It had been months since he had made his deal and they exchanged their first kiss. It wasn't emotional. Strictly business. Yet Crowley couldn't keep it out of his mind. The smell of cheap liquor on the hunters breath. The way his unshaven face scratched ever so slightly at he jerked his mouth away from his own. The look of fear in his eyes. Crowley knew it was stupid to think of the man this way. He should be nothing to him. Just another soul on its way to Hell. Still, it didn't stop him from popping in on the old man from time to time. He would appear by a window on a rainy day when the hunter was in his study and share a drink or perch himself atop a car Bobby was busying himself with when there was no hunt to fill his time. He could sit and watch the man for hours. Watching his skilled hands pull apart a motor and gingerly flip pages of books older then himself. Watch as he carefully poured himself a glass of rotgut and Crowley a glass of Craig that was never on short supply at the Singer house. He thought of the way his face pursed up at whenever he and Crowley began to disagree on a politician or the history of a god and Crowley would have to hide a smirk behind his glass. Sometimes he swore even saw a glimmer of happiness when he showed up at the hunters house.
Crowley had been watching Bobby Singer for a while now. Sometimes Bobby knew he was there but for the most part he left his presence unknown. He knew that if the old hunter had ever found him sneaking around his house at night he would has his ass caught in a devils trap before he could blink. He knew where all of the traps were and made damn sure he stayed away from them. Especially the one in Bobby's bedroom. The last thing he wanted to do was explain to Bobby why he was appearing at the end of his bed in the middle of the night.
He had almost been caught once. Just once. The boys had just finished a hunt and the roads were beginning to ice over with the sleet that had started to fall earlier that evening. Dean wasn't about to risk the life of his brother or the Impala on the icy roads and they would both pick Bobby's over a cheap motel room any night. The old house was cold in the winter and heat didn't make it to every room. Bobby sacrificed his bed to Dean while Sam and himself stayed in the den and busied themselves with research on cursed objects.
Crowley didn't mean to bump against the nightstand, sending the small lamp crashing to the floor. Dean shot straight up in bed grabbing in the dark for his gun. Crowley simply muttered a curse and disappeared into the darkness once more.