Hi this is lucky and I’m going to tell you my friend jacks story. Jake should have been able to get along great with girls. After all he grew up around a houseful of women, being the youngest of five siblings. He was the only boy and his four sisters almost constantly antagonized him. Despite all the women in the house, and all the experience he had talking to girls, he had nearly zero luck with the opposite sex. Which was actually more like absolutely zero?
He was a eighteen year old virgin growing up with some of the hottest girls ever and he couldn’t use their advice to even talk to a girl and get himself a simple date. His four sisters Lindsey, Jessica, Sarah and sandy were gorgeous beyond belief. They lived with their mother, Jane, who was a district attorney who worked a lot, but made enough money for the girls to go to college and Jake to pursue his dream of being a guitar superstar. He and his sisters helped out by cooking and cleaning along with being fairly good students so as not to waste Jane’s hard earned money. Jessica was the oldest at twenty-four she was racking her mind in her third year of college trying to earn a medical degree. She was a rather stunning young lady with honey brown hair and green eyes. Her body was thin and nimble as she worked out a lot, but all of Jake’s sisters did. Jessica had a few boyfriends in high school but once she started college she seemed to stop dating completely. Sandy had begun to call her a lesbian.
Lindsey was next in line at twenty-two, and a total health nut. She counted every single thing that went into her body and even kept a calorie journal so she wouldn’t go over her allotted amount of food for the day. She was studying business and still debating on weather to move into law. She had dark brown hair with gold highlights. Her hair was the longest out of all of them falling halfway down her back. Jake did go through a heavy metal phase where he had his hair longer than Lindsey’s but one day the girls held him down and cut his hair because he looked stupid. Jake and Lindsey got along together the best though. Sarah and sandy were the twenty-year-old twins who fought to be different from one another. Sarah was an art major and was a very talented painter and artist. She had dyed black hair which gave her a sexy gothic look, although she did not wear gothic make-up. She was hot and almost always had what she called a “boy toy”. She spent a lot of time with friends as well. She and Jake never got along either, and they fought every day. Or at least they teased each other which then lead to fighting.
Sandy was very quiet and had not yet decided what to major in. She studied very hard though and almost always had a book in her hand. Sandy had nice soft blonde hair and was the sweetest person Jake had ever known. He and sandy got along fairly well but sandy being as bookworm’s, didn’t spend much time with her brother. Jake’s frustration with girls and trying to get a date while surviving life itself seemed too much for him. But little did he know that his world was about to be completely changed; by his sisters.
The week had been slow going and fairly rough on Jake. He had asked out this girl he liked heather, and she said no. Actually she laughed at him. On top of that he didn’t think his mid-terms had gone well. All in all he was really looking forward to the long weekend. Jake woke slowly and tottered down the stairs into kitchen. Jessica and Sarah were already up and dressed for the day. Jessica was standing at the stove stirring a pan of scrambled eggs. Sarah was sitting at the table with a sketch pad and a plate of eggs and bacon that looked untouched as she scribbled in her doodle book. Sarah glanced up and dropped her pencil. “holy hell, what happened to your hair? Stick your dick in the light socket again?” she hazed. Jake grumbled but said nothing, he just sat down at the table and yawned. Sarah coughed and pretended to gag. “urgh, brush your teeth.”
Jake smiled. “why?” he got up and moved over to her. Jake leaned over Sarah’s chair and blew his breath right in her face.
Sarah groaned and shoved him off of her. “you little worm get away from me.” she cried.
“both of you knock it off.” Jessica said. She set a plate of eggs on the table. “eat Jake.” she said.
“ok boss.” Jake mocked and sat down.
“what are you doing tomorrow?” Jessica asked as she sat down next to him.
Jake shook his head. “nothing why?”
Sarah laughed and grinned at him. “well it’s your birthday dumbass.”
“you forgot your own birthday?” Jessica asked amazed.
Jake shrugged. “I guess. I had a bad week.”
“you are a idiot.” Sarah laughed.
“bitch.” Jake muttered.
Sarah stood up so fast she shook the table. “hey! I didn’t forget my birthday. Don’t call me a bitch you little spaz.”
Jake stood up fast enough to send his chair tumbling backward into the counter. Sarah froze in brief fear as she had a flashback to when her old boyfriend used to hit her for not putting out. Jake didn’t hit her of course, he did turned away and ran up the stairs. Lindsey was coming out of her bedroom as Jake stormed into his room. Lindsey frowned and went to the stair to hear Jessica scolding Sarah about going to far, and Sarah sounding genuinely amazed, think she hadn’t even gone that far. Lindsey turned back to Jake’s room and knocked on the door. “Jake? Can I come in?” she asked, softly. When Jake didn’t reply she slowly opened the door. Jake sat on the end of his bed banging on his guitar, his eyes were red not like he had been crying but not more like he was trying not to.
“so what did Sarah say this time?” Lindsey asked.
Jake didn’t reply.
“come on Jake talk to me. I’m your sister I want to help.” Lindsey pleaded.
Again Jake was silent. Lindsey was always trying to help him, but this was something she couldn’t help him with.
“ok, well if you want to talk. I’ll be home all day.” Lindsey started toward the door.
“am I ugly?” Jake asked suddenly.
Lindsey turned back to him. “are you serious? Jake absolutely not, why would you even ask that?”
“I asked heather out.” Jake said.
“is that the girl you’ve been talking about?”
Jake nodded. “yeah, she said that she only dated hot guys.”
“so why’d she say no to you?”
Jake shrugged. “guess I’m not considered ‘hot’.” Lindsey sat on the end of the bed next to him. “Jake you are a good looking, no, a great looking guy. Look at you, I mean, you’re trim, strong and you haven’t had a zit on you since ninth grade. Girls should be lining up for you.”
“yeah, right. I’ve never gotten a single date in my life. I’m pathetic and worthless and,”
“hey, stop that right now.” Lindsey spat. “you’re going to find someone. Tell you what, how about you and I go out and I’ll help you get a girl? I can be like your dating coach.”
Jake chuckled. “you’d do that?”
“why not? You’re my brother and I want to help you not piss you off like Sarah. I’ll get you a date if I have to do it myself. Or you know what I mean.” Lindsey said. “now I’m going to go have a little talk with your best friend downstairs.” she went to the door.
“Lindsey?” Jake said.
“yeah?”
“thanks.”
She smiled. “don’t mention it.”
After she left Jake felt much better. He played guitar for a little longer than found he had to relieve stress a different way. He pulled out one of his playboys and lay back on his bed. He worked himself into a glorious hard-on and was stroking fairly casually in no hurry to finish. Suddenly the door opened and Jessica literally trotted into the room.
“hey Jake come on, were going to…” they both froze for a few seconds. Jessica eyed the boner her brother had a grip on. She was taken aback by his size. He had to be at least eight maybe even nine inches long, and thick too. Then the world caught up to both of them. Jessica spun toward the door and darted into the hallway. “oh, god Jake I’m so sorry!” she cried pulling the door shut behind her.
“Jesus Christ Jessica ever hear of knocking?” Jake screamed tucking himself back into his pants.
“I said sorry.” Jessica cried from behind the door.
“what did hell did you want anyway?” Jake asked.
“oh, umm.” Jessica actually had to think. Her brother’s cock was still fresh in her mind. “Lindsey said it would be good for you if we all went out to the beach. So I came to tell you to get your bathing suit on.”
“alright, I’m coming. Shit I can’t get a frickin’ break.” Jake spat moving to his dresser and digging for his trunks. All the girls were sitting in the living room in their beach attire, which turned out to be two piece suits and very large t-shirts. Jake only wore his blue trunks and sandals, his towel draped over his shoulders.
“you guys ready?” he asked.
They stood up and picked up their towels and headed for the car. Sandy was reading a book of course and didn’t bother to put it down to go to the car. The book was the lion’s game by nelson demille and Jake had read it before so he knew it to be a very hard book to put down. Jessica kicked a large ice chest. “can you put this in the trunk for me?” she asked. Jake bent down and lifted the chest with a loud groan. “what did you put in here rocks?”
“oh come on, you have muscles so use them.” Jessica said shutting the front door behind them and locking it.
“don’t break yourself twiggy!” Sarah called laughing from the backseat, then she squealed when Lindsey pinched her.
“bite me a-cup.” Jake called back. Sarah was far from and a-cup but she wore push up bras so much that he knew being called flat would piss her off. Jake dropped the ice chest into the trunks with a heavy thump.
“don’t smash my tuna sandwich.” sandy called not looking up.
Jake climbed in the shotgun seat and Jessica drove off.
It was high noon when they got to the beach. The girls began to set up towels and beach chairs while Jake fought the ice chest down to the spot on the sand they hand chosen. One their little area was set up sandy and Jessica sat in a pair of beach chairs next to each other and began talking. Sandy had set her book down at her feet to talk to Jessica. Lindsey pulled her t-shirt over her head and tossed it down at Jessica’s feet. Jake, who was kneeling next to the ice chest catching his breath, took in the sight of his beautiful sister in her little bikini. Her body was nothing short of stunning, she had firm pert breasts that were probably a small c-cup. Her stomach was toned and firm and her ass looked like she could break walnuts between the cheeks. And her face well, her face was extraordinary with soft features and light brown eyes starring right at him.
Jake jumped and realized she was watching him ogle over her body. She’s your sister dumbass! His mind screamed at him. Lindsey just smiled at him and turned toward the water. “I’m going for a swim.” she said and ran toward the water in long graceful strides. Jake glanced at Jessica and sandy to see if they had noticed him staring at his sister as well, but they were deeply engaged in their own conversation. He turned around looking for Sarah, but she had found herself a volleyball game a few yards down the beach with some guy that were only too eager to let her play. Jake actually watched for a while as Sarah went for some jump shots or whatever they call it in volleyball. He noticed her breasts bounced delightfully, since they were about the size of grapefruits they had good reason to. Once again he had to shake evil thoughts from his mind. How come all the good looking girls he knew had to be related to him?
“are you just going to sit there?” Jessica asked.
Jake jumped and spun toward her. “what?”
“don’t just sit there go for a swim or go meet girls.” Jessica said.
Jake stood. “meet girls? Yeah, I wish.” nevertheless, he turned and walked slowly toward the water.
Jessica watched him go and waited until he was out of earshot before turning to sandy.
“you’ll never believe what I saw.” she said.
“what?” sandy asked eagerly turning in her seat to face Jessica.
“I walked in on Jake jerking off this morning.”
Sandy groaned and rolled back. “oh, Jessica I don’t need to hear that.”
“yes you do. I saw his penis right? Get this, our brother has an eight maybe even nine inch beast in his pants.” Jessica said, smiling.
Sandy’s eyes went wide. “you’re kidding?”
Jessica shook her head. “nope. And you know we can’t let our brother be miserable and alone when he’s got that kind of pleasure stick in his pants. We got to get him a girl.”
“I can’t believe he has a cock like that? I wish James had a cock like that.” James was Sandy’s current boyfriend. “I find it hard to believe girls aren’t banging down his door to get a piece of that. Then again he has almost zero confidence.” sandy said.
“right, we got to build his confidence around women.” Jessica said.
“how?”
Jessica shrugged. “I don’t know yet, but I’m willing to do almost anything. Sisters have to watch out for their brother you know.” Sandy nodded. “yeah he’s a turd sometimes but you do have to love him. Hey remember when he was twelve and walked in on me in the shower?”
“yeah, mom was out of town and I ended up having to tell him about the birds and bees.” Jessica laughed.
“he walked around with his hands in his pockets and wouldn’t look at us for a week.” sandy laughed. Jessica began to think. Lindsey was talking to a cute young blonde waist deep in the water. The tide swelled around them and Jake started toward them. Lindsey saw him and smiled. “well speak of the devil. Jake this is Britney.”
Britney smiled at him. “hi.”
“nice to meet you. Lindsey what are you doing?” Jake asked.
“she plays guitar too.” Lindsey grinned.
Jake’s eyes widened a bit and he smiled. “really what kind of stuff do you play?”
“rock mostly.” she said.
“cool, I,”
Britney turned toward the beach at the sound of her name. She turned back to Jake. “sorry I got to go. It was nice meeting you.” she turned and swam to the beach. Jake sighed and watched her go. Lindsey clapped a hand on his shoulder. “well that wasn’t bad, but we need to work on you a little more.”
Suddenly the tide surged and a larger overhead wave crash on both of them knocking them down. Jake and Lindsey clung to each other as they had once been told in swim class to prevent either of them getting sucked away in the tide. They tumbled together until they finally came to rest at the shore. Jake landed hard on his back and Lindsey landed right on top of him. They looked like a scene from “from here to eternity”. Jake was looking up at Lindsey. Water beaded off her soft skin and her breasts were pressed firmly against his chest. Jake immediately stiffened under her. Lindsey felt him tense underneath her and she smiled. “why are you so tense?” Jake took a deep breath. “get off me please.” he said his voice shaking.
“why?” Lindsey asked.
Jake closed his eyes. “please just get up.”
Lindsey shrugged and got up. She helped Jake stand and clapped him on the back. “let’s go get some lunch.” she said. They got home about a quarter to five and Sarah suggested ordering Chinese food, to which everyone agreed and gave her an order. Jake went to his room to change and wait for dinner. He pull out a pair of jeans and started to slip out of his swim trunks.
“Jake?” Jessica knocked on his door.
Jake slipped his trunks back up and opened the door. Jessica stood in the hallway in her tiny two piece suit. Jake felt his eyes roam her body despite himself. She did have the biggest breasts of all his sisters and they looked delightful in the small piece of fabric.
“can I talk to you?” she asked.
Jake’s gazed snapped up. “uh, yeah sure.” he stepped back from the door and let Jessica in. She came into the room and shut the door behind her, locking it.
“what are you doing?” Jake asked, his pulse in his throat.
“I want to help you. Jake, I know how frustrating it can be for a guy your age to get a girl. But I think I can help.” Jessica said.
Jake swallowed. “what?”
“I have a theory. That is, that if you were to see a naked women in the flesh and in person it will take away some of the shock and awe value and make you less nervous talking to girl, because hell you’ve seen it before. You follow?” Jake snorted and turned back toward the dresser. “yeah, and we’re we going to find me a naked chick? A strip club?”
“no,” Jessica said. “me.”
Before Jake could blink he felt the top of her bikini hot him in the back and slide to the floor. Jake felt tense instantly, knowing his sister was standing topless behind him caused all his muscles to lock.
“look at me Jake.” she said, stepping closer to him.
“no, Jessica. You’re my sister it’s illegal and so wrong.” Jake said.
“Jake it’s ok. I want you to see me. Besides it’s only fair. I saw you this morning so think of this as payback.” Jessica stepped even closer and put a hand on his shoulder.
“yeah, but that was an accident.” Jake protested.
Jessica tightened her grip on his shoulder and spun him around. Jake’s eyes instantly found his sisters large but perfectly pert breasts staring right back at them. Her nipple were small but hard, and he felt the blood rush to his dick so fast he thought he’d faint. Jessica saw the life grow in his pants too and she smiled. Jake blushed and put a hand over his stirring member.
“don’t be embarrassed. It’s perfect normal for that to happen when staring at a girl.” Jessica said. She moved closer and gently took Jake’s hand away from the front of his shorts.
“Jessica I…”
“shh. You don’t need to say anything. Just know that I love you and I want you to be happy.” she said. She held his hand and slowly pulled it toward her body.
“dinner!” Sarah cried from downstairs.
Jessica actually jumped as if she’d been bitten. She dropped Jake’s hand and bent down to put her top back on.
“we’d better go eat.” Jessica said tying her top back into place. “we’ll have to catch up later.”
When she was gone Jake stared at the door in disbelief. The reality of what he had just seen hit him like a cold bucket of water. He just saw Jessica’s tits naked and even more so almost had gotten to touch them. The boner in his shorts throbbed as if in acknowledgement that it also had seen everything. Jake shook his head and changed into a pair of jeans and a t-shirt that said “how do you like your pussy?” then had a bunch of pictures of cats with things like; dry, wet, pink, shaved, hairy, dirty, etc.
Before going downstairs Jake went into the bathroom to splash cold water on his face. He closed his eyes and thought about music and fat chicks dancing to get the pictures of his sister out of his head.
Finally satisfied he went downstairs. The girls were already gathered around the dinner table picking at their Chinese dishes. Jake’s order sat on a plate still in its box at his place at the table. He sat down trying to ignore all the girl talk. At dinner they usually ignored him as they spoke to each other about a dress they saw during the day or in tonight’s case guys they saw at the beach. Jake worked on focusing on his shrimp lo-mein but couldn’t help watching Jessica. She had put on a tight white top and took off her suit. He could see her nipples poking through the fabric and he wondered if she had done that on purpose for him or if she just hadn’t thought about it.
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