Supernatural One-Shots and Imagines (x Reader)

Road Trip (Dean x Reader - One-shot)

Credit to the Gif creator

Summary: Dean and Sam go on an impromptu road trip to a far away town and Sam thinks it's for a possible case.

Word Count: 1251

Warnings: None

A/N: This is quite different from anything I've written before. It's a Dean x reader one shot, but it's written from Sam's Perspective. I would love to know what you think, please feel free to send a message or leave a comment, feedback is always appreciated

"Tell me again, why have we driven all the way from the other end of the country, to investigate the mildly strange weather patterns around here?" Sam turned to his brother, who was currently bringing baby to a stop in the main street of town. Giving Dean a frustrated look, he continued, "Weather patterns which may or 'most likely' may not have been caused by some random demon activity?" Dean just bit the inside of his cheek as he took the keys out of the ignition and leaned back in his seat, looking a little sheepish as he gazed out the front windscreen. Sam followed his brother's gaze to the shop in front of them and read the sign, shaking his head, Sam gave a bit of a snicker feeling both equally annoyed and amused. There splashed across the storefront window, looking like it had come directly out of some 1950's advertisement was a painting of a beautiful woman wearing a red gingham apron. There in her outstretched hands was a perfect looking pie and beside her in big fancy writing was the name of the shop, 'My Oh Pie'. Just under that, came the real reason for Dean's cross-country venture, 'Voted America's Best Pies, three years running'. Sam just slowly turned his head back to Dean and rolled his eyes, "Dean! Seriously?"

With a shrug of his shoulders, Dean spoke as he made a move to get out of the car, "What? I was hungry and I thought a nice road trip would do us good."

Sitting down at a table, Sam had a perfect view of everything going on in the diner and while Dean was distracted by the menu in his hands, Sam laughed to himself as his eyes landed upon one of the staff. The beautiful woman who currently stood behind the counter was exactly Dean's type, her long (HC) hair was tied in a simple ponytail and she wore a red gingham apron like the one on the storefront, hugging her curves in all the right places. Sam just knew that as soon as Dean set his eyes upon her, he would try to work his moves and Sam looked forward to her response. He could already tell by the way she interacted with her customers that she was confident and funny and unlikely to take crap from people. This was going to be fun!

Clearing his throat, he gained his brother's attention and motioned towards the counter. Dean raised his eyebrows and smirked, "Mmmm, looks like there more than just pies on the menu."

Wiping the bench, she gazed up and moved her eyes towards them, an amused smile taking over her features, as if she had heard the words fall from Dean's lips. Looking as though he just got his hand caught in a cookie jar, he buried his head back in the menu, pretending to look busy, as Sam watched on amused. Grapping a pad and pen out of her apron pocket, she threw the cloth aside and made her way over, coming to a stop in front of them. Taking a little breath, she gave them both a quick glance over, her eyes settling on Dean before giving him a breathtaking smile, Dean swallowing thickly as a result, the action didn't go unnoticed by Sam.

"Good morning boys, I haven't seen you two here before, did you make a special trip for the pies or are you just passing through? She may have been talking to them both, but she only had eyes for Dean, his usual confidence and swagger faltering at her extra attention, Sam leaning back in his chair to enjoy the show, rather surprised that his brother seemed a little intimidated.

"Ah... Yeah... Ah... not really... I love pies",

Dean could hardly get a word out as Sam watched him fumble over the words in his head, feeling just a tiny bit sorry for him, he decided to come to the rescue. After a quick glance of pity in Dean's direction, he looked at her nametag and spoke, "I think what my brother is trying to say (YN), is that we are in town for a couple of days for work, but he only took the job on because he was wanted to come here."

Turning her attention back to Dean, she gave him another beautiful smile, "Well I don't know how far you have travelled, but I hope you think it's worth the trip, are you ready to order?

Pulling himself together a little, Dean placed his order, enjoying the rear view of her as she walked away, filling his cheeks with air he slowly exhaled and looked at Sam. "My God Sammy, did you see her eyes? They're the most stunning (EC) eyes I have ever seen and those lips... hmmm, what I could do with those lips." Sam stayed silent as Dean rattled on, unsurprised that he seemed so taken by the girl, after all she was absolutely gorgeous. "And that voice, I could listen to it for hours, not to mention that she works in a PIE SHOP", Dean almost sang those last two words and Sam couldn't help but laugh.

"Why didn't you ask out? If it was any other girl you would have done it already."

Dean cleared his throat and gave a bit of an agitated snort, "Don't worry Sammy, by the end of the night, she'll be coming out for a drink with me, just give me a chance."

If only that had been true, Sam sat there and watched his brother devour pie after pie, making him wonder whether they really were the best pies in America or whether he just wanted an excuse to keep calling her over. In either case, he would see Dean pluck up just enough courage to ask her out, only to have her go and do something that had him acting like a shy and speechless schoolboy again. It really was quite funny to watch, but by the end of first breakfast and second breakfast and elevenses, (YN) was the one to ask him out.

"You boys look like you could do with a decent home cooked meal," looking straight into Dean's eyes with a smile, (YN) continued, "I know they're good, but you can't live off pies alone." Dean's expression said otherwise, yet he didn't open his mouth to speak. "Every Friday, we have a staff dinner here after we close, why don't you join us?

Dean's face lit up as he looked at Sam with a smug smile. Finally, finding some confidence, he spoke, "I'd love to come, but won't your boss mind you asking two random strangers to your staff dinner?"

"Yes, if any of my staff asked random strangers here for dinner, I probably would get a little upset, but seeing as though I'm the boss, I can do what I want." Before walking off she gave them a warm smile, "Be back here at six and stay for dinner," then she turned on her heels to walk away, stopping after just couple of steps, then looking back over her shoulder she gave them a wink, "I can cook more than just pies you know!"

As she walked away, Sam watched his brother's expression wash over with pure wonder, his mouth hanging open and his eyes filled with light, slowly he closed his mouth and turned to look at him, "She's perfect, Sammy, I think I could be in love."

I would love to know what you think, please feel free to send a message or leave a comment, feedback is always appreciated