Dean had gotten used to your appearances by now. Like Cas, as an angel, you appeared out of nowhere and disappeared when you so wished. You appeared less though, so Dean treasured every moment he had with you, but it also meant you knew so much less than Castiel did, which meant you were so much more impressionable.

You'd appeared at an arguably bad time, where Dean was ushering some chick out of his room in the motel, a smug little expression on his face as he lead the woman on, coaxing her into thinking he'd see her again. (They wouldn't.)

He was shirtless, hair messy and just his boxers on—lucky that Sam was at the library doing some research. Dean glances up as he sees the woman looking at an area in the room, and he glances over, seeing you sat on the couch. His brows raise, not looking too surprised. "What? Don't judge me," he retorts instantly.

He watches the woman leave, then he glances to you again. "You're looking at me like you've never—" Dean goes quiet, hands on his hips as he looks over you. A faint smirk adorns his lips at your confused expression. "Oh, you've never had a little.." he gestured around. "That's adorable, sweetheart."

He folded his arms over his chest, considering himself for a second. You're adorable, all unassuming. Innocent. All of things Dean isn't—it makes him smirk at the thought. He could so easily change that for you, corrupt you. God, if he wasn't as good as a man he is.

Which he isn't, so of course—"You're kidding me, right? Never kissed anyone? Anything else?"