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Dean started smoking the day Sam returned from Flagstaff.
He remembers the day Sam left so vividly. It was a sunny day, bright and warm. Dean woke up and Sam was just gone . He remembers checking the bathroom, the hallways, the motel lobby, over and over again, each time his heart sinking further and further down his stomach. He remembers the moment he figured out that Sam was nowhere to be found. He remembers crying in the motel room when the panic started setting in, the quarter of a serving of spaghetti-o’s he ate last night climbing up his throat. He remembers the two days he spent afterward, in a panic, asking around if someone, anyone, has seen a tall, lanky 15-year-old with a brown mop of hair. On the third day, John showed up back from a hunt. Dean tries not to remember what happened next.
When Sam returned, it was a giant sigh of relief. John was out, again, left Dean behind in case your stupid brother comes back, and it was just Sam and Dean. He couldn't even bring himself to get angry at his baby brother, couldn't tell Sam that he thought the kid was dead, that their life of hunting has finally caught up with them. Sam looked like he lost a couple of pounds, so Dean brought him along to the convenience store to get some food to eat.
Maybe it was an impulse buy. Maybe it was a physical manifestation of relief. Maybe it was a fuck you to John. Dean is still not sure why he bought the pack of cigarettes in the convenience store that day. Dean was nineteen at the time, and if he was being honest to himself, he was a bit surprised that he has never smoked in his life prior, and not for a lack of occasion. It wasn't like Dean was a prude or anything. He drinks, he fucks, it just never occurred to him to smoke. He has had a few bar escapades after his dad made him a fake ID when he looked old enough to be 21, but he hasn’t utilized it that much except for when he goes in to hustle pool, because nobody would look after Sam if he was away for long. Most of Dean’s drinking happened after hunts with his hunting buddies, hanging out with other kids who have fathers like John. Some of those kids smoked too, but Dean never smoked with them. John has let on in passing once that he thinks smoking is disgusting, and what is Dean but an obedient soldier to his father’s expectations?
Dean bought a pack of Marlboro Red while Sam walked around the store. He cringed a little bit about how expensive the pack was, but figured that it was probably going to last him a couple of weeks. Besides, smoking curbs your appetite, so maybe in a way, he’s actually saving up money for food. He thinks of what his dad would think if he ever finds Dean smoking, but what’s a couple more bruises to hide?
That night, while Sam was asleep, Dean stepped into the motel bathroom with his Marlboros and the silver lighter he typically uses for salt and burns. He considered going outside for a bit, but ultimately decided that the bathroom will do. The bathroom was decent if a little bit shabby. The grout on the tiled floor base of the tub was darker than in other areas, but Dean was just impressed that this motel even has a bathtub at all. Dean remembered to open the vent, then sat on the edge of the tub, popped open the small red pack, and picked up one cigarette. He rolled it around with his fingers, surprised that the cigarette was lighter than he thought it would be. I could just crush this , he thought, I could just crush this with my fingers and it would crumble so easily. He figured he was right about that, but also remembered the eight dollars he spent on the pack. Maybe in other states, it would be cheaper , he thought, not questioning why he's thinking of a future where he would even need to buy more cigarettes.
Finally, he placed the cigarette in his mouth and lit it up, inhaling while he held up the fire in front of the stick. He's seen enough westerns on motel televisions to know what he's doing, except for the part where the smoke fills up his lungs and suddenly the cinematic view that he had on smoking was washed away, replaced by the need to expel the smoke out of his body. He thought about Sam outside the door possibly waking up, and immediately toned down the coughing. After a few seconds, Dean was ready again. He let the smoke pool in his mouth this time and exhaled. Dean assumed he was doing it wrong (aren't you supposed to inhale the smoke and not just essentially gargle it?), but the resulting smoke cloud was so big and pillowy that he can't help but smile. He takes another hit, this time letting the smoke sit in his mouth and then flow right down his throat. It was tingly and scratchy, but not unbearably so.
He thinks of Lee, one of his hunter friends. Lee and Dean kissed once, after a few rounds of beers during a feisty poltergeist hunt that John allowed Dean to deal with together with the older hunter. Lee was smoking that night, and his mouth tasted like Dean's did now. John would have killed them if he knew, but he didn't, and until now Dean still wonders if he subconsciously chose the Marlboro Red because it was what Lee smoked.
Dean took a few more drags until the cigarette finally ran out. He stood up, pressed the lit end of the stick onto the edge of the sink, and threw the stub into the trash can. He looked up at himself in the mirror. He suddenly felt foolish, like a loser hiding in the bathroom to smoke for the first time, which is exactly what he was doing. He felt a little stupid. Excited, too. Sam is back and I'm doing something that will piss dad off , he thinks. He doesn't know why he found delight in the second statement, but the delight was there.
Dean stepped out and turned off the lights.
It took five days for Dean to finish the pack.