Fifty First Dates

Chapter 3

Castiel had waited until some time in the early morning for Dean to fall asleep so he could wipe the hunter’s memory of their disastrous date. Dean had sat up, glaring at him, but not speaking, for hours, before eventually turning in.

Castiel wasn’t sure what he’d done wrong, exactly, but he figured that maybe it was his declaration of love. Maybe Dean was having a hard time dealing with Castiel being so brazen so early on into this relationship. He hadn’t been able to help it, however, the words seemed to bubble up inside him, and he was unable to prevent them from escaping his lips. At least when Dean woke up in the morning, he would have no recollection of Castiel’s faux pas.

He was already imagining what they could do for their next date. Group activities were out, and Castiel was now aware that however they phrased it, it had to be clear to Sam that only Dean and Castiel were involved. Castiel wasn’t sure how to express that to Sam to make it absolutely clear that he was not invited, so he was trusting Dean to communicate with his brother.

He spent most of the night watching Dean sleep once he had wiped the previous day from Dean’s mind, careful not to get in the way as Dean shifted on the bed, his legs sliding between the sheets and his hands tucking further and further under his chin and his pillow. His lips parted as he settled, and Castiel watched in fascination as they moved soundlessly for a moment, as though Dean was speaking, calling out for him. Perhaps it was wishful thinking on Castiel’s part. He found it endearing when Dean would rub his head against the pillow in his sleep, as though he was looking for some comfort and the closest he could find was in the cloth-covered feathers below his head.

Castiel was filled with a desire to crawl onto the bed, balancing as he slowly made his way to Dean, slip under the sheets himself, and press up against Dean’s warm body, wrapping his arms around Dean’s torso and burying his head in the nape of Dean’s neck, breathing in his scent, which had hints of apple and cinnamon and something earthier, possibly a reflection of all the pie he ate, and all the outdoor work he did. Either way, Castiel found the smell comforting, just like he found Dean’s company comforting. He wanted to close his eyes, lay there beside the man he adored, and feel Dean’s hands close over his arms, stroking softly, sense Dean’s head turning before the feather touch of his lips found their way through Castiel’s unruly spikes …

Castiel didn’t move from where he stood. He knew he had to exercise caution when it came to Dean. There were limitations that Dean put in place to protect himself from getting hurt any more than he already had been in life. Castiel knew that, and he’d seen just enough of mankind to know they often put a wall up to hide behind, to protect their feelings from being damaged. It was one of the more fascinating aspects to Castiel, that humans were able to construct invisible barriers to protect invisible parts of themselves. If emotions and protective patterns were physical entities, Castiel presumed most people would walk around surrounded by ruins. But not Dean, Dean would be immersed in a fortress. Sam would possibly be skipping around in a meadow, by comparison.

Day eventually broke, and Sam was the first to wake, stirring easily as the first feeble rays shone through the ineffectual curtains. He squinted as he rubbed his face, and then peeked up at Castiel.

‘Morning Cas. Everything okay?’

‘Everything is fine, Sam.’

‘Cool. I’m going for a jog before Dean gets up, okay? In case he asks when I’m out. I’m assuming you’ll still be here when he wakes up?’

Castiel nodded, and looked away as Sam crawled out of bed in just his boxers, approaching his bag and rooting through quickly before pulling out his jogging clothes and throwing them on, unafraid of nudity around his brother and the angel. When he was in a loose t-shirt and jogging bottoms, he scooped up his iPod and waved quickly to Castiel, who nodded and continued to watch Dean sleeping, oblivious to Sam shaking his head in amusement. The moment the door closed softly behind Sam, the tinny echo of music coming out of his headphones cut off, and Dean stirred in his sleep, sitting up slightly, the sheets slipping slowly down his taut bicep, revealing the tanned, slightly freckled skin, and if Castiel angled his head the right way, he could just glimpse the slightly pinker skin of Dean’s nipple, tucked just under Dean’s arm.

‘Mmm, what time is it?’ Dean muttered, looking at Sam’s bed, and then flopping down. ‘Great.’

‘Sam’s gone jogging,’ Castiel spoke up quickly. Dean made an impatient noise, which could easily have been a gurgle.

‘Great. Well, while he’s gone, I’m going to grab a shower. Will you be okay?’

‘I’ll be fine, Dean,’ Castiel smiled warmly at the hunter, who missed the gesture as he stumbled from his bed towards the en suite bathroom. Castiel took advantage of Dean’s lack of awareness to observe how Dean’s underwear clung to his skin, the large bulge at the front, the flattering curves of his backside, the slight dimples at the top of his ass that Castiel had an irrational urge to bite.

‘Okay. We can talk about that date once I’m done, if Sam’s still out, right?’

Dean paused by the doorway and looked back at Castiel, who smiled as innocently as he could possibly manage.

‘Sounds good, Dean, I can’t wait.’

Dean nodded, and gave him the briefest of smiles before shutting himself in the bathroom. Moments later, Castiel could hear the sound of running water, and he sat gingerly on the edge of Dean’s bed, lifting the pillow that had been under Dean’s head and sniffing the material for the trace of Dean’s scent as he imagined Dean’s body in the dim bathroom, naked under the flow of water, his hands rubbing soap in to every inch of skin. He could faintly hear Dean singing, some recent pop song he wouldn’t be caught dead singing if Sam was there, and Castiel smiled as he realised that Dean was letting Castiel see a part of him that he wouldn’t even share with his brother. Making Dean forget the bad date had made Dean forget he was mad at Castiel also. Maybe there was even a chance that Dean would be more enthusiastic for round two?

Castiel put the pillow back on the bed just before the sound of the water cut off. Castiel knew that Dean wouldn’t be out of the bathroom just yet, he would want to brush his teeth and shave his face, which were human activities that Castiel certainly didn’t miss from his brief time without a Grace, though he did appreciate when Dean made that kind of effort. Castiel enjoyed the minty tang of Dean’s breath when they worked close together, and the smell of the cologne he worked into his cheeks. Dean’s various scents were heady and intoxicating for Castiel.

Dean eventually emerged from the bathroom with a small towel wrapped around his waist, the two ends barely meeting up along his legs, and though he pinched the material together tightly, Castiel could still see a thick, muscular thigh flashing every time Dean stepped forward. He knew Dean was probably aware of his staring, but Castiel couldn’t help himself. God had done a wonderful job when he created humans, and when it came to Dean? He was probably God’s most impressive project yet.

‘Hey, Cas? Eyes up here.’ Dean pointed to his face, before heading to the dresser drawers under the television and rooting through the clothes inside. It was a quirk that Castiel found adorable. No matter where the brothers were staying, or for however long, Dean would put his clothes away in the closets and dressers provided, while Sam would live out of his bags, sometimes strewing his clothes across the floor and furniture. Dean began dressing himself, and Castiel managed to tear his eyes away from the hunter, looking at the bedside table where Dean’s phone sat, a lead running between it and the wall. He waited until he felt the bed sink down, a sign that Dean had finally dressed, to turn back to look at him. Dean was bare-foot, his jeans and a shirt on, and his towel was now slung around his neck as he lifted a corner and rubbed it over his scalp. Castiel swallowed, as Dean smiled at him.

‘Sam’s probably going to be forever on his jog, wanna go get breakfast? I mean, I know you don’t eat, but we could grab Sam some granola after I eat something decent.’

‘Sounds good. Sam won’t be worried?’

‘Nah, I’ll text him,’ Dean leaned across Castiel to take his phone off the lead, and tap out a message, unaware of Castiel staring at him, at the way he concentrated on the tiny screen, as he used his large, rough hands to carefully handle the small handset. Another contradiction that made Dean so attractive to Castiel. He sent the message then spun the phone into his pocket, smiling at Castiel. ‘Give me a minute, and then we’ll go.’

Dean grabbed the socks he’d left beside him, and pulled them on his feet, before untucking his boots from underneath the bed and tugging them on too. He reached across Castiel again, not seeming to notice as Castiel inhaled the scene of shampoo as Dean’s short spikes grazed his face, and grabbed his car keys and wallet from the table.

‘Okay, I’m good,’ Dean announced, standing up and heading for the door of the motel room. Castiel followed quickly, and climbed into the Impala as a human would, while Dean sat in the driver’s seat. Dean paused, and turned to the angel. ‘So, how about we go for a drive first? Grab some breakfast in a while, and just drive for the hell of driving after that?’

‘Is this our date?’ Castiel asked as innocently as possible. Dean laughed, a deep belly laugh that shook his whole frame.

‘Right, we were meant to talk about that! Sure, if you want, Cas. Just text Sam and tell him to fend for himself.’ Dean passed his cellphone, and Castiel started tapping on the phone, glad that the Winchesters had taught him how to use these things. He sent the message quickly, and while Dean was concentrating on the road, began scrolling through Dean’s contacts. Apart from three contacts for Sam, and Castiel’s number, he still had old friends who had fallen by the wayside, like Garth and Kevin, and even his father. And the vast majority of his contacts were females. Castiel felt a stab of jealousy, deep within his gut. ‘You text him yet?’


‘What’re you doing now? Reading my texts?’

‘No, I wouldn’t.’

‘Cas, I was teasing. So, you wanna make a day of it?’

‘That sounds good.’

Dean nodded, his eyes still on the road. Castiel turned his head to watch Dean, glad that he could technically do that all he wanted during this drive. Dean’s profile was as well sculpted as the rest of his physique, his prominent cheekbones and his plump lips and-

‘I’m feeling pancakes, is that cool?’ Dean interrupted Castiel’s internal catalogue of adoration.

‘You’re the one eating, Dean.’

‘Did you ever try pancakes as a human? Because if you didn’t, you’re missing out.’

‘I’ll take your word for it, Dean. Watching you enjoy them will be enjoyment enough for me.’

Dean shook his head slowly.

‘Man, you don’t even know. At least you’re going to be a cheap date.’ Dean smirked, and Castiel frowned.

‘Is that supposed to be a good thing?’

Dean laughed again, that deep rumbling laugh that Castiel could feel through the leather-bound seat.

‘Oh, Cas,’ he smirked again, but didn’t elaborate on the thought. Instead, he sat forward, squinting at the horizon, and Castiel happily went back to concentrating on the way Dean’s hair looked fluffier after his shower and how silky smooth his skin looked, and imagined how it would feel to have the shaved bristles of Dean’s cheeks scratch against his own. ‘You still with me, buddy?’

Castiel shook his head, coming back around, out of his thoughts.

‘Sorry Dean.’

‘Don’t be sorry, we’re here,’ Dean nodded at a Mom’n’Pop diner. ‘Are you alright, man? You don’t seem like you, much.’

‘I’m just … glad, that you agreed to a date.’

Dean shrugged.

‘It’s pancakes and a mini road trip, Cas, it’s not a ring on my finger. Come on.’

Dean climbed out of the Impala, and headed for the sidewalk as Castiel stayed in the car, watching the hunter. Dean’s head was bowed slightly, and he walked with his knees apart, but even those imperfections were endearing to Castiel. He smiled to himself as Dean turned around and cocked his head at the door of the diner, and Castiel scrabbled to open the car door as he realised Dean was impatient for his meal. He joined the hunter on the sidewalk as Dean locked the car and nudged Castiel with his shoulder.

‘Seriously, man, what’s up?’

Castiel looked up at Dean, his eyes locking onto Dean’s pink lips, imagining the kiss they had shared the day before, and how much he would love to do the same again. Or even take it further than the brief, chaste kiss that Dean had given him the day before. And though Castiel vocalised none of his thoughts, Dean seemed to understand, as though he could read the flavour of Castiel’s intentions in the air between them.

‘I need to eat, Cas, okay? And after, we’ll go somewhere and … talk.’

The way that Dean said that final word, the way his voice seemed to croak and break up on the single syllable, it said to Castiel that maybe Dean was more willing to be physical with him than he’d imagined, that maybe talk was code for what Castiel truly wanted. Because he talked all the time with Dean, and their relationship was strong thanks to their profound bond, but Dean must have known that Castiel’s proposal to date meant that he wanted another element to their relationship. So Castiel nodded, and walked with Dean into the diner, uncomplaining as they sat on the counter stools for Dean to order. Castiel posed with a cup of coffee as Dean ordered a short stack with a heavy side of bacon, and sipped from his own coffee cup.

‘Has Sam got back yet?’ Dean leaned on the counter with one arm, and nodded at his phone, that was still in Castiel’s hand. Castiel passed it over to him, rather than check for messages himself, and Dean smiled briefly before concentrating on the screen. ‘Yeah, he has.’

Dean started tapping on the phone again, reaching across the counter and grabbing his coffee cup, holding it by the body as he sipped absent-mindedly on the hot liquid. Castiel grabbed his own cup, sipping his own drink and trying not to wince as the abundant taste of molecules passed over his tongue. He knew he only had to last until Dean had eaten, and he was sure he could push himself to cope with the coffee until then. Dean’s breakfast was placed in front of him, as he pocketed his phone, and picked up his fork, stabbing into the pancake and biting on the fluffy yellow pancake before groaning. That groan shot through Castiel’s system, spiking the rhythm of his heartbeat and warming his stomach, making his pants tight around his groin. How could Dean have so much effect on him with one primitive, guttural noise?

‘This is so good man, you sure you don’t want?’ Dean asked with his mouth still full.

‘It’s fine, Dean. You, um, you have a little syrup,’ Castiel pointed to the corner of his mouth. Dean swiped at his mouth, on the wrong side, and Castiel’s face lit up as he smiled at the hunter’s misunderstanding. He leaned over on his seat and stroked the corner of Dean’s mouth with his thumb, catching Dean’s eyes which seemed to darken at the action. Castiel paused, his thumb still hovering by Dean’s face, the smear of syrup across the pad of his thumb. Had he made a huge mistake in being too forward? But then Dean caught his thumb in his mouth, the soft skin enveloping him up to the knuckle, his teeth grazing against the sensitive area and his tongue reached out and licked the syrup away. It only lasted for a mere second, but Castiel was even more desperate for contact with Dean after the brief moment. He pulled his hand away, shaking slightly, reliving the feel of Dean’s slightly dry lips and the moist softness of his tongue, the way Dean’s eyes had closed almost automatically as he acted on impulse.

They didn’t speak about what had happened, or make any eye contact with the local patrons. If anyone had witnessed those few seconds, Castiel knew Dean did not want to acknowledge it. Humans were strange in that way.

Dean didn’t take long to finish his meal, throwing down some bills onto the table and clapping a hand on Castiel’s shoulder.

‘Come on, let’s go find somewhere.’

Dean’s touch sent tingles all over Castiel’s body, but he managed to stand and follow Dean to the door, fighting the urge to let his fingers graze against Dean’s. At any moment, he would push this too far, and Dean would no longer want to know. He waited it out as they climbed back into the car, and Dean drove off again, his eyes scouring the local landscape again.

‘Can I ask you something?’ Dean broke their silence, still driving, only looking at the road.

‘Of course Dean, you can ask me anything.’ Castiel said enthusiastically.

‘And you’ll be completely honest?’

‘Why would I lie to you?’

That earned Castiel a quick look, before Dean turned back to scanning the horizon.

‘How long have you wanted to do this? Like, how long’ve you been into me?’

Castiel sucked in a deep breath. He wanted to answer poetically, something that would lodge in Dean’s memory. I have loved you forever, since before you existed. I’ve loved all the atoms that eventually led to creating the man you have grown to be. I have loved you before your mother even knew that she had the capability of carrying you.

‘I’m not sure, Dean,’ he spoke slowly instead, covering up the need to spout poor rhyming couplets at the man. ‘We’ve always had such a significant bond, but when it became something more? Maybe it was when you refused Michael, and stood up to Zachariah, when it was clear you would stand up for everything you believed it. Especially as I knew, by then, that you would stand up for me.’

‘That’s a pretty long time to have feelings that you don’t act on.’ Dean observed.

‘I suppose it is, for a human.’

Dean nodded, processing how long that scope of time really was for a being like Castiel.

‘So, I guess us dating, that doesn’t make us gay, does it? If anything, it’s beastiality.’

‘I choose not to think of it that way, Dean.’

‘How are you thinking about it?’

‘That you have a beautiful soul, and I’m fortunate to have met you.’

Dean stopped the car, looking at Castiel with a frown on his face, his features otherwise closed to exposing his emotions. The walls were up, Castiel noted sadly. He also realised they were parked in the outskirts of a field, out in the middle of nowhere.

‘Cas,’ Dean eventually muttered, his voice low and urgent and causing another reaction in Castiel’s vessel. And then he slid across, crawling over Castiel’s body, pushing down on the angel with his weight and heat before pressing his lips against the angel’s, sliding his hands along Castiel’s sides as his tongue probed into Castiel’s mouth, and Castiel almost froze in disbelief. Dean was voluntarily kissing him, the way he had fantasised about a thousand times, and it was everything he had hoped for, rough skin with gentle touches, caring hints in a passionate embrace, and Castiel could feel himself shaking as he slid down in the seat, unable to control himself as a thousand explosions set off along his body. Dean’s hands skimmed down, hooking around the back of Castiel’s knees and pulling them up onto the seat so they were laying along the leather, flush against each other, the kisses never seeming to end as Dean threaded his legs through Castiel’s, grunting and moaning as his body started rocking naturally against Castiel’s, and Castiel could feel his eyes rolling back in his head, even as a small voice of doubt started in the back of his mind.

Dean wouldn’t do this, would he? It wouldn’t take a brief compliment and a moment in a diner to lead to this point, would it? He could feel the doubt growing even as he felt Dean’s erection pressing against him. How was this going to happen? How did two males connect on a sexual level? Castiel hadn’t given this enough thought.

‘Oh, Cas,’ Dean mumbled, and kissed down onto Castiel’s neck, his tongue flicking against Castiel’s stubble, his body even more insistent against Castiel’s, which had began to respond without Castiel’s awareness, grinding against Dean as though they could somehow merge into one person. Dean’s breathing was harsh, rasping, and he pulled his shirt off quickly before going back to Castiel’s neck, his hands sliding down Castiel’s shirt and working on the buttons. Castiel bucked against him, groaning involuntarily himself, as Dean chuckled quietly. ‘All in good time.’

The whisper sent shivers down Castiel’s spine, and dissolved the negative thought he’d been having that Dean was purely going through the motions with him. Those four words felt like confirmation that Dean wanted this as much as Castiel did. With a renewed confidence, Castiel worked his own hands down, along to Dean’s waistband, tugging at Dean’s belt and eventually getting the button undone, the zipper down.

‘Are you sure, Cas?’ Dean breathed, propping himself on his hands, leaving Castiel’s neck alone. Castiel looked up at the human above him, his eyes scanning along Dean’s torso, to the dark hairs that began near his belly button and continued passed where Castiel’s were still holding onto his jeans. He didn’t remember feeling the hair on his fingers before, and was visited by the urge to stroke the line now. ‘I mean, we have all the time in the world-‘

‘You’d want a second date?’ Castiel gasped out, his own breath still erratic. Dean laughed quietly.

‘How about we don’t call this a date? We call this some fun after breakfast.’

Castiel’s finger slid along the trail of hair as he considered this, noticing that even the lightest of touch along the area made Dean’s stomach jump up, like the patch of skin there was sensitive.

‘Are you sure?’ Castiel pressed. Dean smirked, and bent down to press his lips to Castiel’s once more, just briefly, lifting up again straight away; the motion almost as though Dean was doing press ups over the angel.

‘I’m sure, Cas. You don’t agree to date your best friend without understanding it’s more for the long term.’

‘But you said-‘

‘Cas, relax, okay?’ Dean began kissing his neck again. ‘Just relax, baby. All in good time.’

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