Fifty First Dates

Chapter 5

Dean and Sam had finally decided to leave town, with Castiel in tow. Castiel kept watching Dean as they packed up, and filled the car, checked out and drove off. But Dean didn’t seem to remember anything of the previous few days. Castiel sank into the leather backseat in relief, his eyes averted from the front seat as Sam read through several papers, discussing potential jobs with Dean. If Castiel were to raise his head and look forward, he would be inundated with memories of the morning before with Dean, lying in his arms, sinking into his chest, the firm-yet-soft feel of his lips against every inch of Castiel’s skin … even now it felt too much.

Castiel was still dwelling on their argument the night before, the one that erupted because Dean hadn’t immediately told that girl in the bar to get lost. He knew now that chasing after Dean would only lead to heartache, and no matter how hard he tried, Castiel would never have Dean the way he wanted. The awkward kisses from Dean on the sidewalk, in the car and just before going back into the motel room had been proof of that. Dean had been so distracted. There had been no passion there, nothing that could soothe the burning need Castiel felt when he was near Dean. And if dating him didn’t take that away, then what was the point?

The car stopped moving, and Dean climbed out of the car. Castiel looked up, and noticed that they were in a garage. He could hear from the scraping outside that Dean was filling up the car. Sam turned in his seat and looked at Castiel with concern.

‘Hey Cas, are you okay? You’ve been kinda quiet back there. Something happen when you and Dean were hanging out yesterday?’

‘No,’ Castiel lied, his voice softened with his heartache. ‘I’m just reflecting. You and Dean, you drive for miles and barely seem to notice the wonders that you drive past every day.’

Sam chuckled, reaching across the seat to pat Castiel on the shoulder.

‘Don’t ever change, Cas.’

Castiel sighed heavily. Maybe that was the issue, Dean would want him to change. Dean rapped his knuckles against the window from outside and waited for Sam to wind it down.

‘Hey man, I’m gonna grab something to eat. Anything you want?’

Sam shrugged.

‘Anything that’s not too unhealthy.’

Dean just laughed, and jogged away into the store to pay for the gas and grab some food. Sam turned back to Castiel.

‘Are you sure you’re okay?’

‘I’m fine, Sam,’ Castiel responded testily. Dean hadn’t even looked at him before heading into the store. He’d focused on Sam, and ignored Castiel completely. Castiel had definitely wiped Dean’s memories of the day before, so it wasn’t like there was any valid reason why Dean would be ignoring him so completely. Was there?

Dean climbed back in the car, passing the bag to Sam and placing the keys in the ignition. Sam poked through the bag, shaking his head as he did so.

‘Dude, all you got was whiskey, beer, jerky and pie.’

‘Yeah, because I don’t forget the pie.’

Castiel zoned out as they bickered for a few minutes about pie, and Dean finally put the car into drive.


At the new motel, Sam had gone to check them in, and Dean had turned in his seat to look at Castiel.

‘Hey man, are you okay? You haven’t said a word the entire drive. You haven’t even done that staring thing you do. Did I piss you off or something?’

‘No, Dean,’ Castiel sounded weary.

‘Well, okay. Look, Sam and me, we’ve got to see about this case. Sounds like a regular old haunting to me. But when we’re done, you wanna talk about that date?’

This was the only problem with erasing Dean’s memory with every passing date. He couldn’t remember why Castiel was so disappointed. He was smiling and looking as adorable as ever, his green eyes almost sparkling, the freckles more prominent than usual on his cheeks. He had no idea that the night before, he’d kissed someone else in front of Castiel and broken the angel’s heart.

‘We don’t have to worry about that, Dean,’ Castiel muttered. Dean narrowed his eyes, as Sam opened the passenger door and sat inside, without closing the door behind him.

‘We’re good to go. Room two-nineteen. Key.’ He passed a swipe card to Dean, who flipped it between his fingers a few times.

‘Thanks man. Hey, I’ll catch you up, I wanna talk to Cas for a second.’

Sam looked between his brother and the angel, and then nodded.

‘Okay. See you later.’

Sam grabbed his rucksack, and jogged into the stairwell. Dean watched his progress, and then turned back to Castiel, still frowning. Castiel wished he wouldn’t, the frown marred his beautiful features, and hid his eyes.

‘What the hell do you mean, we don’t have to worry about that? You don’t wanna go out with me any more?’

Castiel shook his head, rather than answer, and Dean’s frown deepened.

‘Tough luck. You can’t just spend weeks trying to convince me to go on a date with you then turn around and say you’re not bothered. I mean, did I do something?’

Castiel looked away, out of the car window.

‘No, Dean,’ he lied. ‘I’ve given it some thought and I realise that I shouldn’t have to convince you to date me. You should want to in the first place.’

Castiel missed Dean rolling his eyes.

‘Cas, shut up. Confidence is sexy, you know? You do wanna date me, and I said yes, so stop being such a damn child about it.’

‘I’ve changed my mind, Dean.’

Dean’s eyes narrowed further, as Castiel looked back at him.

‘I don’t know why you’re so upset over my decision, anyway. It’s not like you date men normally.’

And Castiel zapped himself out of the car before he could hear any more of Dean’s rebuttal.


Castiel had zapped himself to a remote mountainside somewhere in Nepal. Somewhere far away from Dean and his intense eye contact. Somewhere he could focus, where his vessel didn’t betray his emotions by physical manifestation. Somewhere his heart could break in silence.

The mountainside was beautiful, and virtually inaccessible, a contrast of high, grey rock walls, coated in lime green moss, and vibrant flowers growing in the most unlikely and impractical of places. Castiel was surrounded by evidence of his father’s artistry and love, and he sat at the edge of the small ridge he’d landed on, and held his arms around his torso as though he could stop his vessel from breaking.

He thought his decision to tell Dean that the pressure was off would be easier, that Dean would accept it and move on, maybe throw a few jokes at Castiel about the unlikeliness of their profound bond turning more profound. He didn’t expect Dean to take charge and order him to date him anyway. Yes, it was Dean’s style to take control and make decisions and follow them doggedly, but not with Castiel. Castiel was always more his equal.

Castiel felt more confused than ever. How could Dean treat him like an equal and make Castiel believe they had a chance at a relationship, and then treat him like everyone else the moment Castiel tried to give him his free will? Hadn’t they bonded over free will in the first place? Wasn’t that one of the lessons that Dean had worked tirelessly to teach Castiel? It was such an important human notion, the angel knew that.

And the way Dean had spoken to him, it sounded like with the memory wipe, Dean was almost enthusiastic for their “first date”, which confused Castiel even more. If Dean was enthusiastic for them to begin a relationship, then why had he kissed that girl? What was going on in the hunter’s head? And more importantly, how could Castiel return to the Winchesters without feeling his heart breaking?

Castiel stayed perched on the ridge, holding himself in, for hours. He spent most of that time debating over and over in his head what was going on with Dean, and trying to convince himself that he wasn’t in love with the hunter. And yet, eventually, he heard Dean praying, and all the resolve of the hours on the mountainside disappeared in favour of responding to Dean.

‘Cas? I know you’re still mad at me. I can’t figure out why, but … if you want to talk man, I’m ready. Sam’s met a girl from the case, he’s not going to be back all night, so we can talk this out. Just you and me. Okay?’

Castiel sighed, his whole vessel moving with the action. Dean made it sound so reasonable, as though by sitting in a dingy motel room as the hunter drank his way through a bottle of scotch would be all they needed to fix this. But Dean probably knew the truth, that Castiel was too enamoured to leave it alone. So of course he zapped back.

Dean had surprised him. The motel room was neat, almost to military precision. Almost, because Dean had covered the table in the small kitchenette with a cloth, and put on of his ritual candles on the table also. It was lit, and covered in a waxy build up from previous use where the molten beeswax had run down the taper. Beside the candle was a small vase with a single flower in it, a purple pansy that contrasted heavily with the green theme of the room. And Dean was leaning against the kitchenette worktop, staring at him in the candlelight.

‘What is this?’ Castiel asked, his tone harsh as he tried to work out the hunters’ motives.

‘Like I said, we need to talk.’ Dean shrugged, standing straight and approaching Castiel, shucking the trench coat off of the angel. Castiel watched Dean intently, their eyes fixed on one another, as Dean removed the coat completely and flung it onto the nearest bed. Castiel was reminded vividly of their time the previous morning in the car, and he felt his body responding to the sexual tension between them. His heart rate spiked, he could feel it thudding hard in his chest, his breathing faltered, and he could feel himself growing in his pants. Dean helped him out of his jacket also, his eyes locked on Castiel’s. He broke the silence. ‘You’re always trying to have eye sex with me.’

Castiel remembered Dean saying that yesterday, though the day before there was a teasing quality to the topic and now there was a quiver in Dean’s voice, as though suddenly there was more weight on that fact. And Castiel responded as he had before.

‘You’re not looking away.’

He saw Dean blink, as though he had been hit momentarily by deja vu, before he stood back, gesturing at the table.

‘Yeah, well, I wanted to do you dinner, the whole bit, but then I remembered you’re an angel, you don’t eat-‘

‘I’ll eat.’ Castiel sounded enthusiastic, and Dean did a double take.


‘Yes. I appreciate the effort, Dean.’

‘You know I’m counting this as our date, right?’ Dean smiled. Castiel looked again at the table, set out for a romantic date, and considered his options.

‘You only agreed to one date, Dean.’

That time, he saw Dean roll his eyes.

‘Okay, Cas, sit down.’ He pointed at the chair. Castiel crossed the room and sank into the chair Dean had indicated, feeling out of sorts. What had made Dean change from flirting to suddenly ordering him around? Dean crashed into the other chair, leaning onto the table, his face close to the tiny flame of the candle. ‘Look, I don’t know what’s going on with you, man, but you have to calm down. Okay? Just let whatever’s going to happen between us happen. Because I might not be here tomorrow, and this isn’t the way I wanna spend whatever time I get. Just stop over-thinking, okay? I said yes. That should be enough.’

‘Dean,’ Castiel shook his head, overwhelmed by Dean’s vehemence. ‘I-‘

‘I said yes, Cas. The least you can do is respect that.’

Dean glared at Castiel, and the angel looked away, at the lone pansy in the vase.

‘You’re right. You’ve gone to a lot of effort for tonight. Is Sam really out with a girl?’

Dean seemed to relax at the change in conversation, his tone changed completely.

‘Yeah. She graduated from Brown so they were talking college for forever. Somehow that earned him a date. And I figured since he was going to be gone so long, maybe you and me could work this out.’

Castiel nodded, and finally looked at Dean again, who was still leaning on the table, but now he was smiling slightly. Castiel felt emboldened by Dean’s demeanour, and sat closer, reaching a hand out towards Dean’s. Dean let him wind their fingers together, and stared down at their hands. Castiel was strongly reminded again of their intense make out session in the Impala, and Dean’s tenderness afterwards. He stood up, walking around the table, still holding Dean’s hand, and sat on his thigh the way the girl had the previous night. Dean bent his neck back, looking up at him.

‘Are you okay, Cas?’

Castiel didn’t trust himself to answer. He slid his other hand into Dean’s short bristles, until he was holding Dean’s head gently, and then he stooped down slightly, and pressed his mouth against Dean’s.

Every one of their kisses so far had felt different. Each one was enjoyable, but they all had a unique tone to them. This one felt tenuous, as though Dean wasn’t sure what to make of Castiel’s sudden attention despite automatically kissing back. It was slow, and soft, and Castiel found himself listening to the slight smacking sound that happened every time their lips parted, his concentration split between the feel of Dean’s lips pressed against his and the way Dean’s hand slid up his back, fingers splayed, where he applied a slight pressure. Castiel let Dean draw him closer, their bodies pressed against each other, Dean’s breathing beginning to falter as he pushed his tongue through Castiel’s lips. The tenuous nature of the kiss had gone, dissipated in the growing passion between them. Dean dragged the hand he was holding up, until their clasped hands were pressed between their chests, and then he unwound his fingers from Castiel’s, and slid his hand under Castiel’s ass, squeezing slightly as his palm caressed Castiel through his slacks.

And then Dean lifted Castiel up, nudging Castiel’s legs around his waist, and stood up, carrying the angel to one of the beds, where he fell backwards, and brought the angel with him, on top of him. Castiel could not believe that they were in Dean’s bed in a mess of limbs. He remembered Dean kissing down his neck the previous day, and decided to repay the favour to Dean. He regretted leaving Dean’s lips the moment that he made the decision, but it was worthwhile to hear Dean gasping for breath, to feel Dean’s stubble scratch at his lips as he worked down Dean’s chin with small kisses, along the sensitive skin under Dean’s jaw and along to the side, where his kisses sent Dean into a spasm, his body rolling under Castiel’s as the angel kissed and licked and nipped at the same part of Dean’s neck.

‘Fuck, Cas,’ Dean gasped out. Castiel smiled to himself, enjoying hearing Dean fall apart, loving the fact he could feel Dean’s heart thumping in his own chest, competing to be as ferocious as Castiel’s. Maybe the hunter did love him in the same way, and Dean was always too conservative to let it be known? Castiel wasn’t concerned with the details at that moment, he was more concerned with turning Dean to putty. He began tugging at Dean’s over shirt, pushing it off, trying to balance over Dean as he realised what Castiel wanted, wriggling out of the shirt and flinging it to the side, pulling off his under shirt and flinging that out in the same direction, onto the other bed. Castiel gazed down as Dean’s firm, muscular chest and torso, tracing a finger over Dean’s well defined abdomen. Dean laughed, letting go of Castiel’s ass to reach up and slide his hands into Castiel’s hair, tugging Castiel gently back towards him. ‘Man, if this is what you’re like when we’re not on a date, I can’t wait for when we’re on one.’

Castiel slid his arms around Dean’s ribs, sinking into him as Dean continued to coax him down.

‘I thought you were counting this as our date?’ Castiel reminded him, his voice shaking with lust.

‘Maybe I’m getting greedy.’ Dean smirked, pushing his head up to meet Castiel’s so they could kiss again.

‘I like you greedy,’ Castiel admitted with his lips pressed against Dean’s. Dean laughed, his whole frame rocking, and Castiel’s erection grew, pressing against Dean’s leg.

‘Mmmm, talking of greedy,’ Dean laughed, and wound Castiel’s tie around one hand and pulled him even closer, licking into Castiel’s mouth. Castiel could feel Dean’s body temperature rising, despite not wearing a shirt, and beads of Dean’s sweat permeated Castiel’s shirt. Castiel felt emboldened by Dean’s enthusiasm, and he forgot his earlier lament completely, stroking his hands down the sides of Dean’s body, enjoying the way Dean thrust out beneath him, as he inched his way to Dean’s jeans, intent on working them off next.

And then a strange beeping filled the room, and Dean tucked his chin down, making it difficult for Castiel to continue kissing him.

‘Cas, that’s the food.’

‘Forget about it.’ Castiel insisted, running his nose down Dean’s as he tried to capture the hunter’s lips once again.

‘I can’t Cas, I can’t burn this place down. And I’m hungry. Just let me eat, and we’ll get back to this, okay?’

‘Do you mean that?’ Castiel breathed, his teeth working on Dean’s full bottom lip. Dean sniggered.

‘Of course, Cas. Now let me up, before it burns.’

‘Make me,’ Castiel smirked. Dean grinned back, and pushed Castiel off him before rolling off of the bed and making his way back to the kitchenette, grabbing a potholder and taking a tray out of the small oven. Castiel propped himself up on his elbow, and watched as Dean walked around, finding a plate and a fork, serving up his food and placing it on the table. Castiel paid attention to all of Dean’s movements, the way his muscles flexed and tendons pulled, how he nodded his head as he hummed, focused on the food. Dean looked up as he sat down, and caught Castiel’s eye.

‘Did you want some?’

‘I’m sure it’ll just taste of molecules,’ Castiel shrugged. ‘Watching you eat will be good enough for me.’

Dean smirked, and shook his head, sticking his fork into his dinner.

‘What did you cook?’ Castiel asked, still watching Dean’s naked torso. He was glad Dean hadn’t put his top back on, because he got to stare hungrily at Dean while Dean ate.

‘Pot pie. You sure you don’t want any?’

‘I’m sure. I know how you feel about pie.’

Dean smirked again, and carried on eating. He worked through half of the pie before they heard footsteps outside, and heard the slide of the keycard in the lock. Castiel clicked his fingers quickly, just as the door began to swing open, and the tablecloth, candle and pansy disappeared. Dean remained topless. Sam looked around the room, his expression perplexed.

‘Guys? Is everything okay?’

‘Yes. How was your date?’ Dean asked before shoving more of the pastry crust into his mouth.

‘Good. She was nice.’ Sam nodded. ‘Any reason why you’re not wearing a shirt?’

‘I got hot,’ Dean shrugged. Sam nodded, and looked over at Castiel, who looked back innocently. Sam raised his eyebrows, but said nothing more about the scene in front of him.

‘Got any of that pie going?’

Dean chuckled.

‘Nope, all mine. I think there’s still some jerky?’

‘You’re an asshole.’ Sam told Dean, before crossing the room and flopping on the other bed. ‘And dude, don’t leave your shit on my bed.’

Sam flung the shirts back towards Dean, where they fell short and covered Castiel’s face. Dean and Sam both started laughing, but Castiel didn’t care. The cloth smelled strongly of Dean, and all Castiel wanted to do was bunch it up and sniff it heavily. If Sam wasn’t there, he would have. He peeked out of the material and caught Dean’s eye, and the lust that was in there as well as … an apology? Castiel accepted that there would be nothing more between himself and Dean that night, but from the look in Dean’s eye … maybe Castiel could relent and let him remember today? After all, things were looking up between Dean and himself. Maybe Dean felt something for Castiel that could begin to compare to the angel’s emotions?

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