bug drool

Contest Entry #7

Title: Be My Cherry Pie?
Author: randomfandomff
Pairing: Dean x Reader – Flirting, Friendship
Word Count: 1000

Here we go again, you thought to yourself rolling your eyes at the older Winchester. He seriously thought those cheesy lines would work on you? How could anyone actually fall for that crap? It did make you smile a bit though, you had to admit. Hell, sometimes you even liked the attention he gave you, but even Dean should know when to stop.

You’d been hunting with the brothers for a few years now so you were definitely used to Dean’s antics. He’d take any chance he could get to try his stupid lines on you and pretty much anyone within shouting distance. You knew because you’d actually been a witness to him trying to do just that; oh that poor, clueless girl.

Closing the book you were reading you turned to see Dean sitting next to Sam at the table giving you his crooked half-smile, the smile that you knew damn well could make anyone melt and swoon. Thing was, you weren’t just anyone. Sure, Dean was attractive and he could be darn sweet when he set his mind to it, but after spending so much time with both brothers you didn’t think you could ever see him as more than a really good friend. 

Dean wasn’t exactly what you would call “boyfriend material”. His reputation preceded him, sexy, sly, and stubborn - a very dangerous combination. 

As a friend, though, he was everything you could ask for. He always brought your favorite junk food when out on a run, he watched re-runs of your favorite show with you when you were feeling down, and always made sure you were safe when out working a case. 

Hmm, maybe Dean isn’t such a —

“So … whaddaya say sweetheart?” he coaxed winking at you and interrupting your train of thought. 


You watched him take another bite of pie making a point of licking the cherry-red filling off the spoon ever so slowly.  “Did it take you all night to come up with that one, Dean?” Sam groaned interrupting Dean’s ploy. You turned to look at him just in time to see him roll his eyes at his big brother. Sometimes it seemed to bug Sammy more than it bugged you when Dean got like this. 

Dean turned to his brother, “Butt out, Sammy.” You saw Sam give a slight smile and shake his head knowing well that your response would be the same as the previous thousand times Dean had tried to hit on you. He knew you could definitely handle Dean, but he turned to look at you just to make sure. After giving Sam a slight nod that meant you had this covered, he obediently turned his eyes back to his computer screen, but you knew his attention was still on you both.

How many different was could Dean Winchester hear the word no before he got the message? Usually you’d just sigh and move to a different room or shoot him a look that very clearly said, hell no. This time though, you decided to have a little fun with it.

You looked down to your lap, avoiding his eyes. When you were ready, you turned to face Dean - chin down, eyes big, and without a word gave him the sweetest, most innocent smile you could muster. You stood from the couch, aware that you now had both brothers’ attention, and began making your way over to Dean in slow, steady strides, eyes firmly fixed on his. 

You felt his searing gaze on you from head to toe even as you finally stood before him. You gave yourself a mental high five for having chosen to stay in your sleeping attire. What you wouldn’t give to know exactly what these boxer shorts and practically see-through tank top were doing to his very active imagination. 

He tried to appear smug, like he knew he’d won you over. You weren’t so easily fooled, though. One look into his big, green eyes and you could tell he had no idea what the hell was happening. You reveled in it. Glancing over at Sam you almost broke character seeing his mouth gaping and eyes popping out of their sockets. He looked even more confused than his brother. This was going to be great.

Continuing your little game, slowly you kneeled gliding your hands from his knees up the length of his thighs exerting the slightest pressure, enjoying both brothers’ reactions. His eyes roamed up your torso reaching your face once more stopping on your lips as he subconsciously licked his own. Perfect

You scooped a bit of cherry filling with your middle finger from the plate on his lap and slowly licked it off, never taking your eyes off him. He was absolutely bug-eyed, mouth practically drooling and it took everything in you not to crack and fall over laughing right then and there.

Dean’s lips moved, but no real words came out, just a strangled sound that let you know you had him. You couldn’t believe it. Dean friggin’ Winchester, all-around playboy and master of seduction was actually speechless. You couldn’t contain a proud smile that escaped your lips. You knew you wouldn’t be able to keep up the ruse much longer so you decided to finally let him have it. 

You stood once more and prepared to go in for the kill. Hands on his thighs, you leaned over his face your gaze piercing his and hearing his breathing hitch, leaning closer and closer until …


“Damn it, Y/N!” he growled getting up from his chair. You couldn’t contain your laughter any longer and Sam finally understanding what had happened and breathed a huge sigh of relief and let out a hearty chuckle as well. Dean threw his plate onto the table in front of Sam and stomped to his room. Once you could finally stop laughing you yelled after him, “That’ll show ya, Winchester!”

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