Fifty First Dates

Chapter 4

Castiel still couldn’t believe how affectionate Dean had been in the Impala, even hours after they had finished making out, touching, exploring each other’s bodies. Eventually, mouths swollen and red, skin slightly chafed, they had just laid together along the front seat, their legs tangled together, fingers interlocked as they rested.

‘So, since this was just fooling around in the car,’ Dean spoke eventually, his breath warming a spot on Castiel’s neck. ‘Did you just wanna make the whole day a date? We’ve got all the time in the world. Sammy can live without us for the day.’

‘Okay,’ Castiel sounded unsure. He hadn’t banked on Dean actually showing an interest like this, or taking charge.

‘You got anything in mind for what we could do?’ Dean’s thumb started stroking softly along Castiel’s hand, sending small shivers of pleasure over Castiel’s skin.

‘Um,’ the truth was, Castiel had used most of his imagination on paintball, and he really hadn’t enjoyed the experience.

‘It’s cool. We can drive around, look for something. It’s not like we have a curfew, right?’

Castiel shifted his head along the leather, looking intently at Dean, trying to understand what he meant.

‘Come on, angel boy,’ Dean kissed his nose gently, and sat up, pulling his shirt back on and untangling his legs from Castiel’s. Castiel sat up slowly, taking his shirt and sliding it back on as Dean started the car back up, driving out of the field and scouring the horizon again.

‘So, fancy cattle wrangling?’

‘What’s that?’

‘God knows. Okay, a hay ride?’

‘Isn’t hay immobile?’

Dean burst out laughing.

‘Oh, man, Cas! Okay, um, wanna catch a game?’

Castiel pressed his lips together, trying to understand what Dean meant. Dean seemed to interpret his silence correctly.

‘A ball game, Cas. Football, baseball, whatever. We’ll get some rickety old seats and eat hotdogs covered in ketchup and mustard. It’ll be fun.’

It didn’t sound like so much fun to Castiel. It sounded exactly like paintball, like Dean could play macho and ignore the tension between them, and Castiel wanted it to feel like a date. He wanted all of Dean’s attention, all of his eye contact. He wanted to unlock all the secrets that Dean kept locked so close to his chest. He wanted the chance for intimacy, and privacy, like they had just experienced. But Castiel was aware that describing such detail to Dean would chase him off. Dean was still playing it safe.

‘What about a bar?’ Castiel said eventually. Dean looked at him out of the corner of his eye, and Castiel pretended not to notice.

‘Sure, we can go to a bar.’ He nodded.

‘Not one of the ones you normally go to, with the black walls and sticky floors and three types of drink.’ Castiel decided. Dean smirked.

‘Okay princess. We’ll find a good one. I should probably get changed first though, they don’t normally let people into those places wearing jeans.’

Castiel frowned. He’d been correct in assuming Dean would make note of attire. But, he speculated, at least Dean seemed enthusiastic about trying it, rather than complaining about dressing nicely. Maybe there was hope for the things Castiel wanted yet. He just had to keep trying to make it sound like this was all Dean’s idea, to keep him compliant.

‘We should go shopping. You could probably do with a better outfit. You look like you’re going to check their receipts.’

Castiel didn’t understand what Dean was implying, but he liked the idea of shopping with Dean, though he’d never experienced retail before.

‘As you wish,’ Castiel smiled. He caught the moment that Dean shook his head, smiling to himself.

Dean pulled smoothly into an out-of-town shopping mall, and looked at Castiel appraisingly.

‘So, I’m going to guess you have no idea what you wanna wear, right?’ Dean smirked. ‘We’ll do a deal, I pick an entire outfit for you, you pick one for me. Right?’

Castiel grinned back, already trying to picture how he’d like Dean to look on their date. For some reason, he settled on a scene he’d seen in another movie, of a one piece in a rather hideous green, that stretched from the shoulders to the crotch. Castiel hadn’t understood much of the movie, but he had liked that scene when he imagined Dean in that outfit. Surely they’d have some at the mall?

He followed Dean into the building, letting Dean take charge once again as he headed towards a store crowded with denim and plaid shirts like Sam favoured. Castiel tried to swallow down his displeasure at being in the store. Dean wasn’t going to dress him like Sam, was he? They’d broken down some boundaries, making out heavily in the Impala. Dressing like Sam, Castiel felt, would be a huge step back.

‘Dean, we’re going to a nice bar, aren’t we?’ Castiel said in a quiet voice, trying to slip his hand into Dean’s. Dean pulled his hand away as soon as he felt Castiel’s fingers graze his palm.

‘Yeah, sure,’ he looked at Castiel, and sighed. ‘Okay, nothing like this stuff?’

Castiel shook his head, and Dean shrugged, turning on his heel and heading straight back out of the store, Castiel hurrying to keep up. They approached a large department store and headed over to the men’s section, where a cheerful sales girl started chattering away to Castiel.

‘Hello, can I help you with anything today?’ She beamed. Castiel eyed her warily, before glancing up at Dean. Dean merely shrugged, and thumbed through a nearby pile of polo shirts.

‘Um, yes. My-my friend and I,’ Castiel was careful to not name Dean as his date. ‘We’re going to a bar. A nice one. I have to pick an outfit out for him. What do you suggest?’

Dean raised an eyebrow at Castiel, and Castiel knew he was silently being accused of cheating at the game. The girl looked at Dean, and her eyes bugged open wide.

‘Oooooh, well,’ the girl began babbling too fast for Castiel to keep up. He stopped paying attention, too caught up with how Dean had begun to smirk, watching this thin girl over-gesturing as she described … whatever it was about clothes that had made her talk so enthusiastically. Dean winked at him, and he could practically hear Dean teasing him for trying to cheat.

‘Thank you, I’ll keep that in mind,’ Castiel blurted out as the girl took a breath, and hurried into the next section, Dean openly laughing behind him as he followed.

‘Wanna start again?’ Dean asked, still laughing in short bursts, as though he kept finding new things to be amused at. Castiel stopped at a display of button-down shirts, and pulled a soft grey one from the pile.

‘It’s fine, Dean. I think I can work it out.’

‘Uh huh, it’s only pants, a shirt, maybe a jacket. And shoes. Not rocket science.’

Castiel nodded, crossing the floor to grab some blue dress trousers and a navy jacket, and at the last minute, grabbing a cravat from a display, before passing them over to Dean.


Dean looked at the pile, his nose wrinkling at the cravat, a black-and-white patterned silk thing, but then looked back at Castiel, his expression softening.

‘Fine, I’ll try them once I’ve picked something out for you.’


Dean had insisted that Castiel stay put as he walked around picking out clothes. Castiel had no idea what Dean would be thinking, whether his reaction to the cravat would be a way for him to seek revenge or whether he’d want to show Castiel off. But it had been fine, Dean had returned with some tan slacks, a white shirt, and a blue sweater, before he pulled Castiel into a nearby changing room. And then he had undressed Castiel, his fingers moving quickly as he unbuttoned Castiel’s shirt and pushed it off, exposing Castiel’s chest and causing goosebumps to erupt all over his body. It was only when Castiel was stood in the small cubicle, in white boxer-briefs and his black socks that Dean looked up at his face, and saw the lustful gaze that Castiel had been shooting him.

‘Dude, we’re in public.’ He whispered, and leaned closer, making sure that only Castiel would be able to hear. ‘Did you not get enough in the car?’

Castiel shook his head. How could there ever be enough Dean? But he had passed Castiel the outfit, and turned around to change himself, keeping enough distance that they couldn’t graze against each other. Castiel had reluctantly put the outfit on that Dean had given him, and looked over at Dean again as he straightened out the jacket he was wearing. Castiel fell in love all over again, or still, or harder, or whichever phrase was technically correct for the searing pain in his head and the rush of heat to his abdomen. Dean looked so good in the clean lines and soft colours, and Castiel fought the urge to reach over and run his fingers through Dean’s short hair, to trace Dean’s jawline with his fingertips, to kiss every millimetre of skin he could find. Dean caught his eye in the mirror and smiled weakly.

‘We’re not going to spend time with any pretentious douchebags, are we?’

Castiel shook his head, glad that Dean would be so against interacting with other people in the bar. That meant more focus on Castiel. That meant more intimacy, more Dean, more togetherness.

Dean had managed to convince the chatty salesgirl to ring their outfits up while they were still wearing them, placing Castiel’s suit and trench coat, and Dean’s worn jeans and sweatshirt into one of their waxed paper bags, gabbling incessantly at both men. Dean smiled and nodded and responded with short answers, trying to escape the store. He looked annoyed as he headed to the car, and Castiel watched him they walked. What had suddenly turned Dean’s mood sour? Was it just the shop assistant? Dean drove back towards the motel, and just as Castiel began to have misgivings, Dean pulled the car over, onto a derelict road.

‘Okay. Okay,’ he seemed to be steeling himself for what he was about to say. ‘Okay, Cas, I know I said I’d agree to this date, and today’s been … well, it’s been way more fun than I thought it was going to be so far. But can we have some ground rules for the bar? Like, no touching, no kissing, no nothing in public. Right?’

‘Are you ashamed of me, Dean?’ Castiel asked softly, his eyes darting away from the hunter for the first time in weeks. He didn’t want to see the look of regret on Dean’s face.

‘What? No. No Cas. I just don’t want any trouble, okay? And it’d be great if we could just enjoy a date together, but I don’t wanna have to deal with idiots who can’t … who don’t … just trust me on this.’

‘This isn’t about the sales assistant, is it?’

‘Cas,’ Dean slid his palm up, against Castiel’s jawline, cupping his face, the warmth of his palm making Castiel’s heart flutter. He stroked his thumb gently across Castiel’s cheekbone, until Castiel looked back up at him. ‘She was annoying as hell. But it’s nothing to do with her. It is about the eye sex in the changing room. It was barely okay there.’

Castiel looked at him, at those familiar moss-green eyes with golden flecks, at the soul peeking its way out of the deep, dark irises to grab Castiel right in the core of his being. Not his vessel, his very essence. Dean stared back, for an infinite amount of time, it seemed.

‘This is what I mean by eye sex,’ Dean eventually spoke again, his voice cracking as he did.

‘You’re not looking away,’ Castiel pointed out. Dean bit back a smile, which softened his features and made him look ten years younger. Humans had that knack.

‘I didn’t say I wanted to,’ Dean pointed out simply, and turned his head to look around, outside the car. Noticing how barren the world looked at that moment, he turned back and caught Castiel’s lips softly with his own, moving slowly, tenderly, and Castiel felt his insides warming up, melting into a puddle within the structure of his skin. Dean resisted Castiel’s attempts to slip his tongue into his mouth, and pulled away far too quickly for Castiel’s liking. ‘Come on, the shop girl at least knew where the kind of bar you’d like would be.’

He sat around again, starting up the car and pulling out smoothly onto the road again, concentrating on driving as Castiel concentrated on him, on the man who set his heart fluttering erratically just by being in close proximity. Dean didn’t look at Castiel again until he parked up outside a stark-looking building, all white stucco walls and nondescript panelled windows towards the ceiling.

‘Was she sure that we were aiming for this bar?’ Castiel asked dubiously. Dean laughed, shaking his head and gripping the steering wheel.

‘Oh, Cas, trust me, they spend the money on the inside. Come on.’ Dean climbed out of the car swiftly, waiting around the front of the car for Castiel to get out, and walk beside him into the bar.

‘How about I grab us some beer and you go grab us a table?’ Dean suggested, striding slightly ahead of Castiel and leaning against the bar, which Castiel noted was lit on the top by fluorescent bar lights. The entire lighting scheme in the bar seemed out of the norm, most of the light source coming from the bar or the individual table tops. He felt disoriented, and followed Dean to the bar, standing close beside him. Dean cast a glance behind them.

‘Dude, half the tables are empty.’

‘I’m not sure I’m going to like this bar,’ Castiel decided. ‘I don’t understand it.’

Dean sighed, holding up two fingers to the bar girl as she caught his eye.

‘Look man, I’m trying something very new for you, and I’m pleasantly surprised by it. So deal, we’re staying here now. Especially now our beers are in.’ He nodded at the bar girl, who had put the bottles on the table, and accepted the twenty he slid her way. And then Castiel found Dean waving a beer bottle in his face, grinning slightly, before he accepted his change and led the way to one of the tiny tables. Castiel sat on the seat opposite Dean apprehensively, feeling slightly better when he felt Dean’s knee graze against his leg. At least this bar had that going for it, the compromising personal space that came from too-small tables, designed purely to hold a few glasses of alcohol. Dean sat forward, leaning his head towards Castiel’s.

‘So, wanna talk about anything in particular? Or just coffee?’

‘Tell me things from your childhood.’ Castiel decided. Dean smirked, playing with a coaster.

‘Geez Cas, didn’t you see it all?’

‘I didn’t know to look for you then. I wish I had.’

‘Mmm, way to make it creepy,’ Dean grinned before placing his lips around the bottle neck, tongue in place before he tipped the bottle back. Castiel felt his penis twitch just from that small act. How was he supposed to act like he wasn’t on a date with Dean when he drank his beer the way he did? How was he supposed to resist taking the drink out of Dean’s grip and slide himself onto Dean’s lap, holding the hunter’s head between two gentle hands and kiss him in front of everyone?

Before Dean could start reminiscing, or changing the subject, before Castiel managed to erase the fantasy from his mind, two girls approached them, giggling incessantly. Castiel would not even have noticed, if Dean hadn’t looked up, removing the bottle from his mouth and smiling innocently. That smile was meant to be Castiel’s smile.

‘Hello,’ Dean nodded at them. Castiel turned and looked them over quickly. Both were thin girls, dressed inappropriately in short skirts and tube tops, their faces overly made up and hair coiffed to near stiffness. He turned back to face Dean without acknowledging them further.

‘Hi, so, me and my friend have a bet?’ One girl giggled, stepping forward and sliding onto Dean’s knee herself. Castiel couldn’t place the emotion that small action sparked, but he knew that, if the room wasn’t rapidly filling up, he would have stuck his angel blade right into her heart. Dean was his. ‘That you and your friend would buy us a drink?’

Why did this girl pose everything she said like a question? Castiel found the habit frustrating. Dean met his eye, fighting a smirk with humour dancing in his eyes. Castiel recognised the look, it was similar to the time that Dean had dragged him into a strip club. Castiel had managed to ruin that trip also, and luckily Dean had seen the humour in it. Maybe this situation was so similar that it had triggered a memory for Dean also, and that was what the smirk was about?

‘Why would we do that?’ Dean asked, still fighting the smile, as the girl slid her arms around Dean’s neck.

‘Because you’re good guys,’ the girl breathed, and leaned closer to Dean, her eyes sliding shut and her mouth puckering forward and-

Castiel was out of his seat before he knew it, heading for the exit of the bar. So much for their intimacy. Was this technically Dean cheating on him? And had the friend been trying to flirt with Castiel? As he hit the sidewalk, he realised he had heard a shriek, and someone behind him had hampered his progress out of the bar, for a moment anyway. He felt guilt for a short moment, before his frustration and anger and betrayal took over. This was his date with Dean! Who did that girl think she was? She didn’t ask Dean’s permission to touch him, she just dived in, immediately getting the kind of tenderness from Dean that Castiel could only dream of-

‘Hey! HEY! CAS!’ Dean was practically screaming behind him. And then, slightly closer. ‘Son of a - what the hell was that?’

‘She was going to kiss you,’ Castiel told the sidewalk as he continued walking.

‘Oh my God, Cas! She was a skank, trying to get wasted for free. Hey, look at me!’ Dean grabbed at Castiel’s arm, pulling him around to face Dean. ‘I didn’t forget that we’re on a date. I was trying to find the point to let her down gently, okay?’

Dean’s voice was softer, but he made no effort to comfort Castiel, to stroke his arm or pull him into a hug or anything Castiel would have wanted. Because for Dean, it was easier to flirt with the skank at the bar than it was to be vulnerable with Castiel. And Castiel hated that feeling, that he was somehow second best to someone they had barely met when Dean meant so much.

‘Cas, trust me, nothing was going to happen. Nothing. Not after- not after this morning man. But check it, Cas, if you’re serious about us being a thing, about you wanting this? You trust me. Because if you don’t, we have no chance, whatsoever. So trust me, and be patient, and let me do what I need to because I’m freaking human, okay?’

Castiel nodded, and forced himself to smile, to look into Dean’s eyes as though he had nothing to hide.

‘You’re right Dean. I didn’t trust that woman, that’s all. Did you want to go back in there?’

Dean shook his head.

‘Nah, we’re good. Besides, I think you’d get arrested if you walked back in, you busted that girl’s nose up pretty well. I didn’t get jealous over that, by the way.’

‘You know I only have eyes for you,’ Castiel breathed. Dean laughed.

‘Yeah, I know. Look, let’s just call it a night, and we’ll do something better tomorrow, okay? Promise.’

And then, shocking Castiel completely, Dean reached closer and gave him a swift kiss on the lips, before heading back to the Impala. Castiel traced a finger where Dean’s lips had just been, feeling conflicted. In so many ways, it would be awful to wipe Dean’s memory of this day. But Castiel had made the decision, and he was sticking to it.

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