Supernatural Imagines

Dean Imagine

Requested by salix67
Imagine: Meeting your high school crush, Dean, again and going out for a few drinks.

SLIGHT SMUT WARNING!!!SLIGHT SMUT WARNING!!!

It has been 8 years since your high school graduation. You loved high school. Sure you had tons of homework and there was so much drama, but you had people that helped you through high school.

You had two amazing best friends, but more than that, there were two special people who changed your life. Their names were Sam and Dean Winchester.

Sam was your best friend. The one who you shared all of your secrets to. Dean, on the other hand, was your major crush. You and Dean had unbelievable chemistry, and the two of you always flirted.

Sam used to tease you about yours and Dean's relationship, and he also encouraged it the most. One day, however, the Winchesters just disappeared. They didn't say goodbye and you had no idea where they went.

Now, here you are present day. You high school reunion is tonight and you weren't planning on going, but for some reason you went anyways.

You wore a beautiful dress that fit you amazingly and expressed all of your best features. Your did your hair so elegantly and your make-up was beautiful.

You wore pretty jewelry that accented your dress perfectly. When you were all finished getting ready, you looked gorgeous.

You entered the room that your high school reunion was located at and all eyes were on you. You Daly confident that you looked good and you talked to so many people that you didn't even recognize.

You were just walking around the room, when you saw a familiar face. "Sammy?" you asked. Sam turned around and saw you.

"Y/N?" he asked. "Hey!" you said with a smile as Sam came over and hugged you. "How are you?" Sam asked. "I'm great, and how are you?" you asked.

"I'm doing good. Do you wanna see Dean? I'm sure the two of you have a lot of catching up to do," Sam stated. You nodded your head and Sam led you to Dean.

He was at a table talking to a bunch of girls. He looked hotter than you could ever imagine. He was by far the cutest man you had seen. "You're drooling," Sam whispered in your ear.

You glared at him and said, "Shut up, Sammy." Sam let out a chuckle and then led you over to the table where Dean was.

Dean was telling the girls there some funny story when Sam interrupted him by clearing his throat. Dean was two focused on the story to pay attention to Sam though, so he just kept talking.

"Damn Winchester, I don't even get a hello?" you asked. The sound of your voice made Dean stop immediately. "Y/N?" he asked as he turned around to face you.

His mouth dropped at the sight of you and he stood up and have you a hug. "I've missed you," Dean told you. "I've missed you too," you replied.

Dean pulled you off to a solitary table blowing off everyone else. "You look great!" Dean admitted. "Thanks you look pretty good yourself," you replied.

Dean laughed but you swore you saw him blush a little bit. The two of you chatted for a few hours at least. It wasn't until you noticed that half of the people that had been there before had left that you realized how long you and Dean had been talking.

"I think they're closing this place soon," you said. "Yeah, we should probably get going," Dean replied. You nodded you head a little bit sad because you didn't want to stop talking to Dean.

You stood up and Dean walked you to the door of the room. You were waiting for Dean to say something, but he didn't, so you said, "Goodnight Dean."

Dean gave you a small smile and you were about to leave when Dean said, "Do you wanna get some drinks?" You turned to face him and he continued, "There is a bar down the street and I was just wondering, I mean if you want to, would you like to go out to the bar with me, tonight?"

You smiled and said, "I'd love to." Dean smiled back and led you to the Impala. "I've always loved this car," you said. "I've always loved...uh...Baby too," Dean responded.

You smiled and looked at Dean as he opened the car door for you. You slipped in and Dean shut the door before coming into the car as well.

Dean got into the car shortly later and drove to the bar, which wasn't that far. Dean was very chivalrous as he opened every door for you.

"So, is your plan to get me drunk tonight, Dean?" you asked. "Of course not Y/N, no more than three drinks, that way we have a buzz," Dean said. "Three strong drinks or three nonalcoholic?" you asked out of curiosity.

"Three strong drinks, definitely," Dean replied making me chuckle. He ordered the first drinks and the two of you continued to talk.

By the time the two of you were on your third drinks, you had a bit of a buzz, because Dean had ordered the strongest drink in the bar.

"So, I want to know why you invited me for drinks tonight," you told Dean, slightly drunk. "Isn't it obvious?" Dean asked. "No," you replied.

"Y/N, I've been in love with you since the 10th grade, didn't you know that?" Dean asked. You looked shocked and replied, "No, but I've been in love with you since the 10th grade. I didn't know that you loved me back."

"Wait, you loved me? And I loved you. So, why aren't we together?" Dean asked. You thought about for a moment and replied, "I don't know."

Dean smiled at you and said, "Come with me." "Where are we going?" you questioned. Dean winked at you, but he didn't say a word. Instead, you both got in the Impala and Dean drove somewhere.

You trusted Dean, and soon you arrived at a place. "Dean, are you going to tell me where we are now?" you asked. "We're at the Bunker. The place where I live," Dean replied.

Dean led you to the front door and into the massive house. He found his bedroom and led you into it, shutting the door behind you. "Why are we here?" you asked.

"Because you and I belong together, and I'm tired of being apart from each other," Dean told you. You smiled and Dean pulled you into a long, sweet, passionate kiss.

You both smiled into the kids because it felt so right. Dean laid you on his bed and continued to kiss you. He began unzipping you dress while you took of his shirt.

Once your dress was off he roamed his hands up and down your body, and soon your clothes and Dean's clothes were off. You smiled as Dean continued to pleasure you, and you in turn pleasured him.

Usually, you wouldn't have a one night stand with a random guy. But this wasn't a random guy, it was the love of your life. And this wasn't a one night stand, it was the beginning of forever.

Hello my little monsters!

Sorry this one was a bit longer than the others. I hope y'all liked it though! I liked writing this one. Thanks to all of you for reading. I love you all and all of you are amazing!

Always Keep Fighting!

~Caela~