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It wasn't too often that Stiles got to do his work in classy locations. The people who wanted someone like him usually had him doing in house visits to lonely house wives or taking people looking for something naughty but not too shady to swinger clubs. He knew how he looked, took advantage of it even. Thankfully he'd dressed to fit the occasion in his nicest I'm Totally Not A Hooker clothes so he made it to the front desk without getting tossed out with security.

"Hey there," He leaned on the front desk for all of five seconds before the look the receptionist gave him had him straightening up. "I've got an... apppointment with Mr. Whittemore up in the luxury suite. Can you call it up to confirm?" The pursed lip look didn't go away but she picked up the phone and turned away from him. Looks like they didn't want to risk offending someone who was throwing money their way. Good to know.

All too quickly the receptionist hung up and gave him terse directions to the floor and room he'd want. "Thanks. And don't worry, I'll be gone in the morning. You won't even know I was here."

A short elevator ride later, Stiles was knocking on a door that probably cost more than his entire apartment combined. Who the hell put gold leaf on a freaking door anyways?

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Jackson hung up the phone and stared at it, lost, wondering how he'd gotten to this point. Was he really going to go through with this?

He made the call on a whim.

He'd gotten the business card from a guy during a party a month ago. "In the unlikely case you ever change your mind. Give this number a call and ask for me." And Jackson could still remember the way his lips felt on his.

Jackson was halfway through a bottle of southern comfort when he made the call, asking after the man he met, only to find out he wasn't available until the next evening, and Jackson would have hung up with the intention of never calling the number again. But the tumbling thing of his chest - his stupid fucking heart, which lost any right to make any decisions at all - didn't want to be alone.

"Then send whoever's available. As long as he's reasonably attractive."

What counts as reasonably attractive anyway, Jackson thought drunkenly with his head tilted back into the armchair. It wasn't like there were a set of pictures to choose from. He'd never been with another guy before. It wasn't like he didn't know the mechanics. He'd seen enough porn to know how it worked, only he never expected to pay for it. Too much pride, maybe. Not enough courage. He'd fucked up his chances. He guessed fucking a guy in exchange for money would be one way to make it all worse.

A knock on the door interrupted his morose thoughts, and Jackson rose from the chair with his tumbler in hand and made his way over to the door.

He opened it without any preamble and was mildly confused for a moment when he saw the person standing there. He'd been expecting someone like the man he'd met before - broad, muscular, handsome - not this guy. He looked almost as young as Jackson, if not younger. Short hair, brown eyes. Compared to Jackson's disheveled formal clothing, the guy looked like he walked out of a JC Penny cataogue.

Jackson frowned. "Do you have the right door?"

It was a surprise, having a client nearly his own age staring him in the face. Not that he minded, not with the parade of recent clients he had. Taking the baby faced escort for a spin was a way to feel young.

"That depends," he said. "If you're Jackson then I've definitely got the right room." He smiled like he meant it, even though the smell of southern comfort made him want to wince. "I'm Dirk." It had been his own private joke when he'd joined the agency. Choosing a name as close to Dick as possible without actually naming it that. No one else seemed to appreciate his humor.

"I'm your... date for the evening."

There was a brief pause while he considered what to do. He looked "Dirk" up and down and while he wasn't exactly lacking, he wasn't what Jackson would call impressive either. In the end, Jackson was altogether too drunk to really give a shit one way or the other and shrugged, turning to wander back into the suite he'd rented for the night, leaving the door open for the guy to follow him in.

"I'm not calling you Dirk," Jackson said as he plopped back on the armchair he'd been keeping warm, not spilling a drop of his liquor despite being less than well-coordinated. He should probably slow down if he wanted to perform. "That's a stupid fucking name. Make up another one. And make it believable this time."

Edited 2014-03-14 03:02 (UTC)

That familiar urge to snap out something biting was on the tip of his tongue. Stiles barely managed to swallow it down with the reminder that a job was a job even with a drunk jackass calling the shots. If anything he'd just have to take a good look at the guys credit card just in case he got rough.

Shutting the door behind him, Stiles looked around the suite carefully. "Yeah, sure. How about Stiles? Or Scott or maybe Nick. Or call me whatever you want since you're the one paying for this."

"Also it'd be cool to know what you want to do so I know how much you're paying up front."

Edited 2014-03-14 04:06 (UTC)

Jackson let those names roll around in his head. "Stiles," he decided after a brief moment of consideration, taking one last casual swig before setting aside the tumbler on a side table. "Why not? It suits you."

It was an odd name for an odd person he hadn't expected.

He pointed at the envelope on the table. "Your money. They did say you liked your payment in cash." He added, a little dryly, "Do you want to count it first?"

It was hard not to swear, he never should have used his actual name. There was always a careful boundary between his normal life and his night work and keeping his real name out of it was key.

"No need to count, I'm a classy escort you know." He was itching to make sure it was all there, but kept the urge down. The company always got a credit card number before anyone was sent out in case shit happened.

Stiles sauntered over and sat on the arm of the chair Jackson was sitting in, all smiles now that his time was paid for. "So what did you have in mind anyways? Just keep in mind I don't do anything without protection and you get much rougher than a spanking and you'll be getting an extra charge on your bill."

Edited 2014-03-14 04:38 (UTC)

Condoms were a given - and not just because Stiles was an escort. So Jackson shook his head in agreement on that point, but looked up with a questioning (and slightly intrigued) expression at the mention of spanking.

"We've only just met," he replied, in that practiced flirtatious way when he was meeting people's daughters for the first time. It meant nothing, easy to discard, and he had to grimace at how automatic it was. "I'll take a rain check."

From this angle, Stiles looked competent. Pretty, kind of. Or maybe Jackson was just drunk on southern comfort and wanted a comforting thought like that. Who the fuck knew anymore. He had a hooker with a dick in his suite, might as well make the most of it.

He climbed up off the armchair, unmindful of how he brushed up against Stiles, and padded barefoot towards the bedroom.

"Grab something to drink if you want, I'm the one paying for it, right?" He waved vaguely at the fully-stocked bar as he began shedding his dinner jacket. He could still taste the champagne and the sour bite of congratulations. "Or follow me into the bedroom and we'll figure this shit out."

Edited 2014-03-14 12:57 (UTC)

"Cool." Stiles stayed back for a moment and glanced over at the open bar, more than a little tempted but he had rules for himself along with the ones he set down on his appointments. Not taking anything that could alter his judgement before he finished with a client was big. Maybe once he'd finished up he'd take a bottle with him as a souvenir. Because if this was how the big spender was going to act he was going to fucking earn it.

Following Jackson into the bedroom, he pulled off his own jacket, dropping it carelessly near the end of the bed. It was nice that Jackson was hot, an unexpected bonus in his night time activities.

"So how do you want to start out? Your wish is basically my command, dude."

He slowed at the question, in the process of loosening his tie, and wondered what exactly he wanted to prove. That he could take it? Or that he could take what he wanted without having to apologize for it? The thought had Jackson turning away, if only because the memory of the dinner party he attended still sat a little too close for comfort.

"You can start by not calling me dude," he answered as casually as he could manage. He threw his tie over the back of a chair carelessly and quickly began working on the buttons of his shirt. "It's Jackson."

He glanced over his shoulder. "And losing your clothes."

"Right. Jackson." Prettier than most of his clients, still kind of asshole. And still paying for a lay instead of using his pretty face to get someone for free. That definitely said something.

It didn't take long for Stiles to strip off his t-shirt and unbutton his pants enough to be a tease. It wasn't like he was built like some of the guys at the agency but he did well enough going by client numbers.

"I could help you with yours, too." He said, tugging at the collar of Jackson's shirt. "I'm guessing you haven't done something like this before, so how about I help you get warmed up?"

He was halfway through the buttons on his shirt, fingers slow from the amount of alcohol he'd consumed since he left the restaurant. If he'd been sober, his shirt would've already been hanging on back of the chair with his tie by now. But of course he wouldn't be doing this if he wasn't drunk. (Another thing to add to the coward column.)

And then Stiles tugged on his collar, dragging Jackson out of his own head.

There was a brief pause before he nodded, despite the juvenile part of him that recoiled at having any kind of inexperience called out on. He pushed it back down, not having the energy to make an issue of it - Why bother denying what was true? He let his hands fall away and turned to face Stiles, leaving the rest of the buttons to him.

"I haven't," he admitted, because drunk Jackson talked a little more talkative than sober Jackson. "Never had to pay for it either. First time for everything, I guess."

"If you're expecting judgement you're talking to the wrong guy," Thankfully his own fingers were much more nimble and he had Jackson's shirt undone a few moments later. "What with this being my job and all."

The shirt met the floor and Stiles hooked his fingers into the waistband of Jackson's pants for a moment before dragging his undershirt up and over too. It really wasn't fair for a guy to be this pretty and also be rich. It wasn't like the agency was cheap with its rates, especially on unscheduled appointments.

Then it clicked what Jackson meant. He'd never been with a guy before. Oh shit, that was new. And though he'd never admit it outside his own head, kind of hot.

"So I'm guessing you've never gotten head from a guy before?" He slid down to his knees with a grin and worked on the fly on his pants.

Jackson blinked, surprised at being surprised to find Stiles kneeling in front of him, before the rest to the conversation caught up with him and left him sucking in a deep breath through his nose.

He shook his head slowly as he watched him work his dress pants open. If his dick hadn't been interested before, it certainly was now. It wasn't like Jackson could honestly say Stiles wasn't attractive, because he was, even more so on his knees.

"Only girls," he replied, voice low. "Thought about it, though."

He should really shut up. His brain to mouth filters were obviously MIA.

He was so screwed up, that this was actually turning him on.

It was gratifying tugging his boxers down and being greeted with a hard cock and he rewarded Jackson with a few slow strokes. It was tease, a warm up that let him get an idea what he was in for. Stiles liked what he saw. He licked his lips for a moment and fumbled for a condom with his free hand.

"Lucky for you, I've gotten pretty good at this..." He ripped open the condom wrapper with his teeth and without any warning set about applying with his mouth.

It felt like his brain kept skipping, like there was a second long delay from what he was seeing and feeling. This was turning out a lot differently than he'd been expecting. In a good way, definitely a good way. The strokes had felt good but they were nothing compared to when Stiles rolled a condom on him with his mouth.

His breathing stuttered, brain suddenly blank. His dick was in another guy's mouth. A hand was still a hand and mouth was still a mouth, right? Or at least that had been his reasoning a moment ago. Now Jackson knew better.

He pressed his lips tight together to keep himself from making other sound noise. His hand slid easily into Stiles' short brown hair without him noticing, more focused on the slick sensation of the condom and the more inviting pressure of Stiles' mouth.

"Bed," Jackson whispered distractedly, suddenly harder than he's ever been in his life. He also really needed to sit down. His body couldn't handle being drunk and getting a blow job at the same time. "Don't think I should be standing for this."

The smug little part of him that enjoyed his job knew that he'd done good when he felt Jackson's cock jump and get harder in his mouth. Nothing like a job well done. It took a moment for the words to register. Another altogether to resist the urge to take him all the way to the root right then and there just to see if Jackson's legs might give out on him.

This job had given him weird reactions.

"Yeah, sure." Stiles guided him back to sit on the bed and took the chance to get rid of Jackson's pants entirely. Much better. He ran his hands along Jackson's thighs, resisting saying a million things that would probably get him kicked out. He ought to get a tip just for his restraint but there was never a bonus for not being a dick.

He licked up the length of him quick before looking up at Jackson. "Just tell me if you need me to stop before you come, or if you can handle two rounds." Then without any preamble he was wrapping his lips around the tip and sucking.

Jackson got comfortable on the bed, letting his legs fall open and leaning back on his hands to give Stiles room to work. It was a miracle he managed to stay upright, mostly because he wanted to see Stiles swallow him down.

He had a feeling he could come from just this blow job. Some of the girls he'd been with had to work twice as hard to get him off, most couldn't, even when he was relaxed and loose like he was now. Their jaws got sore too soon for he to work himself up to that point. It said something but Jackson had gotten much too good at ignoring it.

"I could go for two," he panted lightly as his hips twitched. "If you fuck me afterwards."

Yeah. His filters and inhibitions were definitely on extended vacation.

If you fuck me afterwards.

The line was like an electric shock down his spine leaving a pit of heat building in his stomach. It was one thing to get it up for a job, another to want one of his clients this badly. Stiles honestly couldn't remember the last time that had really happened. And he wanted to make sure he blew this guy's mind so he'd maybe come back for more. Stiles looked up at him, made sure Jackson was watching real closely before he took Jackson's dick all the way to the base.

He swallowed around him once and then pulled back, only to repeat the move. One hand stayed on Jackson's hip to make sure he didn't choke him by bucking his hips up too fast. You only let that happen once before making sure never again.

It wasn't as thought Jackson could look anywhere else, rapt as he watched Stiles take him all the way into his mouth - And why was the hotter than anything he'd ever seen, how easy Stiles made it look? It wasn't even remotely comparable to the times he'd gotten head from girls. The mark of a professional, maybe. Fuck if Jackson knew.

He couldn't stop the faint tremble in his legs when Stiles deep-throated him, letting himself fall back on the covers with a drawn-out groan when it happened a second time. It felt so good.

"Fuck," Jackson gasped out. His hips gave an abortive jerk but surprisingly, he listened to the way Stiles' hands were telling him to keep still. It wasn't long before he was pushing himself back up on his elbows, not wanting to miss the way Stiles' lips looked stretched around his cock or how he would look blowing him.

The rhythm is easy to fall into, hollowing his cheeks and making sure not to falter. Maybe it had been harder once but Stiles had quickly caught on that sucking someone off was as much about the presentation as the actual performance. So with his lips still wrapped around Jackson's dick he moans, a good quality one. Not a cheap porno moan, he'd figured out that no one actually bought that in real life. It wasn't entirely faked, just enough sound quality to get the point across.

The part Stiles didn't want to admit was that it was more genuine than usual.

Maybe as a distraction, or a warm up for things to come? Stiles pressed a hand to his own painfully hard dick as he worked Jackson as best he was able. He was starting to feel a bit desperate himself, the eagerness to fuck Jackson was building the longer it took to get him off.

It wasn't the first time Jackson heard or felt someone moan around his cock, and maybe it was fake, maybe it wasn't, but he was beyond thinking about that now. All he had left in him was fast, panting breaths and drawn out moans. Stiles made it look good, like there was a reason he did this for a living. He flopped on his back again, reaching down to touch the guy sucking him off, needing another connection that just wasn't Stiles' mouth on his dick.

And maybe it was because Jackson was drunker than he normally let himself get, but it wasn't much longer before he felt the edge of orgasm within reach.

"Stiles -" He gasped the name out and full-body shuddered, hand twisting into the sheets to avoid pulling on Stiles' hair. "Fuck, I'm going to -" It was a good thing he was wearing a condom because his orgasm hit him hard enough for him to choke on the word come.

Keeping his jaw relaxed, Stiles swallowed around Jackson's cock until it was spent. When it was done, he pulled back and wiped away the saliva that had gathered on his chin. Jackson looked well and truly wrecked for the moment so he took care of cleaning up the current mess so he'd have a minute to recover.

"You still alive, sunshine? We're not done yet, unless you changed your mind."

Everything properly cleaned up, Stiles returned to the bed and settled himself next to Jackson.

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