Fifty First Dates

Chapter 2

Castiel had thought long and hard about the best date to begin with. Even if he planned to make Dean forget every date in order to have a new first one, he wanted to ease Dean into the idea of dating him, and that meant beginning in Dean’s comfort zone.

For example, Castiel had once seen a film about two cartoon dogs who shared a plate of spaghetti, and although he didn’t fully appreciate the concept of dining in an alleyway - that was the first place you were likely to stumble upon something demonic - he did like the notion of the intimacy that would come from sitting across a table with Dean, the only real source of light coming from a slowly melting candle perched on the linen covering the small plinth of wood that separated them. It wouldn’t entirely separate them, of course, because the table would be so small, that by drawing their chairs in close enough to eat, their legs would touch, would graze against each other, and although Castiel would have no need to share Dean’s meal, he could still experience some of the heightened emotions by knowing Dean’s body was pressed close to his. Castiel dreamed of that date, the one with fine dining and intimacy and a sense that only they existed on the planet. But he knew how uncomfortable Dean would find it. It wouldn’t be the prospect of being so close to Castiel, or the type of food, but the expectation that Dean would feel was placed upon him by others. He would feel something as arbitrary as his clothes separated him from the other diners, lowering his worth as compared to theirs. He would be self-conscious as he ate, misjudging which piece of silverware to use, refusing to handle his wine glass for fear his grip would be either too firm or too clumsy. And Castiel would wish to tell him that there was no need for the reservation, that the other diners should feel honoured to be in the presence of the man who tirelessly worked to save their lives over and over. But that would not matter to Dean, because that is his job and this is etiquette and Castiel would struggle with the implications of human interactions all over again.

It took him a few weeks to find the perfect first-first date with Dean. They were separated temporarily, as the Winchester’s hunted a djinn and Castiel met with a few of his angelic brothers, who were discussing new Heavenly strategems. The meeting, Castiel felt, had gone well and he had contributed to a worthy cause, as the other angels present embraced humanity much the same way he did. He had been returning to Dean’s side, when he passed a sign that caught his eye. Two men wore camouflage and face masks, wielding unusual-looking guns. The words screamed “Paintball!” and Castiel knew that Dean would find the activity humorous.

He had hurried to Dean’s side, but unfortunately, Dean and Sam were in a diner, tucking into their meals of a burger and salad respectively. He couldn’t materialise in front of the other patrons of the diner, and couldn’t discuss the date in front of Sam. He had understood the subtext enough to know that Dean did not wish to share the news with Sam, that he had agreed to this date with Castiel. So Castiel remained invisible and silent in the diner, listening to them discussing a recent baseball game they had witnessed. The anticipation of seeing Dean’s face as Castiel revealed the date was hard for the angel to deal with, but somehow he resisted the temptation until the boys had left the diner, and Sam was making a phone call while Dean climbed into the Impala. Castiel “appeared” in the backseat.

‘Hey, Cas,’ Dean looked at him in the rearview mirror. ‘How’s it going?’



‘Our date. We should participate in paintball.’

‘I don’t know Cas, it’s meant to be a team effort. It’s not really a date thing.’

‘Oh. I thought you’d be interested. You could shoot things and no one would die.’

Dean chuckled.

‘Okay, fine, Cas, we’ll paintball. Just you and me.’

Castiel beamed at Dean, as Sam slid into the passenger seat, simultaneously putting his phone into his pocket. Sam seemed oblivious to the atmosphere that was developing between Dean and Castiel as he settled in his seat.

‘Hey, what’re you guys talking about?’

‘Cas wants to try paintball. I figure, we’re done with the djinn, why not?’

‘Oh, cool, I’ll book us in somewhere. Great idea, Cas!’ Sam turned and beamed at the angel, who levelled him with a dirty stare back.

‘Uh, I think Cas booked something already, right, Cas? And there were only two slots going.’

‘What?’ Sam complained. ‘Who did you go with, Cas? I’ll call and try and get a third.’

‘Sammy, suck it up, maybe next time,’ Dean patted his arm playfully, winking at Castiel in the mirror.

‘Well, why do you automatically get the second ticket?’

‘Because Cas likes me more. Don’t worry Sam, we’ll drop you at the hotel, you can watch porn or whatever, and I’ll show our good angel buddy how to pulverise nerds with paint pellets.’

Sam sighed, and leaned back in his seat as Dean headed back to their motel. The drive was short, and Dean didn’t even turn off the engine outside of the motel, letting it idle as he looked expectantly at Sam.

‘Bye, then.’

‘Thanks Dean, really, way to make me feel unwanted.’

Dean shrugged.

‘You are unwanted right now. We’ll see you later, okay?’ Dean looked in the rearview mirror again. ‘Cas? You coming up front?’

Sam rolled his eyes and climbed out of the Impala, slamming the door with unnecessary force as he stalked away. Castiel flashed into the front seat, and Dean pulled away.

‘So, where’s this paintballing gig?’ Dean asked as he hit the local highway.

‘Not too far. I didn’t realise you meant right now, Dean.’

‘Why not? Case is over, you had an idea for our date. What’s to wait for?’

Castiel hadn’t banked on Dean’s impulsiveness, his spontaneity.

‘Nothing, I just didn’t realise that it would be a case of me sharing an idea and we would instantly do it.’

Dean smiled.

‘We’ve been talking about this long enough Cas. It’s about damn time, huh?’

As crudely as Dean had expressed the sentiment, Castiel had to agree that it had taken an awfully long time from when they had first discussed coffee until they reached this point. Dean fell silent as he drove, looking for an area that seemed likely for a paintball game, and Castiel took to watching Dean’s hands as they gripped the wheel, caressing the leather covering as he turned the car, the way a muscle moved at the back of his cheek when he swallowed, how delicate Dean’s eyes looked when he blinked, the long eyelashes fluttering down over his look of stern concentration.

Castiel loved that contradiction in Dean, the tough exterior, the hardened expressions, all of which would melt away in a moment if you looked at him in the right way, or if Dean felt empathetic to your situation. And he believed strongly in paying his dues. Castiel loved nothing more than the fact that Dean took promises seriously, and worked hard to protect those who helped him. Like he had when they had first met. They would never have bonded if Dean hadn’t felt some gratitude for Castiel pulling him out of the pit. But, Castiel reflected, if that wasn’t Dean’s attitude, he would never have been assigned the job of saving Dean’s soul. To Castiel, the very fact there was no way they wouldn’t have bonded was evidence that he was meant to be with Dean, on any and all levels.

‘Here we go. Are you ready?’

‘No, but I know you’ll enjoy it.’

Dean smiled, and placed a hand on Castiel’s shoulder, squeezing it slightly and rubbing.

‘You will too, Cas. Come on, we’d better get in there before all the good pellets are taken.’

‘I may need you to explain the rules. I only said because the pictures-‘

‘It’ll be fine, Cas. Come on.’

Dean climbed out of the Impala, turning to look at Castiel, who had flashed out of the car and stood behind him. Castiel heard Dean chuckling as he locked up the car and turned around to face the angel.

‘Maybe you shouldn’t use your angel powers for the game. Might be an unfair advantage.’

‘You have the advantage of knowing how to shoot.’

Dean’s eyes flickered over Castiel’s face, the smile set into his face as he nodded towards a slightly ramshackle building set within a sprawling tree line.

‘We need to go in there, right?’

Castiel nodded, letting Dean take charge as they entered the building, paid for their attendance, and listened to the safety lecture that the paintball company insisted they needed to listen to. Castiel found their speech dull and confusing, and he spent most of the twenty minute presentation watching Dean’s reactions as Dean smirked and snorted with soft laughter, obviously getting more out of the situation than Castiel was. Castiel wanted to reach over, to plant a soft kiss on the slight dimple on Dean’s face, to thread his fingers with Dean’s and lean against the strong, solid hunter. But the room was full of various other men, most of whom carried themselves the way Dean did, with that air of confidence and independence and a slight arrogance that altered their stances slightly. As much as this was an activity that Dean would enjoy, Castiel was beginning to regret his decision to make this their first date. There was no chance of the intimacy that Castiel had desired, not when he was being handed a plastic gun full of tiny, multi-coloured beads, and marched outside into the woodland, where Dean took charge of the group they were part of, which included four men Castiel had never seen in his life. Dean began talking of strategy and strengths, checking what the other team members were able to do and planning the best way for them to win their current game.

And Castiel fell in love with Dean all over again, watching the way his mouth formed the words, listening to the deep timbre of Dean’s voice, the stern infliction as Dean enforced his authority, the kind words he used to motivate the team. Dean was in his element, doing what he did best, and Castiel was in awe once more of the human he was fortunate enough to at least consider a friend, and amazed that Dean had agreed to this date. So Castiel swallowed his disappointment down, and listened to Dean’s instructions as well as he could. He finished up quickly, and the rest of the team split up, missing the moment when Dean grabbed Castiel’s shoulder, and pulled him into a nearby hut, seemingly oblivious to the way Castiel’s skin erupted at the touch, burning and tingly and taking all his attention.

‘You’re keeping hold of the flag, okay? I’m covering you, the guys are the offence,’ Dean muttered. Castiel nodded, relieved that Dean was recapping for his benefit, and that he wouldn’t be too far away. ‘You’ll need to watch for me too, okay? In case someone sneaks up on me. Remember what they said about how to use the gun?’

Castiel nodded, and Dean smirked, squeezing his fingers on Castiel’s arms and leaning closer, placing his head beside Castiel’s, their skin nearly touching and the proximity of Dean sending Castiel’s system into overdrive. The sensation of Dean being so close, but not making contact was somehow more intoxicating than if they were doing exactly as Castiel wanted, and were pressed flush against one another, leaning heavily against the wooden hut, Dean’s lips and tongue and teeth attacking Castiel’s face in a bout of heated passion as their hands stroked and grabbed and rubbed and caressed every inch of each others torsos, their bodies chest-to-chest, stomach to stomach, groins pressing against each other, restricted by their clothes …

He made himself concentrate as Dean whispered in his ear, Dean’s very breath warming Castiel’s cheek and sending shivers down his spine.

‘Don’t think I don’t realise you’re undressing me with your eyes. Focus, okay Cas?’

‘Well, we are on a date.’ Castiel replied throatily. Dean laughed softly.

‘We are. I haven’t forgotten. Just take it easy, okay Cas?’

What Castiel would have liked to have happen next was for Dean to kiss the spot he’d been breathing on, or to maybe bite gently on his ear lobe, or to pull back slightly and press his lips on Castiel’s, aiming for a gentle kiss and being pleasantly surprised when Castiel unleashed the passion that he learned from the pizza man on him.

Instead, Dean gave him a one-armed hug, patting his back a couple of times before stepping away, peering out through a gap in the hut’s doorway. Castiel stared at the hunter’s back, his mind still reeling as he debated the things he should have done to lengthen the hug, to turn it into something else vaguely romantic.

‘Don’t think I can’t tell you’re picturing us having sex, Cas,’ Dean whispered from the doorway.

‘I wasn’t,’ Castiel lied. Dean chuckled, holding the paint gun up to his shoulder, pointing it through the small crack of the doorframe.

‘Sure you weren’t. You keep trying to have eye sex with me.’


‘If I wasn’t okay with it, Cas, I wouldn’t be here right now. But there’s time for that, right now, we should focus. You got the flag?’



Paintball, Castiel realised, was a long activity, one that took most of the day. Dean had single-handedly taken out three of the other team protecting Castiel, and Castiel had imagined Dean as his knight in shining armour, his protector, when normally it felt like Castiel was the one saving Dean. The reversed roles felt good to Castiel, as though it put them on a more even footing.

Everyone stopped before it grew dark, and Castiel stood slightly off to the side as Dean laughed with the other team mates and exchanged numbers, agreeing that, if he and Castiel were ever in the area, they would love to be part of the team again. Castiel stood beside the Impala, watching as Dean talked, and listened patiently, ducking his head so he was on a similar level to the men who weren’t as tall as he was. Dean looked so comfortable talking to other humans, even after he had pummelled them with paint pellets for most of the afternoon. Castiel had taken a few to the stomach and thighs during the games, and he knew that if he were a human, his skin would be marred by the black, blue, purple, green and yellow hues of various bruises before too long. He wondered, as Dean clapped one guy on the back and shook his hand, whether Dean’s skin would be covered in the same way. He made a mental note to kiss each and every one before healing Dean completely.

Dean jogged back to him, smiling widely.

‘Wanna go grab a beer? Celebrate all the wins?’ He stopped just out of Castiel’s reach.

‘I- yes, that sounds good.’ Castiel said stiffly. Dean frowned at him momentarily.

‘You okay there, Cas?’

What Castiel wanted to say is that he was dying for some physical interaction, for Dean to respond to what he had referred to earlier as Castiel’s “eye sex” and push him up against the Impala, mouth pushing down on Castiel’s, tongue forcing its way roughly into Castiel’s mouth, his fragile human lungs burning as he learned to balance his breathing with their connection, his legs shaking with the effort of standing up when Dean was pressed so close to him. But he knew that as soon as he put the words out there that Dean would clam up, avoid the issue, and refuse to ever try this again.

‘I’m fine Dean. You enjoy beer, so we should go and get a beer.’

Dean folded his arms, staring at the angel, one eyebrow cocked.

‘Okay, drop the bullshit, Cas,’ Dean looked over his shoulder, as everyone else was driving away, leaving them alone in the makeshift car park. He turned back to Castiel. ‘You don’t want to grab a beer, clearly. What do you want to do? This is your date, too.’

‘I want to make you happy, Dean.’

Dean sighed.

‘Get in the car, Cas.’

Castiel zapped himself into the passenger seat of the Impala as Dean unlocked his door, climbing into the driver’s side, and in one fluid motion, leaned across and kissed Castiel. It wasn’t any of the passionate explosions of feral emotion that Castiel had been expecting, but a chaste kiss, lips pressed together for a few moments. Castiel reflected on the softness of Dean’s lips, the bottom one slightly more moist than the other, as Dean had a penchant for licking his lower lip often. A small crack in one corner, the top layer of skin coming away slightly, feeling rough against Castiel’s mouth. A hint of Dean’s breath on Castiel’s tongue, a slightly sour note from long exposure to alcohol that was surprisingly pleasant. Dean’s hand on the back of Castiel’s neck, gentle yet firm, his fingers working the short bristles for the brief moment their mouths were connected, almost massaging the back of Castiel’s neck. Castiel’s eyes closed as Dean’s fingers brushed across his skin, and remained closed as Dean pulled away and chuckled softly to himself again. Castiel didn’t care, he was instantly replaying the moment, over and over, in his head.


‘I love you, Dean.’

The silence that followed Castiel’s declaration was charged with a tension that Castiel didn’t understand. He opened his eyes slowly, and saw Dean looking down at the steering wheel, the tick in his cheek flickering again.

‘We should go back,’ Dean decided eventually, and Castiel cursed himself for changing the mood. How had telling Dean that he loved him - which, surely, Dean knew already? - made Dean feel like he should call an end to their evening? They drove in silence back to their motel.

As Dean parked up, he looked over at Castiel, his jaw tensing as though he had something to say, and Castiel looked back, worried about what Dean could possibly say.

‘So, paintball was fun. Thanks, Cas.’

‘It’s okay,’ Castiel said quietly.

‘It was a good date. Beat some I’ve been on.’

‘That’s good. That’s what I wanted.’

Dean was staring hard at him, and Castiel couldn’t take it any further, turning his head and staring at his knee, as though the grey slacks he wore would be able to quash how uncomfortable he felt.



‘Are you-‘

‘We should go and see Sam.’ Castiel announced quickly, and zapped out of the car, straight into the motel room, where Sam was kicking back on his bed, watching something on his laptop.

‘Hey, Cas, is Dean with you?’ Sam asked without removing his eyes from the screen.

‘I believe Dean will be here shortly, he was just parking the car.’

Sam nodded, still staring at the laptop, and Castiel stood to the side awkwardly, listening for Dean’s footsteps outside. It seemed to take an age, but was really about ten minutes, before Dean finally stomped along, and pushed his way into the room, his eyes automatically latching onto Castiel. He looked frustrated, or angry - Castiel didn’t have enough experience with telling the two apart where Dean was concerned - but before they could say anything to each other, Sam was speaking up, still staring at his laptop.

‘Did you eat already? I was thinking about ordering some pizza in.’

‘Sounds good,’ Dean said stiffly, glaring at Castiel as he slouched over to the small table and sat heavily in one of the plastic chairs, folding his arms and leaning onto the table. Castiel didn’t understand Dean’s body language, at all, and he knew Dean wouldn’t explain anything with Sam in the room, not really. Castiel was going to have to bide his time and put up, for now, with Dean’s tantrum, before he got to wipe Dean’s memory of the date from his mind. He was glad he’d decided to do that, because there was clearly no way Dean would want to date him again otherwise.

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