Dan was a brat. In almost every sense of the word. He loved bossing people around and feeling better than others and getting his own way, and his wealthy parents had indulged his behaviour until very recently. His father was the CEO of an internationally successful advertising agency, and people had started to talk. His colleagues had gotten wind of the youngest Howell child - his bratty tendencies, his penchant for drugs and alcohol and sleazy sex and all-round debauchery. So not long after his eighteenth birthday his parents had threatened to cut him off. Two arrests and a leaked sex tape later, his parents had followed up on their threats. They bought him a small apartment in the city, and told him he was on his own from this point on. But Dan wasn't phased by this. He knew his parents, they would let him move back home in a few months once they realised he was a hopeless cause. So he carried on living as he had been, partying and hooking up with strangers every night. Once his money ran out he called his parents, but it turned out they were taking a stand and for once sticking to their guns.

Dan wasn't having that. He wasn't going to get a job. He'd be damned if he was going to do what his parents wanted. So he did what any irrational, immature young man would have done in his situation and put out an online ad for a sugar daddy. He was clear and direct about what he wanted. Someone between the ages of 30 and 45 who didn't mind his drink and drug habits, wouldn't mind him having other sexual partners outside of their arrangement, and looked good in a suit. It wasn't long until hundreds of responses were flooding in. A lot of them were from creepy old men or guys who were as broke as he was, just wanting something to fuck. He met up with a couple of people but he didn't really like any of them that much, and they all thought he was rude. He more or less gave up looking and turned to just borrowing money from friends to get high and go out.

Dan woke up one afternoon after a late night out, his head pounding and throbbing, and opened up his laptop. He happened to check his emails when he saw one message from a man called Philip Lester at 7am today.
"Dan,I noticed your ad online about a week ago. I think I may be just what you're after, and you might be just what I need. I would be happy to cover all the costs of a normal week for you in exchange for a purely physical relationship. I would very much like to meet you in person. If you get back to me we can arrange a time and place this week."

He'd added his phone number at the end of the email. Dan frowned, confused. He hadn't provided his email address in the ad, which made it slightly unsettling that he had emailed Dan directly somehow, but something about the message kind of intrigued him. It was more interesting that any other messages he'd gotten that was for sure. After some deliberation he called the number provided. After three rings he got an answer. "Phil Lester speaking." a voice spoke into the receiver. Dan bit his lip before speaking. "This is Dan. How did you get my email address?" he said, cutting straight to the point. He heard what sounded like a soft chuckle on the other end of the line. "I thought I might be hearing from you. Good afternoon."

Dan sighed. "Answer the question." he said impatiently."Now now," Phil's soft voice said. "Maybe you should be a little more careful with the information you share online. It didn't take me long to find you. Now, are you interested in my offer? Or are you just interested in wasting my time?"

Dan was slightly stunned at the abruptness in his tone. "I, um... yeah. I think I'm interested."

"Well are you or aren't you? I'm a very busy man and I'd appreciate a straight answer." He said impatiently. Dan felt himself blush and then, to his horror, he heard himself apologising. "Sorry... yeah. I'm interested." he managed to say.

"Good. How does dinner tonight at a five-star restaurant sound? My treat, of course." The man offered. Dan smiled. This was more like it. "That would be great." he said, biting his lip."Good. If you give me your address I'll come by and pick you up on my way home from work." Phil said, grabbing a pen. Dan gave him his address without hesitating to think how stupid it was to give his address to a complete stranger. Something about Phil's voice was somewhat enchanting. "Okay, be ready at eight." were Phil's last words of the conversation before hanging up.

Dan spent the rest of the day smoking weed and watching cartoons until it was time to get ready for this fancy dinner. He had a shower and did his hair before getting dressed in his tightest pair of jeans which he knew made his ass look great, a thin plain white cotton shirt, a black tie and a leather jacket. He got a phone call just as he was checking himself over in the mirror. It was Phil, saying he was waiting outside. Dan checked he had everything and went downstairs, seeing a BMW with blacked-out windows in the parking lot. It was the only car in sight so he headed towards it, opening the passenger door and getting in, looking over at the handsome man in the driver's seat, with dark hair and wearing an expensive-looking suit. "Are you Phil Lester?" he asked uncertainly.

The man smiled softly and nodded, reaching out to shake his hand. "And you're Dan. I recognise you from your pictures." he said, giving a firm confident handshake. "It's nice to meet you." he said as he began to reverse out of the car park with ease before speeding off down the road. He glanced at Dan's block of flats in the rear-view mirror as they drove off. "Well if this works out, first order of business will be to get you a new apartment somewhere far away from here." he commented. "I, uh... really?" Dan asked, a little taken aback. "Yes." Phil said simply, looking over at Dan. "My career and the people I work with expect me to uphold a certain lifestyle. That would have to include anyone I'm romantically involved with." he said casually, turning on the radio. Dan wanted to say something but didn't. He took the radio as a sign that that discussion was over, and they drove in silence the rest of the way to the restaurant.

Once they were seated, they were handed their menus and Phil asked the waiter to give them a few minutes. "I don't know if you want to drink tonight? I'm driving so I won't be, plus I don't want to risk forgetting any details of tonight, but you're welcome to. I could order a bottle of wine?" Phil offered, looking down at the menu rather than up at Dan. Dan nodded, deciding he'd definitely need some alcohol to calm his nerves and to generally get through this night. He didn't know why he was nervous - he hadn't been for any of his other meetings. Maybe it was because he actually liked Phil and he was attractive and smart and seemed interesting. "Yeah, a bottle of red would be good." he said, looking over the wine list. "Do you have any recommendations?" Phil smiled and nodded, pointing to the most expensive wine on the menu. "You'll love it." he said, calling over a waiter, ordering a bottle of the wine for Dan and just some water for himself."So, what do you do for a living?" Dan asked the man, who remained something of a mystery.

"Oh, I'm the director general of a major TV network in the USA." Phil shrugged, looking up at him. "Most of the work I do is done remotely, we have meetings via skype and such, but I do have to travel to LA every few months. I have a second home out there." He smiled sweetly at Dan. "What about you?"

Dan was slightly taken aback at Phil's answer, which he had so casually given. "Um... well I was living off my parents until recently..." he said after a moment. Phil raised an eyebrow and looked down at the menu. Dan panicked, worried he'd given off the wrong impression. "I mean, I was living with them, but then my dad decided he was going to put his reputation in his career over his son, so they cut me off." Dan said hastily. Phil still said nothing. "My dad's the CEO of a big advertising company, and I got into some trouble for doing drugs and people he worked with heard about it. He gave me a warning that he was considering cutting me off... then I got arrested a couple more times... and then my ex boyfriend leaked a sex tape of us and there was this big scandal, and then he did cut me off. Then I ran out of money so I started looking for someone like you..." Dan was rambling at this point. Phil was showing very little reaction, hardly listening, until this point, when he laughed quietly. Dan frowned.

"Dan, I know. I did plenty of research on you. That's how I got in contact with you." He said, looking amused. "I know all this. I've seen the tape. I've also met your dad in person." he laughed softly, and continued chuckling quietly as the waiter brought over their drinks. Dan blushed scarlet, picking up his glass of wine. He opened his mouth once the waiter had left. "What... how..." he said, eyes wide. "It wasn't very hard to find the video online. It seems it's become very popular, and now I understand why. As for your father, me and him have done business together in the past, I met him again recently at a conference. He really is looking worse for wear these days. I suppose the stress of having you as a son got to him." he smirked.

Dan bit his lip, looking down at the table, suddenly feeling guilty, which wasn't a feeling he was familiar with. "Can you give me a minute?" he asked quietly, getting to his feet and walking towards the bathroom. He groaned, running his hand through his hair and trying to settle himself down. He pulled out a little bag from his pocket, doing a line of coke off of the counter. He screwed his face up and rubbed his nose, before heading back to the table. He felt a little better, more alert. He sat himself down and smiled at Phil. "I ordered for you, I hope you don't mind." Phil said, smiling at him. Dan nodded, sipping at his wine. He wasn't massively hungry anyway.

"So, this arrangement you proposed." Dan said, looking up at Phil. "What would it specifically entail?" Phil smiled, nodding. "Well, for you, I'd like you to be available whenever I require. But I'll explain that more in detail later. As for my end, I'd spoil you, pay your rent, buy your clothes, your drink, your drugs, anything else you want or need. I don't mind the substance abuse so long as it doesn't get in the way of you holding up your end of the deal." Phil shrugged. "How does that sound?"

Dan smiled softly. "That sounds perfect." he nodded. They spent the rest of their meal getting to know each other a little better and Dan ended up having quite a nice time despite his earlier nerves, thanks to a bottle of wine. He learned that Phil had just turned thirty and that he grew up not far away from where his parents had got married. He was feeling relaxed by the time the cheque came, trailing a finger around the rim of his wine glass. "So, you said you'd explain things in detail later. Is this later?" he asked, with more confidence than he would have spoken with at the beginning of this meal. Phil smiled gently, pulling out a handful of notes from his wallet and putting it down on the table to pay for the meal, along with a generous tip. "It's probably best we discuss it somewhere less public. Would you like to see my place?" he asked, getting to his feet and putting an arm around Dan's waist when he noticed that the boy was a little unsteady on his feet, walking with him out to the car. Dan smiled softly at the touch. They drove most of the way to Phil's place in a comfortable silence.

The car drew up to a set of large gates, which opened as the car approached. There was then a long driveway leading up to a large modern-looking house, with lots of balconies and floor-to-ceiling windows. Dan smiled as he got out of the car and Phil lead them up to the front door, letting them in. He gave Dan a brief tour, culminating on a balcony overlooking the garden, which must be several acres worth of land. There was a bar and a few comfy-looking chairs. Luckily it was a warm summer's night, and the temperature was just right. Dan took off his jacket and loosened his tie, looking out over the garden. "Drink?" Phil asked, distracting Dan from his slight daze. Dan turned around, shaking his head. "I probably shouldn't." he smiled. Phil nodded, pouring himself a gin and tonic. "Anything you do want?"

Dan raised an eyebrow. "Could do with some coke." he said, reaching into his pocket. Phil chuckled. "Go ahead." he said, gesturing to the marble-topped bar in front of them. Dan shrugged, setting out two lines of coke and doing them both. He straightened up, his eyes rolling back into his head, a lazy grin on his face. When he focused his eyes back onto Phil he saw him smirking as he watched Dan, sipping his drink. Dan giggled, moving to sit down on the bar."It's been years since I've done coke." Phil said. Dan was taken aback by the statement. Phil laughed at Dan's expression. "I used to do it when I was your age. I was a lot like you actually. But I got a job and had to dial it back, grow up a bit." he smiled, pushing some of Dan's fringe out of his face and tilting his chin up so Dan was looking him in the eyes.

"Anyway, about this whole arrangement thing. I get pretty lonely, and pretty horny, and I could do with someone like you around. I'll give you a call when I need you, I'll send a cab to collect you, all you need to do is get in it. Does that sound like something you can do?" he asked, and for once Dan noticed something a little bit like concern on his face, which didn't seem to fit his generally confident and commanding demeanour. "I want to make sure this is all completely consensual. Don't think just because there's money involved you're not allowed to say no to anything, okay?" Phil said, running a thumb down the side of Dan's face and cupping his jaw gently. Dan smiled and nodded. "Got it." he said, biting his lip. Phil chuckled, running his thumb over Dan's bottom lip. "Good. Now, you've seen that I have the means to hold up my end of the deal. Let's see if you're up to holding up yours." Phil said, surprising Dan by kissing him tenderly, only for a few seconds. "No need to look so worried." he said, taking Dan's hand and leading him inside and up to the bedroom.

It was huge and Phil had a massive, comfy-looking bed covered in throws and pillows. One wall of the room was made up entirely of glass windows, also overlooking the garden, and there was a small balcony just outside. There was a large mirror opposite the bed, and Dan smirked at the sight of it. Phil closed the door behind them, then sat himself on the edge of the bed, looking up at Dan. "Now, Daniel." Phil said, noticing Dan seemed a little distracted. "I have a... specification that I like my partners to meet, which you seem to meet so far. Now... if you don't mind taking your clothes off." he said, his tone completely casual. Dan blushed but did as Phil asked, taking his tie off and unbuttoning his shirt slowly. "I didn't ask for a strip tease." Phil said suddenly, rolling his eyes. "We don't have all day."

Dan blushed an even deeper red, feeling humiliated... but also somewhat turned on by Phil's tone. He quickly got his shirt off and wriggled out of his skinny jeans and boxers. His cock was already hard, and Phil smirked at the sight of it. He stood up, walking around Dan, taking him in, inspecting him almost. Dan stayed quiet, staring down at the thick carpet he stood on. "I'm glad to see you're enjoying yourself." Phil was stood in front of him now. He lightly wrapped his hand around Dan's erection, running his thumb over his slit, chuckling as Dan gasped and stifled a moan. He removed his hand and tilted Dan's head up to look at him. "Remember you can say if any of this makes you uncomfortable, and I'll stop." he said, with a reassuring smile before smacking Dan's ass with surprising force. "On the bed, on all fours." Phil said, and Dan rushed to do as he was told.

He never anticipated that he'd enjoy being ordered around as much as he was. In every other facet of his life he despised it, but something about this situation was making him unbelievably excited. He could hear Phil's footsteps walking away, pausing, then approaching him again. He felt a hand on his lower back, then another on his ass, feeling one lubed finger slowly push into him. "I'd heard you slept around a lot?" Phil said, the question seeming to come out of nowhere. Dan nodded uncertainly. "Yeah, I guess..." he said quietly. Phil made a small noise of approval. "Hm. I wouldn't have thought you'd be this tight." he commented, moving the finger slowly in and out of him before adding a second. Dan groaned softly, closing his eyes. "When was the last time you were tested?" Phil asked, still slowly moving his fingers in and out. Dan tried to focus, frowning a little. "About two weeks ago." he murmured. "And how many people have you fucked since then?" Phil asked, finding Dan's prostate and gently stroking the tip of his finger against it. Dan let out a loud moan. "A-About five." he managed to choke out through the pleasure. Phil let out a quiet laugh before suddenly pulling his fingers out. "Good. I'd like it if you could go and get tested as soon as possible, preferably tomorrow. Just to be sure." he said, patting Dan's thigh gently. Dan nodded, glancing over at him. Phil smiled and kissed him gently. "I'm completely clean. Haven't had many partners lately, but I still get tested regularly. You're welcome to ask my doctor himself if you want to double check." he smiled reassuringly, and Dan just nodded slowly. "I'm going to wear a condom this time, just to be safe, but I won't be after this if we go ahead with this arrangement." he said simply, tugging Dan to his feet.

"Now, you've given head before, right?" he asked, and Dan nodded quickly. Phil smirked. "Well, I knew that. I've seen the video. But still, it's polite to check." He gave Dan a smug grin. Dan knew how to take a hint and dropped to his knees in front of Phil, unbuckling his belt and trousers. Phil smirked. "You enjoy sucking cock, don't you?" he said, watching as Dan stared at the large bulge in his boxers. Dan just nodded slowly. Phil pulled his half-hard cock out of his boxers, and Dan licked his lips, quickly wrapping one hand around Phil's length, starting to lick and suck at the tip. Phil watched him, looking pleased. Dan could already feel Phil hardening further in his mouth, and took this as encouragement, stroking him quickly. Once Phil was completely hard he pulled off, pushing his hair back out of his face and starting to suck lightly at the tip. "If I wanted to be teased I'd tell you." Phil said from above him, before grabbing a handful of Dan's hair and pushing himself further into Dan's mouth and the back of his throat, until Dan's lips were at the base of his cock, nose pressed against Phil's abdomen.

Phil loosened his grip somewhat and Dan pulled back breathlessly, then immediately went straight back down. Phil smirked, watching him work away. Dan was transfixed, focused entirely on pleasing Phil, occasionally choking or gagging but not letting it put him off. Phil was moaning quietly above him, hands still lightly gripping Dan's hair. Suddenly Dan felt him pulling back out of his mouth and whined, moving forward to keep sucking him off. "Dan." Phil's voice said, quite sternly. Dan slowly pulled off and looked up at Phil, panting, looking slightly dazed. Phil smirked at the sight of him; mouth wide open, eyes glazed, his lips cherry red and slicked with spit, a string of either precum or saliva connecting his bottom lip to the tip of Phil's cock. "You really do love sucking cock." he chuckled, making Dan blush again, suddenly feeling self conscious.

Phil grinned, pulling Dan to his feet and guiding him towards the bed. Dan got on his hands and knees again, back arched, his ass sticking out towards Phil. "Stay still." Phil said quietly, having an idea. He pulled the bag of coke out of Dan's discarded jeans on the floor. "I'll pay you back for this." he said, setting out a line down Dan's spine. Dan realised what he was doing and grinned. After a minute or so he felt the warm presence of Phil positioned behind him, his tip nudging Dan's entrance before slowly pushing in. Dan moaned and shuddered at the sensation. Phil was bigger than anyone he'd taken in a long time. Phil pushed in all the way before slowly pulling back, starting up a steady rhythm.

Dan groaned, then let out a sudden noise between a gasp and a whimper as Phil slammed into his prostate. Phil chuckled at his reaction, watching Dan squirm as he stayed pressed against that spot. He smirked, grabbing a rolled up note and snorting the line from the nape of Dan's neck down his back. He groaned as he drew back, starting to fuck Dan again, now moving faster than ever. "Jesus. We need to get you a new dealer." Phil said as he pounded into Dan, who was hardly paying attention. "Huh?" he mumbled, confused. Phil laughed. "I don't mind you doing coke but I don't want you doing that shit. Who knows what's mixed with that." he said. Dan simply nodded, moaning and stroking himself along with the rhythm of Phil's thrusts. Phil moaned, grabbing Dan's hair and pushing his face down into the pile of pillows in front of him, hearing his muffled moans.

Before he knew it, Dan was coming onto his stomach and the pristine white sheets beneath him, whimpering and convulsing as he released, coming harder than he had in what seemed like forever. Phil didn't stop however, kept pounding away at Dan's almost unbearably sensitive prostate for another fifteen minutes that felt like much longer before coming hard into the condom, slowing his thrusts down until he had finished completely. He slowly pulled out, causing them both to moan softly.

He tied a knot in the condom and tossed it in the direction of the bin before flopping down onto the mattress besides Dan. Dan looked over at him breathlessly, his hair tousled, pupils wide. Phil grinned, kissing him softly. "Did you enjoy that?" he asked, smoothing Dan's hair down, and Dan nodded eagerly. Phil smiled approvingly. "Yeah, it was fun. Do you want to stay the night, or would you rather go home?" Phil asked, still stroking his hair. "I'll stay the night." Dan murmured, as he was exhausted. Phil nodded, reaching over to grab a wet wipe from his bedside table, cleaning Dan off a little before pulling the covers on top of them. Phil sat up against the headboard, feeling alert and awake. Dan smiled, curling up next to him and closing his eyes.