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Best Night

Chapter Text

Stiles absently picked at the cuff of his sleeve and looked the advertisement over again as he had been doing for a week now.

It was small, discreet, hidden in the back pages of the paper and it was for an exclusively male escort agency called Alphamales. He snorted at the name as he imagined burly suit types with no body hair. And male escort? Wasn’t that what they called a glorified male hooker?

Probably not but then again Stiles would actually have no idea. It wasn’t like he was experienced in these types of things. When he had first seen the ad he had laughed a little, not paying it much attention but over the past week the advertisement kept bugging him, it was constantly at the back of his mind and he couldn’t help but memorise the number.

Was is weird or freaky or completely pathetic that he wanted to call and get himself a ‘male escort’. Stiles bit his lip. He knew he was gay, he was fine with being gay. Gay was great. It was the actual sex he was having trouble with, actually the lack of actual sex, with him and someone else. Not just him, some porn and his right hand. And maybe some lube.

So yeah, he was a 21 year old gay virgin.

Not that that was a bad thing in particular, not at all, in fact he liked that he had saved himself. But then again he wasn’t really sure he had. It wasn’t like he’d had enough boyfriends to say he had actually saved himself or any boyfriends really. A few drunken hook-ups that hadn’t gone much past groping were about the extent of his experience.

He was just running out of faith that he was going to find ‘the one’ or just someone he loved to get it out of his system and now, well now he just wanted not to be a virgin anymore.

So yeah, back to the escort agency. He was tempted to ask Scott whether he should do it or not, but no, Scott would probably tell him to go out and get laid by some random stranger, which was not only stupid but pretty dangerous. Or worse Scott would talk him out of it, telling him that ‘he should wait’ or that ‘he would meet someone one day’.

God that made him pissed off. He hated it when he’s happily couple friends said shit like that. It’s almost like they’ve forgotten what it’s like to be single and keep spouting the same bullshit to him, bullshit that gets him nowhere.

And he knows they just want him to be happy. He knows that but just because they found their happily ever after doesn’t mean ‘ol Stiles is going to.

In fact at this rate ‘ol Stiles is probably going to end up at age 60, still a virgin and owning a thousand cats. Or worse and become a hoarder and then Scott would get the horrible show to clean out his house and Stiles would have to rave and rant to keep a pile of Tupper wear lids insisting that they just ‘might come in handy one day’.

Stiles shuddered. Nope that wasn’t happening to him. At least if he does this, rings this agency then he might die a lonely old man with a thousand cats, but at least he wouldn’t be a virgin. Score for Stiles.

It was times like this that Stiles was glad he moved out of home last year. Not that he didn’t love his dad, he just wasn’t sure how happy he would be to find his son in bed with a hooker, Ahem, male escort, (Was there a difference, Stiles should probably find that out).

It wasn’t like he wasn’t going to do this. He was organised. He had condoms and lube (strawberry flavoured) and he’d had about four showers. It was just the calling he was freaking out about. Despite the fact he was an adult, he still sweated buckets over calling anything that was vaguely adultey. And this was worse, much, much worse than calling the phone company up about your phone bill, because this was calling, asking for sex, with someone who gets paid to have sex for a living. Stiles wavered a little, did he really want to get de-virginilised by someone who gets paid to sex people up? He was being judgmental, again, there were plenty of people out there who had loads of sex with loads of people and he didn’t judge them. Escorts were just smarter and more honest, well Stiles supposed they had to be; at least they got paid to have sex.

He knew he was stalling. He knew he was trying to put this off. But he’s made up his mind a week ago. Actually he had made up his mind the moment he saw the ad, he was sick of constantly being the lonely pathetic virgin. At least after this he’d be only be lonely and pathetic.

He swallowed a lump, grabbed his phone and called the number jumping in shock when it answered straight away. In fact he dropped his phone, hastily grabbed it up to hear the last of the answering spiel.

‘…Alphamale Escorts. How can I help you?’

The voice was vaguely familiar, but he couldn’t place it.

‘I’m uh, I’m looking for an escort.’

‘Well, you’ve come to the right place. Was there anything in particular you were after.’

Stiles blushed, even though he knew no one could see him, he couldn’t help it, ‘Well I’m uh- well I’m rather sexually inexperienced, so uh-’

‘-Virgin?’ the woman on the end of the phone asked briskly. God dammit her voice was familiar.

‘Yes.’ He mumbled, still embarrassed with discussing his sexual history or lack thereof with a complete stranger.

‘No problem, we have a guy who specialises in virgins. I’m sure Isaac would be pleased to help out.’

‘Great, that’s uh, great. Specialises? Does that mean he does a lot of de-virginilisations? Not that I care really coz it will just mean he’s better at it than others I suppose. Or gentler maybe? Because how does that work? Who’s the little spoon and who’s the big spoon? Who decides?’

The lady coughed over a laugh, ‘Well usually you guys discuss that together when he gets there. And it’s called topping and bottoming. So when did you want…’ then she tailed off, silent on the end of the phone.

Stiles waited for her to continue and was almost about to ask if she was still there when she coughed again and asked quietly, ‘Stiles? Is that you?’

His stomach dropped. Shit, apparently familiar woman knew him too. This was just incredibly embarrassing, extremely mortifying. What if it was someone he went to college with? Oh my god, he would never, ever live it down. He contemplated hanging up but before he could hang-up and leave the country she quickly continued, ‘Don’t hang up. It’s me, Erica.’

Oh shit, OK so only a little bit less mortifying. It was just Erica, little blonde epileptic Erica from school. Erica, Erica Reyes, who had a crush on him all through high school.

Well, this wasn’t awkward at all.

‘Um. Hi Erica.’

‘Stiles! How are you?’ She asked cheerily as if she wasn’t an escort agency receptionist and he wasn’t a 21 year old virgin calling up for sex.

‘Pretty embarrassed at the moment. How are you?’

Erica laughed, ‘I’m good. Just paying my way through college at the moment. God I haven’t seen you since high school - ’ she tailed off as if seeming remember what she was doing and why she was in the phone with him, she cleared her throat, ‘Ah sorry, probably not the best time to catch up, um so I was going to send Isaac out. But um I think I might give you someone you didn’t go to school with.’ And then she gasped a little. Stiles had a feeling she wasn’t supposed to tell people shit like that.

‘Fuck! Isaac Lahey?’

‘Uh well’ she floundered, ‘I probably shouldn’t say anything, we have confidentiality shit signed and stuff.’

Stiles knew it was Isaac Lahey though. There had been no other high schoolers named Isaac at Beacon Hills High School.

Thinking back to then he remembered Isaac had been nice, a lacrosse bench warmer, like him. Actually Stiles wouldn’t mind being de-virginalised by him. Not at all.

Except, you know, it’d be kind of awkward. Coz Stiles would be paying him for sex and that’s never not awkward.

‘Um, anyway’ Erica continued, ‘It looks like you’re in luck because we’ve got another guy, he’s our most popular escort but he’s just had a cancellation. He’s experienced, completely gorgeous, as are all our guys at Alphamale Escorts, and he’s called Derek.’

He sounded… he sounded intimidating if Stiles was quite honest. He sounded like the epitome of an ‘Alpha’ male if you mind the pun.

Erica must have sensed his hesitation so she continued, ‘Seriously though Stiles, he’s good. We’ve never had a complaint with him, not one. Do you know how rare that is?’

‘Do you?’ Stiles countered, he had a feeling Erica hadn’t been doing that job for very long.

‘Shut up. I’m new. But seriously though, he has literal abs of steel, like ones you just want to lick.’

‘Got a little crush Erica?’ Stiles teased. God dammit! He was stalling. Again.

‘Oh my god Stiles, you have no idea! When you work where I work its kinda hard not to have a crush on your co-workers. And Derek? Well Derek’s special. He’s something else.’ Erica sounded almost wistful.

‘Fine! Saddle me up, book him danno. Lock him in.’ Stiles huffed, it didn’t matter that much, as long as they could come over tonight he wasn’t fussed who it was. He just wanted the damn thing gone.

‘Awesome! So yeah just before we do addresses and stuff I just have a few personal Derek questions to ask.’

‘Derek questions?’ Stiles asked dubiously.

‘Yes, Stiles, Derek questions! Every escort has a set of questions that need to be asked of the clients so they know what to prepare for.’

‘Um OK, shoot.’ This was turning much more complicated then he thought it would. But he supposed it made sense, he would want to be as prepared as possible if he were an escort.

Stiles as an escort. That was a sobering thought.

‘Ok so first question. Any specific kinks?’


‘Yeah kinks, so do you like role play, hand cuffs, feet, panties, BDSM?’

‘Um OK so let’s just put down no specific kinks. Jesus Erica I’m a freaking virgin. How am I supposed to have kinks if I’ve never experienced any?’

‘Hey, I know how much porn people watch and most of its not the vanilla stuff. Trust me, you have your kinks.’

Stiles huffed in exasperation; he had seen lots of porn, no doubt about it. But kinks? Was there anything that got him off more than anything else? Um yeah, practically anything to do with sex. Literally anything. He was horny all the time that he literally couldn’t be picky about kinks. Hell anything half sexy made him half hard, so there was that.

‘Ok well just leave it straight. I don’t think I could handle anything else on top of that.’

‘Vanilla it is. Um also I need to verify who you are. But I already know who you are so that’s easier.’

Stiles almost rolled his eyes at the phone; this was literally the strangest conversation he had ever had in his entire life and that includes the one when he got high with Scott when they were seniors and they debated the philosophical relevance of a purple teletubbie and whether it ever got Tinky Winky down that people made fun of his sexuality. Yeah, that had been a strange night. Also notable for the fact that that was when Stiles came out to Scott, still high, using Tinky Winky as his moniker. As far as coming outs went Stiles had thought it all in all quite successful, he’d gotten a hug and a sleepy, ‘Dude, that’s awesome, Tinky Winky rocks.’ And then they’d fallen asleep.

Stiles jumped when he realised Erica was still talking to him.

‘Also, lastly, any specific requests for Derek himself? Clothing preferences? Anything else?’

‘Uh no? He can wear whatever he wants. I don’t really care.’

‘Well OK! That was easy, wasn’t it? I must warn you however, because he’s the best, Derek’s rates pretty high.’

‘It’s OK.’ Stiles said quickly, ‘I’ve got lots of money.’

It wasn’t a lie, he did have lots of money. More than he knew what to do with anyway. It was such dumb luck that the measly fifty dollars he had invested in his first year economics class had hit gold and now, through careful observation of the markets, Stiles had been able to pay off his dad’s mortgage, move out into his new swanky apartment and pay his college bills. Money was pretty cool but being a virgin was not, so he combined the two and here he was, being asked highly invasive questions by a former high school acquaintance that had once had a crush on him.

Money sucked sometimes.

‘Well then you shouldn’t have any trouble. Is eight OK for you?’

‘Eight’s great.’ Stiles said hurriedly.

‘OK, I hope you find Alphamale Escorts satisfactory. Can’t wait to hear from you again.’

And with that Erica had rung off.

Stiles glanced at the clock. It was 7. He had an hour. To do what?

Idea! He could have another shower!

So Stiles had another shower (his fifth for the afternoon) then got dressed.

It was 7.30. 30 minutes to go. What should he wear?

His normal plaid?

His suit?

No, not his suit.

A dressing gown?


Why wasn’t there a handbook on all this, surely someone would have written something on the subject of how to deal with escorts.

Then Stiles had an idea.

The internet! Of course! The internet had all the answers.

After about half an hour of clicking link after link and practically inhaling knowledge, Stiles knew everything on how to be a good ‘client’.

It was enlightening, to say the least. Well not really, basically it was just saying that you treat an escort like a human being. Stiles could do that! He did that with everyone every day. That part was easy.

But the internet failed him on the whole what to wear thing. All it kept saying was ‘wear something you feel comfortable in’.

What the fuck.

That’s nothing advice, that’s like telling people to ‘just be themselves.’

Stiles felt comfortable in everything. He had been stressing so much he hadn’t realised that he only had five minutes to decide. Derek was going to be here in five minutes.



He looked down at what he was wearing. Jeans and a plaid shirt. Not particularly sexy, but wasn’t Derek supposed to be the sexy one? Or did Stiles have to provide some of the sexiness too? Things were going to suck pretty badly if that was the case, Stiles and sexy didn’t really fit in the same sentence or universe, or solar system together.
Fuck, all Stiles was saying was that Derek had better bring the sexy.



What if he was someone Stiles knew? Stiles didn’t know any Derek’s. But who’s to say that was his real name. Just because Isaac used his real name didn’t mean Derek did. What is he went to high school with Derek. Nah Erica would have said something. Wouldn’t she? Maybe this was all some elaborate prank to get back at Stiles for not noticing her in high school, but come on it wasn’t Stiles’ fault he was gay.



Stiles didn’t know what to do with himself. Where did he put the money? Did he give it to Derek straight up? What is Derek takes one look at Stiles skinny ass and walks out. What if Derek (all so mighty Derek) had standards and didn’t sleep with anyone who wasn’t attractive. Shit, Stiles was so done for if that was the case.


There was a knock at the door.

Fuck, of course Derek was early.

Stiles walked slowly to the door. He wanted to lose his virginity so much, and now he was dragging his feet. What was wrong with him? The butterflies in his tummy were what’s wrong with him. He hadn’t had a case of nerves this bad since he asked out Lydia Martin in eighth grade and she’d sent him crying to the toilets. For some reason, right now, he had a vague sense of déjà vu.

Fuck, he prayed that he didn’t end up in the toilet crying at some point tonight.

Stiles hovered at the door. He didn’t have a peephole. That sucked.

He almost had a heart attack when the door was knocked on again. Fuck. This is it. Just fucking do it Stiles, he told his mind as he braced himself as he opened the door.

Stiles hadn’t realised he’d closed his eyes until he had to physically open them to see who was standing on the other side.

He caught his breath. Stiles was literally breathless.

The man opposite Stiles wasn’t even a man, Stiles was certain of it. Nope this guy wasn’t a man; he was a model out of an Abercrombie and Fitch catalogue or the cover of a magazine. There was no way this was Derek the escort.

He was Stiles height, just a touch over. He had dark hair and he was dressed in a suit. Without a tie so Stiles could see a glimpse of his hairless chest.

That was a simple explanation of the man standing opposite Stiles.

If Stiles was to go into detail, Derek’s (was it really Derek? Stiles thought he might be dreaming so he couldn’t be sure) face was beautiful, handsome, rugged and flawless all at once. The sculpted stubble on his gorgeous cheeks highlighted his grey green eyes (or were they light hazel?) and his straight nose. But it was his eyebrows; his eyebrows were a thing a beauty.

Eyebrows which were currently pulled into a frown.

Derek was frowning at Stiles.

That snapped Stiles out of his reverie.

Shit, how could he have fucked this up already? Was he staring too much? The guy must be used to it by now, he was practically a Disney prince come to life (admittedly a scowley, darker type prince, but a Disney one all the same).


‘What?’ Stiles asked, he was so caught up in his daydream about Disney princes and Derek’s eyebrows that he almost missed what Derek said.

‘ID.’ Derek gritted out as if Stiles were mentally incompetent.

Stiles was a little affronted, ‘Dude, I’m 21!’

‘Give your ID and I might believe you.’ Derek said again through gritted teeth and then he added, ‘And don’t call me dude.’

‘But Erica checked! You don’t need to see it.’

‘Jesus! You look about 16! And I don’t care what Erica said I’m not walking into this apartment if I don’t see an ID in the next 30 seconds.’

Stiles stood gaping for a second then sprang into action, sprinting around his lounge room trying to find his wallet.

He eventually, after what seemed like an hour, when it was probably like 20 seconds, found it under his couch. How the hell did it get there?

Stiles shook his head, it didn’t matter. He gleefully he ran back to the door and thrust it under Derek’s nose. Derek took it from him and checked it, which apparently meant looking back at Stiles and back to the picture on his drivers license. Checking the back of it and looking at Stiles again and then back to the ID. Stiles huffed in impatience.

Stiles held his breath until finally Derek seemed to grunt in amazement when he must have yes, concluded Stiles was 21 and no, not 16 as he looked.

Stiles couldn’t help that he had a baby face.

‘Finally! Can you come in now or did you want to see my birth certificate?’

Derek scowled again at him and Stiles sighed.

Only he, only Stiles fucking Stilinski could somehow have managed to find the grumpiest hooker, in all of Beacon Hills, to rid him of his virginity.

Chapter Text

He almost jumped when Derek walked through the threshold confidently and intimidatingly. Like he’d done it thousand times in a thousand strangers homes.

Wait, scratch that, he probably had.

‘Um so there’s a coat rack over there if you want to hang your jacket?’

Derek nodded his thanks and slipped his off his jacket. Stiles swallowed as he watched Derek biceps move. The guy had nice biceps, nice hands, nice everything.

Stop it Stiles, he told himself instantly, be a good client. Remember, human being, not a piece of meat.

After he hung his jacket, Derek turned to look at Stiles expectantly. Shit, what did Stiles do now? What was the etiquette? What would his mum do? Ewww, no, his mum would’ve never hired an escort. Wait, but guests! She used to have guests over all the time.


‘Uh, did you want something to drink?’

Derek looked a little surprised which was a great improvement on the permanent scowl. If the scowl was what his normal expression then people were weird for liking his so much, ‘Sure, what did you have?’

Stiles was a little stumped for moment. What did he have? Soda. He didn’t really drink beer, so no beer. There was a bottle of jack somewhere left over from his last bro night with Scott. Water?

‘Well I have soda, and water. Or whiskey. Somewhere.’ He said vaguely, gesturing to the kitchen.

‘Waters fine.’ Derek said, settling himself on the sofa. Making himself at home.

‘Really? Its kinda bland.’

‘I’d prefer not anything too heavy.’ Derek said with a raised eyebrow and a faint smile. AHA! So Derek could smile!

‘Why?’ Stiles asked instantly then he cringed, because they were going to have sex, of course. Him and Derek, sex, together. Scrawny assed Stiles and built-like-a-god-Derek.

Stiles was suddenly very nervous again.

His hands shook as he passed Derek his water apologising profusely when he got some on Derek’s pant leg, he still wasn’t entirely sure that Derek wasn’t here to kill him. Derek, however, merely raised an eyebrow (again), ‘Nervous?’

Stiles exhaled in relief, ‘Fuck, yes.’

‘It’s OK. It’s fine to be nervous. Especially for your first time. Can I ask why?’

‘Why I’m still a virgin?’ Stiles said a little bitterly, collapsing on the sofa next to Derek, making sure he wasn’t touching him. Why was he doing that? They were going to have sex, it shouldn’t matter.

Derek nodded.

‘Uh well first I was waiting for the right person and then I waited too long and now it feels like I’m like never going to get some, hence the escort company.’ Stiles leg started jiggling. That was bad; his leg hadn’t jiggled like that since high school when his ADHD had had to be controlled with drugs.

Derek’s hand came down on his knee and Stiles sucked in a breath, but it immediately stilled the jiggling which was cool.

‘Wow, looks like you’ve got the magic touch.’ Stiles joked.

Derek didn’t remove his hand, except he placed his water on the coffee table.

‘You can ask me questions, if you like. If that’s what will make you feel better about this.’ He asked slinging his hand casually over the back of the couch, resting slightly on Stiles’ shoulder.

Derek still hadn’t removed his hand form Stiles’ knee, the heat was setting Stiles skin on fire.

Stiles gulped, ‘Questions?’ he squeaked out.

‘Yeah, about what I do. Sometimes it helps with the nerves.’

‘So have you ever done a virgin.’ Stiles blurted out, trying desperately to ignore Derek’s fingers as they started to lightly caress his knee cap.

Knee caps weren’t sexy, they just weren’t. So why did it feel like there was some kind of direct line from his knee cap to his dick. Which had apparently got over its nerves now by the way it was twitching.

Derek looked floored for a second, ‘I have, yeah. But it was in the past. My clients these days are usually more, more experienced. Adventurous.’

‘Oh.’ Stiles squeaked out, feeling instantly inadequate, he knew he should have put panties on the kink question, pink panties, or anything really.

Anything to make him stand out to Derek.

Wait, where the hell had that come from?

‘It’s ok though, these days it’s kind of rare to get someone like you. Especially for me. And trust me, I know exactly what I’m doing.’

Stiles had no doubt in that as Derek’s hands starting moving up his thigh. His other hand curling behind his neck tracing a pattern of fire between Stiles shoulders blade.

Holy mother of fuck. Stiles was being seduced. That’s what was happening. He was being seduced by the guy he was paying to have sex with him. Derek really was a professional he mused.

‘I have no doubt about that.’ Stiles breathed out, he hadn’t mean to say it out loud but was glad that he had when Derek flashed him a predatory smile full of white teeth.

Holy shit, Derek should come with some kind of warning, hot when scowling; devastatingly awe inspiring when smiling.

‘I uh, I’ve never really done anything, like at all with a guy before.’

Derek raised an eyebrow at him, ‘Kissed?’

‘Oh yeah, god yeah. Definitely kissed.’ He hastened to assure Derek although Derek didn’t really look as relieved as Stiles thought he might. In fact Derek was looking at Stiles lips as though he was personally offended by their presence.

‘But nothing else.’ Derek breathed, getting closer to Stiles as Stiles unconsciously swayed toward him.

‘Uh no.’ Stiles said breathlessly as Derek eyes darkened possessively? Nah Stiles eyes must be playing tricks on him, except that his eyes never left Stiles’ lips.

Now Stiles wished he had waited for Derek to be his first kiss. He barely remembers the drunken make outs that constituted all of his ‘experience’ but he will be sure to remember Derek leaning over him as he automatically leant back giving Derek purchase and leverage over his body. Derek cupped his cheeks, breath costing over his lips as he lowered his full lips to meet Stiles’. It was chaste at first, just Derek’s dry lips on Stiles’, but Stiles body didn’t seem to care it was chaste. He was already hard in his trousers and his breath was coming out in pants. He was now fully reclined in a horizontal position as Derek hovered over him, looking completely mouth-watering, like Stiles’ very own, personal wet dream.

And Stiles couldn’t help it when he let out a moan. Then, suddenly Derek stopped and pulled back. Shit, What did he do now?

However Derek looked a little sheepish, aplogetic, ‘Sorry, that got a bit out of hand. I’m meant to usually ask you what you would like, what you wouldn’t like. How far I can go.’ Derek said, looking down at him smiling slightly.

Stiles interrupted, ‘Seriously dude, do whatever. If I don’t like something I’ll tell you.’

Derek’s eyes darkened as he growled out, ‘Don’t call me dude.’

Stiles was saved from replying by the crash of Derek’s lips against his. This time when Derek kissed him he kissed him with intent as he feathered his tongue along the seam of Stiles’ lips, almost asking for permission. Stiles eagerly let him, opening his mouth wider to allow Derek to flick his tongue, tasting the inside of Stiles mouth.

To be quite honest Stiles was overwhelmed, he couldn’t believe he could be so turned on from just kissing and he marvelled at the intense heat and sensations that were being created from just the simple touch of Derek on his skin, his mind almost shorted out when Derek placed a thigh between Stiles legs creating the friction he had be desperately craving as he rutted against the hard muscle.

Derek moved his hands from Stiles’ face and started feeling down his body. Stiles gasped when they brushed his nipples. Derek grinned into the kiss and repeated the movement, undoing Stiles’ buttons as they explored his chest. Stiles hesitantly placed his hands on Derek’s waist and Derek smiled in encouragement. Tentatively Stiles began to explore under Derek’s shirt.

Erica was right, Derek had amazing abs, but it wasn’t just abs, it was little pockets of muscle Stiles never even knew existed. He was so caught up in the sensation of Derek’s body on his and Derek’s hands on his chest that he didn’t even realise Derek had divested him of his shirt and was now laving at his nipple and playing with his happy trail, his hands ghosting along the tops of Stiles’ jeans.

Fuck, that felt good Stiles thought as he arched his back against it. But So did Derek’s firm thigh against Stiles’ dick and Derek’s abs, fuck everything felt awesome, he felt like his body was on fire and he was going to come soon, if he didn’t stop grinding his pelvis on Derek’s thigh. So he did stop.

Derek immediately stiffened and looked up at Stiles, and whoa, Derek’s pupils were blown, his face was flushed and his hair was a mess.

He looked fucking debauched, and Stiles had done that.

Derek had never looked so good.

‘Something wrong?’ Derek asked, looking a bit dazed.

‘Ah no, I just don’t want things to end too quickly. Um if you know what I mean.’ Stiles said, looking down at the hardness straining against the zipper of his jeans.

Derek smirked, ‘Bit of a nipple guy huh?’

Stiles blushed, ‘Apparently. Is that uh, is that a bad thing?’

Derek smiled, ‘Nah, I like it. I like that you’re so sensitive, I forgot what virg..’

Derek tailed off, looking a bit guilty, ‘Its ok du-Derek, won’t be for much longer anyway.’ Stiles said flashing what he though was a charming grin. He probably just looked constipated.

‘Let’s say we take this to the bedroom then?’ Derek said as he climbed off Stiles, Stiles was pleased to note Derek looked just as hard as he was.

Probably Viagra. He put it out of his mind when Derek offered a hand up.

‘Fuck Yes! Bedrooms, uh bedroom is a good idea.’

Stiles only felt slightly self-conscious as he led the way to his bedroom and let out a whelp of surprise when Derek tackled him onto the bed the moment they walked in the door, grinning into Stiles chest a he pulled a finger up along the ridge of Stiles hardness in his jeans, ‘Let’s take these pesky things off? Shall we?’

Huh, Derek was a bit playful in bed. Or was that just to put Stiles at ease. Derek probably knew all the tricks.

All Stiles could do to the question though was nod silently as the gorgeous man in front of him knelt next to the bed and slowly pulled down his zipper. His cock sprung from the denim, pulling on the batman boxers he was wearing underneath. Shit, he’d forgotten about those, they weren’t exactly sexy.

Oh well Derek had enough sexy for the both of them,

Plus Derek didn’t seem to care and he gently grabbed Stile cock through his boxers with one hand and divested Stiles of his jeans with the other.

The man was talented.

Stiles was suddenly very aware of how naked he was and how not naked Derek was.

As Derek started palming Stiles through his boxers and nipping at his earlobe, Stiles murmured, again, ‘Wait.’

Derek halted immediately, ‘Are you OK?’

‘Yeah,’ Stiles aid back, ignoring the warmth that had pooled in his stomach at Derek’s genuinely concerned face, ‘I just want to see you take off your clothes.’

‘Yeah?’ Derek asked with a cocky grin.

Stiles laughed back but said with a blush, ‘Yeah.’

Derek smiled reassuringly as he rose from the bed, stood in the center of Stiles’ room and started unbuttoning his shirt.

There was no dancing, or swinging of his hips but the way he held Stiles eye throughout the strip was unbearable sexy and Stiles blushed, again, at the intimacy of it.

The shirt was thrown to the floor and Stiles marveled at Derek’s smooth toned body. And yes, he really did want to lick Derek’s abs. Maybe if he asked nicely?

Derek toed off his shoes and socks and started slowly unbuttoning and un zipping his trousers. Letting them fall to the floor. He stepped out of them wearing only his black boxer briefs. And then one tug later and they were on the floor too.


Derek was impressive. Like really impressive. But not too impressive, not so impressive that Stiles didn’t want to get all up in that. Not intimidatingly impressive.

But let’s just say that if Stiles hadn’t been fully convinced he was gay before, he certainly was now. It was like Derek’s dick wasn’t a normal dick, it was a work of art, long, thick, veined and already hard as rock.

Damn Viagra.

‘Wow’ Stiles breathed, he literally didn’t think people that perfect were actually real. No wonder Derek was so freaking popular, he was obviously a Greek god. A Greek god who was standing there, completely naked, smiling at him, Stiles fervently ignored the stupid fluttering in his heart. Now was not a time for sentimentality. Now was a time for sex, sweaty awesome monkey sex.

Yeah, sex with Derek was going to be pretty awesome. His dick thought so too, Stiles actually didn’t know if he had ever been so hard in his entire life.

Derek stalked toward the bed and Stiles eyes glazed over. Derek was like an animal, a virile Stiles-virginity-stealing animal and Stiles couldn’t help but lick his lips. Derek’s eyes caught the movement, eyes zeroing in on Stiles mouth as he climbed onto the bed, on top of Stiles covering every inch of him with his toned body and Stiles almost came embarrassingly fast. Derek’s body felt like silk, like hot, hard, silk and his cock even better as Derek started to slowly grinding their hips together. Flashes of pleasure shot up Stiles’ spine and he let out an involuntary moan, arching his neck as Derek nipped bites up and down only to draw back looking momentarily embarrassed.

‘Nah, that’s ok. Neck nips feel goo-o..’ Stiles strangled out as Derek swooped back down to the area between his neck and shoulder, sucking, biting lightly and kissing.

‘Fuck! That mouth.’ Derek breathed, capturing Stiles’ mouth again in a teeth gnashing kiss before pulling back abruptly. Stiles protested.

Derek’s hair was mussed, his eyes were dark and all Stiles could think about was getting that mouth back on his, or on any part of his body as soon as possible.


‘What. What. What’s wrong now!’ Stiles said weakly, attempting to regain the precious friction back on his cock, thrusting up feebly. It was no fun when it was just him.

‘So you want to lose your virginity?’ Derek said roughly, almost subconsciously moving his hand down to cup Stiles straining, already leaking cock.

Stiles felt his eyes roll back. Man that felt like a billion times better when someone else did it.

Wait? Was there a question there somewhere?

‘Stiles?’ Derek said again watching avidly as Stiles broke apart in front of him.

‘Virginity. Yes! I want it gone! Take it!’ Stiles said frantically. Fuck if Derek didn’t stop soon he was going to fucking come before anything had really begun.

‘Stiles,’ Derek almost growled out, his fingers now caressing Stiles perineum lightly, dusting over his hole, ‘Tell me what you want.’

‘Fuck me.’ Stiles breathed, wait. That was it. That’s what Derek needed to hear! Was that some kind of consent thingy, because he was pretty sure that was cleared up when he actually rung an escort agency ASKING FOR SEX.

‘I want you to fuck me! Now!’

‘See? That’s all you had to say.’ Derek chuckled darkly, kissing his way down Stiles body, making him arch up at the contact with his nipples and the way he circled and sucked on his belly button.

Belly buttons were super sensitive. Who knew? Derek probably, because you know, he was a prostitute.


Difference anybody?

All thoughts soon flew out of his mind as beautiful, attractive Derek’s head came in direct level with Stiles groin. Oh fuck. Was Stiles about to get his first blowjob? Yeah he was, and by the hottest guy in the whole entire world.

Best night ever.

At the first touch of Derek’s mouth to his cock Stiles bucked up, he couldn’t help it. Derek however took it all in his stride like the professional he was, bringing a large, strong hand to Stiles hips, flicking his tongue across his slit, as if he were tasting Stiles’ pre-come and by the groan he let out apparently he liked it? But then again, he was an escort. Which meant he was probably faking it. At that moment though, Stiles didn’t care, it couldn’t have been the fact that Derek had started sucking him down even further down his throat and Stiles vision went white hot.

Was it possible to die from pleasure? Because Derek was currently deep throating him. Yes. Deep throating. Him. Stiles Stilinksi.

It was fucking awesome.

Derek soon started bobbing his head up and down, his talented, not in use hand had started massaging Stiles balls, his perineum and circling Stiles’ hole.

It was slippery and warm. Heated lube? Who the fuck cares? Stiles thought as he immediately relaxed his body, welcoming the intrusion when Derek slowly massaged a finger into his anus. He knew what it felt like, well kind of. He had often gotten himself off with a few fingers clenched in his holes, trying to hit his sweet spot whilst vigorously rubbing himself.

Derek’s extremely talented mouth and talented hands were making it very hard for Stiles to keep in control and when Derek slipped in another finger, scissoring them slightly, faintly brushing them over Stiles prostate, he was a moaning, quivering mess. Seriously though, the sounds he was making didn’t actually sound human. He sounded like a cross between Chewbacca and a cat. That was attractive.

After three fingers Derek was consistently hitting Stiles prostrate and filling him up and his orgasm took him by surprise. One moment he was a quivering mess, chanting Derek’s name like a sacrificial prayer, fucking himself down on Derek’s fingers and bucking into Derek’s throat and the next his back was so bowed in white hot, delicious, incredible pleasure he thought he was actually going to break in half or pass out, or die, or possibly all at the same time. His vision was blanking, his hands curled in Derek’s hair like it was the only thing tethering him to the bed. His come felt like it had been wrenched out of him by Derek’s clever tongue as it splashed down Derek’s throat.

Derek swallowing him down greedily was possibly the hottest thing he had ever seen in his life.

He must have blacked out, because when he came too Derek was cradling his head, kissing his lips tenderly.

‘What are you doing? Now would be an excellent time to fuck me.’ Stiles said hoarsely, rolling weakly onto his front.

‘It doesn’t have to be from behind.’ Derek said softly as he was kissing Stiles’ shoulder then stopping, looking at Stiles shoulder as if it had personally offended him or confused him. Both expressions were quite similar.

‘Oh. Well I read that for like first times it’s easier.’

‘It is.’ Was all Derek said and wait. Was that disappointment that flitted across Derek’s face? Stiles may be in a sex coma but he was pretty sure Derek looked disappointed, that what? That Stiles wouldn’t be facing him during sex?

All thoughts soon fled from his mind when Derek carefully put on a condom and started lubing himself up.

Yeah Derek had a really good looking dick. A good looking everything.

Derek reached out to Stiles’ butt, again and Stiles quickly batted his hand away, ‘Dude, I’m like loose as. Just fuck me already.’

Derek scowled and muttered something that sounded suspiciously like ‘bossy’ and Stiles hid a grin. That grin was soon wiped off his face when Derek slowly entered him.

God Derek felt big inside of him and Stiles grunted when he slid in halfway.

‘That good?’ Derek asked breathlessly, like he was having enormous trouble holding back. Maybe he was? Maybe sweet vanilla sex with Stiles was turning him on?

‘Fucking brilliant but if you don’t stop treating me like a piece of glass and get balls deep I will literally start fucking myself on you.’ Stiles gritted, loving the feeling of being filled by Derek’s cock.

Stiles didn’t know if it was the threat or Derek getting turned on by the threat because suddenly Derek slid in the whole way and Stiles let out a manly squeak, ‘FUCK!’

‘Shit. Are you ok?’

‘Yes, fuck. God I feel so fucking full. I swear man, I was like made for gay sex. You know?’

He could almost feel Derek rolling his eyes at his back as he started to move, long steady strokes inside Stiles ass, which soon got faster and harder as Stiles started to moan beneath him and his dick started to twitch.

‘Fuck that feels awesome’ Stile let out breathlessly and Derek huffed above him quickening his hip snaps, punctuated with grunts of,


Thrust (Stiles moaned involuntarily as Derek started hitting his prostate again)








Thrust (Stiles started to brace himself, if Derek wasn’t careful Stiles was going to come. Hands free, which was fucking awesome)





‘DOING’(Derek’s frantic humping made Stiles clench up, which made Derek thrust even harder which then made Stiles clench again; it was like a vicious, awesome, mind bogglingly circle of pleasure)





On the last thrust he brought a hand around and pulled on Stiles’ red, swollen cock and with a yell Stiles shot his load all over his bed sheets, intense pleasure spiking through his entire body and ridding his legs of any energy. He would have collapsed from sex exhaustion if Derek hadn’t grabbed his hips at last second, wrenching him back up against him until a second later when Derek came.

They tumbled to the mattress together; Stiles riding out the last of his orgasm with Derek’s impossibly good looking face nestled between his shoulder blade and his neck.


That was fucking awesome. Sex was awesome. Sex with Derek was awesome. Cuddling with Derek was awesome (but did that cost extra?).

Stiles didn’t really know how long they stayed there together but suddenly Derek’s now softened dick was pulled out gently and Derek got up from Stiles’ back slowly, as if he didn’t want to wake him. Stiles was quite content to sleep for a billion years as he drowsily watched Derek pull his clothes back on, ignoring his cock as it gave a hopeful twinge at the sight of Derek’s magnificent ass wiggling into his briefs.

Damn that boy was fine.

It wasn’t until Derek knelt down to give him a quick kiss on the cheek and left his bedroom that Stiles mind cleared. He glanced at the bedside table. His money was still there. Fuck.

Stiles quickly scrambled out of bed, pulling on his boxers and grabbing the envelope. He was not getting in trouble for not paying, not be Erica, and definitely not by Derek.

He was calling Derek’s name as he jumbled down the stairs and consequently almost braining himself on the bottom step when he tripped.

Thankfully big, strong arms were there to catch him. And Stiles let out a pant of relief.

‘Are you alright?’ Derek asked as he looked down at Stiles and suddenly Stiles was caught in Derek’s gaze. He really did have pretty eyes. Like seriously pretty. Like Jenson Ackles standard pretty. Like I-want-to-gaze-into-those-eyes for the rest of my life pretty.

Stiles shook his head, clearing it of those stupid thoughts as he righted himself.

‘Don’t mind me. Clumsy is a side trait of the Stilinski’s, unfortunately.’

Derek smiled minutely at him. Geez he had a pretty smile too, like a I want to gaze…Stiles averted his eyes, what the hell was wrong with him? Seriously he just had sex with the guy; it wasn’t like they were going out.

‘I uh- I just wanted to give you this. Ah your money. You forgot it. And you most definitely earned it.’ Stiles said, laughing a little but stopping when he catches the indescribable expression on Derek’s face.

It was as if annoyance had a baby with hesitance and they named it offended and were now dancing over Derek’s features.

Stiles was a little stuck at the etiquette. Was this how things were meant to go? He was supposed to pay Derek right? They wouldn’t send Erica around in the morning with a little ALPHmale escorts courier hat asking for the cash. Would they?

Why would Derek look like that? At him?

Stiles didn’t find out as Derek finally took the envelope, almost whispering a quick thanks and heading for the door.

Stiles was struck but then he suddenly yelled out, ‘Aren’t you meant to, like, count it or something dude? To make sure I haven’t shorted you?’

Derek’s retreating back stalled for a moment and he turned back to look at Stiles with a constipated look on his face. Stiles was sure he was about to say something and Stiles wanted him to say something, anything, but disappointment flooded through him when Derek turned back around, steadied his shoulders and rushed out the door.

Stiles collapsed on the couch, ignoring his slightly twinging behind and brought his hands to cradle his face, the way Derek had when they were fucking.

What the hell was wrong with him? Why was he feeling so bereft, like something had been wrenched from his body, something that wasn’t an orgasm.

He was just lonely, that was it. He was just emotionally latching onto anyone who gave him intimacy because he had no one for himself.

Maybe it was time to get a boyfriend and forget about Derek.

Yeah, like that’s going to be easy.

Derek was a god.

And Stiles may be a little in love with him.


Chapter Text

‘You did WHAT?’

‘Scott, shut your mouth!’ Stiles hushed as he checked to see if anyone had heard him. No one had. It was 3 am in the morning and they were at an all-night diner. The only other person in the place was the chesty blonde at the counter who was glued to Gossip Girl reruns on the TV.

Scott lowered his voice, like half a decibel, ‘But Stiles you had sex! With a prostitute!’

Stiles groaned, ‘Yes Scott, I’m quite aware, I just told you that.’

Scott looked dumbfounded for a moment, ‘Did It like hurt? In the butt?’

Stiles rolled his eyes, his whole world was tilting and all Scott could care about was the fact he had a dick up his ass less than two hours ago. This was not what he was after when he called an emergency bro-code summit an hour after Derek had left, ‘Yeah, kinda, but like a good hurt, you know?’

‘Cool’ Scott said contemplatively, as if trying to figure out how that could be, ‘Like when you hurt after Lacrosse right? It aches but the aches a good ache.’

‘Kind of?’

It wasn’t. Sex with Derek was nothing like lacrosse training but Stiles didn’t really want to explain the finer points of aggressive anal sex to Scott. Not right now. Not at 3am in the morning, stone cold sober, in an all-night diner whilst he was having a love breakdown.

‘Sweet. So how does it - ’

‘Oh my god, Scott, that is so not important right now. I am literally having an existential Romeo and Julio, unrequited love disaster with an escort I met like 6 hours ago, I’ll tell you all about the mechanics of gay sex later OK?’

Scott smiled sheepishly, ‘Yeah, sorry dude. So, tell me the extent of this crisis.’ He said professionally. Humph, that was more like it.

After all that, though, Stiles was reluctant to continue, ‘Um right so. Remember high school?’


‘Remember Lydia.’ Scott winced. Stiles also winced. Come on, it was Lydia Martin.

‘How could I forget! Dude you like proposed to her on every Valentine’s Day since third grade which was cute when you were little but just became really creepy in high school.’

‘Yeah thanks for that. So, Lydia, right.’

‘Stiles what about Lydia, you loved her, like a lot. What has this got to do with that escort – oh fuck’ Scott said, comprehension dawning on his features.

‘Yeah’ Stiles said miserably, slumping down in his chair, practically mauling the straw of his coke.

‘Um are you sure it’s not like infatuation? Like this guy, I assume was good. In Bed?’ Scott asked, a little desperately. Stiles didn’t blame him; the Lydia Martin saga contained a lot of bad, embarrassing memories. For the both of them.

‘Yeah’ Stiles said dreamily, lost in daydreams of perfect penis’ (Peni?) and cheekbones that could cut a plate. And an ass that curved like a… well you get the idea.

Stiles knew he was pining, moping even, which was weird because Stilinski’s do not, as a rule, pine (Lydia Martin episode aside). They are action oriented creatures of love. Declarations of love, easy. Rejection, however, is taken to heart, but a Stilinski is never a piner. So why the hell was he pining?

‘Stiles! Focus! So are you sure you’re not just feeling like some kind of stupid gratitude love for this guy because you just had amazing sex and he took your virginity.’

‘Hmmm, maybe.’

‘Because like most people don’t fall in love after one night of sex.’

‘Geez Scott, when ever had I ever been “most people”’ Stiles asked sarcastically, because it was true. He was not a regular person. Nor rational, especially when it came to love. Cue mortifying Lydia Martin slideshow, ‘Seriously though, I waited because I thought I was trying to find the one. And I didn’t, in all 3 years of coming out I’ve never even been close to having a boyfriend, let alone have sex. Doesn’t that tell you anything?’

‘That you’re a compulsive commitment-phobe who latches onto the idea of love with people out of your league because you know you’ll never have to worry about actually ever being with them.’

Stiles was pretty sure his mouth was agape. Since when did Scott become so smart? And kinda cutting?

Scott just laughed at his expression, ‘Dude, I’m training to be a psychologist, do you think I just do this shit for fun?’

Stiles was contemplative, ‘Well, Derek was exceedingly gorgeous.’

Scott choked on his straw, ‘Derek?’ he asked, eyes wide and watering.

‘Yeah, his name was Derek.’

‘Derek Hale?’ Scott’s eyes were practically bugged out of his head.

‘I have no fucking idea Scott. His names not even probably Derek, people use pseudonyms when they escort? Except for Isaac, of course, the virginity stealer.’

‘Isaac the virginity stealer? Isaac Lahey?’ Scott’s face was turning an interesting shade of red.

Stiles inwardly cursed, he wasn’t supposed to tell anyone that.

‘Why, do you know him?’

‘Maybe, was this Derek tall dark and handsome, impossibly ripped?’ Scott asked furtively.

Argh, Stiles hates furtive Scott. Scott couldn’t lie for shit so his default was furtive. His eyebrows furrowed and his eyes went all squinty.

But that did sound like Derek.

‘What is maybe Scott? Maybe you do know Isaac the virginity stealer? Maybe you know the possible love of my life, my Julio!?’

‘Who?’ Scott asked then looked away desperately trying to catch to waitresses eye, utilizing his delaying furtive tactics.


Scott finally looked back at Stiles, biting his lip.

Stiles started to get a bit worried.

‘Are they like drug dealers? Are they like a prostitute gay drug dealing duo? Do they sex people into submission like a sex superhero crime fighting duo? Scott, just tell me they’re not undercover escort extraordinaires like a male version of Charlie’s angels. Minus Cameron Diaz, nothing against her but Drew Barrymore kicks ass and probably steals virginities and Derek kinda reminded me of Lucy Liu even though he’s not Asian’

Scott looked a bit dazed, ‘Ah, no. Dude, How much caffeine have you had?

Stiles was twitching, ‘A bit.’

He had actually consumed the entire six pack of energy drinks he had in his cupboard after Derek had left. It was the only destructive thing he could think of to do because he couldn’t for the life of him find the whisky to get wasted.

‘Look, dude, I might know them. But you have to promise me you’re not going to go all bunny boiler on me OK?’

Stiles inwardly freaked out, but managed to contain his excitement and rolled his eyes innocently, ‘Funny, the guys got movie references. Come on Scott, buddy, you know me.’

Scott rolled his eyes, ‘Yeah I do and that’s why I’m like kind of reluctant to tell you.’

‘Scotty boy. Listen to me carefully. This is possibly the most awesomest thing that has ever happened to me, in like ever. But I will promise to be cool. Plus it’s the bro code to tell me, the bro code trumps all other codes, you know that.’

Low blow, Stiles knew, but Scott took the bro code very seriously.

‘OK well, they may both, possibly live in my apartment block.’

Huh, Stiles thought, disappointingly normal, no Charlie’s Angels, but information nonetheless.

‘What? How come I’ve never seen them?’

Scott shifted uncomfortably, ‘Well, like you usually only come round at night and they are probably, now that I know, out on paid dates and shit. Isn’t that what escorts do?’

‘Some have sex, too.’ Stiles points out with his now completely decimated straw, ‘And steal virginities, apparently.’

Scott rolled his eyes, ‘Stop saying, “stole”, no one can steal a virginity. It doesn’t work like that. I suppose you can lose your virginity, but come on, you’re just giving fuel to society that socially constructs an added value to something in order to primarily oppress females into not being in control of their sexuality.’

‘What?’ It was way too early for Scott’s liberalist shit, even though Stiles usually secretly agreed with it.

‘Look, dude, being a virgin, having your virginity is fine.’

‘Even at 21?’ Stiles asked doubtfully.

‘Jesus, of course it is. It should be completely your individual choice. But that’s the kicker, your choice. Still, in society being a virgin is still associated with the pure, the white, untainted. Do you think now that just because you’ve had sex that you are somehow tainted?’

‘Uh, no.’

‘Exactly. But you can’t win, can you. Especially women, who get it way worse than men, but it happens to a point with men as well. You felt bad about being a 21 year old virgin, right?


‘But then again would you feel bad if you had already slept with like 50 guys before you were 21, right?’


‘But why? As long as you enjoyed it, consented and practiced safe sex why is it anybody else’s business who you had sex with!’ Scott said, a little frustratedly.

‘Sexual sociology huh? Stiles asked wryly watching as Scott angrily stabbed at his drink.

Scott huffed, ‘Yeah, it tends to get me a bit riled up.’

‘I’m calling your bluff though. I know you’re only trying to get me off topic. Tell me more about the escort duo.’

Scott rolled his eyes, ‘Not really much to tell really. Just that they live in the apartment opposite me. Sometimes I see them at the gym.’

Stiles suddenly had a horrible thought, ‘They’re not like together, together, are they?’

Scott frowned, ‘Unless they’re really good at hiding it then I would say they’re just roommates. Isaac seems nice. And he’s pretty.’

Stiles waved that information away, ‘Who cares what the expert de-flowerer’s like, what’s Derek like?’

Stiles was now leaning so close to Scott across the table that the curvy blonde by the counter was watching intently, maybe she thought seeing them kiss would be better entertainment then watching Blair and Chuck having sex in the back of a limo? Pfft, some people had no taste. Chuck was waaay hotter than Stiles.

Scott shrugged, ‘He’s, like, built? I guess?’

‘Jesus Christ, I had sex with the man Scott I know what he eats. Protein shakes probably.’

‘Oh well, he’s gruff? But quiet, but like not shy, just introverted I guess? Isaac said there was stuff with his family so I guess he has trouble trusting people. But he’s a bit of a butt compared to Isaac. Yeah, Derek’s a butt.’ Scott confirmed.

Stiles rolled his eyes, but was inwardly extremely offended for his current imaginary life partner. He couldn’t blame him though, Scott started to love psycho-analysing people ever since he started his psych unit at college, Stiles hated it because Scott was convinced Stiles had a personality disorder, namely OCD.

Stiles didn’t.

His mum had him tested.

But the stuff about Derek’s family was interesting.

A thought occurred to Stiles as he looked suspiciously at Scott, ‘Since when do you known Isaac so well.’

The furtiveness was back with a little blushing for good measure, ‘Oh, well I just kinda recognised him form high school, the day he and Derek moved in and we just got chatting. Sometimes we play COD or gym together. Sometimes we get dinner together.’

‘WHAT?’ Stiles yelled and Scott winced. It may be an overreaction, but come on, Redbull did that to him. Plus Scott was his bff, he was allowed to be jealous, possessive, whatever.

‘Stiles don’t be mad! We’re still besties, bro’s for life, bromantic brothers. It’s just that you’ve been so caught up lately with like college and shit and since Allison and I broke up it’s been kinda lonely.’

Stiles heart started to beat a little more regularly and he sighed, he had been kind of a shit friend lately, he didn’t blame Scott for branching out.

Even if it was with an apparent cherry popping sex professional.

‘Wait, you don’t like, like him? Do you?’

Scott looked back at Stiles a little wild eyed, ‘What?’

‘Because if you’re gay too, that’s totally fine, I won’t resent you for stealing my thunder. Well I might, but only a little bit.’

Scott spluttered a little bit and Stiles had to wipe off the raining bits of Fanta off his face. Jesus, only Scott McCall would still drink Fanta after high school. It wasn’t even raspberry.

‘But Allison. I was with her for like forever.’

‘Could be bi.’


‘Bisexual, you like both. Or pansexual which is liking basically everyone regardless of gender, sexual or identity.’

‘Oh. But I’m not even sure if I like Isaac?’

‘Dude, do you guys do dinner?’

‘Sometimes, but I do dinner with you.’

‘Yeah but we’re bromantic brothers as you so eloquently put, we can get away with shit like that. But if you’re doing that with someone you only re-met, like what? 3 months ago? Then it wouldn’t be a stretch to call them dates.’

‘But what if Isaac’s not gay?’

Stiles snorted, ‘Dude, he works at a gay escort service.’

‘Yeah but there are heaps of guys that do gay porn who aren’t gay.’

‘That’s a point, but how many of them actually request to be the cherry popper? You gotta love your work if you like the virgins. And how do you know about the gay porn industry so much? Wait scratch that, I probably told you all about it that night we were high.’

‘Jesus, don’t remind me.’ Scott said, rubbing a hand through his hair suddenly he sat up straight, ‘Dude, what if he’s only trying to seduce me? What if he only wants my virginity. What if he really is some kind of master buttsex virgin seducer?’

Stiles inwardly groaned, how did this conversation turn from the discussion of Derek’s sexy butt to Scott’s gay/virgin/Isaac-cherry-popper-with-a-master-seduction plan crisis?

‘Well then, you’re just going to have to ask him.’ Stiles said flippantly.

‘What? Really?’

‘Yeah, you gotta be honest. Either he really likes you and wants to date you, you know with you actually knowing, or he thinks you know and if you don’t like him like that you’ve been inadvertently leading him on or he is a master butt sex virgin predator and you’re his next victim.’ Stiles said with relish, still high off the energy drinks.

Scott looked exceedingly worried. Stiles didn’t actually think much about the last two. Isaac seemed nice and Scott was a good judge of character (name calling Derek aside), but Stiles, desperate as he was, wasn’t above manipulating his best friend in order to gain access to Derek.

Stalker anyone?

‘Oh god. I should , shouldn’t i? I should, like, straighten things out with him, mind the pun.’

‘Oh that pun was very much minded. We should go now then.’ Stiles said earnestly.

‘Now?’ Scott squeaked out.

‘Yes. If you don’t go now you’ll never get the courage to ask and the times probably perfect because he’s probably finished work for the night.’

‘You’re right Stiles. I should probably go.’ Scott said, steeling himself to leave.

‘Wait!’ Stiles said hurriedly, ‘I should go with you, for moral support!’

Scott clapped a hand to Stiles’ shoulder, ‘You’re such a good friend Stiles!’ Scott said cheerily.

Stiles only felt a little bit bad for manipulating Scott, but hey, true love, what can you do?

Exactly, you do what you have to, including pushing your best friend into the arms of virgin snatcher escort named Isaac.

Oh well.

Scott could deal.

They drove in Scott’s car because Scott wouldn’t let Stiles drive, not with all that sugar and caffeine running through his veins. Stiles agreed, albeit silently.

It just went four when Scott pulled up to his swanky apartment block that he bought with his dads life insurance payout(‘He wasn’t there when I was growing up so why shouldn’t he pay for something for once’) and they slowly took the stairs.

Scott looked terrified.

‘Dude, what if I’m not gay or bisexual or whatever?’

‘Jesus Scott, have you worked it out or what?’ Stiles said exasperated.

‘It’s not like I had the entirety of high school to angst it out like you did. This is super recent for me. Like literally half an hour ago recent, forgive me for feeling a bit unsure.’ Scott hissed back.

Stiles just snorted and pushed him forward, ‘Jesus Scott worst case scenario he hates you forever, best case scenario you end up bumping uglies with the most skilled butt virgin defiler in Beacon Hills, it’s basically a win-win situation.’

Well that didn’t help, Scott looked only more panicked. Yeah, Stiles was not the best with assurances.

‘By the way, if Derek answers remind me to act surprised.’ Stiles continued.

Scott looked at Stiles suspiciously, ‘You’re not doing this all just to make Derek love you, are you?”

Stiles pretended to look wounded, hand over his heart, ‘Scott, buddy, would I do that to you? I am completely, 100% here for you and your sexual identity crisis. But you know if Derek decides to sex me up or declare his undying love to me, right there in the doorway, I wouldn’t turn him down.’

Scott snorted, ‘He’ll most likely think you’re a stalker and then he and Isaac would have to move away and I would never see him again.’

Scott looked distressed at that statement and Stiles pushed his luck, ‘How did you feel saying that just now?’

‘It hurt, a bit. Like more than bro hurt.’

‘Like heart hurt?’


‘Ah Scotty boy, welcome to the mutual gender love club. Rainbow flags and Celine Dion CD’s are free upon entry.’

Scott laughed, like Stiles wanted him to. Nothing made Scott feel better than an ironic joke based on socially constructed stereotypical ‘gay’ assumptions, it made his intellectual brain go all warm and fuzzy, or so Stiles liked to think.

They were now on the floor standing in front of Isaac’s door, which was slightly ajar, the muffled sounds of I Love Lucy could be heard behind it.

Scott looked at Stiles and Stiles shrugged back.

‘He never leaves his door open, like ever.’ Scott whispered.

‘Maybe something’s wrong? Should we call the police?’ Stiles whispered back.

‘We should probably see if everyone’s OK?’

Stiles nodded vigorously. How horrible would it be if Derek was hurt in some way? Stiles’ angsting would know no bounds.

Scott slid the door open slowly, calling out softly for Isaac. It wasn’t til they got to the shut door of the living room that they could hear muffled voices, one loud, angry and the other quiet and soothing.

They both unconsciously put their ears against the door to hear better.

‘He made me take the fucking money Isaac! It wasn’t, it wasn’t even sex you know? It was, jesus, it was making love, even I know the fucking difference or I thought I did.’

Stiles held his breath; that slightly broken, bitter voice sounded a hell of a lot like Derek. Derek talking about Stiles, apparently. Although Stiles couldn’t be certain, maybe lots of men made Derek take their money? But why wouldn’t Derek take it in the first place. That had been kinda puzzling to Stiles, now that he thought about it.


Stiles suddenly flailed at Scott when he came to his conclusion, Scott hushed him violently as Isaac replied more quietly.

‘Fuck, Derek, all you have to do is find him again. I’m sure he would agree to go on a date with you.’

‘You weren’t there Isaac. He just seemed happy to get rid of his virginity. And fuck, let’s face it, who would want to date a prostitute anyway?’ Derek growled.

Isaac sighed, ‘Escort’ he corrected Derek but went on, ‘But I know Derek, Jesus fuck I know. I used to not care you know? It was just what I did, people would have to deal. But lately that’s changed. Like this guy that I really like, am kind in love with? What would he say if he knew that I slept with the sexually inexperienced for a living? Fuck Derek, I steal people’s virginity for money.’ Isaac said, sounding almost defeated.

Oh shit, Stiles thought whirling round to stop Scott but before Stiles could do anything, Scott had already barged through the door angrily.

‘There’s no such thing as stealing virginity's, Isaac!’ Scott said breathlessly, finger pointed in the air imperiously, ‘And I don’t fucking care that you do anyway.’

Derek’s face was frozen in a scowl, he was sitting on the couch, head halfway out of his hands as if he had been cradling it. Isaac was frozen sitting next to him, hands dangling between his legs.

They were both now currently staring at Scott, and subsequently at Stiles, behind Scott.

‘Surprise’ Stiles managed to say squeakily, before all hell broke loose.


Chapter Text

Ok so not all hell broke loose, just a few palings maybe; a lava river or two bursting its banks.

Derek had taken a flat look at Stiles and had promptly walked out of the room.


Isaac had simply stared at Scott a little dumbfounded.

Stiles was actually pretty impressed actually, by Isaac.

He didn’t know what he had expected but the slim and tall guy with brown curly hair and a bone structure to die for was not it. In fact he looked exactly how he had in high school. Was it then that he knew that he had a penchant for ploughing the unploughed, for being the first time anal bandit?

It figures Stiles thought, it’s always the normal looking ones with the strange fetishes.

Isaac colored and Scott turned to Stiles with a thunderous look in his eye. Fuck, Stiles clapped a hand to his mouth, he might have just said the last bit out loud.

Aw shit

‘I don’t actually choose to be ‘that’ guy, you know? It’s just that I’m the newest so I don’t really get to pick and choose, so I get left with the virgins, freaks and weirdo’s.’ Isaac said, a little pathetically.

Scott nodded with him

Oh my god, Shut up Scott Stiles thought, you literally have no idea what he’s talking about.

Idiot. Stiles fumed inwardly his eyes narrowing.

Although he wasn’t really angry at Scott for being a love struck fool, Stiles may or may not be pissed that Derek had kind of walked out on them all.

On him.

Or about the fact he looked unfairly good looking in a pair of sweats and a wife beater.

That too.

‘Wow thanks Isaac, what a way to bunch us all together, actually technically I’m not a virgin anymore, thanks to the sex-metron currently sulking in, which I assume, is his bedroom?.’ Stiles said sarcastically, gesturing to himself and then the hallway Derek had disappeared down.

Isaac’s bambi eyes widened, ‘Are you Stiles?’

‘Dude! We went to high school together! Plus Scott talks about me all the time, right Scott?’

Scott started shifting a little guiltily, ‘Um not really.’

‘What? I’m your freaking best friend, how could you not talk about me?’

‘Stiles I’m not going to tell the guy I’m crushing on about my gay best friend, that’s like defeating the point of having the crush in the first place.’ Scott said exasperatedly, throwing his hands in the air.

‘Let me remind you that you didn’t even know you were crushing on him until I told you, like an hour ago.’ Stiles replied, equally exasperated, arm flail way more impressive.

‘Maybe it was instinctual?’ Scott said eyes widening, ‘No, get this, maybe my body knew before my mind or I subconsciously did it because my conscious mind wasn’t recognising it? Huh, someone should do a study on that.’

Stiles nodded thoughtfully, someone totally should. He then jumped when Isaac’s voice cut in. He’d forgotten he was present, so had Scott, apparently due to the blush creeping up his cheeks.

‘You have a crush on me?’ Isaac said pointing a finger at Scott.

Scott sighed gustily, ‘Yeah.’

‘So you’re gay?’

‘Dude, I think I’m both?’ Scott said looking at Stiles for confirmation. Stiles nodded distractedly, craning his neck to try to see down the hall where Derek had gone.

‘Um yeah, I just didn’t think you liked me, like that.’ Isaac said quietly, ducking his head.

‘Well if it makes you feel any better, neither did I. But you’re kind of awesome and I think wanting your dick strictly makes my feelings for you non-platonic.’

Isaac was now looking at Scott as if he hung the moon, ‘You want my dick?’

Scott nodded enthusiastically.

Isaac breathed out an awed ‘Awesome’.

Stiles rolled his eyes, idiots, ‘OK! So, we good? Scott wants Isaac's D, Isaac wants Scott’s D and a very impatient Stiles wants Derek’s D. Which is where? By the way?’

‘Down the hallway, first door on the left.’ Isaac said quickly eyes not leaving Scott’s.

‘Thank you Isaac, who has now been crowned unwilling virginity taker, unless it’s Scott’s’

Stiles ducked down the hallway to the sounds of Scott’s spluttering. Ha! That’ll teach him for falling in love with an escort.

Stiles groaned, you have too, you idiot he told himself. Except his hooker was way less emotionally available and was now currently locked in his bedroom apparently blasting some god awful music. Wait, was that…

‘One Direction, yeah, he plays it when he’s stressed.’ Isaac said from behind him, looking a little flushed.

One Direction? What the hell? Stiles meant no hate, literally, he could probably sing at least two of their songs. But Derek? Derek seemed like the kind of guy who liked smooth jazz or old school hard rock. And yes Stiles thought that knowing someone for under three hours of which consisted of mostly fucking constitutes him a professional about their music tastes.

But One Direction?


‘Scott told me what happened, and if you’re the guy Derek saw tonight then I think he’s pretty messed up about it all.’

‘Messed up? How? He just did his job.’ Stiles heard a faint bang against the wall from inside the bedroom. What was Derek doing in there?

‘Uh OK, doing his job, maybe, but shit likes this happened before, he wouldn’t tell me about it, but like, trust? Ah trust doesn’t come to him easily. But he did kiss you places other than you mouth or your dick. So there’s that.’

‘Uh yeah? Like my neck and shoulders and my back. He was pretty affectionate actually.’

‘See that’s the thing, he has like rules or whatever, most guys or gals don’t really care but it’s like Julia Roberts in Pretty Woman, except his no go zone is kissing your body.’

‘Huh, well that makes sense.’

‘So, you like him?’

Stiles looked around shiftily and whispered back, ‘I think I love him.’

Isaac went wide eyed, ‘Oh, well, you should probably ask him to let you in, he’ll open the door to you. Maybe.’

‘Wow, thanks for the vote of confidence there, Card V Taker.’

‘No problems. I’m going to go now and take Scott’s V card, nice and slow. Have fun with the wooing!’ Isaac said playfully and Stiles tried not to wince. He hoped that was the first and last time he would have to hear about Scott’s sex life. Basically his brothers sex life. He had more than enough of that in high school with Allison because vaginas? Not really his thing.

‘Here goes nothing’ Stiles whispered as he knocked on the door. He literally got one knock out before the door was wrenched open.

Holy shit, Derek was shirtless and was now only wearing basketball shorts. He was drenched in sweat, his hair plastered to his forehead, veins throbbing in his arms. Stiles tried very, very hard to keep his mouth shut. It wasn’t working. But seriously, it was like he had forgotten what he looked like naked and now here he was, breathtakingly awesomely built and sweaty and nice to look at.

‘What do you want Stiles.’ Derek asked in a tight voice, face giving nothing away.

‘You kissed me!’ Stiles blurted out. Wow, good work big mouth, Derek’s really going to fall in love with you now.


‘Not just on the mouth and my dick, but like everywhere.’ Stiles said, a little breathlessly.

‘No I didn’t.’ Derek denied quickly, a little too quickly.

‘Err, yeah you did.’ Stiles said, bringing the collar of his shirt away to reveal hickies scattered down his neck and the tops of his shoulders, ‘You can’t deny that was you and Isaac explained your little Pretty Woman thing. So why me huh?’

Derek scrubbed a hand through his hair, not answering, ‘Why are you here Stiles?’

‘Ah, well, see I’m here for Scott!’

‘For Scott.’ Derek said flatly.

‘Yeah, Scott next door. Scotty the love bug.’

‘Isaac likes Scott.’ Derek said with a frown.

Stiles rolled his eyes, ‘I know dude, that’s why we’re here. Scott’s decided he likes Isaac too.’

‘Oh well that’s good.’

‘Yeah it is.’

There was an awkward silence. Stiles was kind of getting that Derek wasn’t the chatty type. Or maybe he just didn’t know how to deal with clients who stalk him down at 5 in the morning, which, hey, was pretty reasonable too.

So Stiles took a big breath and did what he came here to do, ‘Look, I know its stupid Ok? But last night was kind of special for me, and i know that your first time is meant to be. I just felt something? With you? Something more than just a fuck?’

Ok so it wasn’t much of a declaration, he was a bit rusty on the whole true love thing. Because, you know, it only happens once.

Stiles had been fiddling with the cuff on his shirt and not making eye contact because when it came down to it this was different then declaring his love for Lydia Martin in third grade. This was different then chasing Danny around for his first year of college. This felt real? Scary? Like his heart was going to leap out of his chest and smother Derek in kisses yelling ‘Love me! Please!’

His plea was met with silence.


At least it wasn’t a flat refusal. Or maybe it was worse, maybe Derek didn’t even think he was worth it. Maybe it had all really been a joke; make the virgin fall in love with you and then break his heart.

Stiles would bet it was all Erica’s fault.

Fucking wonderful, now Erica was going to have to die.


‘You made me take the money.’ Stiles was so caught up in inner dialogue that he almost didn’t hear the quiet admission from Derek.

His eyes shot up, it was Derek now who was the one not making eye contact. Huh, he looked like a kid who had just been caught stealing cookies. An adorable kid. Actually not a kid at all, a hot, sexy adorable man with arm veins that Stiles just wanted to… focus Stiles!

He snapped his eyes back to Derek’s face.

‘What the hell was I supposed to do? I just assumed you were meant to be like that. Plus, sex coma dude. You know what that’s like, I could barely think, let alone make rational decisions.’ Stiles said beseechingly then continued, narrowing his eyes, ‘And Derek you can’t say something like that without me asking why you care about it so much.’

Derek eyes were blank and suddenly, with a little flail of the arms, Stiles understood. Derek jerked in surprise and Stile took the opportunity to dart under Derek’s outstretched arm into his room.

And wow, what a room it was. Whatever Stiles had been expecting from escort, One Direction playing Derek, it wasn’t this.

What he had been expecting was black silk sheets, monochromatic walls, a framed black suit or two.

Derek seemed the type.

It wasn’t like that at all.

His walls were white, his carpet was white. His bed was a single? What the hell? And his bedspread was beige. In one corner was a selection of weights and a mirror. A wardrobe took up the space the right of the room. It was saved from being too bland by the single framed poster of Star Wars: Episode V hanging over the bed.

‘Don’t entertain much in your own bedroom?’ Stiles said plopping down on Derek’s bouncy bed.

Derek looked physically pained and Stiles smiled, at least it was an improvement on the blankness, ‘Yeah I bring clients here all the time.’ He said blandly.

Guys got a sense of humor, albeit dry. Stiles could work with that. That and the Star Wars poster; perhaps all was not lost.

‘I know your deal.’ Stiles said quietly, looking across at Derek from under his eyelashes.

Derek stood warily inside the door crossing his arms and watching as Stiles comfortable tucked his legs underneath him, ‘My deal?’ he asked.

‘Yeah dude, your deal. The reason you know how to fuck like a jackhammer but are physically incapable of emotions.’

Stiles caught the quickly covered up flinch at the curse word. Interesting.

‘Fuck like a jackhammer?’ Derek asked with an eyebrow raised, small smile on his lips.

‘Yeah dude, my butt still aches.’ Stiles said but then continuing hurriedly on when Derek looked concerned? Utterly devastated? Stiles couldn’t tell they all looked pretty similar on Derek’s face, ‘But a good ache. Like awesomely good.’

Derek looked like he was trying hard not to preen. He was so preening the preening bastard.

‘OK so sexual prowess aside I know your deal. Who was he?’ Stiles asked baldly.

‘What?’ Derek said a little confused.

‘Who fucked you up?’

Derek’s eyebrows lifted and then his face closed off.

‘Derek, dude, don’t do that to me, I need to know.’


‘Because I just do, OK? Call it the Stilinski curiosity. Plus this’ he said gesturing between him and Derek, ‘this is something, whether you try to deny it or not.’

Derek’s judgy eyebrows and eyes followed Stiles’ flailing arm movement and Stiles dropped them, a little self-consciously.

He was a flailer, a consummate flailing professional, flailer extraordinaire, there nothing he could do about it and his future husband was going to have to deal.

So Derek could suck it.

Literally, if he wanted to.

Not helping Stiles, he told himself, cursing the images of the blow job Derek had given him from the night before that kept dancing in his vision and making him hard.

Plus Stiles was determined. Stubbornly so, because being rejected by Lydia Martin for 10 years kind of did that to a person. Or maybe it was just Stiles who doggedly pursued someone romantically whether or not they liked him or not.

He wasn’t crazy.

His mum had him tested.

Derek seemed to huff in resignation, ‘Fine, but it wasn’t a he, it was a she.’

Hey, whoa, Stiles was not expecting that.

‘I worked as a straight escort before I moved to Alphamales.’ Derek explained.

‘Oh my god, did you have to look at vaginas Derek? Because ew.’

‘I had to do a lot more than look, Stiles.’ Derek said rolling his eyes.

Stiles made a pretend gagging noise in his throat, then remembering where he was he straightened up and regally motioned to Derek with a hand, ‘Continue’.

‘Ah yeah so I had this client. She was one of my firsts. I was only young. And I knew it was stupid, I knew I did it for money but I may have fallen in love with her. Or what I thought was love.’

‘Um so I began seeing her without payment. We still had sex, but there was no money involved even though it was on company time, she said that if I thought that that was real than she shouldn’t have to pay me and I agreed. Because I thought I loved her. The last time I saw her I told her that I loved her, so she fucked me and then shoved $400 in my face, told me she never wanted to see me again and walked out.’

‘Shit.’ Stiles breathed.

‘Yeah, so I left and joined Alphamales and have been there ever since.’

‘Fuck.’ was all Stiles could say.

‘Yeah, fuck.’ Derek said dejectedly, moving to sit beside Stiles on the bed.

‘Well I like you.’ More like LOVE YOU, but Derek probably wasn’t ready to hear that just yet, or the several poems and sonnets Stiles had been composing in his head since they had met. No matter how cute.

‘You barely know me Stiles.’ Derek said, sadly.

‘You of all people should know that doesn’t matter. I know enough, I know you like Star Wars, I know you like to keep fit, I know you like having sex and are very good at it, I know you have a sense of humor, I know you’re kind because even though you have the money to rent a place yourself you let Isaac rent one with you, I know you’re an emotional cripple with issues with trust. And I know you think what we did was more than fuck because you’ve flinched every time I’ve even mentioned the word fuck or that I said what we did being anything other than “making love”.’

‘Um, OK?’ Derek said looking at Stiles in awe.

Yes! Awe was good, awe was fucking fantastic and if Derek moved his head a little closer to Stiles he could kiss that awe right off his face.

‘I know you like me too because every time I say your name the little ridge between your eyebrows smooths out, only for a second, but it fucking smooths out Derek.’ Stiles whispered as Derek’s face got closer to his.

‘What do you study again?’ Derek murmured, his lips a centimeter from Stiles’ lips.

‘Human behavior motherfucker.’ Stiles said laughing as Derek captured his lips in his own.

‘I’m an escort Stiles.’ Derek said warningly, pulling back from the deliciously slow wet kiss.

‘Well if your happy as an escort, than I’m happy.’

‘I don’t think I would be happy with a job that makes me technically cheating on you very night.’

‘Then change your job’ Stiles said, hands encircling the back of Derek’s head.

‘You said so yourself, I’m emotionally unavailable.’

‘I’m overly emotionally available for the both of us. Plus that’s what couples do, they work on stuff like that.’

‘Couples?’ Derek asked teasingly.

Stiles faltered a little, ‘Only if you say you like me back.’

Derek dove in and captured Stiles in a heat blistering kiss, tongues clashing for purchase, lips inhaling one another.

Pulling back Derek smiled, ‘Well then mister smarty pants, what does that little piece of human behavior tell you?’

Stiles was dazed for a moment then gathering his bearings he smiled again, wetting his lips noticing Derek’s eyes following the movement, ‘That you fucking love me too.’


Did he just say love and me and too in the one sentence, to Derek?

Shit. Idiot Stiles and his idiot brain to mouth filter, Stiles thought frantically, he just got him and now Derek was probably going to run for the hills.

Stiles held his breath as Derek leant back to look at him contemplatively, finally after an age he answered, ‘Damn you’re good Stilinski.’




Was that a declaration?

That had better had been a fucking declaration. If it wasn’t Stiles was going to go home and watch Pretty Woman for the next 3000 years and cry into the sock Derek had accidentally left behind.

God he was a weirdo.

Apparently Derek liked (nay loved) weirdo’s? Which was in itself all kinds of awesome. Plus Star Wars was always cool.

Stiles loved that Derek loved Star Wars.

Minor freak out over; Stiles slid into Derek laps and brought hands to cradle Derek’s scruffy face, sliding his lips back across Derek’s, ‘Tell me how good I am again Derek.’ Stiles whispered taking control of the kiss.

‘Like really, really, really good.’ Derek panted as he came up for air, eyes blown dark, lips red, bruised and completely debauched.

Damn straight Stiles was good (pun completely intended).

Best Night Ever.