coach inside Simon leaned against the wall to retie his shoe, to look occupied. When the Coach headed into the staff shower, Simon bolted in, changed out the spy camera, and ran for the parent pick-up spot. Getting there just before his mother showed up.

The whole ride home, Simon was quiet, looking out the window and thinking about today's event. Even though they were humiliating, he felt that he should keep going, as it hasn’t quite made it to where he wanted just yet. Simon went right in and finished his homework, then uploaded the video from the camera onto one of the external memory sticks. After the upload was safe and finished, Simon viewed the video and hurried through the day until he found a good clip. Head Coach Marvin and Coach Sumner were having sex right on the office couch and you could see students just on the other side of the window walking past even with the blinds closed. Simon knew that they were not a couple but were both married. “2 down, 4 coaches to go.” Mr. E/Simon rearing his head, let us get the new my next minions initiated.

INCOMING Message 

(Jay)

Mr. E

Mike gave me the camera, as he has a better one. Attached is the clip and pics. I am not sure what your deal is with Simon, but I have spoken with Mike and Grant, and we agreed that if we do not get into trouble, we will collaborate with you. However, trying to get around the Coaches and teachers is going to be a problem.

Partner,

Jay

—-

(Hope)

Mr. E

This should satisfy your perverted needs/test. Now, please leave me out of your games. 

Your enemy,

Hope

End Transmission

Looking over the clip made Simon wench again and grab his nuts, from a phantom pain; and embarrassing as he could see his butt clear as day. Not to mention when his underwear finally gave out the camera had a quality photo of his erect penis. When Simon clicked on the photos, knowing that each girl was looking or holding his underwear even better. Hope was right when she took the photo; he looked like a little boy and knew his penis was under his age group. 

Begin Response

Boys, 

This has been a great week thus far and well done on showcasing Simon’s underwear in the gym. You really seem to enjoy tormenting him. I will of course add this to my collection and expect further compliance and evidence of completion. 

Tomorrow, I would like you to take the remains of Simon’s underwear and share them with the rest of the school when Simon is around to bear witness. Then turn them over to Coach Sumner before class, stating you found them in the locker room, yesterday.

Just after gym, you are to take Simon's clothing and dump them in the trash, while he is in the shower, and when he returns, have him join his clothing. 

Sincerely,

Mr. E



Dearest Hope

There is no need to get rude, I will admit that extortion is not ideal, being called a perv is not a good look for you. Someone might think you have an interest in Simon. Though I guess it would have been better if he were hard during his photoshoot.

It should be simple tomorrow; you'll need to coerce Simon into doing anything by using this picture. Make him prove that he is under your power, by doing something embarrassing, painful, sexual, gross, or anything you can think up. I do not want to know just yet, let your creative side show, and then send me a copy. I would like to know that you are still following my instructions. 

Sincerely,

Mr. E



Dr. Marjory Adams

As you can see from the video, you have been taking drugs that are not prescribed to you. Last I checked illegal drug use will take your job, medical license, and RX license, and you most likely end up doing something. I could end your life, without killing you with just an email. Though, it is not your life I am interested in; It is Simon Fulton’s. If you perform your duties and tasks as they come in, I will keep this between us.

Tomorrow, before Simon passes your office at the start of the last period. You are to take him aside and explain that there are options for his small penis size. He just needs to make an appointment to see you for a follow-up examination after class. 

Your duties as they relate to Simon will be as follows: 

-When you are examining Simon, he is no longer allowed privacy, the door should remain open, and no curtain drawn. All examinations for Simon should only wear underwear. 

-All thermometer readings are to be done rectally, with no underwear on him. He is not allowed to cover up, nor given any privacy even then.

-Any medication needed should come in a suppository, if possible.

-If you see Simon being pranked or bullied, leave them to it unless you can make it worse for him.

-Any unauthorized erection should be met with a painful bare bottom spanking.

If you are concerned with the other staff, the head coach will back you up. I am pretty sure that the remaining coaches will fall in line as well shortly.

Sincerely,

Mr. E



Coach Kyle Marvin

If you have reviewed the clip, you will notice in the blinds students move to/from class, while you and Coach Sumner are having sex on school grounds. Now I am in the position to end your marriage, possibly bring in a lawsuit that will impact your career, and probably have you brought up on charges if the police and PTO get a hold of this.

Now, luckily for you, I am willing to overlook this for now, if you follow my tasks when sent. My target is Simon Fulton. When it comes to Simon you are never to help, when he is bullied, pranked, or anything else for that matter. Your staff will be following soon so be prepared to attend if needed. Tomorrow you will find Simon in a trashcan in the bathroom after the boy’s shower. You will help him out of the trashcan and suggest he follows the advice of Dr. Marjory, with no repercussions for anyone. 

Sincerely,

Mr. E



Coach Annabelle Sumner

If you have reviewed the clip, you will notice in the blinds students move to/from class while you and Coach Marvin are having sex on school grounds. Now I am in the position to end your marriage, possibly bring in a lawsuit that will impact your career, and probably have you brought up on charges if the police and PTO get a hold of this.

Not to worry yet, if you follow tasks as they come, there will be no issues. You are no longer allowed to assist Simon when he is bullied, pranked, or anything else for that matter. Tomorrow during class pull Simon aside and confront him in front of the class about poor bathroom habits. State that if this becomes a habit, you will need to check he is doing it properly.

Sincerely,

Mr. E



End Transmission

Simon had a knot in his stomach as he sent his email, knowing that tomorrow would be full of embarrassing moments, and this was just the beginning. Heading for dinner and hanging out with the folks, running through his head, what would he change if he could get them in the circle? Simon popped an erection right there at the dinner. Maybe always be naked and punished for this erection. Maybe more chores even on the weekends and punishment for missing something small. It is late for bed, I will have to write this down. When taking a shower Simon edged himself twice. This week thus far has been worse than the last two weeks without rubbing one out. Checked his email before bed.



Incoming Transmission

(Jay)

Mr. E

First, giving a ripping wedgie was bussin.’ I never even crossed my mind to pull something like that off, nor show the remains to the girls. As for that task tomorrow, I will take care of Simon’s clothing. Mike is better at documenting, so he will capture the whole thing. Grant is going to place Simon in the trash can.

Partner,

Jay



(Hope)

Mr. E

What do you even have against Simon? There must be something, and I think, once I figure it out, I will find out who you are. I understand you want me to extortion Simon, and I will, Simon will not enjoy it. Will there be an end game to this? 

Hope



(Dr. Marjory)

Mr. E

I do not know who you are or how you got that video, but if it were not for my family, I would turn this over to the police. You are a despicable person and if I ever find out who you are, I will report you. For now, I will follow your instructions.

Dr Marjory



(Coach Marvin)

Mr. E

How dare you threaten me and my family? What kind of man does something like that? I love my wife and do not want to put her through that kind of hell, and that is the only reason I will follow your direction. If I find out who you are I will beat you into a wheelchair!

Coach Marvin



(Coach Sumner)

Mr. E

Just note that I wanted to go to the police, but Kyle made a compelling argument about our families. So, for now, I will toe the line, and Simon will pay the price; but once I find out who you are, I will report to you.

Coach Sumner

End Transmission

—-

Simon shut down his computer, climbed into bed, and went over today’s event; About what it felt like to have that underwear ripped and then lay there on display for everyone else to see. This got Simon rubbing up and down his torso getting lower and lower, bringing him to his hairless pubic area and finally caressing his small flaccid 1.2-inch penis. Bring him to think about how Grant, Hope, and Coach Sumner are going to humiliate him. Thinking about how Dr. Marjory will mention the small penis issue. His penis is throbbing again. With that, he took his hand away and shoved his hand under his pillow pretending his hands were restrained leaving him exposed and unable to give relief to his throbbing member. A tear ran down his face as he left his member just flying there in the open with no relief. After about 5 minutes, Simon reached over and turned off the light. Good night. I am off to my sweet nightmare.

++++




The Misadventures of Simon

By Casper Wright

Email: Casperwright483@gmail.com

This story is intended for ADULTS ONLY. It contains explicit depictions of sexual activity involving minors, which I DO NOT condone and is to remain a fantasy. If you are not of legal age in your locality to view such material or if such material does not appeal to you, do not read further, or save this story.

Wednesday (Day 3)

Simon woke before his alarm, having had spotty sleep with the constant hard-on from the last 2 days. Trying to pee was extremely difficult with the throbbing penis. Afterward, he got dressed, ate, and headed out, feeling sluggish. Being a private school, his dad was able to drop Simon off early and head to work. Simon went into the social studies classroom as it would remain unoccupied today and planted a camera, then left the room. Headed toward the entrance and waited till the homeroom opened. Pulling out a book to pretend, while observing the people moving about. Simon was still nervous about whatever Hope had planned. I mean it is one thing to know what is going to occur, and another to know something is going to happen but not sure what. Hopefully, she does not take it too easy on him, but he also does not want to end up in the hospital.

Hope's bus normally shows up 20 minutes before the home room, so students can grab breakfast. So, when she got off the bus and spotted Simon, she thought that it was a suitable time to start now. Not having to worry about homework when she got home, allowed Hope to research what she was going to do to Simon. Not sure what she was going to do, she had only pulled down his pants and taken that photo because of Mr. E, as well as the reason she was going to have to extort Simon. Though she did enjoy the power she has over Simon, and part of her is going to enjoy tormenting him, she hoped that she would not be controlled by Mr. E for too long. Linking Simon and Mr. E as the same person never even crossed her mind. Hope did wonder how Simon could have drawn the attention of such a person.

Hope started with domination stories to gather ideas; there were interesting ideas and things she would love to try out; like dildos, butt plugs, canes, and chastity devices, though when she's not sure how that will work on Simon, she naturally made plans for the future and most of this she wouldn’t have a way to acquire. Initially, she should start slowly because, like Mr. E, she was just getting started; that thought of that made her shiver. So, she went to a truth or dare site and got an idea. Grabbing a few clothespins from above the washer and placing them in her backpack. Surprisingly, this was more enjoyable than she thought. She thought that if Mr. E was going to go to this much trouble to work Simon over, then she would make sure she put her energy into excelling as well. 

Hope walked over to Simon, grabbed his wrist, and told him to follow her. She led him right into the empty classroom, locked the door, and closed the blinds.

“What is it that you want? Why am I here?” Simon asked, trying to sound more intimidating, but scared, playing off the uncertainty of what she was going to do.

“You are going to do whatever I want from now, or this,” Hope said, as she handed Simon a copy of the photo she took yesterday, “will be distributed around the school and maybe even social media.” Hope paused to let it sink in as Simon looked over the photo of him displaying himself, then continued, “For now this will remain in my possession, and do not even think about alerting the teacher or anyone else, because it will get distributed then as well. You belong to me whenever, wherever I choose. Understand?”

“Wait, you are blackmailing me?” Simon attempts to get confirmation, as they are in the social studies classroom, the only classroom unoccupied on Monday, Wednesday, and Friday; and the one he bugged when he arrived. Hoping to pile on evidence to support Mr. E against Hope.

“Yes,” Hope said like always; and just like that Simon had what he needed to keep this going. 

“Why are you doing this? Is there something that I have done to you? What do you have against me? Simon asked, trying to see what she could produce to justify her actions.

“No, not any one thing you have done, but that does make me curious. Do you know someone that has it out for you?” Hope prying for information to locate who Mr. E could be.

“I did not before this week that I know of. Just you and the bullies, Jay, Grant, and Mike.” Simon replied, as it was true there was nobody else that Simon was aware of. Hope pondered over this information and quickly dismissed those boys as being Mr. E as this level of smarts is not in their wheelhouse.

Hope grabbed the photo from Simon, shredded it, and threw it away. “That was only a copy, so let us get started. Strip naked, now!” Ordered Hope.

“Now?” Simon states, surprisingly. 

“Yes, now.” Hope sternly replied.

Simon looked at her, as his heart started racing, in disbelief; and then realizing that it was not a dream, began taking off his shoes and socks, then moved onto his shirt. Looked down at the floor, “Okay, not so bad” Simon thought, until he reached for his pants button and he started to breathe faster. “This is happening and there is nothing I can do but follow her lead.” Being Simon right now felt completely powerless, as Mr. E had no control here; Hope was in charge and that required him to remove every stitch of clothing. So, Simon continued and removed his pants, leaving him in only his clean tighty-whities.

Hope took a picture, as he stood there closing his legs and placing his hand in front of his underwear. Hope smiled during the first shot and then pushed his hands away to take another. Simon’s face turned red with embarrassment, because a girl was seeing him in his underwear, and not the typical ones of mature boys his age. “I am pretty sure; I said strip naked. Get those off as well and do not bother trying to hide your penis.” Hope demanded, causing Simon to grab his underwear quickly, but then gently pull them off and toss them to the rest of his clothing. Now completely naked he placed his hand at his side as Hope took pictures from every side, which Simon started soft but quickly sported a full erection. Like most eleven-year-old boys Simon was feeling shame from this, but part of Simon enjoyed this.

Hope paused and reached into her backpack and pulled out the clothespins. “Okay, slave. Time to see if you understand your role. Place one of these on each nipple, one on your ball sack, and the last on the head of your penis. Then wait until I tell you to take them off.” Then she placed them down on a desk.

Simon picked one up a little disappointed, as he thought they did not hurt, they were just annoying. Until he placed the first one on a nipple and quickly changed his mind. In pain wanting to take it off all the while looking at Hope for some relief. She just shook her head and gestured to continue. Simon apprehensively applied one to the other nipple, adding to the pain. Hope was able to capture the moment. 

“Please don’t make me place the rest on,” Simon begged, realizing the pain was lessening.

Hope stepped forward and began twisting the clothespins on his nipples, “Do it.” stated plainly and sternly, as Simons began tearing up. Hope stepped back and Simon placed the next one on the head of his penis, which hurt about the same as nipples. But now for the one he dreaded; He gulped and applied the last to his ball sack. He hissed and danced around for a minute. Then Hope took a few more pictures and then started messing with each pin, and making fun of Simon, calling him a baby as tears ran down his face. Luckily, the pain started to wear off, but it was getting close to school time, and Hope ordered him to remove the pins. Simon, not knowing any better, started with his nipples, and the pain shot right through him again and more tears followed. Getting control of himself and taking the band-aid approach, took the rest of them off, one by one rapidly, but now in pain until it subsided.

Hope placed everything away, then said, “Alright slave, stop sulking about and get dressed. I will see you later.” Simon jumped up and got dressed rapidly, Hope grabbed her bag and opened the door as Simon tied his last shoe. Simon gathered his belongings and acknowledged that, even though Hope's test was painful and quite effective, he had loved it. 

Simon headed to his first class, no one suspecting that he had just been stripped and tortured. Or that he was planning to take things further as he acquired more evidence. The rest of the day, every time he saw Jay or Grant, they would be holding his underwear talking with a girl, and pointing to him, causing the girls to laugh at him. Each time renewed the embarrassment he felt yesterday. That and being ill-prepared causes Simon to get a B- during a pop quiz in science class. Simon spent most of the lunch thinking about how he would get the rest of the staff involved or out of the way. Hope also spent her lunch, who Mr. E could be and what else she could have Simon do, as he is now under her control. Simon, after all, was now in her hands. Why not play around with that?

Simon poured himself into his schoolwork during study hall trying to make up for that error in science. After study hall Simon headed to the gym for his final class of the day. Just as he entered the building Dr. Marjory pulled him aside near the locker room doors and said “Simon, it is time we talked about your small penis and lack of growth. I would like it if you could stop by to schedule an appointment for an examination. Okay.” Then she turned and walked back into her office. Anyone who had entered the building stopped to listen and stared at the two of them, making Simon turn red and look like he wanted to disappear. Coach Marvin was standing in his doorway, to ensure no one was messing about when this occurred and thought it was strange practice on Dr. Marjory's side. Well, the class went smoothly, and he went to talk to her about it. They quickly discovered that Mr. E was extorting them both, but they were clueless as to how Mr. E obtained the damaging information or who was interested in causing Simon's suffering. Simon did not have any enemies, but he was not the most popular kid either. Simon was smart, and respectful, and helped others without sounding condescending when they needed it in class. It is obvious that Mr. E, whatever he is, is a shameful and dysfunctional individual. They sat down and went over the rules he had sent thus far and realized that Simon was going to be in for a bad year. However, for now, they will have to follow his rules. 

During class, Simon was pulled aside by Coach Sumner but remained in the class for the rest of class to hear and displayed them stating that another student had brought these to her attention and then went over proper bathroom hygiene, as this underwear clearly shows he is lacking. If this becomes a problem, she will be doing random inspections for him to ensure he is keeping healthy. Starting with having him drop his pants right there. Not believe what he was hearing, but clearly, she was unwavering. Simon lowered his shorts for all to see his underwear again. Wanting the floor to just swallow him up. Coach Sumner had him turn in place and stand there for about 2 minutes. Then told him to pull his pants back up and get back to class. Then she looked at the rest and shouted at them to stop staring and get back to class. Simon remained quiet for the rest of class and just went through the motions. After class, Simon went in, removed his uniform, and wrapped a towel around his waist to shower. Well, he was in the shower, Jay took all Simon’s clothing and threw them into the big trash can by the hall door. Grant just sat on the bench near the shower waiting for Simon, and when he came out and saw his locker open with everything missing, he looked around. Jay came over and stole his towel and Grant picked Simon up and placed him in the same trashcan. “Enjoy your new home, loser,” Grant said as he left the locker room. Simon was completely on display as everyone filtered out, looking at him without making eye contact. Jay was the last to leave, spitting on Simon as he walked out. Simon is in tears feeling the shame, defeat, and humiliation well stuck in the trash can. Coach Marvin came in 2 minutes later and pulled Simon out without helping with his clothes. Looking over Simon with the realization of how small Simon looks. Coach Marvin felt bad for the things that were happening to the boy, but to protect his family he said. “I think you should head over to the medical office and see Dr. Marjory about your little problem.” and then left the locker room. 

Simon felt like no one was going to help him now, but as he stood there, thinking about what had occurred today solidified that he was enjoying being tormented and isolated, so much so that he was getting hard just thinking about today's events. Simon got dressed and headed over to the medical office where Dr. Marjory scheduled a physical examination in 2 weeks after school for his mother to attend and discuss treatment going forward. Simon took the appointment slip and once in the hall saw that the coach's office was empty, he ran in, swapped out the camera, and headed straight for pick-up. 

Simon gave his mother the note and talked about his day, leaving out the interesting parts. Once home he put so much focus into his homework during study hall. Simon closed his door and uploaded the footage from today's cameras onto the memory stick that was processing. He looked around his room and thought that he was going to need to move his spy package somewhere else, then thought why not the false door in the back of his desk? It was made like the president's desk, as he liked the vintage design with modern features, he got to see it once when he was touring the white house with his mother. Once the upload was complete Simon edited the files from the classroom and stored them in Hopes file. Then cut through the coach's office and found out that our star athlete, Bradley Starr, is a steroid user and his supplier is none other than Coach Reese Sorenson, head coach of the football team. Most shocking was Coach Taylor Weatherby, as he groped and kissed a female student, Callista Ringo, on the office couch. Simon broke the video down and created a file for each, working on a plan but not sure what he was going to have them do.

Once everything was finished, Simon opened his email.

Incoming email

(Jay)

Mr. E

I cannot believe the day Simon had, I mean the pictures we got with the girls today were better than yesterday, and seeing Simon's reaction to the Docs and Coach Sumner was priceless. Did you have anything to do with that? I cannot believe he had to drop his shorts during class. That was awesome.

The others and I prefer that I be the only one contacting you but will continue to cooperate. Let me know what our next task is, thank you.

Jay

—-

(Hope)

Mr. E

This should satisfy your interests.

Hope

Outgoing email

Jay,

I appreciate the message and am willing to work with your arrangement. Thank you for the pics with the other female students and the video, it captured the expression on Simon's face, as well as the front of him. 

For Thursday's task, you are to give Simon a “Special bath” after class. Once he has removed his clothing, you will drag him over to an unflushed toilet and proceed to wash him using his underwear and that water. 

Sincerely,

Mr. E



Dear Hope,

Those are amazing shots and congratulations on your creativity, continue to hone that skill and test it upon our dear Simon. If he is to give you any trouble just remind him, who holds the cards. I do not have any tasks for you thus far, but I would be willing to make a recommendation. Think about having him masturbate right in front of you, I am pretty sure that the power to take such a private moment would entertain you.

Sincerely,

Mr. E

—-

Coach Marvin,

Excellent job, completing your task. You might be wondering how I know of your success. Similar to the evidence that places you in my grasp, I can reach almost anywhere. For tomorrow's task, after the last period, you are to go into the male locker room and assist Jay, Mike, and Grant with a special bath; ensure you bring a rag. After saying "thank you," Simon will get dressed and lead him out of the locker area. You should then give Mike, Grant, and Jay props for their inventiveness and dedication to helping a fellow student.

Best wishes,

Mr. E



Coach Sumner,

The speech was spot on and making him drop his pants in the middle of class, shows amazing initiative. Tomorrow between classes you are to return the torn underwear to Jay discreetly. Then after the last period, you are to wait in the hallway for troublemakers. When Simon comes out, accuse him of not showering properly and present him with two possible punishments; One is to take a supervised shower in the girls' locker room or two he is to receive a bare-bottom spanking/paddling in the privacy of your office. No other form of punishment is allowed, nor any leniency. Simon's life is about to get harder, and mercy will be a thing of the past.

Best of luck,

Mr. E



Dr Marjory

An effective approach today sticks with your instruction, and I will be in touch before the appointment. I have something in mind but will be doing research on the subject first. I would recommend looking into suppository vitamins.

Sincerely,

Mr. E

End Transmission

Simon kept grabbing his penis with each email, it was getting better and better. Simon was grossed out by the thought of being covered in pee, but Mr. E was demanding. Not to mention he was not sure which punishment he would pick from Coach Sumner. Just then the response came through.

Incoming email

(Jay)

Mr. E

This next task sounds like fun, to change who is doing what. I will hold Simon, and Grant is going to document this occasion, and Mike is going to wash him. Still not sure about the Coaches, is there something you can do? This is to keep us out of trouble, but this is starting to get risky. 

Jay

End Transmission

It was nice to have a response to his email, but part of him wishes that they just get the task and execute it without responding. Wonder how they are going to react to having the Head Coach show up and assist with the washing. Simon finished his emails and wandered around the house, trying to keep his mind off tomorrow. Simon's parents were both highly successful, so their home was pleasant. There were five bedrooms, two of which were turned into offices for his parents, and two primary bedrooms with suites. Mom insisted on staying fit, so the basement had a great gym. Since his father enjoyed cooking and had been teaching Simon since he was a young child, his father insisted on having a lovely pool with a pool house and an outside kitchen/grill. Simon had been down to the basement a few times but was not as active as he wanted, but what interested him most down there was the unfinished space on the other side of the house under his primary bedroom. When his parents were out sometimes, he would go into that part of the house and pretend it was a cave filled with dragons, or as he got older a dungeon, in which he was tortured and enslaved. Simon took off his clothes and walked around as there was only one entrance to this side and his parents never came over here. Simon's imagination started to run wild with the thoughts of a cage in which he was locked for a day with no food or water, as punishment for something and only let out after 8 hours to be beaten and then again before bed to be beaten again, at which he would be placed in on his knee with his arms tied to the top of the cage, his ankle and knees tied to either side of the cage and blindfolded. Then five construction lights would be placed around him, ensuring there were no shadows on his body, then left alone for the night., only to be awakened in the morning to be beaten once more and sent to chores before being able to have pureed beef stew for lunch.

At this time Mom stated that dinner was ready, pulling Simon from his dream. He dressed and headed upstairs where he ate a good dinner and hung out with his parents until he had to get ready for bed. He did not really feel like checking his email before bed tonight. Just climbed in and fell asleep. Good night. I am off to my sweet nightmare.

++++


The Misadventures of Simon

By Casper Wright

Email: Casperwright483@gmail.com

This story is intended for ADULTS ONLY. It contains explicit depictions of sexual activity involving minors, which I DO NOT condone and is to remain a fantasy. If you are not of legal age in your locality to view such material or if such material does not appeal to you, do not read further or save this story.

Thursday (Day 4)

(Beep, Beep, Beep) Simon got out of bed ready for the day. His 2½” nail led the way as he went to the bathroom to pee, wash his hands, and brush his teeth. Simon looked at the mirror, appreciating his features, his hairstyle (undercut with brushed back), the light brown eyes, his chest still boyish but beginning to form pecs, his nipples protruding slightly, his abdomen flat and smooth with his belly button not quite an outie or an innie, his legs toned and void of hair. His buttocks remained soft and round, like those of a young child. Regardless of the fact that it was starting to tone. Simon was hoping that his smooth groin would remain hairless for the foreseeable future. His soft penis, which is just 1 ⅕" long, sticks out; Simon wonders what it will be like when it grows longer and if there's a way to delay or shrink it for added humiliation. His balls haven't even descended yet. Simon knew puberty was around the corner; if only there could be a way to delay it longer. Simon's dad reminded him they were going in five minutes, so he concentrated on starting his day. Simon dressed, collected his schoolbag and spy gear, and set out for school.

There's nothing better to start the morning than listening to early 20s rock music, and Dad kept humming along as we drove to school. I was relieved to leave the school. Simon and his study group entered the science classroom to get ready for tomorrow's test. Shortly before heading off to homeroom, he walked to the back of the class to sneak a camera into the eyelet of the artwork that showed the periodic table of elements.

Hope sat up last night trying to fight the feelings she was experiencing over the Wednesday event with Simon and avoiding her drunken father. She hated Mr. E for what he made her do, and she was kind of loving the control she had over Simon. It was both disgusting and fascinating to consider having Simon masturbate in front of her. Hope was certain that even though she detested men, she was relishing the ability to invade Simon’s intimate moment, torment him, and view a boy's penis, plus she was curious about how boys masturbate. Seeing it in the videos is one thing, but having a boy do it right in front of her was vile, but still different; this was real. Hope reopened the email after hearing her father leave for his night shift, and after considering the day's events and his suggestions, she repeatedly masturbated herself before going to bed.

Hope hadn’t even decided if she could go through with it, with having Simon masturbate in front of her. She spotted Simon just as he arrived, appearing confident, like the last couple of days were a dream and he was ready to take on the world as he entered the science lab. That did it; she was irritated. What did he have that made him show such pride and confidence? I’m going to take that away from him, show him he’s not so mighty.

When Simon came out of the science room to head for homeroom, he saw Hope looking right at him. She thought he looked nervous and scared. Like the seriousness from him reminded him of his situation. If only she could read his mind, she would know how close she was. Simon struggled with the ifs: if she would require him to masturbate if he could perform if she only made him edge himself. He had no control here, making him more nervous and excited about living close to what he was hoping for. Simon was lucky that he was still dry firing as he had to walk to class with a steel nail in his pants.

Hope waited at the entrance of the lunchroom for Simon, as it was the best time to approach Simon. When spotted, she called him over and told him to follow her. She led him to the science classroom, as it was empty right now, locked the door, and pulled the blinds.

“Is there something you need?” Simon said in a timid voice while avoiding eye contact.

“Drop your pants and underwear to your ankles.” Hope stated in her stern, make-of-fact tone.

Simon compiled hesitantly, though more slowly than he had anticipated. Hope reminded Simon of her power by pulling out her camera and starting to record. "I'll be expanding my collection with this. Now you are going to give me a nice show and masturbate for me. Now!” Simon's mouth fell open when he heard this, according to Hope. Inside, Simon was fighting both sides: He wanted this and was excited to be under her control, but the other side was still ashamed and felt it was wrong of her to see him this way.

“I don’t want to. Please leave me be." Simon pleaded, all the while Hope was able to see his penis was hard. Hope, displaying her confidence and intimidation, walked over and said, “This says otherwise,” as she flicked the end of his dick, surprising him. “Now start. Unless you want me to distribute the photos of you to the rest of the student body,” and walked back to the counter.

Simon paused a moment, trying to let things sink in before reaching down and starting to rub up and down his penis. Both Simon and Hope are in disbelief that it's happening. Even as confident as Hope's face showed otherwise. Simon continued to rub and closed his eyes but occasionally looked at Hope. While she caught every bit of it happening and was not able to turn away. Everything she had planned this morning went out the window, from mocking him to telling him how pathetic he was. She just stood against the counter, turned on by what she was witnessing and the power she held to make this happen.

Simon continued to rub up and down, and his breathing began getting more rapid. You could see his chest rising and falling. Then Simon began shaking, having the best dry orgasm of his life. If he wasn’t holding on to the counter behind him, he would have fallen over from all the energy he used. Simon rode the euphoria as he looked at the ceiling, only to be brought down by laughter. Hope was standing there with a hand over her mouth trying to quiet her amusement. “Wow, a little boy in so many ways. Such a small, pathetic little boy, who can’t even cum.” She said as she got control of herself and collected her things. “I’ll be seeing you later, baby,” as she wiggled her pinky and left.

Simon pulled up his underwear and pants, just as she opened the door. His mind raced over what just happened, the embarrassment and shame he felt as she just mocked him and made an indication of how little he had. Now that he was not horny, the thought of calling the whole thing off was stronger than ever. Wanting to go home and curl up in his bed.

But then his mind got the better of him; would he even be able to reach out to the others before it happened? Plus, even as humiliating as that was, it was one amazing orgasm. He knew that he was going to have to and wanted to continue to live through it. With that said, he smiled, changed out the camera, left to finish lunch, and headed to study hall.

Imagine Jay's surprise when Coach Sumner stopped him between classes to have Simon's torn pair of underwear handed back to him. “You need to take care of these; let me know if there are any more incidents like this,” and walked back to the gym. Jay thought it was weird and didn’t even say anything to Mike or Grant. It dawned on him when he went to the gym what they were for, but he still could not believe Mr. E might be behind it.

PE class was great as they had a 5k run around the school grounds and park. After class, Simon went to his locker and took off his fitness attire. Mike only grabbed one arm as he dropped his underwear and grabbed his towel; Jay took away the towel, tossed it back into Simon's locker, snatched his other arm, and then pulled him to a toilet that wasn't flushed and looked as if multiple people had used it. Grant was standing off to the side, capturing the entire thing. The other boys in the locker room either watch in amusement or ignore it, trying to not draw attention to themselves. However, everyone went back to showering, changing, and leaving.

“What are you doing?” Simon asked, sounding scared. “Just giving you a hand. We are nice guys.” Mike replied as Jay handed him the torn underwear and grabbed Simon’s other arm as well. “Hold still, so Mike can start, loser,” Jay stated, as Simon tried to pull away. Mike soaked the underwear in the urine-filled toilet and began working on Simon's left foot.

“Ew, gross,” Simon said aloud as the cold urine/water smeared over his foot.

“Oh, shut up, loser, or we’ll stuff a dirty sock in your mouth,” Jay said, shutting Simon up instantly. Simon was grossed out from the bath and embarrassed to get washed by a boy his age.

Mike continued his pace as he didn’t want any more urine on him than what was already there, and he also didn’t want to get into trouble. Mike wondered if Simon was confused as to why they had started to bully him so suddenly. It is not like he did anything to them, and they have taken this further than any of their other victims. As he was recording everything, Grant wanted to know what Mr. E had in store for Simon and how extreme he was willing to go. Would there be a time they said no to him? Jay could care less; he was enjoying himself, and making Simon miserable was the highlight of his day. Why hadn’t they started tormenting Simon earlier? Mike Moved on to Simon's right leg when there was the sound of someone clearing their throat. Mike spotted where it came from first and stopped what he was doing. Grant saw where he was looking and stepped back, getting scared. Jay and Simon looked over their shoulder and spotted the head coach, Marvin, in the doorway. All the other boys appeared to be gone.

“Stay right there, Grant.” Boomed the coach as he stepped in. Jay let go of Simon, waiting to hear the verdict. Simon smiled, pretending like the coach was there to save him. You could feel the tension building in the room as the coach took another step toward Simon.

Coach Marvin found the "special bath" that Mr. E had mentioned to be completely repulsive! He nearly felt like throwing up, kicking the three children out of school, and giving Simon a hand! Additionally, he had a fleeting suspicion that one of the three bullies might have been Mr. E, but he was also aware of their intellectual background, and not one would have the knowledge or ability to pull this off. If he had to guess, Simon would be the only one with the knowledge and means to do something like this, even though he puts himself off as an average kid. But who would do something like this? No, Mr. E must be out there somewhere getting his information to torment the little boy.

“Well, I see you finally made a change and started to help your fellow students. Isn’t that nice? Don’t stop on my account.” No one was expecting that response and thought it was a trap. But they were dumbstruck when the coach pulled out a rag from his back pocket, dipped it into the toilet, and started to clean Simon's leg.

“What are you doing, Coach? What's going on?” Simon asked in confusion.

“Help clean you up. Didn't you hear Coach Sumner yesterday? No, close that mouth before I give you a paddling on top of the bath.” Coach Marvin stated firmly and looked at Mike to continue. Grant had been filming the whole time. Jay went and grabbed Simon's things and set them on a nearby bench.

Both the coach and Mike cleaned Simon's hands, arms, stomach, back, and chest together.

"All right, I'll clean his face and you clean his groin." Coach Marvin answered. Mike went on to clean Simon's butt, including in between his taint, balls, and Simon’s penis. At the same time, Coach Marvin took to scrubbing Simon's entire face, including his eyes, nose, and mouth. Simon squeezed his lips tight trying to get it in his mouth, but still, some entered as the smell almost made him puke. Tears started to escape Simon’s eyes as they finished.

“Time to clean his hair.” Coach Marvin said as he grabbed the back of Simon’s neck, plunged his head into the toilet water, and flushed. Simon came up coughing when pulled out. “Almost done. Do any of you boys need to pee?” Coach asked the boys. Catching Simon off guard, but the boy said they did. Coach pushed Simon to his knee and made him spread them. Then took the camera from Grant, and the boy circled Simon. Ensuring the only penis on camera was Simon’s, they let loose and peed all over him. Simon realized that it is one thing to have old, cold pee on him, but more humiliating to have some pee right on you.

Once the last stream stopped and had been put away. The coach said to Simon that he should thank his classmates for helping, then get dressed and leave. Simon begged to be able to take a real shower only to be met with a stern look and comment from the coach as to what was wrong with the one he just had. The coach stated again more forcefully, Thank your classmate, dress, and leave. Feeling defeated, Simon did as he was told and walked to the door. With one last look, he walked out.

The coach turned around to address the three bullies. “Why did you record that?”

Grant said he didn’t know. But it’s still not sitting right with Coach Marvin.

“Did Mr. E put you up to this?” Coach Marvin asked

“How do you know Mr. E? Are you him?” Jay replied, taking the lead, as he had been suspicious all day.

“No, I'm here on Mr. E’s demands.” Coach Marvin replied, keeping it short so as to not give too much information.

“How did he get you to follow his demands? What did you do?” Mike asked curiously.

“Well…for now let us just keep that between ourselves and Mr. E and keep following his instructions for now, at least until we can find out who he is and how to stop him. This reminds me, "Good job on taking the intuitive approach to assisting your fellow classmate.” Coach Marvin stated as he escorted the kids out.

Meanwhile, when Simon exited the locker room with tears in his eyes, he could smell himself and was hoping that the smell would come out in the wash. Just as he was standing there, he could hear footsteps behind him. It was Coach Sumner. “Simon, wait right there,” she said as she walked up. As she got closer, she could smell pee coming from somewhere; it was not until she was right next to him that she realized where it was coming from. “I thought I had made myself clear yesterday, but you thought I was not serious. Not showering properly after a run is offensive to those around you.” She stated.

Simon wanted to explain, saying, "I tried to, but—." Coach Sumner held up her hand and said, “I don’t need excuses; you have time to shower properly. So you have two options since you don’t want to shower on your own. One is that you will take one in the girls' locker room, where they can supervise you to ensure proper hygiene, or you will follow me into the coach's office, where you will receive a sound paddling for your disregard for direction. Which will it be?”

Simon stood there for a moment, starting to breathe a little heavier, then begged, “Please, I—”

“Choose, or we will conduct both in the girls' locker room.” Coach Sumner warned.

Another moment passed with tension rising, causing Simon to blurt out louder than intended, “The paddling!”

After Hope saw him masturbate and then mock him this morning, he wasn’t quite ready for even more embarrassment. Simon felt like the part of him that wanted this was gone…for a moment. He was curious about what it was to be spanked or paddled, as he's generally a good kid and has never been spanked in his life.

Coach Sumner and Simon walked to the coach's office, Simon keeping his head down like he was heading to his execution, each step bringing him closer. Upon entering, he glanced at his camera hidden in the office, pretty sure it was still recording. Coach Sumner and he were the only ones in there today, all thanks to Coach Marvin assigning the other coaches to the pool to set up for a meet. Coach Sumner closed the door, shut the blinds, and grabbed the paddle. Simon thought, “We’ll have to fix that for next time.”

“Remove your pants and underwear, then bend over the back of the chair that is in front of the desk.” Coach Sumner ordered sternly. Simon turned to the chair and took off his pants and underwear, giving the coach only the view of his butt. Simon leaned over the chair and grabbed the seat to hold steady, giving a perfect target for the coach, then closed his eyes with anticipation. Not having to wait long before the first WHACK. It didn’t disappoint in what Simon thought would happen, though I did hurt more, which was not expected.

WHACK, WHACK, Simon was crying by the third hit. Coach Sumner did not wish to provide Mr. E with any justification for disclosing the footage of her relationship with her boss. Her career and family would suffer as a result. So she held nothing back, and in total, he gave Simon thirty smacks with the paddle. His butt was bright red, and when he was told he could stand, Sumner smiled as he tried to rub the stinging out of his butt while displaying his little penis. Simon then placed his underwear and pants back on, only to be interrupted when he was about to leave. Coach Sumner stopped him. She could in good conscience let him leave smelling like that. “Simon, I can’t let you leave in your state; come with me to the girls' locker room to shower. The girls will already be gone.” Coach Sumner stated and directed him to the showers.

Having never been in the girl's room was weird, but she was correct about it being empty. Coach Sumner walked around the locker room, and when she was comfortable, she walked back to Simon and said, “Strip and give me your clothes; I will find something for you to wear.” Simon's eyes widened in surprise and pause. “Or do you need another reminder to follow directions with the paddle?”

That did it; Simon removed his shirt, shoes, socks, pants, and underwear while Sumner started the shower and watched in amusement. Simon walked into the water, happy to not have to go home smelling of urine. Simon tried to hurry as he didn’t want to accidentally have a girl pop in, but when he attempted to leave early, Coach Sumner said, “If you don’t slow down and wash properly, I will bring the paddle back.”

She left while he finished washing, and then Simon turned off the water only to realize that there was no towel to dry off with, and worse, because this was the last class of the day, the swim team and soccer team should be showing up soon. He just stood there in the shower room, air drying, waiting for the coach to get back. Thinking about how embarrassed he would be if the girls were to walk in and see him naked… And now that thought came to mind, his little penis became stiff.

“Luckily,” Coach Sumner came back before anyone else showed up. All she could find was a jockstrap from the high school equipment, which would not cover his butt at all. Some discarded soccer shorts from one of the elementary school teams, completely showing off his legs, and a school soccer shirt from last year, also from the same soccer outfit. He thought he looked like a child who chose to wear his old soccer uniform, which he grew out of. Coach Sumner placed his clothing from today into a plastic bag and told him he needed to get going as it was close to pick-up time. When they left the room, the coach headed to the pool hall to verify everything was in place. This gave Simon time to run into the office and not only swap out the camera but also move it to the top shelf for tracing purposes.

He made it to the pick-up prior to his mother arriving, and oddly to him, she didn’t ask about his outfit. Mrs. Sophia Fulton just assumed that there was an accident during school and there would be an email from the school explaining it this evening.

Mom had to make a few stops before heading home, and Simon was pretty quiet. Today's events were harder than he originally anticipated as he thought, “That was horrible the way I felt when Hope openly mocked me after I was forced to masturbate in front of her. Being toilet bathed and then pissed on was disgusting, not to mention some had gotten in my mouth. I am going to have to rinse my mouth out when we get home. Then the paddling hurt way more than I thought it would, and finally to have to strip naked in front of the coach and shower in the girls locker room; maybe it would be a good thing to stop while I can, before things get out of hand. Doctor Marjory, Coach Marvin, and Sumner would probably leave me alone, but Jay, Mike, and Grant—they would take time to stop, and with how Jay talks, it might be a while. I’m not sure about Hope; what she has done so far are things suggested by me. But now that she has felt the power, what might she do?”

Simon and his mother discussed how school was going, what they should eat for dinner, and any snacks he might want as they strolled around the grocery shop. It really cleared his head on the situation, and when he got home, he helped unload the groceries and then headed for his room to upload the videos and finish his homework. He thought about the situation and felt that even though today was terrible, it was one of the best he’s had so far. Plus Mr. E is wanting more misadventures.

His parents were going on a business dinner tonight, so his dad made Simon a chicken parmesan that he could heat up later. With them gone, Simon was able to tear apart the video without having any interruption and now had leverage on the whole PE staff, thanks to yesterday's and today's video. With the desks facing the door, apparently Coach Miles has a camera in the girls' locker room and chose to lock it up yesterday to view said footage. I wonder what he’ll think of today's action. Coach Liliana, being the head soccer coach and assistant to the football coach as well, is also a compulsive gambler who appears to be rigging her games. Knowing that a coach had an additional camera, Simon went in search of how to locate these devices and ordered the equipment. I can claim it's for school, not entirely a lie. Then he brought up his email and began his plan for tomorrow. Let's finish out the week with a bang.

Incoming email

(Jay)



Mr. E

That was awesome; good to know the coaches are under your control. Mike nearly had a heart attack when Coach Marvin showed up. Here is the video of Simon; I hope it is to your satisfaction. Can’t wait to hear what's next.

Sincerely,

Jay



(Hope)

Mr. E

I thought you might find this entertaining. Being forced to do something against my will bothers me. How can you harbor such resentment for someone and use it to your advantage?

Hope

End Transmission

Simon uploaded the video into the Flash while eating his dinner and then typed out his response and directions.

Outgoing email

Hope

Congrats on your success in showing your control over Simon. Thank you for the video. As of now I will not require anything of you today, but know this: going forward I would like you to keep me in the loop of any activity you share with him via a video log. Outside of PE, he’s yours to have fun with, unless I tell you otherwise. Remember to be creative, be commanding, but most of all remember he’s your plaything now. Regarding harboring resentment for someone to the extent of torturing them, this requires commitment, proof, and the capacity to capitalize on it.

Your Friend,

Mr. E



Jay

You guys did a fantastic job peeing on him and giving him a toilet bath! You guys have probably figured out by now that I'm now in control of Coach Marvin. By tomorrow, I should have the other coaches as well, so unless you disobey, in which case they will be happy to discipline you all. Bullying Simon in the locker rooms and PE shouldn't get you all into any difficulty. I don't recommend pursuing any of the others at this time.

Let's remain in the locker room for the time being. Let's make Simon miserable before the weekend begins, as it's Friday tomorrow. After gym class, the two of you should use your towels to whip his butt, back, and balls while he's nude. Make sure to continue until he starts crying uncontrollably. When you're finished, you're supposed to tie his feet together and his hands behind his back to the shower post to prevent him from moving. Leave him there. Coach Marvin will assist with what is needed to tie him up.

Sincerely,

Mr. E



Coach Kyle Marvin

You performed admirably; in fact, I have the film to show that you went above and beyond what I asked of you. The only precise task you have for tomorrow is to ensure that everyone can finish their assigned task and provide the boys with a means to secure Simon. The boys ought to tie Simon up after giving him a little whipping with their towels. Ensure that Simon is unable to escape. I would suggest giving a justification for keeping Simon after school.

As you will deduce, I now have all the coaching staff under my direction. So your role as head coach is to ensure staff and students are completing their tasks. The task for tomorrow:

Coach Taylor Weatherby will conduct a “Health” class tomorrow at the beginning of PE.

Coach Jason Miles will apply clothespins to Simon's nipples while he is tied up.

Bradley Starr is to apply Icy Hot to Simon’s genitals.

Coach Vera Liliana will slap Simon’s stomach until it is bright pink while turning the clothespins.

Coach Rebecca Sorenson will spank Simon, bare bottom, before releasing him.

Good luck,

Mr. E



Taylor Weatherby,

I would recommend looking over the footage before it is released to the proper authorities. This would not only destroy your career and reputation; this also comes with a prison sentence.

Let's start with the reason I'm reaching out to you now that I have your attention. I don't want to share this, fortunately for you. What interests me is making Simon Fulton's life miserable. Tomorrow in gym class, you will force him to kiss Ted Blanton's two unshod feet. You will also force him to kiss both of Grant Dixon's hands. You will force him to kiss Mike Simpson's cheeks. Furthermore, you will force him to kiss Jay Charles' mouth. That will conclude the lesson. There will be more tasks to come later.

Sincerely,

Mr. E



Jason Miles

From the image/video attached, you can see evidence of you recording the girls' locker room via your computer. Not only illegal, but it will end your academic career permanently. So you have two options: one is going to jail and losing everything you have worked toward, or two, follow my direction from this day forward until I have no use for you. That being said, to prove your commitment, you are to send me the video that you would have found on the same feed on your computer of Simon Fulton showering in the girls' locker room. This will remain between us; you will find out more from Coach Marvin. Tomorrow, after the last period, when the rest of the students have left the gym, you will find Simon tied up in the boys locker room. You are to place clothespins on each nipple and leave; do not assist him with anything else.

Sincerely,

Mr. E.



Bradley Starr

You can see that I have you on video taking steroids. This would result in the loss of your athletic scholarship and your ineligibility to play for the remainder of the season. Given your grades, you'll probably lose any hope for a bright future. However, if you follow my instructions going forward, I won't divulge what I know.

Tomorrow, before practice, you will find Simon Fulton tied up naked in the locker room. All that is needed from you is to apply Icy Hot to his genitals and leave him. Simply enough? There will be more to come, so keep in touch.

Sincerely,

Mr. E.



Vera Liliana

After reviewing the video and phone call, you can see how this can affect your career. Crestwood Private School may not be the top private school in the states, but I’m pretty sure that coaches are prohibited from betting on games, and even more offensive is rigging said games. This will end your career with any private school, and you will never be able to coach in the league.

Let's talk about what you can do to prevent this from going to the board now that I have your attention. I want to rig a game, just as you do. The objective of the game is to completely overturn Simon Fulton's world. Your task to keep this video and anything else I pull up about you from coming to light will be to follow my instructions when I send them. Your first task will be during football practice; you are to go into the boys' locker room, where you will find a tied-up Simon naked. When you get there, just give Simon's belly a good slap until it’s bright pink. While you’re at it, keep turning the clothespins on his nipples, but don’t take them off. Once you’re done with that, you can head out.

Sincerely,

Mr. E.



Rebecca Sorenson

Apparently, you don’t mind administering drugs; the video shows in great detail this fact. Well, at least you will have a career to fall back on once you are out of prison, as coaching will no longer be an option. Or…you can do the tasks I send your way, and I will not send this to the board and let them handle it. For starters, I will need you to administer some discipline to Simon Fulton, my real target.

Simon Fulton will be found in the locker room, naked and bound, following football practice. Make sure to spank him hard; as you administer 100 spanks with your hand, you can then set him free. If you are worried, just wait till morning and Coach Marvin will explain things.

Sincerely,

Mr. E.

End Transmission

Simon made sure he covered everything by going over all of his emails and notes. He wanted to kick off the weekend in style by making tomorrow extremely difficult. Paddling today demonstrated that he ought to expect that it will hurt more than he anticipated and that it doesn't take much action to make him cry. He wondered which would hurt more or less—the whipping, the paddling, or the spanking. On top of that, Hope's experiment with the clothespins proved they would become part of the fun. Though how all this will feel with the Icy Hot on his penis and balls and the pink belly will be interesting. Just thinking about it was giving Simon a tingly feeling in his stomach.

He was interested to see how Coach Weatherby would present the health class. The idea of doing things with other boys did not bother Simon because he considered himself bisexual, but having to do gay actions in front of people is practically a dream come true. Furthermore, obtaining video footage of him in the ladies' locker area would provide additional damning proof against Coach Sumner.

Getting late, Simon removed his shirt and shorts and took his dishes to the dishwasher. Wondering what it would be like to be completely naked walking through the house, forbidden from wearing clothing or maybe not having clothing in his room. Simon’s tight underwear was tented out as he walked into the kitchen. Once the dishwasher was started, Simon looked around, pulled down his underwear, and walked around the house for a bit, then headed for a shower and bed. Dreaming of what tomorrow will bring. Good night. I am off to my sweet nightmare.








   
   
(End of File)