Taming the Gold Digger Ch. 01

She slowly lowered herself into the hot bath. She slid down the porcelain sides until her butt rested firmly on the bottom of the tub. She grabbed her wine glass and took a sip of her aged Cabernet Sauvignon.

It would seem like Jess Maycomb had had a hard day at work and wanted to have a little "Me-time" but that was hardly the case. In fact, Jess hadn't lifted a finger in years to do any sort of hard labor.

Yet, somehow she managed to be sitting in an ornate bathtub surrounded by marble floors, gilded fixtures, and a hand-woven tapestry on the ceiling. She didn't win the lottery, or, at least not directly. She married a billionaire.

As she admired her bathroom she heard the footsteps of her husband.

His name was Jack Shaw. He was 68 years old. His hair was fully gray and he had not a bone of youth in his body. What could have possibly possessed this beautiful, innocent girl to marry this man perplexed most people, but then they figured out the answer: Money, and lots of it. According to Forbes his Net Worth was $4.7 billion. He had made his fortune through inheritance, but continued to build his grandfather's banking empire.

"Honey, I'm off to meeting to discuss the merger, I'll be back in a few hours."

"Okay Jack," She said.

As a young girl, Jack swooned her with shiny jewelry and fast cars. She was only 23 years old and had never met a man like this. She was raised in poverty and to have these things she thought was only possible in a fantasy,.

Jess had only had sex with two men her whole life: Jack, her current husband, and Alex her ex-boyfriend. She was raised in a conservative Christian family in Northern Iowa where there was no tolerance for sexual activity of any sort before marriage.

She realized she had been in the bath for about thirty minutes and figured it had been long enough. She got out of the tub and stared at her glistening body in the mirror. Her gorgeous brown hair that flowed to the small of her back was soaking wet. She had 34D's a tiny waist, and hips that drew comparisons to Marilyn Monroe.

And since she was facing the mirror she was hiding her best asset: Her ass. When she was little boys teased her about it, except for Alex, which is one of the reasons she loved him so much.

On the other hand as an adult men worshipped her ass. She didn't have eyes in the back of her head but she knew that everywhere she went every twist of the hips was being closely monitored. While many women would embrace this, as a result of her conservative household she was sexually repressed. She wore baggy, unflattering clothes everywhere she went and rarely wore makeup. In spite of all this, she was a model.

On a school trip to Chicago when she was 16 she was approached by a scout for a modeling agency. At this age she was already fully developed. Despite her "unorthodox" figure, her bone structure was immaculate and her height was perfect.

When she returned home from the trip and she told her family about the modeling agency they outright refused to let her "flaunt" and "expose" herself to the world.

For a year and a half she waited until her eighteenth birthday. With some money she had saved up she took a bus to Chicago where the same recruiter she had met on her previous trip was waiting. She felt guilty for abandoning her family, but she wasn't meant to live her life on a small Midwest corn farm.

She wrapped the towel around her waist and walked towards the floor-to-ceiling windows of their penthouse that had incredible views of Chicago.

She wondered every day why she didn't choose anyone of the other men walking below her for a husband.

Jack only fucked her about once a month. At his age he didn't have much of a libido, even with a goddess sleeping next to him in bed. She was just arm candy for him.

When they had sex it was horrendous. It was never spontaneous, because Jack needed to take his Cialas before they "made love". He would ruin the surprise by saing, "Where the hell are my god damn cock pills!", which he could never find despite always being in the same place.

After he had achieved a boner fourty five minutes later, he would give off a menacing grin. They would strip simultaneously and then without any foreplay he would stick his dick inside her, pump away for two to three minutes trying to talk dirty and that was that.

He would get dressed and go watch TV. She would lie there thinking of Alex and the first few times they made love, the first of which was always the most special:

They were out in the Maycomb family farm when a thunderstorm suddenly appeared. Alex grabbed her hand and pulled her to the barn. He threw her on a bale of hay and they kissed lovingly. At first it appeared to be nothing more than another innocent make out session, but once they removed there wet clothing sex was inevitable. He had commandeered a condom from a friend, and slipped it on. He slowly entered her as she winced in pain. That pain soon turned to pleasure, a pleasure she would never forget.

They did this a few more times, every once in a while. Too often and they risked the unimaginable punishment from getting caught. Sex felt good for her, but then again she had nothing to compare it too. More important than the sex though was her love for Alex. She wanted to marry him but his life was cut short when an eighteen wheeler collided head on with his truck.

She didn't think she'd ever be able to move on, and she hadn't. She didn't love Jack, he was just there for financial support which she had never had growing up. She was a gold digger, that she didn't deny, but she tried to convince herself her motives were for good.

She got dressed and opened her laptop. Instead of going on one of her many sites, she went to Google and searched "I want a discreet affair". She wasn't searching for a how- to tutorial; she wanted services.

Sure, she could proposition any man on the street for sex. In fact, it happened to her nearly every day that a man would flirt with her, but she wanted to find someone who would not become emotionally attached.

She eventually decided to go on Craigslist. She made an ad for "Gorgeous woman seeking a discreet rendezvous". She put up a picture of her ass and one of her full frontal nude with her face blurred out.

Later that evening she checked her email and it was flooded with desperate men, spammers, couples and a lot of women who wanted what she did, except none of them seemed to fulfill her criteria.

Too old. Too ugly. Dick pic. Dick pic. Too fat.

Just as she finished deleting the dozens of emails, a new one popped in her inbox with the subject, "I know exactly what you're looking for."

She then read his message:

"I know what brings you here. You have a need, a craving. Something that is itching at you every waking hour of the day. It's been building up and you can't take it much longer. That's what brings you here right? I mean why else would a nice lady like you be in a place like this?

Maybe you want to wrap your lips around a hard, pulsating cock and then swallow a big load of cum.

Maybe you want to have your pussy pounded from behind as you're choked, gasping for air.

Maybe the thought of getting caught having sex in the back seat of a stranger's car turns you on like no other.

And perhaps the thought of giving up your pussy to a complete stranger is your deepest, darkest fantasy. It's the perfect combination of danger and play that you so desire...

I could go on... but why not get to the point. Like I said, I know what you want and I'm here to fulfill it.

I offer consulations for this very type of affair. I know you may be skeptical, but here is my phone number: 312-555-4562"

With all the spammers, this didn't seem promising, but it was well put together and he left his phone number, which was odd, but somehow reassuring.

She called the number and after a few rings a man picked up, "Hello."

"Hi this is Jess from Craigslist- I mean, I'm calling because I-"

"I understand," he said reassuringly. "We need to begin immediately. Meet me tonight at 11 PM,"

They hadn't said more than a few sentences and he was already suggesting they meet tonight. "I'm not sure, let me-"

"That wasn't a question, it was a demand." His tone of voice was calm; he knew what he needed to do. "We need to start as soon as possible."

"Okay, I'm sure I can work something out."

"Excellent. Now Jess," he continued, "my operation relies on discretion, fluidity, and teamwork okay? I am going to give you a specific set of instructions that I need you to follow precisely okay?"

"Alright."

"I can't stress this enough. Without following these instructions to a T, there is a chance it may fail?"

"Of course, anything you can do to help."

Now, I need you to get a pen and paper and write this down okay?"

"Sure, hold on one second." She hadn't moved this quickly in years. She darted to her husband's office ironically, sat in his desk and pulled out a pen and paper "Okay, I'm ready."

"We are going to meet at midnight, at Washington Square garage. Go to the top floor and look for a new Black SUV. You'll see it, there shouldn't be any other cars there. Park a few spaces away and then I'll take it from there. Do you have all that?"

"Yes," she said as she furiously scrambled to take notes.

"Moving on. I need you to have your hair looking spectacular, make up done, more so than you're normally comfortable with. I want you to wear a tight dress that makes you feel sexy as well as high heels. Any other accessories feel free to wear. No need for a purse."

"What color panties should I wear?"

"Amy. I told you only follow the directions I told you to. Did I mention panties?"

"No, but I-"

"Amy, please. Just do as I say. I will see you tonight." And with that he hung up.

Soon after the abrupt end to the phone call, her husband returned home.

"Jess! Jess honey where are you?"

She stood up, groomed herself quickly and greeted her husband. They did their perfunctory kiss on the lips. The scene of which was quite humorous because Jess stood several inches taller than Jack and with his deteriorating posture it was only exacerbated.

"Honey, I'm going out with the girls tonight, " she said.

Jack look puzzled, "Girls? What girls? Since when do you go out?" he asked mockingly.

"My model friends," she said with a defensive tone, after realizing she did truly have no friends.

"Ha," he scoffed, "sounds like nothing but trouble to me."

"Just a drink or two, baby, I won't even be home late."

"Fine, go slut it up with your friends." He cried, and waved his hand. He went to the wet bar and poured himself a glass of aged scotch as he shook his head and said, "Women these days."

She was in no mood to argue, so she went upstairs until it was time to go.

She didn't have to meet him until 11:00, but she needed plenty of time to prepare herself both mentally and physically.

The Consultant's demands were simple, but difficult to go through with: He wanted her to look like a whore.

She went into her enormous walk in closet and pulled out a little black dress. It wasn't the same go-to little black dress every stunner has in her closet, no, this was a unique one. It was one she never wore, but only had from a Prada show she did last April. The reason she never wore the dress was because it was too short. Her ass was barely contained by it, her breasts spilled out over the top, and if she wasn't careful her pussy would make an appearance. It was the perfect dress for tonight.

She pulled it off the rack and undressed, admiring herself again in the mirror. She stood in front of the mirror and slowly pulled the dress on. When it first made its way over her ass she thought it would rip, but she kept pulling. Then to her breasts where it was again another challenge, but she managed.

Just like last April it barely fit, but there was a reason it landed her a spot on the runway. It accentuated her amazing curves, which were an anomaly in the modeling world.

She then went to her makeup and put on more than usual, but not an exorbitant amount. She put on the brightest red lipstick she had.

And for the cherry on top she grabbed her six inch black stilettos. She stood nearly six and a half feet tall, which was why she never wore them, but again they were from a modeling job she did.

Her narcissism took hold as she posed in the bathroom mirror. She flashed herself her ass and tits, even her pussy. She blew kisses at herself and winked. She then looked at her watch and realized she needed to leave, now.

Jack sat in the living room watching CNBC so she simply gave him a, "Leaving now, be back around one or so."

He muttered a "yeah, yeah" and out she went.

She went to the garage, got in the Land Rover and sped off. About fifteen minutes later she entered the garage. She followed his directions and it was exactly as he described: Empty. There were a few cars scattered and then she spotted the Black SUV he mentioned.

She parked a few spots down. As soon as she shifted into park her cell phone rang: It was him.

"Hello, I'm here" she said.

"I know, I can see you," he responded. "Did you follow all my directions?"

"Yes. Yes I did exactly as you said."

"Excellent, now let's begin. I want you to walk over to my car and sit in the front seat. Don't look behind you, only straight forward okay?"

"Alright," she got out of the car and walked seductively in her six inch heels towards the car. Her pussy was unbelievably wet and she left a trail of her juices from her car as she walked.

She arrived at the car and didn't look in the backseat. She pulled the door handle and got in.

"Hello Jess," a familiar voice greeted her.

She jumped! "Oh my god!" she looked in the rear view mirror and saw the outline of a handsome face.

"Face forward!" he said assertively.

"I'm sorry. I didn't know you would be back there."

"My apologies, but I can't have you see my face just yet. We need to get acquainted a bit."

Sitting in the passenger seat of a car in a deserted parking lot, with a stranger from Craigslist in the back seat was hardly a way to get to know somebody, but the danger was incredibly arousing. She kept pumping out more juices, which concerned her, but then she noticed a towel over the leather seat: He came prepared.

"Jess, I want you to open the glove compartment."

She did and her jaw dropped at what she saw: It was an arsenal of sex toys. He was like a hitman, but his job was sexual pleasure instead of murder, at least from what she could see so far.

She saw two replica mesh dildos, one average one big, a small vibrator, a butt plug and then some elaborate contraption that looked to be the cross between a dildo and vibrator. There were multiple condoms and lube neatly arranged as well.

She grabbed the small vibrator and he encouraged her with a, "Good choice, but why don't you start with your hands."

She obliged. Her right hand slowly made its way to her radiating vulva. She gently stroked her inner thigh and then made her way up to her swollen labia and then finally to her clit where she got into a consistent rhythm stroking in a circle.

"You're enjoying yourself aren't you," the voice said.

"Uh huh," she whimpered.

She picked up the pace. Her muscles began to tighten. Her lips pursed. She heard some snickering in the backseat, "You're already close to cumming and we haven't brought out the toys yet. Now, I want you to grab the vibrator in front of you. Start on your lips and then work your way to the clit."

She turned it on and gently rested it upon her pussy lips. It felt great, but she wanted more. She rested it on her clit and screamed, "Fuck!" She let out a few more whimpers. The man in the back seat was silent and let her go completely on her own for a few minutes.

Now, she was getting close. "I'm gonna cum," she said.

"Not yet you aren't. Put it down."

"What? But I-"

"Drop it!" He said firmly. "I know you're on edge, but we're not done her just yet. Have you ever been teased by a man Jess?"

"No."

"They've always just had their way and humped you a few times and that was it."

She nodded.

"How much you have to learn," and with that he slowly began to stroke her auburn hair. He ran his fingers from the scalp to the tips. After a few times more times he firmly grabbed her hair by the root. He moved his mouth to her ear and said, "Now, continue."

She put the vibrator back to her clit.

"Good girl," whispered the man.

She kept going. After another minute or so she felt an arm tightly squeeze around her neck, and thrust her head violently into the head rest.

She gasped. Was this man really who he said he was or was he some raving lunatic?

The inherent danger only exacerbated her arousal. She was on the edge again.

"Stop!" He said again. She couldn't stand that he wouldn't let her come, but that just made her want it even more. She now saw what he was doing.

"Jess. Reach into the overhead mirror. There's a blindfold there. Put it on." She followed his orders. "Now, join me in the back seat."

She kicked off her stilettos and climbed into the back seat with his assistance. As if it wasn't already dark enough the blindfold completely removed all light. She felt a hand on her scalp, and it slowly began to stroke her hair.

"Pull your dress down," he commanded. She did and her boobs burst out of the top of the dress. She wiggled around in the seat and managed to pull the dress over her ass.

"Was that dress uncomfortable?" he asked.

"Yes. It's too small," she retorted.

"But you love how it looks, don't you?"

She nodded in agreement.

"You feel so sexy. So naughty. So deviant. You love it." She couldn't see his face, but could imagine he was sporting a lustful grin.

The hand that was stroking her hair stopped. It moved down to her neck, slowly across her clavicle, and rested on her left breast. The hand gently caressed it. She then felt a warm pair of lips kiss her collar bone. The lips kissed their way down to her areola. They circled their way around it for a good minute and then finally swallowed her nipple. She let out a soft sigh.

With his right hand massaging her left breast, she felt his right reach her inner thigh. It made its way up to her vulva. "I'm sure glad I put towels down or else you would have made quite a mess."

She didn't respond. She was too entranced in the moment.

His fingers delicately traced her pussy lips a few times and came to a stop in the middle. A finger slowly entered.

Back and forth, back and forth.

She then felt another finger and her pussy stretched to accommodate it.

"My goodness, you're so tight! Your husband must not be very large."

She shook her head. He was not large at all. She didn't have a large sample size to determine whether or not she preferred big dicks, but Jack's certainly wasn't helping her to determine that.

"Maybe you'd like one a bit more like mine."

He took his right hand from her breast and grabbed her left hand and placed it on his cock. She felt his erect cock through his cotton pants. She held it firm at first, but then slowly stroked it, trying to visualize it with her hands.

The fingers in her pussy slowly began to fuck her harder.

"Fuck, that feels so good!" she said. "Keep going, keep going."

Her muscles began to contract and the man took notice with his fingers. That was his cue to remove them.

This was the third time she had been brought close to orgasm only to be teased. She then felt a hand by her lips. He rubbed his two fingers along her plump lips until she wrapped began to suck them. She tasted so sweet. She began vigorously sucking his two fingers, even grabbing his hand for enthusiasm.