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Rory was going through filing cabinets when he found it.
Dean wasn’t a very organized person, there were bills and old emails from different prostitutes, (and Rory didn’t even want to think about what was written there. Ew.) He came across a file labeled, “Dean Winchester, years 1-4.” He smiled at it that was before Mary had died. Most of the things in the file were nothing more than useful black-mail, but then he came across something, um, unusual. There was a piece of lined paper where a young boy had scribbled the words, “Ten Things I Want to Do with My Future Girlfriend.” Rory cooed at how innocent it was, before stuffing it under the mattress. Dean’s birthday was less than a month away, and he had just had the perfect idea for what to do for it.
On January 24th, Dean woke up to a teddy bear palace, and his fiancé still fast asleep next to him. The younger boy was obviously the cause of the five million teddy bears surrounding the room, he was knocked out like a light. The poor thing probably had to get up way early to arrange this. Dean quietly shook him awake, and Rory responded with a grunt.
“Babe, what is all this?” Dean asked. Rory turned around to face the ceiling, and looked around, as if he had somehow forgotten the two million teddy bears surrounding the room. He perched himself on his elbows and turned to face Dean.
“It’s your birthday.” He said, as if that was obvious. In case there was any wonder, Dean was not a big fan of teddy bears, or himself, or birthdays, for that matter, so combining the two, birthdays and teddy bears, on a day made to honor him, or whatever, seemed like a really fucking bad idea. But, apparently not to the smiling nurse sitting beside him.
“Okay, so? What does my birthday have to do with five million teddy bears? In case you forgot, I’m not really into all things fluffy.” The younger boy flopped down onto the bed in defeat and draped an arm over his forehead to calm himself. Sometimes, Dean just couldn’t accept that, possibly, Rory was just doing something as a nice gesture. Honestly, was it that bad to think that Rory would just do something for the hell of it? The younger boy’s smug smile and teasing eyes, crying out ‘I know something you don’t’ proved otherwise.
“Oh, there’s no reason. Maybe, I don’t know, a younger Dean wrote a bucket list?” Dean groaned upon remembering, and Rory laughed, now awake, but too lethargic to move. The older boy glared, but said no more on the matter. That was, until a blindfold was tied around his eyes and he was being dragged out to the Impala. Then, he said a lot.
1. Skydiving
“No. Rory, no. This is a very bad idea.” Dean was still blindfolded, but he could hear engines running, and they were loud. Plane engines or jet engines. Rory knew he was horrified of heights and planes, and the fact that the younger boy had driven him somewhere where the two existed at once, made the hunter sick. The nurse, untied the blindfold from around Dean’s eyes, and smiled.
“Surprise! Number one on your bucket list, skydiving!” Dean grew wide eyed and almost choked. He was about to say something, but suddenly Rory was running out of the car and Dean had to follow. He would not to do this for anyone else, which he reminded Rory as they were, (poorly) trained, as Dean was putting on a jumpsuit and a parachute, as they stepped onto the small jet, as the previously mentioned jet was lifted into the air, and as Rory stood on the edge of the outside of a jet. This was suicide. He should go back to when he was four and kill himself, or at least burn this list. Rory smiled and turned to peck his fiancé on the lips. Dean had to smile at how much trouble Rory was going through for his birthday. It really was quite touching. But, what wasn’t touching, was when Rory hurled himself out of a plane, proclaiming, “THIS IS SO EXILERATING!” Dean jumped after him, of course, and fucking hated himself for it, because it was the worst thing ever. He almost had a heart attack. Twice.
It was kind of worth it to see Rory high on adrenaline, though. He was all kisses and smiles. It didn’t make up for the heart attack, though.
2. Paintball
The next thing he knew, Rory was pulling into an open field. The other boy raised an eyebrow and gestured to the field with a raised eyebrow. “What is this?” Rory smiled excitedly and handed Dean a gun. Not a normal gun though, it was loaded with something that looked like paint. Dean rolled his eyes.
“This, Mr. Winchester, is number two on your list: paintball.” He then smiled and walked out of the Impala carrying a separate gun. Dean followed reluctantly and shrugged.
“I don’t know Rory. I don’t think that this-“But then Rory shot him with a triumphant laugh and looked over at Dean mockingly, and all bets were off. The two men ran around like lunatics, just yelling and shooting at each other, and at one point, someone driving must have thought they were killing each other, because the police drove off to take them to jail.
And so they spent the rest of the night snogging in jail. As do all self-respecting Winchesters.