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Dean thought he was generally a good guy. Not a great guy, not the next Gandhi or Einstein or whatever, but he showed up for work on time, did his homework, treated his girlfriend right. He figured when he was older, he'd pay his taxes and take good care of his kids. Basic upstanding kind of citizen, a real easy-going guy.
So it was all kinds of fucked up that he was in the janitor's closet at school, making out with the one person in the entire town of Stars Hollow that he couldn't get along with.
He could have said that he had no idea how they'd ended up there - honest, officer, it was an accident, he tripped and fell on my lips! - but he'd be lying. He knew exactly how they'd ended up kissing with a shelf of cleaning supplies pressing into his back. He'd run into Jess in an empty hallway, Jess had made some wiseass crack about Rory. Dean had told him to stay away from his girlfriend (though half the time it seemed like she didn't think she was, anymore, God, what did he have to do to keep her?), and Jess had said, "Make me." And Dean was generally a good guy, but he was fucking sick and tired of Jess, and the way Jess was always, always challenging him somehow, trying to take away his girlfriend and his peace of mind. So this time Dean snapped, and since Jess wasn't exactly huge and Dean was well over six feet tall, he slammed Jess into the lockers without too much trouble. Then he was just standing there, looming over Jess with a red haze obscuring his vision, his hands on Jess' arms, staring him right in the eye. And Jess lunged up and Dean lunged down, and their mouths met in the middle.
The thing was, Dean loved Rory. Loved her a lot. She was the most important thing to him in the world, besides his family. But when he kissed her, it meant hello or goodbye, see you later, just reminding you that I still love you. Kissing Rory had never felt like this, like he needed to keep kissing Jess more than he needed to breathe, like all the air in the world had turned to water and Jess' mouth was the only viable source of oxygen left.
If that had been it, if Dean had had that one soul-sucking kiss with Jess and run, then maybe it could have turned out okay. Well, not okay, but it wasn't like he had a burning desire to be able to look Jess in the eye afterwards, unlike that one time with Beth's older brother Ben, which had pretty much single-handedly led to his "let's just be friends" split with her. Dean could have handled a long-distance relationship, but not the possibility that Ben might pick up the phone when he called her.
So, kissing Jess against the lockers could have ended, not well, but at least in an awkward, half-verbalized agreement never to speak of it again rather than disaster. But Dean hadn't jerked back and run, hadn't tried to beat Jess up for the insult to his masculinity, hadn't even backed up and blundered his way through an explanation that he didn't like Jess that way (or at all). Instead, he'd pinned Jess even more securely with a thigh between his legs and buried one of the hands he no longer needed to hold the other boy still in his hair, and let Jess reach up under his shirt to claw at his back.
All of which was bad enough. But when he heard footsteps coming down the hall, which most people would take as a big flashing neon sign from heaven to get the fuck out before they cheated on their girlfriends and wound up with a big ol' sexual identity crisis, Dean still didn't stop. No, he just yanked open the janitor's closet and hauled Jess in with him. Then he had a brief glimmer of a second thought, but while he was standing there frozen with the realization that he had just pretty much irrevocably fucked up his relationship with Rory, Jess pushed him back into the shelf the janitor stored bleach and Windex on, and attacked his mouth again. 'Attacked' was pretty much the only word for it - Jess kissed like some kind of savage animal, with lots of teeth and spit.
Rory had accidentally bitten his tongue once. She'd apologized profusely and spent twenty minutes rushing around bringing him ice, tepid chocolate, and marshmallows. Jess just grinned around his yelp of protest and moved down to start chewing up his neck. At that point Dean gave up thinking, especially about Rory, and pulled up whatever death metal T-shirt Jess was wearing until he could get a hand down the waistband of his jeans.
They had to use cleaning rags to wipe themselves off, in the end. Dean straightened his T-shirt and fastened his jeans, ignoring Jess while he did the same. "I still want you to stay away from Rory," Dean blurted out suddenly, as Jess made to open the door.
Jess turned and smirked at him. "I'd still like to see you make me, nancy-boy," he retorted, and took off down the hall, letting the door bang shut behind him. Dean waited a decent interval, waited a little longer, and then walked out of the closet and headed home, feeling sick.
He still loved Rory. This didn't - couldn't - change anything. The guilt eating at his insides just proved that, right?
He called her fourteen times that afternoon. She never called back.