Your First Kiss:
Dean: You both sit on the Impala, drinking beer and laughing. Suddenly he stops and stares at you intently.
"Have I ever told you how hot you are?" He whispers in your ear. You shiver at how close he is and manage a giggle. As he hears your soft giggle he grabs your chin and turns your face and plants a long and rough kiss. You are both left panting after you two part. His eyes twinkle and he lets out a low chuckle and returns his attention to his beer. It will be many weeks before he mentions that kiss to you again and asks you out.
Sam: It's the end of your first date, and it's that dreaded moment, to kiss or not to kiss? You are both chatting and laughing, when you reach the door to your complex. He shuffles his feet awkwardly and after what seems like hours he makes up his mind and dips his head down to catch your lips in a slow, burning kiss. When you part he asks if he can see you again, your obvious answer is yes.
Castiel: You've both been hanging out alone a lot when suddenly he cocks his head to the side and asks, "Are we dating Y/N?" Your eyes widen and you cough. "I got the impression when two people hang out alone a lot, they are considered to be 'Dating'" You still aren't sure how to respond and finally Cas makes up his mind and leans in to kiss you. His lips are soft, and it's obvious he's nervous but after a few seconds he catches on and you are both left breathless afterwards. The pizza man taught him well.
A/N: If you have any requests for these 'Group Imagines' feel free to tell me!