From: twtomboy.tumblr.com/
Dean: Dean loves to go fast with everything, including his kisses. He would always grab your waist pulling you close to him, and start attacking your mouth. Then Dean would start pulling your hair a little and try to put his hand up your shirt. You would pull away telling him that you shouldn't do what you were about to do in front of Sam and Cas. "Oh no, by all means. Don't stop cause of us," Sam said sarcastically. "You heard him, Y/N. Lets finish what we started," Dean said. "Oh god," Sam said as you and Dean went back to making out. He grabbed Castiel by the arm and they left the motel while you and Dean got 'busy'.
Sam: He's the more romantic type of guy. Sam would just kiss up your arm and neck sometimes. Other times he would softly hold you by the waist and nibble on your ear just to hear you laugh. "I love you so much, honey," Sam says staring lovingly in your eyes. "I love you too, Sammy," you reply kissing him on the cheek. He laughs in response and goes back to kissing your lips.
Castiel: Cas doesn't know what to do sometimes when he wants to kiss you. He could be a little shy sometimes and didn't know how to bring it up. Most times Cas would just usually kiss one of your hands, but this time he didn't know what to do at all. He walked up to you, looked you in the eyes and didn't say anything. "What is it, Cas," you asked him when you couldn't stand the silence anymore. "I would love to kiss you," he said cocking his head to the side. "But?" "But I'm not sure how to this time." You sigh. "Come here, Cas," you laughed taking his hands in yours. But then you let go and put your hands on his face while finally starting to kiss Cas. It was a small kiss at first, but then Cas opened his mouth a bit more and put his tongue in your mouth. The kiss was still slow, but very enjoyable. You two finally broke apart and smiled. "Wow," you breathed, "that felt like-" "Heaven," Castiel finished for you. "Yes. Like heaven." You kissed Cas on the cheek and hugged him.
