Your father had dropped you off at Bobby Singer's house more times than you could even remember, and when your father died, you had moved in there. Bobby had tried his best to provide you with an actual childhood, and you were grateful. John Winchester had also dropped his sons off at Bobby's for as long as you could remember. They had been your only friends when you were little. Back before girls had cooties and Dean pulled away from you to play with cars and talk about guns. Sam had pulled away too, of course, he was a guy. But, he had still played with you when you asked.You both loved to read, neither of you were popular. You made a good pair. You looked out for each other. And you'd always had a sneaking suspicion the only reason Dean put up with you back then was that you protected his little brother almost as much as he did. Dean though? He had been your crush for as long as you could remember. The bright green eyes, the strong jawline. What wasn't to like? Not to mention the way he cared about everyone and everything, even if he pretended to be this hardass.
*You hated high school. It was literally worse than any monster you could come up with. All you wanted was to be at home. You also really wanted some pizza. Once you reached Sam's locker, you announced this to him.
"I very much want to be at home. Eating pizza. In my bed."
He shut his locker and laughed at you. "Everyone wants that. Plus I thought we were gonna read the new Harry Potter book tonight."
"Yes definitely. That's a grand plan as well. Just as long as I get pizza."
"I'll fix you pizza. Bobby has like twelve in the freezer. For a minute there I thought you were skipping out on me."
"Never. Goblets, fire, voldemort, I'm all in." You looked at the clock and saw you had two minutes to get to your fourth period. "Crap, I'm gonna be late." You said as you started walking. "See you when you have pizza for me!" Sam just laughed and waved at you.*
You smiled at the memory and got up from the couch in Bobby's living room to get more...pizza...maybe you had a problem…
"Well look who finally got off the couch."
"Hey, I was watching a movie." You got your pizza and sat down with him at the table. He was cleaning guns and sharpening knifes, ya know, the usual.
"Yeah, sure. And I'm a monkey's uncle. You were in there thinking again."
"And how do you know that?"
"The thought is still written all over your face."
Damn, he knew you. "Yeah. Well."
"He's happy you know."
"Yeah." You breathed. "I just…"
"Wish he hadn't left you out of it."
"Yes." You looked at him then. "But it's really okay. I'm just feeling nostalgic, is all. Just missing the past..." You trailed off.
Bobby seemed to understand you needed a subject change.
"Oh, did I tell you about the infomercial I saw last night? For this rag that's supposed to soak up whatever you try to wipe up. Well the idjits had me thinking, don't all rags soak up whatever you wipe 'em through? So I got it, and I'm gonna test my theory on the matter as soon as it comes in."
He actually looked pretty proud of himself, so you tried not to look freaked out. "Wow, well that'll be awfully fun. I can't wait to watch."
"Yeah, for sure. We'll make it an event."
"That sounds like an awesome plan Bobby." You smiled. "I think I'm gonna go shower. Get ready for bed. It's getting darker earlier since we had to switch the clocks. And you know me, always asleep once it gets dark outside."
"Okay." He smiled, and went back to cleaning. "Oh, wait. You don't have to worry about the hot water anymore. It should stay whatever temperature you set it at."
"Cool, thanks for fixing it."
"Anytime. A person shouldn't have to worry about getting burned to death in their own shower." He grumbled and shook his head.
Once you showered and found some pajamas, you laid down. Even though it was only 7:30. Who really cared? It wasn't like you had any place to be. You had almost fallen asleep when you heard the knock at the door. You heard Bobby grumble and pad down the hallway. Heard him open the door, heard the hiss of pain as he dragged a silver blade across the mysterious person's skin, heard the splash of the holy water. Then you heard him drop everything and hug whoever was at the door. You assumed they would eventually speak, so you got out of bed and moved to stand next to your door.
"What're you doing here boy?"
"I'm looking for Y/N. She is still here right?" The voice questioned. It sounded way too familiar.
"Yeah, course she is. What'd you want with her?"
"I'm going to Stanford to get Sammy and I want her to come with me."
Wait a minute...Dean?
"Now what're you gonna do a thing like that for? The boy got out of the life. That's what he always wanted. Let him be."
"I can't. Dad's missing. I don't know anyone else to take with me. He's my brother."
"Well, alright then. I understand you there. Still don't agree with ya, but what am I gonna do to stop ya? But you aren't taking Y/N with you. No way no how."
"What? Come on, why?"
"Because she's finally got some peace ya idjit!" Bobby yelled. He seemed to remember you were just right upstairs "sleeping" because he was quieter when he said, "You two just up and left her. You know what that did to her? Sam was her best friend, and he left to go follow a dream, so she understood that one. It hurt her, don't get me wrong, it still does, but she understood why he left. You, on the other hand. Just left her on morning. Not a word. Not a goodbye, not a see ya later. Nothing. And it hurt her worse than Sam." Bobby took a breath. "You could have at least called her. Don't give me that crap about having to hunt. Every motel room has a phone. That girl is like my daughter. I love her, and I'm not gonna let you hurt her anymore."
"Bobby...I would do anything for her. Please, come on. I don't think I can take it if Sammy says no. Please, I'll never hurt her again I swear it."
"No."
"I'm gonna sit on your porch until you say yes. She'll see me then. Then she'd get to choose for herself."
"You'll be sitting there for a while then."
"Bobby...you're like a father to me too...you know if I make you a promise I'm gonna keep it."
They were both silent for a while, and you figured Bobby had shoved Dean onto the porch to go back to sleep. You crawled back in your own bed, and huddled underneath the covers.
"Y/N? You awake darlin'?"
Oh.
"Hm? Yeah?"
"Dean's downstairs. Wants you to go with him to get Sammy from Stanford."
"Oh."
"You don't have to go if you don't want to. I can send him and that damn car right on their merry way."
Well? Did you want that? You were in love with Dean. And you missed Sam terribly. But you didn't want to disrupt his life if he was really happy. But what if he's not?
"Um. No, it's okay. I'll go."
"You sure?"
"Yeah. Just tell him I have to pack some stuff."
"Alright. Now, if he starts to bother you, you just call me. I'll be there in no time."
"I know." You got out of bed to hug him and he went back downstairs.
You packed up a duffel with a few outfits and some shampoo, and headed downstairs too. When you saw Dean again your heart almost leapt right out of your chest. He was just as gorgeous as you remembered.
"Long time no see pretty girl." He said as he crossed the room to hug you.
"Hi Dean."
"Well. Bobby, see you soon." Dean said as he hugged the older man.
"Take care of her."
"Bye Bobby." You said as you hugged him. "Be back soon."
"You better be."
With that the two of you walked outside towards the Impala. You slid in the passenger seat, which was weird since you had only ever been in the back when you were little. You turned around to throw your bag back there, and just seeing it sent you reeling back into the past.
*You had thought the leather against your back had felt nice, but it was nothing compared to the feeling of Dean on top of you.
"Hey pretty girl."
"Hi."
He started kissing down your neck, and you probably resembled something close to a puddle of mush. You had loved Dean for ages, and now here you were. About to lose your virginity to him. How you had gotten here was pretty foggy. You knew it had something to do with spin the bottle. And some very full bottles of alcohol on Dean's part. You were sure Dean wouldn't remember it in the morning, and that only slightly hurt you in that moment. You didn't have much time to dwell on it because now Dean was under your shirt and he had your nipple in his mouth and you really were convinced you were floating.
"D-dean?"
"Hm?" The vibrations of that around you were really something to get worked up about, and you almost forgot your question. Almost.
"Are you sure? You did drink an awful lot and I ju-"
"Course I am. I didn't really drink that much by Dean standards. I wanna do this. Unless you don't, in that case we stop right now."
"No, I wanna do this."
He grinned, "Good." He continued with his early project, and then moved down to work you sweats and panties off. Then all of a sudden his mouth was on you and you really were floating this time. You came so fast Dean decided he hadn't had enough of tasting you yet and kept licking right through your orgasm and straight into another one. Then he was back at your neck and you realized this was an awfully one sided affair, so you said something.
"Dean?"
"Hm?"
"I-ah-I feel li-oh-ke I'm not do-oing anything for y-you."
"Oh, another time. Don't worry about that. Just enjoy. This is about you, not me."
Then his fingers were in you and they were twisting and stretching and you didn't really have time to protest Dean's comment because now you were about to cum again, and you really never wanted to stop having sex with Dean.
"You ready?"
"Mhm please."
That was all the permission he needed to line himself up and push into you.
"O-oh my god Y/N."
When he came, he sent you right over the edge again too.
You woke up in your bed with a very warm something under your head. You moved a little to realize you were wrapped around Dean and that didn't make any sen-oh! As last night came flooding back to you in all the best ways, you realized you were, in fact, very naked. As was Dean. And you were very much in Bobby's house. Who would kill you both if he happened to walk upstairs and peek in.
"Dean." You shook him a little. "Dean." A little harder. "Dean!" Finally he stirred.
"Hm? What is it?"
"Us. We're chilling here naked in Bobby's house."
"Shit." He jumped up and started to run out of the room, realized he still hadn't put clothes on, and stopped to find them. Once he was good and dressed, he looked over at you, "Last night was fun. Let's do it again soon." And then he was gone.*
"Y/N?"
"Yeah?"
"You okay over there? You've been staring out the window for ages."
"Oh, yeah. I'm good."
"Okay. Just thought I'd check. I was beginning to think I'd kidnapped you."
At that you laughed, and he seemed satisfied you really were okay and went back to just driving and you went back to staring out the window and trying not to think of what happened so often in the backseat of this car.
Eventually, you guys got to Stanford. And after all that confident banter in front of Bobby, you saw some of the scared little kid you used to know come through.
"Hey, Dee? It's all gonna be okay in there. Whatever Sam says and does is all gonna be okay. Because you're his brother. And he's never gonna do anything to hurt you on purpose. Well, without a purpose I guess I should say."
He took a big breath. "Yeah. Yeah, you're right. It's okay." Another breath, and the confidence was back. "Come on, kid let's go get him."
"Off we go."
By the time you actually figured out where he was staying, which room he was in, and which floor he was on you were both exhausted. But nothing would have prepared you for what happened when the door opened. Because Sam didn't open it. A girl did. And Dean almost bit her head off just for the confused look on her face.
"Yeah yeah we get it, you don't know us. Whatever. Is Sammy here?"
"Sam?"
"Yeah. Sam Winchester?"
"Oh. Yeah. He's in here."
She shut the door, and Dean looked at me for an explanation.
"Did she- did she really just slam this door in my face? Y/N tell me she didn't just slam this door in my face."
Then it opened again. This time with an annoyed Sam behind it.
"Dean? Y/N? What are you doing here?"
"You really want me to tell you out here in the hall? Where all these people will here? Or would you prefer to send your booty call home and let me tell you inside?"
"First of all, she's not a booty call. She's my girlfriend. Second, I don't want you to tell me anything because I don't want to see you."
He started to close the door in your face, so you spoke before you thought. "It's your dad. He's missing."
I'll spare you the gory details of the hunt (and the god awful fight that happened after that conversation), but we found out there was some weird stuff happening. We figured out that it was a ghost. Dean and Sam found their Dad's motel room where his research suggested it was a woman in white. A few bruises, scrapes, and bodily disfigurements later the woman in white was gone. And Sam was about to be too.
"Dean I don't want to hunt with you again. Don't get me wrong, it's been really great to see you. Both of you. But I have a good life here. I love Jess. I love lawschool. Just let me be here now. It's where I want to be."
"Fine Sam."
"Really?"
"Yeah, whatever. It's not surprising that you don't want to find Dad, so go. Go do whatever."
Dean dropped him off at his apartment with a nod. Sam hugged you before you sat down in his spot and turned back towards the apartment complex.
You had barely gotten two feet down the road when you saw it.
"D-dean stop."
"What, why?"
"J-just, just stop. Stop and g-get out of the car and turn a-around. Now. I'm not kidding."
He listened that time, and he was gone before you even got out of the car. You ran after him, while calling the fire department, because holy hell were they gonna be needed. You waited for as long as you possibly could before you ran in after Dean. But, you ran right into him and Sam on your way there.
"God, thank god, help me."
You grabbed Sam's other arm and wrapped it around your shoulder. You almost asked about Jessica, but the way Sam was screaming and the ease with which he let you have his arm told you there was no need too. The three of you stood there long enough to let the fire department know that Sam wasn't to blame. His girlfriend was dead, he didn't need a man hunt. You were walking back towards the car when Sam said it.
"I'll go."
It was hoarse and broken, but it was there. None of you said anything about it. You got in the back, and Dean put Sam in the front seat. Once he slid in the driver's side, Dean winked at you in the rearview mirror.