Sugar Brother

Tess was still so excited about the fact that she was actually going to be able to get the shoes and handbag that she'd been craving that she forgot for a moment that she didn't really like her brother and bounced into his arms giving him an excited hug, "You really think I look stunning? I knew these shoes would look great on me...and you haven't even seen my dress...maybe when you drop me off you can stick around while I try it on."

As Tess finally stepped back, she sat back down and began to remove the new shoes, "The only other thing I need is the clutch that will go with these shoes. Then we'll be set to go."

"Do you know what you're going to where to the party?" the teen asked as she stood up, having slipped her own shoes back on. Carrying her prized high heels, she started toward the front of the store so that they could pay for the shoes.
 
The question, much like everything else Tess had done that day, caught David off guard. He was never one for fashion, possibly one of the reasons he was never a very popular person. As his sister bombarded him with comments about her own shopping desires, David had drifted off, but the question brought him back to reality. If he wanted to take home an impressionable, insecure, aspiring model at the end of the night, he probably needed to look the part. If all the girls at the party were like Tess, there was no way he'd be able get into their pants in the $25 Dockers he was wearing.

His joy from earlier was starting to return, he found another use for his sister. She could turn him into some suavely dressed playboy that she and girls of her ilk would be interested in.

"You know, Tess," David said, "I have no idea. Would you be willing to stick around the mall for a little bit longer to help me shop?"
 
"Ah, big brother, you've come to the right person," Tess said as she picked up the bag from the counter that contained her new shoes. "Shopping is what I do. I shouldn't have any trouble making you look good." With that she grabbed David's hand and pulled him out of the shoe store and towards the store that had the handbag she needed.

"What kind of girl do you want to attract?" she asked as they walked. "You do want to go to the party so you can pick up a girl, right?"
 
"Well, yeah," he fumbled with his answer, "it's not like I'm into fashion, so... so the only reason I'd be going is to pick someone up."

His words came out clunky and unnatural. He had never acted like anything other than a rational decision make around his family, and here he was living somewhat out of the box, talking about women with his sister. He had always tried to keep personal desires and ambitions away from his family, and his friends for that matter, what little of those he had. And David had always thought such had been reciprocated. He didn't see his parents as individual humans, only as a unit that provided him with necessities. He definitely never saw Tess as anything more than a money vacuum, but now he was trying to be pulled into a conversation about women; sex was at the heart of the question. And much to David's discomfort, he had seen that his sister and sex probably go hand-in-hand.

"As for a type," David clumsily continued, "I don't really know."

Of course, he did know. He wanted some blonde and tan. Someone busty with a pretty face, hell he wanted someone like his sister, Tess. Peering into the darker part of himself, David had found out that day that his libido didn't just want someone like Tess, it had wanted Tess. He didn't want to admit it to himself, and definitely not to his sister.

"Just someone pretty, for a change," he said rather sheepishly.
 
"That shouldn't be a problem. I'm sure there will be a lot of beautiful girls there," Tess responded as they entered the small shop that sold the expensive handbags. "You've got a lot going for you already. You are good looking, you've got money. All you need is a little help with your style."

"And that's where I come in, right?" she said with a smile as she stepped over to a display near the front of the store and picked up the clutch she wanted. "I mean who knows more about style than your baby sister, right?"

Tess was excited about the prospect of turning her boring brother into a stud. She loved a good project, especially if it involved shopping. And besides, if things went well and David actually ended up picking a girl up at the party, who knows how generous he might feel toward the sister who helped make it happen. And Tess could certainly think of ways he could express his generosity toward her...clothes, jewelry, more shoes...a new car...

"Don't you worry brother, when I'm done with you, you will feel like a new man," she said as they walked to the counter.

Tess spent the next hour leading David to a series of clothing stores, showing him clothes, helping him try them on and ultimately helping him choose several new outfits, complete with new shoes and a new watch. By the time they were done, they both had their hands full of shopping bags and Tess was practically giddy.

"I need to get home so I'll have time to fix my hair and paint my nails," she announced as they crossed the parking lot toward David's new car. "The party starts at 7 so you'll need to pick me up no later than 6:30, okay?"
 
David had simply stepped aside and let his sister whirlwind her way through the mall and dictate the plans for the evening. He had dropped her off and went home to change and get himself ready for the party. He went into his bathroom and showered. He stepped out of the shower naked and looked at himself in the mirror. He was disgusted. He was disgusted by the amount of money he had spent earlier, he was disgusted by the way he just bent to Tess's will later on, and most of all he was disgusted by the thoughts he had had of Tess throughout the day. He looked away from the mirror when his naked manhood had started to swell at the thought of Tess again.

He turned the faucet below the mirror to cold and soaked his hand in the icy water, it put David back in control of his body. He then went about shaving and doing other bathroom routine things, which included the Neimann Marcus cologne his sister had suggested to him.

Once he had put on his new jacket and shoes he was out the door and into his Lexus. He drove back to his parents' house and arrived at 6:30 to pick up his hopefully delusional sister.
 
Tess smiled as she looked at her reflection in the floor length mirror. Her dress fit perfectly, showing off the curves of her body, and with the new shoes and handbag, the outfit was complete. Her hair was pulled up and back so that her face and neck were accentuated, and her makeup, while understated, was designed to draw attention to her eyes. She knew there was a lot riding on the party, but she also knew that she was ready.

Through her bedroom window she saw her brother pull up in front of the house. Making sure David met someone at the party was every bit as important to her as it was for her to be noticed by the right people, she just hoped he didn't screw anything up.

"Hey, sexy," Tess said as she slid into the car next to her brother. "Are you ready to have some fun?"
 
David couldn't help but smile when he saw how gorgeous his sister looked. He was proud that he shared the same DNA with someone who was outwardly beautiful, joy overcame him when he realized that other women at the party would look a lot like her, probably not as attractive as Tess...then the secret shame started to creep its way back into David's psyche.

"Of course," he mumbled, quietly from a distance.

The shame clouded his joy when he caught a glimpse of the perfect legs of his sister, and then the inviting yet all too forbidden valley of cleavage. David quickly pushed the cloud away, but it would linger in the back of his mind from his parents' street to when he handed the valet the keys to his Lexus.
 
Tess and David arrived at the downtown hotel where the party was being held at least forty minutes late, which was just as she had intended, realizing that no one important ever showed up for one of these events on time. She had already explained to David in the car that if either one of them was going to get what they wanted out of the experience they were going to have to make sure no one thought they were a couple, so the plan was once they made their entrance they would separate and mingle.

"Don't worry, big brother, I'll make sure I talk you up to a few of the girls and send them your way," Tess said as she gave David a wink and squeezed his arm before stepping away from him. "Just remember, these girls like money and power, don't be afraid to show them you have those things."

Turning her back on David, Tess moved toward the stage where the fashion show would take place later on during the festivities. She was giddy with excitement at the prospect of meeting some of the designers or even some of the famous photographers that she knew were supposed to attend. Meeting a designer might get her a runway show, and meeting a photographer might get her some new pictures for her portfolio, which could really help her career.

The tall blond spent the next hour doing what she did best, socializing. She laughed and gossiped and flirted and danced with all the right people and if she couldn't get close to one of those people she would laugh and gossip and flirt and dance with someone who was close to that person. She even managed to meet a couple of models that she thought would be perfect for David. Each time Tess would find a way to mention her handsome, successful brother who was just across the room, intimating that he was looking to get into the industry by investing, and of course, making it clear that he was single.

All in all, things were going well by the time she bumped into her brother at the bar, "So? Any luck with the girls I sent over?" she asked as she flipped her long blond hair back over one shoulder and surveyed the room.
 
David couldn't help but admire the elegant way his sister worked the room. The way she came off so flirty and bubbly, even though he knew she was pandering worse than a politician during an election year, but it didn't seem that anybody saw through her. Part of that had to be because she was flaunting her beauty in such a cavalier manner, that the straight men in the room couldn't focus. Nearly every woman there was gorgeous, but David secretly told himself that none of them held a candle to Tess's lithe body.

He had been grateful and more than receptive to the women Tess had encouraged meet him, and he was definitely interested in both of them, not for any long term relationship, but certainly for a physical fling. He had never thought of himself as love them then leave them type of guy, but his id was starting to crawl out of whatever deep part of his mind it had slept for over two decades. David was ready to sew his oats. His ambition was great even though he was unassuming, it was what got him to where he is in his professional life, now it was working with his libido. Although his male instincts had appreciated the models Tess had scrounged up for him, there was nothing his body wanted more than his sister.

When Tess approached him, David smiled.

"Yes, I got both of their numbers," David said proudly, "thanks. I may meet up with one of them later, unless you'll be needing me...for like a ride, or something like that, later."

David gulped his scotch down.

"So," he transitioned, "how's your luck been?"
 
"I don't need luck, big brother," Tess responded with a wink. "I was born to do this." And of course, Tess was very much in her element at the fashion party. These were her people. She didn't bother to mention that while she had met a very talented photographer who had seemed smitten with her, he still wanted almost $2000 dollars to shoot a new set of photos for her book. She knew David wouldn't understand. Most girls would have paid five times that much to have a studio session with Clark Gibbons. The fact that he was willing to do them for Tess for such a nominal fee meant that he thought she had real potential.

The question was, how was she going to convince her brother to loan her the two thousand dollars. If she could manage to get him laid, she might have a chance, but short of that, she wasn't sure what she could do. At this point, I'll suck his cock myself if I have to, Tess thought to herself as she smiled at David.

"Well, I'm going to go mingle for a few minutes before the runway show starts," the blonde explained. "After it's over, I'll meet you back here, okay?"
 
David hung around the bar for most of the party, trying not too appear too bored. He had hoped one of the other girls he had talked to earlier would have wanted to hang out with him, and try to squeeze money out of him like his own sister. If that would have happened, the young man could have worked out a little of the sexual frustration that had been building in him throughout the day. But they were like his sister, and were enraptured by the glamour of the runway show.

David could not have care less for what was going down the runway. It was a bunch of beautiful women wearing goofy things, no one in civil society would wear any of the ensemble displayed on the runway that night. David had ordered a few more drinks during the show and was starting to get a little light headed.

When the show had ended, David had drank six single malt scotches, and was feeling it.
 
Tess watched the runway show intently, loving every moment of it. Through the while show she chatted with the young man next to her, a personal assistant to one of the designers. He gave her his card and told her to give him a call sometime so they could get lunch. Tess slipped it into her clutch, hoping lunch might turn into an introduction to his boss, which might turn into a job.

Once the show was over, Tess spent a few minutes talking with some of the models trying to get information on upcoming opportunities, then eventually found her way back to the bar where David was waiting. As she slipped up next to him and put her arm around his neck, the blonde gave her brother a kiss on the cheek, "Well, you ready to go stud?"
 
David was caught really off guard by Tess. He almost shoved her away when she pecked him on the cheek. His face went flush, well more so than it was because of the scotch, and pants tightened a bit, which was impressive given the amount of liquor he had just consumed in such a short amount of time.

"Uhh," he said dazedly, "I don't think I should drive."
 
Tess took the keys from her older brother and led him outside to the valet. As they waited for the car to be brought around, she kept her arm wrapped tightly around David's waist just to make sure he didn't lose his balance. A few moments later the car pulled around and Tess helped her brother into the passenger seat.

"Unless you want me to drive your car back to my place after I drop you off, I should probably stay at your place tonight," Tess observed as they pulled out onto the main street. "Is that okay with you?" Which will give me a chance to talk to you about the photographer and the money I need to borrow from you, she thought to herself.
 
David was impaired, but he wasn't wasted. He had control of his mind for the most part, but the scotch and his id were in control of his body. He knew that Tess staying at his place probably wasn't a good idea, but his body disagreed. Maybe this was finally time to push the envelope with his younger sister, he thought to himself, and if the shit hits the fan, he'll just blame it on being drunk.

"Sure," he agreed with her, "stay at my place."

He knew he was getting very close to the point of no return with Tess, with his own dignity, but as he looked over at his sister all glammed up, all he could think about was her wrapping those tan legs around him.
 
Tess considered a quick stop by her house to grab something to sleep in but decided since it was just David she could sleep in her underwear, or if need be, she could borrow a shirt from him. With no stops to make, they made it to her brother's place about twenty minutes later.

The leggy blonde managed to get her older, inebriated brother out of the car and into his apartment without much trouble. Once they were inside, she took him into his bedroom and helped him down onto the bed. She helped David remove his shoes and socks before swinging his legs up onto the bed and covering him with an afghan that was folded up at the foot of the bed.

"I'll be back in a second with some aspirin and water," she announced as she disappeared into the bathroom. Tess returned a few moments later with the pills and a glass of water, but without her shoes which she had slipped out of. As she padded silently across the carpeted floor she wondered if this was a good time to bring up the topic of the studio session.

"Alright big brother, take these and hopefully you won't wake up with a nasty headache," she suggested, handing him the aspirin and water as she sat down next to him on the bed.
 
The feeling of the soft bed under him was heaven. He really had gotten pretty tired, mostly from the booze he guessed. When Tess brought back the water and pills he sat up and took the water glass from her and swallowed the pills. He drank all of the water in one shot and let out a relieved sigh. He started to feel a little less drunk, maybe just mixing in a water or two during the night was all he needed, but he missed that opportunity.

"Thanks, Tess," he said honestly, "and not just for driving and the aspirin. But for all the effort you went through tonight for me."
 
"Hey, we're a team, right?" Tess said, deciding there was no time like the present. "You helped me out big time with the shoes and the handbag, the least I could do was return the favor by taking you to the party and introducing you to some hot girls, right?" She patted David on the leg as she smiled at him.

"It's perfect. I've got access to a nearly endless supply of beautiful models I can set you up with and you've got...well, money that could help me get my career off the ground," she pointed out. "We're brother and sister, why shouldn't we help each other out?"

Okay, Tess, time to go in for the kill.

"For instance, I met this really famous photographer tonight, Clark Gibbons," she explained as she leaned closer to make sure he was listening. "He's almost impossible for an unknown to get a session with, but he offered to shoot me for like a fifth of what he normally charges. Of course, I don't have the money, but...being the good big brother that you are, you could help me out with that if you wanted. And if you did, I could help you. All you would have to do is name it, and I would do it..."
 
Tess was angling for more money. Maybe this was the time for David to push the envelope, to cross the line with his younger sister. Of course, it was only a few hundred dollars, maybe he would just agree to it, but he was guessing it was a lot more.

"Tess," he said, "I already bought you a ton of shit today. How much are these photos going to cost?"
 
Tess could hear the edge in David's voice and realized she might be pushing her luck. "I know you did and I'm not saying you have to pay for the pictures, I was just using that as an example of how you could help me with my modeling career," she said letting just a hint of disappointment seep into her voice. "I totally understand if you don't want to, I'm just saying that if it was something you might be interested in doing, we should talk about what I can do to make it up to you."

She paused for a long moment before finally answering his actual question, "The studio session is two thousand, but like I said, that is a huge discount off what he normally charges..."
 
"Two thousand?" David asked incredulously.

"I just spent fifty thousand today on a car," he exclaimed.

He was holding back laughter. He didn't want to anger Tess, but the amount of money she was asking from him was clearly insane. She had no concept of the real world and what people have to do in it in order to live. David knew that she was vulnerable now that she had a taste of money. Maybe she really was that desperate for the money, and David could take advantage of her and finally do what he had wanted to do all day.

"If I'm spending two thousand dollars on stuff to hel your career," he started, "then you will have to do a lot of stuff to help me. I can't think of anything of value you can do for me."
 
"Seriously, do you think you could have met any of those girls tonight without my help, let alone gotten their numbers without me talking you up to them first?" Tess asked, losing her cool just a bit. "I know you want to get laid and I'm going to make sure that happens, trust me."

Tess' face had grown slightly flushed as she'd grown frustrated, so she took a deep breath and tried to calm down, "I'm sorry, I know it's a lot to ask, but I really am willing to do whatever you want, you name it. You want to bang a dozen empty headed models, I can make that happen. You want me to clean your apartment every week, I can do that. You want me to wash that new car of yours every week, no problem."

"Come on, David," she said leaning over and sliding a hand up to his stomach. "Don't make me beg."
 
David's pants had tightened when Tess ran her hand on his stomach. He was feeling bold, and he really wanted Tess. He wanted her body badly and his id again was screaming at him to take what he wants. He contemplated the terrible alternative, Tess could blackmail him for any ill advances. He weighed the risk, humiliation and no money, versus the reward, illicit sex with his gorgeous sister.

David's instinct took over and he grabbed his sister's wrist and moved her hand down to his his crotch and rested it on his member now straining at the fabric of his pants. He said nothing but just looked at Tess, no expression on his face. He didn't show anger, or nervousness, just pure stoicism.
 
Tess had no idea what her brother was doing when she felt him take hold of her wrist, at least not until she felt the bulge in his pants, a bulge which she hadn't even noticed until that moment. What the fuck? Was David so completely out of it that he was forgetting that she was his sister? And why was his cock so fucking hard to begin with? Probably all that talk about banging models...

Despite the confusion she was feeling and the desire to pull her hand back, the teen left it there resting gently atop his lap. There was potentially two thousand dollars at stake and the last thing she wanted was to blow her chance at it because of a simple misunderstanding. Tess looked up at her brother who stared back at her, no sign in his eyes that he was incoherent or too intoxicated to know what he was doing.

Of course, if David wasn't drunk out of his mind, then that meant...wait, was her older brother seriously suggesting that she provide him sexual favors in exchange for money? Tess almost jerked her hand away at the very thought of it, but...if she did agree, she would have him wrapped around her finger then. Any time she needed something, all she would have to do would be to threaten to reveal the fact that he had 'taken advantage' of her. It wasn't as if she had never considered sleeping with someone for money, and the one thing that had always stopped her, the fear that they might video tape it or take pictures and then leak them, well, with her own brother, that wasn't exactly something she would have to worry about, was it?

Her hand still resting lightly on his erection, and her eyes still locked on his, Tess decided to see just how far her brother wanted to take this little arrangement he seemed to be proposing, "Just what exactly did you have in mind, big brother?" As she finished speaking, the teenager gave her brother's cock the slightest of squeezes.
 
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