1 - 20 of 34 Works in Assistant Stiles Stilinski
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It's the end of a long day, and Derek Hale gets a professional call that is boring him to tears. Who better to make him feel better while having to deal with this call than his personal assistant, Stiles Stilinski?
And Stiles is only too eager to offer his...assistance.
Series
- Part 5 of 30 Day OTP NSFW!Challenge
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Teen Wolf weight gain prompts by CharlRhodes, CptKate (SterekChub), SterekChub
Fandoms: Teen Wolf (TV)
16 Jun 2025
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Teen Wolf Weight gain prompts
You'll find the summary in the first chapter.
I hope you'll enjoy them!
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“Are you this mean to all of your assistants?”
“Not always.” Derek replied. “Just to the ones who think I’m a douchebag.”
“So you are this mean to all of your assistants.”
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Derek Hale, CTO of Bionic Labs, doesn’t need a personal assistant. Laura disagrees. Enter one Stiles Stilinski: personal assistant extraordinaire, who just won’t. shut. up.
(Peter is off to the side, watching with a bucket of popcorn.)
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Stiles is Peter’s personal assistant. Stiles is also Peter’s personal office slut.
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- Part 13 of Short Porn
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When Worlds Collide by Arieanna, Sterek_wins (sad_Stony_boi_hours), ZeffieDavis02
Fandoms: Teen Wolf (TV)
28 Jun 2023
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Stiles Stilinski and Co moved to NYC fresh from out of high school. They wanted to try the Big Apple and be their free selves. Being an Omega was always a shit thing for Stiles. He tries to grin and bear the burdens that come with it. It all changes when he finds a wounded Alpha on the streets. Saving his life leads to a wild ride of a life.
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"Are you both committing fraud so that Mr.Hale can avoid deportation and keep his chief editor job?" the Immigration services lady asked them.
Stiles froze, his heart was beating fast. How was he supposed to answer that? "I- no. Uhm why would we do that?" He squeaked out, nervously fiddling with his fingers.
"That's ridiculous honestly, where did you hear that?" Derek knew they'd question it but he didn't think they'd already know.
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Stiles is the hardworking assistant of the prestigious Sports reporter Lydia Martin. Stiles hopes to one day be as successful as his boss and write a story that Lydia will approve of… but he’s constantly on his feet and never gets time to himself.
That is until he meets another assistant who works in the same building as he does who also wants to have time for himself(and his model girlfriend). Stiles must implore the help of Derek(who is the assistant of the merciless Finance manager, Peter Hale) and get them to set up their bosses. -
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“A deal?” Stiles asked slowly, keeping his gaze eyeline to Derek’s even though his boss was practically looming over him as Stiles sat in his chair.
“Yes, a deal. I won’t fire you. I will even give you that recommendation you want so badly and turn it into the dean of admissions myself. All you have to do is accept.” Derek’s voice oozed with promise. Like molasses, the sweetness of his promises consumed Stiles.
“What would I have to do?” Stiles gulped. Derek’s mouth spread into a full grin as he leant forward, both arms caging Stiles as they rested on the arms of his chair. Derek’s face was inches from his own. If Stiles just leant a little closer he could….
“Be my boyfriend.”
Wait... What?*Chapter 9 is reposted!
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“I want you to dom me.”
Stiles had dropped his bag and had turned around to gape at Derek. He what now?
Derek had still been staring at his food, angrily, as if he wanted it to disappear.
“You want what?” Stiles asked, just to be sure. His ears must have played a trick on him. Only they hadn’t.
“I want you to dominate me,” Derek had said to his food.
“Excuse me? Are you talking to me?” Stiles had asked again.
He still couldn’t believe it as he stared at the ceiling. Derek had blushed and sputtered for a long time, especially when Stiles walked back into the room and sat down on his spot.
Stiles barely got any answers from his boss, so he had proposed to talk about it on Monday.
He had never in his dirtiest and darkest mind thought Derek Hale would be a submissive. That was just insane.
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Or the one where Stiles and Derek indulge in a BDSM relationship without love. Also, Derek is Stiles's boss.
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“I bring good juice and good news, both piping hot,” Stiles declared upon entering Derek’s office.
Derek stared at him for a moment, lips parted, before his mouth snapped shut and he gestured Stiles to come forward. “Hot. Yes?” -
"I'm just sick of the pining" - Peter Hale by CosenAngel for deliciousirony
Fandoms: Teen Wolf (TV)
24 Dec 2019
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Derek finds a drunk Stiles snuggling Derek's dog in the backyard. And that’s the start.
(Peter had not signed up for the pining.)
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Derek Hale, one of the most popular movie stars, is an asshole. Or so Stiles thinks. He's got this whole sexy playboy routine going with it, but then Stiles will catch a glimpse of the man underneath and it piques his interest - holds his attention. Stiles is determined to figure him out.
Stiles Stilinski, a hard-working personal assistant, is annoying as hell. Or so Derek says. He's stubborn, and loud, and unfairly considerate sometimes that Derek just wants to strangle him (read: kiss him). But he's one of the first people who seems to be willing to learn the man he is underneath a Hollywood persona. Derek hopes he sticks around.
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In for a penny, in for a pound.
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When Stiles’ boss unexpectedly goes into rut, he offers himself to the lycan, knowing all too well how utterly terrifying it can be.
Will his gamble pay off, or ruin everything…?
Series
- Part 1 of Be still, my love.
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Peter rolled over and groaned. He felt like someone had taken a jack-hammer to the inside of his skull, and sandpaper to his throat. He groaned again, but tried to shift his body towards the edge of the bed to swing his feet to the floor.
The room swam when he attempted to stand and he was forced to plop his butt back down onto his 1000 count sheets and wait for the wave to pass. Shit, he couldn’t afford to get sick. He had a meeting with the Jessic Group this morning and Talia would have his ass if he was late.
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Stiles works for Hale Industries, and gets premoted as Derek Hale's personal assistant. So what if Stiles was in love with that man? Derek could have two cents to his name and Stiles would still fall head over heals for him. He can deal with being with his dream guy. He can do it. He will not get swept away in all the madness that is Derek Hale.
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“I don’t have an assistant,” Derek barks out as he looks back to the pile of reports he needs to get done. After the last kid that tried to be his assistant left in tears after the first day, he’s decided he didn’t want an assistant at all anymore.
“Well according to Ms. Hale, you do now. She hired me. I must say your sister is very scary-”
“I don’t need an assistant,” Derek barks out.
Or, the one where Laura hires Stiles to be Derek's assistant.
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A pushy boss (Derek Hale) forces his young assistant (Stiles Stilinski) to marry him in order to keep his Visa status in the U.S. and avoid deportation to Canada.
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"Politics is like foosball: fun, and must always be played with a cup of alcohol in hand. That is, until the ball flies off the table, directly for your eye, because the President of the United States is a competitive asshole who can't lose in the privacy of his own man cave because he has issues the size of Rushmore."
Or the one where Stiles and Derek get it on, stupidly get caught, and now Lydia has to talk to a reporter she hates.