#rich!stiles

Hi anon. @kevaaronday found these for you!

Thank You For This Dance by matildajones

(62,463 | 26/26 | Mature | Sterek) Derek picks up another glass of champagne, and that’s when he sees him. A man stands at the edge of the room, chewing his lip and staring at the dance floor longingly. 

Every person walks past him. Derek must have done it a hundred times this evening. 

--

Derek is not one for dancing, but at a ball he meets Stiles, an orphan, and he becomes quickly attached. He does not care what other people think about Stiles' wealth and status, but it's a lot harder for Stiles to ignore the comments that have haunted him his whole life.

It's even harder to convince Stiles that Derek's feelings are genuine.

Rich Man, Poor Man by TyReed (58,055 | 10/10 | Mature | Sterek) During a first date gone horribly wrong, Stiles Stilinksi realizes that the snarky guy he's been asked out by is actually Derek Hale, an heir to Hale Industries, one of the most profitable companies in the entire world. Who is, for whatever reason, interested in the son of a teacher and a cop, a loser who spends all weekend watching movies in his pajamas, and who is also possibly one of the biggest dorks on the Internet.

At the same time, after screwing up their first date horribly, Derek Hale realizes that the funny guy he's asked out is Stiles Stilinksi, the warmest and kindest individual he's ever met in his life, with a family just a loving and caring. Who is, for whatever reason, interested in a guy who screws up everything he does, lacks any semblance of a backbone, and who is possibly one of the biggest history dorks in all of the United States.

These rich and poor men will come to experience a taste of each other's lives, and learn where the real blessings in the world can be found.

Can You Feel A Whole New Part of Your World? By isthatbloodonhisshirt (53246 | 1/1 | Gen | Sterek) “Can you hear me singing in the shower?” Stiles blurted out, because he had to know, now. If one of his neighbours had slid that note under his door, then it meant Parrish as another neighbour could hear him, too! He had to know if this was all a huge joke and one person had walked by and overheard him and decided to fuck with him.

Or if everyone could hear him and he now had to leave the country. 

Parrish gave him a weird look at the question, but answered anyway, making Stiles’ plans to leave the country speed up in his mind. 

“Of course I can. You’re actually not bad. Though you have been singing a lot of Frozen lately, getting kind of tired of the soundtrack.” 

“Oh my God!” Stiles shouted in his face.

Looking For The Feeling Lost Inside by suchfun (46,069 | 1/1 | Mature | Sterek) "Am I wrong? Do you secretly love modelling? Because if you do then fucking A man, get your coin, but if you're—"

"I can't fucking do anything else!" Derek snarls, and fuck. The shock of it, of finally saying it out loud, startles him out of his beta shift and into silence.

Stiles squints at him. "You mean—" He drags his bottom teeth over his top lip, eyes darting between Derek's. "You mean that literally, don't you. You think you have nothing else to offer."

"I don't have a college degree. I don't have any real life experience or transferable skills," Derek says roughly. "I'm not—a peopleperson. Money and connections only get you so far. Most people don't— it's not worth it."

He knows Stiles hears what he's trying really hard not to say.Stiles

That he's not worth it.

Checks and Balances by AwaitTheMorrow (13,539 | 1/1 | Teen | Sterek) Stiles starts dating Derek after a chance encounter and can't believe how lucky he is.

Derek is smart, funny and genuinely the sweetest person Stiles has ever met. The guy is perfect.

...Maybe a little too perfect.

So When Do I Get To Pledge My Loyalty To The Mob? By RedRidingStiles (10,089 | 1/1 | Mature | Sterek) “Are you my sugar daddy?” Stiles blurts out, slapping a hand over his mouth when his brain catches up to his mouth. The man lets out a soft laugh, making his way around the couch till he’s standing just feet away from Stiles. Stiles can smell his cologne from here, it smells heavenly, Stiles kinda wants to bury his face into the guy's chest so he can figure out exactly what it is. 

“If that’s what you’d like to call it.” The man smiles, Stiles doesn’t think he should be allowed to smile like that. All soft and gorgeous and way too pretty to be legal. He’s still not convinced any of this is real. 

I am writing it, but you’re welcome to write your own version -- the more the merrier!  Mine is here, and Stiles is not actually a poolboy in it, so there’s definitely room for other interpretations.  The Tumblr user @sterek created the gifset, so definitely let them know if you do another version.  I’m sure they’d be thrilled.

Yassssss. Rich Stiles for you. (a few are sugardaddy!stiles trope.) - Anastasia

Under Development by dr_girlfriend

(4/12 I 5,927 I Teen)

Environmental lawyer Derek Hale is determined to stop the planned defacement of his beloved Beacon Hills Preserve by the mammoth Starr Development company. To do so, he makes a deal with the devil himself — Stiles Starr, the brash young scion of the Starr family and COO of Starr Development. Derek hates Stiles at first sight. Mieczysław Stilinski, on the other hand, is someone that Derek could grow to like...or even love.

Lumberjack and the Suit by stagprince666

(3/? I 7,622 I Not Rated)

Always wanting more from his strange little home town of Silver Spring, Colorado, lumberjack Derek Hale is surprised (along with most of the town), when a rich accountant moves to town. Stiles, said rich accountant, moved to the quaint town of 800 so he can raise his niece after his sister's unexpected suicide. Having lost his mother already and his father drunk most of the time, Stiles just needed to get away from everything.

College Boys by AlliraWolf

(6/? I 9,691 I Not Rated)

It's been 6 years since the Hale Fire claimed many lives, leaving Derek on his own to raise his three younger siblings that managed to survive the fire. They don't have much but it's enough to get them by, it has to be enough to get them by. Derek will have to balance raising his siblings, working part time, as well as his college courses. Will he be able to handle it all on his own or will he crack under the pressure? When tragedy strikes will Derek be strong enough to hold it together and keep his remaining family members together in his custody? Or will it all become too much?

You Fixed My Life by LoveActually_rps

(1/1 I 10,992 I Teen)

John Stilinski had had to change tutors for his son five times in a single month so far – ranging from professors and experienced private tutors to intelligent college and university students. None of them had survived more than a week. Greenberg had had given up after just four days.

“Beware of the boy,” Greenberg had warned Derek. “And…stay away from Roscoe,” he had muttered, looking weak and terrified, as if he was recollecting some nasty nightmare.

“Roscoe?”

Greenberg had already fled before he could entertain further confused queries from Derek.

(aka - Stiles is a rich, spoiled brat, struggling academically(or is he?). Derek is his new tutor, who just needs a job.Of course, Stiles owns a grumpy cat – Roscoe - and Derek doesn't get along with it.)

Money can't buy you happiness. by Dykatamee

(1/1 I 13,954 I Mature)

Stiles is a rich boy and Derek is the hot new tennis instructor.

Behind The Music by SwinneyTheGypsy

(8/8 I 17,709 I Explicit)

Stiles is a pop singer who let the industry destroy him. Derek saves him from the industry and himself.

I Know Places by ericaismeg 

(1/1 I 21,721 I General)

Stiles is tired of the fame and the media that comes with being a famous actor. Lydia, his manager, gives him a three week break from his social calendar while his agent, Peter, is off doing who knows what, who knows where. At the last function before his break, Stiles finally meets Derek Hale - the nephew that Peter has been shunned by for the past six and a half years.

Stiles knows how twisted the tabloids get things, it's why he's avoided doing anything remotely scandalous for his entire life. But when Derek Hale wants to get coffee with him, Stiles doesn't care what anyone else says. He's going.

Stiles' Ultimate Gift by LillianDeLooney

(14/14 I 44,529 I Explicit)

Stiles is a spoiled brat who’s sent away to the Hale Family Farm to learn a lesson in respect and hard work. Naturally, he isn't happy about it, but that changes when he meets a very special little girl and her amazing father . . .

“What about you Stiles?” Derek's daughter, Kenny, asks innocently. “Are you gay?”

He chokes on his own spit and quickly downs the remainder of his coke, ignoring the blush stretching from his head all the way to his chest.

“I ah,” he clears his throat awkwardly and rubs a hand over his neck. “I might be?”

She sends him a knowing little smile and nods. “Good.”

~ A story about how to live life, not how to spend it.

Pour Some Sugar On Me by Delta_Immortal

(14/14 I 73,037 I Explicit)

Derek is a highly successful sugar baby and escort in the local area. He’s got clients lined up and he's got money in the bank. He's good at what he does. He plays sweet and hard and fast, giving his time and smiles in exchange for cash and favors. He lives by three rules: No salt, no bad vibes, and no falling in love.

Enter billionaire Stiles Stilinski. Derek's world is about to turn upside down.

Bad Habits by Fudgebug

(12/12 I 108,296 I Explicit)

"Mmmmh pretty.“ Stiles purrs in a way that makes a wild fire torch the planes of his skin.He knows Stiles is drunk and that the boy would probably stroke a pineapple and compliment its attractiveness, but Derek can’t help the way his heart starts to be a huge backstabbing dick, thundering uncontrollably against his chest.It’s painful, because Derek knows it isn’t real.

I found a couple

rich derek / poor stiles:

Birds of a Feather Fuck Together by calrissian18, maichan808 (maichan) (1/1 | 26,144 | NC17)

Laura is a crusader without a cause, Stiles dances like the whole world’s betrayed him and Derek’s having trouble getting both feet outside his door.

Hale Hath No Fury Enterprises by Nival_Vixen (7/? | 21,151 | R)

Derek’s a billionaire with anxiety and a complete inability to be socially adept in any way, shape, or form (just ask Laura). He only agrees to the dating service because Laura’s nagging’s worn him down, but then he sees Stiles’ video response and agrees to go on a date with him.

Stiles just wants to go on a date (it’s been forever and a day since his last one), and he has a thing for this guy’s eyes/smile/everything, so he replies to the somewhat personal questions via video. He’s surprised that he’s asked on a date, but won’t turn it down, even if he’s just spent the last of his money on clothes to impress said date and probably won’t be able to afford dinner.

rich stiles / poor derek:

Animal House by ChildOfTheRevolution (3/3 | 7,653 | G)

Derek is a wallflower

Stiles is not.

Derek might or might not be in love with Stiles. Beautiful, messy, smart, gorgeous Stiles.

It’s not the ideal life, not the life he dreamt about aloud to his parents – he’s no Dodgers pitcher, he’s no lawyer, he’s no doctor – but it pays the bills and it keeps Laura from directing her judging, angry gaze at him too much.

we didn’t have a tag like that so I made one. these are the ones with the most kudos

Pour Some Sugar On Me by Delta_Immortal (14/14 | 73,037 | NC17)

Derek is a highly successful sugar baby and escort in the local area. He’s got clients lined up and he’s got money in the bank. He’s good at what he does. He plays sweet and hard and fast, giving his time and smiles in exchange for cash and favors. He lives by three rules: No salt, no bad vibes, and no falling in love.

Enter billionaire Stiles Stilinski. Derek’s world is about to turn upside down.Derek is a highly successful sugar baby and escort in the local area. He’s got clients lined up and he’s got money in the bank. He’s good at what he does. He plays sweet and hard and fast, giving his time and smiles in exchange for cash and favors. He lives by three rules: No salt, no bad vibes, and no falling in love.Enter billionaire Stiles Stilinski. Derek’s world is about to turn upside down.

Animal House by ChildOfTheRevolution (3/3 | 7,653 | G)

Derek is a wallflower

Stiles is not.

Derek might or might not be in love with Stiles. Beautiful, messy, smart, gorgeous Stiles.

Stiles, well Stiles holds awesome Toga parties with his hot, popular best friends, the big 6, and would never, in a million years notice someone like Derek, until he does.

Oh What These Headlights Have Seen by pterawaters (1/1 | 2,820 | NC17)

Derek’s boss is spoiled, demanding, and far too attractive. Or, the one where Derek is a mechanic and Stiles owns lots of cars.

Bad Habits by Fudgebug (12/12 | 108,298 | NC17)

“Mmmmh pretty.“ Stiles purrs in a way that makes a wild fire torch the planes of his skin.He knows Stiles is drunk and that the boy would probably stroke a pineapple and compliment its attractiveness, but Derek can’t help the way his heart starts to be a huge backstabbing dick, thundering uncontrollably against his chest.It’s painful, because Derek knows it isn’t real.

A story about goody-two-shoes Derek crushing on a Polish Prince Charming with a drinking habit - also the universe keeps on shoving astral poop into his face. It’s utterly spectacular.

Bound by CricketsInTune (10/10 | 49,410 | R)

[Part 2] It's hurts in a really good way that only Helenish delivers?

yes i do know of this and it is wonderful and heartbreaking