Debbie the Dumb Gold Digger

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INTRODUCTION & DISCLAIMER – In this story, we travel back to 1991 & meet 18-year-old Amy, a young woman who behind her pretty face keeps some big secrets, and is constantly frustrated by her twin brother Seth’s ultra controlling religious girlfriend Kelly and her widowed grandfather’s much younger and dim-witted girlfriend Debbie, who just happened to appear when the infirm, elderly man had a substantial lottery win.

But while with Kelly it appears to be a case of what you see is what you get, could there be more to the vapid vulture Debbie than meets the eye?

Find out by reading this amusing and sexy story. All characters and events are fictional, with any similarity to living persons real or dead coincidental and unintentional. Only characters aged 18 and over are involved in any sexual situations.


Sitting in the back of her parents’ car, 18-year-old Amy Jenkins felt like she had visited her gynecologist and been given a hormone injection that gave her a year’s worth of PMS at once, although her actual time of the month was not due for another two weeks or so.

The pretty and petite girl with long brown hair, a doll-like face with deep brown eyes and a perfect, naturally tanned complexion due to an Italian background on her mother’s side, had had a pretty reasonable day this fine spring Wednesday at the high school on Chicago’s North Shore she attended as a Senior, and from which she would graduate from in two months’ time as part of the Class of 1991.

Between her legs, Amy could feel her panties riding up between the cheeks of her bottom, and the teenager discretely reached down to adjust them through her jeans. However, uncooperative undies while irritating enough were not the main cause of Amy’s annoyance. One source of irritation was in the back of the car with her, the other was awaiting her at their destination this evening.

Glancing into the front of the car, Amy looked at her parents Warren and Fran. Her father drove in silence, her mother sat in the front passenger seat also in silence, their facial expressions apprehensive as they anticipated what awaited them at their destination.

Besides Amy, two of the four people in the back of the car were her brothers, Seth and Josh. The structure of the Jenkins family was quite unusual. In November 1972, Fran had given birth to fraternal twins Amy and Seth and for some 15 years the Jenkins family was a perfect nuclear family – mother, father, son and daughter. Then in 1987, Fran Jenkins found she was late – very late – and woke up feeling very queasy every morning. Other times she would get up in the middle of the night to fix herself peanut butter, celery, grapefruit and pastrami sandwiches. Not surprisingly, early in 1988 Fran at age 41 gave birth to Josh, and Seth and Amy had a baby brother 15 years their junior. This age difference caused embarrassment on several occasions, such as a day at the zoo when Amy and her mother took Josh on an outing, and some people assumed that Amy was a teen mother and Fran the boy’s grandmother.

This evening, young Josh sat in his booster seat opposite Amy playing with a toy robot, the three-year-old blissfully oblivious to the concerns of his parents and his older sister. Amy glanced towards her twin, and saw that as usual he was staring at the object of his affections with a love-sick, dreamy look in his eyes that were brown like those of his twin sister.

The object of Seth’s affections was the first source of Amy’s irritation this evening. Her name was Kelly Crane, and she was a slim and pretty 18-year-old redhead, her long red hair tied back in a pony-tail with a blue ribbon that matched the color of her eyes. She had enrolled in Seth and Amy’s high school at the start of their junior year, and Amy could only curse the Illinois Education Department and their budget cutting measures. The neighboring high school Kelly had previously attended had a declining attendance, so the decision was made to close the school and redistribute the students to the three adjacent high schools. On the first day of junior year the newly arrived Kelly looked at Seth, Seth looked at Kelly and that was it, love at first sight.

In his younger years, Seth and his friends had always loved science fiction, and when Kelly arrived on the scene, Amy sarcastically thought that maybe she came from a galaxy far, far away, rather than a neighboring North Shore suburb. But Kelly was no science fiction fan, in fact quite the opposite. The only books, TV shows and movies Kelly was interested in were connected with one book, possibly the most famous book in the world.

Kelly’s father was the Minister of a fundamentalist Christian church, and Kelly – the second eldest of six kids – believed every word of the Bible was literally true. The girl was convinced that the Earth was only 6000 years old, and simply dismissed as imaginary irksome things such as dinosaurs, trilobites, wooly mammoths, sabre tooth cats and Neanderthal men that might have cast doubt on her beliefs, despite fossil evidence to sincan suriyeli escort prove their existence.

Kelly arrived at her new school with a younger brother and sister, two cousins and a posse of friends from the closed high school, all fundamentalist Christians, and a new Christian clique immediately made its presence felt in the school. Seth was so besotted by Kelly, following her around like a dog with its tongue hanging out, that he was immediately drawn into this group away from his existing circle of friends, and was soon attending bible study and prayer meetings, promoting abstinence, assisting his girlfriend in getting the popular board game Dungeons and Dragons banned at the school, and handing out religious pamphlets to other students as they arrived for school.

The most significant trait of Kelly was that she thought everything in life – good, bad or indifferent – was caused by the will of God. Tonight was no exception. “Didn’t Our Lord provide us with such a beautiful spring day?” Kelly asked.

“He sure did,” Seth agreed.

Amy stifled a sigh and stared out the car window to disguise her eye-roll. The reason Chicago had had such a nice spring day was due to favorable weather conditions over Illinois and Lake Michigan, not due to the will of a higher power. And of course, love-sick Seth had to agree with everything Kelly said. If Kelly said that an orange was blue and a lemon was purple, Seth would agree.

Still, at least Kelly’s opinion on the weather was minor compared to some of the opinions Amy had heard the girl express. Several weeks earlier, Amy and her best friend, a pretty 18-year-old Jewish girl named Gretchen Goldstein were in the girls’ room, both feeling the worse for wear as they had their periods and bad menstrual cramps. As they were standing at the sinks taking some tablets to try to alleviate this, in walked Kelly who was also at this stage in her monthly cycle. The pretty redhead said as she swallowed her own period pain tablets that it was God’s will that determined when women got their periods, and that any discomfort that they suffered during this time of the month was due to His testing of their faith. Amy and Gretchen tended to believe that this was caused by the fact that they and Kelly had all failed to fall pregnant during their current menstrual cycles and they were shedding the linings that had formed on the walls of their uteruses, but obviously Kelly knew more.

Again, Amy watched Kelly and Seth strengthen their hand hold and stare at each other with dreamy eyes, and wished that she had a bucket close handy in case she threw up from all the saccharine. The teenager could also see by looking into the front of the car that her parents were not so thrilled by their son’s choice of girlfriend, and the tight controlling hold she had over Seth. But as much as Amy disliked the fact that her twin brother was under the spell of his girlfriend, he was not the only male in her family to become completely besotted by a pretty girl in recent times. The other man was her paternal grandfather Stan. It was to his house, for his seventy-ninth birthday where they were headed. And there waiting for them would be his girlfriend Debbie, the second female who was causing Amy such irritation on this otherwise pleasant Chicago evening.


As a child and younger teenager Amy had loved visiting her grandparents on both sides. Her maternal grandparents, slightly younger than her paternal grandparents, she and Seth always called ‘Nonno and Nonna’ due to their Italian background, were really enjoying their retirement, both fit and active, loving spending time with their adult children and grandchildren.

Until several years ago, Seth and Amy had always enjoyed spending time with their paternal grandparents Stan and Mary. But early in 1989, Grandma Mary was diagnosed with pancreatic cancer, and was gone within six weeks. The death of his wife of so many years sent Stan’s own health into a downward spiral, and within months he had changed from a sensible, competent and independent senior citizen into a frail, forgetful and doddering old man who could barely remember his own name some days, and other days would believe he was in the past. On more than one occasion Stan believed he was still a GI storming the beaches of Normandy during D-Day in 1944, rather than a retiree in suburban Chicago in 1989.

Like many elderly people with aged-related health problems, Stan became stubborn and difficult to reason with, and resisted any attempts by his adult sons and daughters to help him. Totally against moving to an aged care facility or even going to live with relatives, the old man would put on a convincing act to doctors that he was perfectly okay, and fine to live alone.

One thing Stan did remember was the same combination of numbers he and his late wife had always chosen for the lottery that they had played every week for years, never winning more than fifty dollars. He never forgot to buy a lottery ticket, although one day sincan özbek escort he did forget his way home from the shopping center less than a mile from his house after buying a ticket and ended up in Joliet, running out of gas in the middle of a major intersection. Fortunately Stan did find his way home okay after buying the Christmas 1989 ticket. And the winner of four million dollars was Stan Jenkins.

The Jenkins family were not any less worried about the old man now that he was a multi-millionaire, in fact they worried about him all the more. The four million dollar prize was deposited into a low interest savings account at the bank, but Stan did not change his ways and steadfastly refused to listen to the advice of well-meaning family members. Despite having the money to pay professionals Stan decided to re-paint the exterior of his house himself, retrieving from the garage dried out brushes and many different colored cans of paint –some water-based, others oil-based – containing dregs that were decades old and making the exterior of the dwelling look like it had been covered in graffiti by a color-blind clown. The only ones who were forced to spend money were Warren and his brother, fixing up the mess their father had made of his house.

Pleas by Warren, his brother and two sisters to their father to spend some of the money to move to an assisted living facility for the elderly all fell upon deaf ears. Then, as if by magic, along came Debbie and suddenly Stan had no problem spending his wealth.

Warren turned into the street where his father’s house was located, and looked at his wife. “I don’t know what to be more worried about, Fran,” he said. “That things won’t be different, or that things will be different.”

Fran gave her husband a sardonic smile. “With your father and Debbie, anything is possible.”

“I think it’s wonderful that Jesus sent Debbie to your father to keep him company in his older years,” commented Kelly.

Again, Amy rolled her eyes discretely. Of course Kelly thought Debbie’s arrival was due to higher intervention, not a mooching and dim-witted young woman seeing a senile elderly man with a four million dollar bank balance as an easy meal ticket and moving in like a hyena or vulture scavenging on the body of a dead wildebeest on the African plains.

“Well, the house is still standing and Dad hasn’t tried painting it again,” observed Warren as the house came into sight, and the lack of any other cars indicated that they were the first to arrive.

“But that’s new,” said Fran, pointing at what stood further up the driveway, the jaws of Amy and her parents falling open in shock at the boat that sat on a trailer. Atop the boat stood Stan Jenkins, the elderly man wearing a sea captain’s hat and staring vacantly out into the darkness.

“I have a really bad feeling about this,” said Warren, as he got out of the car, stress showing on his face and looked up at his father. Stan failed to acknowledge the presence of his son, daughter-in-law, grandchildren and older grandson’s girlfriend.

“Um hi Dad, happy birthday, what are you doing up there?” Warren asked his father uncertainly. His father, even when younger and competent, had never expressed any desire to own a boat. And while Debbie never had any problems convincing Stan to spend money upon her, such as her expensive car that was parked in the garage, jewelry and many, many clothes, a boat really didn’t seem like the sort of thing she would want either.

“I’m sailing my new boat,” Stan announced proudly.

“I see that,” said Warren. “So, how long have you had your new boat?”

“We bought it this Monday,” came a young female voice, high-pitched and girlish, everyone turning to see Debbie exit the front door of the house and walk towards the family. A reasonably tall and stunningly attractive girl, 23-year-old Debbie possessed the classic Midwestern look of long blonde hair, styled with a prominent fringe, big blue eyes and a perfect fair complexion. She wore a light blue tee-shirt that accentuated her large breasts, and on her bottom half a pair of black stirrup pants that showed off her shapely legs and buttocks, the stirrups tight around Debbie’s bare feet. Amy could not help noticing when Debbie got closer that her tight leggings also showed the young woman’s panty lines and the indentation of her vagina at the front.

“Having fun up there, sweetie?” Debbie called to Stan, the young woman giving the old man a wave.

“Oh yes, lots,” agreed Stan, continuing to stare out across the street. “I sailed it on Lake Michigan yesterday.”

“Hi Warren and Fran,” said Debbie in her high-pitched voice. “Hi kids!”

“Hello Debbie,” said Warren, maintaining an even tone. “I have to ask, what is the story with the boat?”

“Stan thought it would be a good idea to buy it,” said Debbie. “So, here it is.”

The other members of the Jenkins family strongly doubted this, but Stan was so forgetful it would be difficult to ascertain the truth. Still sincan rus escort standing on the boat, the elderly man stared vacantly into the night skies, before blurting out, “Michael Jordan sold us the boat.”

“Michael Jordan? The basketball player?” asked a disbelieving Warren.

“That’s right, he did,” Debbie asserted to Stan, before turning to Warren and Fran. “He didn’t really, the boat salesman just looked like Michael Jordan.”

“Please tell me that Stan didn’t take the boat out on Lake Michigan?” asked Fran, thinking of the horrors this could cause.

“No, my stepfather Jim took the boat out and me, my Mom, my best friend Vanessa and Stan were passengers,” said Debbie. “Jim loves sailing and fishing. In fact, the boat is half an investment.”

“Half an investment?” Warren, who worked in finance knew Debbie was not well versed in this field, and her only grasp of obtaining money was leaching off a senile, elderly man with a substantial bank balance. So what was the brainless blonde bimbo on about now, talking about ‘half investments?’

“I mean, it’s half our boat and half Jim’s boat,” said Debbie. “In fact, it was Jim who said what a good idea it would be to buy a boat, and he said he’d pay half the money towards it when he gets his tax refund.”

Warren, Fran and Amy all exchanged a glance. It made sense now. What wasn’t clear was whether dim-witted Debbie had been conned herself, or was in on the scheme with her stepfather, but getting to the truth would be difficult. Not because Debbie was a great liar, but because she was too stupid to hold a proper conversation with.

Seth and Kelly did not exchange the glance of Seth’s parents and sister, as they were too busy staring into each other’s eyes as they held hands. Three-year-old Josh of course had no understanding of any of this, and was more interested in his toy robot and the children’s book his mother had given him to keep him occupied.

“Why don’t you all come inside?” Debbie said, leading the way towards the front door. Stan made no attempt to get down from the boat, the old man continuing to stare vacantly into space.

“Um Dad, why don’t you come with us?” Warren suggested, his father either purposely ignoring the suggestion or having no concept of his son standing right there.

“Oh, he’s fine up there, he loves it, don’t you Stan?” asked Debbie. The elderly man nodded in agreement. “See, he’s fine,” the young woman asserted.

“Yes, but what about when he has to get down from there?” Fran asked. She knew her easily-confused father-in-law was physically frail, and getting down the ladder to the ground would be very difficult for a man in such poor health.

Debbie shrugged indifferently. “He’s never had any problems getting down. He’ll come down when he’s good and ready.”

With some reluctance, Warren and Fran followed their hostess inside, Warren guiding Josh and Fran carrying a cake in a box, followed by the teenagers.

“I hope you’re hungry, because I’ve been cooking all afternoon,” said Debbie.

Again, the Jenkins family looked at each other, wondering what horrors this could entail. Debbie showed very few talents in life, and cooking was definitely not among them.

“Do you like Chinese food?” Debbie asked.

“Um, yes,” said Warren, his voice full of uncertainty. A tall blonde Midwestern girl could not look more out of place preparing Asian food.

“Good, you’ll love my home-made sushi and sukiyaki then,” Debbie asserted.

The frustrated Fran spoke up. “Debbie, you do realize that sushi and sukiyaki are from Japan and not China, don’t you?”

Debbie stared back at her with a confused, vacant expression in her blue eyes as her mind tried to piece things together. “Aren’t they the same thing?” the young woman eventually responded.

“No, definitely not,” said Fran. She stifled a sigh. A little thing called the Second World War was irrefutable proof that Japan and China were not one and the same.

Again, the Jenkins family could see Debbie trying to slowly piece things together in her mind. “But they’re both Asian,” the girl finally said.

“Yes, they are both in Asia,” said Fran, pondering how long she could last before losing her patience. When younger, Fran’s brother had been an Italian Casanova-type, picking up one girl after another, many of them not overly blessed with brains. And as a school services officer, Fran had met plenty of dumb people in her job – kids, parents and even teachers who had somehow obtained their teaching diplomas – but nothing to rival dopey Debbie. “But they are completely different countries.”

“Oh,” said Debbie. The blonde thought again. “Is that like us and Canadia?”

Amy put her hand over her mouth to suppress laughter at the way Debbie had mispronounced the country to their northern border. One thing was for sure, if Debbie did visit ‘Canadia’ she wouldn’t want to use that pronunciation to a group of lumberjacks or ice hockey fans.

“Yes,” said Fran tersely, as Debbie’s attention – limited at best – turned to Josh.

“You just get bigger and taller every time I see you,” said Debbie, bending over to pat the small boy on his head. With Debbie’s back to the other family members, Amy was unable to avoid seeing the oval shape of Debbie’s pussy through the tight fabric of her stirrup pants.

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