Log in

No account? Create an account
14 February 2010 @ 06:19 pm
[fic draft] Five AUs Where Dean and Castiel Fell in Love... And One Where They Didn't  
I literally just typed this whole thing. This is for pandatini. I will go back and fix horrible typos and edit later, but I said I was gonna type this up and post it before I had to get ready for dinner. So here it is! *runs to shower and primp*

Five AUs Where Dean and Castiel Fell in Love... And One Where They Didn't


He usually had his headphones in, and they were loud enough that Castiel could hear the edges of old 80's music coming around far before the mail cart ever came into sight.

Dean was young, and oblivious, and probably a stoner, and Castiel didn't tend to like that type. Still, he made a point to nod and thank the mailboy every time, because he was a fellow human being, and that was the polite thing to do. He felt bad on the few days he was working so hard on processing someone's impossible claim that he didn't even notice Dean come by. Those days happened, though, and it was on one of them that he suddenly, after about five minutes of re-reading the same twenty words, noticed that Dean was standing there staring at him.

He looked up, spooked. Dean bolted.

The next day, on guard and a little unsettled, Castiel made sure he heard him coming. He nodded, gave a simple thank you when the mountain of envelopes made its way to his desk. And Dean didn't turn his cart around and wheel it out of sight. Instead, he plucked out his earphones. Aerosmith blared for a few moments before he fished his iPod out of his pocket and shut it off.

"Um, can I help you?" Castiel asked.

"I just wanted to say thanks," Dean said. His voice was lower and more mature than Castiel had expected. "You treat me like a human being most of the time, and not so many people around here do. Just... thanks for being decent."

Castiel felt his heart accelerate. "You... you're welcome," he said.

The next day they ended up in the elevator together. Again, Dean pulled out his earphones. "Hey there," he said with a cursory wave.

"How are you?" Castiel said stiffly. Nice or not, he doubted he and this boy had anything in common. This conversation would be awkward.

"Good. I'm glad to see you again, man. I always figured... well, I thought it'd be fun to talk to you."

"To me?" Castiel stared at him. Easy to talk to was not one of his foremost attributes.

"Well, maybe not talk so much," Dean said. "That sounded wrong. What I mean is, everyone I know wants to talk all the time. I just get the feeling you're kind of guy who doesn't need to say much. You know, it'd be cool to just hang out. Watch a game, just... just be."

Castiel stared at him. "I don't get your meaning."

"Hell." Dean looked at the ground. "Look, this is my weird way of asking if you want to come over and watch the game or something on Sunday. I know, I'm not really smooth. Forget I said it."

Castiel did no such thing. And come Sunday, as the linebacker ran the ball into the end zone and the crowd went wild, Castiel was too busy kissing Dean to much care.


Dean was getting his ass beaten.

The jury found for the defendant in an amount of $200,000, and his client stormed off in a huff. God damn, how did that bastard Castiel do it? He seemed like the least charismatic person in the world. Yet get him in front of a jury, and he knew exactly what to say. This was the third time he'd gone up against the jerk, and every time he came out on the losing end. If this kept up, the partners were going to try and keep him out of court entirely.

Now he was sitting in Central Park feeding bits of his hot dog bun to the birds and feeling sorry for himself. Why the hell hadn't he become a truck driver like he wanted when he was a kid? This lawyer stuff sucked.

"You know what your problem is," said a voice behind him. "You're always looking for a fight."

Aw, crap.

Castiel sat down on the bench beside him. "By the time a case goes to trial, the parties involved are exhausted. And by the time the jury renders a verdict, the jurors are tired. What you need to do isn't convince them finding for your client is the right thing to do. You need to convince them it's the easy thing to do."

"Oh, and isn't that an expression of faith in justice," Dean said, rolling his eyes.

"Not everyone is a hero the way you are, Dean." His countenance was blank and his words were uninflected.

Dean shot him a glare. "Why are you here, anyway? To rub it in with your phony advice? Save it. I'm not in the mood."

Castiel's gaze was on him, and Dean could feel it bright as laser sights. "I like you," Castiel said simply. "You're a good man. I'd like it if you didn't hate me so much, just because we end up on opposite sides of the courtroom so often."

Exasperated, Dean threw the rest of his hot dog bun to the ground and watched the pigeons attack it in a cluster of feathers and beaks. "I don't care enough about you to hate you, Cas," he said, and got up.

Castiel looked up at him. "Dean--"

"Forget it." Dean spun and began to walk, fast as he could, away from there. He stepped off the path and up a steep, grassy hill into an area where trees blocked out the sky with wide green-laden branches. He could hear Castiel behind him. He didn't turn.

"Look at you," Castiel shouted after him. His voice was gruff, low. "You're purposefully taking the hardest possible path, and then you wonder why people don't want to follow you."

"You are following me," Dean shouted back, but then Castiel had caught up with him and was pushing him to the side and against the trunk of one of the thick trees. "What the hell are you doing?"

"It used to be easier to ignore you," Castiel said, dark and glowering into his face. "I can't do that anymore, Dean. And you can't ignore me either."

Dean struggled. Being this close to Castiel was doing things to his body he didn't want to admit to, especially not in front of this bastard of a rival of his. "Why the hell not? You get under my skin, Cas. You piss me off. You want me to start throwing punches, or you want to leave me alone?"

Castiel smiled and shook his head. "Again. You're leaving off the easiest option."

"Oh, and what is that supposed to be--" Then Castiel's kiss shut him up but good.

Dean moaned, opened his mouth, and leaned back against the tree, let Castiel ravish his parted lips with soft melting kisses. His hands came up to grab Castiel's tie, pull him closer until he could smell the detergent he used on that everpresent trenchcoat of his, could feel the line of his body and the heat radiating out from every pore.

When it was all over, Castiel very nearly smiled. "See? Easy."

"Oh, I can think of something that's hard," Dean said, pulling him close again.


They all said Senator Winchester was going to be president someday. Castiel thought he had more of a chance of being Miss America.

The guy could give a speech, sure. But honestly, he couldn't even govern his own office. Castiel was being waylaid by a thousand different aides, each of whom was giving him different ideas of when the senator would be available to talk to him, what his policy positions were, the status of the relationship between him and the socialite of the week. Nobody seemed to know which end was up. And it wasn't like Castiel didn't have another press conference to cover at the other end of the Capitol at 2:30. A few more minutes and he'd probably have to just go.

Still, when the senator walked into the office from the hallway, filling it with his broad shoulders and air of power, Castiel had to swallow hard.

"Mr. Novak. Please come into my office," he said, and the booming voice made Castiel's toes curl. He didn't stop moving, sweeping through the reception area and opening his office door in one long, fluid motion. Castiel followed dumbly, his eyes silently taking in the measure of the man before him. He certainly looked presidential.

Dean closed the door and crossed to his desk, leaning back against it. "Stop staring, Mr. Novak, or I'll start doubting you can cover this story objectively," he said with a wide grin.

Castiel pinked with the innuendo. "I only need a few minutes of your time, Senator. I wanted to ask you about the rumors that you've formed an exploratory committee--"

"Really?" Dean tilted his head. "That's what you came all the way here to ask me? About my exploratory committee?"

"Is it true?" Castiel felt like a base rookie. Stick to the question, he told himself. Stick to the question.

Dean laughed. "You didn't bring any cameras this time. I'm surprised. I thought you'd bring an entourage."

"Your aides said off the record. I hold up my end of the bargain."

"Then I'll hold up mine." Dean advanced toward him. "Off the record," he said. "Deep, deep background. Got it?"

Oh. He was very, very close. Castiel nodded.

"There's a very, very good reason this country's not ready to have me as president." Dean reached out and touched Castiel's arm lightly. "If you like, I'll give you an exclusive look at why."

The touch lingered. Castiel looked down at Dean's fingers, pressed against his sleeve, and knew there really was no way he'd be able to cover this story objectively.

And that was really all right with him.


When Dean came into the job, about five years ago, he'd called Castiel his guardian angel. These days, Castiel felt more like he'd taken on the role of the devil himself.

But Dean had gotten sloppy. Sloppy and incompetent. He was misfiling things, he was forgetting appointments, he was hitting Reply to All on the most embarrassing possible e-mails. It was tough enough being the only two male secretaries in the firm, but ever since Dean had broken up with that girl Anna, he'd been a mess.

Castiel had introduced them. He'd known Anna for a long time, and he thought they'd make a good couple. And they did, for several months. So much so that he was fairly sure Dean was working on putting something aside for a ring. But about a month ago, something happened, and that was it, it was over. And now Dean was making them both look bad.

So as much as he hated to do it, he pulled Dean aside one evening when they were both working late and laid into him. "You need to take your work more seriously," he said. "It reflects badly on both of us, and at this rate, I'm afraid you're going to drag me down with you. I know you're hurting, but you need to remain professional."

Dean was breathless and flushed, his hands tight fists on the back of the chair. "I don't want to hear this crap from you," he said.

"That's too bad." Castiel scowled. "Because you still have to live your life. There will be other women, and you can't let yourself go down in flames just because of one."

And Dean gave him a look that Castiel was not expecting. "Women?" he said with a laugh. "You think I'm flipping out over a woman? Jesus, Cas, you are unbelievably dense."

"I don't understand. This isn't about Anna?"

"No! Well, yes and no. It is and it isn't. Cas, did you talk to her since we split up? Did she tell you anything about what happened?"

Castiel thought back to that one strange phone conversation. You need to know, Anna had said to him. It's really important.

When Dean's ready, he'll tell me, Anna, Castiel had insisted. I can't become your confidant. It wouldn't be fair to him. He's my best friend.

Now, he wished he'd shut up and listened. Because Dean's expression was baffling him.

"You are the most frustrating person I've ever met," said Dean in a low voice. His eyes blazed. "You're right, I am having trouble concentrating at work because I can't get my mind off someone. And it was Anna who helped me figure that out. So yeah, it is her fault. Kind of. But it's your fault, too."

Blindsided, Castiel just shook his head.

"I mean, I really thought you'd get it. But not once, Cas. Not once did you look over here when I was supposed to be taking dictation and see me staring at you instead. Not once did you realize I was listening in on your phone calls trying to figure out if you had a date or something, trying to figure out if there was any chance you were talking to someone about me. To see if I made even a dent in your perfectly organized little world."

Castiel's hands flew to his face. Dean grabbed them, pushed them down again. "Dean," Castiel began, but he didn't know what he was going to say.

And Dean didn't let him say it. "Anna and I broke up," he said, "because she realized I was really in love with you. And she was right. I'm sorry if that's inconvenient for you, but that's the way it is. So if you're going to go off on me about how lousy my work's gotten, you'd better take some responsibility for making me fall so damn hard for you."

"That--" Castiel began. "That's impossible. You're straight."

"And you're asexual as far as I know," Dean said. "Didn't stop me. Cas, tell me I have a chance. A half a chance. Or tell me I don't. Just... just give me an answer."

There was a long, long silence.

Then Castiel smiled. "As far as you know, huh?"

It was Dean's turn to be blindsided. "Huh?"

"It's no excuse," Castiel said sternly. "It's definitely possible to keep the quality of your work up even if youre carrying a torch for your co-worker. I've been doing it for five years now."

He gathered Dean in his arms. "You better shape up after this," he chided softly as he brought his mouth to Dean's in a long-awaited first kiss.


Dean was fairly sure he'd seen a porno like this once. Abandoned highway, gorgeous fellow on the side of the road next to an unhappy-looking car whose rear wheel was completely flat. Well. He didn't necessarily have to be in Boston for another few hours. The meeting couldn't start without him, after all.

He pulled over and got out of his car. "Problems?" he said.

The man looked at him with huge, pleading eyes. "Can you help?" he asked in a low, gritty voice that sounded like a huge order of sex with sex on the side.

"God, I hope so," Dean said under his breath and moved toward the car. "You have a spare?"

The man shook his head. "I'm no good with cars. And my cell phone is out of batteries. Could I use yours to call AAA?"

Dean blew air through his lips. "You don't need a tow," he said, "just a pump. I have stuff in my trunk. Hang on a sec."

Between pumps and heaving breaths, Dean listened to the man's story. He was on his way back up north from a meeting in New Jersey, he was in advertising just like Dean was, he was smart and single and gay and just about everything Dean had ever dreamed of. And Dean wasn't ever going to see him again, because Dean had a meeting and so did this guy, and they were both late.

Finally, the tire was patched up. Dean stood up.

"You've got dirt all over your suit," the man pointed out.

"It'll add to my street cred when I get to the meeting."

"Let me give you some money to cover the dry cleaning." He was going for his checkbook already.

Dean grabbed his hand without thinking of it. "Don't." Heat raced up his arm. Shit, he'd really let his fantasies run away with him. And now their skin was in contact, and it was just as electric as he'd anticipated.

"Let me," the man said. He shook him away with surprising strength and began to write a check. "Whom should I make it out to?"

Dean gave a sigh. "Dean Winchester," he mumbled, feeling defeated and like this day was one big tease that would never end.

The man stared at him. "Did you just say Dean Winchester?"

"Um. Yes."

"I'm Castiel Novak."

Dean's jaw hit the dirt. "You're Cas Novak? As in Cas Novak of Thursday Productions?"

"And you're Dean Winchester of Singer & Edlund. I believe we were supposed to meet."

"Well, fuck me," Dean said without thinking about it. He clapped a hand over his mouth. "Whoa. Sorry."

"Don't be," said Castiel. He reached out a hand and threaded his fingers with Dean's. "If we can find a motel that has dry cleaning, it might just be the best idea anyone's had all day."



It wasn't a drive Dean relished taking. But things had gotten bad. Dad was missing, and as much as Dean didn't really want to pull the poor guy out of his life he didn't much have a choice in the matter. He needed help. So he snuck into the room past midnight, and after a few choice punches and at least one decent throw, the light went on and it was showtime.

"What do you want?" Castiel asked.

Dean fixed his eyes on his brother. "Dad's on a hunting trip," he said, his voice slow and purposeful. "And he hasn't come home in a few days."

*the end*
pandapandatini on February 14th, 2010 11:36 pm (UTC)
I was going to say things about some of these but then I got to the last one and







That is all.
Tiptoe39: sorry! - venustiptoe39 on February 15th, 2010 02:03 am (UTC)
is that a good keyboardspam or a bad keyboardspam? I'm sorry, I couldn't help myself, really.......................... (O.o)
The Soul says: - pandatini on February 15th, 2010 03:59 am (UTC) (Expand)
The Soul says: - tiptoe39 on February 15th, 2010 12:38 pm (UTC) (Expand)
The Soul says: - pandatini on February 15th, 2010 05:30 pm (UTC) (Expand)
The Soul says: - tiptoe39 on February 15th, 2010 05:45 pm (UTC) (Expand)
The Soul says: - pandatini on February 15th, 2010 05:53 pm (UTC) (Expand)
The Soul says: - tiptoe39 on February 15th, 2010 06:08 pm (UTC) (Expand)
The Soul says: - pandatini on February 15th, 2010 06:22 pm (UTC) (Expand)
The Soul says: - gabs186 on December 24th, 2011 08:16 am (UTC) (Expand)
The Soul says: - tiptoe39 on December 24th, 2011 02:35 pm (UTC) (Expand)
Shonaille: Christina Hendricks Heaven Sentkalikahuntress on February 14th, 2010 11:42 pm (UTC)
Oh boys.:)**draws hearts around them.** These were all fantastic, thank you!
Tiptoe39: Cas smilestiptoe39 on February 15th, 2010 02:03 am (UTC)
ahahah, I'm glad you enjoyed. it was just a something-or-other I threw together for fun. :)
speccygeekgrrl on February 15th, 2010 12:15 am (UTC)
Awww. I think I liked Senator Winchester and the one where they're both secretaries the best. ♥
Tiptoe39: dean funny facetiptoe39 on February 15th, 2010 02:03 am (UTC)
I am really a sucker for a charismatic senator soooooooooo.... yeah. (O.o)
(Deleted comment)
Tiptoe39: castieltiptoe39 on February 15th, 2010 02:04 am (UTC)
no need :0 Thank you hon! and I love your icon :D
Kevin Jonesmulder200 on February 15th, 2010 03:18 am (UTC)
Wow! I loved them all.

The last one was a trip.
Tiptoe39: dean/castiptoe39 on February 15th, 2010 03:41 am (UTC)
Heh. Just wanted to screw with your head as usual.


Glad you liked!
Leoaslana on July 5th, 2010 11:41 am (UTC)
I love all of these AUs, because they are all awesome, but I have to admit that my favorite is the last one. Playing the Dean and Cas as brothers that *don't* fall in love (especially in this fandom! lol) is a smart move in counterpoint to the other tales you weaved.
Tiptoe39: gabriel - that was all metiptoe39 on July 5th, 2010 02:25 pm (UTC)
Wow, honestly, I had forgotten I even wrote this!! lol :D too much ficbunny to keep them all straight :DDD Thank you so much and I am so thrilled you enjoyed it!! :D
The Soul says: - aslana on July 13th, 2010 03:51 am (UTC) (Expand)
The Soul says: - tiptoe39 on July 13th, 2010 07:43 am (UTC) (Expand)
when i get older: alexis-2hrtslkths on July 28th, 2010 12:09 am (UTC)

But srsly, "deep, deep background" is like, I dunno, ridiculously awesome. So is the forthcoming Wincest at the end there. I want to hug them all to pieces and then make them dance for me. (I don't know, I just got home, my brain is fried.)
Tiptoe39tiptoe39 on July 28th, 2010 12:25 am (UTC)
Thank you bb! I'm glad you liked. I'd write more but like I told you, on deadline :DDD

platinumspider on August 18th, 2010 07:17 am (UTC)
I was scared to read the last one..
But it was freakin' awesome. Did. Not. See. Coming.


Someone has to do a pseudo-Wincest on Dean/Cas, stat.

As for the others, I think I loved the lawyers and businessmen one the best. Not sure why, but all of them are amazing anyway :]
Tiptoe39tiptoe39 on August 18th, 2010 11:08 am (UTC)
haha! Thank you! Where'd you find this, the Big AU List? It's sort of old, and not on my fanfic list, so I'm curious. I am inordinately fond of the lawyers one too :) So glad you liked!
The Soul says: - platinumspider on August 18th, 2010 05:44 pm (UTC) (Expand)
The Soul says: - tiptoe39 on August 18th, 2010 05:46 pm (UTC) (Expand)
carma_baby: Bones awesomecarma_baby on August 22nd, 2010 01:32 pm (UTC)
See! Now that I have finally seen the whole series, I can go back and slowly read through and actually understand what is happening with these characters. ^_^

I love your 5 things that did happen and 1 time it didn't s. They are always so fun and interesting. The last one had me really confused at first and almost literally scratching my head. Then I read it a third time and understood. And giggled.

Love. Always with the love.
Tiptoe39tiptoe39 on August 22nd, 2010 02:02 pm (UTC)
heee! Thank you! So much love for you in return! :DDD
twfftwtfwftw on August 25th, 2010 01:30 am (UTC)
I was going to tell you which one was my favourite, but I like them ALL.

(although I do love: "Oh, I can think of something that's hard," Dean said, pulling him close again. Snerk. Stay classy, Dean.)
Tiptoe39tiptoe39 on August 25th, 2010 11:23 am (UTC)
Classy with a capital K, that's our Dean. :DDDDD So glad you enjoyed themmmmmm!
The Soul says: - tfwftw on August 25th, 2010 11:55 pm (UTC) (Expand)
verob2002verob2002 on October 30th, 2010 11:52 pm (UTC)
Tiptoe39: team free willtiptoe39 on October 31st, 2010 11:29 am (UTC)
awwwwwwwwwww thank you! love back atcha!!
wolfrider89: Em Misha approveswolfrider89 on August 30th, 2011 07:14 pm (UTC)
Found this on The AU List, and weee, did I love it or what? I especially enjoyed the secretaries, I could feel the UST there. :D
Tiptoe39tiptoe39 on August 30th, 2011 07:22 pm (UTC)
Thank you so much!! :D
and that is not how I'm introducing myselfremey on November 1st, 2011 07:46 pm (UTC)
i'm in agreement with the first comment on this - i loved them all but when i got to last one .. a;dh;aglkdshg;asdlkgha;kdhg.
Tiptoe39tiptoe39 on November 1st, 2011 07:49 pm (UTC)
daww, sorry about the keyboard spam :DDD thanks for reading!
WHERE DO YOU EVEN BUY A BABY-BLUE KERCHIEF?oywidapoodles on April 11th, 2012 11:10 pm (UTC)
Wait. WAIT. What. That. AAAAHHHHHHHH I need more of the last one. Like now. And Sam as an angel and just yes, want now.
Tiptoe39tiptoe39 on April 11th, 2012 11:12 pm (UTC)
loooool! I'm glad you approve. That is, I THINK you approve... :D
The Soul says: - oywidapoodles on April 11th, 2012 11:55 pm (UTC) (Expand)
The Soul says: - tiptoe39 on April 12th, 2012 01:21 am (UTC) (Expand)
Nessiebaum (the loch ness monster): misha moustacheawillowcabin on September 1st, 2012 09:46 pm (UTC)
Ahhh, that last one! The other ones were great, but I'm totally in love with that last one. You should totally expand on that and make it into an actual fic all by itself ;)