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It had been about three hours since the incident in the Diner, during which time they had been driving solidly, Dean alternating from Led Zeppelin to Motorhead when the cassette ran out. At this point the too loud music was the only thing keeping him awake, the effects of the caffeine having worn off. The resounding bass of Motorhead stopping him from drifting off.
They had not really talked much for the last few hours, though that may partly have been due to the loud music drowning out anything that either of them said. Dean was sure that he was going to have to stop for a coffee soon, as he tried to discretely stifle a yawn. Sam had been on his laptop pretty much since the Diner, so it was unlikely he would notice that Dean was a bit tired.