Supernatural Imagines: Book Two

Remember That Night? (d.w)

Pairing: Dean Winchester x Female!Reader (past), OMC x Female!Reader (main)

Word Count: ~3.6k

Warnings: angst, heartbreak, falling into heartbreak after healing

Summary: After a whirlwind romance with Dean Winchester, you experience the worst heartbreak when he leaves you. You never thought you'd be able to move on until you finally do. Then one day, after not thinking about Dean once, he messages you, and it brings your entire world crumbling down.

Author's Note: I wanted to write a story in the POV of a woman who was one of Dean's flings. One who fell hard for him before he upped and left because hunting needed him more.

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The day after you said goodbye

All I did was lay in bed and cry

Never have you ever experienced heartbreak quite like this one. Dean Winchester left a lasting effect on your body and mind. You two weren't together for long, maybe a couple of months, but you fell hard and fast for him. He made it so damn easy to love him.

Dean, when he wants to be, is charming and loving and the perfect gentleman. When he was able to, he'd bring you flowers every time he visited you. When you were together, he made sure to always put you first. When he left, he made promises that he didn't know he'd be able to keep.

He kept coming back. Sometimes with life-threatening wounds. Sometimes with pure exhaustion.

However, he always came back. The breaks lasted anywhere from one to seven days. You never knew what he did, who he was doing it with, or if he was being safe. Whenever you asked him about the wounds he had, he'd play it off as being clumsy or that he and his brother got into a fight.

You never questioned it because you figured he'd tell you when he was ready.

Now... Now you're broken into a million little pieces that only Dean can put back together. He left, for good this time. What he left behind is a woman with a broken heart and a shattered soul.

You haven't left your bed since he said goodbye, and you must have cried enough tears to fill up two bathtubs. Your older sister, Karlie, sits on the edge of your bed with a box of tissues in one hand and the other on your back.

"I'm not going to pretend to know what you felt for him, but this isn't the end of the world, Y/N..."

"Why did he leave me?" you cry into your pillow. "I love him."

Karlie has had her fair share of heartbreak, but she's never seen you like this. It breaks her heart knowing she can't make it better. It's just you two after your parents died, so she feels a responsibility to look after you.

"There will be someone else, Y/N. Someone better. Someone you deserve."

"I don't want anyone else. I want Dean!"

She remembers you calling her crying when Dean left yesterday. You two had been on a romantic weekend that you were so excited about. She thought things were going well until Dean left. No goodbye, no explanation. He just dropped you off and told you it was over. That he was sorry. Karlie is pissed, and if she ever sees Dean, she's going to make him regret breaking your heart.

For right now? She needs to be there for you.

"I'm sorry," she whispers.

You bury your face in your pillow and continue to bleed tears.