Winning

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Status: Finished  |  Genre: Romance  |  House: Booksie Classic


Jeb won the lotto, but wasn't sure how great it was.

Submitted: March 28, 2018

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Submitted: March 28, 2018

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Jeb looked out of the second story window of his mansion, and surveyed the considerable spoils of his newfound wealth.  Like a familiar hillbilly from a TV show, Jeb, who was more than aware of the irony of his name so closely resembling the TV family's patriarch, bought everything he could dream of until he hit a plateau.  The loss of inspiration and development of boredom were evident in his lapse in hygiene and the mess that occupied his driveway and front yard.  He looked out his window and saw the Ferrari that, though crashed beyond repair, caught the sun on its brilliant red paint and made his manliness instinctively pump up inside him.  Other classic cars, in various stages of disrepair, also lined the rubber-streaked, drag strip of a driveway.  Crazy parties, multiple homes for him and his friends, chefs, maids in lacy black uniforms, a disastrous trip to the casino, that would have put anyone else in the poorhouse, and, of course, dirt bikes and four wheelers.  The ‘stuff’ just couldn't help keep his mind off the more pressing matters of the day.  It sucked!

The first couple of weeks being filthy rich had their ups and downs, but, this week, had been quite stressful.  Jeb took things in stride though as he smoked the last bit of the dynamite pot his doctor had prescribed after the win.  It really didn't help his anxiety, but definitely got him higher than anything he had ever smoked.  He could hear the murmurings of the people who were gathered in the dining room.  They were waiting quietly and patiently for him to join them for this evening's festivities.  Jeb contemplated the last few months as he sat in a chair that cost him more than the car he owned before the Powerball win.  A large, framed photo of him being presented a giant, cardboard check from the lotto officials graced the otherwise, barren bedroom wall behind him.  He played the lottery, religiously, for years, and was very happy to be the largest winner in lotto history...at first anyway.  His timing stunk, but what the hell.  He spent a rousing, drunk first night of being rich throwing bundles of hundred dollar bills to pedestrians on Main Street from the sunroof of his new car.  To date, he had spent over thirty million dollars on 'nothing'.  Jeb couldn't help wondering, 'why me…why now'.

A chime signaled the presence of a visitor, at the large metal gate at the end of his very long driveway.  He hoped it was the person he had been expecting all day; someone who might make his life a bit more fulfilling.  A woman's voice, full of uncertainty, came over the intercom asking to be admitted.  Jeb recognized her as the 'one that got away'.  It was a girl, now a woman, who had eluded his advances whilst in their early twenties, and eventually rebuked him; sending him into a stormy relationship with the woman who would become his first, and then, second wife.  He tried to contain his excitement, while letting her stew a little.  He listened to her explain who she was and why she was here to the automated entry system.  The guard, who would normally be there to greet guests and ensure only 'friendlies' could enter, was off on some 'voyage of discovery', that he had been putting off until the perfect time.  Understandably, that time just happened to be now.

Jeb buzzed the woman in, and could barely stand it, as he waited for her to traverse his 'obstacle course' driveway, and arrive at his front stoop.  He opened the door as she pulled up and escorted her over the top of the pile of love and hate mail that seemed to come from the four corners of the Earth.  It was amazing how popular and unpopular a few hundred million dollars could make an, otherwise, boring, plain-looking gentleman like himself.  He opened the door and greeted 'Kerrie' before giving her a long hug.  She had an uncomfortable look on her face, as he squeezed her tightly.  What he remembered as a great, near-love story, was, in her mind, a distant memory of some guy who couldn't take no for an answer, until it was, literally, screamed into his face.  Things were different now and Jeb could afford whatever she was looking for.  It was obvious to him that she was looking for 'safe territory'.  A safety net he now had the means to provide for the woman of his dreams, after she had a turbulent week or two of her own.  He pushed her out to arm's length so he could get a good look at her.  She looked older than he remembered, but of course, that's what happens; we get older.  He still remembered the night they kissed, though it only happened once while they were quite drunk. 

Jeb was in control because he held all the cards now, and Kerrie hoped he would be willing to give her what she needed.  Though the money didn't buy him any real happiness, it had now resulted in a reunion that he had long dreamed of.  He pulled her into him and kissed her passionately.  She didn't react positively to his advance at first, but finally relented as they walked, in a clinch, to an expensive new couch.  They fell down onto it together and made love.  While the two were clumsily going through the motions of having awkward, unprotected intercourse, Jeb thought the two lovebirds were making passionate love like two ‘A list’ actors on the big screen at the drive in.  She tried to hold back her disgust as he huffed and puffed and slobbered a little on her shoulder.  He just knew it would be one for the ages, and chided himself in his head for not videotaping it.

When they finished, Kerrie went to the bathroom to freshen up.  Afterwards, Jeb showed her the crazy mansion he purchased without wasting any time negotiating the price.  He took her from room to room and showed her all the cool things that were there when he moved in, and those things he had brought in.  She followed him around, but kept looking around like there was something more she expected to see.  He couldn’t keep his hands off her as they finished the last of the walk through, and she was half-afraid the fifty-something-year-old jackass might want to go for 'seconds'.

With the tour complete, Jeb took her into the deserted kitchen and made each of them a sandwich.  They talked about what had been going on in their lives as they ate and had a few glasses of wine.  Kerrie had been married and divorced a couple of times, but didn't have any children.  When the economy crashed, her job was eliminated and it had left her just scraping by.  Jeb contacted her to come and visit him in all his newfound wealth and resources at just the right time.  She was desperate, but didn't say it to him.  She looked at him and suddenly felt quite drunk.  She was slurring her words and looking to her host for the answer to why she was getting ‘smashed’ off only a couple glasses of wine.  She realized, too late, that she had been drugged, before falling off into dreamland. 

The room was spinning a little when she regained consciousness.  Jeb was addressing his family and friends, and, of course, his new squeeze, Kerrie.  She wasn’t lucid enough to understand what he was saying, but heard what sounded like several muffled voices trying to talk back to him.  She couldn't make out any part of what they were saying, or what they wanted from him.  She quickly realized that she was sitting at a long table where several shadowy figures were also seated.  As the cobwebs finally cleared, she recognized some of them from pictures that were on display throughout the house, and from her memories of his family back in the day.  Apparently, Jeb had everyone who was 'important' to him, including her, shackled to a dining room table.  There were piles of cash lying all over the room to tease the collection of gold diggers and leaches.  Everyone but Kerrie was gagged, and she could hear the others, who included a variety of aunts, uncles and past "frenemies", and acquaintances, frantically trying to communicate with her.  Jeb looked at his captive audience and told them how much he loved them, and appreciated their coming to visit him after his big win.  He "hoped they understood" that, in this situation they were all facing, he "knew what was best for all of them".  After honking Kerrie’s breast, he walked over, sat down near the window, and stared outdoors.  As Kerrie tried to slip her hands out of the steel manacles that held them to the table, Jeb swiveled around in his chair and smiled maniacally at the group.  Everyone tried to look happy and humor him; while hoping that he would come to his senses.  He just swung around to look out again.  The woman Jeb loved from afar for so long suddenly realized that the 'shelter' she had sought with this man didn't exist. 

Out of the window it looked like the sun was coming up.  It was odd that it was rising in the South, and equally weird that it was rising at nearly six o'clock in the evening.  As his guests continued to squirm and try to escape, Jeb stared intently at what they all knew was the planet-killing asteroid that had been predicted by the scientists.  Kerrie thought how stupid she was to believe that a half-wit like Jeb would have had a deep shelter built instead of buying fast cars, and manipulating an old 'girlfriend' into screwing him.  She couldn't believe she actually let this jerk put his hands on her.  As the Earth began to rumble and shake underneath them, Jeb mumbled something about "getting this over with and limiting his loved ones' suffering".  As the big rock, that was scheduled to kill all of humanity today, made impact about thirty miles away, Jeb turned his head to speak to his 'loved ones'.  People who hadn't thought to visit him before the lotto win and the pending disaster was announced.  Jeb took the last drag off the tiny ‘roach’ he found left over from his pot stash, and held the smoke in until it made him cough violently.  He finally managed to yell over his shoulder, "I'm glad you all came...I picked this location for this very reason...best seats on the planet...no need to worry, it will all be over in a minute".


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