Gilmore Girls x Reader Gay Oneshots

Call Me Maybe - Dean Forester

Moving from a big bustling city to a small, unheard of town in the middle of nowhere certainly wasn't easy. This you knew for sure after your mom announced you'd be moving to Stars Hollow, Connecticut. You hadn't known what to expect, having lived the life of busy streets and skyscrapers since you were born.

What would it be like? A desert with broken down houses and tumbleweeds? A ghostown blanketed in permanent silence? You really, really weren't keen on the decision. To your surprise, however, it was quite the opposite of what you'd envisioned. Stars Hollow had a nice, homely feel to it. It wasn't New York, but there was a decent amount of people on the streets and cars on the road. The leaves grew crisp in the grasp of autumn, drawing patterns in the breeze.

The townspeople were unbelievably welcoming, making sure you felt like one of them already. With the Halloween celebrations taking place, there wasn't one second of boredom to spare. Luke's had essentially become your second home. Life was good.

This takes us back to present time, as you're currently heading towards the local grocer. Your mom had some errands to run for the day, so she put you in charge of groceries. A soft jingle rang throughout the store as you pushed the door open. You were greeted with a smile from the cashier and a quick "good afternoon" while he was bagging vegetables. You gave a small nod, taking in his appearance for a moment. 'Cute', you mused to yourself. He was a brunette, standing at 6ft at least. Definitely your type. But you tore your focus away from him onto the list you were holding.

Bidding his last customer goodbye, Dean found his eyes tracing back to your form wandering between the aisles. You were unaware of his gaze as you hummed softly to the jazz music playing from the speakers. He wondered why he'd never seen you around before. You looked about the same age as him. He found you... pretty. Could a boy be pretty? Well Dean figured you could give female models a run for their money.

He was so lost in his thoughts he didn't notice you coming up to him until he felt a light tap on his shoulder. "Excuse me, can you help me find the cinnamon please?" You asked politely. "Sure thing, follow me." You paced behind him as he led you to one of the back aisles. "Right up there." He pointed to the boxes stacked on an abnormally high shelf. "Um... Could you get it down for me?" You flushed in embarrassment. Dean chuckled a little, finding it adorable how tiny you were. "Here," he placed a box in your hands. You thanked him, about to go to the checkout but he stopped you. "Wait, I don't think I've seen you in town before. Are you new?" he asked. "Yup. I moved here a couple days ago from New York City."

"New York! Jeez, that's pretty far from here."
"Mhm, my mom wanted a fresh start. Said life will be better once she finds a new job and I settle in to a different school."
"Stars Hollow High. I'm starting next week." You smiled. "Oh same here! You know, if you need someone to show you around..."
"I'd appreciate that," you paused, scanning his name tag. "Aw shoot, I didn't even introduce myself!" Dean realised, "I'm Dean. And you are?" He raised an eyebrow. "(Y/N)."

"Well nice to meet you (Y/N)." He grinned. "Hey how bout I give you my number, we can meet up sometime if you want." He offered. "Okay, nice meeting you too." You giggled, taking the slip of paper from his hands. "Thanks Dean, I'll see you later!" You waved goodbye to him after paying and exited the story, leaving him grinning like an idiot.

Dean sat staring at his phone, anticipating the moment it'll buzz to life and display your name on the caller ID. His shift ended 2 hours ago, but he'd heard nothing from you so far. Stupid, you didn't tell him to call today. You've just met each other after all. Regardless, he wanted to hear your voice again. Right after that thought, a series of rings sounded out and your name flashed across his screen. He swiped right, trying to suppress the grin on his lips. "Hey (Y/N)." He greeted. "Hi Dean." You giggled. Such a precious sound. "What are you up to?" Dean asked, flopping down on his bed. "Nothing much," (Y/N) murmured, "just showered. You?"

"I'm talking to you, duh."
"Other than that." You rolled your eyes. "Nothing, really. I was waiting for you to call. You took your time." Dean pouted to himself. "Sorry," you sighed, "I just had to gather up the nerve." This caught Dean's attention. "Nerve for what?" You could almost face palm at his ignorance. "Um hello? It's not everyday some cute guy at the shops gives you his number. How do you expect me to react?" Dean smirked on the other end. "So... You think I'm cute?" His voice laced with cockiness. "Yes, of course I do idiot. How could I not?" It was your turn to pout. "Aw, I'm glad you think so sugar. The feeling's mutual." He chuckled. "Sugar?" You cringed, "that's a terrible petname. Try again."

"Okay," Dean thought for a bit, "how about baby boy." You gulped, feeling heat rise to your cheeks. "Better. Much better." There was silence on the other end before Dean spoke up. "You know baby boy, I find it hard to believe guys haven't tried to give you their number. No way a cute little thing like you has difficulty with romance." You hummed. "Okay maybe I exaggerated just a little. Wanted to make you feel special." You fiddled with your shirt, liking the way this conversation was going. "You do make me feel special, sweetheart. I'm so lucky that you even gave me a chance. However," he paused, "you still lied to me. I don't like liars."

Your heart sped up hearing the drop in his voice, and a flame of arousal burned at the pit of your stomach. "I was just kidding around, Dean. It's no big deal." He ignored you. "Only bad boys lie. And you know what bad boys deserve? Punishment." He licked his lips. You whimpered, feeling your pants become uncomfortably tight. "You know if you were here I'd bend you over my lap and spank your pretty ass raw, mark you up so well. You'd look so pretty baby, covered in my handprints. You'd like that wouldn't you, slut." You whined at the filthy promises, grinding your hips down on the mattress in search of any kind of friction. "Dean, please..." You hear him growl, the sound sending shivers down your spine. "That's daddy to you slut."

"Daddy! I need you!" Dean groaned, placing a hand on his aching crotch. "Touch yourself babyboy. Touch your pretty little cock for me. Fuck yourself open." You quickly discarded your pants and boxers, gasping when the cool air hit your cock. There's a shuffle as you retrieve the lube from your drawer. "Do you know what flavour this is, daddy?" Dean hears the click of a bottle cap being undone. "It's peach. You like peaches?" You get a moan in response. "It'll leave me tasting so good. Wish you were here to take a bite." You relaxed against the pillows, spreading your legs for access. You circled your entrance, leaving a wet squelch. "I'm putting the first one in." You said. Dean's mind was so hazy with arousal that he could hardly process your words.

The intrusion didn't hurt, but it wasn't pleasurable just yet. You slid in your index, biting you lip at the stretch. Moving your other hand to your cock, you found a decent rhythm to work with. Your gaze became blurry and you couldn't hold in the noises as the pleasure began to take over. Dean wasn't any better, his hand working up and down his girth. He couldn't get enough of your pretty moans. He could only imagine how you looked, all flushed and sweaty, back arching beautifully while working yourself to an orgasm. "Tell daddy how it feels." He grunted.

"F-Feels so good. Wish it was you instea- AH!" White spots painted your vision as you struck that bundle of nerves inside you, pleasure filling your senses. Sliding in two more fingers, you aimed to hit that spot with every thrust. "D-Does daddy feel good?" You mewled. "Daddy feels so good babyboy, you're doing so well. So good for me. My obedient little angel, hm? Wanna wreck you so badly. Wanna turn you into a whore that worships my cock, would you like that? Being my little cockslut? Of course you would, baby. I'll make you feel so good. You can't get enough of me. You can't even wrap your whole hand around it, slut."

"D-Daddy... I don't know how long I can, ngh, continue," you panted, "I'm close!" Dean groaned, "me too baby. Cum for me sweetheart." You came with an earth shattering cry, painting the sheets in white. You heard Dean grunt one last time before silence fell on both ends.

"That was fun." Dean grinned. "It was." You sighed in content. "Hey listen- I'm sorry if I got too carried away with the stuff I said. I tend to get a little heated in the moment." He apologised. "Don't worry! I actually enjoyed it. It was hot." You smirked. "Dirty boy." Dean snickered. "But I wanted to ask if you wanted to go to Luke's tomorrow?" You smiled, slipping on an oversized hoodie. "I'd love to. It's getting late though. I'll see you then, okay? Goodnight." You said softly. "Sure thing, (Y/N). Goodnight. Sweet dreams, beautiful."