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Fifty First Dates


Supernatural fandom: Destiel. Dean has agreed to go out on a date with Castiel. Castiel misunderstands what Dean means by one date, and uses his angelic powers to persuade the hunter to have more.

Erotica / Romance
Siobhan Collier
4.7 7 reviews
Age Rating:

Chapter 1

All Castiel’s dreams had come true. Dean had agreed to see him. As in, dating. As in, giving Castiel the fully human experience that he’d been looking forward to.

It had been an awkward conversation, after hours one night in a motel room, Sam fast asleep and snoring in the bed furthest from the door as Dean drank a beer.

Castiel was fascinated as Dean drank his beer. The way the muscles in Dean’s biceps flexed and strained, the way his lips curved naturally around the bottle’s opening, how Dean’s tongue flicked out into the bottle neck before he raised the base of it, and tipped the liquid in his mouth, as though he could fully coat his tongue, tasting the beer before drinking it. Castiel imagined that kissing Dean would be much the same, the seal of his mouth, his tongue protruding forward, tasting the kiss before it truly started, letting Castiel have a taste of him before anything happened, before Dean’s tongue flicked back in his mouth, or ran itself over Castiel’s teeth, the way their mouths would move together, almost grinding against each other as Castiel’s tongue moved of its own accord, twisting against Deans, a hint of alcohol bound to be on the hunter’s breath. And how would Castiel taste to him?

Castiel imagined Dean’s firm grasp on his hips, Dean’s fingers moving slowly around, palms sliding onto Castiel’s ass as his fingertips dug into the flesh, pulling Castiel’s form against his own, as Castiel’s fingers skimmed effortlessly through Dean’s short brown hair, the bristles tickling as they brushed his fingers, the way his fingers would lock at the back of Dean’s head, pulling him closer, not allowing Dean to leave the kiss as Castiel’s stomach dipped and peaked like a car on a roller coaster and his heart burned with so much intensity that Dean would surely feel it through his thin t-shirt. Castiel could imagine Dean panting, fighting to get enough breath without breaking the connection between them as Castiel struggled to control his own breathing, which would accelerate as the fire in his chest grew. And then their bodies would start mimicking their joined mouths, flexing together, working out a rhythm, fighting against the limitations as Dean would stumble forward, trying to brace Castiel against a wall, or a table, or the nearby bed …

They had been talking in lowered voices, trying not to disturb Sam, the intensity of the conversation making them practically murmur.

‘Humans have very complex mating rituals, I’ve noticed over the years. You all like to believe that you’re the more advanced generation, but it’s not true. There are repetitions that occur, it just depends on which style is more acknowledged.’ Castiel was trying to make the whole thing clinical, too worried to expose his feelings just yet. Dean grunted, and Castiel took that as his signal to continue talking. ‘I don’t fully understand where the distinctions come from, but I know some people prefer to announce themselves as a couple, and eventually declare themselves betrothed. And once they’ve married, they finally have intercourse.’

Dean nearly choked on his beer, sitting forward in his seat and swiping a rough hand across his mouth, his lip moving slightly as it caught on his palm. Castiel forced himself not to stare, so he could keep his thoughts on track and explain further what he meant.

‘And there are people like yourself, who will have sex with several partners in a row, who see it completely separate to a relationship. Who don’t even seem interested in a relationship.’

Dean raised his eyebrows, his forehead crinkling as his brilliant green eyes were exposed. Castiel knew that this expression meant Dean was surprised, but Castiel didn’t immediately understand why. Dean didn’t speak, and Castiel knew he wasn’t going to interrupt until Castiel had explained himself fully.

‘Then I’ve noticed, there are those who seek a partner. They may be with their partner for one night, or a week, maybe even a year, but they’re the ones unsatisfied with their lot. So after the night, or the week, however long, they look for another partner, someone who will fill the void they believe that they have. That’s what I’ve noticed about humans approaches to courting.’

‘Sometimes it’s not that black and white, Cas. And there’s all kinds of relationships out there. It depends on who you are, how the person you’re with defines themselves, what you’re trying to get out of the situation, whether you’re on the same page. Some people get married to the people they thought were going to be one night stands. Some people never get married.’

‘I don’t think I understand, Dean.’

‘Well, like, you mentioned me. And you’d be right, sometimes, most times, sex is just sex. Okay, it’s not just sex, because it’s sex, you know? It’s one of my favourite things to do, and most of the time, I’m just looking for someone willing to join in, to enjoy it for what it is, no expectations that I’d even be there in the morning. And I’m lucky Cas, there’s a lot of women out there who are okay with it, so long as you spell it out. But I’ve had relationships too. I was with Cassie for a few years. I keep going back to Lisa. And when I was with both of them, sex with anyone else was off the cards. Sex with the two of them was off the cards until they made it clear it was what they wanted. And I was happy to wait, Cas, because they meant something. And if it took a whole week for them to decide to sleep with me, it was fine.’

‘What made you decide to treat Cassie and Lisa differently?’

Dean chuckled, lifting the beer bottle again, lips sealing the bottle, tongue darting forward, oblivious to the small shiver it set off in Castiel’s spine, or the increasing buzz within Castiel’s chest that made his stomach burn. His fingers were fighting to stretch forward, to remove the beer bottle, to replace it with himself and re-inact the same scene he’d been imagining for weeks.

You just know, Dean had said. It’s a gut instinct, or a mutual agreement through conversation. Like the desire for sex was there, but there were signs of possible friendship too, where you wanted to know the dumb things like favourite colours and favourite meals and how they take their coffee. You didn’t want to do that with just anyone. The mundane nature of that kind of conversation was only interesting when you had that level of understanding.

Castiel asked Dean how he took his coffee.

It took Dean a moment, before he sniggered, lowering the now empty beer bottle and clapping Castiel on the shoulder, and telling him it didn’t matter, he’d never expect the angel to get him a coffee. Castiel hadn’t responded straight away, his gaze dropping to Dean’s hand on his shoulder, the way his blunt nails dug in slightly, the tight grip of Dean’s fingers, the bruised and scratched knuckles that never seemed to fully heal before splitting open again, the intense heat that radiated through the trench coat, the suit jacket, and the shirt, right onto Castiel’s skin. All his senses seemed to pool there, or in his groin, making him shift slightly into Dean’s touch. And then Dean had spoken, articulating in his usual clumsy way his thought process as he realised that Castiel had intended the subtext, and how personally Castiel must have been taking the conversation. Castiel wondered if it was the fact he’d even attempted such a human way of communicating that Dean said the words he’d been imagining. Or a variation of them, anyway.

‘Well, gee Cas … I mean … you know … I haven’t really - because it’s not … is that what you … you know?’

Castiel had shook his head slowly, not fully understanding what Dean was trying to encapsulate in the words “you know”. Dean tended to use that phrase when he was expressing the notion that his feelings were more than evident in his actions and didn’t need the gravity of words applied to them, that much Castiel knew. He just wasn’t sure that Dean’s “you know” matched Castiel’s “you know” however much he wanted that to be the case. And then Dean had shrugged, letting go of Castiel’s shoulder, his fingertips grazing down Castiel’s arms and unknowingly causing a tidal wave of sensation erupting in goosebumps down the path his contact made.

‘Black. Strong. Sugar depends on how many nights I’ve already gone without sleep.’

‘Dean, I-‘

‘I know what you meant, Cas. So, what are you asking for here?’

Dean’s expression was blank, the only hint of an emotion on his face was a slightly tic in one cheek. Castiel watched the twitching muscle, imagining trying to calm it with his mouth. He made himself concentrate, because Dean didn’t seem entirely opposed to the idea of them together. If he expressed this correctly, Castiel would be able to have the kind of relationship with Dean that he’d been asking for.

‘I would like to experience a date. Or a series of dates.’

‘So you want me to hook you up with someone?’ Dean folded his arms across his chest, his t-shirt wrinkling slightly as his pectorals stood out, highlighted in the dips and stretched material. Castiel made himself push away the image of licking them, nibbling them, tracing the contours of Dean’s chest and stomach with his hands, following their progress with his mouth. He would worship Dean, if he had the chance, angelic duty be damned.

‘No, I don’t wish for a “hook up” Dean. I would like to experience a series of dates with someone who you described. Someone I have a friendship with, who-‘

‘Who you can make coffee for?’ Dean interrupted, his eyes now scanning Castiel’s face. Castiel sat up straight, hoping that Dean’s search of his expression yielded the correct results. This was the moment of truth that Castiel was longing for, and now it was here, the bubbling feeling in his stomach was threatening to spill over. ’Sure Cas. Make me coffee in the morning. We’ll work the rest out later.’

Castiel had beamed, as Dean stretched, and scratched his stomach before standing up, his t-shirt rising up slightly and exposing Dean’s flat stomach, and the hint of a curve of muscle leading down into his jeans, one of his abs disrupting the otherwise small skin. Castiel could see a few wisps of dark hair along the edge of the exposed flesh, and Castiel noted that for his next fantasy about Dean, he would need to include the faint trail of dark fuzz that stretched from Dean’s belly button down passed the waistband of his pants. Castiel’s eyes flicked up, and he caught Dean’s expression, the dimpled marks in Dean’s cheeks coupled with his thinned lips indicated that Dean knew exactly what Castiel had been thinking. And then Dean had said goodnight, and gone to sleep, leaving Castiel to try to understand if it had been okay to look at Dean that way. Castiel waited until Dean was asleep as well to step into the bathroom, remove his human clothes and stand in the shower, running the water and reliving all his fantasies, holding his own body with a touch he imagined Dean would have. Rough hands, but soft caresses, a tenderness in the way he explored Castiel’s body, the confidence that Dean would have in knowing what would set Castiel off, turn him on, and lose the function of his human legs. He often fantasised about Dean in this way when the Winchesters were asleep and oblivious to just how depraved Castiel had come.

Castiel was dubious that Dean would wake up and forget the whole incident, but the next day, Castiel was aware that Dean was watching him every chance he got. Castiel watched him so much, it was obvious to him when there was a difference with Dean. It was just unfortunate that Dean had almost totalled the Impala during one of their many lingering gazes. Sam had insisted on driving, as Dean was clearly distracted, and Castiel found Dean staring at him in the side mirror.

That night, Dean had sat up in the next motel’s kitchenette, under the guise of researching the case he and his brother were working on, and when Sam had turned in for the night, and fallen into a deep sleep, Dean brought the conversation up.

‘So, did you get me coffee?’ Dean smirked as he spoke, his eyes dancing with humour. Castiel had barely left his side, he knew what the answer would be.

‘Forgive me, Dean. I could find some, if it’s important to you.’

‘No, it’s good.’

‘I know you like a strong black coffee, sugar content increasing as your sleep deprivation builds.’

Dean’s smirk grew into a full smile, and he looked away, eyeing Sam’s prone body cautiously. Castiel took the welcome break in conversation to marvel over the perfection of Dean’s earlobe, how the curves of each part of his ear seemed to flow together, to naturally lead on to the next section. And how every millimetre of Dean’s ear would feel as Castiel grazed his teeth over it. Castiel tried to remind himself that he was getting erotic over Dean’s ear, and Dean would not appreciate it if Castiel’s human body revealed his thoughts.

‘So, say we’re on a date, what would we be doing?’

Castiel shrugged awkwardly.

‘We would be on a date.’

‘Yeah, Cas, I got that. What would you want to do?’

‘Date you.’

Dean gave Castiel a strange look, his eyes narrowed and his mouth scrunched together in a way that made Castiel want to stick his finger in there, to make Dean suck it, sliding it into his mouth and out again. He had to stop with the inappropriate thoughts, because there was more to this situation, for Castiel, then just sexual contact. He wanted a relationship with Dean, he liked the idea of finding out what colours Dean preferred and the pictures he would see in an ink blot test. He wanted to hear Dean discuss his feelings towards Sam, and towards himself.

‘Do you not know what people do on dates?’ Dean asked softly. Castiel shook his head. ‘Well, it depends on who’s on the date, but most people like to go to a fancy restaurant, dressed up real nice, and they talk while they eat, share a bottle of wine, get to know each other, that kind of thing.’

‘We already know each other,’ Castiel mused, and Dean smiled, looking down at the floor as he folded his arms again, his bulging biceps straining against his built and buffed chest, and Castiel felt a stab of desire as he imagined himself sandwiched between Dean’s chest and arms.

‘Well, some people go to movies and spend the entire time making out with each other, ignoring the entire reason they’re there. That’s always fun,’ Dean laughed, and Castiel’s eyes were caught by Dean’s perfectly straight, white teeth. There was nothing that Castiel could see that rendered Dean anything less than an example of a perfect human being. No wonder Castiel’s father loved humans so much, when humans like Dean existed.

‘Would you take me to the movies one time, maybe?’

‘One time? How many dates are you expecting, Cas?’

‘How many are you willing to give me?’

Dean clearly hadn’t been expecting Castiel to give such a direct answer back, because he reeled in his seat slightly, before straightening his features, trying to give the appearance of a poker face.

‘One date, Cas. Let’s take it one date at a time.’

The days passed in much the same way, the constant eye contact, and then at night, once Sam was asleep, the conversations about what they would do when they finally got the chance to go out, just the two of them. Castiel liked listening to Dean’s low voice as he described all manner of dates that he’d been on, trying to give Castiel some idea of what he would enjoy best for their first time.

The problem was, Castiel wanted to do them all. He wanted to do more. He wanted to show Dean the infinite possibilities that came with amorous relationships with angels. They could travel through space and time and infinite realities. They could change their matter or lose it entirely. Cas could show Dean his favourite Heaven, and the truth of Earth and human history. Or they could sit on the Impala talking and sinking beers, go bowling, walk on a moonlit beach, go on a roller coaster at Lunar Park, go dancing. The possibilities stretching on and on for Castiel, with only one certainty. He wanted Dean there every time.

But what if Dean came back to his usual self, and suddenly lost interest? What if Castiel made a mistake one time? What if there was some other reason why this didn’t work out? What if the hunting and the civil wars in Heaven broke them apart for good?

And then Castiel remembered a movie that Meg had watched with him in the psychiatric ward one day. Where a pretty blonde woman could never remember the romantic gestures of her partner, but he tried every day to make a difference in her life. He decided, as underhand as it might be, as much as he could wish that Dean would remember each and every second of the dates he had planned, that he would take this option. That he would repeat their first date over and over, in different places, different times, different realities; whatever it took to keep Dean his. He may have had an eon to live, but his time with Dean, he knew, was precious.

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