In the end, it was a simple plan, and the pieces were already falling into place nicely. He probably could have finalized it already if he had all the information to use his brand-new LLC’s corporate accounts, but that was still a few days away. As it was, he wasn’t in any hurry, though. He was having far too much fun stringing her along with a tip here and a flirtation there to want to rush to the end too quickly. 

The fact that the whole thing was his little secret made it hard to stop smiling while he was at work. Mandy would never give Matthew the time of day, but FuckYouMoney, she’d drop everything she was doing to answer those messages. He was under no illusions that they were always accompanied by $20-$100 tips just to make sure he didn’t lose her interest, of course, but it was still a fun game to play, especially while she was at work. 

He would invariably time his messages like, ‘Here’s a hundred dollars to show me your cunt, cunt. Don’t take all day either because I need something to jerk off to in the worst way.’

At first, she’d tried to put off tasks like that until she was home, but after her very generous patron had almost ghosted her, she was much more obedient. Now she’d drop everything she was doing and disappear into her office or the restroom to take a few cute pictures and send them to him. Of course, he couldn’t check them until he was on break, but the fact that he was leading his bitchy boss around by the nose like this made it impossible for him to have a bad day, no matter how much she yelled at him.  

How could you be mad at someone when they were spreading their lips for you and sending you shots of their pretty little pussy while telling you how wet you made them?

He always thought she’d get suspicious that FuckYouMoney’s periods of quiet always seemed to line up with his scheduled work shifts, but Mandy never seemed to put two and two together. Why would she? Anyone that was slinging burgers out of a drive-through window could never afford to be lavishing her with cash like this. 

It was in those private chats he felt like he was finally starting to get to know her for the first time. He’d always thought of Mandy as kind of a prude, but if even half of what she said to him in private was true, then she was a complete slut. She was in an open, poly relationship with a girlfriend she’d never mentioned, and most of their trips together ended in a three-way with some hot stranger. 

Just the image of that moment made his dick throb. The way she described it, their last anonymous lover had been a hot Spanish guy, and she’d ridden his cock while her unnamed lover had ridden his face until the ecstasy had worn off. After that, all he wanted to do was jerk off, but he knew that Tomé didn’t like it when he did that, so he forced himself to hold off, letting his desire build day by day. 

It wasn’t until he made the idle quip one day, ‘It sounds like you’d fuck anyone in the right circumstances.’

‘Probably, hehe 🙂’ she answered. ‘Especially on vacation. I might even fuck you if the mood was right.’

He knew she was saying it just to get more money out of him, but the moment still resonated. ‘Right now, I prefer to admire you from a distance. It’s sexier that way. I’ve got plenty of local pussy if the urge strikes.’

‘Yes, Daddy,’ she said, sending him another picture of her perfect tits. ‘You know I want to please you however I can.’

‘Oh?’ he asked. ‘I can get pretty kinky. You might not have what it takes to earn real money from me.’

‘I’ll do whatever it takes for those kinds of opportunities, Daddy. For the right price, I can even make my girlfriend join me. I’m a people pleaser.’

‘Why would I need to pay you to have sex with your girlfriend? You do that all the time for free,’ he asked.

‘But you wouldn’t be paying for me to do it - you’d be paying to watch me do it. I got a couple hot videos I can send you privately if that’s your thing. She’d kill me if she ever found out, but for just a couple hundred dollars… well, I’m sure you’d keep my secret.’ She was pretty bold about selling herself, but Matthew was sure that it was all part of the act. 

‘Oh, I’ll definitely be buying those, but a couple hundred bucks isn’t real money, is it?’ Matthew asked, returning to his original point. The truth was he’d love to see Mandy cum in another girl’s mouth, but he wouldn’t let himself be distracted. The important thing wasn’t watching her cum after all; it was watching her cum on his dick. ‘Tell me - you said you’re a manager - have you ever fucked one of your employees?’

‘I try not to mix business with pleasure,’ she answered after a small delay. It wasn’t a yes, but it wasn’t a no, either. 

‘Interesting, but that’s hardly a no. Tell me about your worst employee. Are there any guys that work for you that you’re just looking for an excuse to fire?’

‘There’s this guy,’ she said, sending him a picture of himself with a blurred-out face. ‘He’s always late, and he checks out my breasts whenever he thinks I’m not looking. TBH, he’s kind of a creep.’

‘And fucking a creep - it doesn’t come cheap, I imagine?’ he asked. This was the moment of truth. He didn’t have the luxury of being offended. He just had to play the rich old pervert that got off on making a young woman do something she normally never would for cash. 

‘Wait - you want me to fuck him? Why?’ she asked.

‘Why not. You seem to think that I’m just a guy that wants to get into your panties.’ Matthew answered deliberately and slowly. ‘There’s plenty of cheap college pussy in my town. The reason I find money-hungry young women like you so interesting is because I’m curious how far you’ll go to get it. If you’re not interested, then say so. No skin off my back.’

The message was read immediately, but silence stretched on the line for almost ten minutes before she responded. It gave Matthew time to worry that he’d pushed her too hard, 

‘How much money are we talking about here?’ she asked finally, making him smile. 

‘For a video of you fucking your least favorite employee? Name your price,’ he responded, genuinely curious what she would come up with. 

He’d be willing to go up to $10,000. That was an impossible sum for something like this, of course. He’d already decided that in advance, but at this moment, the more interesting question was how much she thought it was worth. 

‘$5,000?’ was the number she eventually came back with almost a minute later. 

“See - you could have been even greedier,” Matthew chastised her through the phone screen before picking it back up. 

‘Sound good to me. I’ll pay $6,000 if you actually fuck him at work too. That would be even hotter.’

‘How could I ever face him again if I ever did that, though? 😭’ She shot back almost immediately. Again, that wasn’t a no, and that made him smile. This really might work. 

‘Tell him you were going to fire him anyway, and you wanted to give him a little severance package since you’ll probably never see him again. I mean - I’d take that deal if it was me.’ Matthew chuckled as he sent the last one. To him, that joke was funny, but no one else would ever get it. 

‘I’ll think about it,’ she said finally, leaving him wondering if she was really going to go through with it. 

It wasn’t until the next morning he woke up with the message, ‘What does it feel like to get off on paying women to do screwed-up things they don’t really want to do?’

It had been sent in the middle of the night, which to him meant she’d been drinking, and a few hours later, when he went to respond, she’d deleted it, obviously worried she was going to scare away her benefactor. Instead, her new message read, ‘You send the money, and I’ll start seducing that loser all on camera for you, Daddy 😜’

That made him smile, at least, but he didn’t stop thinking about her first message. Those words haunted him the rest of the day. Up until now, he’d never given a second thought to using the secrets Tomé gave him to get what he wanted before, but this made him pause. He’d explicitly turned down her offers to brainwash people and make them irresistibly attracted to him, but for the rest of the day, he couldn’t help but think he was doing something wrong even though he was sure that he wasn’t.

Author's Note: I have finished volume 1 of this story (31 chapters). Sometime later this summer, after I have started posting on Angel Fall again, I will start on volume 2. So, this will post weekly for the next 8 weeks, but if you are feeling impatient you can go read the whole thing on my Patron right now!