Fifty First Dates

Chapter 6

After Sam walked in on Dean and Castiel in their compromised positions, the evening had consisted of an awkward silence, briefly interrupted by some stilted conversations on neutral topics, and Sam crawling into bed as soon as the alarm clock on the side table clicked to ten o’clock. As soon as he did, Dean cleared up the plates and pans from his dinner and climbed into his own bed, cuddling up to Castiel, who was still on the bed. Castiel felt nervous yet excited to be so close to Dean so late at night, after being so connected that evening, and he snuggled in to Dean’s chest, which felt firm and muscular and everything that Castiel had been hoping for. Dean kissed his hairline lazily, and Castiel’s chest thrummed as his heart rate spiked. If he had been asked at that moment what his own personal heaven looked like, he would have described this scene, barring Sam’s presence and bed. A small, darkened room, the faint smells of food lingering, and a sense of security, love, trust and belonging all radiating from the man who would welcome Castiel into his arms.

It felt too good to be true, that Dean was the one persevering now for their relationship. It gave Castiel hope that his feelings might be reciprocated. He watched as sleep came over Dean and his grip slackened as he drifted off to sleep. Castiel remained close to the hunter, his eyes raking over Dean’s features in the dim light that filtered through the curtains. At the strong jawline dusted with stubble and the faint lines appearing around Dean’s eyes, at the bump in Dean’s nose, which was slightly off-centre, and his full lips. Even without the scant light, Castiel knew Dean’s face so well from watching him so closely, but that didn’t stop him from seeking out the opportunity to do so up close.

Castiel spent the entire night laying in Dean’s arms, noticing that the hunter didn’t move around in his sleep the way he normally did. He decided it meant that Dean took comfort from him as well, and he snuggled closer to the hunter, watching as the room became lighter, the thin curtains doing little to remove the impact of the sun. Castiel heard Sam stir, and zapped himself across the room. He wasn’t sure where Dean stood on telling Sam about their relationship. He wasn’t sure where he stood on discussing the relationship with Sam either. Castiel had been avoiding the taller hunter, to try to minimalise Dean’s potential embarrassment.

Sam nodded his morning greeting as he sat up, and rubbed his eyes with the palms of his hands.

‘Good morning Sam,’ Castiel responded, as though Sam had spoken. Sam glanced at the alarm clock with puffy eyes, and rolled out of bed.

‘What’ve you been up to all night?’

Watching your brother sleep, and falling even more in love with him.

‘I’ve been thinking.’ Castiel shrugged.

‘Hmm? About what?’

‘Angel stuff.’

Castiel was glad to have that excuse to use whenever he wanted. Neither Dean nor Sam ever really questioned him on his angelic agendas, and he was always careful to be vague if they ever tried. The truth was, he was rarely in contact with Heaven. He had no real reason to be, and it was dangerous for Castiel to try. Sam didn’t probe further, but prepped for his jogging session instead.

‘So, I’m going for my run, I’ll be back in an hour. In case Dean wakes up, okay?’

Castiel nodded, and waited until Sam had banged the door shut, and he heard footsteps pounding outside to remove his suit and crawl back into bed with Dean, who was now curled to one side. Castiel snuggled up to Dean’s back, revelling in the gentle warmth that radiated from the hunter, and he rested his head against Dean’s, stroking his arm slowly, occasionally kissing the hunter wherever he could reach. Castiel knew he wasn’t going to get the opportunity to greet the hunter in this way again, and he was trying to embrace the opportunity while it was in front of him. He felt Dean begin to stir, and pressed another brief kiss on the hunter’s shoulder.

‘Where’s Sam?’ Dean asked quietly, his voice clogged with sleep. Castiel was happy that the first words out of Dean’s mouth were not an admonition regarding the way he had woken. He felt a stab of hope that Dean was asking after his brother to be sure that they had some privacy. The angel pressed another gentle kiss onto Dean’s cheek before he answered.

‘Out on his early morning jog. I didn’t join you in your bed until he’d left about ten minutes ago.’

Dean shifted in the bed, turning to face Castiel, raising an arm and pulling the angel close to him as he did so. Castiel could barely fight the smile that erupted as he realised Dean was thinking the same way he was. Dean’s next words confirmed it.

‘I guess that gives us fifty minutes to fool around before he gets back.’

Castiel frowned slightly, wondering exactly what context Dean was applying to ‘fool around’, but he soon forgot it as Dean rolled onto him, pressing his heavy body close to Castiel’s, and he began to pepper Castiel’s face with kisses. Castiel laughed in a mixture of relief and joy, and he felt his body turn to jelly under the hunter’s. He traced his fingers down Dean’s side, loving the way it made Dean’s body jolt against his own, as Dean continued kissing every millimetre of Castiel’s face, every eyelash and inch of cheek and stubble blade was being give attention, and Castiel could feel his body reacting, embracing every second of Dean’s attentions.

‘This,’ Dean pressed a sloppy kiss to Castiel’s cheek, high up on the cheekbone, ‘was’ he caught the soft skin under Castiel’s eye, ‘the’ Dean moved towards Castiel’s forehead, ‘best’ he caught his lips on the tip of Castiel’s nose, ‘idea’ Dean’s lips skimmed up to an eyebrow, ‘you’ve’ Dean twisted around and nipped gently on Castiel’s ear lobe, and Castiel began to pant, ‘ever’ Dean licked down into a haphazard kiss on Castiel’s jawline, ‘had.’

Dean moved back up slightly, and kissed on Castiel’s upper lip, and Castiel kissed Dean’s lower one, already sliding his tongue into Dean’s mouth, biting at his lips. Dean responded with enthusiasm, shifting even closer to Castiel, twisting their legs together, grinding his hips and his early morning erection into the angel. Castiel felt his body shaking underneath Dean’s persistence, his own erection beginning to throb, and his fingers grazed further down Dean’s side. Castiel was beginning to lose track of his thoughts, and he clung on to Dean’s hips as they moved back and forth. Dean then surprised Castiel by pulling away slightly, ending their increasingly frantic kissing, though Castiel could still feel Dean’s warm breath on his face.

‘Do you wanna get naked?’ Dean whispered, looking into Castiel’s eyes. Castiel wasn’t sure what Dean was asking for, what he was intending by putting that notion between them, so he shook his head and kissed the hunter again, who was only too happy to respond, kissing Castiel with renewed enthusiasm and rocking against him once more. Castiel could feel Dean’s erection pressing down on him, and without really considering what he was doing, he slipped his hands into Dean’s boxers, and took hold of his penis. Dean stopped bucking to move his hips, never breaking their increasingly desperate kisses. Castiel started to realise what he’d done, and tried to work out what was going to happen now. Was Dean going to yell at him? Would he understand that Castiel had let his vessel take over for a moment? Dean interrupted his worried thoughts.

‘Cas, move your hands,’ his managed to whisper while still kissing Castiel. Castiel understood that Dean wasn’t impressed with Castiel’s actions, and immediately let go, moving his hands away from the hunter. Dean nibbled on Castiel’s lower lip.‘That’s not what I meant.’

There was a small pause. Castiel felt confused. What else could Dean have meant?

‘What did you mean?’ Castiel asked, his breathing still erratic. Dean smirked down at him, his face almost transformed as his hands skimmed down Castiel’s body slowly, leaving a trail of heat along his sides. Castiel stopped kissing Dean, concentrating on what Dean was doing, on the way his fingers seemed so lazy, yet knew exactly what he was doing, as he peeled Castiel’s underwear off. They stopped, and Dean whispered throatily,

‘Okay Cas, you’re going to do exactly what I do, okay?’

Castiel nodded slowly, feeling almost drunk on the effects of Dean’s affections. Dean’s fingers continued their lazy journey up to Castiel’s groin, and he wrapped both hands around Castiel, waiting for the angel to reciprocate. Castiel tried to copy Dean’s actions, brushing his hips and sliding the elastic of Dean’s underwear down, taking hold of Dean as well. There was a burning sensation in Castiel’s chest, and he wondered what Dean was up to, what he was planning.

‘This is what I did before,’ Castiel pointed out. Dean smiled lazily, his eyelids half-closed.

‘Mmm-hmm,’ and Dean began kissing and licking along Castiel’s jawline, as his hands started sliding up and down Castiel’s cock. Castiel started doing the same, thinking how strange it felt to have Dean’s hands on him, yet how much he wanted Dean to continue. And how strange Dean felt in his hands, warm, slightly wet, hairy, and softer than Castiel would have expected. Dean stopped kissing him, lifting his head up, and Castiel looked back, into his eyes, neither of their hands missing a beat. And Castiel felt a tightness in his chest, like he wanted to cry, though he wasn’t sure why he would want to. He wanted to tell Dean in that moment how he felt, how much Dean meant, how consuming his love was, but he didn’t want Dean to stop. He was scared that Dean wouldn’t want to know if he told him, that there would be no chance of any further dates, even with the memory wipes.

Dean’s hands changed direction, his fingers probing and rubbing, and Castiel tried to match the actions, enjoying the way Dean’s body reacted to his touch, the way he bucked and shivered and began kissing Castiel again, along his neck and collarbone, groaning incoherently in between and they both began humping, matching the rhythm of their hands. Castiel’s eyes were rolling back into his head, and for a few minutes he was lost in Dean’s hands, only just managing to copy everything Dean was doing.

And then something changed, which Castiel hadn’t been expecting. Dean had grunted loudly, and something warm and wet flowed over Castiel’s hand and onto his stomach as Dean collapsed onto him completely, feeling like a deadweight against Castiel’s vessel. And Dean’s hands had flown off of Castiel, which the angel immediately missed. There was an aching need in his penis, and Dean didn’t seem able to continue what he’d started. And Castiel wanted to see what would happen, to see if he would react in the same way. He moved his wet, sticky hands onto himself, and continued pumping himself, bucking into his hand movements the way they had been doing. Dean lifted his head slightly as he realised what Castiel was doing.

‘Sorry, Cas,’ he mumbled. Castiel was becoming breathless.

‘It’s okay, Dean. Help me,’ and he felt under the blankets for Dean’s hand, accidentally smearing Dean’s come along his arm before grabbing Dean’s hand and shoving it back on himself. Dean’s touch did more for Castiel than his own hands, and Dean began sucking on Castiel’s neck as he built his pace up.

And then it was all over, and Castiel felt like something was exploding, the same warm-and-wet sensation all over his hands, and himself, and the bed, and Dean. Castiel had groaned loudly too, feeling a release from the aching sensation that had been building up. They laid silently for several moments, as Castiel realised that his heart-rate was erratic, and that they were both still holding on to his body. He let go, winding his slippery, sticky fingers into Dean’s, moving their hands to the side of the bed, tugging Dean onto him further. Castiel was the first to break the silence this time.

‘Dean?’ Castiel’s voice was hesitant. Dean raised his head, a dopey expression on his face. ‘What did we just do?’

Dean smiled lazily, and kissed Castiel gently on his mouth.

‘I thought you wanted it.’

Castiel frowned, feeling confused. Had he wanted that? He wasn’t sure what he had wanted, except to be closer to Dean. Dean’s reactions had been unpredictable, and although Castiel had felt an overwhelming need to continue, he was wondering if he had enjoyed it.

‘Hey, Cas?’ Dean sounded conversational, like nothing major had occurred between them. He leaned on an elbow, looking down at Castiel with an expression Castiel would lose his grace for. It looked almost like Dean was as besotted as Castiel, in that moment. ‘Awkward question, but before Sam comes back, could you work your angel magic, clean this up? Sam’ll ask about it otherwise.’

‘Clean what up?’ Castiel felt perplexed, as Dean raised the two hands that were woven together, covering in semen. It took Castiel a moment to realise what Dean was really asking for. Was he feeling ashamed as well? Castiel couldn’t detect that emotion in Dean, though it was burning through his own vessel. They were still naked, their pants around their ankles, and Castiel couldn’t enjoy the sensation of Dean pressed against his vessel. ‘Oh, okay.’

All the evidence of what they’d just done disappeared, like it had never been. Dean’s skin no longer felt sticky and sweaty and slick, but soft and warm and dry. But Castiel couldn’t wash away the strange sense of guilt inside him, or the nagging feeling that with Dean, this was only the beginning. He felt the need to get some clarity with Dean over what could be coming up for them.

‘Dean? Please don’t laugh but I have to know. How do two men have sex?’

Dean burst into laughter anyway, his stomach slapping against Castiel’s, creating that buzzing sensation in his chest again. But Castiel was affronted, he’d been asking so that he could be more prepared than he was for the morning’s activities and Dean was treating it like some big joke. Did that mean sex with Dean was off the cards? But then Dean was pressing another gentle kiss to his lips, and Castiel sank back into utter confusion.

‘I’ll show you tonight.’ Dean growled, kissing Castiel again as the motel room door opened, and Sam stepped in, surveying the scene in front of him quickly. Dean bearing down on Castiel, their underwear falling out of the foot of the bed, the sheets rucked up along their bare legs to their knees. Neither Dean nor Castiel seemed aware of just how much they were exposing their relationship to Sam at that moment.

‘Ugh, guys, please. Get a room.’ He greeted them, averting his eyes to the ceiling.

‘We had one.’ Castiel informed Sam, barely paying him any attention before reaching up to Dean and kissing him in return. Sam stumbled across the room, still trying to avoid looking at his brother and the angel.

‘Yeah. Look, I’m going for a shower, can you guys stop that please? I mean, I’m happy for you and everything, but that is too damn weird.’

‘You’re too damn weird,’ Dean bit back, his lips and tongue bumping into Castiel’s mouth. They heard the bathroom door slam shut, and Dean raised his head, smiling down at Castiel with an unexpected dopey expression on his face. Castiel wanted to keep the image of Dean looking like that forever. ‘It’s fun messing with him.’

Castiel shook his head slowly, wishing he could feel as playful as Dean did. Clearly, Dean thought something good was happening between them. But he was feeling increasingly confused, and was starting to wish for some time to himself, just to consider what was going on, how their relationship was developing.

‘We’d better stop here, I don’t want to upset Sam.’ He eventually muttered, to which Dean rolled his eyes and pressed closer for another kiss, lowering his voice again as he responded.

‘We’ve got a little while before Sam comes out of the shower.’

‘I’ll get carried away,’ Castiel confessed. Because yes, he was confused and he wasn’t sure he had even liked what had just happened, but Dean just had to look at him and Castiel would agree to anything. And Castiel was well aware that the morning was just the tip of the iceberg. Dean’s next words were something that Castiel would ordinarily love to hear, but at that moment they were terrifying.

‘I don’t care.’

Castiel had to think fast, and in a moment of blind panic he flashed them both out of the bed, into their own clothes and made sure they were as far apart as they could be in that small, confining room. He watched as Dean looked around, bewildered, before he realised what happened, and glared at Castiel.

‘Dammit, Cas!’

‘Sorry, Dean. I’ll make it up to you, I promise.’ Castiel blurted, as though that would fix the almost suffocating feeling inside him. Before Dean could answer, the bathroom door swung open once more and Sam walked out, holding his hand over his eyes as though he was avoiding seeing anything untoward.

‘Are you guys done yet? We need to get going.’

‘It’s fine, Sam.’ Dean answered, beginning to pack his clothes, suddenly avoiding Castiel’s eye contact. Maybe Dean was ashamed, after all. Castiel watched as they both packed up their bags, pocketing their phones and handguns, until Sam looked up and smiled nervously.

‘Cas? Can you give us a hand?’

Dean left the room, leaving the door gaping open as he stomped away down the stairs. Sam looked at Castiel with a pitying expression.

‘He’s mad at me, isn’t he?’

Castiel blinked back, surprised that Sam would apply Dean’s bad mood to his actions. Castiel was grateful for Sam’s interruptions. He needed to re-evaluate.

‘I’m sure he’s not, Sam.’

‘Well, he was in a good mood when he was in bed with you.’

Castiel looked away rather than answer, pretending to scan the room for anything that might have been left behind.

‘Is that everything packed?’ he asked instead. Sam clapped a hand on his shoulder.

‘You don’t have to hide it from me you know, Castiel. I can see what’s going on with you and Dean. Just, try and behave a little bit when I’m in the same room, is that cool?’

‘We should go and find Dean. I think he wants to go.’

Sam squeezed Castiel’s shoulder gently, before leaving the room, and Castiel took a few moments for himself, looking at the bed that so recently, Dean had broadened his world on. He knew that Sam would be encouraging Dean to talk downstairs, trying to brighten Dean’s suddenly sour mood, and Castiel wanted to give them the time to do that, as well as take some time for himself. But he didn’t want to take too long and upset Dean further, either. He resolved to going to find them and letting them know he was taking some time for himself. He’d reuse the angel excuse if he had to.

He found them outside of the Impala, talking about Sam’s date from the previous night. Castiel naturally drifted over to Dean, brushing close beside him. Dean curled his fingers back around Castiel’s, stepping even closer, with no commentary from Sam. Castiel couldn’t tell if that was a good thing, or whether they were both distracted from their conversation.

‘It was ten. Besides, her relationship with her brother was creepy. There’s a reason why our research showed they were married.’


Sam nodded, as Castiel tried to understand what Sam could possibly be implying about his date.

‘Exactly. But come on, we need to find a new case. If you can stop thinking about each other naked for five minutes?’

Castiel gave Dean’s fingers a squeeze, and then let go, knowing he would want to sit behind the driving wheel, and Dean bent close, his breath tickling Castiel’s ear.

‘It’s every five seconds, not every five minutes.’

Castiel swallowed as Dean climbed nonchalantly into the car, like he hadn’t said anything outrageous. Castiel needed all his resolve to fight the urge to climb in the car, on Dean’s lap, and explore his mouth all over again.

‘I’ll come and find you later. I have things I need to do.’

‘What things?’ Sam asked. Castiel had a momentary wish that Sam would butt his nose out. His response was abrupt.

‘Things that concern my family. I’ll see you soon.’

And before Castiel could doubt himself, or Dean worry about onlookers, he pressed a gentle kiss onto Dean’s face, and flashed out, into the bunker, and Dean’s bedroom.

He hadn’t been lying when he said it concerned his family. Castiel was beginning to wonder if the depravity he was experiencing with Dean was going to be the final nail in his coffin, the one thing that would cut him off from Heaven completely, and utterly. His brothers and sisters were fine with Castiel being in love with Dean, especially as for the most part, it hadn’t been reciprocated, but now that it was, would sex with a human - even if it was Dean - mean that he had no chance of ever being redeemed?

And for Castiel, Dean and Sam were another kind of family. Like when humans got married and left their parents to become parents themselves, to start their own offshoot of the bigger family. Dean was the man he wanted as his partner for life, and Sam was his slightly irritating brother-in-law, in Castiel’s mind at least. Would Castiel’s chosen family compromise his actual family?

He sat on Dean’s bed, legs splayed out in front of him, debating over and over in his head what to do. And then he decided that maybe he needed to educate himself, because Dean had been vague about what would happen between them if they continued a physical relationship. He pulled his cell phone out of his pocket, and began searching in Sam’s beloved internet for whatever facts and diagrams he could find about what they had done.


Hours later, Castiel’s head was full of facts, films and stories he’d come across online. He now had a name for what he and Dean had done that morning, and a vague knowledge of what would happen if they pursued a physical relationship. Castiel didn’t understand it much at all. He was also convinced, as he had increasingly been through his research, that his father would never approve of Castiel being intimate in that way with Dean. And though he couldn’t erase what he’d done, or the guilt that came from it, he could still erase Dean’s memory of it, to stop their relationship developing too fast. Castiel should have erased the day before as well. He would do it that night, when he listened for Sam and Dean and came to the place they were staying. At least by repeating their first dates over and over, Dean wouldn’t push anything too far.

Eventually, he heard voices in the bunker, and realised that for once, Dean had come to him. Castiel could make out their conversation, something about strikes and no game, and after a couple of minutes, Dean came into the room, pausing when he saw the angel on his bed. And then he was striding across the room, kicking his boots off, climbing onto the bed beside Castiel, kneeling as he wrapped his arms around the angel and kissed him enthusiastically. Castiel’s head was too full of his research to respond properly, and he pushed Dean away, keeping the hunter at arms length.

‘What, are you off me again?’ Dean’s tone was good-natured, but Castiel knew that he was annoyed by the lack of enthusiasm. Instead, he brought their foreheads together, as though they could read each others thoughts that way.

‘No, Dean. Of course not. But I want us to slow down. You said you were happy to wait for Cassie and Lisa. Can you wait for me?’

‘Of course, Cas. We can still make out though, right?’ Dean sounded both surprised and hopeful. He didn’t even question the implication that Castiel was likening himself to Dean’s more successful relationships. And as much as Castiel was hoping for Dean to be more open-minded about the possibility of the two of them together, he felt more confused than ever, even as he nodded. Did that mean he could stop erasing Dean’s memory? Did he have everything he wanted? Dean seemed to be reading Castiel’s sense of defeat correctly, because his tone softened. ‘How about we do something else?’


‘No, trust me, Cas. Sit forward a little and close your eyes.’

Castiel regarded Dean with some suspicion, before he shifted forward, off of the pillows, and closed his eyes, giving his trust over completely to Dean. And then he felt the soft touch of Dean’s weathered fingers on his face, barely touching the skin, gliding along all the contours set by Castiel’s features. They swept around onto his back, their speed changing. Sometimes he used only one finger, sometimes all five, sometimes close together and sometimes splayed out. But everywhere Dean touched left a trail of heat, and shook Castiel to his core. He wished Dean was better at explaining himself, because to Castiel, these were the tender touches of love, and he craved that love from Dean so much.

There was a pause, and Castiel almost begged for Dean to continue, but then he heard the hunter moving, felt the bed dip as he shifted to sit behind the angel, his legs splayed out around Castiel’s, their thighs touching, Dean’s groin pressed into Castiel’s butt, and Dean continued to trace across Castiel’s back, and up his neck. Time seemed to stand still, and all the existed was Dean’s touch, as Dean’s fingers gently massaged the sensitive skin under Castiel’s jaw, and Castiel fell back against him, completely relaxed.

‘This feels wonderful, Dean,’ Castiel’s voice had a dreamy quality to it. Surely, with an innocent-yet-intimate touch like that, it would make up for the earlier mutual masturbation? Castiel even hated the term. He forced it from his mind, too involved with the way Dean was caressing him to worry about their morning activities.

‘Good, it’s meant to,’ Dean pressed a kiss to Castiel’s temple.

‘Thank you,’ he whispered.

‘Sure.’ Dean finally stopped tickling along Castiel’s throat, and wrapped his arms around Castiel’s shoulders instead, pressing close to Castiel. When Dean was like this, how could anyone not love him? Castiel was completely besotted.

‘I meant, for agreeing to give us a try, for saying you’ll be patient with me, for everything.’

Dean leaned closer, leaning his chin against Castiel’s shoulder.

‘Yeah, well. Hey, you wanna go do something? I mean, we haven’t even had a date yet.’

Castiel jerked forward, his eyes blinking open, all thoughts of bliss removed for a moment. They hadn’t technically had a date in those last forty-eight hours, Dean was correct. They were closer than ever, and Dean seemed more open to a relationship than ever before, but it was true, they had not yet had a date, in Dean’s eyes anyway. Maybe he should have a new plan, and keep up the intimacy until Dean just admitted that Castiel was his boyfriend, and then Castiel would never have to worry again? He leaned back into the hunter once more, snuggling close, enjoying the scent of Dean’s aftershave and the heavy warmth of his arms.

‘I’m happy here right now, Dean. Just sitting here with you.’

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