Supernatural Fan Fiction ❯ Supernatural Imagines ❯ Midnight Confessions (18+) ( Chapter 1 )

Pairing: Dean x fem!reader

Genre: Fluff, Smut

Characters: Dean, Y/N

Dean Winchester has been your friend for as long as you can remember. He was your first partner on a case and you both just clicked. You were able to tell him anything and you knew that he wouldn’t judge you; you trusted him with your life. 

Yours and Dean’s friendship was a rather unusual one. You both liked to cuddle one another, especially when the other is going through a hard time. When one begins to scream and shout, the other runs to their side and grabs them in their arms. 

Also, however, over the past few years, feelings has begun to develop between the two of you, but neither have ever admitted it. The sexual tension was becoming unbearable and you couldn’t keep your feelings a secret from him any longer. 

You grabbed a bottle of whiskey and two glasses before walking towards the bunker library where Dean was located, researching for another case. You placed a glass beside the book Dean was reading and poured the whiskey. Dean looked at you and raised an eyebrow inquisitively. “What’s this for?”

You finished pouring into Dean’s glass and began pouring it into yours. “There’s something I have to tell you, and I think I’m going to have to have a few drinks before I can.” Dean furrowed his eyebrows before picking up his glass and taking a swig of the whiskey, hissing as the burning liquid fell down his throat.

“Oookay. Not worrying at all.” You stifled a laugh before sitting down across from Dean. “Don’t worry, D. It’s nothing to worry about, I don’t think.” He pulled a bitch face. “That’s really not helping.” You giggled at Dean’s expression and downed your whiskey, grabbing the bottle to fill your glass back up.

A few hours and two bottles of whiskey later, the anxiety of telling Dean was completely gone and left you with a burning confidence. Laughter filled the room as you stood up on the table and began to dance to imaginary music. Dean began to clap as your moves became more sexual and erratic. He could feel the bulge in his pants growing, but he was trying his best not to pay attention to it.

Dean had loved you for as long as he could remember but he didn’t ever want to tell you in fear of ruining your friendship and losing you. But he was finding it increasingly hard to hide his feelings for you as you carried on your sexual moves in front of him.

His eyes opened wide, however, when your foot slipped on the table and you landed right in his lap. A loud giggle escaped your lips at your current predicament as you looked up at Dean. You immediately got lost in his green eyes, staring straight into them. 

Dean stared straight back down into yours, his breathing becoming increasingly uneven. A few moments later, the gap between the two of you closed as your mouths attacked each other. 

You maneuvered yourself to straddle Dean’s lap, wrapping your hands around his neck. His hands landed on your hips, kneading your closed skin. A battle of teeth and tongues commenced in a hot, sweaty fight for dominance. Dean’s hands travelled underneath your pants and squeezed your ass, causing you to gasp. 

Dean took his chance and began attacking your mouth. Your hands travelled up his neck to his hair and pulled, causing a low groan to emit from him. Wetness began to pool in your underwear as Dean began to explore your body, his fingers delicately tracing every inch of your skin. 

“Dean. Need you now.” You heaved yourself off Dean in a hurry to unbutton your pants and pull them off, your underwear following suit. Dean followed your lead and unzipped his jeans, palming himself through his underwear. He slid his jeans down slightly and his member sprung up, bouncing against his stomach.

Your mouth watered at the size of him. Dean reached forward and gently pulled you towards him. He palmed himself a couple more times before you gently straddled him, allowing your walls to stretch to his size. 

You hissed as his member fully entered you and waited a few seconds before moving. Slowly, you began to move up and down, his member completely filling you up. He began to move in rhythm with you, his dick hitting your g-spot every time. 

Once again, your mouths attached themselves to each other as your hands wandered each others bodies. You could feel a familiar feeling building up inside your stomach as Dean pounded up into you. “I’m nearly there, Dean.” He leant forward to touch his forehead with yours, sweat completely dripping from the both of you. 

“Wait for me, sweetheart. I’m so close.” A few more thrusts into you and you both fell apart together, pleasurable moans falling from both of your mouths. You fell onto Dean’s chest in exhaustion as he kissed the top of your head.

“I love you, Y/N. I have done from the first time I lay eyes on you. I just want to tell you in case you didn’t feel the same way. But, now I know.” You looked up at Dean and gave him a warm smile before placing a gentle kiss on his lips., confirming your feelings for him. “I love you to, Dean Winchester.”

He carefully pulled out of you before grabbing a blanket from the side of you and wrapping it around you both. Dean kissed the top of your head and wrapped his arms around you, enjoying the warmth of your body.

“I will always love you, Y/N.”