Fifty First Dates

Chapter 10

Castiel erased Dean’s memory feeling more conflicted than ever before. The night had gone well, Dean had been desperate for physical contact, and Castiel wasn’t sure but he might have been complimented on how okay he was in his performance. He knew there was a diminishing reason for him to continue wiping Dean’s memory of their relationship. He wanted Dean to remember, he wanted to get passed the awkward first moments and take things further. The only justification he could come up with this time for erasing Dean’s memory was that Dean had seemed ashamed when he had climaxed early. Castiel had decided that was as worthy a reason as any to remove the previous day. Castiel wouldn’t hold it against him, but Dean had a habit of beating himself up for the smallest of excuses. Next time, he would pay attention, and not tease Dean so much before intercourse. Next time, his boyfriend would come before showing off.

Castiel wanted to lay with Dean, to rest his head on the hunter’s chest and listen to his heart beating steadily, but with Dean’s memory erased, it would be a risky manoeuvre. Instead he hid all of the toys back in his safe place, and went walking through the bunker, thinking about what to do next to secure their relationship. At least, he did until he heard someone summoning him.

He should have expected this, from the moment he saw them in the movie theatre. From the moment Meg told him that everyone was aware of Dean’s failing memory. And yet he felt completely unprepared for what was to come. He could only do his best to protect the Winchesters, however he needed to do that. He vanished from the bunker, reappearing moments later on a barren hillside, where one angel stood, her hair whipping around her face, her coat picking up in the strong wind surrounding them, and yet she seemed wholly unbothered by the weather.

She looked different to how she had appeared in the movie theatre, or just outside where she watched Dean’s onslaught of Castiel with distaste. Castiel knew she had been borrowing a vessel at the time, a young male, instead of the elder woman that was her true vessel.

‘Castiel,’ she nodded curtly. Castiel merely stood in front of her, trying to wear a poker face. They both let the silence drag on for far too long. ‘How is Dean Winchester?’

It was the wrong question. How was Castiel meant to answer? She had seen them kissing, she had heard the things that Dean whispered in the dark. She knew that they had a strong connection, and she would have known that without having witnessed it first hand. Ever since Castiel had pulled Dean from the pit, the other angels whispered about their connection. It had been part of Castiel’s downfall.

‘Castiel, please, talk to me. We used to be so close.’ She pressed her lips together, her laughter lines highlighted even in this small action. And Castiel felt torn. It was true, they were friends before they were split into their different garrisons, but that was several millennia ago. They had been given different assignments, and grown far apart, and then there had been Dean …

‘You’re taking a human vessel now?’ Castiel asked eventually. ‘What of the cat organisation?’

‘I’ve been reassigned. I’m part of a team looking for renegade angels. You might call it a promotion.’

‘I would. Fur balls don’t sound particularly pleasant.’

‘No. They aren’t. But nor are angels who go against orders.’

Castiel paused before responding. If what she was saying were accurate, she wouldn’t be alone when confronting him.

‘Vibeke, you’re going against orders to talk to me now. Will someone come for you?’

It was the wrong thing to say.

‘Do you think I don’t have clearance? I’ve made my appeals for this conversation, Castiel! They know our history, they know I know you better than most angels. I told them you would respond better if you weren’t outnumbered. Your little date with your pet human proved that beyond a doubt.’

So that was why there were four of them the night before, not taking any action. Castiel bristled at the way she dismissed Dean so easily, and decided to make Vibeke’s job even harder.

‘So what happens now?’

‘Now? Now you stop, Castiel. You leave Dean Winchester alone.’

‘What happens if I decide not to do that? What if Dean’s more important?’

Vibeke laughed.

‘Please, Castiel. You can stop pretending with me. I know how tough it is for you to be with anyone.’

Castiel looked away, trying to block the memories of two young angels, a pushy, black-haired girl and a shy, dark-haired boy, and her insistence that they were made for each other. The elder angels had said it, she’d insisted, but he had never felt it. Even when she stole his first kiss, he felt nothing but friendship there. It was nothing at all compared to the emotions that stirred in Dean’s presence. He could hear the Winchester’s praying to him, and repeated himself, his voice taking a harder edge.

‘What happens if I pick Dean?’

‘You know what happens.’ Vibeke answered cryptically. Castiel shrugged and met her eyes again.

‘And yet, I pick him.’

‘What if he doesn’t pick you?’

‘That’s my burden to bear, I guess. But I know Dean better than you do, Vibeke.’

Vibeke approached him carefully, placing her hands upon his shoulders.

‘Time will tell that, Castiel. And please, don’t think I’m not rooting for you to get past this. I will fight for you in Heaven, Castiel. But not for him.’

Castiel scowled, but before he could give another indignant response, Vibeke closed the distance between them, kissing him gently. He pushed her away.

‘It’s never going to happen, Vibeke.’

‘You’re going to Fall? For him?’

Castiel wrestled his shoulders away, stepping back and preparing to zap out.

‘I don’t know how you missed it, Vibeke. I already did.’

He zapped back into the bunker, before Vibeke could make him feel worse, and listened for the sounds of Dean and Sam. The bunker was silent. Castiel went tearing through the hallways until he reached Dean’s room, where the pink handcuffs lay on the bedsheets, and a few condoms were strewn on the floor. It was otherwise neat, and organised, the way Dean liked the room. The way Castiel liked the room. But it left little by way of clues for where Dean could be, and right then Castiel wanted nothing more than to fall into Dean’s arms and be reassured that Vibeke was wrong. He closed his eyes, and tried to concentrate on where Dean could possibly be, as though their connection was in some way corporeal and a viable means of finding each other. And then he zapped out again, relying on faith alone.

Somehow, it worked, and he found himself in a field with the brothers, their car parked close by, and Dean was snapping at Sam.

‘… know better than this, Sam!’ Dean was spitting, his back to Castiel as he squared up to his taller brother. Sam seemed upset, and Castiel wondered what could have led to them standing in a field, screaming at each other.

‘Maybe-‘ Sam began, and then paused as he noticed Castiel. Dean whipped around, his expression stony, the bags under his eyes heavy. He seemed weary to Castiel, who just wanted to take away some of the emotional load Dean insisted on carrying.

‘Hey, you okay Cas?’ His tone was harsh, and Castiel tried not to take offence at it. He’d been arguing with his brother, and that always made Dean tense. But physical contact seemed to calm Dean down, so Castiel felt justified in stroking his arm gently, trying to appeal to the side of Dean that had agreed to date him. His reaction was jarring. ‘Dude!’

Cas blinked in his confusion as Dean pulled his arm back, his expression a mix of confusion and angry. Dean had never once, in the entire time they’d been having their first dates, reacted badly to him. Had Vibeke messed with Dean at some point that Castiel was unaware of? Had she sent someone to intervene as they had talked? Had someone gotten to his Dean? Sam approached tentatively, but Castiel was once again less concerned with the younger Winchester. It was hard to be, when the love of his life was right in front of him, reacting negatively to his touch.

‘Dean? Is everything okay?’

Dean merely frowned at Castiel, as Sam joined them.

‘Dean’s memory is messed up, Cas. Worse than before-‘

‘I’m right here, Sam!’

Castiel looked over in time to see Sam roll his eyes, before concentrating all his attention on the angel.

‘I don’t think he remembers stuff for a couple of weeks. He thinks I’m joking about the two of you.’

Dean folded his arms, glaring at Sam.

‘That’s not funny, Sam. It stopped being funny about five seconds after you started it.’

Sam continued talking to Castiel as though Dean were not interrupting.

‘At first, I thought you’d fallen out, and then he kept reacting like this. But his memory lately has been bad, and I figured maybe it was just getting worse. I just wish I knew what was causing it.’

Castiel tried to keep his features straight, and not react to what Sam was telling him. He didn’t want Sam to work out that he was the cause of Dean’s poor memory. Instead, he relented slightly, and decided to give Dean something back. He needed it himself right then, that blazing look in Dean’s eyes that threatened to consume Castiel.

‘I don’t know what’s causing it, Sam, but maybe I could get something back.’

Sam looked relieved, and Dean angry.

‘I don’t need help! I’m fine, Cas!’

‘What’s the last thing you remember?’ Castiel insisted, looking at Dean.

‘I don’t know, we were laughing about something in a motel room. Sam was asleep already.’

Castiel bit his lower lip, worrying. As soon as they began discussing a relationship, their conversations had turned serious. Dean couldn’t remember any of their agreement. But Castiel had been careful to only erase the day.

‘Were we talking about salad?’ Castiel dropped his voice, aware Sam could hear him. They hadn’t been mocking Sam, exactly, but neither of them understood his fascination with salad.

‘Why would we talk about salad? Except-‘ Dean’s eyes flickered to Sam, and understanding seemed to blossom there. He turned back to Castiel. ‘Yeah, that makes sense.’

Sam shook his head, and Castiel stepped closer to Dean, hoping that there wouldn’t be a problem between the brothers over one small conversation.

‘Dean, you’ve lost weeks. I’m going to try to get it back, okay?’

Dean looked ready to protest, but Castiel stepped forward and pressed two firm fingers to his forehead before he could. As Dean fell into an unwanted sleep, Sam stepped forward and grabbed his brother before he crumpled to the ground. Castiel pressed closer to the hunter, placing his fingertips on Dean’s temples, and Sam spoke up once more.

‘You were laughing about me eating salad all the time?’

‘It’s a little more complicated than that. And it was more about salad than about you.’

‘Well, that makes me feel better.’ Sam sighed. ‘Can you do it? Get all his memories back?’

‘I can try. Give me some time.’

‘Can I put him down first? He’s real heavy when he’s asleep, Cas.’

Castiel nodded, shucking off his trench coat and balling it up as Sam lowered his brother to the grass-covered ground. Castiel put his coat underneath Dean’s head, and touched his temples once more, breathing deeply and trying to concentrate on the images that came through, of the last few weeks where Dean and Castiel began to cement their relationship. How much could he give back to Dean? Dean would realise that Castiel had been resetting his memories, and Castiel couldn’t imagine how he would react. But he had to give something back. He wished he could hear Dean’s thoughts in the memories, to know when to cut it off, but he wasn’t blessed with that kind of power. Instead, he got to the day before their paintball excursion, and reset the dates. Then he allowed the day before to come back, the day when Dean wanted nothing but him. The day they had explored their physical relationship to a degree Castiel couldn’t begin to conceive before. Would that be enough? He couldn’t influence Dean’s opinions or emotions from the past, all he could do was hope that it would work out for the best.

He withdrew his fingers from Dean’s temples, and Sam, who had remained quiet as Castiel worked, finally spoke up.

‘Should we wake him up?’

‘He’s going to be disoriented, Sam. We should leave him to rest.’

‘We think there’s demons in the area, Cas. It’s not safe out here.’

Castiel turned slowly to the younger Winchester.

‘There’s been no demons here.’ He could feel that very clearly. But Sam wasn’t aware that there had been angels in the vicinity, and Castiel was already sick of the other angels.

‘Still, how long will he be out? We’re trying to work a case.’

Castiel shrugged.

‘We’ll drive him to your motel room, he can come around in there.’

‘We haven’t found a place yet.’

Castiel sighed, and looked at Dean again, noting how peaceful he looked in his sleep. He didn’t want to ruin it, but he knew Sam was going to keep pressing the issue until Dean was awake, whatever that did to his elder brother. Castiel would never fully understand their connection, though he knew that Dean would appreciate it if he acted on Sam’s request, at least a little. So he pressed his fingers to Dean’s forehead once again, and watched as Dean began to stir. Dean’s eyes blinked open, and Castiel felt an ache in his chest, around his heart. It was like watching Dean wake up in the morning, where Dean was so vulnerable, so unaffected by the problems that life brought, at least for a moment. Castiel gave him a watery smile, as Dean’s eyes became focused.

‘Where’d you go?’

Castiel frowned, surveying Dean with concern. Had he done something wrong? Had he somehow wiped out that days events, trying to grasp those memories back? He answered as though Sam wasn’t there. Sam didn’t exist for Castiel at that moment in time.

‘I’ve been right here, Dean.’

‘This morning. I woke up without you.’ Dean blinked again. ‘Where’d you stash everything?’

Castiel smiled, without really following what Dean was referring to, and before he could ask Dean to explain what he meant, Sam interrupted their moment.

‘So? Do you remember everything now?’

‘Everything important.’ Dean winked up at Castiel, who looked away, unable to lie, even by omission. Every moment they were together was important, and Dean only knew the bare facts. Sam missed the moment between the two of them, and went on with his own agenda.

‘Good. I vote we go talk to Rebecca, find out what’s going on. Her articles were solid, I don’t understand …’

‘Yeah, fine, we’ll do that. Can I just have a minute with Cas?’

Castiel looked around, and saw Dean staring at him with that desperate look in his eyes. The entire reason he gave the day before back to Dean. Castiel was aware of Sam stomping away, and then Dean was trying to sit up. Castiel lowered him back down, his hand lingering on Dean’s chest.

‘Don’t rush it. How are you feeling?’

‘Fine, Cas. Hey, what’s up? Are you pissed I forgot about us?’

Castiel needed to work harder to hide his feelings from Dean.

‘No, Dean. You couldn’t help that. I just wanted to help.’

‘I know. So why do you look like I killed your puppy?’

How was Dean able to work out Castiel’s emotions so quickly? Castiel was still smarting from his encounter with Vibeke, and then learning that Dean didn’t remember their relationship was another huge blow. He hadn’t realised that his disappointment and upset was evident on his face. He answered in his normal way, sure that Dean would see through the facade.

‘I don’t have a puppy.’

Dean looked exasperated. Castiel was right, he hadn’t fooled him at all.


‘It’s nothing, Dean. I’m just worn out from trying to look through your mind. I was trying to avoid invading your privacy.’

Dean swallowed this lie.

‘Did you see what I saw?’

Castiel nodded, and tried to reassure Dean that he hadn’t fully invaded Dean’s privacy.

‘But not your thoughts, nor your emotions. Just the images. Which was difficult when you were blindfolded.’

Castiel smiled at his own joke, and Dean gazed back at him, his eyes full of lust, before he sat up, surprising Castiel with a kiss. Castiel wound his fingers around Dean’s neck, sinking happily into the feeling of the hunter’s lips, as Dean rested a hand on his waistband, his touch as tentative as their kiss. Castiel was lost in Dean’s gentle touch, his mind repeating Dean is mine like a mantra. He wondered what Dean was thinking about as they kissed. His eyes flickered open, and he saw, just behind Dean, Sam leaning against the Impala, watching the two of them as they made out like teenagers.

‘Dean, Sam’s watching us,’ he murmured, not straying too far from Dean’s mouth. He felt the corners of Dean’s lips twist up as he responded.


‘I think he wants us to go. Who is this Rebecca?’

Sam had mentioned Rebecca as though she would be familiar to Dean, though Castiel had never heard of the woman.

‘His girlfriend. He met her online. He got this case from her. I think she’s possessed. Or worse.’

Castiel sighed, knowing that if this Rebecca person were possessed, it was important to exorcise her as soon as possible. He pressed one final, lingering kiss against Dean’s lips, and rested his forehead against Dean’s.

‘We should go. He looks upset.’

‘Stop checking out my brother.’

Castiel heard the humour in Dean’s voice, but he was worried that there was an insecure undertone too. He tried his best to reassure his lover.

‘I would never. We should take him to Rebecca. We’re more likely to get time to ourselves that way.’

Dean nodded, and scooted back, turning and seeing the trench coat in a neatly folded pile, complete with head-shaped dent.

‘Hey, your jacket. Why’s it there?’

‘I was protecting your head from the ground.’

Castiel reached over and grabbed it, feeling mocked without knowing how or why. He stood up, and reached a hand out for Dean, aware still that the memory manipulation might have had an effect on his head. Dean allowed him to help him up, keeping a hold of Castiel’s hands. They approached Sam with their fingers laced together, both of them ignoring his cocked eyebrow. Dean spoke up when they got near to the front grate.

‘Cas has shot gun.’

‘Oh, come on, Dean!’ Sam immediately protested. Dean shrugged, and squeezed Castiel’s fingers before letting go, and climbing into the driver’s seat. Castiel exchanged an awkward look with Sam. On one hand, Castiel was Dean’s boyfriend, but on the other, Sam normally sat in the front seat.

‘It’s okay Sam, you can sit with him. I like the back seat.’

‘It’s fine, Cas. He’s probably shaken about the whole memory thing. And I could do with some shut-eye before we get to Rebecca’s place. It’s about an hour away.’

Castiel knew that Sam was just being nice, and making excuses. And he really wanted to sit alongside Dean, he wanted that closeness, so he stopped being polite, and climbed in, hoping Sam would pass it off as his typical naivety. Dean started the ignition and drove slowly across the uneven ground, the car stereo playing one of the old tapes that had at first scared Castiel, yet now felt familiar, and safe. Like Dean.

A few minutes passed, and Castiel spent the time staring out of the windscreen, thinking about Vibeke, and what he was going to do. She had never understood why he had refused her advances, and he was sure that was why she was so bitter about Dean, but that couldn’t influence the way Castiel was going to be treated by the other angels … could it?

‘Is Sam asleep?’ Dean broke the quiet, and brought Castiel back to reality. He turned around and looked at the back seat, where Sam was folded uncomfortably, his arms cross, eyes closed, and mouth hanging open slightly. His breathing was slow and steady, unpunctuated by his normal snores. But Castiel could sense that Sam wasn’t conscious.

‘It appears so.’

‘Come here,’ Dean stretched an arm along the front bench, and Castiel scooted over happily, dropping a hand on Dean’s thigh as he rested his head on Dean’s shoulder, feeling the hunter relax as he did. Castiel was astounded by how close they seemed at that moment, how normal and everyday, like all the humans he had studied over the years. It made his chest ache, how easily they fit together. Why would the other angels want their relationship over? He needed to let Dean know, in some way, how he felt, so he reached up, kissing Dean’s chin. Dean smiled, and Castiel took that as permission to carry on, so he tried to kiss his boyfriend properly, on his full lips. The hunter pulled back, eyes focused on the stretch of asphalt before them.

‘Come on, Cas. I need to be able to see the road.’

‘Your mouth is so kissable.’ Castiel resented how breathless and needy he sounded.

‘So’s yours, but come on, you were the one who said to get to Rebecca’s place, and then we’d have us-time quicker.’

‘So no kissing?’

‘No kissing, not while I’m driving.’

Castiel wasn’t defeated yet.

‘But other things?’

Dean frowned, and shrugged.

‘So long as I can still drive.’

‘So this is fine?’ Castiel squeezed the leg he was holding, watching as another smile traced Dean’s mouth.


‘And this?’ He kissed along Dean’s neck.

‘Yeah, you can do that.’

Castiel understood the boundaries that Dean was setting. Nothing in front of Dean’s face. He could work around that. Spurned on by a newly-churning feeling in his chest, he slipped his other hand up Dean’s shirt. His only reaction was to let out a slow breath, and stare at the road ahead. Castiel traced his fingers down Dean’s skin, and when he got to the button on Dean’s jeans, he got an idea. He was going to Hell anyway, when the other angels were done with him. He started working the button open, and heard Dean’s breath catch.


‘Shhhhh. Stay quiet.’

He pulled the zipper down slowly, sliding his hand between the tight denim and Dean’s thin cotton boxers, feeling the heat of Dean’s penis through the flimsy material as he caressed it, noticing the way it jumped at his touch. Castiel nibbled at the hunter’s jawline, as Dean let out another slow, controlled breath. The angel decided that he would take control again, to see what his boyfriend would do. Dean was usually so in control, and yet with Castiel …

‘We don’t want to wake up Sam, right?’

Dean exhaled shakily, and nodded before swallowing noisily. Already putty in Castiel’s hands. The angel worked the front portion of the waistband on Dean’s underpants, freeing his penis and stroking along it with the flat of his palm. The hunter groaned involuntarily, flexing his hips into Castiel’s hand.

’Shhhhh!’ Castiel whispered as loudly as he dared. He didn’t know how Sam would take it if he found them in the act. He kissed quickly down Dean’s chest and stomach, the hunter raising his hips off the bench, trying to give Castiel more room to manoeuvre. But he didn’t want the extra room, there was something in the idea of being cramped between Dean’s stomach and the steering wheel that caught Castiel’s imagination.

He started licking, taking his time, savouring the taste of Dean, aware of Dean’s suppressed noises of pleasure, and the way he was going along with what Castiel wanted. How could this be wrong? He slid his mouth over the shaft, feeling the jolt that travelled through Dean, and the way his upper body strained to keep the wheel straightened.

‘Cas,’ Dean panted, his voice low, trying to keep the volume down. Castiel didn’t want to remove his mouth, so he lifted his hand and waved a finger for a moment, before returning all his attention to Dean’s groin, where he sucked and licked against the tender skin, working his hand into Dean’s boxers, finding the sensitive skin between his testicles and butt, and massaging it as he worked on Dean.

And then Dean was coming, hot and thick down Castiel’s throat, as Dean made an odd whining sound. As soon as the flow stopped, Castiel drew himself up and off his lover, looking at his handiwork as there was a noise from the backseat. He bobbed his head up, checking on Sam as quickly as he dared. Sam had unfolded his arms, and was beginning to rub his eyes with the heels of his palm. Castiel thought quickly. He could just zap Dean’s underwear and jeans back together, but he was worried about causing Dean any pain. Instead, he moved with lightning fast reflexes, putting Dean back away, zipping him up again, twisting the button closed, and reaching up for a swift kiss on Dean’s jaw before cuddling back in. The hunter pressed an arm around Castiel, holding him close, as though all they had done throughout Sam’s nap was mirror a Hallmark couple. In the backseat, Sam stretched and yawned.

‘Are we nearly there?’ Sam asked at the end of the yawn, and Castiel felt something on his upper lip, something wet. Dean answered, his voice steady, giving nothing away.

‘About five minutes from the town.’


They could hear Sam rustling papers and Castiel wiped a finger on the wet spot, licking it quickly as Dean pressed a kiss onto his head, through his hair. Were the other angels watching? Would they understand the significance of that kind of action, or overlook it on the fact that Castiel had oral sex with a human? With Dean Winchester, of all people? They drove through the town, with the angel worrying silently, as the brothers scoured the neighbourhood.

‘That’s her house,’ Sam broke the silence, waving his hand over Cas’ head, pointing at a house just ahead of them. He sat back as Dean pulled up, and Cas sat up reluctantly, as Dean turned to his bother.

‘You okay, man?’

‘Yeah. Yeah, I’m fine. You’re coming too, right? Both of you?’

Castiel didn’t understand why Sam was so reticent to meet the girl that Dean had described as his girlfriend, but Dean was, as ever, completely compassionate to his younger brother’s needs.

‘Sure. Lets go.’ Dean climbed out of the car, and Castiel scrabbled to join him, while Sam slid out of the backseat. They walked together through the uniform front yard, and up the small flight of porch steps. Sam rang the doorbell and smoothed his hair back in a nervous tic, and Castiel stepped closer to Dean, their arms grazing as they stood back slightly, letting Sam wait in front of the door. It opened, and a petite blonde woman stepped forwards. Castiel watched as her expression altered several times within a second. From surprise to elation, then to doubt and fear. Castiel looked at Dean, wondering if he would be able to interpret her reaction properly, but he was staring at Sam. And Sam was the first one to speak.


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