Simon Blackmails

Simon Blackmails 7

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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That Sunday, Simon woke up. He knew that he had a day of blackmail in front of him but it was Monday he really couldn't wait for. If everything went according to plan, it would be his best worst day ever yet. Of course, he still had to make sure it happened and the first thing to do was get the school board on his side. He also had to keep Ted happy by going after his step-father. He had no idea why Ted demanded this. Simon figured that Ted probably a raise in the allowance or to be able to stay up late at night. It didn't matter to him.

Simon went downstairs, without putting any pants on so it was just his shirt and underwear, and found breakfast waiting for him. His parents had a day of errands to run so it didn't take long for his mom and dad to leave the house. It was a bit weird seeing them after what he had learned: his mom stealing top classified secrets, his dad embezzling money. He had mixed feelings. On the one hand, it meant he could blackmail them and he could extend his “misery” to his home. On the other hand, it meant his parents weren't perfect but ordinary human beings. He did wonder what his parents were thinking.

Once he finished breakfast, the door bell rang. Simon answered the door: it was Ted! Ted looked down and saw that Simon wasn't wearing any pants. “Simon, I think you forgot to put on pants!” Ted yelled in surprise. Simon shrugged as Ted came inside.

“Sometimes I don't like to wear clothes when I'm supposed to be home alone. I didn't want my parents think anything was weird. I can't have them suspect you were coming over otherwise they'd know what we planned to do.” Simon lied. It's true, he often was undressed in some capacity when he was home alone and with his parents but he was also often fully dressed.

Ted bought the lie. The two quickly went to Simon's room. Ted noticed that even though Simon could have put on pants, he chose to instead try to cover by bringing his shirt down. It didn't completely do the job and Ted could clearly see Simon had grown an erection. Ted was a bit uncomfortable by this but he decided to just ignore it for now. If Simon didn't want to wear pants, he wasn't going to press the issue, risk upsetting him, and thus fight with his new friend.

He did stare maybe a little too long at the erection. He was a bit jealous of it as well. After all, when erect, Ted was as big as Simon's soft penis.

Ted went over to Simon's computer after a few minutes of silence. He turned it on. “So I have some good news. There are six school board members. I already found just by hacking their computers dirt on three of the board members. That means we only have three left.” Ted told Simon.
“Wow, you already have dirt I can use?” Simon asked, impressed by Ted's skills.
“Yeah you'd be surprised what people keep on their computers. Like e-mails blackmailing people to embarrass and hurt him.” Ted replied. Simon did smile at this, although one that showed he was proud and ashamed of this.

Ted brought up the school district website. He noted the six school board members:
Anthony Phelps, a bald man, probably in his forties, who ran a major factory that kept most of the people in the community employed.
Marcus Oran, a black man in his thirties, a filmmaker by day, a political activist by night.
George Crane, a man in his fifties, respected, the owner of most of the real estate in the town.
Samantha Korn, a woman in her sixties, a veteran teacher. The students say she's the reason the school board has yet to actually ban spanking a child as official punishment even though it hasn't happened once since the early eighties.
Mary Beth Elle, a woman in her thirties, derided by some as a trophy wife, she is also the head of the PTA.
Margaret Heart, a woman in her late twenties, a young lawyer.

The only one Simon saw on a day-to-day basis was Samantha Korn, his math teacher. She liked to taunt him. Simon just knew that he was going to have to get her to paddle him one day-probably this upcoming week!

Mary Beth Elle was the mother of a pair of twins: Mark and Ella. They were in the eighth grade. Ella was the head cheerleader of the middle school, as popular as she was pretty. Simon knew that she could also be mean to other female students. In many of his fantasies, Ella had stripped him in front of the cheerleading squad and forced him to do cheers. Who knows? Maybe Simon could make that happen. As for Mark? He was a tall basketball player who was liked by everyone. Simon had met Mary Beth a few times. She was always nice to him but his mom always thought of her as strict, cold, and a bit of a bitch. He knew this because his mom would never stop complaining about Mary Beth.

He wasn't that familiar with Anthony Phelps or Marcus Oran. He had met them a few times and he knew they were powerful and influential people. If he had them under his thumb, he would control a lot of the real power behind the town. Of course, Simon would only have one real interest in using that power:

He had never met or heard of Margaret Heart.

Ted then moved on from that as he put in a flash drive and downloaded files into the computer.

“Okay, so you know Marcus Oran? You know his whole speech to the whole school about how we shouldn't steal movies and TV because it's illegal and he knows people who lose money when you do it?” Ted asked.
“Yeah.” Simon replied.
“It turns out that he's the owner and operator of a large file sharing network. They don't just share normal blockbuster movies but also porn-even porn involving minors. Like sixteen year olds. Very illegal.” Ted told Simon as he showed him evidence.

That was surprising. Marcus was always very spoken against file sharing networks, arguing they were a danger to independent filmmakers like himself.

“I can use that. Against the law and it would destroy his reputation. Something like that, Marcus will do anything to keep the public and law from finding out.” Simon said. He smiled. He knew exactly what he could ask Marcus to do as a test.

“Okay what else do you have?” Simon asked.

Ted brought up evidence against George Crane. It turns out that George had sent e-mails telling his landlords not to rent to black people, making up an excuse about credit and stuff.

“He doesn't want to rent to black people? Okay, so he's a racist.” Simon said.
“Not just a racist. He's breaking the law. I know, I checked.” Ted told him.
“Ah, so perfect blackmail material. Great!” Simon replied.

Finally, Ted opened up the files showing a video of Mary Beth Elle stealing money from the school. It's night, it's clear she's not supposed to be there as she's very jumpy, and quickly rushes.

“I checked the school's spreadsheets. That money is supposed to be going to the science department for new lab equipment. Lab equipment that the Head of the Science Department didn't think we needed and that she pushed through.” Ted explained.

“This is perfect.” Simon said. “Okay, so we still need compelling evidence of Samantha Korn, Margaret Heart, and Anthony Phelps.”
“I don't know enough yet about Margaret. I think we can probably find something with Ms. Korn at school. But Phelps? I know where he's going to be today. At the country club.” Ted said.
“Okay, but my family hasn't joined. How am I supposed to get in there?” Simon replied.
“I have a way in. I would say you wouldn't like it, but knowing you, you actually might.” Ted promised.

So Simon put on pants and the two made their way to the country club. Simon didn't have a bike of his own so he had to ride in Ted's bicycle. It was quite a funny sight: a skinny pre-teen grabbing into a chubby pre-teen on a kid's bike! They almost fell over a few times but in the end, they made it.

Ted took them away from the country club's entrance and to the back. Simon had to hold his nose. There was a fence. Simon immediately saw there was one way in. There was a trench that run beneath the fence. Only it was full of dirty, disgusting sewage water.

“I know a kid, a cousin my mom makes me hang out with sometimes,, who sneaks in all the time. He says that as long as you don't go inside the clubhouse where the offices are, everybody assumes you are supposed to be on the grounds. He goes swimming, plays tennis, and a whole bunch of other stuff. I've gone along with him a couple of times but I always hate the getting in and out part.” Ted said.
“Our clothes are going to get dirty. Plus we're going to smell.” Simon pointed out.
“My cousin keeps a bag of clean clothes next to the dumpster for a reason. Also some soap.” Ted replied. “Don't look.” Ted asked.

Even though in the locker room, Simon had already seen Ted naked, Ted was still embarrassed to strip in Simon's presence. When Simon turned around, Ted did the same so neither boy was looking at each other. The two quickly took off their shirts, socks, and shoes. Simon didn't hesitate to take off his pants, Ted did. They both hesitated to take off their underwear.

“Okay, I'll go first. I'll tell you when to cross. Remember not to look.” Ted said.

Simon did as he was told. He heard Ted get in the water, swim to the other side, and get out. He heard Ted take out a plastic bag. He heard a faucet turn on as Ted washed himself. He could have sworn he heard Ted whisper a curse. A few seconds later, Ted gave Simon permission to turn around.

When Simon did, he noticed Ted wasn't looking at his direction. Ted was wearing sandals, a bathing suit and a shirt.

“So I have some bad news.” Ted said.
“What?” Simon replied.
“Every now and then my cousin takes his clothes home to wash.” Ted replied.
“It's okay. I'll just throw my clothes over the fence.” Simon said.
“You can't! There's barbed wire at the top and the fence is too tall!” Ted pointed out.

Simon knew that was true.

“Okay, well, we'll have to make do.” Simon said.

Simon crossed the trench. It was very disgusting but Simon got through it. Once he was on the other side, he quickly washed himself using a faucet that was off the side of the building. Ted kept avoiding looking at him.

“So what are you going to do? You can't just go around the club's grounds naked. You'll get thrown out or arrested.” Ted said.
“Where's the lockerroom?” Simon said.
“It's not that far.” Ted said. “Right now we're behind the main clubhouse building. The northern path will take us to the pool and the lockerroom is on the other side of it.”
“Okay. So why not go to the lockerroom and see if there's anything I can wear?” Simon asked.
“All the clothes are going to be under lock and key in a locker! Plus someone might recognize you are wearing their clothes.” Ted said.
“That's fine. Just bring me a towel. We'll have to make sure it doesn't fall.” Simon said.

So Ted left. Simon wondered if someone else-like an employee-would catch him naked. He had no idea what he would do then! It would be so embarrassing especially if the employee decided to drag him through the clubhouse naked! He had no idea how he would explain this to his parents-or the police if they were called! He could be naked, handcuffed, for all to see in public as he went to jail! Just thinking about it gave Simon an erection.

It took ten minutes but to Simon it was an eternity filled with nightmarish daydreams before Ted returned with a towel, handing it to Simon while doing his best not to look at Simon's privates. Simon wrapped it around his waist. Now he just looked like a kid at the pool. Granted he was dry but going to the faucet fixed that!

They went through the club grounds. Simon had to keep his hands on the towel to make sure it didn't fall off! If they did, he might be caught as an imposter! And even if he wasn't found to be trespassing, someone would see him fully naked!

It wasn't long until they found Anthony Phelps. They saw him through the window inside the clubhouse (the one building they couldn't enter) having dinner at the nice club restaurant. Anthony was dressed in a nice suit.

Simon really wanted to go in but the club employees in the club might realize his parents aren't members-plus this was a fancy restaurant and he was wearing the wrong kind of suit-his birthday one!
Ted took out his phone and so they recorded from a distance. Nobody bothered them.

It turns out they didn't need to go inside to catch Anthony breaking the law. Once again, Simon proved to be incredibly lucky when it came to finding incriminating evidence. That's because on camera, Simon caught Anthony having dinner with an escort. Of course, they didn't realize this immediately so they kept recording him, even as he left the fancy restaurant. Through the windows they saw him leave the club with the woman.

“I wonder who he was meeting with?” Simon asked.
“Let's find out.” Ted said.

He took a photo still from the video he took and ran it through the internet. Using a reverse image search, he found a picture of the woman on an illicit escort service website.

“She's a prostitute! Anthony Phelps is all about family values but he's cheating on his wife and paying to do it!” Ted proclaimed.
“So there's our incriminating evidence. That's four votes on the school board we'll have.” Simon said.

They started walking back to the back of the clubhouse to leave. As they did so, a couple of beautiful teenage girls stood in front of them-one of them blond, the other a brunette. One of them recognized Ted!

“Oh, hey Ted, how are you doing?” Said the blonde.
“I'm doing good. How about you?” Ted replied to be polite.

The blonde took it as an invitation to talk at length about her life-talking about which boy she currently liked but how he was dating another girl but she thought he was also cheating on her with a third girl-for what seemed like a long time. She also spoke really fast so it was hard to Ted, or Simon, to keep up especially since they had no idea who any of the people in her story was.

As Simon stood there, he started to feel his towel start to slip. He started to panic. Would these hot teenagers see him naked!? What would they do!? He wanted to grab the towel but he was afraid that would call attention to it and they would want to know why he cared if his towel fell. They might take him away from it and see him naked!

These thoughts were of course starting to make Simon's penis get erect, which panicked Simon even more! There was no way the girls would miss an erect penis tenting the towel-or worse, slipping out! He tried to take his mind off it, but his towel slipped even further.

He was terrified it would happen and yet he hoped it would.

Right as he felt his towel was about to not just slip again but fall, the brunette mentioned they had to get to yoga class and the girls moved away from them. Simon quickly pulled his towel up. One more second and he was a sure goner!

Ted looked at him. “You know, your ugh, well wiener...it's hard.” Ted said.
Simon looked down! It was indeed hard! Luckily it didn't stick out from one of the folds but still! The girls probably saw it! Simon quickly blushed red. He guessed he was lucky the girls didn't say anything.

They quickly reached the back of the country club again. Their clothes, fortunately, were exactly where they left them. Simon handed the towel back to Ted. As Ted went to the pool area to return it, Simon swam back and put on his underwear. He waited in only his briefs for Ted to return, largely because he liked the risk of getting caught.

Nobody came to Simon's relief and disappointment. It didn't take long for Ted to return. He had Simon turn around once again as he stripped naked. Simon had a quick ugly thought about hiding Ted's clothes but decided against it. Ted after all had the real power here.

Ted hid the clothes and swam back. He quickly got dressed. “Man, you smell.” Ted said when he allowed Simon to turn back around.
“So do you.” Simon said.
“Well we can't wash ourselves until we get back to your house.” Ted said.

At that, Simon put his clothes back on.

They rode back to Simon's house. Simon's nose during the bike ride was right on Ted's neck so he smelled the sewage the whole time. When they got to Simon's house, his parents car wasn't in the driveway. They were as expected still running errands.

Once inside Simon's house, the two boys stood there. “Well we have to get ourselves clean and I might as well wash our clothes.” Simon said. Simon went to his room and Ted slowly followed.

Simon took off his shirt, his socks, and his shoes. He then looked at Ted. “Come on, I see you naked like every day in the locker room. It's no big deal.” Simon said.
“I know. I just...am not comfortable like you are.” Ted revealed.
“Oh, come on! I'm still embarrassed to be naked in front of another boy! I just like it, I guess, but still. It's only a problem if you make it one.” Simon reasoned.
Ted didn't budge.
“Well I guess you could go back home with smelly clothes and smelling bad. I don't know what your parents will think.” Simon said.
Ted knew that if that happened, he'd get a huge spanking. Every time his cousin had taken him to the clubhouse, that always happened when he got home. Ted took off his socks and his shoes. He gulped as he took off his shirt, exposing his chubby stomach he hated.

Simon pulled his pants and underwear off in one swoop, leaving him completely naked. Even though he was the naked one, it was Ted's face that turned red. He then turned around because he knew Ted would want the privacy. Before he knew it, Ted handed him all of his clothes: including his pants and underwear.

“Okay. Go to the bathroom and take a shower. I'll go put these in the laundry room.” Simon said. Ted went into the bathroom and closed the door behind him. Once that happened, Simon turned around went to the laundry room. He put the clothes in. Once they were washing, Simon went to his room. He looked but he didn't find anything that would fit Ted.

Once Ted was done with his shower and drying, he opened the door just slightly.
“I don't have anything for you to wear Ted. I'm too small.” Simon said.
“Oh, okay.” Ted said.
“I still need to take a shower.” Simon reminded him. “Come on, your clothes aren't going to be ready for at least another hour. We're friends, it's cool.”

Ted stepped out of the shower, wearing a towel around his waist. Simon went in to the bathroom. He left the bathroom door open as he took a shower.

After the shower, he found Ted was still in his room, just sitting there not sure what to do. Unlike Ted, Simon wasn't wearing a towel in his room. He was also very erect. Ted turned his face away.

“Can I ask you a question?” Ted asked.
“Sure. You can ask me anything.” Simon replied.
“Do you...do you ever play with yourself?” Ted asked as his cheeks went red.
“Sure. I used to do it all the time. But I decided I can only do it now if someone asks me to and in front of them.” Simon said.
“Wow. So if I ask you to play with yourself, you'll do it?” Ted said.
“Yes.” Simon told him.

There was a part of Ted that really wanted to ask Simon to do that just to see if it was true. He was ashamed of that thought.

The two didn't really do anything for another couple of minutes. Suddenly, the washer's buzzer went off. Simon went and put the clothes in the dryer. When he came back, he was still rock solid hard.

“I know you don't want to...tell me to do stuff.” Simon said.
Ted nodded.
Simon sat next to him. Ted couldn't help but look at Simon's erect penis while at the same time trying to avert his view.
“Too bad. I'd do anything you told me to do. Even suck you off.” Simon said, taking a risk, hoping Ted wouldn't be too wierded out or anything.

Ted was so startled, he actually stood up! His towel fell and Simon got to see Ted's penis, close up. Ted quickly covered up with his hands.

“That's weird. Look, Simon, I like you but man you are weird.” Ted said.
Simon shrugged.

Ted was in a conundrum. On the one hand, he wanted to pick up the towel but doing so meant using one of his hands. Even though his genitals were so small that he only needed one hand, he felt like the extra hand provided extra protection from Simon's eyes. Plus going down to pick up the towel would put his own eyes right in front of Simon's penis.

“Why is your penis so small?” Simon asked. Simon had noticed! Ted's face grew red!
“It's...a medical condition. Once I'm older, they'll give me some shots to help it grow.” Ted said.
“Oh, well, that's cool I guess.” Simon said.
“You don't think I'm lame or a fag?” Ted asked, surprised.
“No. I like you how you are.” Simon replied.

Ted couldn't help but smile. Ted couldn't help but glance down and confirm that Simon still had an erection.

“Don't you want to relieve your own?” Ted asked.
Simon nodded. “You have no idea how bad.” He said.
“Okay....well...I guess...you can...you should....do it now.” Ted asked.
“Really?” Simon asked.
“Yes.” Ted said.

Simon's face grew as red as Ted's face as he put his hand on his penis and started stroking it. As Simon masturbated in front of Ted, Ted couldn't help but feel that his own penis was starting to grow! He was getting erect! He did his best to not move his hands as not to excite it but failed.

After a few minutes, Simon had a dry orgasm. “Oh, man, that was the best.” Simon said. Simon looked at him weird as Ted moaned, his fingers continuing to stimulate his penis. Ted didn't explain. He just sat down.

As Ted sat there, he started to think about how satisfying it would be for Simon to suck him. He was really hard, horny, and he really wanted relief. But he didn't want to masturbate. No way he could do that anywhere in Simon's house.

“You know....were you serious about sucking me off?” Ted asked. Simon nodded. “Okay I want that.”

Ted moved his hands out of the way. Simon couldn't believe this was happening! He was actually going to get to suck cock! It was a small one, granted. So small that erect it looked as small as Simon's now soft penis. But still!

Simon got on his knees in front of Ted. He kissed Ted's thighs so that his face would touch Ted's genitals. He started to lick Ted's penis. To his surprise, he thought it tasted fine. He then licked Ted's balls. As he did, Ted started to feel like he was in heaven. Sure, he was straight, but a tongue is a tongue! Soon he felt Simon's mouth go over his balls and his penis. As Simon sucked, Ted was so happy.

Simon sucked until Ted yelled out “Oh, yes! I'm cumming!” Ted's face went red as he said that. To Simon's disappointment, if not surprise, Ted was also a dry cummer.

Simon stood up as Ted covered up his genitals again. Ted noticed that Simon was erect yet again. Even though he was bashful, Ted told Simon to masturbate again right in front of him. He had no idea why he did it. Simon quickly complied. This time it didn't take Simon long to have another orgasm.

The dryer buzzer went off. Simon went and got Ted his clothes. Ted put them on. Simon stayed naked.
“Okay, so tomorrow we find dirt on Mrs. Korn.” Simon said.
Ted nodded. They said goodbye and Ted left.

Simon went to his computer. He had plenty of e-mails to send out. But before he started that task, he looked over what had just happened with Ted. He had no idea if it would happen ever again but he hoped so.

(End of File)