As expected, Matthew woke up the next morning to FuckYouMoney’s brand-new video and spent half an hour raining compliments and cash down on his boss while his dick throbbed at the memory of using her. Watching her getting railed by him in the darkened restaurant was hot, even with their faces blurred, and he alternated his praise with questions about how it felt to cross so many lines, but Mandy kept it upbeat and focused on the great time she had. There wasn’t any way for him to be sure that her compliments were real or if she was just praising him to make her customer happy, but he appreciated being called “a pornstar in disguise” just the same.

Once that was done, he opened his book and asked, “Well - what are we doing next, Tome?”

‘That’s entirely up to you, my Master. You have all the options in the world. “Your neighbor. Your teacher. The woman who sold you the ticket. Even your boss if you would like to play with her again. And, of course, if none of those options appeal to you, we can certainly find you someone new to play with.’

The options made his head swim as he tried to decide which one he was in the mood for and found that he wasn’t sure. Could one have so much sex they started to get tired of it, he wondered? At that moment, Mandy’s words came unbidden to his mind again, ‘What does it feel like to get off on paying women to do screwed-up things they don’t really want to do,’ and he shook his head to clear them. 

“I don’t know - I don’t think Mandy needs any more money right now. Maybe we should focus less on women and more on how to make my jackpot grow instead.”

‘I never said you would have to pay her Master. Just be your charming self, and you’ll have lots of opportunities this week. Once the ice is broken so spectacularly, encore performances are often more than welcome.’

“Wait, are you saying she’ll actually want to fuck…” His words trailed off as he considered the implications of her words. “Nevermind. You know what. I don’t want to know. I want it to be a surprise.”

Matthew looked up at the time and decided to reluctantly put the book aside. He needed to get dressed in his uniform. They could talk about making more money afterward. After all - it wasn’t like he had to do this much longer. Only three more shifts, and he’d be unemployed, and he could spend his days doing something else. Quitting now would probably be for the best, but he wasn’t willing to give up his time with his hot-ass boss just yet. 

He was still a little hard when he went to work, though he wasn’t sure if that was because of Tomé’s cryptic hint or the memory of bending his boss over the counter five feet from where he was standing. On the way over, he’d wondered if what had happened would make things awkward between him and his boss, but everything seemed to be back to normal, at least until she pulled him into her office after he had taken a little too long on his break. 

“What’s the point of punching in and out if you aren’t going to do it properly,” she demanded as she closed the door behind him, letting his coworkers know that he was going to get raked over the coals again. 

He wasn’t, though. As soon as the door closed, she deflated and said, “Don’t worry - I’m just making things look good for when I fire you on Friday. I don’t want it to seem too sudden.”

There was a spark of lust in her eyes, though, and when they momentarily flicked down to the bulge in his pants, he knew there was an opportunity here. Normally he would never have had the balls to do what he was about to do, but between the way she was looking at him and the way he was feeling about her still, he leaned forward and kissed her hard enough to silence whatever she was about to say next. 

Their tongues danced for almost half a minute before she broke the kiss and hissed, “Christ, Matt - what do you think you’re doing? The door isn’t even locked.”

“Like I could help myself when you look at me like that, Mandy,” he answered, trying to sound casual. That made her blush a little bit as she realized she’d been caught. 

“Look - it was a one-time thing. As much as I loved it, doing it again would be a terrible idea, you know?” Mandy’s mouth might have been saying no, but he noticed her body hadn’t tried to move away from him at all, so he figured there was a much larger part of her that wanted to say yes. 

“I’m still working here for the rest of the week,” he whispered, squeezing her left breast hard enough that she had to bite her lip to keep from moaning, “and the way that you came on my cock, you don’t strike me as the sort of woman that likes to do anything that she enjoys just once…”

Mandy swallowed hard, but her only response was to blush, and when he smiled a little wider, she leaned in and kissed him again, giving him ample opportunity to slide his hand down her pants and finger her pussy just long enough to find out that she was soaking her way through her panties before she squeezed her thighs shut to stop him. 

“Not now,” she hissed. “After work, but only if this time you actually bring some fucking condoms. I’ll text you to let you know when to show up, alright? Now try to behave yourself before everyone finds out.”

“Yes, ma’am,” Matthew said, carefully putting his smile away and acting like he’d been appropriately chastised. He spent the rest of his shift wondering if he could have pushed things further and tried to decide whether she’d really call, but he bought some magnum condoms on his way home just in case. 

He tried to ignore his dick throbbing in his pants, but after he noticed Mrs. Hale in her backyard sunbathing again, he decided that was going to be impossible. He looked at his phone and saw he still had some time before her kids got home, so he decided that he might as well go over and say hello and see if he could talk her into relieving his aching balls. 

. . .

It was after midnight when Matthew finally had a chance to lie down. He’d spent the afternoon fucking his neighbor hard enough to make her scream, and then as soon as he’d gotten home, he had to shower because he had a new text message from his boss telling him to wait until hers was the only car in the parking lot, and then to come over around 11:30. He’d cum on both women’s faces of course, but only after he’d told them how much he loved the feeling of their pussies when they were coming on his cock. He was surprised at how many of the same lines he’d used honestly, but it wasn’t exactly lying, and they both ate it up, so he didn’t see the harm. 

That’s how the rest of the week played out for him. Every day he wasn’t fired, yet he flirted with his boss, he fucked his neighbor, and then at night, he came over and fucked his boss again. It was only on the final night, when she told him that this was fun, but they couldn’t keep doing this, that he stopped by the convenience store to start laying the groundwork for another night with Jane. She was obviously annoyed that it had taken so long for him to come back, but she’d still said yes; she’d just picked a date a couple days from now to make him wait like he’d made her wait. 

Later was all he could handle right now anyway, though, so he was fine with that. If he’d wanted her right now, he was sure Tomé could have told him some trick to make it happen, but Matthew was completely and utterly exhausted. Every last inch of him was tapped out, especially the eight inches that mattered most. He’d cum over a dozen times in the last few days, and he wasn’t sure he could get it up again if he tried today. 

As he lay on his bed exhausted, he realized he really hadn’t done anything but fuck all week. He was no closer to a plan on what he should do next, and he was sure if he kept this up, his grades would start to slip, but right now, he couldn’t make himself care because every last one of those was a tomorrow problem.