Dean:
You had just laid down to take a nap, when your handsome boyfriend walked in. You kept your eyes closed, even as he rested his head against your leg. The stubble on his chin tickling your skin. You were about to speak as he started talking. "Baby, I know your asleep but I love you so much. We may fight or try to make each other jealous for fun, but you're the only girl for me. You're absolutely perfect in my eyes." He sighed as he finished, kissing your head in the process of getting up. After he left the room, you had to fight the tears welling up in your eyes.
Sam:
The night before couldn't have gone better, you and the Winchesters had finished the hunt without a hitch. You even had a great night of sleep. Which is probably why you were awake so early. But being a free day you opted to snuggle into Sam's side, content in the warmth he brought you. Oh how warm he is you thought to yourself. But soon your thoughts were stirred away when Sam shuffled around, showing he had woken up. He softly petted your hair. You smiled with your eyes closed. You heard him chuckle. "I love your smile. It's something I live to see. It's beautiful just like you are, Princess."
Castiel:
It wasn't like Cas to show affection much. To be honest he hardly showed it around anyone. You were in your room laying down thinking about this. You knew he loved you, maybe he was just shy to show it around anyone. Welp, I guess that's what I get for dating an angel, you thought to yourself. You closed yours eyes to envision the times he was affectionate. Like when you were alone in the library or on movie nights (so he could learn more about human interactions). Your thoughts were torn away when you heard the beautiful, yet soft stirring of wings. Curios of what he would do, you left your eyes closed. Feigning sleep, you guess. Slowly, he leaned down and kissed your head. Before leaving, he uttered a soft 'I love you'. It was the sweetest thing you could have imagined.
Gabriel:
Now everyone knows that Gabriel could be a bit handsy. But he truly had his sweet, tender moments. You had your head laid across his lap. You had fallen into a bit of a light sleep. Still aware of your surroundings, but truly relaxed to a high degree. You twitched when you felt fingers softly tracing your face. "You really are quite stunning. I hate when you fall asleep during movie nights though, Cupcake. But I love you so I forgive you. For so long I searched for things that made me happy. Hookers, Sweets, anything like that. But I realize now, you're all I truly need by my side."
***Couldn't think of anything for Mark. Sorry!***