Supernatural Imagines

Never Have I Ever (Dean)

As Sam was out doing research you and Dean, your best friend, were at the motel sitting there doing nothing. Dean was on Sam's laptop probably doing something he wasn't suppose to do which was most likely porn, and you spent your time laying on the bed inserting quarters into the magic fingers while you watched TV. 

"I'm bored." You complained looking over to Dean who peered up at you with a glare. You had said those same exact words about ten times already in the past 30 minutes and Dean was getting irritated with it. "Can we please do something?" 

"Like what, we're stuck in here till Sam gets back." Dean sighed. 

You smirked and reached under the bed and pulled out two bottles of whiskey. "How about a drinking game?" 

Dean stood up eyeing the whiskey in your hands. It was his favorite kind, and knew he had a weakness for it. "Where did you get that?" He asked. 

"I bought it last time I was out for an occasion just like this." You walked over to Dean and sat down across from him at the small table. As you put the whiskey down, Dean grabbed two plastic cups from the bathroom and placed them down too. "So what kind of drinking game?" You said as you poured a shot of whiskey into each cup. 

"How about... never have I ever." He said sniffing his drink. 

"Oooo," You said. "Okay, me first, never have I ever had a threesome." You smirked as you watched Dean swig it down, and you poured him the next one. 

"How did you know?" He asked. 

"You're serious?" You asked. "We've been traveling together for two years now." Even though it hurt you thinking about such things because you had secretly had a crush on Dean, you just wanted things to remain the same.

"Fair point, okay, never have I ever.... kissed a guy." You gave him a deadpanned look as you chugged your whiskey. 

"I didn't know we were asking lame questions?" 

"Fine, fine, I'll amp up my questions." 

You went back and forth asking questions, with the one bottle of whiskey running low until it was gone, and you two moved onto the next one. However, by the time you reached the second bottle you were both drunk, and your questions were getting more personal. "Never have I eve..." You slurred while you swung around your cup making some spill a bit. "Loved someone I couldn't have." Both you and Dean took your shot. 

"Wait, who was it?" He asked. 

You averted your gaze. "Your question." You said pouring you both new shots. 

Looking up you saw Dean's gaze was piercing into your eyes. "Never have I ever kissed my best friend." He said leaning across the table his lips brushing against yours. Both of you shut your eyes, and after a few seconds when you didn't back away he finally pressed his lips against yours. 

It was like your lips melted against each other, and they moved in sync perfectly. You had built this up in your mind for nearly a year now, and this moment went far beyond your expectation. Finally after what felt like hours you both pulled back. 

A smirk played across his face and it soon spread over yours. Like your minds were connected you both picked up your cups and took the shot.