I Wasn't Prepared For This
Summary: Dean is homophobic because something happened when he was younger: he fell for one James Novak, but James rejected him. Dean knows from then on that he should only be with women... so why is Castiel - in his male form - giving him so many feelings?
-past-
Dean Winchester was a ladies' man. Well, ladies boy, as you can't exactly call him a man at the age of 14. He made it a point to kiss at least 5 girls from every middle school he had to stop at and being at a different one every other week… he definitely got around.
He decided he was going to up his game at the newest school he was hitting in Pontiac and hit at least 10 girls. He figured with the month deadline his father gave them that he could accomplish it. What he didn't expect is to meet James.
James Novak was sixteen and lived just down the street from the motel John set Sam and Dean up in. He was a scrawny little thing with unruly dark hair and vibrant blue eyes. Dean swore that from the moment he looked into those eyes, he would never forget them.
Sam, of course, was the one to start the interactions with the Novak boy. He was outside playing with a soccer ball, one he got from Uncle Bobby and hid as well as he could from John, and accidentally kicked it out into the street, hitting the unsuspecting James as he rode by on his bike. Dean watched this from the doorstep of the motel room and ran out to scold Sammy and apologize for his idiot little brother, but was stopped dead upon approaching the stranger.
James smiled and accepted Sam's frantic apology, asking if he could join the 10-year-old in kicking the ball around the parking lot. He ended up offering his front yard, and Dean eventually joined in. After a while, when it got dark, James had to go inside and do homework, but offered to play another day, Dean didn't even hesitate to say yes, and he told himself that it was Sam's resulting smile that was what made his chest light.
Of course, James kept his word, but Sam had to stay after school to do a group project, so Dean hung out with James. He found out that James was an only child, a devout Christian (much to Dean's disgust), and not interested in dating until he was in college. Dean laughed at that, wondering why someone, especially someone as attractive as James would not be going after all the girls (because surely they were all going after him). James wormed his way out of that conversation, saying he was focusing on his studies.
Dean let it go, he wasn't about to talk about feelings, John raised him better than that, and he continued to hang out with James every day, with Sammy, without Sammy. It was nice having a friend. He forgot about his plans for conquest on the young ladies of Pontiac, so wrapped up in James and what James wanted to do. He was sure that if James asked him to, he'd commit a serious crime.
Then one day, Sam was again working on a project at school and the Winchesters were getting near the end of their stay in Pontiac, Dad was going to be coming to get them in a few days, and Dean was once again hanging out with James, they were at the motel room so that when Sam came home Dean would be there to greet him, and they sat on the bed watching something Dean's seen a million times and James had never seen. Dean felt so comfortable sitting there next to his friend, their arms barely touching, James watching the screen intently. He found it cute and was overtaken with the sudden urge to kiss his friend. So, being the horny teenager he was, he did.
James melted into the kiss momentarily before quickly shoving Dean off of him. Dean doesn't remember the specifics, but James leaped up and took off, spouting something about "sin" and "hell." All Dean really remembers was his heart being broken, and learning to never kiss a guy again.
-later-
Dean knows the guy saved him from Hell and all, but he wouldn't hate him so much if he wasn't such a dick. Seriously, this guy (angel, whatever) shows up invading his dreams and personal space, has the gall to ask him to torture again, and then asks for help. And just when Castiel was getting to the point of being bearable, this shit happens.
Jimmy makes Dean feel weird, sometimes he looks at him like he knows something and won't share it. Dean writes it off as Jimmy hiding whatever the demons want to know, but something just doesn't feel right.
Just before Jimmy goes off into the warehouse, he turns to Dean, "Don't you remember?"
Dean's look of confusion tells him that no, Dean does not remember.
When Cas takes back the body, he wonders if that would have changed anything, but then he remembers that he's not supposed to care.
-later still-
Dean can't stand when Cas comes back and is all Mr. Asshole again. But then Cas is back to doing things that make him believe he wants to be different, that he's not the hammer Dean likes to think he is.
Which leads them to where they are right now: Dean's locked in this pretty little room with Cas standing just behind Zach who is telling Dean how he's needed, and then disappearing with Castiel. Neither are going to let him see Sam and make things right. They're just going to have him sit and let the world burn.
Dean can't believe Castiel is going to let this happen. He loves his father's creations and now he's just going to stand there and watch them burn. Dean's trying to appeal to him, he knows Cas, knows he cares and considers him a friend.
"We're done."
In the end, when Cas breaks and helps him, Dean's heart swells. He tells himself that it's pride.
-later still-
Friends help their friends with whatever problems they may have, and Dean's going to stick by the fact that the brothel visit was necessary, even if it was unsuccessful. He's not going to talk about the pressure that let up when he ended up taking Cas back to the abandoned house with his virginity still intact.
He also isn't going to talk about how his voice breaks when he's faced with this future version of himself telling him that he doesn't care about anything anymore, that he's just going to send the future – broken – version of Castiel to his death without a second thought.
"Cas, too?"
Dean can't take this. He knows now that Castiel means so much more to him than anyone but Sam ever really did. But he's not letting that mean that he's just going to rush into Cas's arms when he gets back and Cas saves him from Zachariah once again. He gives him a manly touch on the shoulder, and the three words he can force himself to say.
"Don't ever change."
It's not love because he can't love Cas. Boys can't love boys. He learned that long ago with James, these feelings he has, they're not and they can't be love.
-later still-
Dean missed Cas. When he left him for a year, he missed him nearly every day. Lying there with Lisa didn't have the charm it should have, but he told himself he'd do it for Sam, and he did. Then Sam is sitting across from him and Cas is standing three feet away. He's actually here.
"Hello."
Sam might be pissed, but it's nothing to the category five storm of emotions swirling around inside of Dean. He just goes with it, with everything Cas asks, in turn asking more of Cas than before because "you left me" rings out inside his head as an excuse, a free pass for all these things he asks of Cas. He also piles in the rage he feels inside of Cas kissing Meg, telling himself that it's because she's a demon and not that other reason swimming around trying to breach the surface.
-present-
And now, Dean's hurting.
"I was there, where were you?"
He meant it in so many more ways than he could have imagined and hoped Sam and Bobby just let it slide.
He can't convince Cas to give up this stupid crusade like this, so when the angel visits him that night, he buries down everything he ever thought about how things should go and pulls him into a kiss. Cas melts into him and Dean is scared. Cas can do more than James who merely pushed him away. Cas could end him, but instead, Cas nips at his lips, asking for more.
Dean's not sure where this is going, or why he's suddenly okay with it, but he knows that Cas won't let him fall.