synopsis ! Dean found out that Jess, your boyfriend of a nearly two years, was messing around with Rory—your Rory. He promised to be there for however long you needed him.
warnings ! explicit language (like 1 curse word) ◞ semi hurt/comfort ◞ a little bit of jess & rory hate ◞ infidelity ◞ betrayal (does this need a tag?) ◞ reader is rory's cousin
word count ! 668
based on ! jessie's girl by rick springfield.
Dean’s been your best friend for about a year. You first met him while picking up some last minute ingredients with your aunt at Doose’s. You were baking Rory’s favorite cupcakes for her birthday, and of course, were missing the most important part—the pumpkin purée.
Of course, you could've made any other flavor of cupcakes and Rory would have still inhaled them, but this time she asked specifically for pumpkin cupcakes. And honestly, who were you to deny your favorite (and only) cousin?
Although, it did help that your boyfriend loved the cupcakes as well. But no one had to know that.
Which led you to Doose’s, because you weren't going to upset Rory on her day. It didn't take but three minutes to find the purée and head straight to check out. This next part was your favorite.
Get to check out, have a nice but small conversation with the workers, and go back to your aunt's house to start on the baking. What was usually one of the quickest moments of your day, gradually became the longest. Not that you were complaining.
You went to the market with one thing on your mind, and ended up leaving with a new friend. And your purée.
A year and a half year later, Dean was your best friend, and Jess was still your boyfriend.
February just started, which meant it was cold and the perfect excuse to make some more cupcakes. But honestly, who were you kidding? In Lorelai Gilmore’s house, an excuse for wanting sweet treats was never needed.
But of course you were, once again, out of an ingredient. Although this time it was ground cinnamon, and since Dean was the only other person at home, you sent him to Doose’s, knowing he likes the walk alone.
“Finally,” you yawned as Dean walked in, finishing up with the wet ingredients, something you started to pass the time. “Welcome back.”
“Hi. Sorry..” he smiled. It was small and hesitant. “Got a little caught up.”
You waved him off. “Don't worry about it. Everything okay over there?”
Over there. You were talking about Doose’s, he knew that, but he so badly wanted to blurt about what he’d seen on his walk back home to you.
“Yep, all’s good. I, uh.. saw Jess. And Rory.”
You blinked. “Okay.. I see them sometimes, too.”
Dean almost smiled. “No, I know. It’s just..” he sighed, saying your name like it pained him physically. “They were.. close. Too close.”
“Too close?”
He nodded, waiting patiently for you to catch on. And you did, eventually.
“Oh.”
“Oh?” he asked, eyebrow raised.
“I mean,” you sighed. “I don't know what to say.”
Dean walked over to you, sat the cinnamon down with the other dry ingredients, and pulled you into a hug. “You could try What the hell, or maybe even Oh my gosh. Either one works, you know. Just… are you okay?”
Were you okay? Honestly, you weren’t sure. You cared about Jess, a lot, and Rory was the closest thing to a sister you'd ever had. You never would have pictured the two of them together. Sometimes, you actually thought they hated each other.
Though, thinking of that now, maybe they wanted you to think that way. Because the only thing worse than your two favorite people in Stars Hollow hating each other, was the possibility of them loving each other.
So, no, you weren't okay. Not really. It wasn't anger at the fact they were seeing each other, or sadness at the thought that Jess didn't really love you. You were angry that you believed him when he whispered those three words in your ear at night.
You were sad that Rory could be enough for Jess to not want anyone else, while you were just a stand in until she was willing to date him.
“I’ll be okay,” you sniffed, smiling. “Just.. stay with me? Please?”
Dean nodded, pressing a kiss to your forehead as he pulled away. “Of course. I'm here when you need me. Always.”
author's note ! i only realized after i finished writing that it does not follow the song whatsoever but who cares its late and im tired!!! for you @sstrangerheartss i love you
synopsis ! Dating someone in Stars Hollow could only be kept secret for so long. When your relationship with the new boy in town, Dean Forester, became public knowledge, it was only natural for him to climb in through your window multiple nights a week.
warnings ! explicit language ◞ mentions of handjobs ◞ mentions of semi-public activities ◞ smut!!! ◞ oral (f!receiving) ◞ fingering ◞ finishing untouched ◞ slight fem!dom ◞ sort of inexperienced!dean ◞ praise kink? ◞ this might be a bit off canon since i've never actually watched gilmore girls (oops...)
word count ! 897 (roughly)
based on ! main thing by ariana grande.
Dean Forester wasn't the most experienced person on earth when it came to sexual situations. In fact, the furthest he’d ever gone with anyone but his current girlfriend was a very non-sexy make out session.
If only that girl could see him now—pinning you, his ever so gorgeous girlfriend of nearly a year, to your own bed. You were wearing his hoodie (which, honestly, was what landed you in this position in the first place). It was already too big on Dean, which meant it swallowed you whole.
The only parts of you that were able to be seen below your neck were your legs, covered in sweat, spit, and some other bodily fluids your brain couldn't comprehend right now, but you're sure you know what they are.
Your brain was fuzzy and it was hard to think, because just down south, there was Dean. His long, slender fingers were working inside of you, curling up and just feeling too good.
He looked ethereal. His hair was falling into his eyes and his face was flushed red, sweat beading down his forehead despite the freezing temperatures outside. He was laying on his stomach, rutting into your mattress with a speed that matched his fingers.
“Dean,” you gasped, bucking your hips.
No answer. Lifting your head, you could see he was too focused on the way his fingers went in and out of you, so focused it was as if he couldn't even hear you speaking.
“Dean, I—”
“Can I….” he stopped short. Somehow, his face was more red than before. His fingers were still moving, albeit much slower now. His eyes flickered down. “I wanna… try something.”
“Yeah? What’s that?”
Dean whined. “Please, don't make me say it.”
“You gotta, baby. How else would I know?”
His face was so red you thought he might burst into flames. “Can I eat you out? Please?”
It was your turn to go red. You’d been with only one other guy, and he was too embarrassed by the mere mention of pleasing you to ever do anything besides a handjob in his car (at least, what can be considered a handjob. There wasn't much going on down there.)
Unlike the last, this was happening at night, and in the privacy of your own room. It was the preferable choice. Instead of trying to shield away from the prying eyes who—with just one peak in your direction—could find out exactly what you were doing.
And you thought—or more so, you hoped—that Dean would stay after, and not get up and leave after getting his rocks off with something other than his own hand.
He wouldn't. You knew that. Dean was the sweetest boy you’d ever had the pleasure of meeting.
“Oh, Dean,” you bit your lip to suppress a smile. “it's fine, you don't have to—”
“I know, but I want to.”
With a look in his eyes, you could tell he was being sincere. They were filled with lust and desperation. You nodded. “Okay.”
Dean didn't wait. The second he got the okay, his lips were attached to your clit, and he sucked. His fingers were back to moving at a quick pace, the sound of your wetness and whines filling up the room.
“Oh, fuck, Dean.” you whined. “Just like that. Doing so good f’me.”
Dean whimpered into you, hips rutting into the mattress again. He looked into your eyes from behind his hair, brows furrowed and eyes glossy.
His fingers curled up again inside of you, free hand pushing on your stomach to keep you still. You hiked your legs over his shoulders, closing his head in between your thighs. You could feel yourself getting close by the second, inner coil tightening so fast and so good.
“M’close,” you whimpered.
Dean closed his eyes and moaned, and with a final nip at your clit, you were tumbling over the edge, back arching off the bed as he kept thrusting his fingers.
Finally coming down off your high, you gazed down at Dean, who looked embarrassed, but was still giving a shy smile, closed mouth smile. Half his face was dripping with your arousal as he shyly (but still hotly) licked his fingers clean.
“Was that… okay?”
You shook your head. Dean's face dropped before he frowned. “...Sorry, I—”
“If was fucking fantastic.” You laughed. “Jesus, Dean, where did you learn that!”
His face turned burning red, only this time from your words, and not your actions. He mumbled a shy Thanks, sweetheart. You seemed to have a great effect on him.
“I suppose it’s my turn to return the favor, yeah?”
Dean bit his lip. “Oh, well, actually… My needs have, uh, been fulfilled..”
You cocked your head to the said, eyes brows raised. “Fulfilled?”
He nodded slowly, sitting up, and now you could see it. There was a big, dark, wet patch on his crotch. Looking under him, you could see there were also a few dark patches on your throw blanket.
Sure, some of it was from you, but you also knew damn good and well that Dean had become a victim of finishing untouched.
“I'm sorry! I'm sorry I—I don't know what… this has never….”
“That's kinda hot, actually.”
Dean’s eyes went wide, mouth falling open. “W-what?”
“You think you've got enough in you for another round?”
authors note ! thank you my precious @sstrangerheartss for the idea i love you so very much
