How Could You

If Only We Could Dream

You weren't quite sure what to do with yourself. You felt awkward talking to Dean, as it always ended with one of you leaving the room in silence. You didn't want to bother Sam, he was trying to help you. And you clearly weren't accustomed to researching the way he was. Not in this type of place, at least. Sure you had all the knowledge at your fingertips, but you couldn't even imagine where to begin looking. Or what you were even looking for.
You wished you could go outside and wander around the place, but you were too afraid of putting yourself in danger. Instead you took it upon yourself to explore the bunker, eventually making your way to its garage full of beautifully maintained antique cars and motorcycles. "Holy shit," you whispered to yourself. You probably marveled at the automobiles for quite some time, you just couldn't seem to draw yourself away from the garage. It felt weird to just go in, gawk, and then leave.
At some point, you found yourself sitting in one of the older cars, a black oldsmobile-looking one, behind the wheel, fantasizing about what it would've been like to live in the forties and be in a gang with real gentlemen. It was something you fantasized about often, an idea you couldn't get out of your head. You would've killed to live in that glamorous time.
When you finally decided to get out of the car and leave the garage to adventure more, your body froze when you saw him standing in the doorway. He had his arms crossed and he was leaning against the doorframe, but when you made eye contact he began walking towards you coolly, his long arms swinging at his sides as he sauntered over to you. "Wouldn't have expected you to be into oldies cars," Sam said, his lips halfway turned up into a smile.
"You weren't supposed to see that," you told him, your body still tensed up with embarrassment.
He chuckled. "It's okay, no judgement. I've seen Dean ogle at plenty of muscle cars over the years. Honestly, it's kind of cute you picked this one to obsess over."
"Oh it's cute now, is it?" you teased him. No, don't do that, don't flirt with him. You already fucked Dean and that was a big mistake, your instincts told you.
You saw the blush rise in his cheeks, but he tried to play it cool. "Sure," he said. "I mean, just look at the car."
"Mhm. Now I feel like you're just insulting my taste in cars but you used the word cute so I wouldn't get offended," you gave him a hard time. STOP FLIRTING, your brain shouted. You desperately wanted to listen, but it was too easy with Sam.
Sam thought before he spoke. "No, I really do think it's cute," he said. You then understood why he thought before he spoke. "Hey, I really need a break from research and other hunting related things- what do you say we go out to a bar tonight, have a little fun?" he asked a few moments later, after much hesitation.
Now it was your turn to blush. "I mean... would it be safe? For me? After the whole demonic possession thing... I just... I don't want to take any risks..."
The change in Sam's facial expression from excitement to the realization that you were right broke your heart. "No. No, you're right. I can't believe I didn't think of that. Stupid of me to ask."
When he walked away, you caught up to him and placed your hand on his arm- oh my god, his muscles, your thoughts interrupted. "Sam? Another time? Soon, I hope," you told him.
His happiness returned. "Just tell me when," he said.
Sam walked with you back to your room, understanding that you still needed rest from your three month ride along in your own body. He assured you that you could talk to him whenever, about whatever, before turning around to head back to the library. When you saw that your door was closed, you were a little confused, since you left it open, but figured it wasn't a big deal. That was, until you opened it to see Dean sitting on your bed. He looked torn apart, honestly he looked like he was dying. But it was bigger than you, it didn't even have anything to do with you. According to Sam, he was dying, the trials would kill him. You thought nothing of Dean's presence, thinking maybe he wanted to apologize or just wanted someone to talk to about what he was going through. You completely understood that he wouldn't want to talk to Sam because Sam would only try to talk him out of finishing the trials. After all, you hadn't left Dean because you didn't like the guy, or you didn't get along. You just didn't work well together on hunts. And you were okay with accepting that, you had no problem being a friend. You just didn't want commitment. That's what scared you about how easy things were with Sam.
And that's why, once you got inside and closed the door, you didn't stop Dean. He stood up from the bed, came over to you, and just wrapped his arms around you and dropped his weight against you and buried his head in your shoulder. You simply embraced him in return and let him relax against you, let him lean on you. He wasn't crying, he was just tired. Nothing about it confused you. You just accepted it.
Until Dean turned his head into you and started kissing your neck. "Dean," you said, trying to catch his attention, thinking maybe he was in a trance of some sort. But he didn't stop. "Dean, what're you doing," you said softly, but if you were being honest with yourself you weren't even trying to get him off of you. It felt too good, too intimate, and after everything you'd been through recently, intimacy was what you were craving most. You finally brought yourself to release your arms from around him and place them on his chest, but by then he had started nibbling your ear. "Dean, please," you said, intending it very differently than he took it.
"Please what," he murmured right into your ear. The way he said it turned you on like no other, but you knew this needed to stop. You just didn't want to stop it yourself.
"We shouldn't," you tried to make an excuse.
That's when he pulled away- but only a little, just enough to look you in the eye. "Why not?" He still held you in his arms.
"I don't think... that we... feel the same way... about each other... I think that the last time we slept together was a mistake. And I don't want to make another mistake..." you struggled to get the words out.
His arms fell to his sides. "So that's all I am to you? A mistake?" Dean asked, clearly hurt.
"No, Dean. You're not a mistake at all. You're my friend- my savior, honestly. I could never regret meeting you or having you in my life. But we were drunk... and frustrated with each other... and we had to blow off steam. Dean, I really wish it hadn't happened the way it did. I hope you can understand that."
"I understand that that's how you feel. And I respect that, but I don't feel the same way."
"I don't... What do you mean?" This can't be good, the voice in the back of your head told you.
Dean sighed frustratedly and balled his hands into fists. He glanced down before stepping forward and taking your face in his hands, pulling you in for a kiss. Not rough like the last time, but still needy. Either way, it was not the way he had kissed you the last time. It was different, and you couldn't quite put your finger on what made it feel sweeter. When he pulled away after what felt like hours, he said, "Don't tell me that didn't feel real to you."
"Even if it did, it doesn't matter," you muttered.
"Why not? Hm?" he asked. You could tell that even though he was trying to be patient he was upset.
"Because you're going to die doing these trials. And I'll lose you. I'd rather lose a friend than a..." you couldn't even say it.
"I have to finish what I started."
"I can't be with you knowing you're practically going to kill yourself, Dean. I can't do this unless you give up the trials."
"I can't do that. You know I can't." Dean wouldn't budge and you knew it.
"Well, Dean, you know I can't do this," you gestured between the two of you. "I just can't."
"You sure about that?" he asked in a low voice.
Of course he would make you doubt yourself. So you kissed him one last time. Even though it was a nice, tender kiss, you knew there was no spark for you. "Yes. I'm sure," you said. Dean nodded and walked toward the door. "Please don't be angry with me, Dean," you told him.
He'd had his hand on the doorknob. "I'm not angry, [Y/N]," he said without turning to look at you. Then he just left.
Left you alone to have time with your thoughts. That was a bad thing, seeing as all you could think about was that you were a terrible person. But would've sleeping with him again made you even more terrible? Especially when you regretted doing it in the first place? Especially when you thought you might be starting to like Sam... Now might just be a good time to go to sleep or something... you thought.
But you couldn't go to sleep. And you couldn't force yourself to feel the way about Dean he felt about you. You knew he wasn't a sensitive guy. That's why you were convinced the only reason he latched onto you was because he was secretly afraid of dying and he just didn't want to admit it. It was the only explanation. If Sam had been doing the trials he wouldn't have cared, he would've been focusing on his brother, and he probably would've sent you on your way by now. Because you recognized that, you couldn't bring yourself to feel a certain way towards him. You were just neutral. Willing to help, but not attached. And somehow, right now, that made you a terrible person. And you would continue to be a terrible person, at least to Dean, until he was done with the trials- whether he finished them or not.