Simon Blackmails 1 and 2

By Arclos

The author prefers not to display any email address. Please direct any feedback to [email protected] and it will be forwarded

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This work is intended for ADULTS ONLY. It may contain depictions of sexual activity involving minors. If you are not of a legal age in your locality to view such material or if such material does not appeal to you, do not read further, and do not save this story.
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Chapter 1

Simon Filcher was sick and tired. To be more specific, he was sick and tired that his fantasies weren't coming true nor would they. You see, Simon wasn't a very normal eleven-year old kid. He was brighter than most kids his age, sure, but that's not what set him apart. It's that upon discovery of what he could do with his penis, he had quickly learned that he had a very specific fetish. He liked the idea of being embarrassed in front of a whole bunch of other people, the idea of being dominated, the idea of being spanked for minor misdeeds.

He looked at himself in front of the mirror: as naked as he was skinny. His blonde hair, his large brown eyebrows, his brown eyes...he thought he was fine looking for his own age. He looked down at his erect penis. It wasn't a large one: he knew from spying on other boys in the locker room he was actually pretty small down there. Most kids would have been frustrated over that. But Simon? He liked that about himself.

Still, it wasn't enough. Most of the other kids never teased him about it. Heck, he wasn't even the smallest in his class. That was Ted Blanton. Ted was a chubby kid with black hair and black eyes. He was teased a bit for being a bit of a nerd but beyond the occasional pantsing (exposing Ted's tighty-whities), it never escalated to the point where Simon could live vicariously through Ted. Plus in Simon's fantasies, he was always being forced to suck Ted's dick against his will. Ted wasn't the only kid, mind you.

Simon had worn boxers at the beginning of the school year but he quickly learned that tighty-whities meant getting picked on by other kids. So he switched. Only to his disappointment, maybe because the kids liked him that much, it didn't lead to anything more than comments that he should go back to boxers so they wouldn't have to see his thighs. That of course was a problem. So even though he fantasized that they would kick him out of the locker room in only his underwear (or even better: naked) they never got close. They didn't even pull his gym shorts down even though he never tightened them to make it easy on them.

Simon grabbed his penis. He was getting ready to masturbate again, for the third time that day. He was getting ready to have a fantasy where a teacher would not only make him strip naked in front of his whole class, hands over his head, but that he'd get a spanking followed by having to suck a random boy's penis. The choice would be up to Simon. Fake Simon, of course, always picked the boy with the largest penis. The one who would in theory mock him the hardest, who could likely already generate sperm he'd have to swallow.

But then Simon stopped. He was after sick of it. Sure, there was a part of him that knew it was just a fantasy and it should stay that way. But, he was eleven and as smart as he was, he wanted the real thing. After all, if the fantasy brought him so much pleasure, wouldn't the real thing be even better? So Simon made a decision: from now on, he would only masturbate if someone ordered him to do so. It was hard but Simon moved his hands away from his penis.

But how would he accomplish this? How would he make his fantasy turn into a reality? In most of the stories he read, it was set in the sixties. But it's 2016. How could he get the kids in real life to act like the kids in the stories?

And so he thought. And he thought. It actually took him several days but then he had an epiphany. Sure, it wouldn't be ideal. In his fantasies, blackmail was sometimes a part of it. Sure, he liked it when he didn't have a choice because authority figures made him but he also liked the idea of kids forcing themselves to have authority through blackmail. But he could cheat. He could blackmail some people to making him live out his fantasies. Of course, they wouldn't know that Simon was the one blackmailing them.

The first thing Simon did was draw up a list of potential blackmail targets.

There was his mom and his dad. Of course, he'd have to blackmail both of them but as far as he knew, his parents were perfect. (They weren't but Simon was still in the stage where he idolized his parents) He didn't think this was realistic. Still, he wrote down that he could take one of their credit cards and buy a few things like a paddle. If he was caught, he'd have to make some kind of excuse, but still. He was sure he could get away with it.

He then wrote down the names of the boys who bullied Ted. They've already shown a willingness to be cruel and he did have something on them: a secret video of them taking turns kicking Ted in the balls in the name of testing to see if he had any. Sadly, Ted was fully clothed, but Simon had pretended he was a naked Ted as they had done that when he first took it. They were Grant Dixon, Mike Simpson, and Jay Charles. Grant was the big kid of the class with black hair and black eyes. Mike had blond hair and blue eyes. He was a little shorter than Grant. Jay was a lot shorter, had red hair and brown eyes, and freckles all over his body. They were kinda dumb but he could leave detailed instructions for them. Still, he'd have to have multiple sessions with them (slowly building up evidence) before he got to the sexual bits. And Simon wasn't sure he could be that patient.

Finally, he came up with the name of one girl who he knew had a grudge against other boys. Hope Simmons. Hope was an eleven-year old girl who came from a broken home. From what Simon knew, her dad had hit her. She'd been holding a grudge against boys ever since then. Simon didn't think she'd participate willingly but she'd enjoy it once she was blackmailed into doing it. He would need to find something on her.

Finally, he went down his teachers. He would have to find really big things if he wanted to get them on board. But he figured he eventually would.

Once he was finished with the list (it took him several hours), he decided to start putting it in motion. He created an anonymous e-mail ([email protected]) through a proxy server. He got the e-mails of Grant, Mike, and Jay and sent them the video of them kicking a boy in the balls. He threatened that if they didn't do what he said, he'd send it to the principal. This is what he sent them:

Dear Boys,

As you can see in the attached video, I could get you three in a lot of trouble. After all you are clearly assaulting this boy multiple times and for fun. This wouldn't just get you kicked out of the school: it could get you sent to juvenile detention. Now lucky for you, I don't care to run your life. I care to ruin Simon's life. So if you follow every task to the letter, I won't send the video.

Tomorrow you guys must during gym class pull Simon Filcher's shorts down.

Good luck and don't get caught! Make sure to get me evidence.

Sincerely,
Mr. X

He sent the e-mail. He was getting hard, thinking about how embarrassed he would be as girls around him saw his underwear.

After doing homework and playing some video games, he checked his new secret e-mail. These were the three replies he got:

The first reply:

Mr. X,

This is blackmail! If I ever find out who you are, I'll beat you up.

But as long as you don't reveal the video, I'll do what you ask. I'm going to pull his shorts down.

Sincerely,
Grant

The second reply:

Mr. X,

I never really liked Simon. So don't worry, I'll play along.

I discussed it with the guys and convinced them this was the right thing to do. I'll be sure to take a video of Simon's gym shorts being pulled down.

Sincerely,
Jay

And the final reply:

Mr. X,

You are lucky that Jay convinced us to help you: I wanted to go to the police but he seems to think we'll have some fun so whatever.

I'll be distracting our coach so that we don't get in trouble.

Sincerely,
Mike

And with that Simon smiled. He couldn't wait for Grant to pull his shorts down! Plus, if he's lucky, his penis will be erect adding to his own humiliation!

Simon also set a task for himself. Tomorrow, he's going to start gathering evidence on Hope. She couldn't be perfect...

Chapter 2

Simon couldn't believe the day he had. He had began the day by slowly stalking Hope to see if there was anything she was doing so he could blackmail her. Sadly she seemed like the perfect eleven-year old girl. She even studied during study hall instead of goofing around like every other kid. Simon thought that he might have to wait days or even weeks before he would find any dirt on her. At least he couldn't wait until the last period of the day: his last class was gym class. Admittedly, he was nervous that he knew his shorts were going to fall and girls would see him in his underwear. He even thought about calling it off during his lunch break. Who knows why he went ahead with it? Maybe it's because he hadn't masturbated in days but he was pretty horny. And being horny was clouding his judgement so he decided to go through with it.

In the locker room before gym class, he quickly switched to his gym uniform: a white t-shirt and black gym shorts. He made sure not to tighten his shorts like always. He then went to the gym. He wondered when they would do the deed. Soon gym class began. They did some stretches led by a boy and a girl. All he could think about was that if he was the one leading the stretches, that would have been the perfect time to pull his shorts down. After all, all eyes were on the two kids. But he was near the back during the stretches.

The gym coach, Coach Weatherby, then announced it was a free day so they could pretty much do whatever they wanted. Some of the boys started playing basketball, some of the girls started jumping rope, and other kids just walked around talking. That's what Simon did. He walked around. He made sure to stay near the girls. After all, he wanted them to look at him.

At last, it was nearing the end of the period. Mike went over to Coach Weatherby and gave him a grand story about how he went to the bathroom only to see poop everywhere. So Coach Weatherby followed Mike out of the gym. Simon could only think: it's happening! He kept his arms at his side. Jay got his cell phone and pointed it at Simon. Jay's clearly recording a video. Grant walked up to him. He put his arms around Simon, almost as if to trap what Grant thought was an unsuspecting kid they were about to pick on for the first time.

Grant then whistled, getting the attention of every kid in gym. “Hey guys! Let's see Simon's underwear!” Grant yelled as he pulled Simon's shorts down all the way down to his ankles.

Simon froze. He could feel every eye on him. They were looking at him: at his tighty-whities! His face quickly grew red. He was mortified! It didn't help that all the kids were laughing at him: some pointed out he was wearing dumb tighty-whities, others just because they saw him in his underwear! After five seconds, Simon pulled his shorts back up.

It didn't take long for the kids to move on. Simon moved to the corner of the gym to be alone. He was conflicted. On the one hand, that was the worst moment ever of his life. On the other hand, he was so turned on. He had been lucky (or unlucky depending on which side of Simon you ask) that he hadn't gotten an erection until after he had pulled his shorts back up and moved away from the kids. He wondered if that should be the only task but he knew it was futile. He wanted to take it way, way, way farther than this.

After gym class, he took a shower and switched back to his normal clothes. He then rushed to find Hope. He followed her to the high school. What was she doing there? At the high school parking lot, he hid in bushes as he saw Hope talk to some high schoolers. It felt shady for some reason. For some reason, Simon felt compelled to record this moment so he took his phone and started making a video. To his surprise, he caught Hope on tape handing a plastic bag of marijuana over to a high school boy in exchange for some money.

He had just caught perfect little Hope selling some drugs! This was perfect! Sure, their state had legalized marijuana but only for adults. What she did was illegal. Simon smiled. He quickly escaped.

That afternoon he went on the computer. He knew he had two e-mails to send: one to slowly escalate things with the boys and another to start with the girl. He knew Hope wasn't in his gym class so he knew that she had yet to see him in his underwear.

He did get an e-mail from Jay:

Mr. X,

Attached is the video you wanted. I guess it's up to you if you want to share it but you'll get Grant in trouble.

Sincerely,
Jay

He clicked the video. In full HD glory, he saw himself standing there super embarrassed with his shorts down. He wanted so badly to masturbate to that image of himself and his shirt barely hanging over the top of his tighty-whities. But nobody had given him permission so he desisted.

Anyways, the first e-mail was to Grant, Jay, and Mike.

Dear Boys,

You did a great job on the pantsing job. Of course, I now have even more video evidence against you guys.

Your next task is simple during the locker room before gym class. While he's changing from his pants to his shorts:
1)      Grab and pull his underwear up.
2)      Keep pulling until his underwear rips.
3)      Grab what remains and during gym class, show the pieces of underwear to girls.

Good luck and make sure to get a video of number 1 and 2!

Sincerely,
Mr. X

Simon smiled as he gave these instructions. He had given himself some wedgies before so he knew they hurt: he knew that in order to rip the underwear (forcing him to go commando and revealing his penis to the boys) it would hurt a lot. Plus the idea of girls having pieces of his tighty-whities (which would likely have some poop stains from the wedgie) was very embarrassing to him. After all his underwear is supposed to be very private.

It didn't take long for the boys to reply.

Dear Mr. X,

Fine. This time I'll be taking the video though. I'll also get some pictures of the girls holding the pieces of tighty-whities.

Sincerely,
Grant

The second reply:

Mr. X,

Oh, I like this. I'll be the one to give the loser Simon his wedgie.

Sincerely,
Jay

And the final reply:

Mr. X,

Jay seems pretty excited about this. I don't know but I'm going to help with holding Simon during the wedgie so he doesn't resist.

Sincerely,
Mike

Simon smiled. This was perfect. Finally, he sent his last e-mail:

Hope,

I have a video here of you ILLEGALLY selling weed to a high school student. Now lucky for you, I'm not interested in making your life miserable. That honor belongs to Simon Filcher. That will send you to juvenile detention unless you follow my tasks.

My first task is simple. A test. Tomorrow after school, you are to find Simon Filcher, force him into a room, and pull his pants down. He should be commando. Have him put his hands over his head (if he refuses, threaten to just take his pants with you.) Take a picture of him. Then send it to me.

Good luck.
Mr. X

It didn't take long for Hope to reply.

Mr. X,

I don't know who you are but I will do my best to find out. When I do, I will make sure that you suffer for trying to blackmail me.

But don't worry. I don't want to go to juvenile detention so I'll do what you ask even though it's gross.

Sincerely,
Hope

Simon's heart started racing. Tomorrow he was getting a wedgie, pieces of his underwear would be handed out, and Hope was going to see his penis.

Simon couldn't help but smile.

(End of File)