Dean was not a stranger to drinking. Blacking out, waking up in strange places....it happens. He also wasn't a stranger to being drugged, kidnapped, or knocked out. Still if he said he wasn't more than a little surprised about waking up in a paper dress, he'd be lying. In fact, the mixture of bright lights and cold metal on his ass almost caused him to fall off the gurney he found himself on.
After managing to get to his feet he took in his surroundings, which led him to believe he'd somehow ended up on the set of SAW 12. Taking in the presence of the old medical equipment he quickly lifted up the flimsy hospital gown to inspect himself. Nope, kidneys still there...gotta be thankful for the little things. Last thing he remember Sam and him were recovering from a nasty run in with a vamp, now he was in Silent Hill. And where the hell was Sam?
He perked up hearing somebody in the hallway and quickly ran for the door without even bothering to check the locker. If there were other people here who might have answers, or were as lost as he was, they were first priority. "Hello? Anybody here?" he poked his head out of the room, confident that his pretty little dress covered up his shame well enough as long as he didn't turn around or do jumping jacks.