This is a loose sequel to my earlier story "Gaming the System." It is an original work by me and all characters are over 18.
This is a 'weird revenge transformation' story, focusing on two protagonists with similar issues. Lots of straight sex with a couple threesomes. There is some implied quasi-incest, but it doesn't end up that way.
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SATURDAY - RAY
Ray's life had gone off the rails. Less than a year ago he'd been a successful manager at a local software company with a hot wife and several women on the side. His 18 year old daughter had been the one who'd caused everything to turn to shit: He'd successfully convinced his wife he'd been 'downsized' when he'd actually been fired after he'd been caught trying to get one of his best customer support girls to suck him off in his office. His daughter had heard the story through her friends and told his wife, who'd confronted him with the truth. That had led to separation and him being kicked out of the house and into the squalid one bedroom apartment he now lived in. It was close to the only job he'd found, an assistant manager position at the local GamesPlus he knew he was overqualified for.
Ray had just turned fifty-two and still considered himself handsome and fit despite his greying hair and a hint of fat on his belly. Despite his reduced circumstances he tried to look like he was doing well, and still wore his gold watch and drove his BMW whenever he could. Any day how he'd get his apartment cleaned up and could start enticing young women to share it with him.
One Saturday he was on his way in to cover the evening shift when he saw his nemesis: The fat girl with green stripes in her hair who had tricked him and caused his life to fall apart. Her! She was just walking unaware of how horrible she was. She was right across the street, and he'd walk over there now and...
With a screech Ray was hit by a car.
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SATURDAY - CHARLOTTE
Charlotte didn't see the man hit by the car as she sucked the straw in her iced coffee. She was sitting at an outside table writing in a notebook, scrawling notes for her game later that night when her players would encounter a gigantic dragon who would sexily offer them various deals she'd worked out. She had a suspicion that if things went as she expected Brad's warlock would accept the she-dragon as patron and she could convince him to come by her place one night to 'discuss his character.' She'd seen the way Brad looked at her tits and had heard him telling Greg about his miserably luck dating.
She was here to check out a store just a few blocks from her apartment. The local GamesPlus mostly focused on video games and related merch, but she'd heard they'd recently expanded and added tabletop gaming books. Probably just 5e and such due to the recent fad, but worth checking out. Her hope was that they had a table she could play on. She'd run a game at the local library for a while, but a librarian had caught her letting Kevin Milton have his 18th birthday present and apparently they didn't approve of her having a guy finger her fat snatch during a 'private character discussion' in the event room.
Charlotte was twenty-six. She worked at a local big-box store running the register or stocking shelves as asked, utterly ignoring the English Literature degree her parents had paid for. She'd moved out for years ago and hadn't talked to them in years, living only for her multiple weekly RPG sessions. A trust fund her parents had granted her covered her rent. Her meager paycheck covered other mundane expenses, and a string of gifts from her boyfriends kept her well-fed, well-dressed, and most importantly of all, amused.
She made do with another game store across town on alternate Saturdays and her private game Tuesday nights at her nearby apartment. The store game made it easier to find new players that met her needs, while the home game made it easier to ask one or two of them to stay behind for some special game time.
She was tall for a woman and a bit on the chubby side, but it had given her big boobs which worked wonders on the young men she invited to her gaming table. She was dressed in a simple string top covered by a sweatshirt and floral-print leggings. Her hair was a dirty blond mass falling down her back. She was attractive, undoubtedly due to the sense of confidence she exuded.
She drank her iced coffee as the emergency crew worked across the street, considering how this would inconvenience her schedule. She ended up slipping out to avoid any entanglements. The last thing she needed was being called as a witness for this accident and disrupting her schedule! She'd have to return to the GamesPlus to check it out another day.
That night she dreamed. She was at a dingy Vegas-style casino with a hint of cigarette smoke in the air causing her eyes to water as she puckered her purple-painted lips. The casino brought back memories of a trip to Las Vegas a couple years ago: Marcus had paid for the whole thing, but seemed offended when she'd complained about the cheap hotel they were staying in. She'd ended up drunkenly kissing some random guy and pinning him to the wall. Marcus had forgiven her, of course; She had made sure he had no illusions about his ability to score a woman like her again.
She found herself at a blackjack table watching the dealer play some inscrutable game that didn't use cards, but the multiple kinds of polyhedral dice common to tabletop role-playing games. She found herself focusing on the dealer, expecting to see herself in the role, but instead a thin brunette met her gaze with her own piercing stare.
The other woman smiled, "I'm Anna, and I'm a witch."
Charlotte smiled: She'd had dreams like this before. She'd had good luck controlling her dreams in the past and assumed this would go the expected way.
"I see you're having trouble accepting things, and I understand. In short, you've been cursed because of the lives you've ruined. Mostly minor things, but a few more serious. Interestingly, I got a two-for-one deal, so you'll be sharing your punishment with one other target."
"I don't really like to share."
"Tough titties." The woman smiled, dropping a single die from her elegant and dextrous hand onto the green felt of the table.
You're a gamer, right? Specifically the tabletop in-person role-playing type." the dealer continued, her hand moving over the die, barely touching it and causing it to bounce around the table. The die was a translucent red, with the numbers sparking with gold in the deep lines that marked each side. "Here's the deal. You have about a week to reconsider things, and then we discuss next steps. Each day you'll roll this die and it will cause a bit of a change in your circumstances."