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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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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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