Supernatural imagines and preferences

~First Kisses~

•Dean•

It was yours and Deans third date and you knew what that meant in every mans mind.

Sex.

That terrified you and you knew he noticed you acting funny the whole night. You both sat at a booth at a very cute diner where he said he used to always take Sammy to when they were little.
The wallpaper was old and chipping off, the counter was not new as well yet you loved the feel of it just the same.
Dean had finished his meal and it was almost time to go, you had barely touched your food afraid you might end up knocking it everywhere from your shakiness.

"Y/N, are you alright?" He asked leaning over slightly.
'I'm such a baby! Look at me ruining his night like this!' You thought angrily to yourself making tears swell up in your eyes yet you quickly blinked them away hoping Dean didn't notice.

"Y-Yes I'm fine" You stuttered and as Dean threw a few bills on the table you stood up with him and walked out, side by side.
Deans hand reached out and grabbed yours, you panicked for a moment yet eased at his gentle touch.

When you both arrived outside the impala Dean stopped and let go of your hand.
"Tell me what's going on" He asked and moved you gently with his hands so you could both face each other.

The beat of your heart was so intense it pounded against the walls of your ribs like a caged prisoner begging to be released as your head shakily bowed, keeping your eyes focused on the rippling puddle beside Deans foot.

A sneaky little tear droplet dripped off your face and into the puddle making a tiny little 'splish' noise.
"Darling," He breathed and pulled you into a tight embrace. "you look terrified, what's going on?" He caressed the back of your head and traced circles with his thumb on your back.

"I'm s-sorry, I k-know what third dates m-mean but I just ca-can't" You stuttered and you hated every word coming out of your mouth making you cry harder.

Dean pulled back and held you as you both stared into each others eyes.
"Third dates-" He looked very puzzled for a moment but then a look of realisation came over his face.
"Oh sweetheart we weren't going to do anything if you weren't ready!" He exclaimed with a comforting smile. "don't cry, it's okay, you don't have to be scared" He breathed and wiped away your tears with his thumb as you felt his face getting closer.

Soon enough you were pressed against the side of the impala and Deans lips connected with yours. Both your mouths moving in perfect sync, dancing to a silent song. It was short yet loving, playful but intense; and in every way it was perfect.

After a while, he drove you back home and he went to the bunker. While you both laid in your separate beds you thought of each other and dreamt of how perfect it would be when you would spend the night together for the first time.
•••
•Sam•

It was a gloomy day outside yet on the inside of the bunker it was happy. Even if it was dead silent with Deans faded out rock music coming from his room it was peaceful. No angels except Cas who was out doing whatever, no demons, no monsters, no hunting. Just for one day and you loved it.

Although everything was peaceful your mind was spinning, going crazy over one person and it just happened to be the tall moose man.
You and Sam have been throwing hints at each other for months but you both being nervous wrecks when it comes to these types of things, you weren't getting anywhere.

With a boost of confidence that had mostly to do with boredom you went looking for Sam, planning on pouring everything out to him, expressing your feelings.