Chapter Text
Castiel cleared his throat and knocked on the door. He was irritated with himself for feeling nervous.
Irritation and nerves were both things he guessed he'd kind of known as an Angel, but not like this. Human emotions really were determined to kick his ass.
“Yeah?” came Dean’s voice from inside his room.
Cas pushed the door open. Dean was sitting on his bed, in the process of dismantling and cleaning one of his guns.
“Hey, Cas, what’s up?”
He sounded in a pretty good mood, which was a relief. Cas exhaled the breath he’d been holding.
“Hello Dean. May I speak to you about something?”
Dean raised his eyebrows, curious. “Sure.”
He put his disassembled weapon down next to him, and turned to give Cas his full attention. Dean was sometimes very nice like that. If you caught him on a good day he really was the best friend in the world.
“Um, it’s a little awkward,” Castiel began, coming further into the room and closing the door behind him. “I mean, it wouldn’t have been awkward before, but now I'm, um, well I’m aware that certain human interactions are typically a little strained, and there are some topics which are, well…”
“Cas,” Dean interrupted, not unkindly, “Seriously, spit it out, man. You can talk to me about anything, you know that.”
Cas nodded, looking at the floor, trying to remember the little speech he’d been practising in his head during his shower.
He scratched his forehead and just blurted it all out.
“Alright. Well, since I had sex with April, it feels as though I've, um, activated that side of myself.”
He paused, but Dean didn’t say anything, so he continued; “I’ve been sort of - looking into it a bit more.”
“Looking into it?”
“Yes,” Cas said, awkwardly pacing a little and coming to a stop by the table. He tapped his fingertips on the wood. “I've been watching pornography. And reading erotic stories.”
He didn’t look at Dean, wary of the reaction. He knew Dean enjoyed his fair share of adult entertainment, but he’d also made it clear to Castiel in the past that friends aren't meant to sit around chatting about that.
“Oo-kay,” Dean said. “Come across anything you like?”
Cas raised an eyebrow at the unfortunate turn of phrase, but neither of them commented on it.
“Yes, actually,” he answered. “Many things."
The sheer volume and variety of online pornography had astounded Castiel.
He’d started watching it as a way to slake the lust that had been awoken in him; surfing the sites with no expectations, just seeing what his body did and did not respond to. Some things definitely didn’t do it for him, although from an anthropological standpoint he’d found it all very interesting. And some of the things which had really got him going had intrigued him very much.
“What’s been interesting to me,” he informed Dean, “is that I’ve been responding more to the videos which feature just men.”
“You - you’ve been watching gay porn?”
“Dean, I’ve been watching all the porn.”
Dean smirked. “No wonder we haven’t seen much of you in a few days.”
Cas rolled his eyes to cover his embarrassment. That was another pesky quirk of being human - being embarrassed. So unnecessary.
“Okay, so, wait. Can I ask something about vessels then?” said Dean, adjusting his position on the bed so that he was leaning forward a little. “I mean, if Jimmy Novak was straight, doesn’t that mean you are as well by default, cause it’s his body?”
Cas sighed a little. It was always difficult to explain the nuances of vessel possession, and the saga of him and Jimmy's body was more confusing than most.
“Actually no, it doesn’t mean that at all,” he began. “For one thing, human sexuality isn’t just about what your body reacts to; there are psychological and emotional aspects at play too.”
Cas hoped he didn’t sound patronising; who was he to explain human shit to a human? But then again, he wasn’t totally convinced that Dean had all his facts straight when it came to sexuality and gender, likely because of when he was raised and who he was raised by . Besides which, they do say that the spectator sees more of the game than the player, so maybe Castiel was more qualified to talk on this.
“And secondly,” he added, rubbing the back of his neck, “Jimmy never occupied this particular body. This one is a copy. It was reconstructed specifically for me, if you remember. Jimmy’s in Heaven. I’m the only one who's ever been in here.”
Dean looked Castiel up and down, and then looked a bit sheepish for some reason.
“Right,” he said, then licked his bottom lip and looked away. “So, you wanted to talk about - preferring guys?”
Cas frowned. “It’s not that I’m worried about that. To be honest I was sort of expecting to find myself pansexual as a human. Angels have no gender or sexual orientation of course, and so I guessed I would be attracted to a wide variety of people. I was definitely attracted to April, and some of the women in the videos are very beautiful, and very sexy.”
Cas bit his lip, still finding the use of words like ‘sexy’ a bit foreign.
“But," he concluded, "it’s certainly the homosexual men I’ve been most excited by.”
Dean pursed his lips and nodded. “Alright.”
There was a short silence, and Cas knew the time had come to get to the point.
“So, I was wondering, do you think I should find a man to have sex with? To get it out of my system?”
Dean’s face kind of got stuck mid-expression at that, as though his brain had glitched. Maybe he was shocked.
So Cas expounded; “It’s really all I can think about, and it’s starting to become very distracting."
Dean seemed to shake himself out of whatever trance he’d been stuck in. “You're asking me if I think you should - date guys?”
“Yes. I’d really like to try it. I'd welcome your input on how to proceed.”
It certainly did seem to Cas to be a logical next step. He was keen to experience all that the human world had to offer, and physical sensations were at the top of the list.
Fizzy candy on your tongue, what happens to your stomach when you ride a rollercoaster; he wanted to know what everything felt like. And, latterly, that included anal sex. He really wanted to know what it was about it that made guys moan like they did in the videos, and made their eyes roll back in their heads.
“Cas, it’s - kind of complicated,” Dean told him. “I mean, with our lifestyle, you can’t really date anyone. You know, none of us can exactly bring people home to the bunker. What are you going to say when they ask what you do for a living? About your family? Your past? It would be all lies right off the bat and that’s no way to have a relationship.”
“Well, I guess I’m not really talking about a relationship, Dean. I’d honestly be happy with just some sex.”
Dean rubbed his forehead. “Right. But guys who are just in it for the fucking aren’t usually that nice, Cas, I mean what if you got into some trouble?”
Cas frowned. He knew that Dean indulged in casual sex fairly regularly, and so between him and Sam, he'd seemed Cas' best bet to help advise him on finding a partner. He was surprised that Dean was being this negative about the prospect.
“Trouble?”
“Yes. You’re a human now, and people are crazy. You could get hurt. Someone could take advantage, get violent.”
“Oh.”
Cas hadn’t thought about that.
He’d been thinking it would be nice to have a night of passion that didn’t end in him being stabbed by a Reaper, but Dean was right. It wasn’t only supernatural things that could be dangerous to him in these situations.
It wasn’t like he couldn’t handle himself. He had several years' experience of hand-to-hand combat under his belt, but he understood it wasn’t the same now. No grace, no blade, far less confidence.
He looked at the floor, feeling a little defeated and foolish.
Dean cleared his throat. “I mean really in this situation what you want is a friends with benefits deal.”
Cas looked up.
“You know, someone you already like and trust, who you could experiment with, and no one would be judging," Dean continued. "Exploring your sexuality should be fun, Cas. It should be with someone who cares about you. Not some random dude in a bar.”
Friend with benefits.
Of course that was what Castiel wanted, but it wasn’t possible. And now he felt impatient and frustrated as well as defeated and foolish.
“Well, that sounds an excellent idea Dean, but I have precisely two friends; you and Sam. And to my knowledge, neither of you have sex with men, so a 'random dude' seems like my only option.”
He shook his head, and was on the verge of a very human storm-out-of-the-room, when Dean’s quiet voice stopped him.
“To your knowledge.”
“What?”
“To your knowledge, neither of us has sex with men. And you don’t know everything, Cas.”
Now it was Castiel’s turn to have a brain glitch. He blinked several times. Dean was looking away from him, something strange and sad in his eyes.
“Dean. Have you - have you slept with men?”
Dean’s jaw twitched. Then he looked right at Cas. “Yes. Not lately. Not often. But, yeah.”
All of Castiel’s negative energy from before drained out of him, and was replaced by affection and care for his dearest friend. “I didn’t know that.”
“Yeah, well.”
Dean grabbed the parts of his gun, and the cleaning cloth, and stood up with them. He walked them over to his bedside table, quickly and expertly slotted the thing back together, and put it in the drawer. He turned back to Cas.
Cas cursed his inability to read social situations. What the fuck was he meant to say now? He licked his lips.
“Dean, I don’t want to overstep,” he chanced. “But - are you maybe, um…”
Dean let out a heavy sigh.
“Yes, Cas,” he said. “I’m offering, okay? I don’t want you picking up some diseased douchebag in a bar.”
The very suggestion of being physically intimate with Dean was making Cas’ skin hot.
The thought had threatened to enter his mind a few times over the years. Ever since he’d watched Dean kissing Anna, the notion of Dean’s body and its component parts had been poised to plague him. He’d suspected that it was extremely bad form to fantasise in that way about one’s friends, so he’d never allowed the thought to fully take hold. But here it was on the metaphorical table.
“But would you -” Cas felt his brow crease as he tried to word his question correctly. “Would you enjoy it? Or would you just be doing it to protect me?”
He clarified; “From the douchebags.”
Dean exhaled a small laugh, and Cas was relieved to see his whole demeanour become more relaxed.
“I would enjoy it,” he assured Cas.
Then Dean inhaled as if he was going to say more, but he didn’t.
So Cas filled the silence, paraphrasing something he’d read once in an article online. "You don't think that altering our dynamic in that way would have a lasting adverse effect on our friendship?”
Dean looked to be considering it. Cas really didn’t want him to change his mind about the ‘friends with benefits’, but he couldn’t do it if it meant Dean would be weird with him after.
“Our friendship truly does mean a great deal to me, Dean. Everything, in fact."
Dean pushed himself up from where he’d been half leaning against his bedside table. "Cas. If all the fights and the deals with the devil behind each other's backs haven't had a 'lasting adverse effect on our friendship', I think we can survive a bit of sex."
Cas smiled. "Well, I would certainly feel very comfortable exploring this with you. You know me better than anybody."
"Good. Okay. Great."
There was a pause.
"Do we - just - start now, or do we schedule in a time? I don't know what the protocol is."
Dean laughed at that, breaking the tension a little. "Me either."
“You never had a friend with benefits before?”
Dean pursed his lips. “I guess I have. But it’s always been sort of a ‘lost in the moment’ kinda thing. This is the first time I’ve had a pre-game discussion about it.”
Cas nodded, and decided to take the plunge. "Well, I have just showered, and we don't really have anything else to do, so I guess now would be an optimum time."
Dean pulled a strange face, then chuckled.
“I’m sorry,” Cas said, back to being irritated with himself. “Pragmatism isn’t very sexy, is it. It just seemed appropriate to seize the opportunity."
“Can we just talk a little first? Maybe set some expectations, some ground rules?”
“Of course, Dean, whatever you think.”
Cas sat down on the chair by the desk, waiting for Dean to start talking, relieved to yield to his expertise.
"Right,” Dean said, and moved to sit back down at the end of the bed facing Cas. “Okay, let me ask you this. When you picture yourself in scenarios with guys, do you see yourself as the top or the bottom of the equation?"
A fair question, and something that Cas had in fact been giving a lot of thought to, lately. Mostly while stroking himself in front of Cocky Boys videos.
"Well, I already know what it's like to penetrate someone of course, so I am curious to know how it feels to be the one penetrated.”
Cas couldn’t help but notice that the skin on Dean’s neck was flushing a little. Surely Dean wasn’t embarrassed by this conversation? Dean was very experienced, sexually, apparently even more than Cas realised.
“But I want to experience everything, so I suppose I would be interested in trying both."
"You, uh, you know what a flip-fuck is?"
"All the porn, Dean. Yes, I know what a flip-fuck is."
Dean smiled out the side of his mouth.
“Did you and April engage in any, uh, oral sex?”
Cas frowned. “No, unfortunately not. We used only our hands for foreplay while we were kissing.”
Dean swallowed. “But it’s something you’d be - interested in?”
“Oral sex? Yes, very interested. In giving and receiving.”
The thought of having Dean in his mouth, closely followed by the thought of Dean having him in his mouth, was causing Cas to have to shift in his seat due to - reasons.
Dean clearly noticed, judging by how his eyes flicked down to Cas’ crotch, but he was enough of a gentleman not to mention it.
"So, uh," Dean stuttered. "What, um, what position did you guys do it in?"
"Oh, well we did it twice…"
"Ooh, stud."
"...and the first time, she was on top of me. I can't say it lasted very long, I was somewhat overwhelmed."
It had indeed been a very overwhelming day. Cas had gone from being completely alone and virtually starving, to all of a sudden having a beautiful woman nursemaiding him and kissing him and seducing him. His body had gone into autopilot and done what an adult male body is designed to do in such conditions, which was a relief because Cas truly had had no idea how to properly make love.
"And then later we did it again," he continued, "and that time it was with me on the top. I was feeling a little more confident by then."
Dean smiled. Cas suspected he was trying not to laugh at Cas' naivety.
"I'm sure this is all very lame to you; you've probably made your way through the whole kama sutra."
"Not quite," Dean smirked. "I guess I've got a reasonable amount of kinky shit ticked off the ol' bucket list."
"Do you have a favorite position?" Cas asked, a little scandalised at being allowed to picture Dean in a state of carnal activity.
"Sure," Dean answered. "But Cas, sex is about what's good for -" he gestured between the two of them with a circular motion of his hand - "all parties involved. There's no point being in my favorite position if the other person hates it, you know? You find a chemistry and a rhythm and you figure out what works for you both."
Cas nodded, and exhaled.
"What did, uh, what did it feel like?" Dean asked, quietly. "Was it good?"
Cas swallowed. "It was unbelievable," he answered, honestly. "Sex is something I only ever knew about in theory. I had no idea that it was so - potent."
Dean rubbed a hand along his jaw. "Yeah," he agreed. "It's pretty powerful stuff."
"And April and I didn't even know each other," Cas added. "I'm sure it's even better when there's trust and - and a connection."
"Oh, for sure," confirmed Dean. "That's when sex is done right. I mean, one-night wonders are all well and good, but when you know someone, when they touch you and it comes with history and personality. You know, instead of hooking up with some random person who just happened to be there, you get to finally kiss someone you've been longing to kiss, and it's, uh…"
They looked at each other for a few seconds. Castiel’s body temperature had ascended, and his cock was getting very interested in proceedings.
"Alright, well, listen,” Dean said, suddenly, slapping his hands decisively on the denim covering his thighs. “You’re right - we should just seize the opportunity. So, let me go shower and then I guess we're doing this."
“Okay,” Cas exhaled, standing up.
He regretted standing up almost instantly, since Dean was still sitting down, and was therefore now nearly face-height with Cas’ semi erection. Cas took an awkward side-step away, as Dean slid off the bed and slinked out of the room without making eye contact.
____________
Sam was in the library, reading some ancient-looking book about god knows what.
"Hey," said Dean, wearing his 'dead guy robe', and rubbing his hair dry with a small towel.
Sam glanced up briefly from his book, but didn't give Dean his full attention. "Hey."
"Listen, can you do me a favour?" Dean said, trying to sound as cool as possible.
Sam did look up properly at that. "Yeah, what's up?"
"Can you make sure not to come by my room for like, an hour. Maybe two."
Sam frowned. "Uh, sure. Why?"
Dean shrugged. "Just - trust me."
With that, Dean turned to walk back to his room.
What a weird fucking turn this day had taken.
Dean was a little shocked to find that Cas wanted a male fuck-buddy, but he was even more shocked at how eagerly he'd volunteered for the vacancy.
Nobody in the world knew that Dean slept with guys.
It had only been a handful of times, and always in the back of a truck or in the bathrooms of a bar or dirty highway diner. Just to scratch an itch which would surface every now and then.
And yet he'd offered that information to Castiel with barely any hesitation.
Dean knew he'd changed since Purgatory. The change in him felt even more profound than when he came back from Hell. It was like he literally had nothing to hide any more, and not a single fuck left to give.
He'd spent a year doing nothing but running and killing, then he'd seen his brother on the very edge of death - AGAIN - and now all the Angels had literally fallen from literal Heaven. Ambiguous sexuality was the very least of his concerns.
And now Castiel, former Angel of the Lord and commander of the most powerful garrison of Heavenly warriors, wanted to explore gay sex.
The idea of Cas cruising bars and being vulnerable with a bunch of sleazy dudes turned Dean's stomach. If anyone was going to put their hands on Cas it was going to be him.
Ever since Cas had come out of that motel bathroom after returning from Purgatory, freshly showered and shaved and back in his trenchcoat, Dean had been screwed. He'd missed Cas so much, and the sight of him once again alive and well in front of him had been a lot.
He'd had a very vivid sex dream about Cas that night. They'd been under a tree back in Purgatory and Dean had been on top of him, slowly fucking him while gazing into his big blue eyes.
Yeah, this has been a long time coming.
Dean had had an extremely thorough wash in the shower, and was now very keen to get back to his room and hopefully blow Cas' mind.
True he was a lot more experienced with women than men, but he knew his way around all bodies, and he was feeling pretty confident. There was so much he could do to make Cas feel good, he couldn't decide where to start.