Jenny

byTryAnything©

John peeked through the hole he had made in the closet wall connecting his room to his sister's. He could see his sister in her room beginning to undress for bed. As he became more excited watching her undress, John dropped his pants and pulled his cock out, holding it in his hand. Even though Jenny was only 19, John knew that she was already mature physically, with big full tits and a pussy that could clearly be seen through the sparse red hair growing there.

John was only a year younger than Jenny and big for his age, so most people thought he was the older of the two. He had made the hole in the closet about three months ago and had been regularly watching his sister in her room. He had been surprised to find that Jenny liked playing with herself, squeezing her tits and pulling on her nipples, trying to lick them, and that she played with her pussy, sticking her fingers into it and also in the last couple of weeks a big black dildo that she had gotten somewhere. John got so hot watching Jenny that he would regularly masturbate, trying to cum when she did. Because Jenny almost never closed her closet door, John was usually able to see her, like tonight.

Slowly he pulled on his cock as he watched Jenny undress. When she had pulled her shirt off, she cupped her tits in her hands, hefting them, weighing them, squeezing them. John knew her routine almost by heart. Then she pinched her nipples in her fingers and pulled on them, twirling them. Very quickly John could see them harden, knurling into knots on the ends of her tits. Jenny hefted one of them upwards, sticking out her tongue and flicking it at the nipple, just barely able to reach.

Then Jenny wriggled out of her jeans, pulling them off and revealing that she wasn't wearing any underwear. This had been going on for about two weeks now. It had really excited John the first time he realized that Jenny hadn't worn any underwear, going out with just her clothes covering her.

Sitting down on the edge of the bed facing the closet, Jenny spread her knees wide apart and rubbed her hands in her pussy. John almost died on the spot when Jenny's hands came from her pussy, pulling the big black dildo out. He couldn't believe that she had been in school all day and eaten dinner with their parents with that big black dildo jammed up into her pussy.

Suddenly John began to cum, splashing all over the closet wall as his balls exploded while he watched his sister. Jenny slid the dildo in and out of her pussy several times, then pulled it all the way out and brought it up to her mouth, opening it and sliding the dildo into her mouth, sucking on it, licking all of her own pussy juices from the dildo.

John was still furiously rubbing his cock, staring at Jenny's wide open pussy staring at him, only about ten feet away. He could see her pussy lips pouting open, revealing her clit sticking out from between them and her hole, pooling with moisture. After sticking the dildo back into her pussy and ramming it in and out several times, Jenny licked it off again and turned off the light, ending John's show.

John groaned as the light went out, depriving him of his entertainment. But he had cum once, he smiled to himself, and really busted a nut. God, Jenny was great, he thought. He wondered if she had ever been with a guy yet. Probably, he thought. She was probably the horniest person in the whole world, the way she had been carrying on. No, John corrected himself, I'm the horniest person in the whole world.

And Jenny never acted any different. She was still the sweetest sister in the world, always helping him if he had any trouble with his schoolwork, a cheerleader, straight A student, teacher's pet, the whole nine yards. And yet she was so beautiful and perverted, John thought as he climbed into bed. He couldn't wait to get come pussy for himself one day.

The next day John was at the hole in the closet waiting when Jenny woke up. He watched as she stretched, throwing the covers off, then pulled up her knees and spread them wide, her hands going right to her pussy. John watched as she rubbed her clit, slowly, and gently slid several fingers into her pussy as she masturbated. When she finally came, John did too, this time catching his cum in his hand and using it to lubricate his cock as he continued to pump it in his hand. Then Jenny jumped up and went to the shower.

Cleaning himself up, John got dressed and went out of his room to have breakfast with the rest of the family. His mother Jean was such a beautiful woman, John noticed again, her long blonde hair reaching down to her waist. She had such a beautiful smile. His father Jack was tall and red-headed just like Jenny. He had a great sense of humor and John loved it when they would go camping or hiking in the mountains together.

As John and Jenny walked to school together, John began to have the beginnings of an idea in his head. Money was always a little short and he was constantly thinking of ways to get just a little more. Now maybe he had an idea. He hadn't told any of his friends about Jenny, mostly because he was sure they wouldn't believe him, but also because he didn't see any advantage in his friends knowing that his sister was such a horny, sex pervert. Now maybe he could solve all his problems at once.

Once at school that day, John pulled his two best friends aside, Harry and Tom, and asked them if they had ever seen a girl totally naked. Their surprised expressions told him the answer to that one immediately.

"What would it be worth to you if I could guarantee that you'll have a perfect view of a naked girl from only ten feet and that she wouldn't know about it?" John asked.

"I'd give you all the money I'll make for the rest of my life," Harry said excitedly. "But you couldn't possibly deliver so it's a dead issue."

"But what if I tell you I can deliver," John continued. "How much would you pay?"

"How long would we get to watch?" Tom asked.

"Well, probably five to ten minutes," John said after thinking about it for a moment.

"Just to see a naked girl?" Harry asked. "What is she, twelve years old?" he asked, laughing hard.

"No, she's nineteen and beautiful, and if you come up with the right money, I'll even guarantee that she'll play with herself too," John said. "So, what do you think?"

"Shit, I'll pay to see that," Harry said. "I'll give you $20 if you let me see that."

"What about you, Tom?" John asked. "You willing to pay to see it too?"

"I guess so," Tom said. "But what if it's not what you say, then what?"

"Then you don't have to pay me," John said. "In fact, I'll let you pay me after, that way you decide if I was telling the truth."

"That sounds fair to me," Tom said. "I'll give you $20 if it's as good as you say."

"Great then," John said, thinking of the $40 he would make. "What you have to do is get your parents' permission to spend the night at my house, then I'll be able to show you."

"How about tomorrow night then?" Harry asked. "I'm sure my parents won't mind."

"Yeah, I think my parents would let me tomorrow night too," Tom said.

"Great, then tomorrow night," John said. "I'll talk to my parents and make sure, but let's plan on it."

"Great," Harry said, jumping up excitedly. "I can't wait."

That night as John watched Jenny again, he couldn't contain his excitement at watching his friends see her without her knowing about it. And $40, that would sure help. As he expected, his parents had no objection to him having two friends come over to study and spend the night, so the next day after school both Harry and Tom came home with him. They spent the afternoon studying, to keep up pretenses, and after dinner used studying as an excuse to go to John's room.

"So, when are we going to go see this naked girl?" Harry asked impatiently.

"It won't be long now," John said with a smile on his face. "Are you sure you're ready for this?"

"Quit wasting time and get on with it," Tom said. "Or is this just some bullshit?"

"No bullshit," John said. "In fact, we can start getting ready."

Moving over to the closet, John opened the doors, first turning out the light in the room. Motioning to Harry, John pointed out the hole in the closet wall.

"You just keep your eye on that hole," John explained, "and in just a minute or so it'll start."

Tom just looked at him as Harry bent to the hole, putting his eye to it. They all waited, fidgeting as nothing happened. Then suddenly Harry gasped.

"Hey, it's your sister," he said.

"I know it is," John said smugly. "Just keep watching."

"You mean you're talking about your sister?" Tom asked him incredulously.

"Uh-huh," John said. "And you won't be sorry either."

"Your sister," Tom said, shaking his head in disbelief. "I can't believe you'd sell a peek at your own sister."

"Why not?" John asked. "She doesn't know and it won't hurt her. And you said you'd pay $20 to see."

"Oh, wow," Harry whispered. "She's taking off her shirt. What outrageous tits! Man, they are beautiful."

"Let me see," Tom said, suddenly interested again.

"Let Tom look for a minute," John said. "Then you can look again. You'll have to take turns. And you can see again in the morning, too."

Quickly Tom knelt down and looked through the hole, just in time to see Jenny twisting and pulling on her nipples.

"Oh, man, she's beautiful," Tom said softly, his eye glued to the hole. "Oh, god," Tom said. "She's taking off her pants. I can't believe this, she's not wearing any underwear. Oh, man, what a beautiful pussy."

"Let me see, let me see," Harry implored.

"Let Harry look, Tom," John said, smiling as he realized that they were hooked.

Harry quickly dropped to his knees, his eye pressed to the hole.

"Wow, what a pussy," he exclaimed. "I can't believe she's playing with herself like that. You can see everything in her pussy. Oh, god, she just put her fingers up into her pussy."

"Let me see," Tom begged.

Moving aside, his eyes bright and a slight bulge present in his pants, Harry let Tom have access to the hole.

"Oh, man, I just can't believe anything could be so beautiful," Tom said as he looked through the hole. "She's just amazing. Hey, what's she doing?" Tom asked suddenly. "She got up and turned off the light."

"She's going to bed for the night," John explained. "But you can see again in the morning."

"How can I possibly sleep knowing that she's over there?" Harry moaned.

"It took me a little while to learn to do that," John admitted with a smile. "But it makes for great dreams."

"I can't wait for morning," Tom said.

"Does that mean you're going to pay me?" John asked.

"You bet," Harry said, pulling a $20 bill from his pocket and handing it to John. "It's a bargain."

"Yeah, you sure didn't lie," Tom said, handing John $20. "I still can't believe it. My dick's so hard I think it's going to break."

"Just wait until morning," John said, getting undressed for bed. "It's a great way to wake up."

The next morning the three of them were waiting in the closet for Jenny to wake up. When she did wake up, Tom insisted on first look because Harry had gone first last night. Placing his eye to the hole, Tom watched as Jenny woke up, stretching, then throwing the covers off and pulling her knees up and apart.

"God, she plays with herself first thing in the morning," he breathed, staring into the hole.

"Let me see," Harry said.

As Tom moved aside, Harry put his eye to the hole, drawing a loud breath as he saw Jenny's pussy totally exposed to his view, her fingers busy in her pussy. Then Harry gasped, choking as he tried to talk. It took John a minute or so, but finally he succeeded in moving Harry from the hole so that Tom could look.

"Oh, shit, look at that thing she's shoving into her pussy," he said. "I can't believe it fits. This is just great."

"Let me see some more," Tom said, elbowing Harry aside and pressing his eye to the hole. "Oh, man, look at that. She's fucking herself with that fake black cock. Unreal. I can't believe that's your sister doing that," he said. "She seems like such a nice person."

"She is a nice person," John said. "She's also a very horny person, I'd say."

Suddenly Tom moved back from the hole, his mouth wide open and his eyes sticking out of his head.

"She licked it," he said. "She licked it after it was in her pussy."

"Oh, my god," Harry said as he looked into the hole. "She's sucking that thing, licking it off. Oh, shit, she's leaving the room," he said turning away from the hole.

"She's going to take a shower and get ready for school," John explained, moving from the closet.

Harry and Tom were extremely excited as they left the closet, their cheeks burning with color and definite bulges in their pants. They could barely contain themselves as they all walked to school together, Jenny again the model of sweetness and respectability that they had known her to be. For the next week or two Harry and Tom found every excuse possible to spend the night at John's house, each time paying him another $20 for the privilege. Soon John had several hundred dollars saved and was thinking about how to increase his take.

For two weeks John thought about what to do, how to make this even more profitable. Finally he decided on a plan of action, but he was very nervous about implementing it. One day he decided he had enough courage, and knocked on Jenny's door one afternoon when he was sure she was doing homework, having checked by looking through the hole.

"Yes," Jenny said, "come in. Oh, hi, John," Jenny said as he came into the room. "What are you up to?"

"Well, there's something I'd like to talk to you about," John said hesitantly.

"Well, what is it?" Jenny asked, smiling at him.

"It's about money," John began.

"John, you know I don't have any money," Jenny said. "I can't possibly help you there."

"Well, actually there is a way," John said, "and I think I can help you with money too."

"John, what are you talking about?" Jenny asked.

"This," John said, suddenly reaching under the mattress where he had seen Jenny hiding her dildo and pulling it out.

"Oh, my god," Jenny said, her face turning beet red and her hands covering her mouth. "How did you find out about that?" she asked, tears starting to come from her eyes.

"Don't cry, Jenny," John said, feeling terrible that he had upset her so.

"How could you know?" she asked, crying. "How could you possibly know? You're not going to tell Mom or Dad, are you? They'd never understand."

"No, I'm not going to tell Mom or Dad," John said. "I'm not here to make trouble for you, I just know how to get money and I thought I'd share it with you."

"But what does money have to do with this?" Jenny asked, indicating the dildo which John had tossed onto the bed.

"I know what you're doing with it," John said. "I've seen you."

"You've seen me?" Jenny exclaimed. "How could you?"

"Here," John said, going over to the closet and pointing out the hole in the wall. "I watch you from here."

"Oh, god," Jenny said, bursting into tears again. "I can't believe this is happening."

"Jenny, I'm not mad or anything. And I don't think there's anything wrong with it either. But I do watch and I like watching," John said.

"So, what do you want then?" Jenny asked.

"Well, you know Harry and Tom?" John asked. "Well, I've been charging them $20 each to look through the hole at you."

"Oh, no," Jenny cried, tears pouring down her face. "What have you done? They'll tell everyone at school and I won't be able to look anyone in the face ever again."

"No they won't," John said firmly. "They know that they can't say anything. First of all, who would believe them? About you, I mean. And besides, I told them I'd never let them see again if I even thought that they had told anyone."

"And you believe them?" Jenny cried. "You've destroyed me."

"Yes, I believe them," John said, "and no, I haven't destroyed you. Look at this," he said, holding up a wad of money. "There's more than $400 here."

"$400," Jenny said. "How did you get so much money?"

"I told you, I made them pay me $20 each every time they wanted to watch you," John explained. "And I know how to get even more. But I'll need your help for that."

"You want my help?" Jenny almost screamed. "Are you crazy?"

"No, I'm not," John said. "Just hear me out, okay? Look, I'll split the money with you, even this," he said, holding up the wad. "But I have an idea to get even more, lot's of it."

"I can't wait," Jenny sniffed. "How are you going to do that?"

"Do any of your friends know what you do?" John asked. "You don't have to tell me their name."

"Yes, one friend does," Jenny admitted.

"Well, if you can get her to come over here and do it, I can get my friends to pay to see," John said. "She wouldn't even have to know."

"But I'd know," Jenny said. "And she's my friend. She's the only one who knew and that I could talk to."

"Well, now I know and we're talking, aren't we?" John asked. "I just see us being able to make lots of money for the summer. Think of the fun we could have when Mom and Dad go away for their two weeks if we have money to spend. We wouldn't just have to stay home. We could go to the beach, take the train, or go camping in the mountains, take the bus. But we could at least do something. I'm tired of going back to school and listening to all the fun everyone had because they could afford to go somewhere. I want to have a great summer too."

"What if I say no?" Jenny said. "What then?"

"You won't say no," John replied. "It's a great idea and it doesn't hurt anyone. Harry and Tom think you're a goddess. They absolutely worship you. I don't think they think of anything else all day long except you. Nobody will do anything to jeopardize the chance to see."

"And if I say no, I won't do it?" Jenny said. "I could just close my closet and then you'd be left with only your memories and imagination," Jenny said.

"Please, Jenny," John begged. "Think about it. I mean, it's obvious that you're horny and so you play with yourself to feel better. Doesn't it excite you at all knowing that you're able to get someone else so excited watching you that they masturbate themselves?"

"I do that?" Jenny asked. "You mean Harry and Tom?"

"I've never seen them, but I'd bet anything that as soon as they get home they masturbate every time," John said.

"And what about you?" Jenny asked. "Do you masturbate too?"

"Yes," John said, his head down and his voice barely audible. "I think you're the most beautiful, exciting person in the whole world."

"What do you do?" Jenny asked, her curiosity peaked.

"I watch you and play with myself," John answered. "Like you."

"And do you -- you know," Jenny asked.

"What?" John asked.

"Do you cum when you masturbate?"

"All the time," John nodded. "I try not to cum until I see that you're cumming, but I'm not always successful. You excite me so much at times that I can't even control it."

"I can't believe this," Jenny said, moving over to the bed and putting the dildo back under the mattress.

"Look, Jenny," John said, "I'll give you half of the money I've already gotten. Please just say you'll think about it, give it a try."

"This is a lot of money," Jenny said, holding the wad of bills that John handed her.

"As far as I'm concerned, you earned it," John said. "You'll think about it?"

"Under one condition," Jenny said.

"Name it, anything" John said desperately.

"You've been watching me, right?" Jenny asked.

"Yes," John said.

"Then I want to watch you," Jenny said.

"What?" John asked.

"Masturbate for me," Jenny said, "right now."

"What?" John said. "I can't. I'd be too nervous."

"Then I won't even think about it," Jenny said.

"You'll really think about it if I do?" John asked.

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