Fifty First Dates

Chapter 7

Castiel felt a heavy burden after wiping Dean’s memory of the past two days. Though he had convinced himself that it was the right thing to do, the best way to save his position in Heaven and Dean’s soul, it didn’t mean he was happy about it. He could still sense the ghost of Dean’s fingers on his skin, tracing a pattern through Castiel’s shirt. He’d felt them all night.

Castiel watched over Dean throughout the night again, wishing he could just lay with Dean, cuddling close and brushing kisses over Dean’s skin while Dean rested. But Castiel knew he couldn’t do that, not when Dean was unaware of their previous dates. Instead, Castiel stood in the corner of the room, watching as Dean shifted restlessly in the bed, tangling the sheets around his legs and exposing his firm chest throughout the night. Castiel was sure to leave the room before Dean woke up, to avoid any awkward questions from the hunter. He walked the hallways of the bunker aimlessly instead, replaying memories of the past few days in his head, of every kiss, every touch, and the look in Dean’s eyes throughout. He was almost convinced that Dean felt the same way, but Dean hadn’t said anything to indicate that he did.

Eventually, Castiel wandered into the kitchen, where Dean and Sam were now both awake, coffee cups half used on the table and a strange tension emanating between them. Dean was giving Sam a hard stare, and Sam’s eyes flickered to Castiel, his brow lowering slightly before he looked back at Dean.

‘Well, anyway. We should go,’ Sam addressed Dean. Dean rolled his eyes, and slurped at his coffee.

‘Sure, I’ll prove you wrong. Cas? Sam thinks we should go to a carnival that’s happening “tonight”, want to come?’

Dean had raised his hand and flicked two fingers up and down as he said the word “tonight”, his voice oozing sarcasm. Castiel missed the significance of Dean’s irritation, and instead focused on the fact that Dean was asking him out. Dean was asking him out, wasn’t he?

‘That sounds wonderful, Dean.’

Dean looked up at the angel, and Castiel smiled back. Sam coughed, and stood up.

‘I’m going to scan online for any more cases. Maybe tomorrow we can get back to work?’

Sam left the room, and Castiel took his vacated seat, across from Dean. Dean was staring at the newspaper Sam had left on the table.

‘Is everything okay, Dean?’

‘Mmm, yeah, sure. Sam’s full of shit, that’s all.’

Castiel wanted Dean to continue talking, to open up to Castiel on what Sam had done to irritate him this time, but he knew he had to tread carefully. They were back to the beginning, after all, and Dean wasn’t going to be as open with him as Castiel would have wanted.

‘So, this carnival visit, is this going to be our date?’

Dean snorted with brief laughter, and finally made real eye contact with Castiel.

‘Sam’ll be there. And there won’t be a carnival.’

Dean sounded so sure as he spoke, and Castiel slumped in the seat. Why was this becoming so hard to do? Dating Dean was meant to be easy.

‘Hey, Cas, it’ll be okay. We’ll do something tomorrow, maybe? Or how about this, if Sam isn’t being the biggest dick on the planet right now, and there is a carnival? We try and ditch him on a ride and make it our date.’

‘Are you sure?’ Castiel tried to make it sound as though he wasn’t bothered.

‘Cas, I wasn’t … this isn’t about us dating, okay? I don’t think the carnival really exists. If I’m wrong,’ he frowned, like the concept was impossible, ‘then we’ll make it about us. It’s just Sam being Sam. It’s not you.’

Dean reached across the table, taking Castiel’s hand and rubbing his thumb across Castiel’s knuckles, the dry skin of his fingertips scratching slightly at Castiel’s unblemished hands. Castiel felt reassured, not by Dean’s words but by his touch. All he wanted was to walk around the table, slide onto Dean’s lap and melt into him the way they had been doing the last couple of days. He caught Dean’s eye again, and Dean swallowed, his Adam’s apple bobbing up and down. Could Dean sense the way Castiel was feeling?

‘Hey, so um, we’ll probably head out in a couple of hours,’ Dean sounded flustered. He opened his mouth to continue speaking, but after opening and closing his mouth a few times, it became clear that he wasn’t going to finish his thought. Castiel squeezed Dean’s fingers gently, forcing himself not to crawl across the table to get to Dean. How could he look even more enticing when he was so uncomfortable? He grabbed his coffee instead, draining the mug and standing, letting go of Castiel’s hand to take his and Sam’s mugs to the sink, washing up. Castiel found his attention drawn to Dean’s ass, at the taut muscles and the smooth curves, and he looked without shame as Dean cleaned up. When Dean turned around, drying his hands on a dish towel, Castiel took a moment to raise his eyes up to Dean’s face. Dean cocked an eyebrow, and put the dish towel to the side of the sink.

‘Cas, last time someone looked at me like that, I got laid,’ Dean was teasing, Castiel guessed. It wasn’t the first time Dean had said something like that to him, although this time it was probably more accurate. Dean crossed the room again, stopping and stooping down to whisper in Castiel’s ear. ‘How about when we see that the carnival’s a figment of Sam’s imagination we ditch him anyway and have that date?’

Castiel closed his eyes, breathing in Dean’s scent, his heart thudding in his chest, his entire body almost humming from the increased heart rate.

‘Is that what you want, Dean?’

Dean didn’t say anything back, his response was to press his lips against Castiel’s forehead, his fingertips catching at Castiel’s face, holding him gently as Dean’s lips travelled down the angel’s face. Castiel’s chest felt ready to burst. This was what he wanted, so much, to feel that Dean cared as much as he did.

‘Does that answer your question?’ Dean asked after brushing his lips against Castiel’s mouth. Castiel was shaking with desire, and he reached up, clinging onto Dean’s muscular shoulders, pulling him back down, crashing their mouths together. Dean kissed back with enthusiasm, as though his bad mood was lifting just from his contact with Castiel. Was that possible? Could Castiel really have influenced Dean’s mood that much? Dean sank onto Castiel, straddling him in the chair, his groin pushing into Castiel, his entire body warm against the angel, who embraced Dean’s weight upon him. And Castiel pulled at Dean’s shoulders, pulling him closer so that they were pressed tightly against each other. Dean groaned, and held the back of Castiel’s head firmly, tilting it back slightly so he could make the kiss deeper, his tongue flicking around Castiel’s mouth in earnest. Castiel responded with equal enthusiasm, smiling into the kiss.

They didn’t hear Sam walk back into the room, sigh, and cross the room to the sink. They only heard him as he banged a pot down, the metallic ring echoing around the room. Dean pulled away from Castiel to shoot an annoyed glare at his brother.

‘Come on, Dean. The carnival’s a few hours away.’ Sam’s eyes flickered to Castiel, and then back to his brother. ‘Maybe lend Cas some clothes. Who wears a suit and a trench coat to a carnival?’

Sam left the room again, and Dean peeled himself off of Castiel reluctantly, Castiel’s body tingling with cold wherever they had made contact.

‘He’s a bitch, but he has a point. We’ll finish this off later, okay?’ he ran a finger across Castiel’s lips, and Castiel nodded silently. Dean smirked, and grabbed Castiel’s tie, tugging him off of the chair, out of the kitchen and into his bedroom. He rummaged through his closet, and pulled out some jeans and a loose-fitting top, passing them to Castiel and planting another kiss on his mouth.

‘Get dressed, we’re going soon. I think I have some sneakers somewhere you can use as well.’ He looked at Castiel and sighed. ‘Don’t give me that look.’

He left the room, and Castiel clutched Dean’s clothes, wondering what look he had been giving Dean and why he didn’t seem to want it when everything seemed to be going so well. If Castiel didn’t know any better, he’d be convinced that he hadn’t managed to remove Dean’s memories at all. He changed into Dean’s clothes swiftly, with a hopeful feeling brewing in his chest as he breathed in Dean’s scent as it clung to the clothes.


The drive to the temporary fairground was long and uncomfortable. Castiel was made to sit in the back, and he could sense the angry tension between the Winchesters. He had no idea what they were arguing about this time, and had no desire to know past how it affected Dean. Surely, Sam was in the wrong, with whatever situation had arisen? And surely Dean would let him take some of the tension away by progressing with their physical relationship?

Dean finally turned into a field that had been converted into a temporary car park, the carnival already in full swing in the adjoining field. Sam gestured towards the Ferris wheel in the distance.


Dean shot his brother an annoyed glance, and climbed out of the car, knocking on the back window to signal that Castiel should come out. He did so slowly, as Sam strode on ahead.

‘Is everything okay, Dean?’ Castiel asked quietly.

‘Yeah, don’t worry about it. Come on, I wanna feed you up on carny food and then watch you puke on the Helter Skelter.’

Castiel frowned at the unromantic nature of Dean’s proposition.

‘I thought this was a date?’

Dean smiled, and threw his arm around Castiel’s shoulders.

‘Sure babe, this can be our date.’

Castiel relaxed into Dean’s side, and allowed Dean to tug him up to the entrance gates, where Sam was waiting impatiently. Sam rolled his eyes as he saw his brother and the angel strolling along together.

‘I’ve paid already,’ Sam grunted, and walked inside the gates without looking back. Dean’s hand slid back from Castiel’s shoulders, down his arm, until he was gripping Castiel’s fingers, pulling him through the gate too. They saw Sam walking away, towards the Dodgems, and Dean rolled his eyes before nodding to the Tilt-A-Whirl.

‘Let him cool down, we’ll go have some fun. Come on.’ He gave Castiel a swift kiss on the cheek, and tugged him along to the first ride, where they were strapped in to the same car together, knees bumping on the safety bar.

‘Dean? Are we about to get tortured?’ Castiel asked in a low voice, eyeing the restraints apprehensively. Dean laughed, as a bell sounded from the centre of the ride, signalling that it was about to start.

‘Some would say that. It’s going to be fun, Cas. Here we go.’

The car began to move, twisting around as it ran along the track, picking up speed as the music began blaring out, some old rock tune that Castiel had heard a thousand times in the Impala. Castiel wasn’t sure if he was enjoying the experience, but Dean was whooping, and laughing as the car rocked sharply and sent him sliding into Castiel. He put an arm around Castiel as they were thrown the other way, Castiel landing into Dean’s firm chest. Castiel decided he liked the ride, if it was going to continually bring them together.

The ride stopped before Castiel was ready, and as the car slowed to a halt, Dean shifted away from him slightly, pushing the safety bar off and sliding off the seat, turning around and grinning at Castiel. Castiel stared back at him, marvelling at how much younger Dean looked when he smiled, how relaxed he seemed despite the obvious tension with Sam earlier. Castiel followed Dean out of the car, and off of the ride, watching him as Dean took his hand and scanned around the area for the next activity.

‘Wanna go in the haunted house?’ Dean laughed suddenly. ‘See if it’ll freak us out.’

‘They have a house inhabited by ghosts? Do they know a failed Reaper?’

Dean shook his head in amusement at Castiel’s questions, pulling closer to him so they were standing chest-to-chest.

‘Cas, it’s a tacky carny ride. But it’s dark and a great place to make out. Especially when you get scared.’

‘I’ve been fighting demons since your species developed, Dean, I won’t be scared.’

‘It’s tacky as hell, of course you would be,’ Dean pulled away slightly, winking and threading his way through the crowds, Castiel hurrying to keep up, eventually grabbing the back pocket of Dean’s jeans to ensure they stayed together. When Dean felt the tug, he slowed down, reaching a hand behind him to grab at Castiel’s arm, and when he managed to grab it, he slid Castiel’s hand firmly into his back pocket. Castiel was glad that Dean was still looking for the haunted house, so he couldn’t see Castiel’s blush. He fought the urge to sink his fingertips into Dean, to see how firm he was under the worn denim wrapping, as Dean stopped walking, and half-turned to Castiel. ‘Here we go. You’re going to have to let go of my butt for the ride.’

Castiel hastily removed his hand from Dean’s back pocket, feeling scolded somehow. All the signs he had been reading so far from Dean indicated that Dean wanted him as well. He felt a burning sensation in his gut, even as Dean reached for his arm and tugged him into a rickety old cart, lowering the safety bar over them once again, and winding an arm around Castiel’s shoulders. The cart gave a jerk, and they slowly entered the dim house, Castiel looking all around at the fake cobwebs and poorly lit skeletons.

‘I see what you mean about the tack,’ Castiel said quietly, turning to look at Dean, who seemed to be staring at him. Castiel could only tell by the way Dean’s eyes reflected the light on the exhibitions. A mummy “fell” out of its sarcophagus, and Dean leaned over and kissed Castiel again, his hand gripping onto Castiel’s shoulder. Castiel lost himself in Dean’s kisses, trying to manoeuvre around the safety bar in order to get closer to the hunter. Dean used the hand on Castiel’s shoulder to pull him as close as he could, his kisses slightly sloppy as he searched through the gloom for Castiel. Castiel couldn’t make himself care, he was revelling in Dean’s affection, trying to remember every sensation connected with Dean’s lips and teeth and tongue, his firm grip, his warm torso, everything that made Castiel feel desired. If, at that moment Dean had pushed for more, Castiel would have gone willingly, his position in Heaven be damned. Literally.

But they were suddenly flooded with light and Dean pulled away, blinking around as Castiel sighed in frustration. The ride operator lifted the safety bar and Castiel stood up on weakened legs, leaving the cart and letting Dean out as well. Dean slid an arm around Castiel’s waist, giving him a tiny kiss on his neck. Castiel shivered as they fell into step, walking around the carnival.

‘So did you wanna go on another ride? Find Sammy? What do you wanna do?’ Dean asked after a couple of moments. Castiel knew his answer would not go well with Dean, and tried to think of something he could say other than go back to the bunker and fall into you. He saw a game, with guns and cork bullets, and nodded over to the stand.

‘How about that?’

Dean looked as Castiel pointed, and gave a soft snort of laughter.

‘Want me to win you the big teddy?’

Castiel didn’t comprehend what Dean was referring to at first, and then he noticed the garland of stuffed toys across the top of the stand. Dean moved forward and paid the carny for a round of shots, and Castiel stood back to watch as Dean raised the gun, his stance solid yet comfortable, and he shot at the milk bottles arranged on the back wall. As he did, someone sidled up to Castiel, and whispered in his ear, her voice lilting and almost melodic, a dreamy quality hiding the danger within.

‘Well, well, well, Clarence. Scoring with a Winchester? I guess it was only a matter of time.’

Castiel looked down at the blonde demon beside him, who raised her chin as she raised her eyebrows, almost challenging him in her amused way.

‘It’s none of your business, Meg.’

‘I’ve been watching you since you got here, Clarence. You’re all over him. It’s almost pathetic, the way you keep almost begging him for some kind of affection.’

‘It’s none of your business, Meg.’ He reaffirmed, trying to imitate Dean’s annoyed tones.

‘Please, Clarence, I want to help. Give Dean the chance to work out exactly what he’s lucked into. Don’t you want that? Winchester wanting you back just as much as you want him?’

Castiel didn’t want to answer, but Meg had got it perfectly right. Of course he wanted that.

‘So, what do I do?’

Meg smirked.

‘You let him see how desirable you are. Give him competition, make him work for the prize.’

Castiel frowned.

‘And how do I do that?’ He asked, still not fully understanding the picture that Meg was painting. Meg laughed, and reached up for him, pulling him down to kiss him. Castiel’s sense of reasoning diminished completely, and all that percolated through his brain was that kissing Meg was very different to kissing Dean. Meg’s height gave Castiel an odd ache in his neck as he bent down. Her mouth was softer, her skin was smoother, she had no stubble to scratch against Castiel’s face. Her hold on him wasn’t as constricting as Dean’s, and Castiel missed all these elements that stood out. He wanted to be pressed against Dean, their connection rough and hot and full of need.

Castiel pulled away, disgusted with himself for letting Meg talk him into making out right behind Dean, and he looked around, hoping the hunter hadn’t seen anything. But Dean was gone, and they were surrounded by crowds of humans who were all enjoying themselves, ignorant of the angel and demon in their midst.

‘Castiel, the point was that he saw-‘

‘Be quiet and get out of my sight.’ Castiel snapped, pushing through the crowds and away from Meg to try to find Dean. He had to find Dean, to let him know that it was all Meg, the entire kiss came from Meg, and Castiel was so far removed from interested. He pushed through the swarms of humans, feeling increasingly desperate. Where could Dean have gone? Was he that angry when he saw Meg and Castiel together?


Castiel never managed to find Dean at the carnival. If Dean wanted to be hidden, then he would remain hidden. Eventually, feeling crushed, Castiel returned to the bunker, invisible. The Winchesters had already arrived back, and gone to their separate rooms. Castiel ventured into Dean’s room, still hidden, and watched as Dean drank a beer as he watched Dr Sexy, MD on the television set attached to the wall. Beside him was a stuffed toy, not one of the huge ones that he’d promised Castiel, but it was still a soft toy from the stand. Castiel felt a strange tightness in his chest, and he wanted to appear, to talk to Dean about everything that happened, to explain about Meg. But he didn’t want to argue with Dean, or lose him completely. Dean finished his beer, and bunkered down on the bed, his back to the stuffed bear. Castiel waited until he was sure that Dean was asleep, and then he took the stuffed toy, pressed his fingers to Dean’s forehead to wipe his memory, and disappeared with the toy, hiding it in a remote part of the bunker that Dean and Sam were yet to discover. He knew it was deceitful, but he wanted to treasure the trinket that Dean had won for him without any awkward questions. Explaining to Dean why there was a soft toy in his room would have been awkward, and potentially led to complete heartache. At least, Castiel tried to reassure himself, tomorrow would be another day to try at a relationship with Dean.

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