Here, have a tiny story I wrote in an hour. It has no plot. This is my first time writing in months, and it shows. Sorry for the crap.
Dean Winchester is a Terrible Brother
(Seriously, Sam shouldn't have to put up with this.)
A casual outside observer in 1999, one who had the whole story, would say that Dean was in a transitory stage in his life. Two years out of high school, he'd held a string of odd jobs when he wasn't hunting. In the eyes of the law and a good section of the population, he was a man. To John, he was still a kid—a kid who didn't get to hunt by himself, a kid who had to be home by morning, a kid who'd still get beat down by the old man for disrespect. Dean found himself in limbo—employed and yet unemployed, mature but not free. This left him with very little to do, and a series of growing complexes about uselessness.
To Sammy, however, who was not a casual outside observer in 1999, Dean was one major pain in the ass.
This is why having Dean as a brother sucked: Dean had complete control of the car. Sam, who'd had his driver's license for four months, had only sat behind the wheel twice. Sammy had a hot date with Brenda from trig? Ooh la la, when did he want Dean to pick him up? Not too late, of course—even if baby Sammy made it past second base, Dean doubted he'd last very long.
This is also why having Dean as a brother sucked: once he found out Sam was starting for his school's soccer team, Dean came to every single match. And cheered. Loudly. Sam never did decide which was worse—the time Dean painted himself blue and gold with a huge 48 on his chest, or the time Dean started a cheer calling the Cottsburg Comets the Cottsburg Cocksuckers and got escorted from the stands.
This is also also why having Dean as a brother sucked: it seemed every girl in the junior and senior classes had a better idea of Dean's…anatomy…than Sam wanted to hear about. Including Brenda from trig.
This is also also also why having Dean as a brother sucked: when Alicia Stuben realized that Dean had no intention whatsoever of "going steady," who did she physically attack in the second-floor hallway? Three guesses, and the first two don't count.
This is also also also also why having Dean as a brother sucked: sometimes he just wouldn't show up to give Sam a ride at all. Their rented house was four miles away and to get there Sam had to pass creepy Mr. Sikes-the-pedo's house and Mrs. Kerapple's Yard of Overhanging Cacti.
This is also also also also also why having Dean as a brother sucked: most of the times he didn't pick Sam up was because he was on a job, and he was a fucking idiot who didn't know enough not to get himself creamed by a ghoul. When he and Dad came stumbling in at five-thirty in the morning, Dean's clothes were dark and stiff with blood.
This is also also also also also also why having Dean as a brother sucked: patching Dean up took all of the morning, and Sam had had an American government test that day.
This is also also also also also also also why having Dean as a brother sucked: he dared to suggest that Sammy go to class instead of staying there to make sure he was okay. Fucking idiot, remember?
This is also also also also also also also also why having Dean as a brother sucked: when he was back on his feet again, he insisted on driving Sam to school, and all of the girls thought his wounds were sexy.
God, Sam couldn't wait to graduate.