Fifty First Dates

Chapter 8

Castiel had spent the entire night with the soft toy Dean had won for him, sitting in the undiscovered room and stroking its rough fur as he held it close. He felt guilty, a deep burn right in the pit of his stomach, and no amount of altering Dean’s memory was going to help remove it. More than anything, he wanted to explain to Dean, to give his side to the situation and know that Dean had forgiven him. He genuinely hadn’t known what Meg’s intentions were. He wouldn’t have responded if he’d known that she wanted to kiss him. He wanted Dean.

Castiel was aware when morning came, and he knew that Sam would be getting up soon, going for a run and then making coffee, and not long after that, Dean would surface and Castiel would have to figure out what to do. He’d been trying all night and hadn’t made any progress. He wondered if making some grand gesture would go some way to removing some of the guilt, or if it would seem stupid, because Dean didn’t know what had happened. He hugged the stuffed rabbit closer, his mind reeling with the memories of the day before. The good ones, like Dean insisting on walking with their arms around each other, as though he were showing Castiel off to the world. The way Dean looked at him on the ghost train ride, just before he began kissing Castiel. The way they were connecting in the bunker kitchen, before they went to that damn carnival. And all Dean’s kisses, the sloppy, needy ones. The charged, passionate ones. The affectionate little ones when they were in public. Castiel wanted to believe that the Dean he saw yesterday was the Dean he deserved, the one who seemed to love him back. Castiel wanted to believe that what Meg said was wrong, that it wasn’t a case that Castiel was all over a disinterested Dean. But now, along with the guilt, he had his doubts. He didn’t know what to do, how to go forward. Even though Dean wouldn’t remember, Castiel felt that maybe he had lost him for good.

Castiel dwelled for most of the morning in that sparse room, still holding the toy that smelled both of Dean, that leather-whiskey-earthy smell, and another more pungent odour. He had no idea what he was going to do, how he was going to handle seeing Dean, and having it confirmed that he and Dean were over. He wouldn’t be able to face that. But he knew Dean wouldn’t want to go too long without seeing him either, whether they were still a couple or not. Eventually, he plucked up the courage to go and see Dean, trying to calm down, to not over-react. He found Dean with Sam in the main room, the atmosphere charged once again as they squared up to each other. Castiel didn’t understand why Sam and Dean were suddenly at each others throats the last few days, and he was unsure what he could say to diffuse the situation. He would most like to kiss Dean’s full pink lips, and distract him that way, but it didn’t seem like a wise move while they were glaring at each other.

‘Maybe, Sam, the problem is you, huh? You think on that?’ Dean growled. Castiel’s head turned between the brothers, flicking back and forth.

‘Can I not just be concerned for you? Dean, it’s been like, six days of the same thing!’

‘How about you grow a pair?’ Dean spat, and turned on his heels, calling back as he left the room. ‘I’m researching the hell out of djinn!’

Sam deflated into a chair, and Castiel made to follow Dean.

‘Cas?’ Sam’s voice was softer, more weary, and Castiel knew that he couldn’t just ignore Sam for Dean right then.

‘Yes, Sam?’

‘Is he okay with you? I mean, is he forgetting stuff with you? You’re together so much these days, I figured you might have noticed something too.’

Castiel hesitated, not sure how to respond to Sam. Cas was counting on Dean not to remember a thing.

‘To be honest, Sam,’ Castiel spoke slowly. ‘Our relationship isn’t built on recording the minutae of the day. We discuss other things, or it’s physical,’ he coughed, though he had no need to, and could feel his cheeks burning. Sam looked away, embarrassed himself for having to hear about that end of their relationship.

‘Yeah, I walked in on you both naked the other day. And yesterday when you were practically having sex in the chair. I know.’ Sam sighed, and leaned across the table, looking at Castiel earnestly. ‘Look, I don’t really … I’m glad you make each other happy, I am. He needs it, and I’ve known for a while that you and he … I’m still worried about him, okay? Can you try and talk to him? He won’t shout you down the way he’s doing with me.’

Castiel nodded, still not making eye contact with Sam.

‘I can try, Sam. I can’t promise more than that.’

‘Good. Good. Okay, well, I’m going to look for some more potential cases, so Dean and I can head out when he gets over it. If you two can leave each other alone that long.’

Castiel nodded, unsure of how else he was supposed to act, and walked out of the room, assuming that Dean would be in his bedroom. But when Castiel stuck his head into the room, around the door, he found it empty. He walked back through the bunker, and found Dean in a room full of the Men of Letter’s records, sitting at a desk and hunched over a stack of paperwork, concentrating hard on the text. Castiel stood in the doorway, leaning against the frame, just watching in admiration as Dean removed a hand from under his chin to turn over a piece of paper.

‘Cas, are you in or out?’ He asked, not even looking up to check who was loitering at the door. Cas felt some of the weight in the pit of his stomach lifting, just from Dean recognising it was him. He stepped into the room, and headed to Dean’s table, sitting opposite him and looking intently at the hunter. ‘While you’re here, you mind helping me? Sam’s been acting strange, I think he got messed up by the djinn we killed yesterday. I need to find whatever records the Men of Letters have on djinn, so I can help him. Okay?’

So it wasn’t the conversation that Castiel thought they would be having, at least it was civil. Dean’s anger seemed to be directed only at Sam, and Castiel knew it was wrong but he was glad that Dean wasn’t angry at him and he didn’t care if Sam got the full brunt of Dean’s anger.

‘Dean? Can I talk to you about something?’ Castiel asked, emboldened by the fact that Dean seemed okay with him. Dean grunted, and Castiel took the grunt to signal Dean’s consent. ‘I kissed Meg. Well, she kissed me, but I didn’t exactly push her off. I’m sorry, Dean.’

Dean looked up from the page he was reading, and then put it down on the table gently.

‘Why’re you sorry?’

‘Well, because you and I- the whole dating thing-‘

Dean looked back at Castiel with a blank expression, and then shrugged.

‘Did you want to kiss her?’

‘No, of course not! You know how I feel about you.’

Dean didn’t react the way Castiel had anticipated, with a quirk of an eyebrow and a small smirk playing at his lips. Instead, he looked down at the papers, ready to continue his work.

‘It’s no big deal then, is it? It happened, it’s over, we can move on. Can I concentrate now? We’ll talk later.’

Castiel understood the dismissal, but he was still hurt by it. He wanted to reach over and take one of Dean’s hands, threading their fingers together and falling into a comfortable silence with that tenuous connection while Dean did his work. He knew Dean wasn’t in the mood at that moment for any kind of contact, so he used his normal bluff.

‘That’s fine. I have things to do in Heaven. I’ll see you later?’

Dean didn’t even look up, and Castiel barely heard his ‘mm-hmm’. Castiel zapped himself out and found himself in the Australian outback, surrounded by a deep red desert. He collapsed onto the floor, crossing his legs and surveying the flat, sparse surroundings. He knew Dean didn’t mean anything harsh, he wasn’t trying to upset Castiel, but Castiel felt it anyway. Why did he not react more to the news that Meg had kissed him? Why wasn’t Dean angry? He seemed so emotionless, and for Castiel, that was worse than Dean yelling. Castiel was taking it personally.


Hours in the heat passed, before Castiel heard Dean’s prayer. It was a painful echo of their last fight, when Castiel had spent the day in Nepal resolving to break up with Dean. This situation was more confusing, as was the tone of Dean’s prayer. His voice was flatter than normal, and he sounded tired.

‘Cas? I know you’re busy, but I’d really like to see you. When you can make it, you know? I’m going for a shower now, but I’ll wait up for you after that. It’s been weird, not having you around today.’

Castiel stood up, cleaned himself of sand, and zapped straight back into the bunker, into Dean’s room. It was vacant, and the door was ajar. Castiel could hear the shower running down the hall. He tried not to dwell too long on the mental image of Dean naked under the spray, the droplets running down his firm chest and sculpted abs, defining Dean’s muscles. Castiel played with the knot in his tie nervously. What exactly was Dean expecting now?

The noise of the shower shut off, and Castiel could hear the soft footfalls of Dean’s approach. Dean walked in, towel slung around his waist, and flung himself down on the bed, spotting Castiel as he rolled over, the towel barely staying in place. Castiel’s eyes were firmly on the towel.

‘Hey, you came pretty quickly.’ Dean sounded surprised, but happy.

‘Well, you asked me to.’

Dean nodded, which Castiel only caught in his periphery vision.

‘I know, but I know you were busy. Hey, shut the door, make yourself comfortable.’

Castiel flicked his fingers and the door closed, but he remained standing. Dean smirked, adjusting the towel, and beckoned Castiel closer. He didn’t move, and Dean rolled his eyes.

‘Cas, get on the bed with me.’

Castiel took a deep breath in, exhaling slowly, and then he removed his trench coat, his eyes locked on Dean’s. Dean cocked an eyebrow, his smirk growing into a genuine smile, and Castiel clumsily removed the rest of his clothes, leaving his boxers on before he crawled onto the bed, next to Dean. They lay side by side for a moment, not touching, not speaking.

‘This is awkward,’ Dean said eventually.

‘You wanted me to join you on your bed, I have done.’ Castiel began to object, and Dean sniggered.

‘That’s not what I meant, Cas. Come here,’ Dean’s fingers skated over Castiel’s skin, until he found his wrist, tugging at it gently. Castiel shifted along the mattress, until he was laying next to Dean, leaning over him slightly. Dean kept hold of his wrist, tucking his other hand behind his head and smiling lazily at the angel. Castiel propped himself up, staring wide-eyed at Dean. Their chests were pressed together lightly, and Castiel wanted to shiver at the feel of Dean’s shower-softened skin against his own. Dean began stroking his hand up from Castiel’s wrist, along his forearm, and stalling just above his elbow. Castiel took his cue from Dean, and rested a hand lightly on Dean’s face, his fingers exploring Dean’s jawline as they stroked the soft skin. He could feel where Dean had shaved, the shortened bristles catching only slightly on the pads of his fingers. He leaned closer, looking at the light brown hairs dotted along Dean’s face, the pale freckles that coated Dean’s cheek, aware that Dean was watching him.

Castiel was avoiding the eye contact, just for a while. He knew that as soon as he looked at Dean, as soon as they made that connection, that Dean would raise his head, just slightly, catching Castiel’s mouth in his own, and then things would turn frantic, because they would be far too immersed in each other to think. Castiel just wanted to savour their small connection while it was innocent.

‘That feels nice,’ Dean said quietly, and Castiel knew Dean was closing his eyes. Castiel took the chance to glance up Dean’s face, and the way that Dean’s long lashes lay lightly against his tanned skin. His fingers traced the contours of Dean’s face, around his eyes, over his nose, along his cheekbones and his eyebrows. Dean sighed, his lips parting minutely, and Castiel began tracing the outline of his lips too. Dean’s hand crept up along Castiel’s arm, up past his shoulder, and he began rubbing his fingers gently on the soft skin behind Castiel’s ear, his eyes flickering open as he did. There was a strange moment where they just looked at each other, before Castiel tucked his hand on Dean’s side, his fingers curling around Dean’s ribs, and he noticed that Dean’s skin was soft here from the shower also, and though it was cool to touch Castiel could feel the warmth underneath. Dean stroked a thumb down Castiel’s cheek, a tender look in his eyes. ‘I wasn’t trying to blow you off earlier, Cas.’ Dean broke the silence.

‘Okay.’ Cas didn’t want to rock the boat with his insecurity. He was enjoying whatever this was with Dean, especially after the uncertainty that came from Meg’s kiss.

‘Hey, don’t be mad,’ Dean whispered, running his fingernails over Castiel’s scalp. Castiel wanted to be angry that Dean had started scratching him, but there was something relaxing about the motion. He closed his eyes instead, moving his head into Dean’s fingers. ‘I’m going to make it up to you now, okay?’

‘How’re you going to do that?’ Castiel was barely audible. Dean laughed quietly, still running his nails across Castiel’s head.

‘Think I already am,’ Dean purred. Castiel nodded, not wanting Dean’s touch to end. ‘Is this what you wanted, Cas? When you asked me out?’

‘What do you mean?’ Castiel’s voice was slow, sluggish. The words felt like they’d been dredged through syrup.

‘This, you and me, in our own little world. Is it what you wanted?’

‘I don’t know, Dean. I just wanted you.’

‘I prefer this, you know. Just us.’

Castiel didn’t know how to respond. Dean was rarely this open with anyone, and he was worried that one false move would make Dean clam up, would stop his wonderful touch.

‘What were you after, Cas?’ Dean whispered again. Castiel opened his eyes, and saw Dean smiling up at him. ‘Be honest.’

‘I don’t know, Dean-‘

‘Please, Cas. Tell me.’

They stared in each other’s eyes for a few moments, and Castiel could feel, underneath his chest, Dean’s heart beating more rapidly than his own.

‘I wanted more than just one date.’ Castiel’s voice was low, and though he wanted to he couldn’t turn away from Dean’s luscious green eyes. He felt like he was falling into them.

‘I know.’ Dean’s voice had gone husky.

‘I like all the dates you’ve been talking about, they sound nice, and completely human experiences. But I want to do more than those, I want to travel across the world with you, and show you everything that humans have achieved, everything my Father made to be admired. I want to take you to the coral reefs in Australia, the barren plains of Russia, the peak of Mount Everest. I want to show you things no other human has seen, like the bottom of the ocean and the view from Mars. I want to take you back to the Mayans, the Egyptians, when Columbus discovered America, or take you forward to see what could possibly come for your species in the future. I guess I just want to show you everything I love.’

Dean had been quiet the entire time Castiel was laying himself bare, though his fingers didn’t falter on the angel’s scalp. Castiel assumed he’d gone too far, revealed too much and made Dean uncomfortable, but he didn’t want to shift from the comfortable position on Dean’s chest when the hunter inevitably got angry.

‘Cas,’ his voice broke on the syllable, and he finally stopped scratching Castiel’s head, bringing his hand around and cupping Castiel’s chin gently. His eyes flicked back and forth for a moment, and Castiel realised that Dean was trying to decide which of his eyes to focus on. ‘Maybe we could work something out.’

Castiel didn’t know how to respond to that. Was Dean … was he suddenly open to more than one date? Could Castiel have everything he was after? The door swung open before Castiel had to think of a reply, and Sam walked in, talking.

‘Are you going to sulk all day, Dean or can we-JESUS!’ He had finally noticed that his brother wasn’t alone, and that he and Castiel were practically naked again.

‘No, it’s Cas. Is Jesus a compliment?’ Dean grinned at Castiel, and the angel knew the moment had gone. The serious, quiet talk that they were having, the opportunity to push their relationship in the direction Castiel wanted, it was all gone.

‘Jesus was a man, not an angel.’ He muttered, dropping his gaze to Dean’s chin, and the tiny hairs that covered it. Dean turned to Sam.

‘Can you go now?’

‘Yeah, I need to go burn my eyes out now. Maybe put a bullet in my brain. Because Dean? Your towel isn’t covering a thing.’

Sam stalked out of the room, slamming the door behind him, and Castiel cast a casual glance down to Dean’s towel, trying to see what Sam had been referring to. All he could see, past Dean’s muscular stomach, was the fluffy white threads of the towel. Dean laughed, his body rocking slightly underneath Castiel.

‘Are you trying to get in on the show?’

‘No, I just,’ Castiel looked up, and saw the humour dancing in Dean’s eyes. ‘I didn’t think Sam was correct. And he’s not, you’re covered.’

‘Do you want me to be covered?’ Dean’s words were teasing, but the catch in his throat meant that Castiel knew the truth. Dean wanted to be naked in front of him. Did he want the same back from Castiel? And what would it mean for Castiel’s grace?

‘I don’t know, Dean.’ He murmured.

‘Hey, Sam’s not going to come in again, quit worrying.’

‘I’m not,’ Castiel looked deep into Dean’s eyes.

‘Yeah, you are. I know you, Cas. Talk to me.’

‘I’m not worried about Sam,’ Castiel repeated. Dean untucked the hand from behind his head and began scratching Castiel’s head again, still holding his chin with the other hand.

‘What’re you worried about?’

Dean was looking at Castiel intently, his whole body shifting towards the angel as though that would somehow give Castiel the reassurance he needed.

‘It’s just … I’ve fallen for you in so many ways, Dean,’ Castiel didn’t miss the moment that Dean seemed to wince, but he ploughed on regardless. ‘And Heaven has always taken me back, which is more than any other rebellious angel has ever been granted. I’m worried that if we continue like this, I won’t be taken back again. I’ll be in a worse position than Lucifer.’

Dean was frowning, and Castiel reached up to smooth the creases in his forehead.

‘The other angels are dicks,’ Dean said simply. ‘It’s not between you and them, Cas. It’s between you and me.’

‘I think it’s between myself and my father, Dean. If he were here still, I would ask his consent to be with you.’

Dean smirked.

‘Think that’s my job. Do you want to?’

‘Do I want to?’ Castiel repeated, perplexed. Did Dean mean for Castiel to ask for God’s permission to be together?


‘Do I want to what?’ Castiel pressed, moving his hands to run through Dean’s hair, which was soft and fluffy from the shower, and silky-smooth to touch.

‘Have sex with me.’

Castiel stopped moving his hands, and instead gazed intently at Dean.

‘I mean, if you could guarantee you’d still be an angel, still be allowed in Heaven, none of that stuff even mattered. Would you want to sleep with me?’

Castiel barely made a sound, he merely mouthed the word yes. Dean smiled, and began trailing his hands down Castiel’s chest.

‘Good. Because I want to fuck your brains out.’

Castiel waited for the inevitable onslaught, of Dean’s grabbing limbs and thrusting hips and urgent mouth, but none of it came. Instead, he stroked his fingers back and forth along Castiel’s body, and though his touch was warm, it sent shivers all over Castiel.

‘I want to strip you down, until you’re naked in front of me. I want to kiss you all over, touching you wherever I can, feeling you react to everything. I want you to go down on me, licking and sucking like the only thing you ever needed was my dick, but before you get me off, I spin you around and slam into your ass like sex began with us. And I don’t want to stop, Cas.’

Dean was whispering, but the words were loud to Castiel. He stared back at the hunter, unable to believe the comments Dean was making. He wouldn’t be able to talk to Dean the way Dean was talking to him, would not be able to express his physical urges in that way. He said the only thing that seemed halfway appropriate.

‘I want to give you that experience, Dean.’

Dean stared back at him, and then slowly trailed his fingers to the band of Castiel’s boxers. Castiel sucked in a breath as Dean began to peel them down slowly, his fingertips grazing on Castiel’s lower abdomen, and along his legs. Dean sat up slightly, pushing Castiel down onto the bed, their eyes never leaving each others as Dean shuffled slowly down the bed, his towel falling off as he pulled Castiel’s underwear all the way off. And then he sat back, looking at Castiel, his eyes sweeping lazily over Castiel’s body. Castiel could feel a strange tingling sensation, as though Dean’s gaze had manifested into something real, with a feather-like touch.

‘Dean,’ Castiel found himself almost moaning the name.

‘We won’t do anything, Cas. I get it. But I can still appreciate your body, can’t I?’

‘It’s just a vessel,’ Castiel found himself protesting.

‘Not to me, it isn’t. It’s all Cas, to me.’ He crawled back up the bed, and Castiel looked up into his face as he did so, feeling his entire torso buzzing, like he was the empty home of a thousand bees. Dean lay down on Castiel this time, their faces so close that Castiel could feel Dean’s breath on his own mouth, Dean’s chest a firm weight on Castiel’s, their legs twining together as though they couldn’t be comfortable any other way. He was aware of Dean’s genitals pressed against his own, but for his own sanity, Castiel tried to put it out of his mind. Instead he focused on the green that hovered above him, intense and warm and intelligent. Dean’s eyes revealed too much of his softer side.

‘I’m trying real hard not to fool around with you, you know.’ Dean whispered.

‘So am I, Dean,’ Castiel promised breathily. And in a moment of reckless desire, he blurted. ‘Who are we trying that for?’

‘Well, you said your-‘

‘Please Dean, please touch me.’

Dean bit his lip, and Castiel groaned.

‘Please, please Dean,’ he leaned up, catching Dean’s lips with his own, trying to remember what happened in some of the videos he’d watched on the internet. ‘Do we have lube?’

‘No babe. We don’t,’ Dean leaned away slightly from Castiel’s searching lips. ‘Okay Cas, okay, here’s what we do.’ He sighed, and tugged at his hair in frustration. ‘We’re not going to sleep together tonight, it’s too soon. We haven’t even had that date you wanted, not really. And like you pointed out, no lube. But I will do one thing for you. Okay?’

Castiel nodded, his breathing already coming out in shaky starts and stops. Dean smiled, and reached down to kiss him properly, his tongue lashing around Castiel’s, their mouths pressed together, and he began to move in a sinewy motion over Castiel, rolling down from his shoulders to his knees. Castiel felt himself get hard against Dean’s stomach, as Dean slowly manoeuvred back down the bed, kissing every inch of the angel’s skin, just as he had promised. His hands caressed Castiel’s torso as he progressed, pausing to massage Castiel’s nipples, to suck on each one, licking and nibbling as he did. Castiel was beginning to moan incoherently, enjoying this experience more than the last one. There was a difference in Dean’s attentions, and Castiel felt more secure with what was happening, even as he had no control over what Dean was planning.

‘What are you going to do to me, Dean?’ Castiel whispered, closing his eyes as Dean left his nipples alone, kissing onto his stomach.

‘What I said I wanted you to do to me.’

Castiel thought back, and realised where Dean’s mouth was heading. He began to push down on Dean’s head, urging him onward, untangling his legs from Dean’s and wrapping them around his torso instead. Dean’s mouth was finally at Castiel’s groin, and he began planting tiny kisses along the shaft, taking his time, teasing Castiel. Castiel kept his eyes firmly closed, trying to enhance the experience by remaining unaware of what Dean was planning. Dean’s breath alone was erotic, caressing the sensitive skin as he moved, licking along the underside of Castiel’s cock. Castiel groaned loudly as Dean got to his head, and began working his way down, his mouth sealing over Castiel, making a rhythm with his head movements that Castiel found himself responding to, thrusting up into Dean’s mouth every time Dean descended on him. All of Castiel’s doubts were muted by the explosion of sensation that was erupting within him. He could vaguely hear the thump of Dean’s headboard against the wall, the creak of the bedsprings underneath the memory foam mattress Dean favoured. But it didn’t register as much as the way Dean’s lips were sliding up and down over him, the warmth of Dean’s breath, the way he was twirling his tongue around the shaft, the way his hands were still caressing Castiel, exploring every inch of skin he could reach.

Castiel was lost in the moment, in the way that Dean was giving this one appendage so much attention, in the way his body was responding as though it knew what Dean was intending. And then the world exploded, and Dean stopped moving, and Castiel started to come back to himself. He heard Dean gagging slightly, his mouth still wrapped halfway along Castiel’s penis. The angel lifted his head though it felt leaden, and tried to focus on what was wrong.


Dean didn’t respond straight away, but slowly lifted himself from Castiel, pressing his lips together and swallowing, then looking back up the bed, into Castiel’s eyes. He crawled back up the bed, and burrowed next to Castiel, kissing his shoulder and grazing his knuckles along Castiel’s bicep.

‘Was that okay?’ Castiel asked. He knew from the videos and descriptions and diagrams he’d seen just what Dean had done for him.

‘Mmm, yeah. How was it for you?’

‘An experience.’ Castiel admitted. Dean chuckled into his shoulder.

‘A good one, I hope.’


Castiel turned his head to look at Dean, and brushed a kiss across his forehead. If sex was going to be anywhere near as good as that, then Castiel would be willing to fall completely for Dean. He wanted to tell Dean that, but he was worried Dean would pass it off, a result of the effects of the fellatio. Castiel’s mind was almost set. Dean would be entirely worth it. Besides, why would Castiel want to be in Heaven if it wasn’t guaranteed that Dean would get in?

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