Simon Blackmails

Simon Blackmails 9

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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Grant Dixon woke up that morning. The biggest, and oldest as he had turned twelve first, sixth grader in his class stood up and took off his boxers. He looked at himself in the mirror. He was very proud of his penis: the largest in his class with a surprising amount of pubic hair. Puberty had hit him early and it had hit him hard.

He looked at his little brother who was sleeping in the bed across the room. Ray Dixon was a loser in Grant's mind. His pathetic sibling who had no chance of being as awesome as he was. There was a time, before middle school, when Grant had actually gotten along with Ray. Not anymore. Ever since his father had decided Grant was old enough to take care of the two of them a couple months ago. When he had left him in charge instead of spending money on a babysitter. Grant was in the sixth grade now after all.

Grant's father worked the late shift as a security guard at Anthony Phelps' factory. He went to work the minute the boys got off from school and didn't get back until they were deep in sleep. During the weekends, he went to the bars leaving his kids alone. As for his mom? Grant didn't know where she was. She had left without word one day when he was six and he had never seen her since.

His younger brother was only two years younger than him, in the fourth grade. Yet he still wore tighty-whities. Yet he was too young to enter puberty. Yet he still played with toys and watched cartoons. Yet he was a little kid.

Grant went into the shower and after he was done, he got dressed. He then went to Ray who was still asleep. It was now his responsibility to wake Ray up, to make breakfast, and then lead Ray with their bikes over to the elementary school next to his own school. His father never really checked up on them but he still did it. Sure, he loved to abuse his authority and he loved to make his little brother miserable for trying to hang out with him-with him, a middle school kid!-but he was still family. His family that he had to take care off.

When Mr. X had started blackmailing them, Grant hadn't just been doing the tasks with Simon but also with Ray. That first day, he had pulled Ray's shorts down outside the elementary school when he had gone to pick Ray up. It hadn't been the first time but still the laughter of kids at Ray had filled the air. That second day during the bike ride home Grant had them stop and he gave him a wedgie until his underwear ripped. To random girls he would show the ripped pieces of underwear. The third day when they got home, he stripped Ray down naked and gave him a golden shower. He didn't let Ray get dressed or take a shower for hours. Then on Friday he got home, he stripped Ray down naked again, and whipped him with a towel. Ray had cried for hours after that.

Yesterday he had made Ray ride to school in only his underwear. He didn't let him get dressed until he was outside the elementary school five minutes before school had begun. Ray was so embarrassed, he had started to cry and was shaking in front of the kids. Grant only made fun of him for that. He wasn't worried about getting in trouble: in the elementary school, the entrance the kids who biked to school was different than the one the parents used to drive their kids. The teacher who was supposed to watch that entrance was usually very hungover and didn't really pay attention, preferring instead to sit and nurse his headache.

That morning, Grant woke Ray up. As expected, Ray had been sleeping in only diapers. Ray was embarrassed by this but his brother made the ten-year old wear them under the threat of spanking. This had been going on for a couple of weeks before the business with Mr. X started. Ray lay down as Grant removed the diaper. He looked at the brown-haired little kid. He had brown eyes and eyebrows. His small little button nose seemed to match his little button penis and balls. Grant grabbed the balls and squeezed them. Ray screamed in pain before Grant let go, smiling cruelly at him.

“How did you enjoy going to school in only your underwear?” Grant asked him.
“It was my worst nightmare come true.” Ray told him. He knew better than to lie.
“Yeah, well I hope you like nightmares. From now on, every day, you are going to bike to school in only your underwear.” Grant told him like he was Ray's dad telling him to brush his teeth.
Ray opened his mouth as if to protest or beg.
“If you say anything more than “yes, brother” then guess what? I'm going to spank you. Then not only am I going to make you ride to school in your underwear, I'll also make you ride back from school in only your underwear. And instead of just wearing a diaper to bed, I might make you wear a diaper all the time.”
Grant could see in Ray's eyes that he was processing the threat. He seemed to realize that Grant wasn't bluffing. If that happened, the remaining friends Ray had wouldn't talk to him. Grant then saw Ray look at the direction of his dad's rooms. He knew what Ray would calculate: his dad would spank him for waking him up since the house wasn't on fire. Then he'd spank Ray again after Ray told him. Every single time Ray had done that the first couple weeks of school when Grant teased him or bullied him, their dad had simply said boys will be boys and Grant was in charge. Then Grant would spank him a third time plus carry out the rest of his threat.
“Yes, brother.” Ray said once he had reached the same conclusion Grant had. Ray walked to the bathroom but he was shaking, already in fear of what was to come not just today but for the rest of the days.

As Ray took his shower, Grant got his sports bag and put Ray's clothes for the day in there. Grant smiled as he saw his naked brother come back from the bathroom. Grant had a thought he should make Ray go to school naked-that would be quite a sight-but he didn't want to push his luck. It was one thing for a kid to bike in only his underwear in public in the eyes of adults. Quite another for him to bike naked. One they could dismiss as children being children. The other they might feel compelled to get involved.

Ray put on a pair of tighty-whities. They went downstairs and Grant made the two of them breakfast. Once they were done and they got on bikes, Grant reached over and gave Ray a wedgie.

“You are going to go to school with a wedgie today. If you unpick it before I tell you to do so, we'll stop and I'll give you a spanking before I give you a new wedgie.” Grant told him.
“Yes brother.” Ray meekly said. He was already crying from the shame of being seen in only his underwear.
“You know wearing just underwear, with your underwear up like that, we can basically see your butt. Almost like your naked.” Grant taunted him. Ray just looked down.

They biked all the way to the elementary school. Once there, the kids were laughing at Ray again. Grant knew that Ray had been bullied this year not just by himself but by other kids in his class. Based on what Ray had told him on the ride home from yesterday, Grant was only making it far worse on Ray. He was encouraging the bullies to get more creative. It had become like a competition: who could be a worse bully than Grant? Yesterday Ray had biked home smelling like urine.

Grant helped Ray secure the bike. Then he had Ray put his hands on his head, like last time, only this time instead of having Ray just stand there facing the kids, he turned Ray around. People laughed at his butt. They mocked Ray cruelly, taunted him to further tears. Only then did Grant finally allow Ray to undo the wedgie and after Ray did that he allowed Ray to get dressed.

Grant then biked across the street to his school but he could hear the little kids still laughing at Ray. When Grant got to school, he rushed to his first period class. He was almost late.

Between third and fourth period, he and his two friends, Mark and Jay, learned from Hope that not only had Simon passed his anal test that day (why Jay wanted to know this was beyond him) but that Simon had been spanked that morning when his parents woke him up and he had morning wood. Grant ignored the small tent he saw in Jay's pants. Hope and Jay both wondered what Simon would be doing seeing as how he would be busy during lunch and after school. Grant and Mike didn't care. Hope also said she was no closer to finding out how Mr. X was but she was investigating a lead. Grant was surprised that he no longer cared to find out who Mr. X was. Then again, maybe it's because he loved to make his little brother miserable and Mr. X's ideas were excellent in making that happen.

When Marcus Oran got to the school that day, he was a little worried that people would ask him lots of questions. His official cover story was that he was filming a personal short film project with Simon as the star. To his surprise, nobody questioned him on it. He went to the classroom the principal had laid out. Like the principal promised, only he would be using it (along with Simon), the windows had curtains, and it would be private. The principal asked no questions, not daring to insult the man who donated so much money to the school every year.

When Simon Fulton arrived at the classroom, Marcus felt a small panic. It was one thing to use actual 16 and 17 year old teenage girls in his film. He was a straight man but the allure of a teenager was always strong. But this was not just a boy but one who clearly hadn't enter puberty yet! He wasn't a pedophile! He knew with his heart that what he was about to do was wrong....but he had to do it. In the eyes of the world, a pedophile was a pedophile regardless of whether he was going after 16-year old girls or 11-year old boys.

He closed the door behind Simon and locked the door.
“So Simon. I'm Marcus. I think you've seen me at your assemblies. I'm working on a special video project and I'd like you to be the star.” Marcus said.
As any kid would when they were told they'd be the lead in a short film, Simon smiled. The call of fame often ensnared so many innocents.
“Will you be my star?” Marcus asked without giving any details of what he'd had Simon do.
“Yes, I will!” Simon said in a very happy tone.

Marcus had already set up the camera and the lights. He just turned them on. He then looked at Simon.
“Okay so the story is simple. You are over there naked, masturbating. When you reach your orgasm, I as the principal am going to catch you. In order to avoid any real trouble, you are going to give me a handjob. Do you understand?” Marcus asked Simon.
Simon's mouth was open in shock. After a couple of seconds for Simon to process what Marcus had asked, Simon said “There's no way I'm doing that.”
Marcus shook his head. “You already agreed. You are doing it no matter what but if you want a spanking before you do it, I'm happy to oblige.”
Simon rubbed his butt and his face winced. Simon did not want a spanking, Marcus could tell that much.
“Fine.” Simon said.

Marcus was surprised. He thought for sure he'd have to grab Simon and spank him until he agreed. Once Simon was naked, Marcus saw why Simon had agreed. Simon's butt told him that he wasn't eager to get spanked any time soon.

Marcus had Simon stand in position so that all his cameras would catch it. He had different cameras: some to capture close-ups, some to capture Simon's whole body from different angles. He pressed a button that set all the cameras to record.

“Action!” Marcus yelled out.

Simon reached down and grabbed his soft penis and before Marcus knew it, it was hard. Simon kept going and going. Marcus himself didn't get hard but he did think Simon looked sort-of cute like a little kid does. Only a little kid that was doing a disgusting thing in front of him, under his command, and he was recording it.

Once Simon was done, he yelled out that he was cumming. Marcus hadn't told him to do that but since it was a dry cum, Marcus appreciated it. Then Marcus scolded himself silently for that. Still, as if on cue, Marcus stepped in front of the cameras.

Marcus and Simon followed a script. Marcus: What are you doing young man? Simon: Nothing! I promise! Marcus: I caught you red handed, I should spank your butt red! Simon: No, please, no! I'll do anything! I'll do what I did to you! Marcus pretended to think it over. Marcus: Okay but you better make it good.

Simon reached over and undid Marcus' pants button and zipper. He dragged his pants and underwear down to his knees. Simon then grabbed Marcus' very soft penis and started stroking it. Marcus pretended that Simon was a hot teenage girl. That got him hard.

Simon kept going, his face right in front of Marcus' penis thanks to the size difference, until cum exploded all over Simon's face. Some of it even got in Simon's mouth-which he swallowed to Marcus' surprise.

Now that they were both done, Marcus yelled out cut. He turned off the cameras and the lights as Simon got dressed. He told Simon that if he wanted the video to remain in Marcus' private collection and not released to the public, he better not tell anyone about it. Simon nodded.

Simon quickly got lunch and wolfed it down. He thought about his day so far. It had been pretty “bad” waking up to a spanking, getting fingered again, and then having to masturbate in front of a camera before having to give a handjob to an adult. He still had to look forward to once again appearing in only his underwear in front of his gym class where he will get a wedgie once again exposing his butt to every kid there. Then he'd have his very embarrassing “community service” event. Simon couldn't wait!

When he went to the locker room that day, he simply took off his pants and his shirt. He left his underwear, socks, and shoes on. He went to the door to leave and he hesitated for a second. As soon as he opened that door and stepped through it, he'd be once again in public in only his underwear. He took a deep breath, opened the door, and stepped out into the hallway. Laughter followed him all the way to the gym.

Simon quickly found himself surrounded by Jay, Mike, and Grant. His three new bullies who were now perfect in their task of making his life “miserable”. Simon did flinch. He knew what was coming. He wanted it as much as he hoped that for once, they wouldn't obey Mr. X.

Before he knew it, Grant had grabbed his underwear and pulled it up giving him a painful wedgie. “Hah! Look, we can see his butt like he's naked!” Grant commented. For some reason, Simon thought that comment wasn't one Grant made on the spot but one he had planned. Not that it mattered as people laughed at him.

There were basically two Simon Filchers: the one who was Mr. X. The one who enjoyed what was happening. The one who had an amazing orgasm earlier when Marcus shot his little movie for him. The one who kept going. Then there was the other Simon Filcher. This part was the public one. The one that found himself getting bullied by teachers, parents, and his fellow classmates for seemingly no reason. The one who didn't enjoy what was happening to him as well. And in that moment, Simon knew he wasn't Mr. X but Simon Filcher. Which meant even though he knew it would earn him a spanking on his sore butt, he had to unpick the wedgie the first time he got. After all, Simon wasn't supposed to know unless the three boys told him and they hadn't what would happen when he did.

As soon as Grant let go, Simon quickly unpicked the wedgie. “Hey! We didn't say you could undo Grant's work!” Mike said, grabbing the underwear and pulling it right back up. Meanwhile, Grant grabbed Simon's arms and holding them in front of him. Jay started to slap his butt, Simon started to cry after the fifth slap. All in all, Jay gave him ten with his hand. He threatened it would be worse every time he unpicked it.

They let him go. At this point, Coach Weatherby grabbed him and dragged him over to the bleachers. He sat down and put Simon over his knee. “This is what you get for getting an erection without permission!” He said. Yes, the wedgie had indeed given Simon an erection. With a wooden paddle, Coach Weatherby started to give a paddling to Simon. There was no protection from his underwear: it had been pulled up, leaving his cheeks perfectly exposed. In fact, during the paddling, Jay pulled on the underwear so not only was he feeling each slap, he also the pain from having something pulled into his ass. Simon's head was right in front of Jay's crotch during the whole time. He could see Jay's erection right in front of him.

After twenty hits with the paddle, Coach Weatherby let him go even though he still had an erection due to the wedgie. This time Simon didn't have to lead the stretches but the boys warned him to make sure his wedgie wasn't lost during them. This meant every now and then Simon had to pull on his own underwear, painfully pulling it up. Most of the girls were behind him during the stretching, making fun of his butt.

During gym class that day, they played dodgeball again. He got out four times during this session and each time one of the three bullies took the time to drive his underwear deeper into his ass. Simon was afraid they would rip it, leaving him naked in front of the whole gym class, but even though he heard a few tears, they didn't. At least he wasn't paddled again.

After gym class, he was escorted back to the locker room by Jay, Mike, and Charles. They made sure he didn't unpick his wedgie until he was back in the lockerroom and they let him take his underwear off to take his shower.

He got dressed again after the shower and went over to his advisor's office. His advisor was Martin Simmons. Martin was old. He often heard Martin complain about the school system and how they were getting cheated out of a good education due to weak standards, poor discipline, and parents who thought their children were perfect and couldn't possibly have gotten a bad grade. Martin was also Simon's English teacher.

Martin drove him across town. He didn't take him to one of George Crane's nice apartment buildings where some of Simon's classmates lived. Simon was sort-of relieved about that. He wasn't ready for a lot of his colleagues to see him naked. Not yet...Simon was instead taken to a poor part of town. The seedy part that his parents looked down on. A part where crime ran rampant, school buildingsr esembled prisons, and the school equipment looked more third world than first world.

During Simon's drive, Grant hanged out with Jay and Mike for about half an hour before he went by himself to pick up Ray from the elementary school. To his surprise he saw a large crowd of kids, mostly girls, surrounding the bike rack. He pushed his way through and in the middle and facing all the girls, he saw a completely naked Ray. He had his hands duct taped together behind his back, his face full of tears, and his backpack at his feet.

“Why are you naked?” Grant asked him, not letting him go and making sure not to block the view of a single kid by standing next to his brother.
“You know that game I told you about where the bullies tried to see who could top you off? Well this was one of their ideas. I've been here for the last half-hour waiting for you like this.” Ray said.
“I guess you are lucky I came here early today. Normally, you'd have waited an hour.” Grant observed.
“I know. Can you let me go?” Ray asked his brother, hoping for mercy.
“I don't know. Maybe I should make you walk home like this.” Grant said.
“Please don't make me do that! Please! This is bad enough!” Ray begged his brother.
Grant decided to show his brother mercy. “Fine. Where are your clothes?” He asked him.
“They are in my backpack.” Ray said.

Grant went through the clothes. He found Ray's pants, shirt, socks, and shoes. “Where is your underwear?” Grant asked Ray.
“One of the other bullies tore it up in a wedgie.” Ray admitted.
“Your such a loser.” Grant said, eliciting a new round of laughter from all the kids who heard him.

Grant took Ray's socks. He lifted Ray's left foot. Ray tried to insist he could dress himself but Grant told him to shut up, he was obviously a little kid. That got more laughter. And so Ray had the shame of being dressed like a little kid in public.

Once Grant put on Ray's socks, he put Ray's pants on his feet but he didn't pull them up. “Don't you dare pull them up until I say.” Grant whispered in Ray's ears. He took a pair of scissors and cut up the duck tape. He then ordered his brother to put his hands up. Grant put on Ray's shirt, which didn't cover his privates. Grant then had Ray put his hands behind his head, making sure his shirt didn't cover his genitals.

“Do you want me to pull your pants up?” Grant asked Ray.
“Yes brother!” Ray said.
“Really? You are so pathetic down there, I'm surprised you think you have anything to hide.” Grant said. New waves of laughter from the kids surrounding them and new tears from Ray's eyes.
“Please! Pull them up!” Ray begged.
“How badly do you want this?” Grant asked.
“As much as I've ever wanted anything in the world. I'll do anything.” Ray begged.
“Fine. I'll pull your pants up but you will owe me one. Okay?” Grant asked. Ray nodded.
Grant pulled Ray's pants up. They then went home. Once they were home, Grant had Ray strip naked. He then had Ray repay the favor by having Ray act as his naked slave for the rest of the afternoon. When Ray went to bed that night, he thought it was the worst day of his life by far. And he knew that the next day wouldn't even be better. He'd not only got to school in only his underwear again but Grant had teased him now that the girls have seen him naked for a long period of time, they've memorized every detail of his penis. When they saw his bulge, the girls would easily be able to picture him outside his underwear. Plus the competition to see who could bully him the worst would only heat up...

Simon was dropped off in front of a 3-story apartment building that looked shady. He wondered if any drug dealers or addicts lived there. The lawn was unkempt, graffiti covered the wall, and the windows on the first floor were barred. As Simon opened the door and stepped into the apartment building, he learned that one of the hinges was loose. Simon gulped. This was not an apartment building he wanted to be in nor did he have it in mind.

George Crane and one of his body guards met Simon in the lobby, if one could call it that. There was a pedestal where a statue had once been but there was nothing there now. The fresco on one of the walls that an artist had once painted was cracked and faded. The trees next to the front door had withered up and died from lack of attention.

There were three apartments surrounding the lobby. The doors were currently closed.

“Ah, Simon. Good to see you. When I said I wanted a kid from your school to help out the poor, the principal pointed me right to you.” George Crane began. Simon was a bit stunned by the man's outright lie but he managed not to show it. After all, he wasn't supposed to know the truth. “I need someone to go to every tenant and just you know help them out. Be a blessing to them.”

At this point, George looked over Simon. Simon was wearing his school uniform. Simon went to a pretty nice school: his uniform betrayed the kid as a son of privilege.

“That uniform is going to be a problem. If they see you in it, they might beat you up or worse.” George Crane said. “I think you should strip. Now sadly I won't have anything for you to wear but you definitely can't wear that.”
Simon looked at him. He opened his mouth to pretend to be in shock. He had quickly learned that was a good way to throw the scent of him. Pretend to be surprised and nobody would suspect he was secretly the mastermind.
“Now of course you could refuse to do what I say. But then I'll kick you off my private property and you'll have to walk home all by yourself. In this neighborhood, how long do you think you'll last?” George said. It was a good tactic. Even if Simon wasn't Mr. X, he had heard enough horror stories to believe they were all true and they would all happen to him.
Simon nodded to tell George he understood. He took off his shirt. Once it was on the floor, the body guard scooped it up. Simon wondered what the body guard had been told. He must have been very loyal or paid very well to go along with this. Simon kicked off his shoes and the body guard picked them up as well.
“The socks as well. They are way too nice.” George Crane quickly added. Simon took them off, throwing them towards the body guard. He grabbed them. Simon put his hands on his pants and pretended to hesitated for a couple seconds. He then pulled them down, leaving him in only his underwear. He handed his pants to the body guard.
“Good.” George said. “Good. Now I am going to say you need to take your underwear off as well. Even that underwear with it's brand name is too good.”
“No way.” Simon said, his protest as pretend as it was a real gut reaction.
“Well suit yourself, Simon. Of course, you'll be out in the streets wearing underwear that some gangster is going to take. Then you'll be stuck out there naked as you walk home. Assuming nothing else happens to you.” George said, making sure Simon realized he had no real choice.
Simon took off his underwear and handed it to the bodyguard. He then used his hands to cover up his penis and balls.
“Good. Now remember, if you don't want to do anything, you can leave naked. But if you want to go home with your mom, you will do as instructed. Do you agree?” George asked. Simon nodded as his cheeks went red.
“Stop covering yourself up. I don't want anyone to think you are playing with yourself.” George commanded. Simon obeyed, putting his hands on his side. “Well that's pretty small. Not very impressive.” George commented and the body guard gruffed as if to agree.
“So here is what I want you to do. Go to every apartment and offer to help. They'll know you are coming so they should each have something for you to do. I understand one of them on the third floor is having a birthday party for a girl your age so maybe you'll have some fun as well. Or not due to your state. You are never to cover your privates from anyone Tell them you are a nudist and since I've given you permission to be naked on my private property, you aren't breaking any laws. You will then tell them that you will do anything they ask within your ability and that if you don't perform up to expectation or for any other reason, they may punish you as they see fit. After you are done with the task, you will then ask them if you've performed satisfactory. If you have, you may move on to the next apartment. If not, go back until you've done so and then ask for a punishment before you move on. Did you get all that?”
Simon nodded. “Yes sir.”
“Good.” George said. “The door behind me is the leasing office. I'll be in there for when you are done. My man here will make sure you go to every apartment.”
George walked into the leasing office.

The body guard walked up to Simon. “There are four apartments on every floor. We should get started” The body guard told Simon.

Simon went to the first apartment: #11. He looked down at his naked state. Even though he was on private property, he realized he was actually naked for anyone to see. He wasn't wearing a single thing, not even a necklace.

Taking a second, Simon knocked on the door. Within a couple minutes, a chubby hair man wearing only an undershirt and tighty-whities opened the door. The man looked down at the naked kid in bemusement.

“Hi. I'm Simon Fulton. I'm a nudist on private property so this is legal. I'm here to help you with any task you need within my ability and if I don't perform to your satisfaction or for any other reason, you can punish me any way you want.” Simon said.
The man grunted before speaking. “I'm Phil. Come in.”
Simon went in. He noticed the body guard stayed right outside the door. The man closed the door. He looked at the naked kid in front of him. He noticed his butt was sort-of red. Clearly it had been spanked. Simon looked at the man's underwear. He could tell the man had an erection. He briefly wondered if he would be forced to lose his virginity to the man. He hoped not.

The man guided him to the kitchen. “I need to clear out my fridge and make sure it's super clean.” He said as he got some trash bags. He handed it to Simon. “That's what I need you to do.”

The man then went to the living room. Simon opened the fridge door and he almost threw up. The man wasn't just a snob in the fridge. It smelled and looked disgusting. There were liquid stains everywhere, rotten food that's been there for months if not years, and in the very back he thought he saw something that looked like it had little rat feet.

Simon got to work. It wasn't a pleasant task. He had to pick up really disgusting pieces of food with his bare hands. He didn't have gloves, no matter how much he wanted them. He filled up three of the trash bags before the fridge was completely cleared out except for one item. To Simon's astonishment and alarm, there had indeed been a dead rat at the back of the fridge. How it got there was something Simon didn't know and he was confident he didn't want to know. He used one of the trashbags to pick it up and throw it into another trashbag. He closed them down tight.

Simon took out the fridge trays. Somehow Phil lived without any napkins, paper towels, or rags to clean up the stains. Not really have a choice, Simon used his own hands to clean up the stains. He turned on the sink. It took a lot of rubbing away with his fingernails but he eventually had them all spotless. He put the trays back in and then washed his hands.

He took the trashbags. He noticed in the living room that Phil was sitting on a couch, watching TV, now completely naked. He couldn't tell what disgusted him more: the man boobs, the ridiculous amount of body hair, or the man's erect penis as he mindlessly stroke it.

Simon opened the door. The body guard helped him carry some of the trash bags to the compactor before the two walked back into the apartment. Once again, Simon was the only one who went in. “Your fridge has been cleaned. If you believe I haven't done a good job, please punish me.” Simon said.

Phil stood up, went to the kitchen, and came back. The man sat back down on the couch, looking not at the TV but at Simon's penis as he started to stroke his own penis again. “You did a good job Simon. I hope you come back next week.”

Simon didn't take his time getting out of that apartment. Once he was outside and the door was closed, his body took a tiny shake as if it was glad to really be out of there. “There was a dead rat in his fridge! A dead rat!” Simon told the body guard, who merely shrugged.

The two went to the second apartment door: #12. Simon knocked on the door again. Only this time, it was an old feeble lady with white hair who opened it. She opened her mouth in surprise. She yelled out “Pervert!” was about to shut the door on the kid but the body guard's hand propped it open.

“Hi. I'm Simon Fulton. I'm a nudist on private property so this is legal. I'm here to help you with any task you need within my ability and if I don't perform to your satisfaction or for any other reason, you can punish me any way you want.” Simon said.

The old lady seemed to calm down. “Oh, I've been expecting you. Why don't you come in?” She said. Simon went in. Like last time, the bodyguard stayed outside the door.

Unlike Phil's apartment, hers was completely clean. “My kids and my grandkids never come to visit me. Which is too bad but you do remind me of one of them. He too would like to go around naked. Anyways, all I need you to do is help me set up my internet.” Simon noted she purposefully avoided looking at his penis.

Once Simon finished this rather easy task, she proclaimed she did a good job and let him go. Simon went to Apartment #13. There he found a man and a woman, decently dressed, waiting for him. They had him vacuum the floors and clean the apartment's light mess. Once again, they were satisfied with his work.

At Apartment #14, a woman opened the door. After his introduction, she invited Simon into his home. He quickly learned she was a single mother of six kids: a sixteen year old boy who was currently in prison, a fourteen year old girl who claimed she was in the library studying but her mom suspected she was really with her boyfriend having unprotected sex, a twelve-year old girl that giggled and stared at Simon the whole time he was in the apartment, a nine-year old boy who was serving a corner time punishment, a six-year old girl who likewise giggled and stared at Simon the whole time, and a three-year old boy. The mom claimed she was very busy that day but all she needed was for Simon to wash her youngest son since it gave her more time to do adult work. She was satisfied with the job.

When Simon left that apartment, he was happy to be gone from the eyes of the girl a year older than him and a couple years younger than him.

They went to the second floor. At Apartment #21, a man and his wife opened the door. Their task was to help their ten-year old daughter with math homework. Simon did the best he could but he did make some mistakes since he got distracted because she kept glancing at his penis. The man and wife punished Simon by having their young daughter spank him with a belt for every mistake he made. All in all, Simon had twelve slaps. With his already sore butt, he was crying from the sixth one on.

Over at Apartment #22, a single dad opened the door. He had one son, a rambunctious five-year old. His task of cleaning up the kid's room was complicated by the kid continually making a new mess while throwing stuff at Simon's balls (although he didn't hit once). Once Simon was finally done, the dad was satisfied with the work but he wasn't happy to see Simon hold his kid during the inspection. The man said his son deserved to be free at all times. Simon's punishment was to stand still, hands over head, as the kid punched him in the balls twice with each fist.

At Apartment #23, a young professional woman had him take out her laundry from the basket and put it in her closet. Then at Apartment #24, he helped an older lawyer make copies. He managed to do both without getting punished. He was happy they didn't have any kids.

There were then four apartments left. Apartment #31 had him do a quick run to the lobby then back to pick up their mail. Apartment #32 had him lead a snickering old woman in exercise. In Apartment #33 he had to help move a couch. All good jobs. No kids in any of them.

Finally, Apartment #34. George Crane was right. There was a small birthday party going on: the mom, the dad, the eleven-year old girl, and six of her female friends were there. Simon was the only boy there. His task was to entertain them which he found to be difficult and it kept his cheeks red since it meant having to stand naked in front of the girls. He didn't really know what to do. He tried three things: stand-up comedy, magic, and being a clown. It turned out he wasn't funny (although the girls couldn't stop laughing at his naked state) and he sucked at doing tricks. Every time he failed, the mom and the dad gave him a spanking with their hands.

Finally, they just gave up and put on a movie. But since he hadn't really done his task, they did let the birthday girl spank him. It wasn't a very hard one but it was an embarrassing one-plus she did take the opportunity to feel his penis and balls.

Once that was done, Simon went downstairs and the bodyguard confirmed to George Crane had done gone to every apartment. The bodyguard did tell that Simon didn't really do a good job with one of the tasks and didn't really complete his last one but the tenants had let him go after four punishments. Crane nodded.

That gave George Crane the excuse he needed for the next part. “Okay. I'm going to call your mother and tell her to come pick you up. It should take her about an hour. During that time, as punishment for failing in some of your tasks, you will stand outside on top of the pedestal, with your hands on your head, and an erect penis. You are not to lose that erection or move. Unless you want to go home naked. Got it?”
Simon nodded.

And so Simon stood there naked. He managed to keep his erection by thinking about all of the girls that had looked at him and mocked him. He managed not to move even as people went by the lobby. Almost all of them asked the bodyguard what was going on. He told them Simon was a nudist and an artist, doing an art display. Since this was private property, George had given Simon permission to legally pretend to be a naked statue.

Most moved on. A few did try to make Simon to move by touching him-even in inappropriate places but they didn't linger there in case the bodyguard noticed-and one of them even slapped his butt. The girls who passed by (most of them leaving or joining the party) mocked him. The boys who passed by (probably visiting friends) couldn't believe what they saw but they also made fun of him.

When his mom arrived, George left the leasing office and handed Simon his tighty-whities. He explained his mom had insisted that be all he wear. George wasn't actually lying: his mom after all was also following Mr. X's instructions.

Once Simon got home, he got spanked by both his parents for not 100% properly doing his community service. They also spanked him later when he got hard in front of them while they were rubbing an ointment on his butt to ensure the spankings he was getting didn't leave any lasting harm.

The good news is that Simon did get to send an e-mail to Samantha Korn that day. Ted had sent him video evidence of his math teacher accepting a bribe from a parent to give the student a better grade. Illegal and would destroy her career. He gave her a test to have Simon strip to his underwear the next day and then to paddle him. Simon smiled.

These were the best, and worst, days of his life.

(End of File)