Chapter Text
You slept with Dean Winchester last night. Actually, you had been sleeping with him for a while, but it was always just that – sleeping. Until last night, that is. Yesterday’s hunt had gone horribly wrong, and both of you needed comfort. So what do most people do when they’re in need of comfort? They turn to their best friend. You and Dean would often find yourselves sleeping in each other’s beds at the end of bad days, but never had it gotten farther than just holding each other and sleeping. Helping each other drive the nightmares away.
Neither you nor Dean had ever mentioned those intimate moments you shared; not before, during or after. However, this time one of you had to say something, because everything changed last night. As the two of you lay in your bed, holding each other, Dean kissed you. And you kissed back. Things progressed further from there, leading to you and Dean making love to each other for the first time.
Sex was a big deal to you. It wasn’t something you did often, and you didn’t take it lightly. But Dean was, as you had once called him, “the king of casuals”. Maybe that’s all last night was to him. It would break your heart if that were true. You didn’t know when you had fallen in love with your friend. It might have been a few months ago when the two of you started seeking comfort in each other’s arms. Or it could have been years ago when you first started hunting with the Winchesters. Either way, you couldn’t deny your feelings anymore.
When you awoke that morning, you were quick to discover that Dean had deserted your bed a few hours earlier. His side was cold and his clothes were gone. You buried your head in your hands, the worry of how last night would affect your friendship shuddered through your body. Once you got dressed after a quick shower, you headed to the bunker’s library to find Dean. It wasn’t long before you spotted him, reading through a newspaper and sipping at his coffee. You poured yourself a mug of the dark liquid before turning to him.
“Where’s Sam?” you asked, glancing around the room.
“Went out,” Dean grunted, never shifting his gaze from the newspaper. This was going to be harder than you thought.
“Dean,” you started tentatively. “Can we talk?”
Dean looked up at you and flashed a smile. You knew how fake that smile was, as it didn’t reach his eyes. He folded up the newspaper and set it down. “Sure, Y/N. What’s up?”
You couldn’t believe how nonchalant he was being, but you pressed on anyways. “Last night…what happened between us…” You mentally kicked yourself for not being able to form a proper sentence.
Dean nodded, a hint of a smile still on his lips. The same lips that had kissed every inch of your skin last night.
“That was fun, we should do it again sometime,” he said smugly. He must have seen the weary look on your face, because he raised his hands in surrender and said, “Or not! Your choice.”
You sighed deeply, trying to get past his detached attitude. You knew that there was so much more to him under the surface, but getting that part of him to open up was never easy.
“Look, I don’t want it to change our friendship, but—“
“It won’t,” Dean cut you off. “It was just a hook-up, Y/N. Don’t overthink it.”
You could feel your heart sinking. Just a hook-up. The words were like knives. You briefly thought back to last night. Dean was so caring with you last night, so gentle and attentive; the exact opposite of how he was acting right now.
“No,” you insisted, your voice like steel. “That’s not what it was. Things have been different between us for months Dean, don’t you feel it? Last night…I don’t regret it. But I’m starting to feel like you do.”
“You want to do this now?” Dean asked. You could hear the annoyance seeping through him. “Fine.”