Sam: You stirred in bed until you slowly opened your eyes to your brightly lit motel room. Sam, your boyfriend, was snoring lightly next to you with his arms latched around your waist. You smiled at him, kissing his forehead, before slowly prying yourself from his grip. You made your way to the bathroom, doing your business and washing your hands and face. You made your way back into your room to see Sam still asleep and grabbed some clothes out of your duffel bag. You were about to pull on your clean shirt when you felt someone wrap their arms around you.
"You didn't tell me you had a tattoo," Sam said tiredly as he mentioned the small black rose on your waist. His fingers lightly ghosted your skin as you squirmed from him tickling you slightly. He leaned down and kissed your lips, leaning his forehead against yours. "I like it. It suits you." Sam kissed you again, walking off to go to the bathroom.
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Dean: You were groaning in the back of the Impala as you held the ragged piece of flannel against the giant gash on your upper arm. Dean sped down the street as he looked at you through the rear view mirror every two seconds. It was his fault you were hurt; he had tripped and knocked you over and you felt right into a vamp. The vamp ripped your arm to shreds, leading you to where you were now. Sam was back at the motel doing research and was supposedly getting all of the supplies together to fix you up. You felt yourself nodding off, and the last thing you heard was Dean yelling.
"(Y/N), babe, stay with me."
You woke up and blinked a few times to adjust to the sudden light. You heard footsteps come up to and then saw Dean's face. He smiled sadly and kissed your forehead, making you smile a little. He nodded towards your arm and you were confused for a minute, until he said what he meant.
"So, tattoos, huh," Dean asked as you nodded softly. He slid into bed next to you and helped you sit up. "How about you tell me what they all mean?"
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Cas: (this one isn't gender inclusive sorry babes) It was extremely hot in the bunker. The AC had broken and the summer heat was becoming more and more intense. The boys were never home so it didn't bother them, but you were always doing research for them and were becoming irritated. You were so used to wearing a sports bra and shorts every day that when the boys said that they were on their way home, you had forgotten that you were wearing really revealing clothes.
You sat in the library, reading some books, and weren't bothered by hearing the creak of the door. You looked up briefly to smile at the boys and returned to your book. You felt a few kisses on your forehead and heard 'hello' a few times, but you didn't pull your attention away from what you were focused on. You heard a chair scrape on the floor and Castiel began to speak. You finished the sentence you were on a then looked up at him, listening to him talk about the case.
"...and it was fun being able to fight, but I missed you greatly," he said as he finished. You smiled at him, standing up to kiss him on the lips. Cas stopped you and his hands trailed down to your stomach. "What's this, darling?"
"It's a tattoo I got a few years back," you said as he traced it.
"I want one, too. They look fun," Cas said as he looked up at you with wonder in his eyes.
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Jack: You were silently sitting in the library of the bunker when you heard the door open. You looked and saw your best friends, noticing they had a boy with them. Dean came up to you and gave you hug, muttering something about 'the devil's son' or whatever. Sam smiled at you, kissing your forehead and sighing.
"(Y/N), this is Jack," he said as the boy gave you a small smile and waved. You stuck your hand out for him to shake, but he stared at it, confused. Sam slid over to stand next to him and instructed him on what to do. Jack grabbed your hand a shook it, stopping suddenly. You followed his gaze to the small tattoo on your finger.
" 'Darling', " he read as he looked up at me. "What does that mean?"
"It's, uh, something my mom used to call me," you replied as you walked away to resume your spot in the library. He followed you, still looking at your hand and asking questions. Looks like you've got a shadow.
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