Work Text:
Teen Wolf || Stargent || Teen Wolf || His Daughter's Roommate || Teen Wolf || Stargent || Teen Wolf
Title: His Daughter's Roommate – Stiles Summer Stories 2025
TW Disclaimer: All rights reserved to Jeff Davis and MTV. This fanfiction on the other hand is entirely mine. No money is made with this, though reviews are more than welcomed.
Tags: m/m, college AU, Daddy Kink, feminization, crossdressing, explicit sexual content, anal
Main Pairing: Chris/Stiles
Teen Wolf Characters: Mieczysław 'Stiles' Stilinski, Chris Argent, Allison Argent
Writer’s Month 2025 Prompt : loyal + college
Summary: Chris finally has the time to go and visit Allison at college. Allison very cleverly never used pronouns for her roommate, knowing her overprotective dad would worry if he knew she lived with a guy, so Chris assumed Stiles was a girl. Stiles is not a girl. Stiles becomes a problem, but not the way Chris had anticipated, because he finds himself falling for his daughter’s roommate.
His Daughter's Roommate
Stiles Summer Stories 2025
Chris frowned deeply and crossed his arms over his chest when he entered the kitchen. There was a barely clothed boy at the stove, cooking and singing very off-tune along to the radio that was playing at a low volume in the background. The boy had long legs, only hidden by black Batman boxer-shorts, the yellow logo all over them. The span of his bare back was pale and littered with moles, like stars dotting the sky. He was swaying his hips to the music, which did draw Chris’ attention to his narrow waist and very, very nice ass. At which point Chris tore his gaze away from the boy, because his thoughts were going into a very inappropriate direction.
“You must be Scott,” Chris said, voice a bit of a growl.
The boy yelped, nearly dropped the pan and whirled around to stare at Chris with the prettiest, biggest doe-eyes Chris had ever seen. “Aaahh… huh? What? Why would you think that?”
“You,” Chris motioned at him. “Half-naked boy in my daughter’s kitchen. Must be the boyfriend.”
Those pretty doe-eyes blinked at him as the boy nodded slowly. “I can see the logic in that. However: Half-naked boy in his own kitchen . Must be the roommate. I’m Stiles. Hi.”
Chris’ eyes widened and he ran them over the boy’s body again. “You’re not a girl.”
Stiles tilted his head down to stare at himself like he was double-checking. “Astute observation.”
“But…” Chris trailed off, unsure what to do with this information.
He tried to remember really hard. Allison spoke about Stiles all the time. The most loyal person she’d ever met, such a good friend, went shopping with her all the time, had introduced her to both her boyfriend Scott as well as her new best friend Lydia, and Allison, Lydia and Stiles hung out all the time. Stiles’ dad is the sheriff and they used to go to the shooting range all the time so yes, dad, I am once again living with someone who knows how to use a gun and has a permit for it too, I’m totally safe, Stiles is the best. With a heavy sigh did Chris sit down.
“I don’t think Allison’s ever used pronouns to talk about you,” Chris concluded slowly. “So I just… assumed you were a girl. Living with her. The shopping trips, spa weekend, Hallmark movie marathons, I just… Allison just let me believe you were a girl.”
Stiles raised his eyebrows and leaned back against the counter. “First of all, spa weekends are not just for women and if you have never been on a spa weekend you should absolutely rectify that because it is nice to get a little pampered. Don’t even know what to say about the shopping trip thing because… men need clothes too? I mean, I know my current state of dress isn’t exactly driving that point home, but still. And Hallmark movies fuck hard.”
Chris just nodded slowly and regarded the boy who wasn’t Allison’s boyfriend but was half-naked in Allison’s kitchen because he lived in the apartment. He would be more mad at Allison if he wasn’t so impressed by the very subtle deception. The things she chose to tell him about Stiles had most certainly been picked specifically because they had made it easier to assume Stiles was a girl.
“Besides,” Stiles continued casually. “I feel like the whole Scott of it all makes the point of your concerns kinda moot. No, I am not having sex with your daughter after setting her up with my best friend. Though I do get the concern. College guys can be pricks and really dick-driven and your daughter’s a total bombshell. Which she seems to have inherited from her father.”
Chris blinked slowly and looked at the boy who now looked flustered and like he wanted to take that last sentence back. He supposed Stiles had a point, what with Allison now being in a relationship, especially one that Stiles had set her up for, he didn’t really have to worry about the roommate preying on her. Sighing, Chris rubbed his face.
“But also, like, you know that in the greater scheme of things, women can be predators too, right? Like, I could have been an evil lesbian who was trying to get into your daughter’s pants.”
The statement was so ridiculous, it made Chris snort. “I suppose you’re right.”
“I’d be a good evil lesbian,” Stiles nodded, looking genuinely determined. “Well, I guess I’d be better at being an evil lesbian than I am at the whole bi thing. Total failure with all genders. But then I guess it’d be the ‘evil’ part I’d be good at, not so much the lesbian part. Though, judging by my queer girls, they do be liking a girl failure and I would be such a girl failure.”
Chris continued staring at the boy while Stiles seemed to genuinely consider what his life would be like if he were an ‘evil lesbian’. Allison had definitely not lied about the ADHD and the overall ‘uniqueness’ of Stiles, as she had fondly put it. He leaned his elbow onto the table and put his head in his hand as he watched Stiles lament what an epic girl failure he would be. He was cute. Oh no. Allison’s college roommate should not be cute. Then again, he had checked Stiles out when entering the kitchen already and tried to shut those thoughts down thinking this was Allison’s boyfriend. If the cute, rambling, half-naked twink in the kitchen wasn’t Allison’s…
“...Though I would have appreciated a bit of a heads up that you were coming,” Stiles concluded after a bit. “Because I usually do wear clothes, especially when we have guests. I swear.”
Chris pursed his lips and ran his eyes over the boy’s chest. “I don’t mind.”
Stiles’ eyes widened and his cheeks turned dark red, but before he could say anything, there was the sound of a door opening down the hall, directly followed by a slightly panicked gasp.
“Oh no, oh no, oh no,” Allison whispered, her steps picking up as she rushed toward the kitchen. “Stiles! Stiles, my dad is over, you should put on some clo… oh.”
She rounded the corner into the kitchen and paused when she saw Stiles and Chris. She pressed three fingers to her mouth, a guilty expression on her face as she regarded Stiles and a worried expression when she settled to look at her father. She tried her sweetest smile.
“Good morning, papa,” Allison tried innocently. “So you met Stiles…”
“Yes,” Chris nodded slowly. “I met Stiles.”
“He met a lot more of Stiles than he should have. Why didn’t you tell me your dad was coming?” Stiles asked as he walked toward her and, in a slightly lower voice. “Also why didn’t you tell me your dad was a total DILF? So rude of you, Ally.”
Chris was fairly sure he wasn’t supposed to hear that, but his ears still turned slightly red at the words. Allison groaned and covered her face, absolutely uncomfortable with this conversation.
“I didn’t know he was coming over!” Allison defended herself. “He just… stood there, in front of the door, when I woke up this morning, with coffee and doughnuts.”
“I had business around the corner, figured while I was in the city, I might as well surprise my daughter with a visit,” Chris defended himself at Allison’s half-hearted glare. “At least the surprise nature of it didn’t give Allison the chance to put you in a dress and wig to continue the ruse.”
Stiles half turned around to look at Chris with a mischievous smirk. “Oh, if you want to see me in a dress, you just gotta come to the Jungle on Drag night. I look good in a red mini.”
With a wink did Stiles leave the kitchen, presumably to finally get dressed. He also left Chris with the mental image of the boy in a pretty dress, maybe with some lingerie beneath… Chris adjusted himself some and cleared his throat. This boy was a lot. Chris found himself liking that.
“So—o… you met Stiles,” Allison sat down opposite her dad. “I never explicitly said Stiles was a girl. So I never technically lied to you. You just assumed-”
“I assumed what you led me to assume,” Chris leveled a glare at her.
Allison rolled her eyes. “I’m fine! I knew I would be fine! I don’t need you to protect my virtue from evil college boys. I vetted Stiles myself before I moved in, I asked around campus, made sure he didn’t have a reputation. He’s a total sweetheart. Well, kind of an asshole, but mostly toward those he doesn’t like. But I knew you would freak if you heard I’m living with a guy.”
Chris heaved a sigh and nodded. “Now that we moved past the roommate situation, let’s talk about the… boyfriend situation. I’m only leaving in the evening, which means we can have lunch with Scott so I can get to know him.”
“Oh, I would pay money to see that,” Stiles whispered eagerly as he sat down. “You would put the fear of god in that poor bastard. He’ll be tripping all over himself.”
“Stiles,” Allison whined a little. “Please don’t make this any worse than it already is.”
“Oh, it’s gonna be bad that I meet your boyfriend?” Chris asked, eyebrows raised.
“No, no, no, that’s not what I meant!” Allison groaned. “I wish I had taken Lydia and Jackson up on their offer to spend the weekend at the lake house.”
Stiles actually cackled at that and Chris couldn’t help the small smile either.
/break\
Allison Argent was actually the perfect roommate. She was kind, sweet, always punctual on the money, did her chores without complaining or trying to duck out of them, they shared enough interests that they spent time together and didn’t just fully live in their respective bedrooms avoiding each other, she fell head over heels in love with Stiles’ best friend and it was the most adorable and epic puppy love he had ever seen and she introduced the hottest man on Earth into Stiles’ life. The only downside was that said hottest man on Earth was her dad. And that Stiles had made a horrible first impression that would probably lead to Chris never looking at him as anything more than a making-breakfast-at-noon-half-naked kind of irresponsible college boy.
After that first visit, Chris came by seven more times over the semester before he ultimately moved to Beacon Hills. Which was what all the visits had been about, apparently. Stiles knew from Allison that they used to travel a lot for his dad’s work while she was little but that they’d somewhat settled down after her mom died in a horrible hunting accident. It seemed that Chris had wanted to move the base of their business so he could live in the same town as his daughter, which was really sweet and Stiles got that, considering he’d chosen Silver Lake University because the town was only a two hour drive from Beacon Hills and was still Beacon County, so the sheriff occasionally came by for work too and Stiles could easily go back home to visit his dad.
The problem was that Chris was funny and ridiculously handsome and very caring. Not just of Allison. Usually, when he came over, he’d bring dinner, or breakfast depending on what time it was, and he would also always bring something for Stiles. After a few visits, he even seemed to get the hang of what Stiles liked the most. Chris now lived in Beacon Hills, having a deal with the sheriff station but also selling to the local hunter community. He also sold camping equipment out of his store, since hunters needed that just as much, and the touristy town of Silver Lake did have a lot of campers, hikers and hunters visit. So while the weapons were still contracted to the government and Argent Arms operated nation-wide, there was now a physical shop in Beacon Hills, where Chris lived and worked and led his company from. Which meant Stiles regularly ran into him when he went back to visit his dad. He’d met Chris a couple of times at the station too.
Where he hadn’t seen Chris yet, however, was the Jungle. So when Stiles got off the stage after a show, just to be offered a bouquet of flowers, he was completely taken by surprise. He blushed furiously when he met Chris’ eyes because quite frankly, this was not how he had expected to meet his roommate’s father. Then again, at least he was wearing more this time than the first time.
“You told me to come to the Jungle if I wanted to see you in a dress.”
Chris had the audacity to smirk charmingly at Stiles and it nearly made Stiles swoon. What the hell.
“That… That was a joke. And it was months ago,” Stiles did accept the red roses though.
“I’m sorry,” Chris looked worried now, no longer smirking. “I didn’t… I didn’t mean to make you uncomfortable. I just… I’m sorry, I’ll go.”
Sighing, Stiles reached out to grab him by the arm. “No. That’s not… I just…”
“Haven’t seen you lost for words yet,” Chris commented, near fond.
Stiles’ blush got worse and he glared at the man. “I just… I was kind of joking but maybe also flirting but you actually showing up here and with roses is like a really bad idea, because you are my roommate’s father and she’s become like one of my best friends and you also work with my father and it’s messy and it’d going to be weird and-”
Chris grabbed him by the chin and pressed a gentle finger against Stiles’ lips to make him stop talking. “If I don’t get a say in who my daughter is dating, I think she shouldn’t get a say in who I am dating. You’re an adult, Stiles, you can make your own choices. I tried to ignore my attraction to you, but now that I live here and see you practically every week in some capacity… I want you. And I don’t see why I shouldn’t go after what I want.”
Stiles swallowed hard and instinctively stuck his tongue out to lick his lips, just to grace Chris’ fingers. Those steel-blue eyes darkened significantly when Stiles’ tongue licked over the man’s fingers. The blush seemed to be a permanent fixture at this point.
“Bambi,” Stiles offered after a moment. “When I dress like this. Bambi Leroux.”
“Bambi, mh?” Chris gave him a little grin and wrapped one arm around him. “Would you like to dance with me then, Miss Leroux?”
Biting his lip, Stiles offered a broad grin and laid his free arm around Chris’ shoulders. “Why, I think I would like that very much, Mister Argent.”
/break\
Stiles was everything Chris had ever wanted and never knew he needed. The boy was wicked smart, adorable, beautiful, kind, fiercely loyal, sweet but evil when he wanted to be, an absolute brat and yet he would melt under Chris’ touch. Every moment he got to spend with Stiles, Chris felt more alive than he had in years. Since Victoria’s death, he had made his entire life about Allison, about protecting her, giving her the childhood she deserved. Hell, even before Victoria’s death, he had always prioritized the family business, let the weight of his father’s expectations dictate what he did. For the first time maybe ever, Chris was living his life the way he wanted it and he was happy.
He paused surprised when he entered his apartment, just upstairs of his shop, to the scent of something delicious being cooked in the kitchen and to the sound of off-key singing. A small smile spread over his lips as he approached his kitchen and found Stiles in it, hips swaying. The even bigger surprise was the red dress Stiles was wearing though. He’d never seen Stiles in a dress outside of Drag night (which Chris might or might not attend religiously at this point, because his lover was absolutely stunning, not just in the dress, but also the pure joy he radiated when he was on the stage with his friends, performing and having fun).
“...Baby?” Chris asked, unsure. “What do I owe this surprise?”
Stiles whirled around – and nearly landed flat on the ground. Chris was quick enough to catch his boyfriend by the waist, stabilizing him and pulling him close. Stiles batted long lashes at him when he found himself pressed against Chris’ chest.
“Today one year ago, a really hot silver fox walked into my kitchen while I was half-naked,” Stiles grinned mischievously. “I wanted to celebrate our first meeting?”
Chris huffed fondly and shook his head. The two of them had been dating for four months now, so it shouldn’t surprise Chris that his boy wanted to celebrate something so silly. Stiles was unusual and he did like to celebrate everything good in his life. Chris’ heart felt warm at the thought that Stiles considered him something good in his life. Pulling Stiles close, he kissed the boy.
“I adore you,” Chris whispered lowly. “But why the dress, baby?”
“Be—ecause that’s my anniversary present for you,” Stiles rested his hands on Chris’ chest and pushed off enough to look at him, his already long lashes somehow impossibly longer thanks to the mascara. “You could have asked me out any time we met, but you specifically went to the club, with flowers. And I see the way you look at me after a performance. I’m not sure why you’ve never brought this up in the bedroom yourself, but I know a kink when I see one.”
Chris ducked his head a little guilty. “I didn’t… Considering how I asked you out, and also the misunderstanding when we first met, I didn’t want you to think that I’m only with you to pretend I’m with a girl or something. To make you into something you’re not. So I didn’t…”
“Oh, you’re adorable,” Stiles huffed and cupped Chris’ face. “My masculinity does not suffer from you liking me in a pretty dress, babe. I really thought we had this kinda stuff covered when we had the Daddy Kink discussion. So, do you want to call me princess and fuck me while I wear your favorite dress, or did I waste my time shaving my legs for this…?”
Chris gave a low growl and grabbed Stiles by the back of his thighs, hoisting the boy up until Stiles could wrap his legs around Chris’ waist. The kiss they shared on the way to Chris’ bedroom was filthy and both of them were left panting breathlessly by the time Chris threw Stiles onto his bed. Stiles got comfortable on his back and spread his legs in invitation, causing the dress to pool around his waist. Chris quickly undressed himself and then ran his hands appreciatively over Stiles’ smooth legs. He lifted one up over his shoulder and placed a kiss on Stiles’ knee.
“I took the liberty to prep before you got here,” Stiles informed him as he handed over the lube. “Dinner is simmering, but I thought we could make the first round a little quicker so we can eat.”
“First round?” Chris smirked against Stiles’ leg while lubing up his cock. “Someone’s eager?”
“I mean, it’s not just your anniversary, Daddy,” Stiles grinned mischievously and spread his legs.
Chris laughed and bent down to kiss Stiles, slow and deep, while easing his way into his lover’s tight hole. Stiles was loose enough to make it easy, but still tight enough to make Chris groan into their kiss. This boy truly was perfect and everything Chris ever could have wished for.
“God, princess, you’re perfect,” Chris whispered, trailing kisses down Stiles’ neck. “You’re so perfect for Daddy, you have no idea. Just look at you, all flushed and eager for me.”
Stiles’ red lipstick was smeared and his lips were swollen from their kiss, his cheeks flushed and pupils blown. He was the prettiest sight Chris had ever seen when Chris started fucking into him. The red satin dress felt smooth under Chris’ hand as he gripped Stiles’ waist so he could fuck his boy deeper and harder. Soon, Stiles was reduced to a moaned chant of Daddy, Daddy, Daddy .
“Yeah, princess, it’s okay,” Chris groaned. “Daddy’s got you. Can you be good and come for me?”
He wrapped his fingers around Stiles’ cock under the dress and with a howl did Stiles come and then collapse lax beneath Chris. It only took a few more thrusts for Chris to come inside Stiles.
“Happy anniversary, princess,” Chris whispered, pressing a kiss to Stiles’ temple. “I love you.”
~*~ The End ~*~