Clearing the debt

Looking up you see his cock floating a few inches from your eyes, a few drops of cum dripping down from the tip. You can feel his hot, sticky cum plastered over your face and exposed breasts.

"Good little cum slut. Clean your Master's cock with your mouth then lick up all the cum I gave you."

How did it come to this? And why did it make you so hot?


Six months ago you were a young advertising executive with two huge successful campaigns to your credit. Fresh out of college, you rose quickly, taking the advertising world by storm. You had a mansion, a few cars, everything you ever wanted and more. Extravagant vacations, ridiculous status items, the works. Then came that last account. You bet everything on one huge campaign, so certain you were unstoppable. If it succeeded you were going to be the youngest VP in your company, and oh the money!

But it failed, and failed spectacularly. You got fired. No other ad agency would touch you. You used up your savings in the first month, looking for work. You sold everything and were still millions in debt. You needed a way out. You broke down and called Jack.

Jack was an ex-boyfriend from college. You broke up because he didn't take life as seriously as you did, and you couldn't see a future with him. He was a dreamer. Which led him to day trading in the stock market and building a vast fortune. It led him to investing in start up companies that other people wouldn't touch because of the high risk, which built him another fortune. It led him to investing in Marvel studios, back in 2007 before Iron Man came out, which made him a fortune every time one of their movies were released.

Jack had the money to fix all your problems and he wouldn't even miss it. But would he do that for you? You were going to have to humiliate yourself and admit you were wrong back in college. And you weren't prepared for what the price would be for his help.

_________________


Ooc: Jack requires you to be his sex slave until your debt is paid.

Looking for a female writer. May require multiple roles down the line. If you're interested in the story, shoot me a PM and we'll talk ideas.

This post isn't the first post in the story, rather it's a rough sketch of what I want to do with the thread.

How it all began

Jack was sitting in a crowded Starbucks, in Manhatten, drinking an overpriced, pretentious coffee. He was easily the best dressed person in the room, wearing one of his many bespoke suits made by his personal tailor on Savile Row. The suit probably cost as much as the rest of the clothes in the room. He had come from a manicure and hair styling. At six foot two, a chiseled physique and his boyish good looks, and short blonde hair, Jack looked like Adonis. He screamed sex and success.

Jack was a simple guy. Most days he pursued whatever hobby caught his fancy wearing clothes he bought from Wal-Mart. He had made his fortune reading business prospectuses and reports and investing in high risk ventures starting back in high school after playing the stock market game. He had thought it would take most of his life to retire, but it wasn't long after college that some of his high risk investments went big and Jack was a millionaire. So for an hour or two a day he studied up on the latest business news to grow his fortune, and the rest of his day was leisure.

Normally, it would took a business offer that could potentially make him millions for him to put on one of these suits and meet someone. Oh, he wore them for celebration parties for big successes, and after he made a great deal of money in Hollywood he wore them to all the parties he got invited to when a movie was successful. Even then he hated putting on the suits and getting all dressed up.

Today, Jack wouldn't miss it for the world.

She had been his first serious girlfriend. Oh there had been other girls in high school, and even a few other girls he had dated in college, but she had been the first girl he could see a future with. Jack was thinking about marriage, screwing up his courage to ask her father's permission and working out the best way to ask her, something that would be memorable.

She broke up with him. She didn't see a future together because Jack would never amount to anything.

That was years ago. Jack hadn't forgotten.

So when she had called and asked to meet up, Jack readily agreed. It was petty, sure, but he was going to rub his success in her face. Show off, brag about his accomplishments, drop a few names, maybe call Scarlet Johansson or Jennifer Lawrence when she uses the bathroom so he can be on the phone with them when she comes back to their table.

Clearly she was calling to get back together, why else would she call? He was going to turn her down, politely, with as much class as possible after making her eat crow. Hence why he was decked out to the nines in a Starbucks.

Jack sipped his coffee and waited for her to arrive.

Sophie had dressed up. Sort of. There was only so much you could do to dress up for a 'date' in Starbucks, but she had someone to impress. Most of her truly expensive outfits had gone the way of everything else. Sold in a desperate attempt to stave off her debtors. She'd kept a hold of a few things that looked good though.

She wasn't overdressed, in a tight fitting skirt and a white top. An outfit that was simple, but that she knew hugged her body in just the right ways. She adjusted the neckline a little, making sure it showed off her cleavage. No one in the corporate world would touch her since she'd made that last massive gamble. This was a last resort, and she was committed to using every weapon at her disposal to get what she needed. And she had plenty of those. Success was visual, and Sophie looked every inch the successful independent woman. Five six meant she was taller than most women, with long, smooth legs and a tan, that although fading, showed that she had the time and money to get away on expensive vacations. Her body was lithe and toned, with small breasts, a tight ass shown off nicely by her skirt, and a flat stomach.

Pausing just before the coffee shop, she adjusted her hair in the reflection offered by a shop window. It was long, clearly well-cared for, even if lately her hair dresser had been decidedly low market than the man she had once visited every two weeks. Flowing like a black waterfall down past her shoulders and almost to the small. She'd always been proud of her hair, and she carefully teased back a few stray strands, glad that she'd still had a little of her expensive shampoos and conditioners left to prepare for this date. She needed to blow Jack away.

Their breakup hadn't been the best, but Sophie was accustomed to wrapping men around her finger, she was sure that Jack, no matter his success, would be no different. Eventually happy with how she looked, Sophie walked around the corner and entered the Starbucks, her heels clicking on the hard floor. She didn't bother looking around yet, she needed to remind Jack that she held the power here, she'd ended the relationship, she was interested in maybe renewing things. He didn't need to know just how desperate she actually was at this point.

Instead Sophie walked straight to the counter, ordering an Americano from the gawping teen there. It took him a moment to register that the beautiful woman who had just entered had asked him for something, but he jumped to it with alacrity when she gave him a pointed look. She took some satisfaction from having that effect on men.

Drink in hand, eventually she turned to scan the coffee shop, spotting Jack sat about halfway across the room. She almost had the same reaction the boy behind the counter had when he saw her. Jack had always been good looking, but age and wealth had clearly had a good effect on him. The suit he was wearing looked like it cost as much as some of the cars on the street outside, and his chiseled jawline looked all the better for his increased maturity. Catching herself, she walked over.

"Hey Jack, you look good."

Numbers scrolled across the screen of his phone. He held it in his left hand, scrolling his screen with his thumb as he sipped his coffee with his right hand. To an outward observer, Jack didn't seem to be paying much attention to his phone, after all he was only glancing at it as he looked out the window, but in fact he was scrutinizing every number, comparing it to where it had been yesterday at this time. He had millions invested in the futures market, and was planning to unload it all in the next three days.

He figured he would get some work done while he waited for Sophie.

"Hey Jack, you look good."

He didn't look at her right away, his vision was on the numbers for canola oil at the moment. It only took a second to compare the number to where it was yesterday, but he wasn't going to interrupt his work for his ex from college.

Part of him regretted how petty this was. He should have just told her he wasn't interested over the phone when she had called. It would have been quicker and easier. But not nearly as much fun.

After letting her wait a full second, Jack turned his head to face her and smiled. He stood, obstensibly not looking her up and down. He put the coffee cup on the table as he stood and slipped the phone into his pocket, freeing both hands. He offered Sophie his hand to shake.

"Thank you Sophie, you look," he paused, taking a moment now to slowly look her up and down, letting her see his eyes go down her body and back up. She did look good, but there was no way he was going to give her even that satisfaction, so when his eyes met hers he let her see him force a bigger smile than before, a fake smile. It was something he had seen in Hollywood a dozen, dozen times. Then he finished his sentence, all possible sincerity gone, "good as well."

He gestured to the other chair at the small table he was sitting at. "Please, join me."

Jack didn't wait for her to sit. He sat back down, and took a sip from his coffee. "It's been awhile. What are you up to these days?"

It took far too long for Jack to look up from his phone. Sophie was used to men jumping to do what she wanted. Even after she’d lost everything else she’d still been able to manipulate men with her looks. Of course, that required said men to be looking at her and right now Jack seemed far too engrossed in his phone to do that.

After what seemed an eternity of waiting for his attention, during which she simply got more frustrated, he eventually turned to her. Then he turned his smile on her and she felt a flash of confidence once more. Things were going to be OK. She’d get back together with him, maybe enjoy his money for a while, then kick him to the curb once she was back on her feet.

Speaking of people on their feet, Jack had stood. While sat the table had concealed the physique that the suit did a poor job of hiding. It had been obvious that the suit was expensive from the counter, but in person it was even more so. Clearly it was tailored, showing off his trim waist, broad shoulders and muscular tone.

Sophie admitted to herself that she would not mind seeing what was under that suit.


She smiled as he started to look her up and down, usually this was where men became more pliable, but her smile froze at the pause and the sudden absence of sincerity in his voice and face.

Bastard.

He even sat before her, and for the first time in the date Sophie realised that maybe she didn’t have the upper hand that she had expected. Not that she had any options left. Forging on, she took the seat he had gestured to. It couldn’t hurt to seem at least a little subservient.

“Oh I’m doing just fine. Keeping myself busy, you know me, I can’t stand to stay still.”

It wasn’t as if she was going to tell him just how desperate she was. She leaned forward a little, not enough to be obvious, but enough to make her cleavage just a little more visible.

“What about you?”

There was a complete shift of attitude now that they were talking. Jack's focus was completely on Sophie now. Granted, it wouldn't look like much from an outsider's perspective. He was leaning back in his chair, at an angle to the table with his legs crossed in the 'manspread' fashion with his right foot resting on his left knee and his shin parallel to the floor. His right hand was on his cup of coffee which was in a constant state of motion, tiny, jittery motions. One could assume it was from the caffeine, but Sophie may remember that Jack was always a bit restless when he was bored.

But from the moment she sat down, his eyes never left hers. Jack was a rapt listener, even if he never looked the part.

He nodded at her comment about keeping busy. He noted that was characteristically odd for the girl he used to know. Sophie was always proud of her work, but this answer was evasive. Strange.

Then she asked him what he was up to. Heh. This was an answer he'd been working on since she'd called.

"You were right, of course, I'm still not taking things seriously. I spend most of my day playing games or reading. My gaming rig is better than the Wal-Mart Black Friday special I had in college, I'll grant you that. I swim for a few hours every day. Not at the Y, but in a private heated pool at any one of my houses. I go to a lot of parties. Last week was Scarlet Johansson's birthday. Her ex-husband Ryan Reynolds was there. I had a wonderful time."

Jack released his coffee and brought his left hand up. There was a PATEK PHILIPPE REF 1518 original wrist watch from 1941 on his wrist. The watch last sold for eleven million dollars. It was the epitome of understated success. There were more expensive watches out there, and most of them looked ridiculous covered in diamonds and other gems. This was just a simple, elegant watch, valued more as a piece of history than for it's intrinsic value. He started winding it with his right hand, casually, as if this was just one more way he kept himself occupied whilst bored, and not a deliberate action to bring attention to his success.

"And in my free time I play the markets a little. Us shiftless layabouts have to do something to keep busy."

It wasn't the most ostentatious display of wealth he could have put on, and there were plenty more names he could have dropped, but Jack wanted to establish that he was over Sophie, that she was completely wrong about him, and that he didn't need her anymore. Even if she was making that outfit work for her.

Sophie didn't have the giant tits and excessive figure of a porn star, but she had a lithe body, tight, and very sexy.

He was fidgeting. Jack only fidgeted when he was bored, and right now he was fidgeting. That was like a slap in the face, and she wondered how much of it was intentional, trying to get a rise from her, and how much of it was subconscious, because he was actually bored. She could only hope it was the former, maybe he really did want to get back with her and was putting on a show of not being interested in an effort to pull her in.

At least he was listening, but then he had always been good at that. She hadn't left him because he had been a bad boyfriend, she'd left him because it had seemed like he didn't have a future. She'd wanted a man with drive, with passion, with something he wanted to do. Jack hadn't had that in college, he'd spent too much time playing on his damn computer and not enough on actually working at achieving something. It was annoyingly ironic that he was the successful one now. Not that he seemed to know about her recent fall from grace.

Of course, he was making no pretences at humility now, mentioning private heated pools and Scarlett Johansson's birthday party were hardly the kind of references that needed to come up in his answer, but they came up anyway. Nor was the clear flashing of the Patek Philippe. Sophie didn't know enough about watches to identify anything beyond that, but she'd moved in high society and knew that it was anything but a cheap watch. He was definitely trying to show off his success. If she hadn't needed him then she would have walked out right then and there, she hoped however that this display of being 'over her' was just that, a display, and that enough time would let her remind him how good he'd had it in college, and convince him to take her back now.

She laughed gently as if he'd told a joke, gently putting a hand on his forearm. "I was young, trust me, I was a lot more judgemental then than I am now."

She acted as if she hadn't already known how successful he was. "I'm glad to hear things are going so well though. You always were a charmer."

Jack started to fume when she laughed at his comment and then put her hand on his. And she called him a charmer?

Charmer? He'd always been a charmer? A charmer? A fucking charmer? What the fuck kind of response was that? A charmer?

There wasn't anything charming in the way he'd spoken to her. Jack was rubbing her nose in his success. He was trying to be a jerk. He could definitely be more obvious about it, but that would cross the line from petty, smarmy jerk to straight out asshole. Right now he was showing her that he was the one that got away, that she should regret breaking up with him in college, and maybe looking to see a little bit of envy in her reactions. He didn't want to cross the line to complete asshole, but her lack of a normal reaction was pissing him off.

Jack closed his eyes and took a deep breath. He let it out slow and looked Sophie back in the eyes. He was studying her face. Why wasn't she getting pissed off?

She must be more successful than he was. That was it, she was an even bigger success and wanted to rub his nose in it.

No, that didn't make sense. If she was a bigger success she never would have called him. She would have continued on in her existence, never wasting a second thinking about an old boyfriend. Besides, as nice as her outfit was, and as much as she made it work for her body type, and she fucking made it work, it wasn't nearly as nice as his bespoke suit. She was not a bigger success.

No. She wanted something. He knew that from the start. He'd figured she wanted to get back together, which was why he was rubbing her nose in his success to begin with. She couldn't possibly think he was interested in her after that contemptuous display, could she?

No. She wanted money. She must have already known he'd made good, so the ostentatious display wasn't a turn off, it was playing right into her hands.

Jack sighed, pulling his hand away from hers and then took a sip of coffee.

"Alright Sophie, you called me. How much, I mean, what is it you want?"

Sophie didn't quite frown, but she was certainly discomforted as Jack closed his eyes and breathed in deeply. They'd both changed a lot since college, but she wasn't stupid, and she could tell when a man was trying, and failing, to control his temper.

He was studying her intensely, like he was looking for something and she smiled uncertainly. She was feeling uncomfortable now, on the spot. It was a little like being interrogated, even though he wasn't speaking. She tried not to give too much away, maybe if he saw whatever he was looking for he would calm down. Either way she needed this.

Then he pulled his hand away, and she knew for sure that her chance was gone. Nonetheless, she tried to regain what was left of her shattered pride. "What are you talking about Jack? I just wanted to reconnect…"

She was pretty sure he wasn't buying it. She searched his face, looking for something in it that she could use. She knew that she was still attractive, and she'd even seen that in his face, but right now there was no weakness there, nothing that she could exploit. It was cold and passionless.

Sophie attempted to hold her nerve, she'd once been so comfortable doing that, it had thrilled her, staring down a board of directors. Right now, with this man standing between her and financial ruin, she couldn't find any thrill in it.

Her nerve snapped, and her hand leapt out to stop him pulling away. "Look Jack. Please. I know I was a bitch. I know I was wrong, so wrong. But I'm desperate. I need your help."

So much for playing it cool.