Supernatural Imagines

Dean Imagine [1]

Requested by: salix67
Imagine: Dean finds out that you have never been on a date, never been kissed, and are a virgin, and he wants to be your first everything.

You have been living with the Winchesters in the bunker for one year now. You loved the Winchesters, they were your family. But, it was also hard living with them, especially Dean.

After all, Dean and Sam were two fine and sexy men who always made jokes and played around with you. And you, on the other hand, are a gorgeous girl who is a bit shy and has never been kissed or anything else that has to do with relationships.

You see, in middle school and high school, you weren't as outgoing as some of the other kids. So, you never had a first kiss, or a first date. And Sam and Dean never knew that about you, and you were kind of thankful for that, but at the same time it made it so much harder to live with them.

One day, you were sitting in the library of the Bunker, one of your favorite places, when Dean and Sam came in. They were holding one of your oh so treasured items -- your journal.

You gasped as you watched as Sam and Dean sat down next to you. "So, we kind of found this and read it," Dean said staring at you.

You completely froze. This was definitely the most embarrassing thing that has happened to you. Luckily, you never wrote anything about having a major crush on Dean, but, still. Right now, all of your secrets were exposed, and you knew that was going to turn out bad.

"We had no idea that you weren't experienced in...dating," Sam stated. "I am experienced," you said, hoping Dean and Sam wouldn't catch you in your lie, but of course they did.

Dean opened up your journal to a specific page and said, "It says here that you have never been on a date, never been kissed, and you are a virgin still." Your cheeks heated up to a bright red color. "I-um-you know Dean and Sam, you shouldn't read people's journals," you stated, embarrassed and in shock that this was actually happening.

"I'm sorry Y/N, we didn't think it would embarrass you this much," Sam said. You felt your cheeks only grow hotter. "It doesn't," you said snatching your journal from Dean, "I will just be in my room." You quickly ran up the stairs and into your room before shutting the door. This was definitely the most embarrassing thing that has ever happened to you.

Dean and Sam looked at the spot where you were only moments ago before making eye contact with each other. "Well, that went well," Sam said. "We should've never read her journal, I feel bad now," Dean told Sam. Dean stared at the floor seeming to be in deep thought.

"What's up with you?" Sam asked Dean, causing Dean to look at his brother. "I was just thinking," Dean stated. "About?" Sam questioned. "Y/N. You know how much I like her, ever since she started living her I've had a crush on her. I was just thinking maybe this would be a good time," Dean admitted.

Sam thought about it for a moment and said, "You're right Dean. Listen, I'm going on a hunt with Bobby in a couple of days, which means you will have the bunker to yourselves." Deans' eyes lit up with happiness.

"Really?" Dean asked, to which Sam nodded his head. Dean smiled to himself as he thought of you and the day that couldn't come sooner. The next two days dragged on as Dean waited in excitement to have some alone time with you.

Meanwhile, you didn't want it to be awkward around the boys, but you were still pretty embarrassed about the whole journal fiasco.

The day that Sam was leaving for a hunt finally arrived. You and Dean both said your good-byes to Sam, and then Dean made his way to the kitchen, and you made your way to the library. You were only in the library for about thirty minutes when Dean came in. "Hey," he said with a smile.

You looked at him, and, with a smile, replied, "Hello." "How are you?" Dean asked. "Good, and you?" you asked as you got up to go get another book off of the shelf. "Good,"Dean replied walking closer to you until he was right next to you.

You looked up at the shelf and found the book that you were looking for. You stepped on your tip-pi-toes, and reached for the book. You managed to knock it off the shelf, but you didn't catch it in time, and it fell to the ground.

You reached down to get it, but at the same time, Dean reached down to pick it up for you. You looked up at Dean, just as he looked at you, and his green eyes pierced into your E/C ones. Your heart skipped a beat, and you and Dean both slowly stood up, not breaking eye contact.

You both reached full standing positions, and after only a couple of seconds, Dean slowly leaned in and placed a kiss on your lips. You were shocked, but you eventually caught on and began to kiss Dean back.

It was a sweet and slow kiss, but both you and Dean had been waiting too long for it, and you both wanted more. Dean tilted your head slightly to deepen the kiss. Then Dean pushed you into the bookcase behind you.

You continued to kiss Dean, and he broke the connection between yours and his lips and trailed his lips down to your neck. His hands rested on your lower waste, and you let out a slight moan. Dean connected his lips with yours one more time.

He then slid his hands even further down your body. You broke the kiss and said, "Wait, Dean." Dean looked into your eyes and you said, "It's too much, too fast. I'm sorry." Dean let out a small sigh, and you looked down, embarrassed that you couldn't go through with it.

Dean lifted your chin up with one finger and said, "Hey, it's okay. It isn't about sex, if you want to take it slow, then that's completely fine. I just want to make you happy." You smiled softly and placed another soft kiss on Dean's lips.

"Thank you, Dean," you told him. He nodded his head and told you, "Do you want to go downstairs and watch some TV?" You nodded your head and Dean held your hand and led you downstairs. He sat down on the couch, and turned on the TV, and you sat down next to him.

You cuddled into his side and he wrapped his arms around you, and the two of you stayed like that for the rest of the day and night.

Have I lost my touch in writing imagines? Let me know in comments! Thank you all for reading! I love you all and all of you are amazing!

Always Keep Fighting!

Caela