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Pleasure and Plain Part 1 (improved format)

2023-01-11 01:55:44

I was looking forward to another relaxing weekend. School had been particularly rough this week and I could use the rest. It turned out that seventh grade was considerably harder than I thought it would be. But I was 13 now, and I could handle it. Just the same, the weekend was a welcome respite.

I was just settling into the couch to play a few hours of Madden, when the front door burst open and my father barged in.

When I saw the look on his face, I become a little frightened. “What’s wrong Dad? Why are you home so early?”

“Grandma Kathy fell down the stairs in her house and she’s in critical condition in the hospital. I have to pick up your mother’s and my passport and then we’re off to the airport. We’ll give you guys a call once we’re on the ground in Vancouver.”

He disappeared upstairs before I had a chance to say anything.

I sat there thinking about what he had said for a minute. Grandma Kathy was his mother, and while I felt bad for what had happened, I didn’t actually know her too well. We had lived in Pittsburg my whole life and she had lived in Vancouver that whole time. I had only seen her a few times in my life.

I was still pondering this when my father came back down the stairs.

“Your sister will be in charge until we get back. Do whatever she tells you to and don’t give her any trouble okay, Jason?” He paused with his hand on the front door handle and gave me a serious look. “I mean it, alright? I’m under enough stress already and I don’t want to have to worry about whether or not you’re getting into trouble. I‘m going to call her on the way to the airport and tell her as much.”

“Okay, Dad. I got it.”

“Good.” He paused for a moment, looking as if he had more to say, but then opened the door, said “see you later,” and left. A minute later, I heard the car pulling out of the driveway, and then he was gone.

So, the good news was that my parents were gone for a few days, giving me the kind of freedom I had always dreamed of. The bad news was that Grandma Kathy had to go and hurt herself for it to happen. And of course the really bad news was that my sister Jennifer was in charge.

Jennifer is an okay person as far as things go, but she’s still my sister, and I guess there’s some kind of rule that says that I have to have feelings of animosity towards her. It could have been worse I suppose. At 15, she had the same blonde hair and blue eyes as me, except where my hair was curly, hers was long and wavy. She also had a decent sized pair of melons; 34C is what the bras that I had jacked off into had said. Her hips were mesmerizing, her smile devastating, and even though she was just a freshman at the regional high school, her legs were already legends there. And because she was so hot, it only made sense that all her friends were hot too.

Especially the two girls she hung out with the most. There was Jessica, long brunette hair, brown eyes, and even bigger tits that Jennifer, my guess being a D cup. The third girl, who in my opinion was the hottest of the three, was Jillian. She had long red hair, dazzling green eyes and the cutest dimples when she smiled. Like the other two girls, Jillian had also been blessed with an ample chest. She fell somewhere between Jennifer and Jessica in terms of size.

All three girls were inseparable, all three girls were exactly 5’3” and of course all their names started with J. Because of this they were known as the J triplets. It was like every man’s fantasy in triplicate. And they were at my house several times a week. I couldn’t really complain.

By this time, Madden had finished loading and I got lost in the game for the next several hours. I was just getting up to take a leak and grab a soda when the front door opened and my sister walked in.

“Hey squirt,” she said, using her oh-so affectionate nickname for me, a bit ironic at this point since I was two inches taller and twenty pounds heavier than her.

“Dad called me and told me what happened to Grandma Kathy. Kind of sucks, doesn’t it? But he also told me I was in charge until he and mom got back. He said, and I quote, ‘Justin has to do everything you say until we get back.’” An evil grin formed on her face. “Maybe this will end up being a good thing.”

A shiver ran down my spine. This was a side of Jennifer that I hadn’t seen before. I began to wonder if I should be worried.


Once I finished playing my game I made myself some pasta for dinner (yes I know how to cook) and then got started on my weekend homework assignments. By the time I got into bed, I hadn’t even seen my sister again, let alone fallen victim to some evil scheme that she might have been plotting. By the time I fell asleep I had mostly forgotten about that smile. Saturday would bring a cruel reminder.


Saturday morning I woke up at ten o’clock. When I came downstairs for breakfast, Jennifer was already there, along with Jessica and Jillian.

“Morning, Justin,” Jennifer said.

“Hi there,” Jillian said sweetly. I’m pretty sure she had a crush on me. Jessica just smiled at me.

“Hi guys,” I mumbled as I made my way over to the fridge.
“The three of us are going shopping,” Jennifer said, “but we shouldn’t be gone for more than a few hours. Can you behave while we’re gone?”

I suddenly perked up. This was going to be great! “Yeah, no problem,” I said as I poured myself some milk.

“Good,” Jennifer said. “Oh and by the way, Mom and Dad called a little while ago. They got to Vancouver fine, but Grandma Kathy’s condition is still up in the air. They think they’re going to be there for several more days, and perhaps even longer if things take a turn for the worse. They said they’d call again before we go to bed tonight to check in.”

“Okay,” I said through a mouthful of cereal.

Just then there was a honk from outside.

“There’s Timmy,” Jessica said as the girls stood up. Timmy was Jessica’s older boyfriend. Since he was sixteen, he was able to drive, and he would give Jessica and her friends rides from time to time. I’m guessing she gave him blowjobs or something in return, otherwise why else would he be wasting his time playing chauffer?

“See you later squirt,” Jennifer said as the three girls raced out the door leaving me to my breakfast.


After I had finished my breakfast and brushed my teeth, I called up my best friend Derrick and he came over to play Madden with me. What!? I had only got the game last week and I was still in the I-can’t-get-enough-of-it phase.

He was only able to stay for a little while though because he had to be at some lunch time barbeque with his neighbors. Before I knew it he was heading home (but not before I beat his ass at three full games). He had been gone no more than a minute when the door opened up again and the three girls piled into the living room. I was totally expecting to see each of them laden down with bags, but in fact they only had one amongst the three of them. The bag definitely caught my attention however.

It was from the store Leather and Chains. An adult store in downtown Pittsburg. I don’t know how at their age they were allowed in the store, let alone allowed to buy something, but I was suddenly desperate to see what was in the bag.

The girls noticed me looking and they all smiled at me. “We bought a game,” Jillian said. “Do you want to play with us?”

I didn’t even know what the game was yet, but there was only one answer that any warm-blooded straight male could give when presented with such a question: “hell, yeah!”

“We were hoping you would say that,” Jennifer said. “Come on. Let’s take it to the living room.”


When we had all sat down in the living room, me in an arm chair and the three girls on the couch, Jennifer pulled the game out of the bag. It was a black box with three words splashed across the front.

Pleasure and Pain.

I suddenly wondered what I might be getting myself into.

“The clerk in the store said it was like Truth or Dare, except without the truth part,” Jessica said as Jennifer started to unwrap the plastic that sealed the box. “Only with a game board, cards and dice and stuff. She said that instead of asking truth or dare, on your turn you pick an action card that tells you what to do. The dice indicates the intensity level of what the cards say. I’m not quite sure what that means, but I guess we’ll find out. And as the name of the game says, some cards will bring pleasure, and some will bring pain. If you successfully complete your task, you get to move your piece forward. Whoever gets to the end first wins.”

It sounded terrific! I couldn’t wait to begin. I bet I would get to do all sorts of sex things with the girls. Maybe even go all the way. And if there was a little pain, how bad could it be? It was just a game, right?

“What’s wrong Jennifer?” Jillian said suddenly. I looked at my sister, who was reading a large blue sheet of paper with a concerned look on her face.

“According to this,” she said slowly as she continued to read the sheet, “this is a special limited edition extreme edition of the game. Apparently, of all the games they produced, they made ten of then with extreme editions. There is no indication of it on the outside of the box. Apparently it’s like some sort of contest.”
“What does that mean?” Jessica asked.

“Well let me read you what it says,” Jennifer began. “Congratulations! You have purchased one of ten unmarked boxes of Pleasure and Pain: Extreme Edition. It is similar to the regular edition except more extreme. The way it works is simple. Instead of using the board and cards included in the box (which are for the regular edition), you must log onto the website provided to play the extreme edition. There you will find that the pleasure cards stay the same, but the pain cards take it to a whole new level! But hold on! It gets even better! If all of your players succesfully finish the game, your team will be entered into a raffle against the other nine Extreme Edition teams to win $100,000!”

“A hundred thousand dollars!? Jessica and Jillian squealed simultaneously.

Jennifer continued reading in a very excited voice. “This is a one time offer. Once you log in, you must play the game to completion in order to be eligible for the prize. If you log out at any time before you finish the game, you will be disqualified. For further rules and instructions, please log in with the following user name and password.”

Jennifer looked at the girls and me. “What do you guys think? Should we do it?”

“Are you crazy,” Jillian nearly shouted. “We’re talking about a hundred thousand dollars here. Of course we’ll do it!”

“Yeah!” Jessica and I enthusiastically agreed.

“Alright then, let’s go use the computer in the den.”

The three girls got off the couch and headed for the den. I stayed back for a minute and opened the package of cards marked Action. I wanted to see what we would be getting ourselves into.

When I turned over the top card it said pleasure. On the left side of the card it was numbered one through six, presumably matched up with the die roll. Next to one it said ‘one player will gently rub one of your nipples with the feather duster for thirty seconds.’ I looked in the box and there was a small feather duster provided. Next to two it said the same thing except using their fingers. Three was for one player on each nipple with fingers. Four was the same as three except for a full minute. Five was both with tongues for thirty seconds. And six was both players with tongues for a full minute. Seemed good so far. I turned over the next dare card and this one said Pain. This one required one of the players to smack your bare back with a towel five times. Two required the same thing but 7 times. Three was 8 times, four was only five times, but the towel had to be wet, five was six times wet, and six was 7 times wet.

This didn’t seem so bad at all. For sure I’d at least get a blowjob out of this game.

“Are you coming Justin?” my sister called from the den.

“Yeah, I’m coming,” I yelled back as I made my way to the den. We hadn’t even started playing yet and my pulse was already racing.


When I got to the den they already had the computer booted up and were in the process of typing the web address into the URL bar.

We happened to have a really nice computer. My father was a bit of a tech freak and he liked to splurge on things like this. The computer was brand new and had amazing specs, although I honestly didn’t know too much about that. What I did know was that it had a kick-ass 24 inch monitor that delivered the most awesome picture quality I had ever seen. There was also a built in high definition webcam.

“Okay, here we go,” Jennifer said as the site loaded up. “Let me just put in the user name and password.”

A moment later the screen changed and a warning message popped up.

Jennifer read it aloud. “Warning: before continuing, realize that there is no backing out. Please click the next button to read the additional rules of Pleasure and Pain: Extreme Edition before continuing.”

Jennifer clicked the next button and then continued reading. “For every Action card you complete your game piece will be advanced one square. You will not be eligible for the prize money unless all players advance their game piece to the tenth and final square. Please note that the raffle drawing will not take place until all ten teams have played the game or until the deadline of September 5th 2012.

Please also note that to ensure compliance of the players (in other words, to discourage cheating) you must have all activity take place in front of a webcam that we will use to record the game. This will later be reviewed by our staff to ensure compliance. If any cheating is discovered, you are automatically disqualified. If you agree to these terms and have the webcam ready, please click ‘I accept these terms.’ Otherwise close this website and come back when you are ready. Please remember that once you click accept there is no turning back.”

Jennifer finished reading and looked at the rest of us. “Well, are we ready guys?”

“Click the fucking button already!” Jessica said.

“Alright then, here goes.” And with that said, she clicked the button.


Sharon Moss was in the midst of a ferocious battle against a level 20 troll king when her phone indicated a text had come in. It only distracted her for a split second, but it was a crucial second. She looked back in time to see her character being knocked off the side of a cliff, where it promptly fell to its doom.

“Shit! She screamed, pounding her fist on her computer desk. This had the unwanted effect of knocking her half finished can of cola over and onto her shirt.

“Fuck!” She screamed as she tried to wipe the cola off of her. After a second she realized the futility of what she was doing and simply took the shirt off. As she was not wearing a bra, this had the effect of releasing her enormous 34 E breasts into the cool air of her bedroom. Her nipples hardened instantly.

Sharon was only 26, but she was already an ice cold feminist bitch. She had developed at a young age, already wearing a D cup bra at the age of 12. As such, for more than half of her life she had been subject to the lusty stares of men, including her own father. She had come to realize very quickly that all men were pigs who only thought with their dicks. As such, she had never had a boyfriend and never planned on having one. She wasn’t in the slightest bit lesbian; she simply refused to let a man near her. The very thought made her ill.

After cleaning up the desk with her already wet shirt, she was finally able to take a look at her phone.

When she saw who it was from her eyes lit up with glee. Someone had just logged into the Pleasure and Pain: Extreme Edition website. The Troll King was quickly forgotten as she logged into the website with her administrator access.

Truth be told, the Extreme Edition version of the game was entirely Sharon’s brain child and it was also highly illegal. The owners of the company she worked for knew nothing about it.

As far as the company knew, every box of Pleasure and Pain manufactured was exactly the same. But Sharon had managed to slip special instruction sheets into 10 boxes. These instructions directed people to the phony website she had created. Once they logged in and set up their webcams, the site would record all of their actions, ostensibly so that the judges could review their games and make sure they hadn’t cheated. In reality, there was no contest and their was no prize money. The entire thing was simply a way for Sharon to get rich. Once she had the videos, she was planning on selling them in the underground porn market for boatloads of cash. It was all very exciting.

Although she had to admit to herself that in addition to all her excitement, she was also a bit nervous. She had put many, many hours into developing this scheme of hers, and this was the first time someone had logged into the website. She hoped everything went according to plan.

Once she logged in, she waited for a moment while the signal from the webcam loaded. A moment later, her screen filled with the image of four people. What she saw shocked her. These were clearly children. The girls looked to be around 15, and the boy couldn’t have been more than 12 or 13. But her shock quickly changed to nonchalance. It didn’t matter to her. And in fact in all likelihood, she’d be able to sell this particular video for even more money. After all, the more illegal it was, the more it was worth.

She watched as the players entered their names and genders into the system and picked their pieces. Jennifer, Jillian, Jessica and Justin. And Justin had picked the red piece. That was the information she had been waiting for.

Opening up another window, she quickly accessed the code for the game. A few keystrokes and she was done. Now, poor old Justin would find that he was getting pain cards twice as much as the other players. Not only that, but the actions on the cards he received would be more gruesome. And finally, there was a surprise waiting for him at the end of the game that she had taken special pride in coding. For Sharon wasn’t just a feminist; she was a sadistic feminist and she liked to make men suffer.

Closing the window, she quickly got her 8 inch vibrator from her night table and placed it within easy reach on her desk. Then she settled back to watch the show.


“Okay, so it looks like Justin is going first,” Jennifer had said once they had each rolled the die.

“I think each person should get to click their own action card and roll their own die rolls,” Jessica said.

“Okay, that’s fair,” Jennifer agreed. “Come on over squirt, pick your card.”

Filled with nervous anticipation, I reached for the mouse and hovered it over the action card. Then with a loud gulp, I clicked the card.

The card flipped over, but unlike the cards I had seen, this one didn’t list actions. It simply said Pain, and the rest of the card was blank.

“Tough break Justin,” Jillian said gleefully.

“It doesn’t say anything on it,” I protested. “What am I supposed to do?”

“Roll the die you idiot,” Jennifer said as she indicated the die icon, which was dancing around like it had to pee.

I clicked on the die icon and it landed on 4. All of a sudden, words started appearing on the card. I began to read out loud. “For this action, you must remove all of your clothes. You must then leave them off for the rest of the game.”

“What!?” I protested.

“It’s a sex game, what did you expect?” Jessica retorted.

More words had appeared in the meantime, so I read those. “The smallest player in the game must give you three kicks to the nuts. Remember, inability to perform an action automatically disqualifies you from the prize money.”

I stared mouth agape at the screen. “I’m not letting any of you kick me in the nuts!”

“Oh, come on Justin,” Jennifer said. You’ve been hit there before when you play ball with your friends.”

“Yeah but never intentionally,” I protested.

“Well you’re going to let us do it or we’re not going to win that prize money,” Jessica said.

“Yeah, don’t blow it for us on the first turn of the game,” Jillian agreed. “Remember, they’re watching us.”

I had actually forgotten about that part. The hairs on the back of my neck began to stand up as I glanced at the webcam and wondered how many people were watching me right now.

“Fine,” I said. To be honest, the idea of a hundred thousand dollars was just as appealing to me as it was to the rest of them.

“Good,” Jillian said. “So take your clothes off.”

I blushed a little. The only one of these girls who had ever seen me naked was my sister, and it had been over five years since the last time. I had developed quite a bit since then and I was now sporting a seven inch penis and a large set of balls. It didn’t help my nervousness any that my cock was starting to become erect.

The girls’ eyes were riveted to me as I began to undress. I started with my shirt. They had seen me topless numerous times, so this part was a piece of cake.

As I took my clothes off Jillian piped up.

“It said the smallest one of us had to kick him but we’re all five foot three. What do we do?”

“Well, it said that he has to take three kicks, and there are three of us, so why doesn’t each one of us kick him once?”

“Yeah!” Jessica exclaimed, excited at the thought of being able to rack her best friend’s little brother.

I gulped nervously again as I listened to this exchange and started to take my pants down. Suddenly the girls’ eyes were locked onto me again as my pants fell to the floor exposing my tighty whities.

“Look how cute Justin is in his little underpants,” Jessica said mockingly.

“Hey, he’s got an erection,” Jennifer said laughing.

“Does he ever,” Jillian said as she eyed my meat lustily.

Getting up my nerve, I took a deep breath and dropped my briefs.

There was dead silence in the room as the three girls took in my impressive package. They must have stared for thirty seconds, before anyone spoke. All the while I felt like I wanted to sink through the floor.

“Alright, who kicks him first?” Jessica asked.

I looked at her in fear. I had been so nervous about exposing myself in front of these girls, I had completely forgotten about the kicks.

“Hold on a second,” Jillian said. “I want to check out his ass first. Justin turn around for us.”

I readily complied. Anything to delay what I knew was coming.

“Nice butt,” Jillian whistled as I turned for her.

“I’m sure you’ll get some time to play with it in a little while,” Jennifer said, causing Jillian to blush.

“Okay,” time for the kicking,” Jessica said eagerly. “Who goes first?”

“Well he’s your brother Jennifer,” Jillian said. “You should have the honor.”

“Yeah,” I guess so,” Jennifer said. She went to stand opposite me. “Get ready squirt.”

I looked at her long powerful legs, prominently displayed in a short white skirt, and then at her delicate feet encased in a simple pair of flats.

“Spread your legs,” Jennifer said. “Don’t make this hard for me.”

“I think he is hard for you,” Jessica joked, referring to my raging erection.

I spread my legs and clenched my fists as I mentally prepared myself for the first kick. If you had told me a few hours ago that I would be letting my sister and her friends kick me in the balls today, I would have called you crazy. But now here I was, naked as the day I was born and about to get my manhood smashed in by three sexy teenage girls. And this was only the first turn of the game.

Jennifer looked me right in the eye and grinned the same evil grin that she had given me yesterday. “Ready or not, here it comes!”


Sharon couldn’t believe her ears. The blonde girl was the boy’s sister! This kept getting better. As she watched Jennifer get into position she quickly shucked her shorts and panties and grabbed for her vibrator. The show was about to begin.