the boss

JACKSON ROSSETT TWENTY-EIGHT

[jacksonrossett]

night changes

[wtvrdrew-blog]

“Maybe we both shouldn’t be so defensive. Maybe then we won’t be at each other’s throats so much.” Drew suggested and shrugged. He wasn’t sure how Jackson would react to that - part of him believed it would only piss him off further. Why would Jackson want to be less defensive around him? Him agreeing would be a surprise. He nodded, smiling a little. “I know I’m an asshole most of the time but I never meant it to… hurt your feelings.” He spoke carefully, not wanting to annoy Jackson again. He couldn’t help but let his smile get a little bigger. “I am. Not happy about the way I got you to confess to that but I’m happy.” He bit his lip for a moment. “I’m desperate for you too, by the way. And not just for your money, before you think that.” He blushed at his confession. Normally, he would have played it off as that but right now, it seemed more appropriate to admit the truth - though Drew would deny that it was. “I’m not crying.” he repeated, more forcefully this time. He scoffed at his words but it came out somewhat broken. There was no point in denying it any more. “Contrary to what’s currently happening, I’m not that fragile.” he said, pulling back a little to look at him. “Sure, I’d have been pissed but I would have understood if you didn’t do it.” He lifted a hand, not quite sure what his intent was before he put it against Jackson’s chest. “You like to say you’re bad at this normal people stuff and that it’s not what you’re used to, or whatever but…” He half shrugged. “You’re not as bad as you think you are.”

“Couples of day.” he echoed, slowly nodding. Again, that wasn’t ideal but Drew knew they couldn’t do this forever, that was ridiculous. Looking at him, Drew guessed that Jackson wouldn’t be too bothered by his departure. He’d be fine with that. Probably. Drew shrugged, he was trying his best not to be upset with that. In hindsight, doing this was probably a mistake on his part but it was too late to back now. He’d just have to remind himself of what he’d been told - there was no room for love, there was probably no room for another other emotions besides a handful. He could deal with that, he’d force himself to deal with that. “I don’t want you to go slow on a compromise like that.” he said. “I’m not paying you to fuck me, it’s the other way around. So don’t compromise for me. If slow’s not your thing, it’s not your thing.” He shrugged then added, “I like it rough anyway, so it’s fine.” He turned his head away from Jackson, a bitter expression on his face. He may have basically admitted to being jealous but that didn’t mean he liked it being pointed out to him. He’d never felt such intense jealousy before but he’d never been with anyone like Jackson before - this was different. “So what?” he muttered. “I’m allowed to be, okay?” He took in a deep breath, leaning into his touch. “There’s more than one pizza place. They’re probably better than that one.” He frowned at the mention of a discount, shaking his head. “Get your stupid discount if you want, he won’t be as good as me.” He muttered the last part, a little shocked at his own vanity. A shaky breath left his lips and he pressed against Jackson, his body heating up with desire. “Aren’t you lucky that I’m eager to please you , huh?” Pulling Jackson’s hands off of him, he pushed him back towards the chair. “I’ll show you why you choose me and not him.”

[jacksonrossett]

Jackson matched his shrug. “I guess.” He said, glancing away. Was he that defensive? He just didn’t want him second guessing him or coming for him. “I don’t like fighting you. I’ll... try to be less defensive.” Jackson bit at his lip, finally looking back at Drew. “I hope you weren’t, that wouldn’t be very nice of you.” He teased, rolling his eyes. “Next time you’re an asshole I’ll just spank you.” And he meant it, he’d just give into his wants and pull him over a table or his knee. “Except you’d probably like it so much you’d be a constant ass.” Drew’s smile only made Jackson feel a bit more embarrassed about his confession. “Stop smiling so wide, you’re going to blind me.” He was glad that Drew was happy, but Jackson wasn’t thrilled that he admitted it. “Not just for-” Jackson paused, a playful smirk on his lips as he admired the blush on Drew’s cheeks. “It’s my dick, eh?” He was trying to be more... fun, playful. He wasn’t sure if he was succeeding or not, but he didn’t want to think that there was any way, shape, or form, that Drew would ever develop feelings for him. “You’re not crying, I get it.” Jackson eyed him, still not 100% believing him. “I know you’re not fragile, but I...” Pausing, he wasn’t sure why he was trying to defend himself when it comes to caring. He wished Drew hadn’t pulled away, he almost reached forward to pull him back. “I want to do what’s best for you, though, always.” Was that so bad? “I-I’m trying.” Looking down at Drew’s hand on his chest, he relaxed some. 

Jackson didn’t want Drew to already think about leaving, but it was his choice. “You might need a new car, or a fancy new game system. Maybe a Masters program.” He’d shell out the cash, most likely- trying not to get too ahead of himself. “Or we could fuck for free, if you like it so much.” Jackson joked, shaking his head, knowing Drew would never go for that. “Sex for vacations. Still up for Italy next week, baby?” He was eager to take him abroad, especially after his excitement about it. “Good, I’m glad you like how I fuck you. But I am an old man, I might need to slow down. Sometimes it’s good to go slow, fuck you deeper and harder.” He felt harder already, just thinking about it. “I’ll fuck you however I want, better? I’m sure you’ll love it however I give it to you.” His hands wanted to explore him, Jackson’s mind was buzzing with excitement. It was hard not to be around Drew, he was gorgeous and the last time they were together he had the best sex of his life. It would only get better once they learned more about what each other like. “You’re more than welcome to be jealous. It’s hot.” He admitted, reaching up he traced Drew’s cheek. “You can make me pizza then, since you crave it so much. We’re going to run out of shops until we find one purely run by women. Trust me, baby, no one is as good as you.” His jealously was making his chest thump in his chest, he was surprised by how much he genuinely enjoyed it. Jackson lost his breath for a moment, Drew pressed against him. “Fuck.” He breathed, letting Drew lead him back on the chair. Sitting back, he loosened his tie and watched up at him. “I’ve been waiting for this for a long time now, baby. Show daddy how much you want him.” He wanted to touch him, pull him down on him- but he let Drew do what he wanted. Parting his legs, he watched up at him, his eyes burning with desire.

[jacksonrossett]

night changes

[jacksonrossett]

wtvrdrew:

Drew remained silent, crossing his arms. He looked at him for a few moments before he shrugged, looking down. “I don’t mean any of that. It’s just - just sarcasm. I do respect you. Sarcasm is my method of self defence, okay? That’s why I told you to not take everything so personally.” He dropped his arms to his sides but he still couldn’t properly look at him. “And maybe I think it’s a good thing that you’re desperate. Because people like you aren’t desperate for people like me.” He quickly wiped at his eyes, he didn’t want to cry, he didn’t want to come off as weak. “I’ll stop, okay? I’m sorry I hurt your feelings, I never intended to. I’m just used to my friends being able to understand what I’m saying.” Drew frowned when Jackson pulled him close, it was unexpected and it took him a moment or two to respond. In the end, he chuckled at what Jackson said but it was short lived. “I’m not crying.” but he had definitely teared up. “This is - This is fine.” He muttered. “But -” He slowly wrapped his arms around Jackson’s waist, maybe a little too tightly. “This is what you do. Or one of the things you can do. Another is act like they’re not crying, which would have been better in this situation.” He paused, letting out a soft breath. “Thanks.”

Drew nodded. That seemed right. Not ideal but right. He didn’t offer any input while Jackson spoke until he heard something that caught his attention. It was up to him when it ended, when he stopped needing money then it would end. What if he acted is if he always needed money? But why would he do that? That didn’t make sense and he almost frowned at his own thoughts until he remembered he wasn’t alone. “That sounds ideal.” He muttered. “Should I let you know in advance if I ever stop needing money?” Drew resisted the urge to roll his eyes again. He didn’t expect them to ever take things slow now - nevermind make love. “I think, with all the animosity between us, there wouldn’t be any room for love anyway. So yeah, no making love.” He then smirked. “But we can see about the table.” Hearing Jackson’s voice, he remained silent, annoyed that his jealousy was so obvious. He turned his head away when Jackson kissed him, knowing that he was acting like a huffy child but he didn’t care. “I’m not jealous.” He spat out but even Drew didn’t believe his own words. It was evident in his voice that he was and there was no point in hiding it, not if they both knew. “I just don’t like that he showed up here.” he muttered. He knew it didn’t happen on purpose, it was just a coincidence but that didn’t matter to him. He was being selfish. “Make sure he doesn’t show up here again.” He finally turned his head to look at Jackson. “Even when I’m not here.” Drew let out a sigh. He had to relax, it was clearly no big deal. “No. Voyeurism isn’t my thing.” Shifting in Jackson’s arms, he leaned over to kiss him, with a little too much force. “What I want you to do is eat this dumb pizza with me and then let me ride you like a racehorse.”

“And my method of defense is power and coldness.” Jackson breathed, trying to take in all the information he already knew but refused to use in practice. He blinked at him, a bit blindsided by his honesty. Is that how he really felt? “So it wasn’t meant as a way to be an asshole?” Jackson was honestly desperate for Drew, in a sexual way- and maybe in a companion way as well. As much as he pissed Jackson off, he also made him think and hold his tongue more. He wasn’t used to people like Drew in his life. “I-I’m desperate for you. Happy?” He felt like it was some weird childhood love confession, which it wasn’t. He hated watching Drew behave like this, he wasn’t so... Cry-y before. “Just... Think about how someone new would react.” Jackson shrugged, watching him closely. “You might be crying. Please don’t cry.” He repeated, looking away and ran a hand through his hair. Feeling him wrap around his waist, he finally looked back at the boy. “If I reacted any other way you’d be more upset. I need to comfort you.” Need. He didn’t need to do anything, but he choose that word anyways- in fact it just popped out. With Drew holding on to him, he felt a bit more needed- secure. “You’re welcome.” He mumbled, still a bit horrified at his sudden declaration of need. Maybe they’d understand each other more, he hoped so. 

Jackson didn’t like the pause, Drew was thinking- and he was more anxious of what he was thinking. What was he thinking about? But once he spoke up, agreeing, Jackson relaxed visibly. “Ideal.” He repeated, nodding. “You don’t have to. But, I’d prefer it.” He honestly wasn’t sure what he’d do, what kind of time he’d need. Would he be sad? “Just a couple days or so.” Couple weeks, couple eternities. He just would need time to find someone else to fill the void, probably left just a bit bigger than when Drew arrived. What was he thinking? “Or so.” He repeated softly, shaking his head. “No room for love. You learn fast.” Jackson chuckled, biting his lip afterwards. “Maybe you’ll get lucky one night and I’ll be tired so I’ll go slow. Tell you how... Handsome you are? Sexy?” He wasn’t good at romance, he wasn’t even knowing why he’d even suggest he’d remotely try. Silently he wondered if Drew noticed him trying, not wanting to upset him. How did someone so emotional with love end up in a line of business like this? Sure he needed the money, but he didn’t want to destroy him. “Some is jealous.” He liked it, it was a new feeling really. Sure he had people be jealous before, but not in a way that it actually made him feel good. “You’re desperate for me.” He made the connection, smiling slyly. The realization sparked an excitement in him, he was jealous. “What if I want pizza? I could get a discount.” Jackson teased, his hand sneaking up Drew’s shirty, rubbing circles into his hips. “I won’t ask for him. I won’t order from them again. In fact, I won’t even eat from them now.” Leaning down, he pressed kisses to Drew’s neck slowly. “I’d like to see you ride me like a racehorse, baby.” Nipping at his neck, he brought Drew’s hips to his own in a strong motion. “You can take the pizza home to Sam later.” Jackson breathed, his hands moving to Drew’s ass to squeeze. 

[jacksonrossett]

night changes

[wtvrdrew-blog]

“You actually pay me to be loud, last time I checked.” He stared at Jackson in shock for a moment before he shrugged. “I just wanted to know. Like, we’ve only known each other for a few days and I didn’t know if you would care that much this early one.” He sighed, looking away from him. “I didn’t joke about you wanting me dead, I made a joke about the ways people keep others silent. And yeah, it is! What did a panda ever do to you?” Drew tried not to let his words get to him but he couldn’t help but feel upset, hurt, by what he said. He looked away fully from Jackson, not wanting him to see the hurt that was so obvious in his eyes. “I’m easy?” he asked, stopping when his voice wavered. “If your plan in saying what you just did was to upset me then you’ve succeeded.” He covered his eyes with one hand for a few moments. He wasn’t going to cry. This was the stupidest thing to get upset over and he was definitely not going to cry. “What’s next? Are you going to call me overbearing? Huh? You may as well cause you implied it.” He turned away from him, still not wanting him to see how worked up he had gotten. “I’m sorry I’m not some soft spoken, timid thing that you would obviously find much easier to control. I know that would be easier for you if I was but I’m not about to fake something just cause it would be easier on you. If that’s the kind of person you want then I’ll leave. Give me the word and I’ll leave.”

“Of course I like it. It’s hot.” He nodded, slowly. Drew had purposefully chosen not to think about what would happen once he had everything he needed. Would it really be that easy to break things off with Jackson? They’d been intimate and they were going to be intimate a few more times - Drew wasn’t sure if he could just let that go as if it were nothing. “Yeah, that sounds okay.” Drew nodded, sensing his annoyance and wanting to stifle it before anything broke out - it seemed as if they were a terrible combination together. They would have to work on that. “Okay. You don’t have any other motives. I’m sorry for thinking that.” Drew rolled his eyes. What other answer had he had expected? He’d gotten too optimistic in what he was saying. “I guess that throws making love out of the window.” he joked then met Jackson’s eyes. “That was a joke by the way, making love actually requires being in love and that’s never gonna happen for us, don’t take it to heart, yeah?” Drew smirked, not believing Jackson’s words. Someone as possessive as him would no doubt get jealous, it would only be a matter of time. “Okay. Whatever you say.” He raised an eyebrow, about to make a comment on the boner thing when he heard the door. He watched as Jackson headed to the door before he sat down, crossing his legs and waited for him to return. Hearing talking that definitely didn’t sound like the usual conversation that proceeded a pizza delivery, Drew listened in, his breath getting stuck in his throat when he heard what was being said. He wasn’t jealous, there was no way he would be jealous of some stranger but that didn’t explain what he was suddenly feeling. It was a mixture of jealousy and hurt but Drew knew he had no right to feel that way. It wasn’t as if they were in a relationship, so it shouldn’t have effected him as if they were dating. He flinched slightly when he heard Jackson’s voice and he hoped he didn’t look like he’d been eavesdropping but he had a sinking feeling that it was obvious. “Okay.” He muttered, not really sure what he was answering. Looking down at the pizza boxes, he found that he’d lost his appetite. Shutting his eyes, he let out a soft breath, part of him regretting coming over.

[jacksonrossett]

Rubbing his hands over his face, Jackson took a deep breath. He felt like he needed a DVR with this guy, just time to pause and think before reacting. “You’re not easy in the sense that you’re thinking. You’re easy as in you come here and there’s no pressure or anything.” Maybe easy wasn’t the word he was looking for. Dealing with Drew was the complete opposite of how Jackson dealt with people on a daily basis. “I’m not trying to upset you.” He said, his whole body panicking at the sight of Drew in front of him. He couldn’t have him crying, fuck. “Baby.” Jackson said softly, trying to think of what a normal person did when someone was crying. Jackson didn’t deal with people crying, ever. “Drew, stop, I’m sorry okay?” Holy shit, this was getting way too emotional too quickly for him to handle. What would Drew want? “I don’t want you to leave. I want you to listen to me. I want respect from you- you fucking call me desperate and talk about how I can’t get laid without paying someone. How do you expect me to act? Shower you with kisses?” Jackson was lost for words. Drew could dish it out, but he couldn’t take it- but Jackson wasn’t going to take it either. “You can’t be rude to someone and expect them to just take it, especially not in the kind of relationship we’re in. Just, please- stop.” Jackson grabbed his arm and turned him around, pulling him into his chest. “Don’t cry, I don’t know what to do when people cry.” 

Smirking, Jackson enjoyed the fact that Drew thought his traits were hot. “Good, I think it’s very hot when you let me take control.” Jackson’s eyes searched Drew’s face, trying to pick up on what he was feeling. He was still new to this, he couldn’t really afford to land on anymore hidden bombs. “That’s what people usually do.” Jackson shrugged. “I just assumed you’d want to move along to someone else. For me, I don’t really care when it ends.” He paused, shaking his head. “No, no I take that back. It matters to me when it ends. The ending is more on your part, if you need money then I have it. Once you stop needing it and want to go back to normalcy is when it will end. Like most aspects of this, it’s really up to you.” Jackson couldn’t help but frown, making love was some made up concept for people who were too tired and delusional to actually fuck. “Making love isn’t on the table. But I could fuck you on the table.” He teased, trying to not focus too much on it. Making his way to his room, he contemplated jacking off, but decided against it- that’s what Drew was for. Instead he simply changed into a wifebeater and some sweatpants, more comfortable. Walking back towards the living room, he paused to look at Drew. Something was off, he knew that. “You’re overthinking, baby.” He said softly, walking to him and wrapping his arms around Drew’s waist. “I met Alex before you.” Jackson pressed a kiss behind Drew’s ear. “He was a companion for one of my partners. When I was going through the process, their contract was ending so my partner recommended me him. The kid gave me his number, but I never called. Instead you showed up in my office all doe eyed.” It was kind of nice to see Drew a bit jealous, he knew he had been listening in- which is why he kept their conversation so short. “Are you jealous, baby?” He teased, nipping at Drew’s ear. Jackson liked this feeling, he felt wanted in some way. “Want me to call him back? I’ll fuck you in front of him. No one is better than my baby.”

[jacksonrossett]

night changes

[jacksonrossett]

wtvrdrew:

“I don’t think that’s how it works.” Drew shook his head, glancing to his hands. “I just meant it in the way that some rich dudes have to pay their mistresses or whatever to be quiet about them, you wouldn’t have to do that if they were dead. I wasn’t being serious anyway, chill.” He bit his lip, feeling a question nagging at him. “Would you care if I died?” Drew grimaced and crossed his arms, showing Jackson his clear distaste. “There’s jokes and then there’s that. I like pandas, Jackson.” He huffed, uncrossing his arms to poke at his chest. “I don’t want you eating them, okay?” He scoffed, going back to crossing his arms. “I might be the horny 12 year old but at least I can get action without paying for it.” Drew frowned. He was pretty sure he was misunderstanding what he was saying to him but he decided to play dumb. “I can’t fake it? Girls can fake it but that’s only because guys really aren’t that good when it comes to getting them off but like… guys can’t fake it? I don’t see why I would fake anything, anyway. It’s not like this relationship is a normal one. You’re not exactly going to leave me for the same reasons my exes have. And I ain’t gonna leave you cause you’re crabby almost every time that I’ve seen you. There’s no reason to be fake with each other.” Drew smirked, raising an eyebrow. “Why don’t you buy me a pony, daddy? that way you can watch me ride something all the time.”

“Stop it.” He muttered but made no move to actually do anything to stop him. If that’s what Jackson wanted to do then he’d let him - Drew kind of liked it anyway. “Oh, really? That’s a shame, there’s so many attractive people in your building, all that wasted potential all because you can’t bear to see me with someone else. Yikes, possessive much?” Looking at Jackson, he just nodded. He highly doubted that tuition would make much of an impact on his back account but if Jackson wasn’t going to say it, then neither was he. “And once your done paying that? We just part ways as unlikely friends?” Drew rolled his eyes, biting down on his tongue to suppress the groan that threatened to pass his lips. “You wanna start calling me Andrew now? Cause you sure as hell sound like my dad.” Sighing, he “Look, I have it under control, alright? I do my homework, I was just a bit distracted today, okay?” Drew had no idea how this kept happening. They’d only spoken once before yet it seemed as if they always ended up turning the conversation sour. “I just assumed they were, okay? It’s hard not to think all of your motives are sexual or selfish when you’re literally paying me for sex.” Taking a deep breath, he put his hands on Jackson’s shoulders. “Relax. You get so worked up over the smallest of things, don’t take everything I say so personally, alright?” Drew did his best to hide his hurt at what Jackson said. He shouldn’t have expected him to want him to stay over, not after what happened last time. “Of course you didn’t.” Drew rolled his eyes, allowing Jackson to kiss him and he softly kissed back before he pulled away slightly. “What if I want you to take it slow, huh? It doesn’t always have to be rough, you know” He continued to press soft kisses to his neck, nipping at the skin lightly while he hummed in agreement to what was being said. As soon as he heard his friend’s name, however, he pulled back completely. “Are you jealous? Seriously? Of Sam?” Shaking, he shifted so that his knees where on either side of Jackson’s legs and he wrapped his arms around his neck. “Don’t lie to me. You’re desperate. I’m desperate. But if you want to play the waiting game then that’s fine with me. I’m not the one with a boner right now.”

“In a way I already pay you to be quiet, baby.” Jackson teased, shaking his head. They seemed to be already fucking up their understandings of each other, so he just dropped it out of frustration. “Of course I would care if you died, what kind of question is that?” Jackson hated when Drew frowned on him, especially when it was misunderstood. “You need to relax.” He grumbled, his hands going into his pockets as he looked away. “So you can joke about me wanting you dead to keep you silent, but joking about eating pandas is going too far?” He’s never hated pandas so much in his life. It was a slap across the face from Drew’s words that made Jackson take a step away from him. “I could fuck anyone I want, lets make that clear. You are easy, you are clean. You’re aware there’s no strings attached and I’m willing to help you pay for things. That’s the only reason you’re here and any other person isn’t, and trust me there are hundreds of willing boys. Why are you acting like this? I have been nothing but nice to you since you walked through that door.” Drew was lucky as far as Jackson was concerned. He was getting angry at the fact he was becoming a brat and being completely out of line. “If you want me to continue paying you, maybe you should watch your tongue. Maybe you should start faking it, your personality is unbearable sometimes.” He sneered, suddenly wondering why he even had called Drew in the first place. How could he miss such a brat? 

“When it comes to my business, I’m very possessive and controlling. But I recall you liking that.” Jackson gave him one last squeeze before pulling away. He honestly wasn’t sure about what would happen once Drew got everything he wanted. “I just figured that’d be the case. You’d go on to do whatever your next step is and I’d move on.” This wasn’t exactly a long term thing. It would be a while though until everything was paid for, so why worry now? Jackson just started ignoring the annoyance that was coming from Drew, just so he’d avoid his own annoyance growing. His fingers started tapping against the arms of the chair, trying to contain himself. “I won’t have any other motives then. You have everything under control.” His voice was calm and cool, but he remembered that he wasn’t supposed to care. He didn’t want to care, but it only hurt when he realized he did and Drew rejected it. Jackson shrugged off Drew’s hands, glancing away. Maybe he should just fuck him and send him home. “I don’t take it slow, so no. I only do it the way I want to. Why would I pay you and fuck you the way you want? That’s not how this works.” His eyes closed to focus on Drew’s lips, his hands going to Drew’s hips. But once he pulled away, Jackson frowned. “I already told you, I will never be jealous.” Especially not for someone he had to pay to have their company. Jackson’s hands moved down to grip Drew’s ass, looking up at him on top. “I’m not some kid who needs to tend to a boner every time they get one.” He was somewhat glad that Drew was desperate for him- well, hopefully for him. The door buzzed and Jackson groaned, gently pushing Drew off of him so he could go to the door. Opening it there was a young guy with the pizzas, who instantly paused once seeing him. “Mr. Rossett.” He bit his lip as Jackson took the pizzas, his eyes darting down to see the Jackson’s prominent boner. “Alex, I didn’t know you worked here.” Jackson kept level headed, a content smile on his face. “You never called I thought that-” The boy paused and narrowed his eyes, seeing Drew. “Here’s your tip.” Jackson smirked, handing him some money and sending him on his way. “Let’s eat.” Jackson spoke up, closing the door behind him. “There’s some meat thing and some other thing. I don’t really know.” He set the boxes down on the table in the living room. “I’m going to go change, help yourself.” Jackson unbutton his pants button before walking away to his room, grateful some pressure was relieved. 

[jacksonrossett]

night changes

[jacksonrossett]

wtvrdrew:

“I think as a guy who’s paying me for sex, you’ve lost your right to not seeming eager.” Drew shrugged, still smirking. “Wouldn’t that be easier for you though? That way you wouldn’t have to worry about people finding out about us. Our deal, I mean.” He frowned at what Jackson said. He knew it was a joke - or, he hoped it was - but it didn’t bode well with him. “You eat pandas? Like, actual pandas? The big fluffy bears? Why? That’s weird. That’s like eating a - a kangaroo. You rich folk are weird.” He scoffed, shaking his head. “You make me out to be this horny 12 year old virgin that’s desperate for you or something but we both know who the needy one is here.” Drew rolled his eyes, moving a hand to Jackson’s chest. He was a little flustered by his words and gave him a half hearted shrug. “You could have just asked me, you don’t need to have some elaborate plot to get me to do things.” He let his hand travel down lower before he pulled it away. “We’ll see how things go. Play your cards right and I’ll be sitting on more than just your lap tonight.”

 He raised an eyebrow but didn’t say anything. He wasn’t about to accuse Jackson of lying, he wasn’t about to think too much of what was probably just a simple business deal that he had no influence over. “If the boss likes me? Let’s hope he doesn’t like me the way you like me.” He gasped softly, reaching down to move Jackson’s hand away from his ass. “And how much of that more than steady income goes to me?” Drew bit his lip, letting a small bit of lust fill his eyes. “You can take control of me whenever you want.” He brought his lips close to Jackson’s but didn’t let them touch. “Cause I’m all yours.” He pulled away completely when he heard Jackson basically scold him. He rolled his eyes, giving him a hard look. “And here I thought you telling me off would be hot.” He sighed, looking down at his hands before he looked back up. “Does it look like I brought it? I wasn’t exactly going to bring my homework here. That’s not hot, you don’t pay me so you can watch me do homework. You pay me so you can do… me.” He paused for a moment, he wanted to stay but now he definitely couldn’t. “I wasn’t staying tonight, anyway. I told Sam I’d come home tonight.” Narrowing his eyes slightly, Drew tried to work out if Jackson had an ulterior motive. His education had nothing to do with sex. “And what would you want in return? Apart from having a super hot, super smart boy - uh, companion.” Drew nodded at the word secret. He definitely wasn’t upset about it and he would go to his grave denying that it hurt even the tiniest amount. The whine caught his attention and made Drew smirk. He brought his lips close to Jackson’s again, but like before, he didn’t let them touch. “My inability to sit down properly reminded me of how well you fucked me. Maybe I should piss you off more if it makes for better sex.” He tilted his head so he could press a soft kiss to his neck, travelling downwards a few inches before he spoke again. “If you really want me under your desk, I’ll let you know when I don’t have classes and you can just say the word and I’ll be there.” He hummed softly, bringing his lips back to his neck while he pressed down against him. “You get so worked up daddy, I’ve only been here for a few minutes.” He laughed softly. “Do you want me to do something about it or should we wait until we’ve eaten first?”

“I’m the one paying, I can say whatever I like.” Jackson said, raising his hands in defense. “Why would that be easier for me?” He was somewhat appalled that Drew would suggest that. “It might be a secret, but I wouldn’t want you dying over it. Shit, I’m not that bad.” Nothing like this would ever be worth dying for. “Oh yes, definitely. Panda meat has a very unique and rich flavor. It’s one of the most expensive meats you can buy. Take a joke and run ten miles with it into offense.” Jackson rolled his eyes, still getting used to Drew’s reactions. “You are a horny twelve year old. But I can guarantee you’re not a virgin.” Jackson was the desperate one here, apparently. He just wanted a companion, there was nothing wrong with that. “I’m not going to ask you as if you were some whore.” He stated bluntly, his lips forming a straight line of disapproval. “Even if I am paying you for your time, I’d rather things happen naturally. I wouldn’t want you faking anything.” He wanted Drew as a genuine person, not just as some fuck. Even though a sinking feeling in his stomach told him that not everything was probably real between them. But did it matter? His eyes dropped down to Drew’s hand lowering down his chest, swallowing quietly as he pulled his hand away. “I sincerely hope thats the case, baby. I want to watch you tonight riding me.”

Even though Drew tried to make his hand move, he only moved away for a moment before reaching back towards him and gripping him even rougher. “No one should like you in the way I like you. Especially not an employee of mine.” His voice was possessive and a smirk grew. Employee or not, he’d probably take down anyone who threatened to get between their relationship. “Enough to pay for uni. I don’t know the percentage off of my head.” In truth, he knew, but it was such a minuscule amount he didn’t want to offend him or think he was cheap to him in anyway. Jackson didn’t enjoy Drew’s teasing, not when he was already excited. “You’re all mine.” He murmured, his eyes focused on Drew’s lips. Somehow Jackson felt in a way, he was all Drew’s. He’d never say it, but it was the truth, Jackson didn’t share himself with anyone else. “I’d rather you do your homework before you get here. I don’t want you to do it here, I want you to do it period.” His voice was stern, feeling like the actual adult in the situation. His throat dried when Drew said he hadn’t planned on staying anyways. Was it because of last time? Was his room unacceptable? Any reason, he hated it. “In return?” Jackson felt completely defensive. “In return I want you to get an education and not have to do this for the rest of your life. I didn’t know all my motives had to be sexual or selfish.” He snapped, was it so bad he just wanted Drew to actually succeed and do well with school. “I didn’t really want you staying over anyways.” Jackson sounded like a child now, not wanting to look desperate. Was that how Drew saw him? Some desperate old man? “At this rate we’ll be fucking just as hard by the end of the night.” Grabbing his chin, he took control to kiss Drew, but just long enough to get the attention he wanted. Leaning back lazily, he opened his neck to show more skin to Drew’s lips. “I’ll have Tiffany compare schedules.” He said softly, his mind now focused on the soft pressure of Drew’s lips. “Once we eat we’ll see how much time is left before you should go home. Don’t want to keep Sam up waiting for you, do we?” As hard as he was, he could deny himself sex just to prove a point to Drew. “I’m not that desperate.” 

[jacksonrossett]

night changes

[jacksonrossett]

wtvr.drew:

“No, I was starving myself in hopes that you would eventually call me and invite me over.” He spoke sarcastically, the smirk still on his lips. Maybe he was a little bitter it’d taken this long - even if it was a relatively short amount of time - for them to finally meet up again. “Yeah, you know, you rich people have like certain foods you eat and you do that thing were you frown upon other foods. You know what I’m talking about.” Drew raised an eyebrow, a little surprised at his words. “Good. I can’t hook up with someone who doesn’t like pizza, that’s like, against my moral code or something.” He glanced down to Jackson’s hands on him then back up, shutting his eyes as he kissed him. It felt nice. He could get used to nice. He was half expecting Jackson to have him do something while they waited but it seemed as if that weren’t the case. He kept his mouth shut as they moved into the living room before he narrowed his eyes for a moment, hesitantly getting onto his lap, shifting around to find the comfiest position. “I’m a little big to be a lap dog, don’t you think?”

Drew groaned softly when he saw him put the news on but didn’t get the chance to complain. He glanced between the image of Jackson on the tv then to him. He’d never been with someone who had been on tv and he couldn’t even gloat about it. “Impressive.” he nodded before he smirked again. “Did you do that for me? You didn’t have to. I appreciate you making a steady income though.” Business talk wasn’t his thing but Drew figured he could entertain Jackson, play into whatever he wanted and get more for himself in the long run. It was a win-win situation. “You know daddy, it’s super hot how you take control like that. Helping all of these smaller businesses.” He licked his lips before he brought his lips to his ear. “It turns me on.” He looked away, half shrugging at the mention of school. He’d have rather not spoken about it. “I had a few classes today, which sucked. I thought uni was supposed to be better than high school but apparently not.” Knowing he didn’t want to sit there and complain, he continued quickly. “I hope you know I blew off doing my homework to be here.” His eyes flickered to Jackson before he absent mindedly touched his neck. “They wanted to know. Kept asking me, repeatedly. Sam really wanted to know. He used the best friend excuse but I didn’t tell him. I didn’t tell anyone. It’s still our little secret.” He nodded, hand still brushing across his neck. “I’d like that.” Biting his lip, he leaned forward and kissed Jackson before he abruptly pulled back. “You have no idea how much.”

Jackson caught onto the bitterness Drew was glowing with, it only made him feel a bit more smug. “Didn’t want to seem too eager.” Well, it was true. “I’m glad you didn’t starve, a few more weeks and you’d be dead. Can’t have that on my conscious.” Jackson thought one day he’d break his neck by how often Drew made him shake his head. He was like some bobble head that was fueled by Drew’s sarcasm. “Only eat kobe steak and panda. That’s what is on the pizza, so I hope you enjoy that.” He could be snarky and sarcastic right back at him. “You’d want to hook up with me either way.” Pizza wouldn’t stop Drew, he had a feeling money would out rank pizza eventually. Laughing at Drew’s uncomfortableness, Jackson only held him tighter down. “You aren’t my lap dog, I just want you on my lap. Maybe it’ll spark some need to ride me, which you so proudly advertised your skill at.” Jackson smirked, nipping at his shoulder. It was easier to see him than he thought it might be after last time. He’d shown him too much, said too much- but it seemed like none of that concerned Drew anymore. Maybe they were both a bit embarrassed of how things quickly escalated. 

“Buy the publishing company? No.” Maybe. Drew had inspired him a bit, and it was just some whim purchase, it had reminded him of Drew. “One day you can’t work there, if the boss likes you.” He teased, pinching at Drew’s ass. “I make more than a steady income.” This was the proper way to socialize with Drew, not some emotional breakdown between the two of them. Jackson remained poised, listening to Drew tease him- but he got him excited from just calling him daddy, let alone saying it turned him on. “You know I like taking control and taking what’s mine.” His breath caught in his throat, his pants suddenly feeling much tighter. He’d buy him his own apartment if that meant he had him talking to him like this. His ear was still burning from Drew’s closeness, surprised he seemed to come out swinging- he had Jackson K.Oed in the first round. Almost missing his comments about school, Jackson paused and frowned. “Your homework? Did you bring it?” His voice was disapproving, education was important to him. “I was going to have you stay over but, I guess you can’t stay too late now.” Looking down at his watch, he started calculating time, not wanting to keep Drew too late. “How about I tip you according to your grades? Every time you get an A on a test or project, I’ll give you £200. Does that help encourage you?” Jackson never wanted himself to come before Drew’s education, it was what he was essentially paying for.  “Our secret.” Jackson smirked, pressing close to him. “You like it when daddy marks you as his? Reminds you how well daddy fucked you.” Jackson leaned into the kiss, only for Drew to pull away, a whine escaping his lips- which he instantly hated. “Daddy missed you too. Thought about you all day under my desk during meetings. I was so fucking hard I couldn’t stand up to shake anyone’s hand. Bet you can already feel what you do to daddy.” Leaning his hips up against Drew’s ass, he let out a soft groan. 

[jacksonrossett]

night changes

[jacksonrossett]

wtvrdr.ew:

Drew liked to believe he had done a good job at making up excuses for his not coming home and the marks on his neck. His friends had asked multiple times where he’d gotten them from but he’d merely shrugged it off, not wanting to indulge them. His friend, Sam, however, had been a little bit more intrusive. “I’m just saying,” he said as he sat down next to Drew. “You don’t just disappear for the night and then come back covered in hickies.” Drew rolled his eyes, shoving Sam away from him and picking up his phone. “It’s none of your business.” he muttered as he checked for any messages, any calls. He’d been doing it periodically, neglecting his homework in favour of seeing if Jackson had got in touch with him. He was excited for the prospect of seeing him again. And getting money. Because that was the point of this whole thing, him getting the money. He could hear Sam rambling on behind him as he checked his phone again, smiling when he saw the texts he had gotten. “I gotta go.” He got up, shoving his phone in his pocket. “Are you coming home tonight?” Sam asked. “Sure.” Drew shrugged, before leaving.

Upon seeing the car waiting for him, Drew smirked. This was insane. It was also interesting to see the lengths Jackson would go to to have his company for a few hours. Getting into the vehicle, he hoped the drive wouldn’t be too long. But why? The money, he told himself. It was definitely the money. What else could it have been? Arriving, he got out quickly and made his way over to the elevator, still very inpatient until he arrived at the penthouse. He was still in awe of the entire place and he figured it would take a while for that awe to wear off. Despite his impatience, he was a little hesitant. The other night was still ripe in his memory - he couldn’t afford to ruin things the way he had before. He wasn’t going to be a whiny brat this time around. Going in, he saw Jackson and crossed his arms, moving further into the place and to Jackson. “I know something I’m craving,” he said, smirking. He knew it was obvious what he was referring to but he wasn’t about to give Jackson that amount of control. Not yet. “And that’s pizza. I want pizza.” He walked over to him, only leaving a small amount of personal space between them. He wouldn’t exactly call this teasing. “Unless that doesn’t suit your rich boy palette.”

Shaking his head, Jackson turned around to see Drew smirking at him. “Oh yeah?” He was surprised Drew had come out already teasing. Pizza. “Of course, hope you haven’t already had dinner.” Picking up his phone he texted Tiffany to order them some pizzas, whatever the specialties were at the nearest acceptable pizza place. “Rich boy palette?” Jackson raised his eyebrow. “I’m having some pizza sent over. I enjoy pizza, contrary to your beliefs.” Walking over to Drew, his hands rested on his hips- his hands warming up against Drew’s skin as he slipped them under his shirt. “Food will probably be here in thirty or so.” Leaning down, he pressed his lips to Drew’s jaw. He was just as soft and warm as he remembered from their first meeting. Especially that quick witted mouth he just wanted to capture. Parting from him, he wrapped his hand comfortably around his waist while guiding him to the living room, sitting down in his large leather chair. Pulling Drew between his legs, he looked up and grabbed his hand to pull Drew onto his lap. “Come here.” Grabbing his remote he turned his tv on and ignored the large child on his lap.

Switching the news on, he smirked as he leaned back- knowing what was coming on. Only a few moments later, his image flashed on the screen about stocks rising quickly as his company had grown. “Look what daddy did.” He wanted to share his enjoyment with Drew, this was his pride and joy. “I bought a small publishing company, you know.” He said softly, leaning forward and resting his head onto Drew’s shoulder. “And a few other big companies that were cheap, but profitable. They just needed some money to get lifted off the ground. Everything is paying off now.” He was growing impossibly richer, one of his few joys. Holding Drew close, his hands moved around his waist again. “What have you been doing? School?” His eyes traced over his neck, his marks still visible. A ray of pride and grinned, pressing his lips to one. “Interested friends? Were they impressed by daddy’s work, hm? I can refresh them, you know.” Oh there would be sex tonight, he wanted it- he needed it whenever Drew was going to be around. It the attraction he had towards him. There was a strange comfort that was foreign to him, Drew was something he pretended he control. “Miss me?” 

[jacksonrossett]

night changes

“You seem more chipper today than usual.” His assistant, Tiffany, noted while handing him papers to sign. Jackson didn’t pause to answer, just signing. “Is it the cute tall blonde I had to write a very... wordy explicit contract to?” Sighing, he put his pen down and gave her a look. “Ouch, don’t shoot me.” She raised her hands in defense and took the signed paperwork before exiting. Maybe it was Drew. He hadn’t texted him the day after their first meeting, even though he had thought about it. Yet when he got to work he kept glancing at his phone and wanting to text Drew, and he hated that feeling of dependency. “Fucking kid.” He sighed, leaning back in his chair and pulling his phone out. Jackson was going to hold out a bit longer, but he couldn’t. Not with a mouth like that, or eyes.

“Dinner. Your pick.” He texted Drew, pausing before he hit send. Maybe he shouldn’t let him pick, what if he wanted something Jackson didn’t like. Or maybe he was giving him too much power again. Jackson already hated the fact that he saw him in such a weakened state. It’d be different from now on, he’d make sure of that. “Car coming to get you, be ready. My place.” Grabbing his jacket, he threw it on and walked out of his office. “Call a driver to go pick up Drew.” He said, ignoring the laugh Tiffany let out to tease him. Getting to his apartment, he checked his watch wondering how long it would take for him to get there. Jackson hadn’t asked him, and he didn’t check his phone. If he wanted money and attention he would come. Though, he wanted him to. Walking in, he turned the heater on and went to the wine fridge to pull out a fresh bottle before realizing Drew probably didn’t have a taste for wine. Maybe he should invest in some beer. Hearing the door open, Jackson kept his back to the door. “What are you craving, baby?”

[jacksonrossett]

prove it

[jacksonrossett]

wtvrdrew:

“I’ll teach you.” He chuckled, nodding a little. “Think of it as a bonus part to our deal.” He smirked, shaking his head. “Lunch doesn’t woo me. You woo me. There’s a difference.” When it came to normal relationships, Drew was more interested in the person than anything else. This relationship was a direct contrast of that. “I know how a job works, I know how income works too. Meetings sound boring. It seriously can’t be fun sitting in an office hour after hour talking to people.” He smiled, impressed that Jackson would do such a thing to spend time with him. It felt nice. “You’d do that for me? That’s cool. That’s really cool.” Drew blushed, looking away as he smiled. “I’m happy you want to keep me around.” Shaking his head, Drew glanced down to the ground before looking back up, his cheeks still red in colour. “I didn’t mean it like that. I just meant - I don’t know, it’s not a conventional job, is all.” He half shrugged, not sure if he should have demanded respect but relieved to know he had it. “I’m not here to be treated like shit. I won’t let you do that to me.” 

Drew raised an eyebrow at what he said but a small smile spread on his lips. “That’s a shame. You’re almost old enough to be my father.” He shook hsi head, laughing at his own joke. “No, I’m just letting you fuck me so I can get money.” he said, sarcastically. “I actually hate being fucked by men, I’m just really cheap.” Drew looked away, still embarrassed that he had admitted that but felt something warm stir within him. He wouldn’t have to share. Not that it was even a problem, he shouldn’t have been so worried about that in the first place. “I hope we’d be alone. I didn’t agree to threesomes.” He joked. Sarcasm and humour was his usual defence mechanism when it came to things like this. “You don’t have to meet them. That would just cause problems.” By now Drew had assumed that his cheeks were going to be permanently warm. “It matters to me.” he mumbled. then cleared his throat. “Not that that would be a problem, I mean, we’re not dating, we’re not exclusive you can - you can see other people if you want.” Part of Drew knew that it would hurt him to see Jackson with someone else but he had to acknowledge that they weren’t with each other. It was just sex. Drew feebly attempted to pull his wrists from Jackson’s grip before he wrinkled up his nose, shaking his head. “Don’t be rude to me, daddy, it hurts my feelings.” Pulling his hands back into his lap, he smirked. “You’re just looking for an excuse to touch me.” Drew remained silent, wondering if he’d said too much. “Sorry, I shouldn’t have been so open.” He hummed around Jackson, his hand lazily stroking whatever wasn’t in his mouth. The praised left a tingling sensation within him and he sped up his actions, working quickly in an attempt to further please him. He moaned softly, slightly leaning into his touch while he allowed his tongue to swirl around him, his head moving at a steady pace. 

“Aren’t you generous? What would be your first real person outing be?” He teased, his curiosity showing. Jackson always wanted to know more, but even more so if  it would somehow build on their relationship. “Can I woo you at lunch?” He wasn’t even sure what wooing was referring to anymore. “I sure as hell can fuck you at lunch.” Mumbling, Jackson gave him a sly look. “I sat in an office talking to you, it can’t be so bad.” Shaking his head, Jackson paused to gather his thoughts. “I like meetings. It gives you some sick sense of power over someone. They want my business, I want their money. Sometimes it works out I don’t even need to give them business to get their money. It’s interesting to see people at play, talking and trying to hide things. It’s like a game of cat and mouse.” Jackson realized he was rambling and looked away, Drew was too easy to open up to. And by the redness on his cheeks, Jackson assumed they both had a bad case of foot in mouth around each other. “Of course I want to keep you around. Do I not make that clear?” Jackson always wanted to be clear on his meaning, with Drew it seemed he was hit and miss about 80% of the time. “Like I said, baby, if someone gives you trouble I will personally see to it that they are handled. You’ll tell me, won’t you?”

Frowning, he hated being called old. “I’m not old enough to be your dad.” He reached up and flicked at his shoulder, shaking his head at Drew’s bad joke. “You’re anything but cheap.” Jackson smirked, knowing just how much every moment was draining from his bank account. “And from what I can tell, you love me fucking you. I must be an exception.” He knew Drew was joking, or he hoped so at least. Because then nothing previous to this made any sense whatsoever. “Ah, I forgot about threesomes. Didn’t you read the fine print? One threesome a week.” He joked, threesomes weren’t his style. He had hardly enough emotional stability to handle one Drew, let alone two- at the same time. Raising his eye brows, he was surprised. “You do mind then. We’re not emotionally exclusive. Obviously I can’t be everything to suit your emotional needs. I don’t mind if you have someone else. I won’t be sleeping with anyone else, there’s too much hassle. And I’d prefer it if you didn’t sleep with anyone before warning me.” So he could destroy the person before he ever got to touch Drew. Jackson paused, was he that possessive? “Emotionally though, I really implore you to look for other outlets that are healthy for you.” He held his wrists for a moment before letting him go. “You? Hurt feelings? I didn’t think that was possible.” Honestly he was surprised that Drew so easily called him Daddy, maybe he was into it too. He hoped he was- but it was also part of his job. “I don’t need an excuse to touch you. Unless you say so, I will touch you as I please. And I think you enjoy it.” His hand reached up and traced the outline of his neck and down to his broad shoulders, he was really gorgeous. “Hm?” Snapping out of his thoughts, Jackson looked up at Drew and shook his head. “Don’t worry about it. I’ll listen.” Jackson bit his lip, watching Drew speed up with dark eyes. He knew he wasn’t going to last, he should have waited until before he left for work and been more composed. “Fuck, baby. I’m going to come.” His eyes stayed on Drew’s blues, completely entranced and sensitive. Thrusting up into his mouth, he finally came with a loud moan of Drew’s name. Panting, he reached down to pull him up and bring him onto his chest. “Morning sex... I can’t really- do for... Long. You’re such a good boy for Daddy.” He panted, pressing a kiss to Drew’s forehead. “Try and go back to sleep.”

[jacksonrossett]

prove it

[jacksonrossett]

wtvrdrew:

Drew smiled softly, amused by Jackson’s words. “You want me to teach you what normal people stuff is?” He laughed and shook his head. “Lunch? Wow, you really know how woo a guy.” Drew raised an eyebrow. He’d never met someone who wanted to please him so much, it felt foreign to him. “I hope you don’t have too many meetings. I would really hate to miss out on everywhere with you cause you have to work.” Everything was up to him? Drew had a sinking feeling that if that were truly the case, Jackson would like what it was that he really wanted. That was already obvious. “I know.” he nodded. “I don’t think you’ll destroy me. Destroy is too harsh of a word anyway. It’s a lot more negative than you probably intend for it to be. Don’t use it again.” Drew scoffed and shook his head, a smile playing at his lips. “If there’s one thing that you’re wrong about, it’s that being emotional is a good thing. In any world. It’s just tolerated a little bit more in mine.” He just shrugged, looking down at the ground. “I mean… you’re not wrong for saying it… I’m no better than anyone who sells themselves for a living.” He stayed silent, narrowing his eyes as he looked back up at him. He shut his eyes as they kissed, wanting to seek affection but he didn’t bother. He wouldn’t get it. “I’m not mad. Just… defensive.” Drew looked at him as he laughed and he shrugged. He knew he should have kept his mouth shut. “Well… I do already call you daddy…” he muttered, a half baked attempt at humour. “I like being fucked by men.” he said, not sure why he was trying to relate but he did it nonetheless. “I’m not trying to set you up with my family. I’m not stupid, I want to keep you to myself.” He blushed suddenly realising what he had just confessed to. “I mean… I… uh…”. He released a short breath before he decided to quickly change the subject. Pouting a little, he shoved at Jackson’s chest. “I told you to ignore what I said anyway. Why didn’t you listen to me?” He rolled his eyes and whacked Jackson’s hand away from his hair. “Um, you’re not supposed to call me a brat. That’s not fair.” Drew stared at Jackson blankly for a few moments. He wasn’t sure if he wanted to divulge his family’s problems to him but for some reason, he felt much safer sharing those secrets with Jackson than with anyone else, even his friends. “My dad didn’t want…” He stopped, shutting his mouth for a minute or so before he nodded. “I am lucky to have her. She’s great. I just wish I was as good as her.” He smirked, shaking his head as he wrapped his hand around the base of his cock. Still smirking, he leaned down to lick the tip teasingly. “Hm, nice.” He moaned softly before he took him into his mouth, taking in as much as he could. Glancing up at Jackson through his eyelashes, he began to move his head, tongue brushing against his shaft as he did.

“I might need you to teach me a thing or two.” Jackson laughed, his hand scratching the back of his neck. A lot of people would pay a lot of money to have Jackson Rossett admit that he had something to learn from them. “Lunch is how I woo people. I think I’m wooing you just fine.” He wasn’t a wooer, he didn’t woo people- people spent years trying to woo him. “Meetings mean more money, and more money for me means more money for you and things we can do together. I have them often, but that’s just like going to class for you- they just block up the day during certain hours.” Jackson shrugged, his schedule was flexible though. “People want to meet me, I don’t have to go searching for people. I can move things around so we have time.” He liked showing off his power muscles for Drew. In a way he was trying to impress him, make him admire who he was. But on the other hand it was plainly the truth, they would have time together. “Especially since you’re apparently an adventurer.” He teased with a smile. “Good, I’m actually kind of... Relieved that you agreed to this.” Jackson sighed, his mood decreasing from it’s previous generous high. “Are you saying my mother wasn’t good?” He frowned, glancing at Drew, posing it as a simple question. “You’d be right. But I still have more respect for you than most people would. So don’t think I’m here to treat you like shit.” The complete opposite. 

Shaking his head, Jackson couldn’t help but crack a smile. “As much as I’m your daddy, I’m not your father.” Looking up, he couldn’t believe this kid sometimes. “I hope you like being fucked by men, or we’d have a problem.” It would have been awkward if he didn’t like it. He wanted to keep him all to himself? “Don’t worry about sharing me with anyone, when we meet we’ll be alone. I intend on avoiding meeting your family at all costs.” He wasn’t going to meet them period, that wasn’t his job. He wasn’t playing boyfriend. “And I shouldn’t have to tell you this, but there isn’t anyone else in my life, if that matters to you.” A pang in his body hoped that it meant something- at least to calm him. “I don’t have to listen to you.” Jackson smirked, grabbing his wrists when he pushed against his chest. “And you are a brat. How is that not fair? My baby boy is the biggest brat in this whole city. Pushing me to want to pull him over my knee.” He teased, releasing his wrists. He dropped the playful attitude when Drew started, but didn’t finish. Jackson wasn’t sure if he wanted to know this much personal information. At the end of the day he still didn’t fully trust Drew, he might turn some story on him to make him feel worse. Or try to get information out on him. He’d already told him about his mom, and not even the press knew that about him. Most people had just assumed Jackson was adopted. Snapped out of his thought, Jackson let out a groan from Drew licking him. “Be a good boy, don’t tease dadd-” And then he took him all, causing his hips to thrust up slightly. His hand moved to grab his hair, watching him with mouth slightly parted. “Fuck.” He gasped, biting his lip as Drew worked him over. Jackson was very sensitive in the morning, even after a whole night of fucking. His hand slipped down to hold his cheek, watching him with burning eyes. “Best fucking mouth.”

[jacksonrossett]

prove it

[jacksonrossett]

 ,wtvrdrew:

“I’ll go for free.” Drew said, quickly before raising an eyebrow. “Guess that’s the only downside to this deal. It’d be cool if we could do normal stuff together.” Shaking his head, he realised what he’d said. “Not like dating stuff or whatever, since that’s not what this is.” He sighed, shutting his eyes for a moment to recompose himself. “I’ll go to Italy with you for free.” Drew smiled at his question. “Everywhere. Europe, Canada, Africa, everywhere I could possibly go. I’ve always loved travelling. Like, we had to travel to visit my mum’s parents once and it was so cool.” Drew blushed, realising that he was practically rambling. Slightly, embarrassed, he looked down at the ground and shrugged. “I guess so.” he muttered. He knew it wouldn’t take much for him to be able to pay off his loans and such but part of him - and a large part at that - wanted this deal to last a while. But it lasting a while meant he’d get attached and he didn’t need the embarrassment of being told he’d gotten too clingy yet again. “We’ll see.” Relaxing, he nodded. “Alright. Just kinda hard to understand what you mean with some things.” He looked at him, listening to what he was saying. “Okay. Good. I trust you.” He chuckled, nervously. “I’m an easy guy to destroy.” It was a joke laced with some truth - he wore his heart on his sleeve, it was easy for people to hurt him. “People like me? Now, that sounds like an insult. There’s nothing wrong with being emotional.” He sighed, looking away from him. “Not anything. I do have some dignity left.” Drew hadn’t known what he’d expected by saying what he had. He shouldn’t have expected someone like Jackson to want a life like his. “I don’t know why you would want a taste either, my world obviously isn’t good enough for you.” Drew nodded, half shrugging. “Gotta find a way to make a quick buck.” He let out a shaky breath at what he was saying coupled by his lips on his neck. “I’d like that.” While talking, Drew tried not to pay too much attention to Jackson - he wasn’t sure if he would actually care or even listen to him - but upon hearing him speak, he smiled softly and turned his head to look at Jackson. “She’s really pretty.” he agreed. “You could date her.” He chuckled, shaking his head. “I mean, if she wasn’t with my dad. You could date my sister though, she’s like me but less…” Less what? Less complicated? No, Drew couldn’t say that. “But with less dick.” Looking at Jackson again, he shrugged. “That would be weird though, considering you’ve had sex with me. Don’t date my sister. In fact, forget I even said half of what I just did.” Drew figured it was the lack of sleep that was making him say what he was. He needed a certain number of hours sleep - or amount of caffeine - before he could properly filter what he was saying. “Nope. Not fond.” He shook his head then raised an eyebrow, leaning into his hand slightly. “You’re lucky you don’t. I’ve heard we’re brats.” he joked, smirking at Jackson before the gesture faltered. “They’re not worthless. I - I love them, they’re my family. I just - I’m not my brother y’know? If I was more like him then my dad would like me more but… But I can’t be like him. I’m basically a carbon copy of my mum. My dad doesn’t like that.” he sighed, shaking his head. There was more to it than that but Drew didn’t want to upset himself. “My brother just wanted to be the only boy. Guess he was kinda shocked when they brought me home.” He laughed at his own words, despite them not being remotely funny. “I doubt it. He’s thirty, I’m just some kid to him now. But it’s fine. I have my sister.” He raised an eyebrow at what Jackson said, part of him wanting to say something in response to it but his words were lost against his lips. His mind was sluggish again, taking a few moments to even register what was happening before he heard Jackson’s voice. “You’re a fucker, daddy.” he muttered, getting up. “You don’t mind me being on top of you, huh?” His fingers found the waistband of Jackson’s underwear and he began to slowly tug them down.

“We can do normal people stuff.” After he truly found out what normal people stuff was. What was considered normal? Fuck. “Obviously not. But we could still go to lunch together and whatever.” Jackson was surprised that Drew would go to Italy for free, but whatever he wanted was his choice. For some reason it made Jackson a little happy, maybe he wasn’t completely money hungry. “I’ll try to squeeze everywhere in between my meetings.” He teased, watching the blush take over Drew’s face. He noticed he blushed a lot, it was endearing and somewhat... new. He never had people blushing this much around him, maybe he was getting charming. “Everything is up to you, you have the final word and you know that.” Shaking his head, he frowned. “Drew, no.” He was getting caught up in his quick reaction and defense mechanisms. “I’m not looking to destroy you. If anything I’m looking to help you in any ways possible.” Jackson was stupid in overreacting and saying ridiculous things. “Being emotional is a good thing, for you.” For him, not so much. He hated it when Drew looked away from him, he felt a pang of guilt. “I know. I’m sorry for saying that.” He murmured, tilting his chin back towards Jackson. “Your world is different, I don’t fit in there. Not that mine is better than yours, it’s just completely different.” He pulled him up into a kiss. “Don’t be mad at me, baby.” 

Shaking his head, Jackson let out a laugh. “Date her...?” Why on Earth would Drew ever suggest that he date his mother. “Want me to be your step father? That’s awkward.” Then he lead onto his sister, causing him to let out another laugh. “Now your sister?” If he was fucking Drew, why would he want to date any female member of his family? “I like fucking men, Drew.” He said bluntly, smirking. He wanted Drew, or else he would have found one of the other million blonde girls throwing themselves at him. “I like fucking you, please don’t try to set me up with your family. They’d murder me.” Sure he had been married to a woman, but he did prefer men. Their marriage was complicated, too complicated for words. But at the end of the day it was more about business and personal ties than love or sex. “You are a brat. But it’s endearing and sometimes cute.” He smirked, tugging his hair briefly. He couldn’t help but quickly lose his smirk and frowned. Jackson justified everything by saying that things were worthless and didn’t mean anything to make the pain go away. It was strange that Drew wanted it to be clear. “He doesn’t know what he’s missing out on, I’m sure. Who wants a copy of a son you already have anyways? Doesn’t your dad love your mom?” He was confused, wouldn’t a father want a child that reminded him of his wife? Things were clearly complicated in their family. He wasn’t sure he wanted to dig into it, but he was somewhat curious. “Your brother sounds like a jealous asshole.” He spoke bluntly, looking away for a moment. “At least you have her, you two seem to get along really well.” In a way even Jackson was jealous of this relationship he didn’t really know. Leaning back, he rested his back on the headboard and watched Drew climb on top of him. “Daddy has been patient and has had a rough night. I think he deserves it.” He smirked, his eyes darting down to his underwear disappearing. “As much as I love seeing you on your knees, you being on top is a lovely sight as well.” His hips shifted up to let his underwear slip off easily. “C’mon baby, take care of daddy.”

[jacksonrossett]

prove it

[jacksonrossett]

wtvrdrew:

Drew shrugged. He was far too used to the sympathetic looks and words people gave him and his family. He used to blocking it out now. “It’s fine. It’s not a big deal.” Any other time, Drew would have been embarrassed with how eager he was coming off, how excited he was to do something that was so menial in other’s eyes but he couldn’t find it within himself to reign it in. “That’s fine with me.” he said. “I don’t mind. Who else gets to say they spent a few days in Italy? Well, probably a lot people but whatever.” Drew frowned a little but shook his head. “Didn’t realise you’d be paying me. I would have gone for free.” The admission left him blushing and he looked away. He probably should have been looking for the best way to get money and saying what he did wasn’t the best choice but he would have gone for free, he’d have taken the opportunity to go abroad with no questions asked. And he got to go with Jackson but he was still deciding whether or not that was a pro or con. He nodded and drifted towards him a little, wanting to reach over and take his hand but he knew hand holding wasn’t Jackson’s thing, instead, he crossed his arms to help fight the urge. “Is that supposed to be an insult?” he asked, confused. He’d already known, before Jackson had said so, that he wouldn’t fit into that world. It was just clearer as to why now. He frowned, unsure what to make of what was being said to him. “You picked me because I’m too good? Because you want to destroy that?” He paused, thinking for a moment. “Or is it because you’re like me? You want a taste of something you’ll never have?” Drew wasn’t convinced by what he said but he wasn’t about to question Jackson. If he wanted to do and say the things he did, then it wasn’t Drew’s place to question him. “I mean… embarrassment aside… you’re pretty good at giving out compliments.” he muttered, hoping it was diffuse the situation somewhat. Drew shrugged, the heat never leaving his cheeks as he rubbed the back of his neck. “I like it.” he muttered. “It’s - It’s hot. The idea of being out of control like that, it’s hot. That’s why you were my first choice.” He looked away quickly. “And the money, of course.” He couldn’t forget why he was here, not this early on. Drew was surprised by Jackson’s question. He hadn’t expected it but that didn’t matter. He narrowed his eyes before shaking his head. “I don’t.” he said, honestly. “Some people have bad minds but that doesn’t make you bad.” He moved backwards with Jackson, pressing his back against the wall while he eyed him carefully. There wasn’t much to say, he wouldn’t know what to say anyway and instead, found his hands reaching forward, grasping as Jackson’s sides to pull him closer. Maybe it wasn’t what he wanted but Drew had found that sometimes closeness helped. This was part of the deal he hadn’t been expecting though part of him knew Jackson hadn’t meant to show him this and he wasn’t sure if he would get to see it again. He fixed Jackson with concerned eyes and allowed him to guide him back to the bedroom. He’d give him what he wanted. That’s why he was here, after all. “My family?” he asked. “Sure, okay. I’m the youngest of three kids. There’s kind of a gap between me and my sister., age wise. Her name’s Arabella. She’s my best friend.” He blushed, looking away momentarily. “My mum’s a nurse. She keeps our family together and we’d be a mess without her. She gave me everything, especially her eyes. My dad and brother… they’re, uh, they’re really similar… which is why I guess neither of them are really fond of me.” He shook his head, grinning a little. “My brother especially, he hates me and he’s very vocal about it. That kinda bums me out, I always wanted him to be that over protective big brother stereotype, you know?”

“If you want to go for free I won’t stop you. Maybe I’ll just pay you in souvenirs? It’ll be less dangerous for us there. People outside of America don’t really recognize me in casual clothes.” Jackson licked his lips, not expecting him to have wanted to go for free. His head tilted to see more of Drew’s reaction and blush, he oddly liked how flustered Drew seemed to get in his excitement. “Where would you like to go, if you could go anywhere in the world?” Jackson didn’t pity him, he wanted to do something to make him happy. Something to make him want to stay more? He wasn’t sure. “The more we go out, the faster you can get out of this, right?” He asked, searching his eyes. Isn’t that what he wanted? “I doubt it will take that long to raise enough money for your tuition with me.” He wanted Drew’s companionship often, so it would work out in both their favors. Maybe he was hoping he could burn through Drew, just to not get attached. “Insult? No-” Jackson swallowed, noticing Drew cross his arms. “It wasn’t an insult.” He said firmly, unsure if he actually pissed him off. “I don’t want to destroy that.” He quickly breathed to defend himself, feeling confused. He went through everyone trying to destroy him, he’d never actively try to do that. “I’d never destroy you, Drew.” Pausing, he looked away- he never thought of it like that. “Have a taste of something I’ll never have.” Suddenly sneering, trying to protect himself. “I don’t want to be like you. I have more power than most people in this world. You think I want to be powerfulness? Emotional? No thank you. I just think people like you are fun. Easy to please, I can get you to do almost anything for money. Why would I want to have even a taste of what your world is like?” Little did Drew know that every word that came out of his lips was the complete opposite of what his heart wanted. 

“I offered you the most money, huh?” Jackson smirked, feeling proud. “I’ll dominate you and make you mine every night.” He nipped at Drew’s neck, liking that Drew wanted him to have power. Some people have bad minds but that doesn’t make you bad. Jackson hated feeling like he was some piece of glass that was easily seen through and broken. He didn’t reply, but he felt somewhat better knowing Drew didn’t think he was a bad man. For the first time he didn’t fight back against Drew’s closeness, it did feel nice. At first, Jackson hadn’t really planned on actually listening to him. His eyes were so focused on his lips, watching carefully. But when he spoke everything seemed interesting to him. He kept quiet and listened, his eyes wide like a child’s as he focused on Drew and not himself. He was relatively normal from what he gathered before, and even now he felt jealousy that he was so normal. “Your mom must be hot then if she has your eyes and looks.” He spoke up, attempting a joke. Jackson wasn’t a fragile man, but in moments like these he had his weak moments. He frowned though, knowing his dad and his brother didn’t have a good relationship. That he could relate to. “Not fond of you?” Jackson reached up and started playing with his hair again. “I always wanted a younger sibling when I was younger.” He shook his head. “Your brother and father are worthless. You don’t need them. Just focus on your sister and mother.” Jackson wouldn’t be a good source of stability outside of whatever a job could provide. He had just assumed that Drew came from some perfect life, it was a stupid assumption. Listening to him had calmed him down, letting out a deep breath. “One day you could have that relationship still.” He offered, unsure how to support him the way someone else might. “My dad probably has other kids. But I won’t ever know truthfully.” He didn’t know why he was saying it, it just came out. Jackson hated how honestly Drew made him, how open he made him at times. Almost out of embarrassment and not wanting Drew to respond, his lips captured Drew’s and pulled him closer. Tangling his legs with Drew’s he bit at his lip and wrapped his hands in his hair, groaning softly. Pulling away he smirked and leaned down to his ear, “I don’t think it’s ever too early for a blow job, baby. Show daddy what a good boy you are at keeping your promises.” Sex his was comfortable with, it made him more controlled and together. 

[jacksonrossett]

prove it

[jacksonrossett]

wtvrdrew:

Drew wasn’t fazed by Jackson’s response. He was used to people being surprised at that. It didn’t seem too bad to him, he’d been on vacation before, he just hadn’t left the country. “Yeah. It’s kind of hard to to leave the country when you have three kids and an unemployed father in your family.” He shook his head, unable to form proper words in that moment. He would actually take him to Italy? Drew was very into that idea, there’d been so many times he’d wanted to go somewhere foreign but knew not to ask - they couldn’t afford it. “I would love to go to Italy with you. I should probably check and make sure I don’t have anything important happening then but I’m sure I can miss one or two classes.” He nodded, still excited. “I’ll be super good if it means you’ll take me to cool places.” Drew gave Jackson a look of disbelief, wanting to reiterate that no one was fearless - fearlessness was a myth made up so the scared had something to be envious about. He remained silent as he watched Jackson’s entire demeanour change. Part of him mentally scolded himself for being so nosy, for prying into something he should never had asked about in the first place but another part was intrigued. A man like Jackson had fears and what he’d mentioned evidently related to fear. “I’m sorry.” he said. “I won’t mention it again, I’m sorry.” He wanted to get close again, to offer Jackson the comfort of a touch but something in him told him to stay put. “I’m not made for it. It’s all too extravagant. Too flashy.” he mumbled. “But momentarily living in it is good enough for me.” 

“I wasn’t trying with you.” Drew admitted. “We all have a - a front we put on for people. I wasn’t exactly putting on a front with you. I figured that - that you’re not like the people I date, you won’t care about the real me or not.” Drew blushed when he referred to him as a diamond. His blush only deepened the more Jackson spoke and he turned his head away, no longer able to look at him. “Oh my god, shut up.” There was no malice behind his words, instead, they dripped with embarrassment and he pressed a hand to his cheek, testing out how warmed it’d gotten. He wasn’t used to people describing him the way Jackson had, sure he’d been call fit and hot and everything in between but never pretty or gorgeous. “Not verbally or mentally, no. Physically, I could be. I’m not strong.” He eyed Jackson then, licking his lips. “Someone like you could easily overpower me.” It’d been a long time since Drew had last slept this close to someone and it felt nice - up until he was jolted awake by screaming. He wasn’t quite aware of what was happening, his mind still not fully awake but he registered movement, could hear Jackson’s voice. He wasn’t quite sure what he was supposed to do, he’d never dealt with something like this before and he could only stare, mouth parted slightly as everything went back to what could be deemed as calm. Looking at Jackson, he wasn’t quite sure if he was meant to say something but it didn’t matter, all he could focus on was his retreating back. “Jackson!” he called out after him, voice cracking a little. Slumping back down on the bed, he wasn’t sure if he should have left him alone or not. He didn’t know Jackson that well, he didn’t know what he did in these moments. What he did know was that he had been right - sharing a bed wasn’t his thing and Drew felt bad for forcing him to do such a thing. With a soft groan, he got up, wiping the sleep from his eyes with the heel of his hand as he made his way over to Jackson’s office. He hesitated at the door, not sure if Jackson would want to see him right now but Drew cared too much and right now, he wanted to make sure he was okay. “Hey,” he spoke softly, so as not to startle him. “Are you -” He stopped. Looking at Jackson, Drew knew he probably wouldn’t want him to baby him. He wasn’t that kind of person. His mind wasn’t exactly working properly, due to a lack of sleep, and he walked further into the room, biting his lip. “Little early for a blowjob, don’t you think?”

Jackson frowned, he didn’t realize his family was that unwell off. He had been privileged his whole life, he never had to want for anything. “I’m sorry I didn’t realize.” His voice was soft, glancing away briefly before looking back at him. “I- um, I’d be busy for two of the days during the weekend. But I figured you could walk around and do your own thing until the conference was over then we’d have two days to ourselves.” He felt somewhat embarrassed, he knew Drew was eager to go, but he had never taken anyone with him like some stuffed bear. “Spend sometime in Rome? That won’t be so bad. Plus you’ll be making money so...” Jackson shrugged. There was that never ending bother in the pit of his mind reminding him that he had to pay Drew to stay with him. Part of him was getting used to the genuine feeling that Drew enjoyed his presence, but he was merely paying him to fill a role. He was no better than an actor, no better than his mother. There was no need to go out of his way to please him. Even as a child that was his entire world. He hoped when someone told him they loved him, it was genuine. “It’s alright, just don’t mention it again.” No one was going to hurt him, his hands released. Finally bringing his gaze back to Drew, he paused. “I don’t think that’s what doesn’t suit you in my world.” He was blunt, honest. “Luxury can suit anyone. It’s the attitude that doesn’t fit. You’re too... Good. Too brash, emotional.” Jackson did have fears, one of them being rejected by those who were genuinely good. He was never good, not under his own definition. At one point he wanted to be like Drew so badly, but he could never survive growing up that way. “People go after that and destroy it. Maybe that’s why I picked you.” He shrugged, his mind too wrapped up in his thoughts. 

“I don’t care what’s real or not.” His voice sounded like he agreed, but his eyes faltered. His idea of common people were they were good and real. It meant everything that Drew was real. Jackson watched the blush on his cheeks and he instantly looked away, his own cheeks warming up. He hadn’t meant it to come across so romantic. “Sorry.” He cleared his throat and looked back to him, his face regaining composition. “Oh baby, I’d overpower you. Something tells me you like me overpowering you and making you mine.” He smirked, feeling that control flow back in his power. In his mind racing, he briefly heard Drew call after him, but he was so focused on escaping. “Get away from me!” Teenaged Jackson screamed, pushing hands away. “Don’t fucking touch me!” This time it came out as a cry, he had never really cried for years now. “You’re your mother’s son, aren’t you? C’mon we’ll show you how to be a man.” Drew snapped him out of his thoughts, his eyes refusing to look up in fear of him seeing through him. He was thankful he didn’t ask anything, there was nothing to tell. He fought to be who he was today, that’s all there was to be said. He grew up in this dark black pit of a world from day one. Instead of paying attention to his silly question, Jackson opened his mouth. “You think I’m fucked up, huh?” He asked, finally glancing up and closing his laptop. His past was dark, but from Drew on, he was going to be strong and relentless. Standing up he made his way over to Drew, pushing him against a wall and placing his head on his shoulder so he could hide. “I don’t want a fucking blowjob.” He had so much he wanted, but he’d never voice it. He’d never let himself become weak and open to getting hurt, not by someone he paid. Maybe he really hired Drew to prove to himself that not everyone who sold their body was bad, someway to cover up the scars his own mother left on him. Everyone who came into his life scarred him one way or another. Lucy, his ex-wife left a physical one on him, a long scar up his back from the car accident. “Just... Can we lay down? Talk about something stupid?” Grabbing his waist, he lead him back to the room where he laid on his bed facing him. “Tell me about your family.” 

[jacksonrossett]

prove it

[jacksonrossett]

wtvrdrew:

“I don’t want to be mean to them, they’re my friends.” Drew muttered, feeling slightly ashamed by what he was saying. Looking back up at him, Drew raised an eyebrow. He was beginning to wonder if Jackson truly understood why he was here. Coming often meant more money and having more money was important to Drew. “Of course I’ll come. I’ll come whenever you ask me to.” Completely disregarding what Jackson was saying and why he was saying it, Drew’s eyes lit up with excitement - wanderlust. “You’d take me to Italy? I’ve never been outside of the country and I’ve always wanted to go to Europe. That would be so cool.” Something inside of Drew was saddened by what Jackson said. Of course, he knew this was completely preposterous. Jackson didn’t make this deal with him for his personality, he shouldn’t have been upset by what he said. Hiding his true feelings, Drew smirked. “I have a pretty good mouth.” He shook his head. “Everyone’s afraid of something. Whether that’s a person or something else.” Gasping softly, Drew glanced down to his hand before pressing his hands to Jackson’s chest, keeping some distance between them. “I knew I’d seen your face somewhere. One of my friends is a business major and she carries around those silly magazines. Should’ve recognised you sooner.” In truth, Drew never paid attention to most magazines either, especially not those of the business variety. “Did he pay to have you too?” Maybe it was prying but Drew didn’t care, if Jackson wanted to speak his mind then he could do it too. “I don’t think I’ll ever be able to get used to your world. I’m kinda relieved I’m only living in it for a few moments at a time, it doesn’t sit well with me.”

“I know it is. I’m a lit major, we know all about words. I am irresistible,” He said, pausing for a moment. “Until people get to know me and then they realise that I’m the complete opposite. Fool’s gold, is what I am.” Drew raised an eyebrow, pushing his self deprecating thoughts to the side as Jackson made his analogy. “Cinderella was pretty, for a cartoon.” He muttered, absent mindedly while processing what he’d heard. “See that would make sense but you’re not the Big Bad Wolf and I’m not some helpless little girl.” Smirking as Jackson spoke, Drew nodded. He had never been one to fall prey to a bet but this one sounded good. They would both get something good out of it. “I’m fucking ace at blowing, you better start writing your apology emails to whoever you have meetings with now.” Too embarrassed to admit it out loud, Drew liked feeling of Jackson’s fingers on his skin - on his neck - and he wanted to keep it there, keep his touch on him in a strictly non sexual manner but that was asking too much and Drew knew he had already asked for far too much from Jackson tonight. His heart skipped a few beats when Jackson was on top of him. He didn’t know if it was because of the slight hint of fear he’d allow to become present or something else entirely. What he did know was that he liked it, liked how small he felt, liked the tone Jackson was using but his mind was too sluggish, it didn’t keep up with his body’s desires and before he knew it, Jackson was off of him and his cheeks were burning hot. This was too much. They’d only just met. They’d already fucked tonight, Drew couldn’t possibly want more. Keeping silent, he pretended not to feel Jackson tense up underneath him and he pretended that it didn’t hurt. He shouldn’t have expected Jackson to be into it. He’d have to constantly remind himself of that. “I’ll sleep naked next time.” he muttered, fingers brushing against Jackson’s side softly. Completely missing whatever Jackson had to say to him after that, as he drifted off, comforted by the rise and fall of Jackson’s chest.

“You’ve never been out of the country?” Jackson was a little appalled and hadn’t expected that. He’d be traveling abroad before he could even remember. “I have a business conference in Italy next week, I thought it might be too soon to take you. But I’d rather take you than not, I’d be gone four days over the weekend. It might be a good time to get to know each other. I didn’t know if you had school things during that time.” It kind of made Jackson excited to see Drew so excited. He never got to experience new things, so it was refreshing to see him so happy at the thought. “Maybe when we get back we can plan a trip to somewhere you want to go. Just for a couple days, if you’re a good boy while we’re in Italy.” He was relaxed when Drew didn’t seem to get upset over his unemotional response to his confusing confession. “I’m not scared of anything.” He shook his head, very sure of himself. He’d never admit to being afraid of several things, all to personal. Oddly he trusted Drew, but he didn’t have the courage to trust him with that. He zoned back into the conversation when Drew asked about his father. His whole body went ice cold, quickly he took his hands off his chest and felt one of those fears stricken. “I-” Jackson tried, but his throat sealed. Shaking his head, he took a step back. “Don’t ask me that ever again. I made a mistake telling you about myself, never ask about my family ever again.” His voice was cold, clenching his fist to avoid Drew from seeing his trembling hands. Horrible memories flashed in his mind, but he quickly tried to gather himself before giving himself away. “Some people are made for this life and some aren’t. Some are born into it.” He wasn’t angry, he was trying to hid his terror. “You’re lucky to have just enough time in this lifestyle.”

“Fool’s gold?” Surprised that Drew would say something like that, he raised an eyebrow. “I’m an expert in categorizing people. If you were fool’s gold, I wouldn’t have fallen for it. More like a diamond.” He paused, not liking that he seemed to talk himself down. “You’re pretty, for a boy. Probably the most...” His words caught in his throat, not wanting to admit his feelings. “You’re the most gorgeous creature I’ve ever laid eyes on.” He breathed, glancing away. He was trying and that meant sometimes honestly saying things. Just because he was gorgeous didn’t mean Jackson loved him or anything. “You are hardly helpless.” He had to give it to him, the only time he was helpless was when he was falling apart with pleasure in his arms. “We’ll see.” Jackson just wanted to see how good his blowjobs could get. Plus the money he was paying him was nothing compared to his fortune. His measly debt cost him about as much as a watch he might wear once or twice. Glancing down, he saw the sleeping boy, finally. Jackson knew he couldn’t move very far so he grabbed his phone and began working and replying to emails sent from around the world. He had to keep himself awake, even if he was desperately tired from the work out today. A few hours later, he was asleep and his phone dropping to the floor. Only an hour later did he wake up with a loud yell, sitting up instantly and shoving Drew roughly off of him. “Get the fuck away from me!” He practically screamed, still pulling himself out of his nightmare. “Don’t fucking touch me!” Pulling his body into his chest, he let out a noise and clawed at his legs desperately trying to wake up. Once he finally woke up he stood up and didn’t bother checking on Drew as he ran a hand over his face. The sun had just started breaking and there was enough light in the room to see Drew’s outline. Silently he walked out of the room and into his office, slamming his door behind him and hoping he hadn’t witnessed much. This is why he didn’t sleep with people, hopefully now Drew understood why. Walking over to his computer he instantly started working, it was the only thing to keep his thoughts on the present.

[jacksonrossett]

prove it

[jacksonrossett]

wtvrdrew:

“People would get suspicious if I was always here and we can’t have that.” His friends were nosy people, they would have constantly asked him where he was and Drew knew that wouldn’t be good for either of them. “Yes, I do like it but there’s a difference between playing with my hair and messing it up. I take great pride in it, okay?” Drew raised an eyebrow and smirked. “There’s nothing to be scared of.” He shrugged before leaning over to pat his arm gently. “It’s okay though. I won’t let him hurt you.” He smiled, nodding quickly. “I really like you.” He tutted and shook his head. “There goes my plan. I thought I could make a few extra bucks for saying nice things about you.” He frowned when he heard Jackson laugh but quickly hid it. He guessed they both had different views when it came to this stuff - it shouldn’t have been a problem. “Getting married doesn’t mean you’re stupid. My parents got married and they aren’t stupid.” He shook his head and gave a half shrug. “I plan on getting married one day and I’m not stupid.” He licked his lips, looking up at Jackson, knowing that he didn’t want to make things sour, he added, “You know what, it doesn’t matter. I wouldn’t want to marry you anyway.”

“I can deal with a few aches and pains. I’ll survive.” He chuckled softly. “You would just be looking for another excuse to get your hands on me. I get, I’m irresistible.” Drew eyed Jackson carefully. He was finding it hard to believe that someone could have so much money at their disposal. And he was insanely jealous - even if he were granted some access to it, given his current situation. “I feel lucky.” he said. He gave Jackson a playful glare in response to his touching his cheek but he didn’t do anything to get him to stop. He liked the touchiness, he always had. “Let’s just hope you don’t have too many important meetings,” he smirked, biting his lip. “I would hate for you to mess those up because of me.” Drew knew they had a back and forth dynamic when it came to control. He wasn’t exactly the most controlling person around but he did know how to flip things so they were in his favour. It was quite obvious, with the way things were however, that Jackson liked to be in control and Drew would give him that, if he asked for it. “I’m not giving you free blowjobs. I don’t do charity work. I’d get a dog if I wanted to do that.” He smirked at Jackson, quickly winking at him. He decided he didn’t want to think about exactly what he was offering here, he figured ignoring it would make it seem normal in his mind. It would take some getting used to. “Don’t be such a spoil sport man. Are you really going to be an old grump who bitches most of the time?” He raised an eyebrow, smirking. “I don’t doubt that you couldn’t.” Drew rolled his eyes, giving his head a curt shake. He wasn’t too keen on Jackson telling him what he could and couldn’t do when it came to stuff like that.  “Don’t tell me what I can and can’t drink. Don’t be that guy.” Drew couldn’t help but smile when Jackson pulled him closer. He hid his face for a few moments to hide the way his cheeks turned pink before he looked up at him again. “Don’t watch porn while I’m asleep, that’s just gross.” Placing an arm around Jackson’s waist, he shut his eyes, feeling too comfortable with their current position. “Don’t yell at me if it’s bad, okay?” he mumbled. “I’m not a morning person.”

“Just tell them you’re working then. Or tell them to mind their own business.” Jackson had never had anyone really be personally nosy outside of media people. “You will come often though, right? Regardless of your friends.” Drew didn’t seem like someone who would let his friends get in the way of him making money. Not to mention Jackson was pretty cocky, this was the best way for Drew to make money in his opinion. “What happens if I want to take you on a trip to Europe? Will you say no because your friends or family might get suspicious. I don’t plan on going to Italy and not having my company.” He rolled his eyes, Drew was his, he’d be damned if he let other people get in their way. “I really like that mouth of yours.” He commented back, a smirk growing on his face. “I’m not afraid of anyone, trust me.” Shaking his head, his hand shifted down to grab Drew’s ass. “There’s plenty more way to make more money than compliment me. If I wanted compliments I’d just read all those silly magazines.” Which he never paid attention to, he never interviewed for them. They were all lies and assumptions about him, but mostly companies trying to kiss his ass. Jackson’s eyes narrowed, his hand moving up to grab his waist now. “There’s a reason my father never married my mother, never marry what you can pay for. I’m sure you will find someone who will marry you though.” He hadn’t hurt Jackson’s feelings, marriage was the last thing Jackson ever wanted to get wrapped up in. “I prefer relationships like this, the lines are clear and easy. Maybe to people like you, I’m fucked up. But in my world, the one you’re momentarily living in, it’s the only way.”

“Irresistible is a strong word.” Jackson rolled his eyes, this kid was irresistible- it was true. Maybe it was his eyes, or how needy he came across. Physically and emotionally, Jackson was magnetized to him. Not for love or anything emotional, but he did want to be needed. “I’m glad you feel lucky. You’re like Cinderella or something.” He joked, he was anything but prince charming. “Maybe Little Red Riding Hood and the Big Bad Wolf more like it.” Listening to Drew talk about being under his desk was doing things to him, his mind was racing with scenarios. This kid was surprisingly good at seducing him. “You can be under there during my meetings. And if you get me to mess up or stumble over my words, I’ll give you double.” His hand reached up and traced along his neck, oddly entranced with his good looks. “But if not I’ll give you half.” His whole life had been bets, so he was fond of them. Plus this made it into a game, one he was actually unsure he’d ever win. “But if you don’t think you can blow that well then...” He shrugged, retracting his hand from Drew’s soft skin. “Greedy boy.” Jackson chuckled, shaking his head. “Excuse me?” He suddenly rolled on top of Drew, his hands holding him up over him. “Grump who bitches all the time? Spoil sport? You think it’s okay to talk to me like that? I’m not one of your friends.” Maybe he’d been too relaxed with him, but he wasn’t going to be spoken to like that. “You are my employee, my companion. But not my friend and most certainly not in charge here.” Getting off him, he frowned. He wasn’t actually that mad, he just needed to prove a point and exert dominance over him. Taking a deep breath he attempted to relax, he knew he wasn’t fun but he wasn’t going to let some kid treat him like that. Even more so though, he didn’t move as Drew wrapped his arm around him, although he did become rigid. It was one night and Drew wasn’t so bad. “I have to have something that takes my mind off you in my bed, not naked.” Jackson attempted to tease and relax. “I’ll be too tired to yell at you, probably. But I trust in your abilities. Now go to sleep before I get you some cold medicine or something.” He sighed, looking down at him cuddle into him. This is how normal people slept, Jackson hated it.

[jacksonrossett]

prove it

[jacksonrossett]

wtvrdrew:

“If I had known that before I would have chosen a major related to business instead of lit.” He felt instantly relieved by Jackson’s words and he nodded, a little proud of himself in that moment. “I think we’ll get to understand each other the more this relationship progresses. I definitely hope that I’ll get to understand you a bit more.” Drew smirked at that, the idea of having money pleased him - like it would have with anyone who had come from the same background as him. “Maybe I should just move in with you then, that way I’d make money faster.” he joked, chuckling softly. He groaned, taking half a step back while he pouted. “Stop it.” He grimaced at Jackson’s words and shook his head. “Yeah, he wouldn’t be happy. He’d probably kill you for ever touching me. Good man is… one way to put it. I’m definitely not into domineering when it comes to my dad but when it comes to you, that’s a whole different story.” Drew shook his head at what Jackson was saying. “She must be really hot then, if she made you.” He was slightly surprised by the last part of his statement but quickly reminded himself of the world Jackson came from. “Well… let’s hope we don’t end up getting married then.”

“Don’t mention it. I won’t.” Drew shrugged. They probably wouldn’t be talking about caring a lot of the time - they probably wouldn’t be talking about anything a lot of the time, actually - but he was fine with that. He’d have to accept that caring wasn’t a thing Jackson was good at. Drew shrugged, deciding that he was done talking about anything that was too emotion heavy, he’d had enough of that for one night. “No, I only have to worry about my hips and back and other places getting hurt.” he joked, throwing a smile in Jackson’s direction. “You’re lucky the pain is worth the money.” Drew’s breath got stuck in his throat when he felt Jackson touch his lips. He forced himself to not enjoy it too much, enjoyment would only lead to worse things. “I would love to be under your desk, like a good boy.” He bit his lip, heart picking up in speed. “Ah, no, there’s no cheating the system. It’s a one off thing, remember? After this one free one, you’ll have to pay me to use my mouth - or any other part of me.” Drew laughed again and reached over to give Jackson a playful shove. “It’s young people term for making out and stuff while Netflix plays in the background. I’d suggest you start looking up some of that terminology if we’re going to continue with this deal.” He nodded in agreement, stretching out his back for a moment. “I’m all fucked out. Tell your fancy maids, or whatever, to start stocking some Red Bull. I’m gonna need it.” He winked at Jackson and preceded to be caught off guard by the kiss. He liked them more than anything and he figured Jackson knew that. It was just a case of whether or not Jackson knew he liked them a little too much. “Fine.” he groaned, shifting around so his back was to Jackson. He spent a few moments like this before deciding it wasn’t comfy enough and he shifted around again, this time inching closer to Jackson, resting his head gently against his shoulder.

“If you want to be here every night, I won’t stop you.” Jackson shrugged, although he wouldn’t be home every night. The idea of having someone actually home all the time made him uncomfortable- he didn’t really know how he felt about it. But then again, Drew’d be here for his needs. “What? I want to play with your hair, shouldn’t you like that?” Jackson continued to tease. “I’m not scared of your dad.” Jackson said gruffly, eyeing Drew’s lips. He was a little curious of their relationship, but he kept his lips shut about it. “As long as you like me, that’s all I’m concerned about.” He smirked, and ran a hand through her hair. “I’m not going to tip you for complimenting me, you know. But yes.” Jackson chuckled, he wasn’t completely narcissistic but he was proud of his looks. It was something his mom had taught him, but he didn’t go bragging around for it. “My parents never got married, my mom isn’t stupid.” He couldn’t help but let out a laugh. “I don’t think I’d ever marry anyone again. Even if you’re cute.” Not that his ex-wife was ugly, but he found Drew to be one of the most attractive people he’d ever come across. 

“I’ll give you a massage, you’ll be okay.” Jackson spoke up, rolling his eyes. “Sadly medical benefits aren’t part of the deal.” Although if anything ever happened to Drew during their time together, he’d probably help. Who was he kidding? He’d probably rent a whole hospital, but he couldn’t place why. He had to take care of him. “I’ll make everything worth it. That’s the perks of being one of the richest men in the world. You’re a very lucky boy.” His hand moved to pinch his cheek. This touchy stuff was getting oddly comfortable between him and Drew, he wasn’t sure how he felt about it. “Yeah? You’re a really good boy. Daddy can’t wait to have you under his desk.” He felt himself get excited, so he took a deep breath. This kid was easy to flip any of his switches, he didn’t like it. Even if it was amazing sometimes, he liked being in control. “I think staying in my bed is a pretty great tradeoff. My bed is better than yours and your lips are better than most.” Jackson smirked, patting his bed. He couldn’t really imagine being in Drew’s position, he always had money. Not to mention using his body, Jackson wasn’t sure he had the guts to do that. In a way Drew was braver than Jack, but he’d never say that. “Young people term? Do I look like a young person? Why not just say netflix and fuck? I’ll fuck you just as good without knowing your silly terminology.” Jackson murmured, looking Drew over. The sight of him in his bed was strange, and it bothered him how much he felt comfortable with him. He thought he’d hate his body heat, but he didn’t. It was comforting in a way, just how he hoped their relationship would be- oddly comforting. “Red Bull? Fuck that, you’ll have coffee or tea. That stuff is so bad for you.” He shook his head. Feeling Drew get close to him, he reached around and played with some of his hair. Turning his head, he looked at the boy and admired him for a moment. Turning onto his back, he pulled him in to rest his head on his chest. “Go to sleep so I can watch some porn since you’re so tired.” He teased, his hand still resting on the back of his head to play with his baby hairs. “The sooner you’re asleep, the sooner you can wake up and blow me.”

[jacksonrossett]

prove it

[jacksonrossett]

wtvrdrew:

“Massages with my tongue? I don’t think that’s a thing I can put on my resume.” He laughed. “Have I disappointed you yet?” There was a hint of seriousness behind his tone, as if he were actually seeking Jackson’s approval. “I’m pretty sure business classes deal with numbers and I don’t deal with numbers. Unless it’s the zeros in my bank account.”  He frowned, running a hand through his hair. “Don’t do that.” Drew shrugged, knowing how things would go down if Jackson were to ever meet his parents - it wouldn’t be pretty. “You’d probably like my dad though, you’re both very domineering. If only you weren’t fucking his son.” Drew narrowed his eyes. That was… interesting. He didn’t think he’d get to hear much about Jackson’s personal life, especially this early on. He decided he’d be best to make a joke about what he’d said, he didn’t want to push him away. “I would love to meet your mum. Is she hot like you?”

Drew was completely confused by Jackson’s gesture. He was actually hugging him? It was slightly awkward - given everything that had just gone down between them - but it still felt nice. It took a moment but Drew hugged back, squeezing his eyes shut as he accepted the embrace, it was soft gestures like that that he enjoyed, that he wanted. “Thanks.” he chuckled softly. He remained silent as Jackson spoke about caring. It was clear to him that caring wasn’t Jackson’s strong point and that they were incredibly different when it came to it - Drew cared a little too much. “You’re doing a good job.” he muttered. “Not many people try and you are. Don’t push yourself though… I’m not expecting you to always care.” He smiled, shaking his head. “It’ll be better.”  Drew stared at him, feebly following him over to the bed. His words took a few moments to register within him. “It happened over a year ago. It doesn’t hurt that much any more.” He shrugged, unsure what to do when he wasn’t getting the blame for messing up his relationships. Slowly, he shifted up on the bed, moving close to Jackson but not too close - he figured distance between them would be helpful. “It’s a one time thing.” Drew agreed. Even if he didn’t like that, Drew had to remind himself that they weren’t dating, they wouldn’t be doing things like this. He was fine with that now, he’d just have to get used to it. “It’ll be free.” He smirked. “But like with the bed sharing, it’s only a one off. You’re not getting any more freebies.” He scoffed at that, crossing his arms and shaking his head. “Doubt it. I’m brilliant at giving blowjobs. I’ll give you some pointers.” Still smirking, he leaned over to speak quietly in his ear. “Are we gonna Netflix and chill?” Laughing, he moved back into his original position. “I’m just joking, we’ve already chilled tonight.”

“Sure it is, that’s a strong skill in the business world.” Jackson teased, pausing for a moment at Drew’s question. “Disappointed me? No. You’ve been... An interesting ride today, especially for the first day. But I wouldn’t say you disappoint me. We just need to understand each other better.” He was honest and straight to the point. “Stick around here and you’ll have a lot of zeros in your bank account.” Money made him comfortable, he felt in a way he could buy Drew’s happiness with money. But whether that would be proven true or not was a totally different situation. “What? You don’t like me playing with your hair? Too bad.” He reached up and tugged lightly. “Your dad would probably be angry I make you call me daddy, huh? Sounds like a good man, if you like domineering. Which after today, I’d say you enjoy that a bit.” Jackson eyed Drew, wondering how he became the way he was. His curiosity was momentary, he just assumed he was strictly like his mother. “My mom is considered very attractive. They say I got my looks for her, so yes. She was a model he was fucking behind his first wife’s back, in the beginning he paid her.” 

Jackson was grateful that Drew returned his awkward hug, and was even more relieved when he pulled away. His eyes were focused on his lips, wanting to kiss him for some reason. Perhaps his clinginess was already rubbing off on him. “Thank you for recognizing that.” He said, unsure how to respond about the caring subject. It was probably something he’d never perfect. “At least with me you won’t have to worry about getting hurt.” People only got hurt when emotions were involved. He did find himself though, a little disappointed that Drew wasn’t closer to him. He had one night and he chose to lay that far away? “I think you enjoy sucking me off. It’s really a win-win.” Turning to him, his hand reached out and his thumb traced over his lips. “I would love to have you under my desk.” He smirked, pulling his thumb away. “So if I let you sleep in my bed you’ll give me a free blow?” Jackson teased, not sure he could afford to stay up all night every night though. Licking his lips, he had to resist the urge to show the younger boy that he was skilled. But that would be saved for another time he was feeling oddly clingy and giving. “Netlfix and chill? What does that even mean.” He scoffed, turning Netflix on and skimming over a few movies before landing on Pulp Fiction. “We’ve already chilled tonight? So what, fuck?” He raised an eye brow, slightly inching closer to him. “I don’t think either of us have a fuck in us for tonight.” Jackson paused as he looked at Drew in his bed, memorizing the moment. He’d never talked this much before, and he’d only just met this boy. Not only was he intrigued by that this meant, it terrified him a little. Reaching forward again, he pulled Drew closer so he could plant a kiss on his forehead before rolling over. “Go to sleep.” He said softly, pulling his phone back to his face to reply to emails.