Pleasure and Pain (my first story)

[korvas]

Hi everyone. I have enjoyed reading stories on this site for a few years now, but until today I had never posted. In addition, I've been writing for most of my life, but I've never written an erotic story before. I hope you all enjoy it. (keep in mind that this first installment is not the entire story.)

Pleasure and Pain

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.

[mickeybb]

Great set-up. I hope you're going to make this game last longer than one turn. More, more, more, please!

[leofalchi]

Excellent beginning ! I hope to see the next part soon ^^

[kickpom]

It's good to see you trying your hand and writing, however sibling busting doesn't do it for me at all. I'm sure there's plenty here who like the idea of Incestual fantasies but that is not for me. I'll keep an eye out for your future stories.

[korvas]

I looked on in terror as my sister’s foot came barreling towards my exposed nuts. I instinctively closed my eyes and braced for the explosion of pain that I knew was about to come. But after a moment, when nothing had happened, I opened my eyes and looked down. Jennifer’s foot was centimeters from my balls.

“Wha-what happened?” I asked dumbfounded.

“Oh, I just wanted to make sure I had good aim first silly,” Jennifer said. Then without letting another second pass, she pulled her foot way back before rocketing it into my nuts.

The impact was like a freight train. My body visibly rocked as her foot exploded dead on into my nuts. The pain was instantaneous and intense, and before I knew it, I was huddled on the floor clutching my nuts and gasping in pain. Fortunately, it only took a few seconds for the pain to diminish from a level I would call mind melting to something more bearable. At this point I looked up to see the three girls giggling hysterically, and Jillian and Jessica high fiving my sister.

“That was awesome,” Jennifer said when she got her laughing under control. “It felt so exhilarating. I want to do it again.”

“Well too bad,” Jessica replied. “You had your turn. Now it’s mine.”

“Yeah, okay,” Jennifer agreed.

“Come on Justin,” Jessica said as she clapped her hands together. “Stand up. Let’s get this show on the road.”

“I think I need some help,” I responded weakly.

Jennifer and Jillian came over to me and grabbing me by the upper arms, lifted me to my feet, where after a moment I was able to stand unassisted.

Knowing I had no choice, I assumed the position and waited for Jessica to further my destruction. Fortunately for me, she was also wearing simple flats, so at least I wouldn’t be getting kicked by anything too devastating. I briefly looked over to Jillian. She was wearing a pair of hard pointed shoes. I wasn’t looking forward to that.

Jennifer took her foot and slowly extended it until it was right under my balls. She did this a few times to get proper aim, and actually lifted my balls in their sac a few times with her toes. I felt like I was going to pass out from anticipation.

“Okay, here goes,” she said as her foot raced towards my nuts. The second impact was equally as devastating as the first and I fell to the floor in a ball of pain. It was a good 15 seconds before I was even able to open my eyes this time. When I looked up, I saw that both Jillian and Jessica were openly rubbing their crotches through their skirts. When they saw me looking, they quickly stopped.

I couldn’t believe they were getting off on my pain!

“Alright, tough guy,” Jillian said. “My turn.”

Jennifer and Jessica helped me to my feet as Jillian started stretching, as if she were warming up for a soccer game. Which didn’t seem so strange really as Jillian played in the high school girls’ soccer league. I almost collapsed again at the thought, but Jennifer and Jessica were still supporting me and didn’t let me fall.

I figured that like the last two girls, Jillian would need to take a few practice swings first. I was wrong.

Whoosh, BLAM! The hard pointed toe of her shoe impacted directly into my right nut, causing a blinding jolt of pain to race through my body. I let out a pitiful mewling sound as I collapsed to the ground like a sack of potatoes. Based on the pain currently coursing through me, I figured I’d probably be laying there for the rest of my life.

“That was amazing Jillian,” Jennifer gushed. “You really destroyed him with that one.”

“I know, right?” Jillian agreed. “That was sooo great!”

“Okay,” Jennifer said as she walked over to the computer. “Justin finished his turn, so let me click this button and…” as she clicked the button, Justin’s piece advanced to the second square on the board.

“I guess Justin’s winning, huh?” Jessica said.

Jillian looked over to where I was still laying in a heap on the floor. “Oh, I don’t know about that,” she snickered.

“It’s your turn Jillian,” Jennifer said as she made room by the computer for her friend.

“Okay,” Jillian said as she took the mouse, and without hesitation clicked on the action card. The card flipped over and displayed the word Pleasure. “Goody,” Jillian exclaimed.
She then rolled the dice, and it came up six.

“Oh, wow. Lucky,” Jessica said.

Jillian began to read. “Get a player of the opposite gender to pleasure your pussy with his mouth for one minute. This will necessitate you taking off all clothing worn below the waist. You may not put them back on for the duration of the game.”

“You really hit the Jackpot,” Jennifer said.

“I’ll say,” Jillian agreed as she quickly took off her shoes, socks, skirt and panties.

She walked over to where I was laying with my eyes closed, mostly oblivious to the rest of the world. She gave my shoulder a gentle nudge with her foot and said “hey there pretty boy, I need your help for my first action.”

I groaned as I opened my eyes, but when I saw what was in front of me, my pain was immediately and fully forgotten.

Standing above me, her feet straddling my head, was Jillian, completely naked from the waist down. Her beautiful vagina, the first I had ever seen in real life, was completely bare except for a small landing strip made up of her downy red hairs.

She started lowering her pussy to me, and for a moment I began to panic. Had I received another pain card? Was she about to smother me?

“You have to eat her out for a full minute,” Jennifer said by way of clarification. “I’ll be timing you guys on the computer.”

As Jillian settled onto my head, I felt my boner coming back. The furthest I had ever gotten with a girl before today was some kissing. I had never even seen or felt a girls boob. And now here I was, with each one of Jillian’s creamy pale thighs pressed against either side of my head and her pussy resting on my closed mouth. I was very aware of her heady scent, and I was finding it quite intoxicating.

“Alright,” Jennifer announced. “Ready, set, go!”

I didn’t quite know what to do, but I had seen enough porn in my life to have a general idea of what was expected of me. I opened my mouth and tentatively stuck out my tongue. When I made contact with Jillian’s lips, I thought I heard her moan, but I couldn’t be sure because my ears were currently blocked by her thighs. But she definitely shuddered a little bit. I took this as encouragement and thrust my tongue into her slit.

Her pussy actually tasted quite good, and it was quite slippery from all her juices. I started to explore, all the while hearing her muffled moans. After 10 or 15 seconds, my tongue discovered a large bump by the top of her pussy, and Jillian let out a loud squeal and almost lifted off of me. I had found her clit.

I attacked it with vigor, licking it this way and that way and even going so far as to suck it into my mouth. By now Jillian was thrashing around on top of me like she was riding a bucking bronco. The next thing I knew, her thighs locked around my head in a death grip and she let out a high, keening wail as my mouth was literally flooded with her sweet juices. She continued to shake for a good 15 seconds before she collapsed off of my head and onto the floor.

With the obstruction to my vision removed, I looked over to where she lay. Her eyes were closed, her face was flushed bright red, and she had the goofiest grin on her face.

Then I sat up and looked at my sister and Jessica. Both of them had there hands up their skirts and were stroking themselves vigorously. This time when they saw me looking, they didn’t bother to stop. My dick, which had already been rock hard, was now hard enough to stab Superman to death. If I didn’t get some relief soon, I felt like something would rupture.

After a minute or two, Jillian sat up and opened her eyes. “That was amazing Justin,” she said as she leaned in to give me a kiss on my cheek, which was still slimy from all the juices she had squirted on me.

I smiled and puffed my chest out at the compliment. Even though I was sitting here completely naked and had just recently had my nuts bashed in, I felt like a man.

“Okay,” Jennifer said. I looked up to see that she was once again sitting at the computer. “It’s my turn.”

Jennifer clicked the action card and sighed with relief. She had also gotten a pleasure card. The dice came up two.

She began to read. “Have a member of the opposite gender massage either your right or your left breast for 30 seconds with his hands. For this action you must remove all clothing above the waist. You must then leave them off for the rest of the game.”

“Wow, that’s awkward,” Jessica said. “Your own brother has to feel up your tit.”

“It could be worse,” Jillian said.

“It probably will get worse,” Jessica retorted. “This is still only the first turn of the game.”

“I think I’d be willing to do a lot for a hundred thousand dollars,” Jennifer admitted after a moments thought.

“Here goes,” she said as she started to take her shirt off.

I couldn’t believe my luck! I had been wanting to sneak a peak (unsuccessfully I might add) of my sister’s tits for years. Now, not only was she voluntarily taking her top off in front of me, I was going to get to feel her up too!

Her shirt fell to the floor revealing a lilac colored bra. If you had put a gun to my head, I wouldn’t have been able to pull my eyes away.

When she reached behind her to unclasp the bra, this had the effect of pushing her big tits out even farther. This in turn caused my eyes to pop out even farther.

Suddenly the clasp opened and the bra fell away from her breasts. I almost came, I was so excited at the sight before me. Two gorgeous, perfectly rounded orbs of happiness with the prettiest little pink nipples sitting proudly atop them. Clearly one of God’s finest works.

Jennifer looked up at me and noticed my ogling. She was clearly embarrassed, but trying hard not to show it.

Meanwhile, I just continued to stare like an idiot.

Finally, Jessica interrupted the silence. “Are you just going to stand there all day, or are you going to get some of your sister’s titty in your hand?”

Jillian giggled at this, Jennifer blushed a deep crimson, and as for me, that got me moving again. I think I briefly broke the speed of light in my haste to get to her. My hand was filled with lovely tit flesh before Jessica even had a chance to start the 30 second countdown.

As I stood there, I knew I was supposed to be massaging it, but for the first several seconds, I couldn’t even move. The idea that I had my sister’s tit in my hand was causing my brain to short circuit.

After a few seconds of this, I felt Jennifer press her breast more firmly into my hand, and this got me moving again. I started to rub the palm of my hand over her breast and gently palpate it. Then I began to lightly tweak her nipple with my fingers, causing a delighted gasp to come from her. I twisted it a few times too, and Jennifer’s knees started to buckle. I was about to take it into overdrive when Jessica called time.

It seemed like it was over even before it had begun. How Jessica was able to focus on the clock was beyond me, but reluctantly, I withdrew my hand from the most amazing piece of flesh it had ever come in contact with.

I noticed I wasn’t the only one who was upset. Jennifer seemed pretty put out that the fun was over herself. She surreptitiously gave her own nipple another little tweak before her hands returned to her sides. Apparently I had had quite the reaction on her. Score another point for my ego.

“Now it’s my turn,” Jessica said as she sat at the computer.

Wouldn’t you know it, she also got a pleasure card. Not that I was really complaining. I was enjoying their pleasure cards just as much as they were. She rolled a 4.

“Get a member of the opposite gender give you a lap dance for 45 seconds. You are allowed to touch him with your hands, but only above the waist.”

Jessica smiled and spun the chair around. “Get over here, stud,” she said, beckoning to me with her finger.

I was happy to obliged, and a large grin broke out on my face as I walked over to her.

“Wait,” Jillian said. “If he’s going to give you a lap dance, he needs some music to dance to.”

“Let me pull up my play list then,” Jennifer said as she walked over to the computer. “Move for a second,” she said to Jessica, who wheeled herself out of the way.

My sister bent over the keyboard, causing her tits to hang delightfully. As she typed, they jiggled ever so slightly. I never knew that typing could be so sexy!

A moment later, Lady Gaga’s “Just Dance” started coming out of the speakers. “Wait, let me get it to the good part,” Jennifer said as she advanced the song.

A moment later she paused the song and said, “I’ll start it whenever you’re ready.”

“I’m ready,” I said.

“Me too,” Jessica said hungrily.

“Okay, here we go then,” Jennifer said as she simultaneously restarted the song and started the clock.

As soon as the music started, I started dancing. I tried to imitate the women I had seen in the movies, but it was harder than it looked. Although it seemed that Jessica was enjoying it anyway. It looked like Jennifer and Jillian were too.

As I ground my butt into Jessica’s lap, I felt a hard slap on my ass.

“Hey, it said above the waist touching only,” I protested.

“It was an accident,” was Jessica’s flimsy excuse. I didn’t believe it for a second, but I also didn’t really mind.

After a few more seconds of grinding my butt, I become bolder and swung around to face Jessica. I straddled her, essentially sitting down in her lap, and placed each of my legs on either side of the chair. I started rocking my hips forwards and backwards as I continued to grind my crotch into hers. I could feel the heat of her pussy through her thin skirt and it excited me terribly. My dick had actually started to drip pre-cum onto her skirt, but both of us were too wound up to notice.

Suddenly, Jessica wrapped her arms around my waist and started gently stroking my back and sides. I moaned at her touch, and my dick started leaking even more. I leaned even farther forward and my dick poked right into her shirt. I was just starting to masturbate myself against her belly when Jillian called time.

“Crap,” I muttered to myself. I was starting to develop a serious case of blue balls from all this starting and stopping. I was beginning to feel a desperate need to cum.

“We’re going to need to find another way to keep track of the time,” Jillian said. “I almost couldn’t pull my eyes away to look at the clock.”

“I have a stopwatch in my bedroom,” I offered. “It beeps when the time is up.”

“Perfect,” Jillian said. “Where in your room is it? I’ll go get it.”

“It’s on my night table next to my bed.”

“Gotcha,” she said as she started for the door of the den.

Double crap. I was hoping I could have gotten it myself and rubbed out a quick one while I was gone. Even so, it was quite a treat to see Jillian’s nude ass as she walked away from us.

“And when you get back,” Jennifer said, “it will be Justin’s turn again.”

Triple crap. I didn’t know if I’d be able to survive another Pain card. I was starting to get a little worried.

[thisis4bbb]

This is just awesome. Keep going. I love it.

[xplayerone]

very nice keep going

[woodpecker]

This is a very exciting and entertaining story, I very much look forward to the next part!

[vandelescrow]

Keep it going, great story

[eggs2006]

Best story I read in a long time..........hope there's more. Sounds like his balls don't have a chance.

[korvas]

It was my turn again and I was nervous as Hell. I didn’t have much choice though did I? Not if I wanted to win that hundred thousand. With only a moment’s further hesitation I clicked on the card and watched it turn over.

I visibly sagged with relief when I saw it said pleasure.

“There you go Justin,” Jillian said supportively as she clapped me on the shoulder.

I rolled the dice. 2. Crap. Well I suppose any number on a pleasure card was better than pain.

“Have a player of the opposite gender give you a nude back massage. You must lie on your stomach and they must sit completely nude on your butt. This activity lasts for one minute.”

It may have only been a 2, but it didn’t seem so bad.

I looked at the three girls. Jessica was still the only one that was completely clothed. I needed to change that.

“Jessica,” I said pointing at her. “I want you to give me the massage.”

“You just want me out of my clothes,” she said with a smirk as she started to undress.

I watched raptly as she first removed her shirt and then her bra, exposing her fantastically large knockers.

Then she slipped out of her skirt and panties before kicking her shoes off. She did it all so fast that I didn’t really had a chance to appreciate her nakedness before she told me to lie down. I guess there would be plenty of time for me to stare at her later.

As I lay down, I was careful not to bang up my swollen nuts on the hard wooden floor. I rested my head on the back of my hands as I felt Jessica sit on my ass.

Her pubic hair tickled and scratched my butt as she wiggled around looking for a comfortable position.

I felt my dick start to stiffen again. This was not a good time to be getting a woody. Being crushed up against the floor the way it was, it had no room to grow.

“Ready, and go.” Jennifer started the clock and Jessica started my massage.

I’m guessing she didn’t have much experience giving massages, but it felt nice just the same. Just the idea of a hot naked girl rubbing her hands all over my body was quite pleasant. And the fact that she was starting to rub her groin back and forth along my ass only heightened my pleasure (and hers I’m sure).

As she worked, her hands crept from up near my neck down towards my lower back and then to the top of my ass. When she started to gently knead the top of my ass cheeks I felt my dick begin to stir again. I was beginning to wish that we had a couch in here. For the last 30 seconds of the massage, I had to split my focus between the pleasant sensations that Jessica was causing me, and not getting a boner. I was actually relieved when it was over and she got off of me as my dick was really starting to hurt. It seemed just my luck that even my pleasure cards would bring me pain.

After Jessica had gotten off me I stood up myself. That’s when I felt the unmistakable sensation of liquid running down my butt and the back of my thighs. Jessica’s pussy had leaked all over me! I suppose I wasn’t the only one who had enjoyed the massage.

Jillian was already at the computer clicking on her action card when I walked over.

“Pleasure again,” she said as she rolled the dice. She got a three, and the words appeared.

“Make out with the player of your choice for 30 seconds. No groping is allowed.”

She looked at me hungrily for a second, and then turned to my sister. “Get over here Jennifer!” she demanded.

“What!?” Jennifer startled. “You want to make out with me?”

“Yeah, baby,” Jillian said huskily.

Jennifer’s mouth opened and closed like a fish, but no sound came out. She was totally flabbergasted.

All of a sudden, Jillian burst out laughing. “Oh, I can’t believe you fell for that,” she screamed as she clutched her sides. Tears were streaming down her face she was laughing so hard. “You should have seen the look on your face; it was priceless!”

“Yeah, yeah, very funny,” Jennifer responded, no real anger in her voice. She was too relieved that she wouldn’t have to kiss Jillian to be too angry.

“So who do you really want to kiss?” Jessica asked.

“Isn’t it obvious?” Jillian said as she wiped her tears away. “The man with the magic tongue,” she said indicating me.

I blushed at this reference to what had happened earlier. I guess she was hoping that I could use my tongue to bring as much pleasure to her mouth as I was able to bring to her pussy. I hoped so too. I hadn’t had all that much experience kissing, but by all accounts I did a decent job. Granted, I was kissing girls my own age, not someone older like Jillian who was bound to have more experience than me.

“Alright, Justin, show her what you got,” Jessica said as Jillian strode over to me.

As Jillian wrapped her arms around my waist, I put my hands around her upper back, which to my consternation was still covered by her shirt. I would have to fix that at some point. As we drew close for the kiss, I felt my dick press up against her stomach. I quickly bent my knees a little, and suddenly my dick was nestled between her naked thighs, right up against her pussy. I was instantly hard, and Jillian parted her thighs and then closed them again around my dick so that it was trapped between them. I was so close to cumming and we hadn’t even started kissing yet!

Finally she placed her lips against mine and we started kissing. It was only closed mouth so far, but it was still absolutely amazing. But my lips weren’t the only thing feeling incredible sensations. While we were kissing I was thrusting my hips backwards and forwards, causing my dick to slide in and out of the warm tight spaced that her closed thighs had formed.

After two or three seconds of this, Jillian darted her tongue past my lips and into my mouth. The instant that happened I came. Like a fire hose. The pleasure was so intense that I couldn’t remain standing, and I fell to the floor as my dick continued to pump.

“Oh my gosh,” Jillian exclaimed, hand over her grinning mouth as I continued to lie there, spasming in pleasure.

“Hey, the thirty seconds aren’t up yet,” Jessica said, making no effort to cover her own grin.

“But-” Jillian began as she looked at me. Then, shrugging her shoulders, she got on her knees and crawled on top of me.

I was still experiencing aftershocks of the most intense orgasm of my life. I had been knocked insensate from the pleasure and was completely unaware of anything until I felt someone kissing my lips. I opened my eyes and saw Jillian once again trying to find every spot in my mouth with her tongue. I could feel the weight of her body on mine, her large breasts pushing pleasantly into my own chest, her warm legs resting on my own.

My hands instinctively wrapped around her as I snuck my own tongue into her mouth. I immediately noticed the taste of toffee. Why did girls mouths always taste like candy? As our tongues started dueling, I slid my hands down her back. I knew I wasn’t allowed to grope, but the card said nothing about me just resting my hands on her ass.

If I was to express how I felt laying there, I would have to say perfect contentment. Which is why I found it so difficult to let her up when Jessica called time.

With a groan of disappointment, Jillian released her lips from mine and got off of me.

I took a moment to stare at her bare pussy before I got up myself. It was coated in cum. So was the bottom of her shirt. So was my stomach for that matter. I must have cum all over myself, and when she lay down on top of me, she must have gotten it on herself as well.

“Hey Jillian, you look a bit sticky,” Jessica said as she pointed to Jillian’s nether regions.

“What?” Jillian said as she looked down. “Oh, gross,” she said as she spotted my goo on her. “It’s on my shirt too.”

“Let me get some tissues so that you can clean off a bit,” Jessica said as she headed for a box of tissues on the bookshelf.

“No that’s okay,” Jillian said as she reached for the hem of her shirt. “This is going to have to go in the wash now anyway.” Then she proceeded to lift her shirt over her head. I almost came again as she revealed a flat stomach and a pale green bra that was forming the most amazing cleavage. She then took the shirt and proceeded to wipe her groin with it. A moment later, satisfied that she had removed all of my cum from her nether regions, she threw the shirt into the corner of the room and grinned at me. “I think that’s the first time that anyone’s ever cum from one of my kisses before.”

I blushed terribly at that. “It wasn’t the kiss that did it,” I said rather embarrassedly. “It was the… you know.”

“Why, I’m not sure I know what you mean,” Jillian replied coyly as her grin got even larger.

I didn’t know how to respond to that, so I just stood there blushing until Jessica announced that it was Jennifer’s turn.

Jennifer wasted no time clicking on her action card. This time however, she was greeted with bad news. “Pain,” she said somewhat nervously.

“Hey, look on the bright side,” Jillian said. “At least you can’t get kicked in the nuts.”

“Yeah,” Jessica agreed. “It can’t be nearly as bad as that.”

“I guess we’ll find out,” Jennifer said as she rolled the dice.

The dice came up 4 and the words appeared. “Have one of the other players give you five slaps on the ass with a flat bottomed shoe. This action requires you to remove the rest of your clothes which will remain off for the rest of the game.”

“How boring and traditional,” Jessica yawned.

I didn’t think so. It meant that my sister would very shortly be completely naked. One man’s trash is another man’s treasure; one man’s pain is another man’s pleasure.

“Why did it say ‘the rest of my clothes?’” Jennifer asked. “How does it know I’m not wearing all of them?”

“It’s a computer program,” I piped up. “It must be keeping track.”

“I guess that makes sense,” Jennifer said as she stood from the chair.

She placed her hands on the waistband of her skirt and hesitated. “Justin, look away,” she said.

“What? Why? I’m gonna be seeing you naked anyway. What’s the big deal?”

“Just because you’re going to be seeing me naked, doesn’t mean you need to see me undress. A girl’s got to have a little privacy.”

“Whatever,” I replied nonchalantly as I turned around. I may have sounded casual about it, but I was actually quite upset. Not that it mattered too much I suppose. Like I had said, I would be seeing her completely naked in a second.

“Okay, you can look again,” Jennifer said after a moment.

I turned around, and almost fainted. My sister was gorgeous! Sure, I had seen her in bikinis plenty of times, and she had been topless for the past 20 minutes. But this was something else. She had a completely smooth shaven pussy with prominent lips that just begged to be sucked. Not that I necessarily wanted to go that far with my own sister, but you couldn’t help but notice them. And she had one of those sexy tan lines where everything is bronzed except for the small whitish area that the bikinis bottoms covered.

It was only at this moment that I realized that neither my sister nor Jessica had tan lines on their breasts. In fact, Jessica didn’t have them anywhere. Of course Jillian burned so easily that she never sunbathed, so she was pale even though it was summer time, but I wondered just how Jessica and my sister got such complete tans. Definitely something to look into.

“Okay,” Jennifer said, “we need a shoe.” A moment later she found her own discarded shoe and handed it to Jillian. “Five hits,” she said.

My hand started heading towards my stiffy, but at the last second I realized that might not be a good idea. Instead I grasped my hands behind my back and waited for the action to start.

“Do you need me to bend over?” Jennifer asked.

“No this should be fine,” Jillian replied as she walked behind her friend. “You ready?”

“Yeah, go ahead.”

Jillian swung the shoe back and slammed it into my sister’s round, plump ass.

“Ungh,” Jennifer groaned as the shoe made impact.

“One,” Jessica said, apparently taking upon herself the responsibility of counting.

Swing. Ungh. Two.

Swing. Oww! Three.

I was mesmerized. Every time Jillian swung the shoe into my sister’s supple ass it jiggled deliciously. Like Jello. The type you wanted to stick your face into.

Swing. OWW! Four.

My sister’s ass was beginning to turn red. Nice.

Swing. AHHH!! Five.

And that was it. Jillian dropped the shoe back on the floor. “Are you okay?” she asked my sister gently.

My sister turned around as she started massaging her ass. “Well, it’s the first time I’ve gotten a spanking in almost ten years, but I think I’ll live. I just won’t be sitting down for the next few minutes.”

Jessica went next. Like Jillian, she got her second pleasure card. The dice came up 4.

“Have two people do anything you want for your enjoyment other than oral sex or intercourse for 30 seconds.”

“Hmm,” Jessica mused. “Very interesting.” She paused in thought for a moment. “You know, I have to admit, that when Jillian asked to kiss Jennifer it got me excited. I want to see that.”

“Ha ha Jessica,” Jennifer began. “That joke’s already been played.”

“Who’s joking?” Jessica remarked innocently. “I’m not joking. I really want to see you and Jillian make out. Or I could just ask you to make out with your brother.”

Jennifer looked at me. It looked as though she might find that preferable. Jessica noticed this too and put a stop to it before it could lead anywhere.

“No, on second thought, you have to make out with Jillian.”

“But why?” Jennifer moaned as she started walking towards Jillian, a look of dejection on her face.

“Because sometimes I just like to be mean, that’s why.”

“Yeah, well you’re being a real bitch alright,” Jennifer agreed.

It suddenly occurred to me that through this entire altercation, Jillian hadn’t said anything. She looked as if she was simply waiting to kiss Jennifer. Not in an overly eager way or anything, but she certainly didn’t look sick about it like Jennifer did. This was something else I was going to have to look into.

Jennifer approached Jillian, and for a moment she couldn’t figure out where to put her hands. This was a girl that she had hugged a million times before, and now she was treating her like a hot stove. Finally her hands came to rest awkwardly on Jillian’s shoulders.

Jillian on the other hand, easily slipped her own hands around Jennifer’s waist.

Jessica stepped right next to them. “I wanna see tongue too, okay?” Jennifer didn’t say anything to this, but she did flash Jessica a nasty look.

Jessica picked up my stopwatch. “Ready, begin.”

Jillian made the first move, bringing her face right up to Jennifer’s and pursing her lips out so that they just touched her friend’s. After a moment of contact that met with no resistance, Jillian mashed her lips into Jennifer’s a little harder and started rubbing them around.

Like a switch had been flicked, Jennifer finally started moving. She started to rub back and this seemed to really excite Jillian, who suddenly grabbed Jennifer’s lower lip between her teeth and started to nibble on it. Jennifer moaned, which caused her to blush, as she was still in denial that she could actually be enjoying herself as she kissed another girl.

Taking the moan as a affirmative, Jillian moved in for the kill. She thrust her tongue straight into Jennifer’s mouth, where Jennifer proceeded to suck on it quite vigorously. This caused Jillian to start moaning and shivering, and her hands, which had been resting on Jennifer’s lower back, slid down to Jennifer’s naked ass where they gently massaged her luscious globes.

Although they had only been going at it for ten seconds, they had already reached such a frenzied state that had an earthquake began at that moment, they would have dismissed it as their racing hearts.

Jennifer’s hands finally relaxed and likewise slid down to Jillian’s butt. And while she wasn’t exactly massaging it, it didn’t look like she was planning on letting go any time soon.

Meanwhile, I couldn’t contain myself anymore. Watching my hot, nude sister make out with her equally gorgeous friend was too much for me to take. I was stroking my dick for all I was worth. The two girls were oblivious of course, but Jessica noticed and gave me a smirk. I didn’t care who saw though. This was one of the hottest things I had ever seen in my life. In fact I was enjoying it so much, my eyes started to close involuntarily from the pleasure, even though this kind of impeded my view.

I was half gone with lust and pleasure, stroking my meat with utter abandon, when a voice startled me out of my self service.

“Did you enjoy the show little brother?”

I looked up to see that Jennifer and Jillian had finished their make out session, and now all three of the girls were watching me stroke my dick with large grins on their faces.

For some reason, even though I was currently experiencing the most humiliating moment of my life, my dick seemed to enjoy the attention, because the next thing I knew, I was spurting again.

My first blast shot out like a cannon, spraying in a straight line from the bottom of my sister’s breasts right down to her belly button.

She squealed and jumped out of the way, exposing Jessica as a target.

Like a homing missile, my second shot, which was even more intense than the first, sprayed Jessica directly across the face, getting both her cheeks and her nose with a copious amount of my creamy white fluid.

My next four spurts could have ended up on the moon for all I knew because I was so lost in pleasure that everything else ceased to exist for me.

I must have been laying there for close to a minute before I was able to open my eyes again. The first thing I saw was Jennifer handing Jillian’s already soiled shirt to Jessica, who proceeded to wipe her cum-soaked face with it.

“I guess that answered my question,” Jennifer said to me with a giggle as she scooped some of my cum out of her belly button.

Jessica finished wiping her face and threw the now completely cum covered shirt back on the floor.

“If you cum on me again, I’m gonna rip your dick off.” Even though she said it like she meant it, there was a sparkle in her eyes that I didn’t quite know how to interpret. She looked at the other two girls. “I’m going go wash the rest of Justin’s cum off my face. We’ll start round 3 when I get back.”

I just lay there and stared at the three girls, completely unmoving. This had turned into the best day of my life, and I definitely wanted more, but I don’t think I had enough energy left in me to scratch my nose, let alone play 8 more rounds of this game. This thought was making its way through my head as I drifted to sleep.

[jacall]

Wow! A tip of the hat to you sir, I cannot wait to read the next installment!

[squish]

korvas- this story is great. I hope you keep it going!

[saintpates]

please continue the story!

[korvas]

Sorry this next installment was such a long time coming. But the wait is over. Enjoy!



A gentle nudging of my shoulder woke me from a most wonderful slumber. “Justin,” my sister said. “Wake up. It’s your turn.”

I opened my eyes to see my sister crouching in front of me. My eyes were instantly drawn to her pussy, which was spread wide open from the position she was in. It glistened a healthy pink. She noticed where my eyes were looking and blushed before standing up.

“Yeah, okay,” I said after a moment. I didn’t really feel like moving but I guess I didn’t really have a choice.

Rising to my feet, I headed over to the computer and clicked on the action card. It flipped over to reveal pain. It seems my fun was over for the time being.

When I rolled the dice the number 4 came up.

“Take your testicles and place them on a hard surface such as a table and then have another player smash them with a hardcover book. Your penis must not get in the way or the process will be repeated.”

“I wanna do it,” Jessica said with determination. “To get back at him for cumming in my face.”

I gulped audibly. Thus far we had been playing for a chance to win the money. But now it seemed like Jessica wanted to get revenge. It seemed like she actually wanted to hurt me. I didn’t want to have that happen.

“Actually,” I said, speaking up, “I’d rather one of the other girls did it.”

Jessica frowned at that. “Whatever. I’m sure I’ll get another chance to bust you later.”

“So who do you want to do it?” Jillian asked.

Even though my balls weren’t hurting from round 1 anymore, I still remembered how much it had hurt at the time. I wanted to diminish any anguish I might have to experience. So on the one hand there was my sister, who being my sister would potentially go easy on me. On the other hand, Jillian had a major thing for me and she might go easy on me for that reason. In the end I chose Jennifer. She was family. She’d take it easy on me, right?

“Okay,” she said as she headed over to the bookshelf. There were a lot of books on the shelves, and several of them were hardcover. I figured she would take one of the ones from the middle shelves; one of the novels my father liked to read. Instead she reached for the bottom shelf and brought out Webster’s unabridged dictionary. All 1100 pages of it.

I guess I was wrong about her taking it easy on me. “I think that’s a bit extreme,” I said. “Why don’t you take one of the smaller ones?”

“This fit’s the criteria,” my sister replied as she struggled to bring it over to where I was standing. It must have weighed over 20 pounds.

“What should we use as a hard surface?” Jessica asked gleefully.

“Here,” Jillian said as she walked towards the end table next to the couch. She moved the lamp off of it and brought it over to where the rest of us were standing.

“Put your balls up there squirt,” Jennifer said.

I refused to comply.

“Oh for heavens sake,” Jennifer said rolling her eyes. “Jillian, get his nuts up on the table for me will you?”

“Sure,” Jillian said as she reached for my low hanging balls.

Even though I didn’t want her to come near me, I let her do it anyway just so that I could feel her handling my balls. My joy was short lived however, because a moment later my nuts were resting on the table and her hand was gone.

Jennifer was just raising the book up to give my balls an almighty smashing when I shouted out “wait!”

She paused mid swing. “What?”

“My dick is in the way,” I said indicating my limp dick.

“So do something about it,” Jennifer replied.

“I got it,” Jillian said, once again coming to my rescue (doom?).

She started stroking my cock, and sure enough, after only a few seconds of her soft warm hands jerking my meat, my dick started to rise out of the way. “That’s a good boy,” she cooed at my penis, as if she were talking to it directly. Then to my surprise, she bent down and kissed it on the head.

My cock lurched, and Jennifer must have seen that as her signal because all of a sudden Webster was hurtling towards my nuts.

THWOCK!!!

The impact was deafening. The pain was blinding. My mouth popped open but no sound came out. I couldn’t even see my balls underneath the massive book that had just smashed into them.

I started to fall to the floor, but my balls were trapped underneath the dictionary. As they tried to pull free from their tormenter, my balls pulled the dictionary with them, and as I collapsed to the floor, the dictionary came with me, landing on my nuts for a second time.

As I groaned feebly, I heard the girls laughing at this. I saw them standing there giggling and furiously rubbing their bare pussies. They really seemed to get off on my pain. I guess I was glad that somebody was enjoying themselves.

Gingerly, I moved the dictionary off of my nuts and gently felt my balls to make sure they were okay. Other than being a bit swollen (and very painful to touch) they seemed to be fine. My inspection was interrupted by Jennifer gasping.

I looked up to see her fingers plunging in and out of her juicy snatch. Then with a scream, she jammed them all the way in and her whole body started thrashing about. Her orgasm was so powerful she practically collapsed to the floor. I can’t believe my own sister had cum from smashing my balls!

I just stared in awe at my sister’s spasming body as her juices ran down her thighs. It was definitely a hot sight, and I would have enjoyed it much more had my balls not been aching so much.

“If everyone is finished enjoying themselves,” Jessica began, her own fingers still lightly rubbing her cunt, “then it’s Jillian’s turn.”
@@@@@

Jillian got her first pain this time. And a level five no less.

“Soak a towel in water, twist it into a ropelike structure, and then have the strongest player smack it into your bare breasts for 45 seconds.”

“That actually doesn’t seem so bad,” Jillian said as she started to remove her bra; the last article of clothing anyone in the room was wearing. Her bra fell away, revealing a pair of perfect milky orbs, topped with two candy pink nipples. They looked like the type that were made for sucking.

“I’ll go get the towel,” Jennifer said as she headed for the kitchen.

Jillian didn’t think it would be too painful, but I knew differently. When I was younger and used to go to camp, often times after swim, I would be subject to ‘rat-tail snaps’ as they were known. One of the guys would smack his wet towel into my but. And even through my bathing suit, it still hurt. Jillian was going to be getting it on her sensitive bare breasts, and for 45 seconds. I found that I was looking forward to it.

Jennifer came back in with a bath towel that was twisted up and soaking wet. “Here you go Justin,” she said as she handed me the towel.

I took it from her and looked at Jillian who was staring at me apprehensively.

“Be gentle,” she said quietly as I approached her.

I had no intention of going gently. I wasn’t planning on killing her with it, but after all the pain I had received so far, I relished the idea of dishing out some of my own.

I drew my hand back, preparing for the first swing, and looked to Jessica, who had my stopwatch in her hand.

Her eyes flicked up to meet mine and she gave me a flirty grin. Then she pressed the button and said “go!”

The moment the word left Jessica’s mouth, my wrist flicked and the towel went zinging right into Jillian’s large right breast. It hit the nipple dead center and I watched in awe as ripples spread throughout her boob meat, causing the whole boob to reverberate with the blow.

Jillian was also in awe, but of a different kind. At the moment of impact, her mouth had formed an O and her hand had come up to clutch her breast. I guess she hadn’t been expecting it to hurt so much.

As she was moaning her pain and massaging her breast, I smacked the towel into her exposed left breast. She cringed and let out a small shriek as her other orb was exposed to the onslaught.

Now she was massaging both breasts.

“You have to move your hands for me to continue,” I said as I wound to the towel tighter.

“It hurts too much,” she pleaded, her teary eyes looking into mine.

I felt a little sorry for her, but a part of me was also relishing her pain. So I used the same card they had been using on me the whole time. “If we’re going to win the 100 thousand, you need to co-operate.”

She reluctantly moved her hands, and I whacked her right breast again.

“Ow!” she screamed out, and her hand instinctively came to clutch her injured breast again. But this time she immediately removed it.

After a few more hits, she was actually beginning to cry, and I softened my blows just a little bit. But not too much; we did after all have an audience, and I didn’t want to jeopardize our chances of winning that money.

I had just hit Jillian’s left breast with another blow when Jessica called time. By this point Jillian had tears streaming down her cheeks and her tits were bright red.

As soon as Jillian had called time, she started to massage them, trying to rub the pain away.

I was feeling very bold after this latest experience, and that’s what made me say what I said next. “I think I can help you with that pain a little,” I said to Jillian.

“How?” she asked through tear streaked eyes. “May I?” I said, indicating her breasts.

She eyed me warily for a second; after all, I was the cause of her new found pain. But after a moment she nodded her head and removed her hands.

I slowly moved in, and gently placed my hands on either side of her breasts. Then I moved my head in and started to suckle on her nipples. Jillian was startled for only a moment before she started to moan her pleasure.

“Ooohhhh, that does feel nice,” she cooed in pleasure. Her hands went to the back of my head and held me tightly as I feasted on her precious breasts. I switched from one to the other a few times before, hands still on my head, Jillian pulled me up and gave me a sexually charged kiss that almost blew the top of my head off. Her tongue was in a frenzy, exploring my mouth like a poison victim looking for the antidote. I groaned back into her mouth as I returned the attack, and for a good minute, we stood there making out like two lust crazed animals, which I guess is what we were.

“Ahem,” Jennifer finally said. We broke away gasping as we both looked at my sister. “Intermission’s over,” she said, a grin plastered across her face at witnessing our antics. “It’s my turn.”

@@@@@

Jennifer got another pleasure card. This time she rolled a 1. “Have a player of your choice do a sexy dance for 10 seconds.”

“What a rip-off,” she protested.

“Better than nothing, I guess,” Jillian said with a shrug.

“Barely,” Jennifer returned.

“You,” she said pointing at me. “Start dancing. And lots of pelvic thrusts. I wanna see your dick bouncing around.” Her tone was angry. I guess she felt she was being cheated. Well, there was nothing I could do about that.

Jessica said go, and I started dancing. I wasn’t very good, but it didn’t stop the girls from drooling over me. My dick swung, my ass shook, and the girls followed my every move with lust in their eyes. But almost as soon as I had started, it was over.

“That was so cheap,” I heard my sister mumble. “Only ten fucking seconds.”

“Okay,” Jessica said as she went to draw a card for herself. “Maybe I can provide us all with a little more entertainment.”

She drew a pleasure card, her third in a row. And this time the dice landed on six. “Have sexual intercourse with the player of your choice for two minutes.”

“Holy shit!” Jennifer exclaimed when she heard what Jessica had to do.

“I’m a virgin,” Jessica said softly, almost to herself, as she stared at the card.

I was too, but that wasn’t so strange. After all, I was only 13. But I wouldn’t be a virgin for long!

Without my even realizing it, my dick had gotten hard as an iron bar. My dick was anticipating sex with Jessica just as much as I was.

“I guess you guys should just do it,” Jillian said. And I could’ve sworn that there was a touch of jealousy in her voice.

“Yeah,” Jessica agreed, although her fear and trepidation were quickly being overtaken by animalistic lust. She actually subconsciously licked her lips as she turned to me.

“Where are we going to do it?” she asked, looking around the sparsely furnished office.

“Why doesn’t Justin sit on the computer chair and you straddle him,?” Jennifer suggested.

“Ok,” I said and took a seat in the chair.

As Jessica was walking over to me, her eyes suddenly flew wide open and she stopped short.

“I’m not on the pill,” she exclaimed.

“Uh oh. What do we do?” my sister asked.

“It’s only for like two minutes,” Jillian said. “You can keep yourself from coming for two minutes, can’t you Justin?”

“Yeah,” I said, thrusting my chest out in a manly pose. “I can handle it.”

“I’m still not sure,” Jessica said, biting her lower lip nervously as she stared at my dick, which was sticking straight up out of my groin.

“I looked at the uncertainty and lust that was warring in her eyes and played my trump card. “One hundred thousand dollars,” I said seductively.

Like a barrier had been broken, the tension in Jessica’s face melted away. “Oh, fine,” she said and walked right over to me and spread her legs. Her pussy was now directly over my raging dick. Maybe a foot was all that was separating me from heaven.

Jillian picked up my stopwatch. “You have two minutes,” she said. “Ready, go!”