Sugar Brother

w0ndergirl4

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Tess was ready for her life of fame and fortune to begin, unfortunately she wasn't famous or wealthy. She had spent years learning from her role models, Kim Kardashian and Paris Hilton, but things just weren't working out the way she wanted. She knew fashion inside and out, she was popular, and of course, she was beautiful. But, if she ever wanted to be somebody, anybody, she needed to be able to go to the right parties and the right restaurants and she needed to be able to buy the right clothes and handbags...the right shoes, for god's sake! She'd considered trying to find an older man who had money, but if there was one thing she'd learned from Kim and Paris, you couldn't trust men not to record you having sex and then sell the tape to someone. And unfortunately, most of the rich men she had met weren't willing to give up much if she wasn't willing to put out. Why couldn't her parents be rich?

Glancing up from the fashion magazine she was reading, Tess saw her not rich parents sitting at the patio table by the back door. Jesus, dad, not the blue jean shorts again! And mom, seriously, it's time to get a new hair cut. Just because your old doesn't mean you have to give up completely. They really were clueless she thought as she brushed her long blond hair back over her shoulder and turned her attention back to her magazine.

"So what do you know about this new job?" she heard her mother's voice drifting across the short distance to the deck chair that Tess was reclined in.

"He's going to be the vice president of sales," Tess' dad answered as he reached for his glass of lemonade. "It's quite a jump for him and with the increased stock options it could mean serious money."

Serious money?
Hearing those two words, Tess suddenly became interested in her parents' conversation. She sat up a little straighter and absently adjusted the front of her tiny green bikini top.

"I'm so proud of him. He's been working so hard, he deserves it," mom said, clapping her hands together gleefully.

Tess rolled her eyes. They were always proud of David. He could knock up a twelve year old crack whore while driving drunk in a stolen car and they would still be proud of him. Of course, if David really was getting a big promotion, and more money, he might just be the answer to Tess' problems. She desperately needed a pair of new heels to go with the new dress she'd bought, the only problem was the shoes were $400. And the handbag that went with the shoes was $600. But what was $1000 to a vice president of sales for a blossoming software company on the rise.

Of course, there was the fact that David had always considered Tess a spoiled little brat. Guess I'll have to turn on the charm when he gets here for dinner, the teenager thought, smiling to herself.

Kate-Upton-nude-1.jpg
 
David was just a few blocks away from his childhood home, where he grew up with both of his parents and his younger sister Tess, who was about nine years younger than him. He was driving the Toyota Camry he had had since his second year of college, he had leased it brand new then, but the old girl was starting to show her age. He had to bring it in for more repairs recently, and now with his new promotion he was meaning to upgrade to a Lexus, but thinking about giving up the Camry unconsciously brought pangs of guilt to his psyche.

David had gotten to wear he was by hard work. He was diagnosed with a learning disability when he was thirteen years old. Prior to that he had thought himself stupid, but by learning to learn his way, he conquered his disability during high school. What that meant was sacrificing a healthy social life for extended hours hitting the books. He had only had sex with one girl in high school, and it was over the course of a summer where he volunteered with the girl at a non-profit so David could pad his resume. Once David had gotten into college, his social life didn't improve much, but his abilities in the class room did. He graduated from college magna cum laude with a double major in Economics and Accounting, as well as minoring in Public Speaking, something that scared him to death at first, but paid off when he got his job at Norcom. He was put into a commissions sales job that was tough and didn't provide room for much advancement, but it was a tough job market. His trained sales tongue and understanding of figures and efficiency got him just enough money to pay for night school where he obtained an MBA, which allowed him to move up. In addition, his smarts and his work ethic got him to where he was today. Now he was going to be wealthy for someone his age with as limited experience that he has, and he didn't have the social life to enjoy his new position and riches.

The Camry squeaked its breaks as David parked in front of his parents' house. He saw his sister's car parked in front of him. David knew his sister didn't have a job, but it looked like her car had been freshly detailed.

"Gee, wonder who paid for that," David said to himself. His sister, Tess, lived in the clouds. She wanted to be famous, and to be famous she would be rich, and to get rich, Tess would be famous. It was a completely circular go-nowhere plan a spoiled teenage girl would come up with. David thought about all of his hard work and how good it felt to get the new promotion. Then he thought of Tess and shook his head. They were the same flesh and blood, the same genes. How was he the way he was, yet Tess was a miserable embodiment of greed.

David knocked on the front door as he opened it, just to announce his presence. "Hello," David shouted, "where is everybody?"
 

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Tess recognized the familiar sound of her brother's squeaking brakes as he pulled up in front of the house. "David's here," she announced, dropping her magazine and bouncing up off her chair. "I'll go let him know where we are," she volunteered, brushing past the table where her parents were sitting and into the house, ignoring the surprised looks on their faces. God, you'd think she never did anything nice the way they looked at her.

"Hello," David shouted, "where is everybody?"

"Hey, big brother," Tess answered as she stepped into the living room, adjusting the top of her bikini again before giving him am enthusiastic hug. "It's good to see you." She lingered in the hug for a moment, hoping that she wasn't laying it on too thick. "Mom and dad are out back on the patio."

"Oh and congrats on the promotion," she added as she took turned and started toward the back door, glancing over her shoulder to make sure that David was following. "Please tell me you're going to get a new car now?"
 
David was a bit surprised when he saw his sister had troubled herself to come greet him at the door. He even more taken aback when she hugged him. He couldn't remember the last time they had hugged, and he was sure it was never that close. David felt some discomfort as his sister held him close, smashing her big breasts against his torso. Unconsciously, he began to think about Tess's breasts and whether they were real or not, given their size. And then David caught himself, and internally made the thoughts stop.

The whole situation was weird to the man, and it was made even more bizarre when Tess actually congratulated him on the promotion. He couldn't believe Tess knew anything that was going on in his life, and he couldn't believe she was actually happy for him. Her statement didn't seem sarcastic, but it also didn't seem totally altruistic to David. It had a hint of something else behind her words. Then she asked about a new car. That was it, David thought. Tess had been such glamour whore that just being associated with wealth and luxury would feed into her delusions.

David followed Tess to the backyard and lied, "Haven't really thought about a new car."

David's parents heard him as he followed his sister to the backyard. His dad whipped his head around to see David and expressed surprise at his statement, "No new car? Son, you've been driving that old Toyota for years, don't you think it's time to treat yourself? Haven't you always wanted a Lexus?"

David didn't want to hear that. Normally it wouldn't bother him. He, in fact, had told his father on a few occasions that he would like to own a Lexus one day, but he felt uncomfortable when Tess asked him, and especially now that Tss was in ear shot of a luxury car conversation.

David replied, "Well, right now I'd just rather focus on other things. A car may come later."

His mother nodded and released some sounds of approval, "Exactly. David has worked so hard and long hours at the price of a life outside of work. Now he can relax, take it easy at work, and finally work on getting us a daughter-in-law and some grandchildren."

This embarrassed David. He was never a ladies man, and had hoped that his mother was right. However, his id was hoping David would sew some wild oats now and find some sexual partners a few levels up from the 4s, 5s, and 6s he had been with in high school and college.

"Oh, we can talk about it more over dinner," his mother said, "Al, would you mind helping me out in the kitchen?" This got David's father out of his seat as he followed his wife into the kitchen.

"Need any help?" David asked hopefully.

"No," his mother answered, "you stay here and catch up with your sister."
 
As their parents disappeared back into the house to finish preparing dinner, Tess took a seat at the patio table, "Come on sit down and talk to me, I've been bored for the last two hours with no one to talk to except mom and dad. Have you thought about what kind of car you want to get?"

Tess was doing her best to sound interested and friendly while remaining casual as she leaned forward and placed her elbows on the table, her chin resting on her hands, "I'd be glad to go car shopping with you this weekend, if you want my help. Maybe we could go Saturday afternoon."

"Of course I did get invited to a party on Saturday afternoon, downtown. It's a fashion show actually, lots of designers, agents, models. It would be a great chance for me to meet some people, but..." Tess paused for a moment, looking up at David before she continued, "I just don't have the right dress or shoes and I can't afford...sorry, enough about me. Tell me more about your promotion."

And all that money you have now...
 
David listened to his sister prattle on about her woe and misfortune as a result of not being spoiled enough, and had twice brought up a new car. Subtlety was not her strong suit. David knew that she thought if she bookended spending money on her with a treat for David, he may be feeling generous with his money, but he didn't. He pursed mouth was getting close to turning into a snarl. He just sat looking at her with her sun streaked blonde hair, her tan skin, her large breasts straining against her bikini...

A light bulb went on over David's head. She would be perfect, he thought. And she already offered to go, he continued running his inner monologue. The realization David had reached was that his sister may be the perfect companion to go car shopping, if she dressed sexily enough, showing off her only valuable assets, David could easily get the upper hand on the salesman. David had proven himself to be an adept salesman, so he knew everything a car salesman would throw at him, and he also knew they were weak.

He looked into his sister's blue eyes and smiled, "Well, Tess. I've been put in charge of sales, and that's pretty much all there is to it. And as for a car, I was thinking a big luxury sedan, with leather heated seats, a sleek paint job, and $50,000 plus price tag." David knew throwing out the word luxury and everything associated with it was porn for his sister. "And I would love it if you came car shopping with me tomorrow afternoon. Who knows what other shopping may get done tomorrow?"

David let that last question linger. He had no intention of buying anything for his sister, let alone some overpriced "high fashion" items. It would be that much sweeter for him to get the lowest price on the new Lexus and then send his spoiled bimbo of sister spiraling back to Earth.
 
Dinner came and went and all the while Tess continued to beam happily at her brother and do her best to show interest in whatever topics he chose to speak on, laughing at his jokes, touching his hand or shoulder whenever possible. Anything to play the loving sister. It was second nature to her, charming people. She could turn it on whenever she chose and she was definitely pulling out all the stops for her brother, all the while planning how she would use the car shopping adventure the next day to get what she wanted. Not that tomorrow was the end all of the game. It was just the first act. You had to be willing to play a longer game, when appropriate, and Tess could be patient, when it was necessary.

The need for patience was foremost in her mind the next morning as she waited for David to pick her up so that they could go shopping. She had showered and spent over an hour getting ready. Her makeup was perfect, her hair was perfect. Wearing a pair of designer jeans, the cutest little belt from a boutique shop and three inch heels, she'd finished her outfit off with a simple, low-cut top that showed off her impressive bust.

Now all she needed was her rich, and hopefully generous brother to show up.
 
David arrived outside of his parents' home fifteen minutes later than he told Tess. He wanted to make her sweat, wanted her to worry that she had been shorted by her brother. When David pulled up to the curb, he sent a text to her that merely said, "Outside."

While David waited in the car for his sister he had thought how maybe this wasn't the best ides; exploiting his sister's body for his own gain. He had thought that even though she had been a spoiled bitch for most of his adult life, everyone still deserved some semblance of respect. The thoughts were turning in David's head. He had always been the good guy, for better or for worse. He had always kept his head down, nose clean, helping when asked, and always waited for an appropriate time to take advantage of an opportunity. Now he was on the verge of taking something for himself, selfishly. It wasn't him...but his parents had said now was the time to start treating himself. Using Tess as the bait to get his new car would be a treat indeed.
 
"Alright Tess, time to go reel in the big fish," the teenager said to herself as she read her brother's text. Plastering a smile on her face she stepped outside and made her way to David's car.

"Hey, how's it going?" Tess greeted her brother as she slid into the seat next to him. "Ready to go find yourself a fancy new car?" She leaned over and patted David on the knee before reaching for her seatbelt, which stretched between her large, round breasts.
 
David said, "Sure thing." He looked over at Tess buckle in and couldn't help but notice the strap get mothered between her two soft fleshy mounds on her chest. He thought to himself, they must be real. The his mind started to wander about what they would look like uncovered. He quickly snapped himself away from that train of thought and felt disgusted with himself. He reiterated in his mind over and over again how she was there to fool some other sucker, not him. Especially not him, Tess was his sister for Christ's sake, his own flesh and blood. He shifted his eyes to the road and pulled away from the curb.

The ride to the Lexus dealership was a strange one for David. It took about twnety five minutes, and he made idle, pointless, and dull chat wit his sister along the way. But every few minutes his mind would drift back to the forbidden zone. He would catch a glimpse of his sister's cleavage, or her soft thighs and he would start to wonder. He especially wondered if she had tan lines, and then he thought of his sister sun bathing nude. He kept trying to steer his thoughts away from such perverse images, but he knew something lurked deep in his mind, or even his soul that was dark and evil, and wanted that soft, tan forbidden flesh clinging to his bimbo of a sister.

When they arrived at the Lexus dealership, David parked and got out of the car. Opening the door for his sister. As soon as the salesmen walking the lot on the nice sunny day got a view of Tess, David saw a few of them start to make there way over, but middle aged balding man with glasses got there first. He approached David, extended his and to be shook, and said, "Hi, my name is Marvin, who do I have the pleasure of meeting, and what can I do to make your dream come true today?"

David shook his hand and in his own mind shook his head. This guy was so pathetically alpha male, David thought, Tess would for sure be able to throw him off of his game. "Well, Marvin," David said, "I'm looking for the Lexus, a lot like the Camry here. Oh, by the way, this is my sister Tess." David pointed out his buxom sister, "and she's been telling me that these cars are way overpriced."

Marvin caught no wind of David's last coment, or at least ignored it and immediately went to shake Tess's hand.
 
Tess was excited as she and her brother pulled into the Lexus dealership. This was definitely her type of place, she thought as she glanced around at all the shiny, extremely expensive cars. The ride to the dealership had gone well, the teen and her older brother had talked the whole way, and Tess had done her best to appear interested in whatever topic he had brought up, despite the occasional strange looks he had given her.

As David greeted the salesman who intercepted them, Tess was busy trying to decide whether a Lexus was actually good enough. Maybe she should try to talk her brother into an Escalade or a Hummer, she thought. Before she could make up her mind, David was introducing her to the salesman, Marvin.

"Hello," Tess said, flashing the older man her best smile and reaching out to shake his hand, her chest bouncing slightly as she did.

Tess was content to let David do the talking as they began to stroll across the lot, led by Marvin the salesman, though she couldn't help but notice that Marvin the salesman was directing most of his comments, and all of his attention, to her. Considering what they were there for, she decided that a little flirting might be the best way to help out. She was happy to oblige, especially if it meant that her brother might be willing to take her shopping afterwards.

And so, Tess did what Tess was best at. She giggled at Marvin's lame jokes. She smiled at him constantly, brushed her hand against his arm, even bent over in front of him, first with her back to him, then later while facing him. Okay, she thought as she caught Marvin staring at her tits for the millionth time, this better get you a good deal, and get me designer shoes and a handbag.
 
David had walked through the lot with Marvin and Tess looking at all of the different makes and models of the luxury brand. He had really been impressed with the way Tess had been working Marvin. She really seemed to get what David had wanted her to do, and he appreciated that. She had played the part so well, even though David thought a gold digging cock tease was probably the part Tess had been born to play.

After a while of Tess teasing the old car salesman, quite shamelessly at some points, David thought it was time to buy his new car. He told Tess to just keep herself busy while David went to talk to Marvin. In the negotiation room, Marvin seemed ambushed and caught off guard. David saved about $25,000 on his new car by way of getting way more for his trade in than it was worth. Tess had paid off swimmingly, knowing exactly what David wanted her to do, maybe he would take her shopping as a reward, after all he saved the money largely due to her work...then the thought hit him. He would possibly bring it up later, for now he had his brand new shiny car.

David signed the final papers and walked back out to the lot to his sister. He held up the keys and said, "Want to go for a ride?"
 
While David and Marvin hashed out the details of the car deal, Tess sat in the lobby texting a few of her friends, updating her Facebook status and shopping online. Her work was done. She'd done her absolute best in flirting with and distracting the older man, she decided. The rest is up to you bro, she thought as she crossed her legs.

Eventually David emerged from the small office, a smile on his face and a new set of keys in his hands, "Want to go for a ride?"

"Hells yes!" the blond answered as she stood and slipped her phone back into her purse. "Did you get a good deal? You better have after the way I got old Marvin all worked up for you."

"He couldn't keep his old pervert eyes off the merchandise," Tess added as she led her brother out of the dealership and over to where his new Lexus was waiting.
 
As they walked to the new car, David listened to his sister and suddenly stopped in his tracks. Something she had said made him pause. When David heard her say, "the way I got old Marvin all worked up for you," his suspicions seemed to have been confirmed. His sister was in on it the entire time, but it hadn't been planned out. They worked as a perfect team, a regular couple of grifters. David couldn't believe it, even though he had suspected it. He thought he was just manipulating his dumb sister into doing something for another person for a change, but in fact she had been in on it the entire time.

The new Lexus owner unlocked the doors with his remote and they got into the car, when David finally decided to get moving again and said, "Yeah, it was pretty good deal."

Still shocked by his sister's awareness, David began to let his mind wander. If she had been in on the Marvin angle, was she playing David? David thought maybe the generosity he was feeling while he signed the documents had been the plan by his sister all along, that she was expecting David to buy her something expensive and flashy now. Well he wouldn't be played, David decided. He wasn't going to bring up the shopping, he would just wait for his sister to show her hand.

He turned the engine over and pulled out of the dealership. The mall wasn't very far away, but it was in the opposite direction from his parents' house. Instead of getting on the route to the shopping center, David took the direction to drop Tess off at her house, and to see what move she would make next.
 
Where the fuck is he going? Tess asked herself, trying not to let the irritation she was feeling show on her face. The mall is in the other direction...my shoes and handbag are in the other direction! She had just saved her brother, well, probably thousands of dollars on his new car and he was just going to drive her home and drop her off? But what could she do? If she said anything her plans to string David along for months and get untold gifts from him would be ruined...

Tess knew she needed to be patient.

"I absolutely love this car" she said as she ran her hands over the seat, and the dashboard. "I think you made a great choice."

"So, where to now?" she asked, trying to sound nonchalant. "Maybe we could stop and get something to eat. Are you hungry?"
 
David watched his sister caress his car and became puzzled. What was she doing, he thought to himself. David couldn't help but jump to the conclusion that he was her new Marvin, just another mark in her con game.

He stopped at a red light when she asked if him if he wanted to get something to eat. This has to be another angle, his brain kept telling him. She had never been so considerate and congenial in he entire life, especially towards David. He always thought she hated him, and just last week they had gone a whole family dinner without any words between each other.

David kept thinking as he went on the green light. He drove the car through the intersection and pulled over against a curb. David put the car in park and looked over at his sister, beautiful but selfish. He was going to challenge her, not give in to her black widow nature.

"Look," David started, "I really appreciate the ... help with the car, but I have to level with you, Tess. I'm not going to take you shopping and buy a bunch of expensive stuff nobody needs."
 
"Why not?" Tess asked, leaning toward David, frustration and disappointment finally evident in her voice. "I mean, you have plenty of money now and I'm your sister. Why can't you just help me out a little?"

Fuck! This isn't going the way it's supposed to go, she thought to herself as she clutched at her brother's arm, desperate to convince him to buy her the shoes and handbag she needed.

"I'll do whatever you want, David," Tess added as she studied his handsome face, trying to figure out of she had any chance at all of convincing him to give her the money. "I'll wash your car, clean your apartment...I'd even go out with one of your loser friends if you want me to..."

"Pleeeeeeeaaaassssseee, David..."
 
David had finally got what he wanted. He had crushed his sister's dream and had revealed her true selfish nature. He should have been reveling in the pleading and begging, but it didn't sit well with him. She had gone from sly con woman to a girl throwing a hissy fit. She even offered to date one of his friends. Is she serious, David found himself saying in his mind, he would never give one of his friends a shot with his sister. Not only were most of his friends little more than douche bags he worked with, Tess was, frankly, too hot for any of them.

David found himself lingering on that last point as his sister clutched his arms with her smooth tan arms. Her breasts bounced as she begged. He couldn't help but picture her begging for something else, but he tried to eschew the thought. However, his male instincts fought with him and he started to wonder just how desperate she was for the money. No, he rationalized with himself, he couldn't do that. She was his sister for Christ's sake, that would just be wrong and disgusting. Then he looked at her breasts again while she begged.

The thought of paying his sister for sex was too outrageous for him to consider it for very long, that it was almost some hilarious bit of comedy. He would be outed as some weirdo pervert. His sister would tell everyone, that is of course if David wasn't willing to pay her blackmail, but...maybe she was so depraved and self-absorbed that she wouldn't hesitate to whore herself out to her own brother.

David decided he wouldn't even try, but if his sister was thinking the same thing...hell, she knew about Marvin.

"I don't know," David said slowly, hoping to see how far his sister would push things, how desperate she was for a pair of fucking shoes, "it's not like you need the stuff."
 
"But I really do need them, David, please you have to understand," Tess said seeing a glimmer of hope in her brother's eyes. "I don't just want them because they are expensive or because they look fantastic, I need them because if I want to make the right connections and make a good impression, I have to look the part. This party is my chance to meet some real designers, and real agents."

"You do think I'm pretty enough to be a model, don't you?" Tess tried not to go over the top with her pleading, but she couldn't help it. She had to convince him. As she waited to see what he would say, the teen leaned her head on her brother's shoulder.
 
David knew his sister was still trying to manipulate him, but he couldn't help melting a little as she pleaded for reassurance from him. Then the wheels in his head started to turn once again. He started to think that maybe if he would do this for her, she would become a famous model, or more likely she would finally get the reality check she so desperately needed. Either way, she would probably stop bothering him. And if the event she was talking about really existed, maybe there would be other girls like her there, pretty but so desperate and insecure David could start sewing some oats.

He turned to his sister, touching her chin with his thumb and index finger. "Of course, you're pretty enough to model, you're the most gorgeous girl I've ever seen," he said thinking he might be laying it on a little thick, "that's why I'll take to the mall, on one condition. You have to take me with you to this event tonight?"
 
Tess' face lit up as she heard David say that he would take her to the mall, "OMG, David, are you serious? You'll really take me to get the shoes...and the handbag? You are the best brother ever." Over come with excitement, the teenager squealed with delight and swung her arms around her brother's neck, planting several small kisses on his cheek and neck before finally sitting back into her seat.

"Are you sure that's all you want?" Tess asked, still flush with excitement. "You just want me to take you to the party with me?"
 
His blood started rushing to the lower part of his body as his sister got carried away kissing him on his neck and then the enticing way she asked if that was all that he wanted from her. He thought about pressing the issue with her, to see how far he could take her, but thought the better of it, or at least what society tells him is the better of it.

"No," he stammered a bit, "just going to the party is all I want." He started to sweat above his brow and gulp. The car was at perfectly temperate climate, but David definitely started to feel hot, and it started to show in his cheeks.

He turned the car around and headed to the mall, where his sister could add fuel to her fantasies coated in glitz and glamour.
 
Alexandre Birman Pony Hair Wedge Pumps, here I come, Tess thought to herself as she and David walked into the small designer shoe store. She'd been dying to get her hands on these shoes for a month and now it was going to happen. She already knew they would be perfect with the dress she had bought and she was sure that the Jimmy Choo clutch she'd seen on sale would complete the outfit. Of course the Jimmy Choo wasn't Gucci but it was in her price range or at least, in her brother's price range.

Grabbing David's hand, Tess pulled him to the back corner of the store and gleefully yanked the shoes off of the display. Clutching them to her chest she turned to her brother and bounced up and down, "Aren't they just amazing? I should probably try them on, just to make sure the fit is right," she said as she pulled him to the nearest chair and quickly removed her shoes. Carefully slipping her feet into the burgundy colored shoes, she stood, her face beaming with a smile. With the high heeled shoes on she was nearly as tall as David.

"They fit perfect," she announced as she began to turn in a circle, her head down, eyes glued to her feet. "What do you think? Do they look good on me?"
 
David looked at her feet and felt defeated. She looked stunning in the shoes, but he had fallen into the trap that pretty much every man who had crossed paths with his sister had. She had wrapped him around her finger, and now he was going to spend a small fortune on things of which he would get no use or utility. The worst part was it was his sister's charms that had reduced him to some pigeon mark. He felt pathetic and saw appeasement as his only way to get out of the tangled nest of iniquity he wove for himself. Once she had her clothes, and she was at that party, David thought he would finally be free from her clutch. At least he would probably be wrapped around another pretty young thing's finger, but that quid pro quo wouldn't be against the laws of nature.

"You look stunning," David said from a faraway sadness, "is there anything else you want?"
 
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