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Craving You

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College seemed to follow a steady routine:





Tacos (Tuesdays)

More tequila

Sometimes sleep

It was difficult to put into words the mixed feelings he had on his time at university so far, but despite the weirdness, Castiel Milton knew he was enjoying himself. He’d given the campus clubs a try. He’d given a few joints a try. He’d eaten his fair share of college-approved foods, and had put on that inevitable “freshman fifteen.” He’d definitely even given the nightlife a try, or continuous tries since he was now three years into his degree and still found himself going out every so often with his friends.

College wasn’t exactly what he’d pictured it to be. All throughout his schooling his teachers had ranted and raved about college being the most prestigious time of his life yet here he was, taking courses from professors who taught strictly based on memes. Yes, there was a level of prestige that went with being at a university, but sometimes that prestige faded when he saw the masses coming to school dressed in pajamas.

He liked his school though, the University of Nevada, even if he didn’t look the type that’d want to live Las Vegas. But something about the place made him excited. It wasn’t like his college was located directly on the bustling strip, surrounded by hotels and casinos but it did bring a certain atmosphere that he believed other universities wouldn’t be able to offer.

When driving over from California to move into the dorms, Castiel had been optimistic about his time away at college. He hoped that starting fresh in a new environment would break him out of the shell he’d been living in and that he’d be forced into more social events because he had no other choice but to get out there and make friends. Most of all he’d silently hoped that he’d at least be able to befriend his roommate. They’d been matched online but Castiel had been too nervous to reply back to the welcoming email he’d received from the other boy.

To his relief, he was paired with a roommate he clicked with. From the moment he’d stepped into the room, Dean Winchester was a solid part of Castiel’s life. His boisterous voice, sturdy handshake, and confident posture had drawn Castiel and all his shyness in like a moth to a flame.

Dean had introduced himself to Castiel as a self-proclaimed “geek with an unhealthy obsession with my car and if you can’t get on board with that, we should probably request a transfer now.” Needless to say, Cas stayed. (He loved Dean’s ‘67 Chevy Impala and all the ‘nerdy’ things Dean was into).

They’d been roommates for three years now, choosing to stay in the dorms since Dean had a full ride to the University, housing included, and Castiel couldn’t imagine living with anyone other than the green-eyed man.

He liked his life on campus and it helped that he had his best friend (aside from Dean) Hannah living so close too.

She and Castiel had gone to high school together and then subsequently the same university though they’d never actually talked in high school. Despite that, they grew extremely close during the first few weeks of college when they only had each other. Now they thought of each other as family, which is why Castiel didn’t feel so shitty as he woke up that morning laying on a hard, unforgiving surface.

For a brief, panicked moment he suspected he’d fallen asleep somewhere embarrassing—like the room of the guy he’d attempted to go home with the night prior, but when he inhaled the familiar scent of warm vanilla sugar, he knew with certainty that he’d bothered Hannah into letting him crash on her floor instead of having to explain to Dean why he was such a mess the night before.

Even the events from the night before were a bit of a mess in Castiel’s mind. He hated nights when he got as plastered as he did because the mornings after were always the worst. He usually didn’t drink enough to wake up dehydrated and bordering on liver failure. He usually just spent the nights dragging his sloppy drunk friends back to their dorms, cleaning them up, and tucking them in before making his way back to his dorm to then only get a few hours of sleep before the room filled with god-awful amounts of sunshine….


Last night he’d been on a mission of sorts. It was embarrassing to even think about now how hard he’d convinced himself it was a good idea. How he’d had to encourage himself (repeatedly) that he did indeed need one more shot of liquid courage—why’d he go with tequila?

He really wanted to pretend that last night hadn’t happen. Or more so that it hadn’t ended the way that it had. First steps in pretending it didn’t happen was to avoid talking about what did happen.

The sunlight that currently hit his face with an unforgivable brightness was enough to tell him that it was only a matter of minutes that Hannah would be waking up and forcing him to spill. He weighed the pros and cons of actually facing her questioning or going back to his own room. With leaden arms he groped around for his phone and held it close to his face to reveal the time. He’d be pushing it but he figured with the blackout curtains Dean insisted on having and the fact that it was about an hour before Dean usually woke up on the weekends, it would be safe for Cas to slip back into their room and sleep for the rest of the day, unquestioned by his even nosier best friend.

When Castiel pulled himself upright from the ground he gazed over to his friends’ bed seeing her fast asleep. Not wanting to wake her up, he quietly pulled himself off the floor and made his way to the front door.

He made it back to his and Dean’s room in merely ten minutes, smiling when he heard his best friend’s dead-asleep snores. It meant he didn’t have to talk about any of the events last night and his feelings on said events. Without much preamble he shoved off all of his clothes until he was down to his boxers and nearly nose-dived into his bed, sighing happily at the feeling of his cool sheets on his aching body. He was dead to the world in a matter of seconds.

When Castiel awoke it was to the sound of video games on a low volume and the glow of the television screen in their dark room. Dean was always courteous about not waking Cas when he was sleeping—Castiel was inherently not a morning person.

Quelling his rolling stomach and pounding head, he laid in bed listening to the sound of gunfire from the speakers, knowing Dean was without a doubt playing one of the old Call of Duty’s in preparation for the newer one coming out soon.

It was out of no other desire than to not be a bum in bed all Sunday that he slipped off of his bed, pulling his blanket with him, and plopped down into the beanbag chair beside his best friend on the futon. Because Dean was a righteous and thoughtful man, the lights in their room stayed off and the volume of the game stayed low.

Dean was pretty adamant that Sundays be spent strictly bumming around in boxers and eating cold leftovers on their futon while watching an entire Netflix series in one shot. It was the one day of the week that Dean never let anyone over to the dorm, unless that someone were his younger brother Sam or Hannah, and it just stayed the two of them all day. Despite trying to tell himself that it wasn’t his favorite day of the week, it was definitely Cas’s favorite day of the week. He’d always anxiously look forward to having Dean all to himself, just comfortably in each other’s presence.

It’d felt like that for Castiel for as long as he could remember. From their first weekend together, awkwardly eating Panda Express on their newly purchased futon, fumbling over which questions were appropriate to ask each other in their newfound friendship—Castiel had felt completely at ease in Dean’s presence. Dean was just one of those people that others wanted to be around and Castiel would probably always remain at the top of that list.

He looked away from the television screen for a moment to peer over at the man in question. Dean was already staring at him in return; the game now paused on the screen. He didn’t say anything, just looked Castiel over before he pulled out his phone and pressed a few buttons before pulling it to his ear.

“I’d like to place an order for delivery.” Oh bless his soul Castiel thought, feeling his stomach rumble. He loved that he and Dean didn’t even have to speak to communicate anymore. But what literal pile of garbage did Castiel currently look for Dean to jump straight to caretaker mode?

“Yes—my name is Dean. Oh you remember me? Awesome.” Cas laughed at Dean’s conversation with the hostess. It was perhaps a bit of a problem that certain restaurants knew them by name now… Maybe he and Dean did eat out a little too often. It still didn’t stop them from ordering takeout though.

“Yup, that sounds right. Pad Thai, Broccoli Beef, and four egg rolls.” There was another short pause in Dean’s phone call as he likely heard the total for the food.

“Cool. Thanks.” Dean muttered before hanging up.

From the cocoon of blankets he’d somehow knotted himself in, Castiel croaked out a pathetic, “I worship the ground you walk on.”

His voice was rougher than normal. What he wouldn’t give for some sort of mojo to zap a water bottle into his hand whenever he needed.

“Here. Water.”

Silently thanking all Gods for making Dean the most wondrous human to ever walk planet earth, Castiel greedily reached for the bottled water his roommate offered him. “You’re too good to me.”

“I know. I should request a transfer, find someone who doesn’t need to be constantly taken care of.”

Dean smiled over at Cas with amusement. He always seemed to enjoy the mornings that Castiel was the most hung-over, much to Cas’s chagrin and this morning seemed to be no exception. Castiel must have really looked like hell this particular morning if the devious smirk covering his best friend’s face was anything to go by. It wasn’t fair though. Castiel always looked like shit in the morning and he just so happened to look like burnt shit the mornings after drinking. Dean however had a tendency to still look like a male model no matter how he woke. The only way the tanned, freckled faced man ever showed signs of being a little bit hung over in the mornings was his hair being pressed against his face in odd angles. It wasn’t fair.

So, Cas tried to bring him down to his peasant level.

“I cleaned up your puke not even two weeks ago. It was blue and had chunks.” Cas deadpanned, narrowing his eyes in playful contempt until Dean cracked an even wider smile.

“Fine! I’ll keep you.”

Humming noncommittally, Castiel snuggled back down into his spot, pulling the blanket around his head. He was smiling ear to ear but he knew by the placement of his blanket that Dean wouldn’t be able to see it.

“Stop talking now.” Cas mumbled from his little nest, because he knew his pretend sassiness never failed to make Dean smile.

“Love ya too, buddy.”

Cas watched Dean play through more of the video game’s campaign, neither man bothering to make any small talk. Even when the food arrived they silently went about the space finding what few clean silverware they had and sat back down in their spots to eat. Before long they were stuffed (though they’d probably be hungry in another hour or so) and content to just stay in each other’s presence not needing to fill it with idle chatter.

Cas liked that he got to be around this side of Dean when very few others could. Dean always found himself leading conversations, staying animated and lively to make sure no one was left out in social gatherings. He’d go round and round talking to everyone and making them laugh, never leaving room for silence. It was something Dean felt compelled to do, he’d once told Castiel, because if Dean could steer conversation then it meant no one could ask him too many questions and that meant not needing to divulge parts of his past he’d rather leave unsaid.

He’d told Castiel about it all roughly six months into their friendship, opening up to him in a way he hadn’t with many other friends. He’d described growing up with his younger brother Sam and being forced to raise him after their mother had been killed by a drunk driver when Dean was only four. He’d told Cas about his father’s anger problems, taking it out on both the young boys until Dean was six and a social worker took them away after Dean’s teacher asked about his bruises.

Dean told him about growing up with Jody and later Bobby who loved and cared for Dean and Sam, setting them up on their path of success. But he’d also told Cas of the few and far between visits with his biological father, the man having flittered in and out of rehab later to die at the hand of his vice. It made sense why Dean didn’t want to share his origins and Castiel respected his privacy, never breathing a word of the life young Dean had lived, even to their closest friends.

Dean was a great man, even though he seemed to think otherwise. He was kind and thoughtful, never asking for anything of anyone. Castiel knew he could trust Dean with anything, and knew that if he asked for something within reason Dean would follow through. Castiel trusted him completely. Over and over he’d tell Cas that he was family and those words… they meant more to Cas than he knew how to explain since he didn’t have much in the way of family. Biological family that is.

He knew Gabriel wasn’t his biological father. He knew that technically Gabriel was his uncle and that his mother Anna had been diagnosed with terminal cancer when she was still pregnant with him. He knew that Gabriel had never wanted children but when Anna entrusted Castiel over to him in her will Gabriel refused to hear of another one of his siblings raising the baby. Castiel also knew that the doubt Gabriel’s siblings placed on his ability to effectively raise Castiel was what led Gabriel to cutting off his family and creating a smaller unit with just the two of them.

Castiel knows Gabriel isn’t his father but he thinks of him as such and refers to him as such. Maybe his parenting choices weren’t always the greatest. Perhaps Castiel had a few too many cavities growing up since Gabriel didn’t seem to understand that ice cream and other sweets were not in fact a part of the food pyramid. It was possible that Castiel had seen a few more scantily dressed women walking shamefully out their front door than other kids saw growing up. And yeah, the advice Gabriel gave him some of the time was a little dodgy but he did his best. Never once did Castiel go hungry. Never once did Gabriel say that he didn’t have time to work on homework with him or take him to the park.

Gabriel showed up to every parent teacher conference and he sat second row for every school performance. He hung up all of Cas’s artwork on the refrigerator and kept every single memento Castiel ever made in school. Even now Gabriel checks on Cas every day and calls him on Thursdays just to hear his voice. Castiel loves him immensely and loves that it had just been the two of them against the world all his life. It has just made him happier to grow his family, person by person. Now he has Hannah and Dean (and Dean’s brother Sam) as part of the people he can call his family too.

Suddenly pulled from his thoughts, Castiel found himself having to use more energy than he currently possessed to sift through his blankets in order to pull out his phone that had just buzzed three times.

Speaking of family.

Hannah: Are you all right, Castiel?

Hannah: Please tell me that you’re alright. I’ve been worried about you all morning. You were more upset last night than I’ve ever seen you but you wouldn’t tell me why.

Hannah: If I don’t hear from you in five minutes I’m going to message Dean.

Cas: I’m alright. I’ll tell you later, I promise.

Hannah: I understand.

Castiel really didn’t want to talk about last night. It was more out of sheer embarrassment that he just wanted everything that had happened last night to go away. He’d made a complete idiot out of himself, not to mention he’d been completely plastered. He wishes he could blame it on Balthazar but really it was Castiel’s own damn fault that he’d gone out.

He’d just been… itching lately for… something. Every day he just found himself wanting and wanting… wanting things he’d never had before. He was twenty-one years old and…

God damnit. He was twenty-one years old and he was a virgin to boot.

It’s not that he was saving himself. That was never the case. He just… he never had an opportunity. He’d been shy growing up and had never known many people, let alone met anyone who had been mutually interested in dating. The years just ticked by and he kept on being a virgin. There really wasn’t anything he could do about it.

But lord, have mercy, did he want to.

He craved touch, just as he figured most of the population does. He found himself fantasizing more and more about how it would feel… how it would be… how everyone seemed to be so driven by such a carnal act. Why was he still missing out on something that brought so many people such pleasure?

He wanted to change that.

He wanted to change it so badly but he just didn’t know how. So when one of his friends, Balthazar, had said “frat party” Castiel’s downstairs brain had taken control. Little Cas thought of it as the perfect opportunity to get what it wanted and what a fucking mistake that had been.

To be outright denied on his first and only attempt at sexual conduct was more mortifying than Castiel had ever imagined it would be.

A thick, heavy knot still settled in his stomach and he knew it wasn’t from the hangover. He wanted to fix this. He wanted to never have to go through a night like that again… walking back to his friend’s dorm with snotty, drunken tears rolling down his face as he realized just how undesirable he really was.

No. Next time he tried to hook up with someone he’d know what he was doing. He would never again embarrass himself with awkward virginal fumbling. He wanted to be the type of person that partners came crawling back for… that craved him in ways he didn’t know possible. He wanted someone to be driven mad with desire for him.

But he had to learn how to be desirable first. He had to learn the right ways to please someone before he could leave them wanting for more.

He just didn’t know how….

He needed someone to teach him. But where was he going to find someone like that? His first thoughts went to a strip club… but… he didn’t have the money for that. And dear lord, he’d been watching porn for years and that clearly did not help him in the slightest if last night were anything to go by. Ideally, he’d just go to another party and find a random person but…. He wasn’t going to make that mistake again.

It needed to be someone who wouldn’t judge him for being a virgin or make him feel like an idiot for wanting to learn how to give pleasure. It needed to be someone he trusted… How was he going to find someone like that?

He found himself asking one of the two people he could ask for advice about this.


“It lives!” His best friend exclaimed loudly, like the obnoxious butthead he could be. Castiel threw the blanket that was beginning to suffocate him onto the floor and sat upright on the beanbag chair.

“I hate you.”

Dean just smiled. “I know. What’s up?”

He was still playing his video game cussing at the screen each time he was killed by an enemy. And as his friend played, Castiel wondered if he should even interrupt him. Were his problems even that important? He figured the safest person to ask would be Dean. He wasn’t exactly open about his sex life but Castiel knew he had one… surely his friend would be able to steer him in the right direction.

“Can we talk?”

“Uh? Yeah?” Dean quickly paused the game and threw his controller aside, seeming to sense the uncertainty in Cas’s voice.

“You… you know how I went out last night… to Mick’s party…”

Tension formed between Dean’s eyebrows as he nodded to Castiel’s question. “Yeah? Did something happen?”

“Well, kind of. I met a guy.”


“But… it didn’t end well.”

Dean’s face paled. He was concerned. “What do you mean?”

“Uh—Arthur, his name is Arthur, and I had been talking which lead to you know… kissing. Oh and he’s Mick’s roommate by the way.” Castiel knew he was doing a shit job of explaining himself, as Dean’s face seemed to grow more worried. Still Castiel trudged on trying to be thorough. “So uhm… after a while he invited me back to his room…”

“Look at me.”

Cas’s eyes snapped up to Dean’s. His roommate’s green eyes were burning into him. “What?” Castiel asked in concern.

“Did he lay a hand on you?”

“What?” He could feel Dean’s eyes searching and scanning all over him, looking for something.

“I swear to God if he forced you to do anything you didn’t want—”

“No! No!” Cas threw his hands out and gripped his friend’s forearm. “Oh, Dean. I’m sorry. No it was nothing like that. I swear.”

Dean looked him over a few moments more, not exactly satisfied that Castiel was telling the truth. “Okay,” he said when he seemed to calm down a touch. “Go on.”

“So we were going to his room with the intent of, you know…”

Realization dawned on him and Dean’s face suddenly contorted into a grimace. “Oh! Dude, I don’t need to know about your sexcapades.”

“—And things were getting more heated.” Castiel tried to proceed. If he didn’t explain his dilemma to Dean now, he probably never would.


Dean tried to flop back against the couch and grab for his controller. It made Castiel suddenly feel panicky. If Dean wouldn’t listen to him about this then who could Cas tell?

“Dean, please! I have a point.”

His friend looked over at him and glared. It seemed to be more out of discomfort than him genuinely not wanting to hear what Castiel had to say but left Cas feeling nervous all the same. Maybe it was something in Cas’s face that suddenly made Dean drop his putout facade.

“I’m listening. I promise.”

“So, things were getting more heated and we were undressing each other and I knelt down to pull his pants down—“


“Dean you said you’d listen!” Castiel felt himself blushing. It was hard enough to be telling this to his roommate but it was even harder having to start and stop.

“I am! I am listening!”

“Please don’t interrupt anymore,” he pleaded before continuing… staring at a nondescript part of their floor to get the next part out. “As I was pulling his pants down, I guess my nerves got the best of me because I mentioned that I’d ‘never done this before’ and—and he made me stop.”

Cas’s heart was pounding in his chest reliving what’d happened. He’d been so nervous walking back to Arthur’s room. None of the shots he’d taken had calmed them either and he found himself shaking in his boots as he tried to pretend like he wasn’t a complete newbie to the whole sex scene. It was honestly probably the tequila that made him word vomit that he’d never done anything like that before… that he’d never done this before… that he was nervous that he wouldn’t be that good.

The look on Arthur’s face…

“Well that’s good,” Dean cut into his thoughts; “he didn’t want to push you to something you might not have been ready for.”

Castiel huffed in frustration. He wished that were the case. “No… I don’t believe that was his intent. His words were ‘what, are you a fucking virgin?’ and when I confirmed that I was… he uh—he told me to put my clothes back on.”

“What?” Dean asked, confused.

“And—and as I was getting dressed again he told me that I should have warned him because ‘people don’t want to fuck a virgin, they just get too clingy and too many feelings get involved’ but he did say he’d be interested sometime in the future if I got more experience.”

God, even just saying it out loud made the burning embarrassment come back full force. He’d been down on his fucking knees with another man’s dick in his hand. Fuck… he’d even been about to put it in his mouth and then he was rejected? Just because he said he’d never done it before? Was he really that undesirable that Arthur didn’t even want him to try? Didn’t guys like getting sucked even if it was only mediocre at best? God, even thinking back to the night Cas was now almost positive Arthur hadn’t even been fully hard.


It was honestly so mortifying. And now Dean had heard the story.

“I’ll tell you right now that’s not fucking happening.” Dean exclaimed, fuming. He looked ready to march over to the other man’s house and deck him in the face. “Asshole lost his shot with you!”

“No, no, I agree with you.” Castiel said softly. “I wouldn’t want to pursue a sexual relationship after his rejection anyway.”

“Good! You shouldn’t! You’re way too fucking good for that. What a fucking prick!” The anger in Dean’s voice settled something in Cas. The fact that Dean was so protective was definitely comforting.

Castiel’s mind went back to the first time Dean had ever brought out his protective side. They’d been at a party, as all of Cas’s embarrassing stories seem to start. It was just Dean and him that night at a random dorm room drinking whatever wine coolers the girls of the dorm had bought. There were quite a few people there and Castiel was chatting with a few girls over by the door. He had no clue where Dean was but figured he was off schmoozing some lady for the night when two of the biggest assholes came marching into the party. They were already drunk and started spurting obscenities at the girls in the room.

Cas had never been a confrontational person but the one thing Gabriel instilled in him was that you never turn a blind eye to a woman being treated poorly. Without hesitation, Castiel stepped in between the two men and asked them to leave. Words like ‘ugly’ and ‘fag’ were drunkenly slurred but Castiel wasn’t deterred from trying to push the men out towards the hallway. That’s when he felt the first blow to his cheekbone. The second came to his stomach.

Before he really knew what was happening there were girls screaming and furniture crashing. Castiel had just enough sense to pull himself upright to step out of the way of the flying fists. That’s when he noticed Dean punching one of the men square in the jaw. Castiel heard his friend nearly growling that he’d break the other man’s nose if he ever showed his face again. That’s when the asshole’s friend tried to pick a fight with Cas again, shoving him up against the wall by the throat. Dean was on him in two second flat. Some other guys at the party had finally gotten enough sense into them to help Dean drag the two assholes out of the dorm room. When Dean marched back into the room he pulled Cas out and back upstairs, sitting him on the edge of his bed as he took a washcloth to the cut on his face before forcefully pressing an ice pack to Cas’s forming bruise and nearly threatening him if he took it off.

It was knowing that Dean would do anything for him that had Cas gearing up to explain what he needed Dean’s help with.

“With what happened, it left me thinking.”

“About what?”

“Is it true?” He asked.

“Is what true?”

How was Cas going to explain this next part? He… he needed answers and he definitely needed help. He knew that he could trust Dean to be open-minded and honest with him. It still made him nervous to explain all the thoughts racing through his mind.

“I’ve never seen sexual purity to be of import. I know some religions or cultures believe it to be valuable, but to me the fact that I’ve not yet had sexual relations is more a reflection of my lack of exposure to others than my lack of desire to engage. But outside of religion and those cultures, is virginity looked at as something of a burden? Would others prefer their partner to be more experienced than not? I still was under the assumption that people enjoyed those who were considered ‘pure’?”

For a moment Dean looked at Castiel like he’d grown two heads. Clearly that wasn’t where he thought Cas was taking this conversation. “Oh… wow, uh? I don’t know?”

Castiel rolled his eyes at the non-answer. “You’re sexually active though—what are your thoughts on your partners having had other relations prior to yours?”

They didn’t really talk about sex. Actually, they almost never talked about it. For all the boisterousness and confidence Dean exhumed, he was still a gentleman when it came to his sexual experiences. Even when Castiel knew Dean was only seeking a woman for one night he never boasted about it, he never made the women he hooked up with seem like a conquest.

It took a while for Dean to gather his thoughts.

“Well, I guess I could see his point. Like if you’re looking for a night of fun and worry-free sex you don’t really want to do it with a virgin, because you don’t know how important their purity is to them, even if they say they don’t care but I think everyone’s opinion on it is different.” Cas nodded along as Dean spoke, absorbing every word.

“For me, too much experience is a little questionable, you know?” Dean continued, “I don’t want to be with a girl who sleeps with a new guy every night, not because I think she’s wrong to do that, but because you can’t be certain that she’s clean—and a one night hook up isn’t going to go get a test for you to be sure. But if I really like a chick, I’m not going to be driven away if they don’t have much experience and I want to see if our relationship could go somewhere.”

It made sense but left Cas with one burning question, “Do you prefer more experience in a partner?”

“I mean—yeah, it makes the sex more fun.”

Castiel nodded thoughtfully. “I think I understand now.”

He knew what he needed to do. There was no question that if he could gain more experience then he’d never have to go through something like last night again. The only problem was finding someone to help him gain the experience. There had to be someone trustworthy enough.

“So you’re cool now?” Dean asked.

“Not quite.”

“Uhm, okay?” The poor guy looked so confused. Why was Castiel making this so difficult? All he needed to do was ask Dean for help in finding someone.



“We’re friends right?”

“Yeah, dude, of course we are.”

“You’d consider us close too?”

“You’re joking right?”

Oh god his heart was going to fall out of his chest. Would Dean think this was the most ridiculous idea he’d ever heard?

“You know I wouldn’t ask something of you if I hadn’t thought about it before hand, right? That I wouldn’t willingly jeopardize our friendship?”

“Cas? What are you talking about?”

The more the words started coming out of his mouth the more Castiel realized he wasn’t entirely sure he liked his original plan. Yeah at first he didn’t see a problem with asking Dean to find him another person to help him with all things sexual but now… now he was starting to feel something akin to dread at all the people Dean might suggest. He’d probably suggest someone like Balthazar or maybe even just any stranger at a club and that wasn’t what Cas wanted.

The wheels in Cas’s mind started churning. What exactly did he want to ask Dean?

Maybe he’d already known all along.

He didn’t stop himself as his mouth seemed to speak for him. “This… this might be unusual, but I want you to keep an open mind, okay?”


“I want to gain more experience… sexually. I don’t want to fall into another situation like the one with Arthur.”

The face Dean made was a mixture of amusement and shock. “Dude, are you asking me to be your wingman? Because I’m totally up for that.”

I should. It’s what I should be asking you because that was my original plan, some part of Castiel thought. But that’s not at all what came out of his mouth.

“No… that’s not what I’m asking.”

“Really? Then what?”

Dear lord, he was probably going to throw up. This was a horrible idea.

“Dean, would you be willing to help me out?”

“I just said I would.”

“No… I’m sorry. I’m not making myself clear.” His voice was trembling as he tried to explain exactly what he hoped the other boy would be able to help him with.

“I don’t want to go through something like last night again. It was humiliating to be rejected like that and I never want to deal with it again. What I want is to have more sexual experience before I attempt to go out and meet other people. I want to know how to be confident and comfortable in the bedroom so that I don’t embarrass myself again. But I know the only way to gain experience is to learn with someone… and I thought… I thought that I could learn with someone I was comfortable with and whom I trusted.”

“What are you saying?” Dean’s voice was unusually devoid of emotion.

What was Castiel even doing? His intention was to get Dean to help him find someone, to sift through their friends until they found one that would be willing to help Castiel become a good lover. Why were the words coming out of his mouth the exact opposite of what he’d been planning to say?

He knew why.

He knew there wasn’t anyone he trusted more explicitly than Dean.

He had to at least try.

“Would you be willing to teach me how to perform sexual favors?”

Castiel watched as Dean swallowed hard. “Sexual favors?”

“Yes. Hand jobs and blow jobs seem the first logical task to learn.”

Dean was gaping like a fish. “What?”

What was he doing?

Did he not learn from last night to not put his foot in his mouth?

But Dean hadn’t punched him in the face or kicked him out…

Maybe if he just….

“Dean, I’d like to learn how to pleasure another person, and you’re the only person I’m comfortable asking for help with. Would I be able to practice on you until I’m ready to try with other partners?”

“You wanna have sex with me?”

“I’m not asking for intercourse at the moment. I’d just like to learn how to perform oral sex for right now.”

“You wanna blow me?”

Castiel flushed red hot because, lord, if that right there wasn’t a loaded question. But if he wanted to learn how to be a confident lover the first step had to be being brave right now with his answer. Right?



All this time he hadn’t been able to look Dean directly in the eye but now that he did, he saw a small amount of fear reflected back at him. His heart nearly plummeted into his stomach. Had he just ruined three years of friendship for this?

Not once did he think this would ruin their friendship.

But now?

Fuck, now it looked like Dean was searching for any and all excuses to book it out of the room.

Castiel could feel emotion starting to prickle at his eyes.

He was such an idiot.

“Dean, look. I understand this is an unusual request and that normal friendships don’t have one friend offering to perform sexual acts for the other. I’m also fully aware that you exclusively sleep with woman and that me being a man may deter you from this. I just… I don’t want you to make a decision right now, Okay?”

Dean didn’t so much as blink. Fuck, Cas might actually cry. He just had to say his peace.

“All I’m asking is that you take it into consideration. If you decide you’re willing to help me, I promise no one will know. I would never betray your trust and tell another person about it. I also don’t expect anything of you, this would all be me learning how to give others pleasure so you wouldn’t be required to touch me, or even look at me if you didn’t desire… I just ask that you’d be willing to verbally guide me through it all.”

Castiel waited for a beat, waiting to see if Dean would even nod at him but nothing came. He stood up and moved from the makeshift ‘living room’ and started packing a bag. Even five minutes later Dean still hadn’t moved an inch. Castiel stood near their doorway, fighting back the first sob he knew was coming in order to say goodbye.

“I know I’ve officially made you uncomfortable so I’m going to leave you for the rest of the night. I’ll stay with Hannah until tomorrow.”

Again Dean said nothing so Castiel just let the door click shut behind him.

This rejection hurt worse than Arthur’s.

Chapter Text

He felt like an asshole.

Something ugly churned inside of him every time he pictured the look of utter rejection on his best friend’s face.

Why hadn’t he just said something? Anything!

But really, what could he say?

There wasn’t exactly a guide book for what you’re supposed to do when your best friend practically tells you they want to blow you for science.

It was weird, all right?

But what was weirder was that the more Dean thought about it, the less weird it had become in his mind.

Yeah, the fact that his best friend wanted to learn how to give good head and had asked him to help was a little weird… but he could see Cas’s logic in it. They were best friends. He trusted Cas with his life and was fairly certain Cas felt the same way in return. It seemed logical enough to want to try and ease your way into the finer parts of sexy times when you had someone you were comfortable with to guide you through. It probably wasn’t the best idea to hook up with a friend though… a significant other would be easier to ease into it all with. But it still didn’t diminish Cas’s logic.

At the time Cas had asked, it’d just been too overwhelming. Dean had no clue what he was supposed to do or say while listening to his best friend practically promise him unlimited blowjobs. He’d been in shock. But now he was left feeling like an asshole because there was no way he didn’t hurt Cas from his stone-faced look.

Still he’d needed to sleep on it.

In his defense, he did extend some sort of olive branch Monday morning when he texted Cas to come home that night. The gesture made him nervous as all hell but he couldn’t let Cas stew in his own worries for another night.

It crushed him a little seeing Cas’s sad response that he’d understand if Dean didn’t actually want him to come back and could stay away a little longer. But Dean wasn’t going to let that happen.

Did Cas really think Dean would throw away their friendship over something like this?

No, he and Cas were solid. Cas had even been one of the first people in Dean’s life he ever felt comfortable dishing out the details of his past. Not once did Cas judge him or show any form of pity for the shit Dean had gone through, he just accepted the facts and went on with life. It was the first time Dean realized that the dorky guy with the perpetually messy hair was without a doubt his best friend. They’d been through a lot together since. So, no, something like this wasn’t going to ruin their friendship. Dean would make sure of it. It might be a little awkward for a few days after they had this talk but they’d be okay.

Dean knew what he had to do when Castiel came home. He had to tell Cas that it wouldn’t work out. They were too good of friends, and Cas deserved to find someone he cared about to experience all those things with.

He knew his best friend’s counterarguments would probably be solid but Dean needed to stand his ground. If he did say yes, their friendship would be undeniably altered. Maybe they could work with it and still keep their friendship the way it always had been just with a few side moments for ‘experimenting’ but Dean wasn’t an idiot. Friends don’t remain friends when one of them has had the other’s dick in their mouth.

He had to say no to Cas’s idea. He’d just be the best damn wingman Cas could ask for instead.


He cringed a little. He didn’t exactly love the idea of being Cas’s wingman in order for his best friend to find someone else he could experiment with. What if Dean wasn’t a perfect judge of character and found someone like Arthur for Cas to hook up with? He’d never forgive himself. He cared about the guy, and despite hearing how Cas seemed so indifferent to having sex for the first time he didn’t want Cas to just try out this new sexual side of himself with just anyone. He wanted Cas to have the right person.

There was really no one off the top of his head that Dean would trust to guide Castiel through his sexual experimentations; no one he could think of would be able to withhold judgment for Cas’s inexperience and over eagerness to learn. And in the end, really there was not one single person he could think of who would truly respect Cas after it were all over.

No one besides himself.


Maybe he was torn.

Perhaps there was some small part of him who wanted to be able to show his best friend how to be a more confident lover. It wasn’t merely anything more than him being protective of Cas and not wanting him to get hurt… paired with the fact that Dean knew he was pretty good in bed himself. He did have some knowledge he could pass to his friend and they did know each other well...


No. It couldn’t work. That Arthur dude had a point… sometimes feelings happen with virgins (or sex in general) and that’s not what Cas needed to happen with Dean.

It almost frightened him how little the fact that Castiel being a male wasn’t actually frightening him. Not once had Dean ever been with another man. He identified as a straight man but he wasn’t exactly unattracted to men. He had no qualms with silently checking out another man at a club or even on TV or the Internet. It was hard not to, especially when it came to porn. He could definitely appreciate some muscles and a nice cock here and there but he was most definitely attracted to women.

But the idea of a man… of his best friend, Castiel, giving him head?

It was an intriguing idea.


It was a bad idea.

Maybe a potentially pleasurable one… but definitely a bad idea.

God damnit, he needed to stop thinking about getting sucked.

But fuck that sounded really nice about now.

Not from Castiel though.


No. That’d be weird.

From a chick.

Like Lisa.

She gave good head.

Well average head. Nothing really could top Rhonda Hurley but that’s probably what happens when you’re nineteen getting sucked off by a twenty-five-year-old. Sets the bar pretty damn high. (It probably wasn’t even that good but he’d gotten maybe a handful of half-hearted blowies before that so everything in comparison was garbage compared to her experienced mouth).

Fuck. Now he was getting hard.

Sitting on the small futon they had in the living room section of their dorm, Dean looked at the clock on his phone and took note that Cas’s class wouldn’t be out for another hour and a half, which meant he had more than enough time for some alone time. It was rare that he had the dorm to himself and each time he did he knew he had to use the time to the best of his ability.

And now with the memories of his dick springing up through the waistband of the silky panties Rhonda had talked him into, as she mouthed at him through the fabric.


He needed to get off now.

He pulled his laptop over from the ottoman and quickly typed in the name of his favorite porn sight. Dean wasn’t too picky with his preferences on what he watched, he didn’t care about what ethnicity the woman he watched were, or if it was just two girls, a girl and a dude, or two dudes and a chick. As long as the video quality wasn’t terrible and the ‘acting’ wasn’t cringe-worthy he always found himself able to get off.

Right now, he didn’t have anything particular in mind so long as there was a cock getting sucked. He scrolled through the top watched of the week and found one that drew his attention enough. It was of a brunette, on her knees and the time in the corner looked like it was long enough to work him up to completion.

Shit. This was going to be embarrassingly quick.

Out of habit, he put his headphones into the port on his laptop, never feeling comfortable listening to the sounds of others having sex through his computer speakers even if he was alone. Dean propped the laptop up on a couple pillows that Cas had bought for the place, and slid down his basketball shorts and boxers, getting into a more comfortable position before pressing play.

He’d never actually been ass naked on the couch before… always wanting to respect Cas’s space too…. but desperate times.

Not big on drawing things out when alone, he let out a pleased sound when his hand wrapped around the base of his still hardening dick. For a moment he found himself wondering how long it had actually been since he’d fucked his fist. Fuck, how long had it been since he’d had sex? Like three or four months? What the fuck has he been doing?

He was pent up and desperate. With eyes on the screen he worked on massaging himself for a while, watching the woman in the video. She was definitely an eager cocksucker, sloppily bobbing her head onto the man’s dick and fisting her hand around the base. The no-faced man had a hand wrapped in her hair, pumping into her face at a steady pace, moaning and grunting with every thrust.

Shit. He needed that right now. He needed the feeling of a wet mouth to pump into. Spit dripping down his length. The wet sounds of his cock hitting the back of their throat. The sight of full lips stretched wide around him.

Not having any lube or lotion around Dean pulled his hand away from his dick to spit onto a few times before turning his attention back to his aching member.

The sloppy editing of the video now had the man in the video licking the woman’s wet hole as he thrust one finger into her, hardly going in past the second knuckle. Even the woman’s sounds were pathetic. Slowly Dean felt his interest drifting away from the events in the video, focusing enough on the woman’s bouncing boobs to hopefully get himself off quickly.

Drifting his eyes away from the screen because let’s be real nothing is worse than watching people have unenthusiastic, bad sex, Dean nearly had a heart attack. It was then that he noticed a figure drop down in front of him.

Launching into fight or flight, Dean ripped his hand from his dick and slammed the laptop closed before he realized he’d left himself completely exposed. He tried to haphazardly cover himself with his hands but it wasn’t like he could do much with himself at full mast.

How the fuck did he not hear Cas come in?

Fuck! The fucking headphones.

He pulled them out with one hand and just stared at Castiel, mouth agape. His heart was pounding from the shock. Every ounce of him wanted to scream ‘what the fuck’ but there was something in Cas’s body language that stopped him.

Cas was on his knees on the floor in front of the futon, staring down at Dean as his chest heaved heavy sighs. Cas’s hands hovered just above Dean’s thighs like he’d only just aborted the movement to actually touch Dean. His pupils were blown and his lips were parted and he was looking at Dean like he was a fucking Thanksgiving feast.

At the same time Dean dumbly said, “Cas—“ his best friend asked, “Dean… let me?”


Dean watched as Castiel fought the urge to touch him. He watched as his best friend’s hand twitched in mind air so close to its desired destination. Cas’s eyes didn’t wander though, his eyes stayed locked on Dean’s the whole time.

“I want to. Please, let me.”

Dean didn’t know what to say. He was in the in between state of deflating because of the fact that his very male roommate had just caught him jacking off, but the way Cas was staring at him was somehow keeping his dick in the game. His stomach muscles trembled as his body fought to be touched… to have hands on him. Castiel seemed to be able to read his mind or at least his body.

“I’m not touching you until you say yes. I’m not going to do anything you don’t explicitly consent to. You say no and I’ll never ask again. But I want this. I trust you.”

Dean didn’t know what possessed him to say yes. But the moment the word left his lips, he didn’t care, as a large hand wrapped around him and stroked him back to full hardness. Dean’s head flew back, hitting the back of the couch with a sigh.

Holy fuck.

His body didn’t seem to care that the hand around him did not belong to a woman—no, it only seemed to care that he was being touched. He canted his hips up ever so slightly in approval, feeling as Cas gripped him a little more confidently though lacking finesse. Mini Dean seemed to enjoy the company of another hand because sooner than ever, Dean felt his muscles begin to tingle and tighten all the way down to his toes… it just wasn’t quite enough to push him over. Not yet.

Needing more, he blindly reached to wrap his hand around Cas’s, guiding his roommate’s motions, showing him the twists and the pulls that would finish Dean the quickest.

“Oh. Fuck!” He grunted, only mere seconds before catapulting over the edge.

And then he was silently screaming with his mouth open, feeling the ropes of cum spurting out from him, covering both of their hands. His toes fucking cramped with how hard they curled…

“Oh god.”

He kept their hands moving for a moment later, wringing out the last of the spasms before he couldn’t take the touch anymore. He dropped his hand by his side as his head lulled against the back of the couch, trying to catch his breath.

One… two… three breaths and the reality of what just happened hit him square in the gut.

What had he just done?

He refused to open his eyes. He couldn’t look at Castiel right now. He couldn’t…. what the fuck did he do?

This was exactly what he wasn’t supposed to do.

He waited for Cas to say something but nothing ever came. Eventually he heard the sink from their on-suite bathroom turn on.

Dean only opened his eyes when he felt his groin being tenderly wiped down like it was a completely normal thing for his friend to just be wiping down his dick.

“I can—“

“It’s okay.” Castiel didn’t take much longer in finishing. After he wiped the last of Dean’s come away, he leaned down just enough to start tugging Dean’s shorts back up. There was something so weird about feeling his best friend tuck his flaccid dick back into his shorts that Dean couldn’t even find words to protest.

Then there was silence. Neither he nor Cas knew what to say to one another.

Castiel was now sitting on their ottoman across from Dean, steadfastly keeping their limbs from touching.

Dean could feel his heartbeat pounding in his ears. There was no way even Castiel and his frequent lack of social cues couldn’t pick up on the awkward tension growing thick within the room. What could Dean even say? Except to apologize a hundred times over for allowing something like this to happen… fuck. He couldn’t believe he’d let himself say yes.

What the fuck was he thinking?

“You’re uncomfortable.” Cas finally said into the void between them.

Dean’s first instinct was to say ‘duh’ but he knew he’d be lying. Or half-lying. He was only uncomfortable with the fact that he’d put Cas into this situation not the fact that his best friend had just jerked him off.

“I’m not uncomfortable.”

Castiel didn’t seem to hear Dean because his rambles overlapped. “I know I just overstepped. I shouldn’t have done that. I’m so sorry if you feel like I took advantage of you. I’m so sorry Dean. I’ll understand if you can’t forgive me.”

The genuine worry in Cas’s voice gripped at something in his chest. “What? You think you took advantage of me?”

“You didn’t want that. I shouldn’t have pressured you.”

He had to stare at the blue-eyed boy across from him for a moment to let what Cas said sink in. Cas’s eyes were wide with worry in a way Dean hadn’t seen since the other boy thought he’d failed his first final freshman year. Of course, they were both worrying about the same thing right now. Dean thinking he’d just used Cas for his own pleasure and Cas thinking he’d just taken something from Dean that wasn’t given explicitly.

Dean hated that look, and he was determined to make sure to fix it right away. “I didn’t want that? Cas I knew what I was saying yes to and if you missed it, I kind of just came harder than I have in a really fucking long time. I wasn’t pressured into anything. I’m not upset with you. I’m upset with me. I shouldn’t have said yes because what the hell does this mean now? This changes things.”

He should have thought that last part over before speaking because now Cas’s eyes were wild with fear.


“You’ve had my dick in your hand. That’s not exactly what friends do!”

“But it’s what I want us to do.” Cas rushed to say, looking desperate for Dean to understand. “There is no one I trust more than you and I know this could work. I just want to be experienced… even just now you had to assist me because I wasn’t doing it right and I want to learn, Dean. I want to learn how to bring you or another man to orgasm without assistance. I want to be good at this.”

Dean could feel his resolve slipping between his fingers. He knew somewhere deep down that this was probably the worst idea but… they’d already done this one thing. What could a few more tries change? If Cas wanted to learn he wouldn’t mind helping but… that didn’t mean he wasn’t going to at least try and show reason to his best friend. The guy had to understand that there were other ways to go about this. This wasn’t Cas’s only option.

“It just takes time, Cas. It takes a lot of awkward fumbling and weirdness before you get it right.”

“But I don’t want to deal with that!” Cas groaned petulantly. “I want to get through all the awkward parts with someone now. I want you to help me. Will you please help me?”

He let the silence grow between them as he contemplated his answer. He knew their friendship was strong enough that if he took the sensible approach and turned Cas down, they’d be okay. Of course, they’d both know that something had happened between them but they’d figure it out. He just…. He couldn’t get the idea out of his head that if he told Cas no that his best friend would try and find someone far less suitable to help him than Dean. He was terrified that the other guy would end up hurt in a way that Dean could have prevented if he just helped him.

And that fear, the fear of doing wrong by Castiel had him asking…

“How would this even work?”

Even Cas seemed stunned by Dean’s seeming acceptance of the arrangement.

“Really? You’ll do it?”

He felt like there was a lump in his throat but he swallowed around it. “I’m considering it. Just walk me through it.”

“Well… I hadn’t really… I’m not really sure…” Castiel floundered for words like he hadn’t once expected to hear a yes from Dean. Dean still wasn’t convinced this was a good idea but if he was going to do this he needed to know all the details.

“How would the uh… learning… happen? Or start?”

He felt stupid not being able to say ‘Hey Cas, how will I know when you want to blow me?’ but Cas didn’t seem pulsed by his word choice.

“Uh… well, how about when either one of us feel like… learning, we can ask the other person? If we’re both in agreement we… we uh… practice. But if one of us isn’t feeling up to it, we drop it? We just have to communicate.”

Dean nodded along dumbly to what Cas was saying. It sounded reasonable. He just needed to know more… “What all do you want to learn?”

He could see the possibilities roll through Cas’s mind and Dean had to admit that it made him very nervous. He wasn’t sure how far he’d be willing to go for this. He’d never entertained the idea of doing anything sexual with a dude but hand jobs and blowjobs seemed innocent enough. Dudes in college experimented with those things sometimes, right? Just to see if they even liked it?

But would he be okay with doing more? He didn’t think he could like… return the favor or something. He didn’t think that’d be something he’d want to do… toeing a little too close to something he wasn’t quite certain on. But maybe that wasn’t on Cas’s radar currently?

Castiel must have picked up on his hesitance because he looked Dean sternly in the eyes. “Anything that you’re willing to teach me. So long as you’re comfortable with it.”

Oh shit. He was really doing this.

“Should we have rules?”

Tension seemed to finally drain out of Cas’s shoulders and it took a moment for Dean to understand how much this actually seemed to mean to Cas. Dean had been so blindsided by the idea that he didn’t take a real moment to think of this from Cas’s point of view. Dean had been fifteen when he’d lost his virginity to Cassie Robinson, equally a nervous virgin on their sophomore Homecoming night. He never really thought of what it would feel like to try and put yourself out there at twenty-one, only to be turned down for not having experience. But Cas’s pure relief at Dean’s acceptance of the arrangement had him realizing for the first time just how vulnerable Cas had probably felt. How the rejection the other night had made him try and seek out a solution to the problem.

Some part of him was terrified he’d fucked everything up between them by saying yes, but on the other hand, seeing Cas perk up like he’d been given a gift made Dean bite his tongue.

“Of course, we can establish rules, if that makes you more comfortable.”

Dean put on his best winning smile. “It’s probably best. Where do you think we should start?”

“How about basic ones for now and we can come up with others as we go?”

“What do you have in mind?”

“I think…” Cas trailed off, contemplating. “I think it would be best if we don’t tell anyone about this for starters. I don’t want anyone assuming things they have no clue about.”

Dean tried not to make his sigh of relief obvious. He didn’t think he could handle anyone around them finding out that they were “learning” things together in their spare time. “I think that would be best too.”

“And… I feel we need to check in with each other regularly to decide where our comfort levels are. If either one of us wants to stop this at any time we stop, no questions asked.”

“That’s good.” He was thankful Cas seemed very keen to keep Dean comfortable and not ask for more than he was willing to give.

Cas fiddled with his pant leg as he worked up the courage to reveal his next rule. “And… no sleeping with anyone else?”

“That’s fair.” Dean responded without hesitation, making Cas’s head whip up.


Dean had to fight the instinct to take the shock in Cas’s voice personally. Of course, he wouldn’t go around sleeping with other people if he and Cas had this arrangement going on. He might not be a saint but he’d never been one to sleep with multiple people at a time. Plus, he’d never put Cas at any sort of risk of contracting something, no matter how much protection Dean always used with other partners.

“Really. Until we decide you’ve learned enough. It’s not a big deal to me.”

Cas’s smile was genuinely grateful. “Thank you.”

“So we’re doing this?” Dean asked through a nervous smile of his own.

“As long as you’re sure.”

He knew he wasn’t sure if this was the right choice but in making this choice he was sure of two things.

1. Castiel Milton was his best friend and he’d do anything for him.

2. He didn’t want anyone else helping Cas with this.

“Free blow jobs whenever I want? I’m sure.”

Chapter Text

From the moment their agreement was sealed everything seemed to snap back to normal.

Even after their talk and Dean explicitly agreeing to helping him out, Cas had been doubtful. He knew Dean better than he knew anyone and that meant he felt pretty confident in predicting his friend’s reactions but Dean just wasn’t reacting the way Cas had anticipated. He’d expected anxiety to roll off his friend in waves and for Dean to clam up in his worries and stop talking to Cas because he’d realized that he regretted letting Cas give him the hand job.

None of that was happening though and Cas didn’t know what to think.

He wasn’t going to ruin the normalcy by mentioning anything. Instead, he was going to roll with it and allow himself to be excited that Dean had agreed to help him. They had rules and mutual understanding between them and Cas was filled with nervous excitement.

He had to resist asking Dean if they could start ‘learning’ (as they’d been calling it), that very night, thinking it might be too soon to bring it up but it was definitely, definitely on his mind. Instead, he just took Dean’s cues, and readily accepted when his friend asked if they could just play some video games together and order pizza. It was all so normal.

Now, knowing that he could think about it, the possibilities of what he could learn were on Cas’s mind all day every day. It’d been a few days since Dean had agreed to help him but for some reason every time he thought about asking Dean if they could proceed with their arrangement his nerves got the best of him. He knew he was going to be bad at it but he didn’t want to be so bad that Dean would think of this as a chore. But Dean had promised to teach him, right? Logically, if Castiel were bad at it, he had to at least trust that Dean would guide him into doing things the correct way. Right?

The normalcy lasted only a few more days before Cas couldn’t fight off the anticipation anymore. He figured a Thursday night would be best anyway since they didn’t have classes on Friday and it’d give them the whole night. Not that he thought it’d take the whole night… but if it did, they at least had more time… Yes, he was quite nervous.

He didn’t think this part through when he’d first thought of doing this with Dean. He hadn’t looked past actually having Dean agree so now, thinking about how to even approach the subject again made him feel like his heart was going to beat out of his chest. He knew that Dean had already agreed but per their rules, either of them could say no to doing something if they weren’t up for it… what if Dean said no?

His mind was a flurry of ‘what if’ scenarios as they watched a movie together, Dean on the navy-blue futon, and Cas on the fast food stained brown beanbag. He didn’t think Dean could tell that he kept glancing over every few minutes trying to gauge Dean’s state of mind.

Would he be interested?

Was he in the right mood?

Should Cas leave so that Dean could watch some porn or something to get in the right mood?

Should he just wait until tomorrow night?

The questions were gnawing at Cas to the point he thought he was going to explode. He just needed to be brave. Dean had agreed to this, hadn’t he?

All Cas had to do was ask.

Before he could second-guess himself any more, he felt his vocal cords release a hoarse, “Dean?”

His friend didn’t bother looking away from the screen. “Yeah?”

“Can we uh—” Cas’s voice shook with each syllable, causing Dean to turn away from the movie to catch his eye. “Can we… you know?”

There was an audible gulp as Dean straightened up in his seat. He seemed unsure of his own voice too. “You want to?”

Cas felt himself faintly nodding. “I want to learn.”

It seemed to take a minute for Dean to wrap his mind around what Cas was asking but before Cas could stress too much about rejection, Dean was nodding in return. “Oh—okay. Okay, yeah.”

“Do you want… do you want the same as before?”

“The same? You mean….” Dean watched him as Castiel pulled himself from his spot on the beanbag and moved to sit in front of Dean on the ottoman. His roommate seemed almost as nervous as Castiel felt. “Like… the last time we…. Uh, uh yeah? Or whatever you want to do…”

Cas bit his lip and slid off the table to kneel in front of Dean. Butterflies were on a rampage in his gut. He fought through it though, willing himself to just ask for what he wanted. “I think… I think I’d like to uh—I think I’d like to use my mouth too.”

Dean’s mouth dropped open for a split second like he was going to say something. He shook his head before saying, “Right. Right, yeah. Yeah, that’s fine.”

Last time it’d been… easier, per say. Last time Cas had walked in and seen his best friend bare from the waist down and had just kind of—reacted. Dean had already been aroused, had already been close to orgasm and so it wasn’t exactly all Castiel’s doing that his friend had gotten off. But now… now he needed to get them from point A to point Z and he didn’t know where to begin.

He tried not to let himself feel like an idiot.

“What should I do?”

He wasn’t sure if Dean didn’t understand the question or if he was as nervous as Cas because it took the other man a while to answer.

“Oh, I’ll just uh—I’ll just take my pants off I gue—“

“May I?” Cas cut in rather abruptly.


“May I undress you?”

Cas had never seen Dean’s eyes quite so alert, perhaps alarmed, but still his friend was nodding in agreement.

“Yeah, okay. Okay, yeah.”

Cas dropped to his heels, and nudged Dean’s knees apart, but was careful not to invade too much of the other man’s space—as ironic as that seemed. His hands were a little shaky as he tentatively reached forward going straight for the ties of Dean’s sweats.


Cas’s hands flew back to his side like he’d been shocked. “I’m sorry.”

He couldn’t look up. He’d completely understand if Dean had changed his mind but Cas kept his eyes turned down towards the carpet under Dean’s feet not wanting to see the look of rejection on his friend’s face.

But Dean dissuaded his fears immediately. “No… No. Don’t be sorry! I just—I just…. You want to learn and I’m not doing much teaching.”

“What do you mean?”

Castiel noticed that Dean was fumbling with his words as much as he was, which helped to calm him down moderately. “You don’t have to do this, but uh—when you… when you want to make your partner like, really excited, you gotta… you gotta drag it out.”

“What do you mean?”

“Unless you’re both like desperate to get to the good stuff, a lot of the time the best part is the buildup.”

“Okay.” Cas stated, soaking up the advice even though he couldn’t say he fully understood how prolonging the ‘build up’ could be considered the best part. Wasn’t the best part climax? He listened to Dean’s advice nonetheless.

“It’s all about getting things heated. Just now we were watching Hunger Games and like—that isn’t the most sexy setup.”

“Oh—I’m sorry.”

“No, no, no!” Dean stopped Cas’s negative train of thought before it started. The green-eyed man seemed almost confident now. “I’m not trying to make you feel sorry, just, if the goal is to go from 0 to 60, you can start ripping clothes off and just get on with it. But if you want it to be more memorable and seductive, you gotta ease into that.”

“How… how would I do that?”

“Uhm, touch. Touch is a good thing. Like slow hands and stuff… Playing with the button or zipper or whatever to tease them a little bit…. You know, stuff like that.”

Cas was still shaking a little nervously as he leaned off his heels. This was the type of direction he needed to hear to know where to begin. Slowly, he placed his hands on Dean’s knees and almost feather-light, slid them up his thighs stopping well before he got anywhere near the waist band of Dean’s sweats.

“Like this?”

“Yeah, that’s a good start.” Dean encouraged. He’d shifted down the seat a little more to spread his legs wider, letting Cas between them more easily. “But I feel like I have to tell you again that you don’t have to do what I’m saying right now, it’s all just for future reference.”

“I might as well practice.”

“Yeah, yeah, okay,” Dean agreed quietly.

Cas looked down at the man in front of him. Of course, he knew Dean Winchester was attractive but even in his holey, grey sweatpants and a stained ACDC shirt, he still managed to look incredible. It was no doubt the sharp lines of his jaw, peppered with light scruff, paired with the natural muscular build that filled out his shirt, and those bright green eyes that currently shone with nervous but undeniable trust… that all had Cas feeling braver suddenly.

“Should I keep going?”

“Yeah. Just do what you think feels natural I guess? I’ll tell you if it’s weird.”

Cas took that as a sign to get things moving along. He restarted the movement of his hands, now trailing up Dean’s thighs heading towards the waistband again. Right before he made contact, he hesitated. He didn’t know where he should go from there. To continue running his hands over the muscles hidden beneath Dean’s clothes or jump to the removal of said clothes?

Just when Dean was about to say something, Cas’s mind was made up.

His right hand began its ascent, trailing up, up over Dean’s t-shirt clad stomach and over his sternum until it reached his neck and trailed back down. He tried to take Dean’s advice and do what felt natural, so Cas let his left hand trail back down his best friend’s thigh, his thumb moving to brush against the inner part of Dean’s upper leg. Dean’s legs instinctively parted further; encouraging Cas to bring his palm closer to where he hoped Dean was building in his pants.

“That’s good.” Dean whispered in encouragement.

“It is?”

“Yeah. Definitely.”

Emboldened, Castiel kept with the touches for a while longer before drawing the courage to undo the ties of Dean’s sweat pants. It was then that Dean lifted his hips, allowing Castiel to slip his fingers under the band of Dean’s sweats and boxers and slide them down.

Warmth filled him as he watched Dean’s hardness spring free and land on his stomach with a soft bounce. Castiel didn’t know how to describe the relief he felt having visual evidence that Dean was at least aroused. Only then had he realized just how nervous he’d been that Dean wouldn’t be able to get it up…

He pushed those thoughts aside as he released each of Dean’s legs from the confines of his clothes before settling more securely into the space between his knees, and gazing down at Dean’s enticing length. Castiel had nothing besides himself to compare it to but he knew that Dean was perhaps average in length, but slightly above average in girth. It was without a doubt a very appealing sight.

“Maybe don’t stare at it like it’s a science project.”

Cas’s head whipped up and his cheeks heated profusely. “Sorry, sorry! It’s just last time I didn’t really look at it and I thought that—“

“Hey, it’s okay.” Dean said with a shy smirk. “But it makes a guy a little insecure when someone just stares at it…”

Castiel looked back down, appreciating. “You shouldn’t be insecure, you’re definitely well endowed, larger than myself actually.”

“Geeze Cas, okay…” He watched as Dean dragged his hand over his face. The tips of his ears were suddenly red.

Damnit, Cas was already screwing this up!

“I’m making you uncomfortable.”

“Honestly? Not really. It’s little strange, but all new encounters tend to be at first.”

The look in his eyes made Cas know he was being honest but Cas didn’t want to ruin the moment by talking anymore and maybe saying the wrong thing. Instead, with more skin to touch, he let his hands roam up and down Dean’s lightly hairy thighs and up over his trembling stomach. Now that he was allowed to touch, he felt like he couldn’t do it enough; he wanted to put his hands on every surface of Dean’s body but that wasn’t what he was here for.

He attempted ‘teasing’ only for a few moments longer, moving up and down Dean’s torso, grazing his wrist or knuckles over the head of Dean’s dick with each pass (more on accident than anything) but Cas learned that he already loved the small inhales that were crossing Dean’s lips with each pass.

Needing to know if he could pull any more sounds out of Dean and not having much more patience, Cas finally slid his hand up and over Dean’s hardened cock and gripped him firmly. He stroked him as he had last time before Dean croaked out, “Lick your palm.”

“What?” Cas asked, pulled from his slight trance of knowing he got to do this to Dean.

Dean tugged at Cas’s hand, making his words finally register in Cas’s mind.

“Lick your hand or spit...”

Castiel did as asked and soon was gifted a total body sigh on Dean’s part when his slicked hand wrapped back around. He moved his hand the way Dean showed him, making sure to twist at the top just the way Dean said he liked best. It wasn’t long before he was able to see the way Dean was reacting to his ministrations—Dean sank lower on the couch with every arch in his back.

Dean wasn’t touching him, not that Cas was surprised but out of curiosity he looked up to his friend, wanting to know what he looked like. One of Dean’s hands had found its way to his hair, while the other gripped the couch cushion by his head; his eyes were scrunched closed, his mouth open, and he looked completely blissful. Cas looked back down at the cock moving in and out of his closed fist, feeling inequitable want course through him as he noticed the precome dripping from the tip.

He felt emboldened at the moment and didn’t hesitate to lean his head down just to get a taste of Dean. He licked softly at the head, and heard a resounding moan escape from above him.

“Was that okay?” Cas asked quickly, needing to know if he’d crossed a line or not.

“Yeah.” Dean said through a breath, before finding his voice. “Yeah… yeah that was good. You can do that again. Only—only if you want to.”

So Cas did. One, two, three small licks and then he was certain he wanted to take it a step further. Moving his mouth to the base of Dean’s shaft, Castiel flattened his tongue and dragged it all the way to the top savoring the taste of Dean; faintly salty but a twang of soap? He didn’t think past the flavor when he felt Dean suddenly shiver.

“That’s good. Yeah, that’s really good.”

Cas preened under the praise, allowing the words to flood him with bravery. After pumping his wrist in a few more strokes, Castiel finally open his mouth to let Dean in. It was… intimidating to know that he had his lips around Dean’s cock. That he was giving his best friend a blowjob—the first he’d ever given. And… he liked the fact that he was doing it. Dean filled up his mouth far more than he’d anticipated but the weight of him in Cas’s mouth made his own body flood with heat.

He obviously knew no practical skills in this regard but had watched enough porn to know than licking, sucking, and bobbing were all techniques that seemed to be highly encouraged in giving head. So, Castiel went with his best instinct, licking around the girth in his mouth as he moved his head shallowly up and down—his hand still moving in tandem at the base of Dean’s shaft.

“Ah! Yeah! Like that…” Dean gasped, his hand now finding the side of Cas’s head, trying to urge Cas off. Cas pulled off for a moment, glancing up at him behind his lashes as Dean panted out more directions. “Don’t try… don’t try and take it all. Just do what you can,”

With a small nod, Cas went back to it, a shiver running through him as Dean breathed, “Yeah… yeah… that’s good.”

Soon, Dean’s instructions started coming out in staggered breaths, telling Cas when to speed up or slow down. Castiel knew he wasn’t going to be able to take Dean’s length down his throat just yet but he did what Dean told him to do with his hand still working the shaft, to make sure that it was still pleasing.

His knees were starting to ache from the carpet pushing against them and his jaw was definitely becoming sore from this new use for it but Cas’s own cock was throbbing from a burning desire to touch himself. The sounds and moans Dean was making just from Cas’s hand and mouth were more of a turn on than Castiel ever expected. It maybe should have scared him how much Dean’s arousal affected him, but he didn’t care. He loved that he was able to get this kind of reaction.

He was the one who was drawing these noises out of Dean.

Suddenly his hair was being gripped tight and before he could even grunt protest, his mouth popped off Dean’s cock with an obscene smack and Dean’s release was being ejected onto his hand.

Castiel stared wide-eyed at the blissed-out look on Dean’s face before hoarsely asking, “Was that okay?”

“Are you serious?” Dean asked with a breathy laugh but Cas wasn’t entirely convinced it was okay. Dean must’ve seen Cas’s trepidation face because soon after he said, “Yeah, Cas, it was better than okay.”

That felt good to hear, amazing really. He smiled to himself a little, hoping he didn’t look too ridiculous grinning about giving a mediocre blowjob. He was still reeling a little from the fact that he’d gotten to do that when Dean lethargically patted the space on the couch next to him and said, “Come up here, your knees and neck are probably killing you.”

Cas followed the command, but found himself uncertain of what he should do. Currently Castiel himself was hard in his pajamas, with a some come on his hands, as his best friend sat bare from the waist down calming down from his orgasm. Did he go clean them up? Did he need to help Dean into his clothes again? Should he just go shower and get himself off?

He didn’t know if he should ask.

“You need to get off?” Dean broke into his thoughts. He looked over at Cas with a hint of shyness. “You can—uh, you could like lean against me as you do it… or whatever. I don’t mind.”

“No… no.” Cas insisted, not wanting to impose his own needs on the other man. The deal was that Castiel would learn to pleasure Dean so Dean didn’t own him anything in return and Cas wanted to stick to that. He didn’t want to needlessly make his best friend uncomfortable. “I’ll just go take care of it in the shower.”

Dean seemed, perhaps, hesitant to let him go. “Okay. If you’re sure.”

“I am.” Castiel confirmed, before turning a bit more bashful. “Uh… Thank you. For that.”

“I should be thanking you, dude.”

“You’re the one teaching me though.” Castiel insisted but Dean didn’t seem impressed. His friend had a look of discontent on his face suddenly, making Cas nervous.

“You don’t need to thank me, okay? Not for any of this.”


Dean offered him a kind, but sad smile. “Go shower, okay?”

Following Dean’s orders, Castiel went off into the shower. He took care of his still-proud erection before quickly cleaning himself up and slipping back into his pajamas. He couldn’t quite pinpoint the feelings he had coursing through him.

He’d actually done it. He’d given his first blowjob and it was successful. He felt good about it afterwards too, a sense of relief even, it was almost some sort of accomplishment knowing that there wasn’t anything so wrong with him that someone wouldn’t enjoy feeling his mouth on them. He knew it was probably nowhere near the top of Dean’s list of preferable blowjobs but his friend had seemed satisfied enough. The look on Dean’s face afterwards was what left Castiel unable to feel completely content with the events of the night. There seemed to be something plaguing Dean’s mind and that unsettled Cas greatly.

Did Dean not want to go further than just one night?

By the time he came back into the room, Dean was cleaned up and dressed again. The other man smiled at Cas from across the room. “Wanna finish the movie?”

“Yeah. Sounds good.” Cas responded, walking across the small space towards his beanbag feeling relived that Dean didn’t look so disturbed anymore.

Before he could even move to sit, Dean’s hand softly connected with his lower arm, forcing Cas to stop his movements. “Come over here.” Dean commanded gently.

Cas followed Dean’s wishes but that didn’t stop him from questioning them. “Why?”

“I’m making a rule.”

“What rule?”

There was a hint of trepidation in Dean’s words, but his eyes showed sincerity. “We… we uh…. We cuddle after.”


“I’ll shoot you if you ever tell anyone I like to cuddle,” Dean growled jokingly but followed, with another shy smile. “But yes, cuddle. You’re my best friend Cas and even if you don’t see it this way, this is all kind of a big deal. Cuddling after just feels nice.”

“You want to cuddle with me?” Castiel asked dumbfounded but Dean didn’t seem to be uncomfortable with the arrangement, instead it felt like he genuinely was asking for this.

“After we do anything, yeah. Just for a short while after at least.”

“Okay. We’ll cuddle after.”

A small bundle of nerves settled inside of him as Castiel moved onto the couch and leaned against Dean’s side. He let Dean take the lead from there, throwing his arm around Cas’s shoulders and pulling him in until Cas’s cheek rested on Dean’s shoulder and his arm settled over Dean’s waist. They both kicked their legs up onto the ottoman and turned their attention to the TV to finish their movie.

As they laid there for the remainder of the movie, Cas tried not to let his thoughts cloud his mind but there was one thought that he couldn’t exactly wash from his mind with the smell of Dean’s soap infiltrating his senses:

Perhaps he was a little in over his head.

Chapter Text


Dean could hear his friend, Benny, calling his roommate’s name but Dean refused to turn his head away from the screen where Benny was currently kicking his ass at Call of Duty. He could admit he played the video game a little too much but it was nothing compared to his friend. Benny was far better at this game than should even be possible.

Cas took a while to answer, which meant the guy was probably still nose deep in his textbook.

“Yes?” Dean heard his roommate speak.

“Would you mind looking over my paper when I’m done with it? Dean said he would but you know his brain doesn’t get along with grammar too well.”

Dean had to laugh at Benny’s lighthearted jab. There was a reason Dean wasn’t becoming an English professor in his future; he wasn’t terrible with words but he definitely wasn’t as good with them as he was with math. That’s why engineering was his career path. “Can’t help it, I’m a numbers guy.”

“Sure, I can look over it,” Cas agreed kindly. “Is it due soon?”

“Not until next Friday but I’ll be done with it by tomorrow.”

“Just email it to me.”

“I owe you.” Benny groveled and Dean could hear Cas’s laugh in return.

There were a few more minutes of conversational silence, with only the sounds being Dean cussing at Benny for killing him, yet a-fucking-gain, even though they were on the same fucking team, before Benny started chatting again.

“So you two have any plans for the 3 day weekend at the end of the month?”

With one more failed attempt to get revenge on his friend, Dean chucked his controller onto the ottoman, officially throwing in the towel.

“Not yet,” Dean answered for the both of them, knowing already what the other guy was planning to do for break. “Tickets back home cost too much for that weekend and Cas’s dad is back with his psycho ex so he’s avoiding that shit show.”

Benny’s eyed both of them with a confused stare. “Psycho ex?”

“Kali is… an interesting character,” Cas offered diplomatically and Dean could feel himself roll his eyes. His friend had a knack for underplaying other people’s shortcomings.


Dean eyed his friend exasperatedly, not allowing him to just leave his description of his dad’s girlfriend at that. He knew Cas wouldn’t mind telling Benny this stuff, or else he wouldn’t have pushed for more details. Dean also knew Benny would get a kick out of some of the stories Cas had up his sleeve about Kali.

Cas must’ve agreed since he turned towards Benny, abandoning his homework, and looked ready to dish it all out.

“She has an explosive personality and tends to break things whenever Gabriel does anything against her wishes.”

“Like leave a dish on the counter…” Dean chimed in, emphasizing just how ridiculous Kali’s tempers were. He could never forget the time Cas face timed him on summer break one time to show Kali throwing Gabriel’s clothing out of the window just because he’d left the toilet seat up and she’d fallen in.

“She is very much hot headed and likes to know everyone just how displeased she is by throwing things and breaking anything in reach,” Cas agreed, laughing despite himself. “She also doesn’t really like kids so that caused some problems between them.”

Despite the eyeroll Cas had ended his sentence with, Dean knew deep down it kind of bothered him. It seemed to have perturbed Benny as much as it did Dean the first time he’d heard that too since the other man grimaced and asked, “Why’d your dad stay with her?”

Cas sighed, “She’s a former porn star and my dad thinks with his downstairs brain about eighty-five percent of the time.”

He had to chuckle at the monotone way Cas delivered that sentence. He looked over at their friend and waited for Benny to pick his jaw off the ground because, yeah, Benny and Dean were definitely like-minded when it came to these things. Cas’s dad managed to sack a porn star? It wasn’t that Gabriel was bad looking but he was shorter than even Cas and usually dressed pretty goofy but he was funny as hell so Dean wagered that helped a lot.

“Dean, have you met her?” Benny asked wide-eyed, “Tell me you’ve met her.”

“Sorry. Can’t say I have.”

“Damn, wanted to know if she’s hot.”

“Trust me, I want to know the same thing,” he replied with a mirrored eye-waggle to Benny’s. The two laughed when Cas called them pigs.

What Dean didn’t mention out loud was that he’d, absolutely, looked her up the same day Cas had told him about the fact that his on and off again ‘step-mother figure’ was a porn star. And Dean had almost gotten his rocks off to one of her videos until it finally dawned on him that Cas’s squirrely looking, hyperactive, always calls him ‘Deanie Weanie’ dad had been with her. Then the video was more revolting than anything.

“I assure you both that she’s beautiful,” Cas said with a over exaggerated eye roll, “but trust me when I say when you see her throw a frying pan at your dad’s head, the beauty fades a few degrees.”

“Crazy is always hot. Always.” Dean jokingly affirmed. Just to get Cas to stick his tongue out at him petulantly. Needing to up the ante Dean threw the bird his friend’s way, pairing it with a flashy wink.

When their little silent banter ended, Cas seemed to have officially given on with whatever he’d been working on and sloppily piled his work onto his desk before moving around their room to shrug on his overcoat and tuck his wallet into his pocket.

“Where’re you going?” Dean asked, curiously.

“Dinner with Hannah.”

There was a dramatic sigh from the big man in the room and Dean glared over towards where Benny was looking at Cas with a dramatic frown. Dean knew instantly what Benny was going to say and by the ‘This again?’ look on Cas’s face, Dean’s best friend knew it too.

“Cas… when are you going to let me have her number?” It was almost pitiful the full-fledged whine Benny’s voice undertook every time he talked about trying to get Cas to be his wingman with Hannah. He’d been at it for almost a year but Cas was just as protective over Hannah as any.

“I think the better question is when are you going to get the nerve to actually ask her out yourself?”

“You know she’d just laugh in my face,” Benny argued. Dean nearly pulled out his phone to capture a picture of the burly man looking like a sad teddy bear.

“Maybe if you hadn’t spilled a beer all down your front the first time you tried to talk to her she may think of you in a higher regard,” Cas teased, knowing just how to embarrass the man.

Benny didn’t seem deterred though.

“One day I’m gonna win a date with her.”

Cas patted himself down again, checking he had everything he needed. “I won’t hold my breath,” he jeered, making Benny feign heart problems.

Right before Cas was leaving, Dean as usual called out, “Hey, which place you guys going?”

“Burger Time.”

“You have your phone?”


“Okay. Text me when you’re on your way home.”

“I will.”

“Be safe. You’re walking Hannah back right?”

“Of course.”

“Okay cool. Have fun.”

He didn’t think anything of their conversation until Benny busted out laughing a few moments after Cas shut the door. “You’re such a mom. Do I need to run back out there and make sure he has clean panties too? A snack for the road?”

“Shut up, asshole.”

He threw a solid punch into the meat of Benny’s arm for good measure.

“I get it though,” Benny admitted after landing a solid hit into Dean’s own arm. “Me and Ash ask the same questions. Too many crazy things happening in the world these days.”

Dean shuddered at the thought. There were too many fucked up things happening in the world but a disturbing amount at college campuses as well. He knew for the most part that their campus was safe but one could really never be too careful. Dean said as much.

“I agree.” Benny replied thoughtfully. At that moment Dean got up to go grab himself another beer, offering one to his friend who kindly turned it down. “So, how’re you doing, brother?”

Dean slumped back into the couch and shrugged at his friend. “I’m good. Why?”

“Haven’t seen a lot of you since the semester started.”

A wave of shame hit Dean a little at the words. He had to admit that he hadn’t been as social the past few months but especially less social in the most recent weeks with the sudden turn of events between him and Cas. He tried to play it cool though and not let on that he was keeping a giant secret.

“I’ve just been here. Mostly bumming around.”

“Getting old?” Benny joked. “Too cool to go out now?”

“Just not really feeling it, you know?” And that was the truth. Ever since coming back from summer break, Dean just hadn’t felt so up for going out and partying anymore. He hadn’t exactly been a big party man before but every few weeks he could be talked into going out with Benny, Ash, or Vic. He’d manage to drink a few, pick up some chicks, and have a good night but little by little it stopped being fun to him.

He found the time he got to sprawl out on the couch with a pile of junk food and Cas sitting next to him in his vile looking beanbag, was the way he liked to spend his time best. And now? Now with the new arrangement they had going, he couldn’t find any excuse to actually want to go out.

“Yeah, I get it,” Benny agreed. “The freshman coming in look like they’re fifteen and act like they’re ten. It’s not as fun as it used to be.”

Dean nodded in solidarity. He realized too that he had been missing his friends. Benny was an awesome dude and a lot of fun to hang out with. It was shame that Dean hadn’t been seeking out his company as much anymore when they were still able to. Adult life was right around the corner, after all.

Benny must’ve had the same thoughts. “We need to hang more though. If I have to listen to Ezekiel and Gadreel go at it one more time I’m going to lose my mind.”

“They still fighting?”

“Then making up. Then fighting. It never ends.” Benny grimaced. Both he and their friend Ash had reluctantly accepted moving into a four-bedroom home with Benny’s older cousin Ezekiel and Ezekiel’s on and off again boyfriend Gadreel. But Benny and Ash justified that the rent was cheap and Zeke always paid for the groceries so they couldn’t complain too bad.

Dean made a noise of understanding. “Wanna go for dinner tomorrow? I can ask Cas if he’d be up for it.”



“Thanks chief,” the big guy said with a head nod. In his pocket his phone chimed and Benny checked it quick before giving Dean a guilty smile. “I gotta head out, Andrea wants to meet for food right now.”

“Isn’t it weird for you?” Dean asked before he could help himself.


He didn’t know what actually compelled him to ask the question aloud but now that he had, he realized how much he wanted to know the answer. “Is it weird to be friends with her after everything that happened? You two dated for like three years and now you’re just best friends like it’s nothing? How does that even work?”

Benny gave him a weird look but answered it regardless. “We don’t really act like nothing happened, to be honest. We had a relationship, it was great and all for a while so yeah it was a little weird at first just being friends but now? I don’t know, brother. I just want her in my life but I don’t want to be with her and she feels the same.”

“You really think you can be friends with an ex? Someone you’ve been… you know… with?”

“Lot’s of people are friends with exes. Just because you’ve hooked up doesn’t mean that friendship isn’t an option after that.”

Dean nodded, trying to feign some sort of understanding. “I guess I’ll just take your word for it.”

“Is something up?”

“Nah. I was just curious.” He brushed off, trying to quickly mask any sort of ‘I’m kind of sticking my dick in Cas’s face and am freaking out that we won’t be friends after this’ that might have been evident on his face.

If Benny believed Dean or not, he didn’t say, but another chime of his phone had him heading towards the door.

“Alrighty then. See you tomorrow. Text me when you’re hungry.”

“Later man,” Dean called out. He sighed to himself when he heard the door click shut.

He was alone in the dorm and that meant he was alone with his thoughts and he was kind of freaking out. Just a little.

He loved this new deal he and Cas had going for them and he was completely relieved that nothing felt awkward either They were as normal as ever, they still joked around, still worked on homework together, still watched the same lame TV and played video games. Nothing changed except now, Cas would ask Dean if he wouldn’t mind if he practiced his blowjob techniques on him in the middle of whatever they were watching. And it was so normal that it was making him wonder when the other shoe would drop.

At some point the comfort would wane and he’d be left with an awkward mess where his friendship should be, right? Wasn’t that what every single movie about friends with benefits told them? It worried the shit out of him.

Cas had been an instant part of his life and Dean dreaded that this arrangement would ultimately rip that from him. He knew people like Benny and Ash and even Victor were good friends to him but they didn’t get him on the same level that Cas did. They didn’t notice when he started to feel worn out from putting on his charismatic front. They didn’t understand that he hated when people tried to get too personal with him, asking him prying questions about what he was like as a kid.

It was safer to keep a wall around himself. One that he only let his family into and that included Cas. And Cas understood that. Cas didn’t have much in the way of family so he understood why Dean would keep the people he cared about close and keep his heart even closer.

What was going to happen if this whole situation blew up in his face and he lost the one person outside of his family who he managed to let in?

He knew it was gonna hurt like a mother and Dean was scared out of his wits. But despite the rational solution being to stop while they were ahead, Dean kept telling himself that he made Cas a promise and he didn’t want to let his friend down.

Speaking of.

Cas: Leaving Hannah’s now

Cas: Did you eat?

Me: No

Cas: I have a burger and fries for you. They’re cold so I apologize.

Me: Thanks buddy

Benny said it could work though. It worked for him and Andrea and they’d even been engaged so there had to be a way for nothing to change between him and Cas when this was all over.

He’d make damn sure of it.

Dean was currently flat on his back huffing up at the ceiling, willing his heart rate to go down because oh fuck… that was a good one.

He’d have thought that after nearly two weeks of Cas giving him seemingly endless head that the orgasms wouldn’t be so intense but Cas was very keen on improving his technique, and he sure as hell had.

It seemed somewhere in the last few days Cas had mostly gotten over his self-consciousness. At first he questioned everything, checking with Dean almost constantly if what he was doing was right or pleasurable. He’d also apologize profusely each time he tried to suck down more of Dean’s length and couldn’t help but induce his gag reflex. Each time Dean heard an apology slip from Cas’s lips Dean wanted to punch himself in the face.

He wanted to shower Cas with all the praise he could think of because Cas was a fast learner and Dean was meant to be his teacher in all this and help him know that he was doing amazingly. It was just hard for him to get the words past his lips, but he vowed he’d try harder.

Right then, Cas was still between his legs on the bed after climbing onto Dean’s bed that afternoon after Dean woke up from a nap, asking if he could practice again. He was currently staring at Dean as he came down like usual. It seemed to be something that Cas liked to do, watching Dean come down from an endorphin high. Dean supposes it made sense—he used to like seeing just how intensely he’d made his partners come; gave a person a bit of an ego stroke to know they did that. Like always, when Cas seemed satisfied with watching over Dean, he moved to pull away to clean up and like always Dean had to ask:

“You need to get off? I don’t care if you stay out here.”

It wasn’t surprising when Castiel responded with, “No. That’s alright. I’ll just go shower.”

His same answer every time.

It’s not that Dean necessarily wanted to watch Cas get himself off or something (maybe he was intrigued) but Dean had just been wondering why it was that Cas didn’t seem to bother to do it right away. Why was it always cleaning them up and then taking care of himself in the shower? He knew that Cas got turned on by their arrangement (it was especially evident when he wore sweat pants) but he never seemed to act on his arousal right away.

Dean didn’t mind if Cas wanted to do it in front of him. He wanted this to be a mutually beneficial deal and he felt increasingly more selfish each time Cas had to take care of himself in the bathroom while Dean got to bask in the afterglow of some pretty awesome orgasms.

Perhaps it was his still bliss-hazy mind that had him speaking up this time, stopping Cas before he could climb off the bed. “Wait. Why do you always go do it in the shower? I told you, I really don’t mind if you do it out here.”

For some reason the question made Cas a little shifty. “Uh, no reason.”

Trapping his friend with his legs, Dean gave his best friend his best menacing look. Well, as much as he could with his lower half buck-naked.


Cas adjusted himself just a little, clearly trying to hide his evident arousal. “I just… we didn’t agree on it.”

“On what?” Dean asked, still keeping his legs around his friend. Cas wouldn’t look him in the eye.

“It’s not about me.”

“What do you mean?”

Cas sighed heavily, looking like he was trying to find the right words.

“We agreed to help me learn how to pleasure another person. I already know how to pleasure myself so there’s no reason for you to deal with that too.”

A wild mix of thoughts and emotions swept through Dean and it took him a moment to shove them aside enough to focus on Cas. He hated that Cas thought this wasn’t about his pleasure too, and it made him feel disgusted with himself that he’d already let Cas spend weeks thinking that he was just there to get Dean off. He didn’t know how he was going to word it but he knew he needed Cas to understand that Dean wanted this to be as good for his friend as it was for himself.

“I’m not cool with that,” is what came out of his mouth.

Cas finally looked up at him, worry clear in his features. “What?”

“This isn’t just about me, dude. It’s a two person deal and if you’re not enjoying yourself then maybe would shouldn’t…” he moved to pull his legs away and sit up but Cas’s palms landed on his shins, keeping him there.

“I am enjoying myself.” Cas insisted, looking even more worried than before.

Dean bit his lip as he tried to think of what to say. The thought of letting it go on the way they were wasn’t settling right with him. If he knew Cas saw this as a one-sided arrangement where Dean would get his rocks off and Cas would be exiled to the bathroom to get any pleasure, it wasn’t going to work.

He wasn’t sure if he’d want to return any of the favors but he did know he wanted Cas to stick around, and he really, really wasn’t opposed to being there if Cas got himself off right after. If Cas didn’t want him to watch, that was fine, but Dean didn’t want him leaving.

“We uh—we said we’d tell each other if we didn’t like something and I uh—I don’t like this just being about me,” He explained. “You should be able to get off too, especially if you’re turned on by what we’re doing.” He backtracked then, realizing he’d been assuming Cas was even aroused by Dean. “You are turned on right? I mean I could always go into the bathroom while you watch something or do what you gotta do I just don’t want you thinking you have to leave right after because you don’t.”

Cas’s face relaxed significantly, a near smile gracing the edges of his lips.

“I am turned on by it,” he admitted. “I am.”

He felt relief wash over him hearing that and seeing Cas more relaxed.

“Then you should feel good from it too.”

Dean could tell Cas was mulling it over for a minute before he said, “I’ve never, uhm, I’ve never masturbated in front of another person.”

“That’s okay,” Dean ensured despite the fact that his insides felt a little warm at the thought—he ignored them for now, choosing to focus on Cas’s needs. “Do you want to try?”

“Right now?”

“Why not?” Dean shrugged but Cas frowned and looked down at his own crotch.

“I’m not fully…”

“Oh,” is all Dean could say. He felt stupid for talking so much that Cas didn’t even get to enjoy getting off. He wanted to apologize but Cas was talking before he could manage.

“Uhm I think I could, you know, try again?”

Cas looked nervous but Dean was already nodding his head.

“Yeah, you should.”


They stared at each other for a while, both a little unsure where they should start. It dawned on Dean that Cas was looking for his cues, because Dean was supposedly the more experienced one and was supposed to teach the other man how to do all this. Only, for some reason, Dean felt new to all this too.

“How do you want to?” He asked. “My bed? Your bed? Do you want me to leave?”

“No. No, you can stay.” Cas said quickly. He appeared to be looking around the room and their current situation on Dean’s twin bed. “Uhm, can I stay here?”

“Yeah, yeah, that’s fine.” He only just realized that he was still naked from the waist down and his leg was still draped over Cas’s lap. He quickly shuffled himself to sit up against the headboard and pulled the corner of his comforter over his lap. Not really knowing what Cas wanted from this, he had to ask, “Do you want me next to you? Or like at the end of the bed? Or like you leaning against me or something?”

He wished he could read Cas’s mind right then because his friend looked an equal mix of terrified and amused. Dean also really hoped that the color showing up in Cas’s cheeks was from arousal and not from embarrassment.

Cas swallowed hard before saying, “Maybe, maybe leaning on you?”

“Yeah, yeah. How about you sit between my legs,” Dean suggested, before he could stop himself.


Cas started to awkwardly scoot over towards where Dean was sitting and Dean felt compelled to ask, “You okay?”

“I’m nervous,” his friend admitted easily and Dean couldn’t really blame him.

He tried to be reassuring as he said, “That’s okay, I’m gonna help you.”

“Dean, no. I can’t ask that of you.” The dumbfounded look on Cas’s face was enough to make Dean realized what it sounded like he was offering.

“I’m not gonna jack you or anything, I just want to help you keep in the right head place.”

“Wouldn’t that be—Isn’t that weird for you?”

“No weirder than you sucking my dick every day. So get over here, pants off, your back to my chest.” He knew he sounded more confident than he felt but he wanted Cas to be comfortable enough with him to do this. He waited with almost bated breath as Cas started to strip out of his pants. He tried not to look at his friend’s dick but… he was curious alright?

When Cas finally crawled back onto the bed and moved between his legs, Dean wondered if this was a horrible idea…. But it was too late now. He’d already committed. He shifted just a little to make sure nothing was accidently rubbing up against his best friend before pulling Cas’s back solidly against his chest. “Comfy?”

“Yeah.” Cas said with a trembling voice.

Careful to keep his hands solidly on his own thighs, Dean figured it was now or never. “Okay, show me what you do.” He commanded, though is sounded a little shaky to his own ears.


He could feel Cas’s nerves from the whole situation and he hoped that his own weren’t showing but he wanted to do this for Cas. The whole point of this arrangement was to help Castiel feel more confident in himself as a sexual being and Dean could at least do this for him! He just needed to offer a little encouragement.

“Dude, you’ve seen my dick up close and personal for the past few weeks, there is nothing to be embarrassed about. And as far as dicks go, you’ve got a decent one.” He commented plainly. It wasn’t like it was a weird thing to tell his friend he had a nice cock. It was just a gesture to help his friend out. That’s all.

Still Castiel didn’t seem eager to get on with it even though his dick was twitching in a way that said otherwise.

“Dean, really, I can just handle this in the shower, it’s not a big deal.” It was the half-hearted argument that had Dean growing a little more stubborn. Cas seemed to want to do this—so Dean was sure as hell going to help him out. He tried to quickly think of ways he could make this a good experience for Cas, without touching him like that. Praying that he wasn’t wrong, he hoped that his voice could be considered sexy if he lowered it enough, so he chanced that maybe it’d work for Cas if he whispered against the ear near his mouth.

“Touch yourself.”

It was the shaky gasp that told Dean it’d worked and he almost melted in relief but was too distracted by the fact that Cas started to stroke himself almost instantly. He tried not to watch too intently, not really sure if he should but after a few moments of Cas’s breath staying even Dean had his eyes locked intently on the dick pushing in and out of his friend’s fist. It didn’t look particularly stimulating and Dean wasn’t sure if this was Cas’s usual method or if he was just a little trigger shy from Dean watching.

Regardless, Dean wanted his friend to be confident with this—some people got off watching their partners take care of themselves so this was something Dean felt Cas should learn. When he couldn’t take watching Cas half-heartedly stroking himself, he snatched Cas’s wrist in his own hand and brought his palm to his friend’s lips. “Lick.”

Obediently as ever, Cas did as asked making sure to get his palm thoroughly wet before bringing it back down to continue his touches. He seemed reserved still… in a way that was starting to make Dean wonder if he’d broken a rule and pushed Cas to do something he really didn’t want to do. Should he have just let Cas take care of himself in the shower?

“Could you… could you tell me where your mind is at right now? I’m starting to worry that I’m making you do something you don’t want to do.” Cas’s hand stopped moving as he tried to look over his shoulder at Dean.

“No! Dean, no, that’s not at all it. I just… I don’t want to keep you here for too long… and this wasn’t part of our deal and you don’t need to help me. It’s supposed to be about me pleasuring you.”

“No it isn’t. Cas, our agreement is for me to teach you how to pleasure a partner. And believe it or not, buddy, most people think it’s hot as fuck to watch their partners get themselves off. So just think of this as another learning experience… you do this confidently and you’re going to have whoever you’re with coming in their pants.”

“Really?” Cas asked skeptically.

“Take my word for it.” He couldn’t bring himself to divulge his entire thought because he didn’t know quite the right way to say that even he found the idea of Cas getting off a little arousing if not for the sole reason that Dean wanted to see his friend as satisfied as Dean has been.

“I don’t have to be here though… I could do this on my bed if you’d rather have some space.”

“Stop. That’s not a sexy thought. I really don’t mind. Just, stop overthinking this okay?” He didn’t like that Cas’s self-consciousness was peeking through. Dean knew it was his fault again. He just threw Cas into an awkward situation and was doing nothing to guide him along. He needed to step up to the plate. “What turns you on?”

“I don’t know.”

“You do… you do know what turns you on.”

“I like…” The words seemed to not want to come out. “I, uhm, I like…”

“Tell me,” Dean whispered again in his ear making Cas shiver, he knew he’d remember this little trick for the future if he got the chance.

Cas’s response came out in a rush.

“I like the noises you make.”

Dean couldn’t help but smirk a little. Who didn’t have a sex noise kink? It was always so thrilling to hear the way you were making someone feel. Now it was Dean’s turn to try and drive some of those same noises out of Cas. Knowing he wasn’t brave enough to use his hands, he worked with the only tool he had: his voice.

“Yeah? You like hearing me?” He could feel Cas shaking against him and hoped to all things mighty this was working.


“Do you know how good it feels when your mouth is on me?”


“There you go, keep going.” He felt Cas press more firmly against his chest, as his friend’s hand started moving steadily more quickly. Something about this made Dean feel more bold, and the praise he’d been too shy to give his friend came pouring out. “You’ve been so good at all of this, you know? Every single time it’s so good. Fuck. I had no clue how awesome it’d be when we started. It takes everything in my to hold back.”


There it was. That’s what he was looking for.

“There you go. Does it feel good?”


Dean felt his hands twitching. He didn’t know what came over him but suddenly he felt this undeniable desire to touch. He kept himself in check fisting the blanket around his hips while he as Cas’s orgasm started to creep up on him.


“That’s it. Don’t stop. Are you close?”


Cas’s head leaned back onto Dean’s shoulder as he panted into the air above him and Dean couldn’t keep himself from not touching. He wrapped one arm around Cas’s waist as the other pressed into Cas’s chest, keeping him firmly against Dean’s chest.

“It’s gonna feel so good. Come on.”


He could feel Cas quivering against him. Could see his friend’s toes curling near the edge of the bed. Dean’s own body felt like it was building up too. “That’s it. Don’t hold back.”

Hardly a beat later Cas’s head pressed firmly back against Dean’s shoulder as his body began spasming with his release. Dean’s arms held him tightly, keeping him from writhing too hard. “That’s it. So good. That was so good,” he babbled into Cas’s hair.

After a while, Cas’s spasms slowly died down to trembles. Though Dean had never seen his best friend come before, he figured it was safe to bet that that had been an intense one. So, he had no problem allowing Cas to rest up against him until his limbs came back to life.

Dean’s dick was one hundred percent back in the game so he skillfully tried to keep his pelvis angled away from the small of his best friend’s back while he waited.

“That… that was…” Cas let his voice taper off into some mild pants, still trying to connect his mind to this mouth. It made Dean smirk in satisfaction.

“Really fucking good, huh? How do you feel?”

“I didn’t know it could be so… intense?”

He had to admit that he felt a little proud that he was able to assist in getting his best friend to feel that level of pleasure.

“Never felt like that before?”

“Not even close.”

“Now you know what you’ve been missing out on. It should always be like that.”

“Always?” The awed wonder in Cas’s voice had Dean chuckling a little.

“Mostly. If you’re doing it right.” He couldn’t bring himself to lie to his friend, even sarcastically, because the guy obviously knew first hand that not all orgasms were quite as earth shattering.

They settled on the bed a little, almost in some semblance of a cuddle before Cas finally sat up. He angled himself off the bed a little before turning to Dean with a grateful look on his face.

“Thank you, for that.”

“It’s what I’m here for.” Dean shrugged off. Cas still had a penchant for thanking him for their arrangement and Dean didn’t want to always shut him down for it. “You wanted to learn these things so I’m here to help.”

“Would you like me to take care of yours?”

Cas’s eyes lowered until they focused on the obvious tent of the sheets were Dean’s dick was fighting to be seen. A very selfish part of Dean wanted to scream yes because he knew just how good it would feel to get Cas’s mouth on him two times in one day but a bigger part of him couldn’t bring himself to be that kind of guy.

“Nah. I got it. Thank you though.”

Dean finally allowed Cas to get up from the bed with a teasing appreciative whistle that had Cas blushing just enough.

As Cas was making his way to the bathroom Dean called out, “Are we still meeting Benny for dinner?”

“Yeah. Mind if I shower first?”

“Go for it.” Dean responded happily.

He’d never admit to watching his best friend’s naked ass walk towards the bathroom or that fact that he came in under a minute once the door had shut.

Nope. Didn’t happen.

Sunday found Dean sitting on Benny’s couch with his friend and Ash and a few other of their mutual friends watching the game. He had to laugh a little to himself because in the past few months he’d seen his friends less than he had in this entire weekend. It was nice that he was getting out of his dorm and being fed food he didn’t have to pay for but Cas was still stuck at the dorm since he had an assignment due that night for his creative writing class and he’d effectively kicked Dean out even though Dean usually didn’t like to be out of the dorm on Sundays. Apparently he was a distraction

With half of his attention on the game and half of his attention on the meat lover’s pizza he was cramming in his face, Dean tried to pretend like he wasn’t wishing he were in the comfort of his own rickety futon. He really just couldn’t get into the game, which was the whole point of coming over to Benny’s since the other guys were constantly hooting and hollering when things went their way. Dean didn’t have any particular team he was rooting for and really when it came to sports, he only rooted for the Cowboys just because he knew it pissed Bobby off more than anything. There was nothing funnier than seeing the man turn bright red while he talked about the Texas team. But here, these were two teams that he could possibly only name their quarterback just because the guys in the house were referring to the players as if they were old friends.

In sum he was pretty bored. It was nice chatting with his friends and seeing Ash get progressively more stoned as the night wore on but if Dean were being honest with himself he couldn’t stop thinking back to his dorm. At least there he and Cas could watch something that interested both of them. At this point he’d even go for watching the one documentary about some girl who was shot in the face but lived to fight for education… he couldn’t remember the name but Cas had talked about the girl for days, detailing on and on about how influential she was. (Dean asked him to wait to watch the documentary together).

It was a relief when he saw Cas’s name on his phone. He told his friend to text when he finished to see if Dean were still at Benny’s to have Cas come over. Having Cas around might make the evening more fun. At least Cas could add in his friggin’ hilarious voice dubs for the events happening in the game. It was a running joke that Cas would lean over to Dean and start making hysterical dialogue for what the players were saying on the field. It made Dean nearly piss himself every time.

Cas: My assignment is finished.

Me: Come finish the game at Bennys

Cas: I was thinking we could you know… ?

Dean nearly choked on his pizza and tried to play it off cool despite a few weird looks from the guys.

Quickly he typed out:

Me: On my way

He was only a little ashamed he let his dick take the driver seat in replying to Cas. He practically jumped off the couch in his haste to get out of this house and back to where an insanely amazing blowjob was awaiting.

“Hey guys. I’m gonna head out.”

“The game’s not even over!” Benny protested, eyes still glued to the game.

“I know but I just remembered I have homework due for my morning class that I haven’t even started.”

There was collective booing from all the guys that Dean handled with a very sophisticated middle finger in the air.

“Dumbass. Get outta here.” Ash called after him when Dean’s hand signal was met with a matching pair in the air.

“Let me know if you want to hang out sometime this week.” He called out to all of them, mostly as a formality.

“Later Winchester!”

He tried to not allow himself to run back to the dorm but his limbs were without a doubt taking him across campus at a much faster pace than his usual stride would. He had to admit that there was something thrilling about the fact that Cas had texted him to get some “learning” in. Something about the possibilities of what he’d walk into… would Cas be eagerly awaiting him? Would he want to do this quick and dirty or would he want to draw it out? His friend had definitely been having fun with trying to draw out the buildup lately so Dean had a feeling he’d be up for a little of that at the moment.

But whatever Cas might have been planning suddenly was pushed to the backburner when Dean walked into their room. Dean watched his friend hop up from the couch, his hand flying away from where it had obviously been down the front of his pants and suddenly Dean was filled with inspiration.

He strode across the room with more confidence than he was actually feeling because deep down he wasn’t one hundred percent sure Cas would be up for this, but of course he’d give him the option to back out. He wagered Cas would like it though.

“Take your pants off.” Dean requested in a low voice.

“What?” Cas stammered.

“Take your pants off.” Dean said once more, twisting his voice to the same cadence he’d whispered in Cas’s ear a few days prior. It was then that Cas’s eyes widened in intrigue, like he understood that something awesome was going to take place. In a matter of some clumsy minutes later Cas was bare from the waist down. “Touch yourself.” Dean commanded next, watching as Cas’s hand instantly wrapped around himself. “You up for trying something?”

Cas looked a little unsure for a moment before he nodded his head.

“You cool with being on your knees?”

“Yeah,” his friend said breathily.

“Okay, on your knees, but don’t stop touching yourself, alright?”


With the sight of his best friend falling down to his knees, Dean instantly started fumbling with his belt and tugging his pants all the way off until his bottom half was left bare. He was without a doubt already hard so it didn’t take more than a few satisfying strokes to know he wasn’t going to last more than a minute.

“It you don’t like this or your knees or neck start to hurt, just tell me, okay?”

Something about those blue eyes peering up at him made Dean feel a little weak in the knees but he steadied himself with a few breaths.

“I will,” Cas promised, voice like gravel. His lips parted, inviting Dean to trace the head of his cock against them and Dean didn’t resist the pleased sound that escaped him. Cas’s hand suddenly rested warmly at Dean’s hip, steadying himself, but flew back down to his lap when Dean looked down at him.

“No, it’s alright. You can touch me just don’t stop touching yourself either.”

Cas’s breathing stuttered a little. “Okay.”


Cas wasted no time then opening his mouth and taking Dean in. Wanting to let Cas take this at his own speed, Dean settled his hands gently on the sides of Cas’s head, loose enough that they were barely touching.

It was still slightly terrifying to know that he wasn’t just getting head from anyone but from the person he called his best friend. Even so, as each day went on and Cas showed more enthusiasm for perfecting his technique, Dean couldn’t help but let his self-consciousness fizzle out. He felt emboldened enough to let out all the sounds he’d been holding back with Cas, now having also verbal affirmation that Cas wasn’t put off by his sighs of pleasure. This time, Cas’s own moans matched his own. Dean couldn’t help but sneak a glance down at the other man, whose eyes were now locked on his. Looking further, Dean could see Cas’s hand moving rapidly over his aching erection and he was certain Cas had to be close.

“Does this turn you on?” He asked aloud.

All Cas could do was moan as he tried to frantically nod his head with a mouth full of Dean.

“You’re so fucking good at this. Feels so good,” his words were breathy but holy fuck did it feel good.

It was evident enough that Cas was really into this too and Dean didn’t know if he could pry his eyes away from the sight if he tried.

It might’ve been a little sloppier than some of the other times Cas had sucked him but seeing Cas looking up at him and hearing his friend’s own pleasured sounds were sending him racing to the edge.

Right as he was about to tell Cas to pull off, his friend’s eyes screwed shut as his orgasm washed over him, and that sight did nothing to help Dean stave on his own. Not thinking, he reflexively gripped Cas’s hair tightly and pulsed down his friend’s throat until he had nothing left to give.


Weakly, he sank down on the futon as he attempted to catch his breath. He didn’t care that he was butt ass naked on the couch, nor did he care to try and have some decorum and cover himself. Instead he just turned his head toward the man he called his best friend. Cas looked a little wobbly as he tried to get up off the floor.

“Come here.” Dean called out, voice a little hoarse from usage.

“I should clean up.” He protested, his knees popping a little as he stood.

“I said come here.” Dean countered, reaching his arm out to lightly grip Cas’s wrist.

“But we’re a mess,” Cas gestured, mostly to himself. Dean flicked Cas’s sweats from up off the ground and told him to use that before tugging on his arm to get him onto the couch.

Dean kicked his legs up onto the ottoman as Cas settled into Dean’s side, turning his body just enough to rest his cheek on Dean’s shoulder. Without hesitation Dean enclosed his arms around his friend’s shoulders, and waited for Cas’s arm to drape over his waist before speaking. “Are you okay?”

“Of course.”

“That was…” He didn’t know where to start. Fucking amazing and what my spank bank will probably have on replay for years to come. Fuck.

Now that his imminent need for release had been quenched, Dean’s mind started to circle with thoughts on how much just happened between them.

“Hey, I’m—I’m sorry for not telling you when I was going to come, I should’ve—”

“No, it’s okay, really. I think liked it,” Cas’s tone left no room for lies which was a relief and let Dean’s praise come out easier.

“That was really good. Like really fucking good.”

“It was?”

“Did you—did you like it? Being able to get off at the same time?” As much as Dean wanted to see Cas’s eyes when he answered, there was still something inside of him that couldn’t bring himself to peer down at his friend when they laid like this. Some line between too intimate and too… something always stopped him.

Cas didn’t seem to mind the lack of eye contact at these times. “I did. A lot.”

“I think it’s safe to say you’ve officially graduated from Blow Job University.”

There was a bittersweet, but mostly bitter, feeling deep in his chest as the words fell from his lips yet there was no way to deny their truth. Castiel had asked for assistance with hand jobs and blow jobs and Dean knew there were only so many ways the other guy could suck his cock before Dean ran out of things to “teach.” It decidedly meant that their arrangement was coming to an end and Castiel could go off and put his new skills to whatever use he saw fit.

Dean didn’t have to like it but he would be resolute that his distaste came from the lack of ‘free head’ he’d be getting… that was surely all it was. And no, there was no reason that a wave of relief rushed through him when Cas hesitantly spoke into the silence between them.

“I should really get my Masters though, don’t you think?”

He laughed in lieu of revealing just how much he found comfort in those words.

“I’m sure there are a few more courses you could take.”

Chapter Text

“I think I managed a butt dial successfully this weekend.”

Castiel waited patiently as Hannah took a moment to compose herself after choking on her coffee. He knew by her reaction alone he hadn’t worded that correctly. When she seemed finally able to breathe correctly again, the look on his friend’s face was beyond confusion, confirming his thoughts.

“How can you butt dial someone successfully?” She was already giggling around her coffee cup, he light blue eyes shining with amusement.

He glared at her as he explained, “I asked… the guy I’m seeing to come back to my dorm so I could perform oral on him.”

His words came out carefully, ensuring he didn’t slip up and say too much.

He’d tried so hard to keep his and Dean’s arrangement to himself. He knew it was no one’s business but his and Dean’s and he wanted to stick by that belief but he didn’t realize how hard it would be to keep it from his best friend.

At first he felt like he did a good job keeping it from Hannah, but seeing her as often as he did, she started to notice that he was acting weird and pestered him long enough to get him to confess. Sort of.

He’d told her the best half-truth he could think of and hoped she’d accept it.

He said he’d met a guy from the university, at a bar, on a Sunday and decided to work out an agreement to mess around. Casual. Nothing that required his best friend to know the guy’s name and Facebook stalk him because Cas didn’t think it warranted it.

He must have done a fairly impressive ‘I’m not going to budge on this’ face because Hannah didn’t question it further and just asked Castiel if he wanted to talk about it. Which he did, immensely. Now whenever they met up, which was often, he’d take some time to update her on his ‘hook ups.’

“Oh god, Castiel. That’s called a booty call not a butt dial.” She hid her face in her hands, messing up her bangs as she laughed into her palms.

“They’re different?”

“I truly hope you’ve never accidently butt dialed someone before and apologized for booty calling them.”

“It would explain why my dad laughed at me once…” Damn his father for thinking it would be hilarious to teach Cas to say common phrases, slang words, or idioms wrong.

He will still never recover from the time he’d told his debate teacher in high school that he wanted to go home and “hit my sack,” because he was so stressed. The detention mixed with the few teases from some of his friends who’d overheard led to one of the first few times he’d been angry with his dad. After that he was much more conscious about saying things incorrectly. He was getting better with Hannah and Dean’s help, but it was a slow process.

“You’re helpless,” Hannah laughed with him. “Anyway, tell me what happened with him. Wait. Was Dean at home?”

She wasn’t making it easy for him, keeping this secret, since every time he mentioned hooking up with his mystery man, she was always so concerned about Dean’s whereabouts. He’d told her he’d been keeping it a secret from Dean too in hopes that she’d never ask the other man about it, but because of that she seemed to want to double check that Cas was doing a good job of keeping the secret from him.

“Dean? No-No. Dean was at Benny’s so he… he wasn’t there,” he fumbled to explain, taking a big drink of his coffee before caring on. “And the guy left before Dean came home. Way before.”

Hannah seemed accepting of his mumbling and merely took to sipping her coffee again and waiting for Castiel to talk and explain what had happened. It was still a little awkward trying to explain his sex life, since he kind of had one now, and didn’t really know what was custom when engaging in those conversations.

“Uh, do you still wish for me to refrain from details?” he asked, knowing the first time he went a little too in depth with his descriptions of tastes and sensations.

Hannah pushed her bangs out of her eyes and propped her chin and her fist. “Yes, please,” she requested, with curiosity.

It took him a little to find out how to say what happened without being explicit.

“It was pretty quick really,” Cas supplied. “He got to the dorm and it was… different than usual but good different. I really enjoyed it.”

Despite Hannah being more reserved and conservative when it came to her own sex life, she was very supportive in Castiel’s own curiosities which he was immensely grateful for. She listened to anything he had to say with rapt attention and gave him advice whenever he asked for it.

Right now though, the crease between her brows was concerning. He wasn’t certain what she was going to say but he knew that he feared that she’d someday express disappointment in him, or judge him for what he was doing.

“You’re happy? With how things are going,” she asked. He could feel her scrutinizing him for any signs of discomfort but he was pleased he could answer her honestly.

“I really am,” he promised. “I believe he is as well.”

He didn’t explain to Hannah that things were going much smoother than he’d ever anticipated. In fact, he’d been certain that Dean was going to freak out over the whole thing and that their friendship was going to crumble yet, that wasn’t the case. Dean was encouraging and helpful and just so normal about all of it, but it didn’t make sense to him.

He knew Dean was straight and that his best friend had only ever been with women and would only ever want to be with them in the future. He was well aware that Dean was just doing him a favor and that the arousal Dean felt was only due to the fact that he was getting oral sex regularly and had nothing to do with Castiel himself. He just didn’t expect to feel like Dean was kind of enjoying himself and seemed to want to help Cas but he wasn’t going to complain.

He might let the noises Dean makes get to him too much and maybe in those brief moments where Dean pulls him into a cuddle, Castiel fantasizes what it would be like if it were all real. He knew it was dangerous to let his thoughts wander away like that but he couldn’t help it. What would it feel like if Dean pulled Cas into his arms because he wanted to, not because he felt responsible for Cas’s wellbeing? What would it feel like if Dean touched him more than just hesitantly, or said Castiel’s name in the midst of his pleasure? He didn’t even know what he would do if he ever heard Dean moan his name and had verbal proof that his own body was the cause of Dean’s pleasure…

It didn’t do well to settle on fantasies though.

Castiel knew he had to pull himself back to reality each and every time. Dean was his best friend who was helping him out because that was the type of man Dean Winchester was. Dean Winchester could never and would never feel anything more for him than just friendship and Castiel was perfectly content with that.

As if Hannah could sense his train of thought, she asked the one question Castiel had been training himself to side-step around quickly. “Do you think... would you want to make it become more?”

He kept his features as even-keeled as possible, knowing exactly what she was asking but not wanting to answer her question. He knew she’d been itching to ask him if he had an interest in forming a relationship with this stranger she’d never met but he didn’t want to completely lie to her. He also didn’t want to allow himself time to think about being in a relationship with someone he’d never have.

“I am curious about intercourse,” he stated, because it was true and knew it technically answered the question that came out of her mouth. He was fine with playing naïve. “I just don’t know how he would feel. I’ve been considering bringing it up soon though. Intercourse would be the next logical step and I’m unsure if there is really any more I can learn through oral.”


Hannah’s face dropped for a moment and Castiel wondered if he’d said something wrong. She looked upset or worried as she asked, “You think you’d want to actually go all the way with him?”

He hadn’t really thought much past trying to side step her initial question so it came as a shock to realize he wasn’t sure if he wanted to answer this one either.

He hadn’t lied when he said he thought it would be the next logical step. It had crossed his mind many, many times that he was weighing the pros and cons of at least asking Dean.

Just the thought of maybe being that intimate with his friend, to cross that specific line sent a thrill down his spine.

He’d never admit it to Hannah, or to anyone really, but now that his orgasms were far more regular than ever, he swore his fantasies were getting more and more intense. Now, in the few and far between times Castiel was left in their dorm while Dean was attending his classes or with friends, Castiel found himself with his hand around his dick and his mind racing with thoughts of what it would feel like to have Dean’s mouth all over his body and the beautiful cock he’d become so familiar with inside of him.

He wanted it so badly yet he didn’t know what to do about it. He knew Dean had only agreed to receive a few hand jobs and a stream of blowjobs from Cas but now what? Every time Cas had to think about putting an end to his ‘learning’ with Dean, dread would overwhelm him. He couldn’t stand the thought of not getting to have these moments anymore. Without the romance, without the relationship, they were still intimate moments between himself and Dean. He hated that once this was all over that Dean would likely go out into the world and have these types of moments with random girls again.

Castiel wanted to keep him all to himself.

He knew it was selfish. He knew he had no right to Dean and no hold over the other man but every time he got to see Dean naked, every time he got to touch Dean’s skin, every time he was the one who pulled an orgasm out of his best friend, Castiel couldn’t help but feel more and more needy. He knew it was wrong of him to not put an end to their arrangement. He knew that growing these feelings was crossing some sort of line, but he couldn’t help himself.

He was selfish when it came to Dean and he wanted more. But what more could Cas offer him if not intercourse?

“It’s been nearly a month since our arrangement has started, it seems like the next course of action, don’t you agree?” Castiel asked, hoping his silence hadn’t given away any of his useless thoughts.

Hannah frowned. “I guess? It’s different for everyone.”

He could tell something was bothering her. “What is it?” he asked.

“May I be honest with you?”

The lack of eye contact Hannah offered him at the moment unnerved Castiel slightly. “You know you may, always.”

It took her a while to start speaking and Castiel felt more and more unnerved with every moment.

“I worry that you might be rushing into things too quickly,” she finally confessed. “I understand that it might be new and exciting for you but having sex is a big deal.” Picking at the sticker on her coffee cup, she took a deep breath and looked Cas in the eye, emotion heavy in them.

“I—I haven’t told you this before because I hate to talk about it but… my—my first time wasn’t the greatest. It was with a guy I thought I was in love with and I honestly regret that it happened. I was so into him that I convinced myself he’d love me back if I gave that part of myself to him and that’s not at all how it worked out. I just—I just don’t want you to make the same mistake. You don’t owe him anything just because it’s been a month. You should do it only if it feels right and it’s truly what you want.”

Reacting, he reached out and gripped her hand, wanting to provide her with whatever comfort her could offer from the opposite side of the table. He wanted to ask her a million questions and hear her open up to him about this but he knew from the sadness in her eyes that this was all she was willing to offer him today.

He was touched that she’d wanted to confide in him and that she cared enough about him to look out for his own heart. She was a wonderful friend and one of the very best humans he knew and it made him angry to know someone had not treated her as wonderfully as she deserved but he couldn’t see the same thing happening to him, not with Dean.

Maybe he was blind because of his feelings for Dean but he truly meant it when he said, “It is what I want and I… I really don’t believe he’d ever hurt me.”

“Everyone who’s been hurt has said those exact words, Castiel.”

He knew she had a point yet he found himself thinking back to the way Dean always asked if Cas was okay… the way Dean pulled him close when they cuddled and made sure Cas was content. How could his friend who cared so much about his feelings hurt him? No, Castiel was sure Dean wouldn’t be the one to hurt him.

“I trust him,” he insisted, looking deeply into his friend’s eyes and pouring every ounce of honesty into his words.

She nodded but seemed to remain skeptical, but it was Castiel’s fault she was in the dark towards the kind of man this ‘mystery guy’ really was.

“Then I truly hope it works out for you,” she added.

“Thank you.” He wanted to get the look of apprehension off of Hannah’s face and ease all her worries but as badly as he wanted to tell Hannah everything, explain to her all his thoughts and feelings, he’d made a promise to Dean and he’d never break it.

“Enough about me. How was your midterm?”

With grace, Hannah accepted his change in topic and indulged him. Yet it didn’t make his mind cease from drifting to her earlier concerns. Could Hannah have a point? He knew she was just looking out for him but he couldn’t help but wonder if she knew something that Castiel didn’t know. Was he being naive about all of this? Was Dean actually going to hurt him?

His gut said no way but maybe his feelings were getting in the way. But when all was said and done, he understood that his and Dean’s arrangement would have to come to an end. He wouldn’t end up hurt over it since he knew what he was getting into from the beginning.

And even though Hannah seemed to think that “going all the way” would make everything hurt more for Castiel somehow… he couldn’t find it in himself to agree with her. Sex didn’t make people grow that much more attached to people, did it? Surely people had casual sex all the time… there had to be other people in the world who lost their virginities to people and didn’t grow insurmountably attached to their sexual partners.

He’d be fine.

He would just figure it all out for himself, thank you very much. He was a big boy after all.

“You can’t be serious.”

“I’m perfectly serious.” Cas declared, ignoring the look on Dean’s face.

“You’re trying to tell me you think that freaking little green Martians are more possible than ghosts?”

“Although Hollywood has depicted aliens as such, I do not think that all aliens are green.”

It was always a good time when he and Dean bantered about random things and tried to beat one another in a debate. More often than not they pretended to not see the other’s point of view just to rile the other up and make the argument more heated. Why they did it, he had no clue, but it always put a smile on Dean’s face.

“Seriously Cas, you believe in aliens?”

“I believe in the possibility that there is life outside of just our earth. Look at the universe, it’s seemingly infinite and yet we think that our planet is the only one in the entirety space capable of sustaining any form of life? Perhaps we could have the most sophisticated life form but even something as small as algae or bacteria on another planet would be proof of alien life.”

“But ghosts could be real too,” Dean insisted, sipping at a beer they’d had hidden in the back of this mini fridge.

“How so?” He challenged, wanting to listen to any and everything Dean had to say.

Dean had a freakish obsession with horror films and ghost shows so much so that Cas often found his friend spending hours watching ghost conspiracies and other videos on the Internet or on Netflix. Cas himself didn’t think that paranormal activity was real but he didn’t outright think it was impossible. Dean however could go on and on about it and had some very valid points about sprit activity but often deflected to jokes and hoaxes as his proof to get a good laugh out of someone. Dean was so much smarter than he let others believe.

“Everyone has a soul or whatever you want to call it and I just don’t get where it goes when we die? Isn’t it possible that it gets released into the universe once we die? Like where do our souls go? I can’t believe that people just stop existing once it’s lights out.”

He relaxed back into his beanbag. “I agree that their energy is released into the universe but there is no quantifiable evidence for the existence of ghosts or spirits.”

“Yeah? Then how do Ghostfacers get all those recordings of spirits talking back to them?”

Cas let out a laugh. “Really? You’re sighting Ghostfacers as your source?”

“Hey, they’re legit and you know it.”

“They’re a group of man-children who run around screaming in a camera.”

Dean didn’t even try and deny Cas’s assessment of the TV show group Dean was so obsessed with, instead he threw a pillow at Cas and shouted, “But they have proof of ghosts!”

“They have audio tapes and records, yes, but how can we know for certain they were not fabricated or tampered with for views?”

“Harry and Ed would never.” Dean growled, though his eyes were bright with mirth. He never really wanted to go into a real debate, just enough to get his friends laughing though Cas would love to pick Dean’s brain as much as he could if he were given the chance.

“You’re never going to admit that you have no real evidence on the matter, are you?” Cas teased, earning him a confident smirk from the other man.


“It’s like talking to a child.”

“You’re a child.” Dean mocked back.

“I’m done. I can’t take this anymore.” Cas threw his hands up and got off the couch, pretending to start packing a few of his belongings into a backpack. He could hear Dean laughing from the other side of the room. “He looks like a full-grown man but he’s really a six-year-old. I can’t do it,” Cas said to himself loudly, wanting to hear Dean’s laugh even more.

“Well fine,” Dean cut in, sounding even more like a snobby kid. “Since kids don’t share, you can go down to the dining hall for dinner and I’ll eat the pizza when it gets here. I heard they have sloppy Joes and Brussels sprouts tonight.”

“For your information I enjoy vegetables.” Cas pointed out.


“You can suck your own dick tonight.”

Dean barked out a laugh and then clasped his hands together, pretending to be begging for forgiveness. “I’m sorry. You’re a wonderful human and you are always right. If you’d like to have the larger slices of pizza, I’d be more than happy to serve those to you. Would you like a beer as well? Or would you like me to run down to the corner store and get you your weird ass green tea? I’ll do anything.”

Cas appeared to contemplate for a moment before he leveled Dean with a smirk. “I did notice there was one more slice of that chocolate peanut butter pie Hannah made. I think I’d like that tonight.”

“Yeah, your mouth ain’t that good.” Dean deadpanned as he sat himself more comfortably on the futon and pretended to dust himself off. He turned towards the TV and kicked his feet up on the ottoman once he was seated. “I’ll take care of my own dick, thanks. You just stay away from my pie.”

The glint in Dean’s eyes when he looked over his shoulder had Cas laughing until his belly hurt.

Two entire pizza’s eaten that night made no one feel very sexy so no dicks were sucked but Dean did share half of his pie with Castiel that night anyway.

Castiel woke slowly. It was Friday and there was no immediate need for getting up and getting ready for classes. The curtains were drawn so it was still mostly grey in the room aside from the orange glow of light coming from behind the drapes. He rolled over to his side and checked his phone and replied back to a few memes Hannah had sent him in the night before chucking it somewhere in his covers and laying to stare at the ceiling.

It wasn’t too early that Cas felt the need to fall back asleep but it wasn’t too late that Cas thought he actually needed to get up and start the day.

He looked over to his right to see Dean across the room sprawled out asleep on his back. The other man tended to always be hot so his blankets were kicked around his ankles and he was only sporting his batman boxers. Usually the sight of Dean in nothing but his boxers didn’t faze Cas since he’d been seeing it for almost four years but now, knowing what was underneath… it sent a thrill down his spine.

He couldn’t resist. Slowly getting up from his bed, Cas stripped from his pajamas down to his boxers and made his way across the room to Dean’s bed and crawled up onto the end of it. He stared down at his still asleep best friend, waiting for the other man to start to rouse.

He wasn’t used to feeling want so heavy that early in the morning but with Dean laying there looking so beautiful, Cas knew his body was only reacting to what it craved.

They hadn’t talked much about things they’d like to try and Cas wasn’t sure if Dean was even interested in waking up to a blowjob, though the thought was on Cas’s mind, and he’d bet all his tuition on the fact that Dean would like it, he still wasn’t sure. Not wanting to do something Dean didn’t want, he shook Dean’s leg, earning only a slight snuffle from his friend.

“Dean,” he whispered a few times to no response.

Nudging his friend’s hip started to rouse the other man but he was still groggy.



“Are you awake?”

“No,” his friend groaned, throwing an arm over his eyes. Cas almost felt guilty about waking him up but the persistent need in his groin overshadowed it.

“Dean?” He asked again, not wanting to let his friend fall back asleep.

Dean didn’t necessarily seem grumpy but it was clear he wasn’t thrilled by it. “What?” he asked sounding vaguely annoyed.

Cas was usually the grumpy morning person so this side of Dean was kind of cute. If only he didn’t have the miles of perfect skin before him, distracting him.

“Do you want me to give you a blow job?” He asked, his voice still mostly a whisper.


Dean was clearly still groggy since his eyes couldn’t open completely.

If his friend really wanted to keep sleeping in, Cas wouldn’t mind. He was horny after all and could easily take care of it himself but with Dean there, he figured why not ask?

“I can give you a blow job if you want?”

His words must have penetrated Dean’s foggy brain because, despite the struggle, Dean’s eyes sleepily focused on Cas as he asked, “For real?”


“Sounds like the best frickin’ wakeup call ever.”

Cas laughed under his breath before lowering himself onto his belly between Dean’s legs. The bed wasn’t quite long enough for this to be perfectly comfortable but with a few shuffles they were able to make it work.

Dean’s breathing was still steady and slow and his eyes dropped a little as he looked at Cas. Just that look alone gave Cas butterflies. How was it that each and every time he got to fool around with his friend, he felt overwhelmingly like the luckiest person in the world? How could seeing Dean half-awake in his boxers on his unmade bed make Cas want so deeply?

It wasn’t fair how perfect Dean was at all times but it did thrill Cas to know he was the one who got to have him, at least for now.

Not wanting to dwell too long in his thoughts he got to work on the task at hand. Just because he could, he ran his palms up Dean’s thighs, marveling at the muscle that Dean tended to keep hidden in loose jeans. His hands found their way to the thatch of hair at Dean pelvis and he scooted forward just a little more to get his face closer to where he was needed.

He couldn’t help himself, he breathed in, tantalized by the scent of his friend that he’d grown so accustomed to. That’s when he got started, wrapping his right hand around Dean’s member in his boxers while his left arm slid up to keep Dean from squirming too much from the sensations.

Dean had been doing a great job at giving Cas suggestions on what he could do with future partners. He always said Cas never needed to try it on him, but Cas found himself wanting to.

With Dean, he wanted to try everything.

Which is why after slipping Dean’s boxers off his legs, Cas had his tongue swirling all around the base of Dean’s cock before sucking each of his friend’s balls into his mouth. He gave them the attention Dean had admitted to liking, through a crimson blush, before Cas sucked the head of Dean’s dick into his mouth.

Wanting more than anything to make Dean feel incredible he opened his mouth wider and took in all that he could and just let himself enjoy giving Dean this sensation.

Eventually fingers found their way into Cas’s hair and pulled just the right amount, making Cas moan around the cock in his mouth. Not long after that he felt Dean’s hips start shallowly thrusting. It made him burn with desire but he pulled away suddenly, a fantasy flashing through his mind.

“Mmm, no. Why’d you stop?” Dean asked, voice deep and gravely.

“Get up?”

Dean looked at Cas a little oddly before complying at sitting up.

“Why?” He asked as Cas tried to crawl up to where Dean had just been laying.

“Just move over. Trust me.”

Confused, Dean shifted over until his back was flush against the wall and there was space for Cas to lie down. Immediately Cas did, settling back into the pillows and looking over at Dean.

“I want to try it like this.”

He might’ve been fooling around regularly with his friend but that didn’t mean he wasn’t still watching porn or thinking of things he wanted to try with Dean that he’d seen in said porn.

“What do you mean?” Dean asked.

“I want to suck you like this.”


With a fond eye roll Cas tapped Dean’s hip. “Crawl over me.”

He waited for Dean to get with the program and shuffle up onto his knees until this pelvis was yet again in Cas’s face.

“You won’t be able to move though.” Dean commented, looking at the way Cas’s shoulders were nearly pinned down from the position.

“Yes I will.”

“How—how will I know if you don’t like it?”

There was legitimate concern in Dean’s eyes and Cas was touched by it, but he was more concerned with the immediate need to get back to the good stuff so he wrapped his left arm around Dean’s thigh and demonstrated how he’d signal if he were uncomfortable. “I’ll push you off me. Come on.”

“Oh. Fuck. Okay.”

Maybe this was just as hot to Dean as it was to Cas because as soon as Dean’s cock was back in his mouth, Cas could practically see Dean’s eyes rolling into the back of his head. But what really got him was the way Dean moaned so dirty that Cas felt it all the way to his toes.

He couldn’t take Dean as deep as he could in another position but there was something so inexplicably thrilling to be trying something like this. He knew it wasn’t anything special and he was probably doing it wrong but it felt like something exciting and a little naughty even though for Dean it probably would never crack top ten in his best sexual experiences.

Probably trying to keep encouraging Cas, as he’d seemed to be doing more, Dean seemed to grit out, “Jesus, this is hot.”

He hummed his agreement around the solid piece in his mouth and hallowed his cheeks just a little further, his neck a little uncomfortable at the angle but not terribly.

Dean’s voice was rising in pitch, “Fuck. Are you touching yourself?”

Castiel hadn’t even thought about it until that very moment, his hands too interested in grabbing Dean’s ass, just because he could. Now though he realized just how hard and aching he was. He maneuvered one hand away from the globe of Dean’s cheek it was settled on and began raking his hand over his own dick feeling just how pent up he’d actually become. His hips were squirming on their own accord, searching for more friction, so Cas doubled his efforts with his hand.

He loved this. He loved the way Dean felt pressing in between his lips, sometimes a little unsteadily as his hips jerked and twitched.

“Shitshitshitshitshit.” Dean breathed in a rush. It was the erratic movements above him that had Castiel gearing up to swallow around his best friend but that moment never came. Quickly, right before he was about to shoot, Dean pulled back, letting his release fall over Cas’s lips and chin.

He felt Dean crawl off of him but kept his eyes closed as he continued trying to bring himself to the brink too. He was extremely aroused and with Dean’s come on his face Cas was certain he would follow any moment. He wasn’t quite there yet but he didn’t let up on the movement of his wrist, only stuttering a little when he felt warm puffs of breath in his ear.

“Come on, you’re so close. That’s it.”

Dean had moved to lay next to him, the solid line of his body pressing into Cas’s side.


“Keep going, don’t stop.”

Cas could feel Dean’s forehead against his temple as his friend whispered hotly in his ear.

He knew his moans were pathetic, and he felt like he was right on the brink but his body just wasn’t letting him go. He wanted so badly to be touched. So badly to feel the warmth of Dean’s skin against his own but knew the nose pressing against his cheekbone was the best he could get.

“You’re so close,” Dean spoke again and Cas could feel his rich voice down to the base of his spine. How could his friend affect him so much yet Cas still struggled to achieve his orgasm?

“I can’t…” he whined frustrated, wanting so badly to feel the satisfaction he knew was coming.

“You can. Don’t stop,” Dean encouraged, even as Cas squirmed next to him like a madman. “So fuckin’ hot. Come on.”

Cas whined a little, trying so hard to get himself all the way there. His toes were curling and he felt like he was going to lose his mind. He wanted it so badly.

Then it happened… a tentative touch to the flesh of his belly. Dean’s palm smoothed over him, and that did it. In an instant he was flying through his orgasm. Dean’s words were still whispering in his ear when Cas came back to himself. “There you go. So fuckin’ good.”

His breathing still came in pants and his thighs still twitched with the slowing movements of his hands until eventually Cas allowed his body to just relax into the bed.

“Don’t move. I’ll clean you up.” Dean declared before extracting himself from the bed. In a matter of minutes Castiel felt a washcloth being traced over the wet spots on his stomach and over his face to get any come off of him, his eyes still remaining closed. Even as Dean crawled back into the bed Cas couldn’t find the energy to be anything more than blissful.

“Come here.” He heard whispered at his side, and that’s when he finally let his eyes drift open, to see Dean shifting on the bed enough to pull Cas into a cuddle.

Castiel went willingly, resting his head on Dean chest and slinging his arm across his friend’s waist. He even felt bold enough to shift one of his legs over Dean’s, sinking into the other man’s embrace. It was indulgent and selfish but he relished in the moment, because Dean didn’t push him away and damnit it felt good. It felt right.

“You’re seriously fulfilling a bunch of fantasies I didn’t even know I had.”

Cas laughed against Dean’s chest. “I’m taking it that you enjoyed yourself?”

“Dude, is that even a question?”

“I’m glad.”

“Yeah, same.”

There was silence for a little while as they comfortably laid there. Cas could have fallen back asleep but his mind was filled with thoughts on just how perfect it felt to lay in Dean’s arms, he didn’t want the privilege to be taken away just by falling asleep. But what if he did fall asleep? Would Dean care so much? What if they both wore themselves out so much that they couldn’t help but pass out, wrapped up in each other? What if they fell asleep together after more intense sex… perhaps after intercourse?

Cas tried not to tremble at the thought but images of Dean’s body atop his, crushing him into the mattress after an intense orgasm. He wanted that feeling so bad. Enough to feel just slightly brave enough to broach the subject. He pulled back a little, satisfied when Dean’s arm didn’t leave its place on the small of his back.

“Can I ask you something?”


Despite his claim of bravery, Cas’s voice still shook a little. He couldn’t meet Dean’s eyes so he occupied himself with tracing a few freckles on Dean’s collarbone with the tip of his finger.

“I know I said… I know I said I just wanted to learn how to give hand jobs and blow jobs but…”

“But what?”

“What if… what if I wanted to learn how to do other things?”

“Like what?”

He looked up to meet his friend’s eyes and was comforted to see Dean’s face only show with patience and friendship, nothing in his eyes giving way that he suspected what Cas was about to say.

It took him a moment to collect his courage but he finally managed to whisper out, “Like… what if I wanted to try having intercourse?”

That’s when Dean’s face closed off.


Heart thumping, Cas pulled away from Dean’s arms and tugged the blanket from the end of the bed around himself. He felt vulnerable but he tried to act strong, wanting Dean to understand his side of things before his friend could outright reject him.

Dean must have sensed the shift in the conversation and pulled himself into an upright position still looking at Cas with a slightly terrified expression.

“Dean look, I know this is probably so weird for you, but there is no one else I’d want to ask this of.”

It was true. The thought of having intercourse with anyone besides Dean never really crossed his mind, not really. If he did imagine it, it was to some nameless, faceless blob and more in the sense of ‘what would it even be like?’ But when he thought of it practically and imagined how he’d ever want it to be if he could have real sex with someone, it had always been Dean he wanted to experience it with. Even before all of this.

Dean however, didn’t know that.

“That’s because you haven’t tried to use your new skills to try and meet anyone else,” he challenged but it made Cas a little frustrated.

“Dean! You said it yourself, you prefer a partner who is more experienced.”

“And now you’re experienced!” Dean declared. “Anyone would be willing to do you.”

“But what happens after we fool around like this and then they want to have sex with me? What happens when I don’t know what it will feel like or—or how much it might hurt? Or what if I don’t know how to keep them satisfied because I’m new to it all and don’t know any positions besides missionary? What happens then?”

There must have been something wild and desperate in his voice because Dean’s tense shoulders deflated and he looked too understanding for Cas’s liking.

“Cas, you just need to meet the right person. They won’t care if you’re new to all of this. Look at how fun it’s been exploring the things we have? Imagine doing that with someone you’re really with. There’s nothing to be scared of if you meet someone you really like and wait to be sexual with them.”

“I don’t want to wait, Dean. I want to experience this side of myself. I want to have fun. I want to not be worried that someone is going to be dissatisfied with my performance when we are together. Isn’t it more logical to do this with someone I trust, my best friend, so I can know what I’m doing wrong and not be embarrassed when I’m with someone else?”

“Cas, you should want to be with someone you care about, especially for your first time.”

“It would be with someone I care about; it’d be with you.”

Dean looked a bit taken back by those words and even Cas wondered if the words revealed too much.

“That’s different,” Dean croaked.

“You care about me too, don’t you? You’re my best friend and we work well together. What’s wrong with trying a little more when we’ve come this far?”


He felt like he was internally panicking and couldn’t help but cringe at the pitch his voice had suddenly taken. But what was he doing? Dean was clearly uninterested and Cas couldn’t beg him to do this out of pity. No meant no.

Who cared that he wanted to have this experience with Dean? It wasn’t like if they did have intercourse that Cas would somehow magically get to keep doing it with Dean forever. Eventually their arrangement would end and Cas would have to find other partners to do it with.

It sucked because he was comfortable with Dean and wanted this with him badly, but it was stupid of him to think he could have this. Maybe he should go try and find someone else?

“No, I’m sorry,” he said, cutting Dean off from what he was going to say. “I shouldn’t push. You’re right. I can’t ask that of you. Maybe I should try and find someone else.” He didn’t like the way those words felt coming out of his mouth but what more could he do? “Would you be able to help me with finding someone?”

There was an intense silence as Dean just looked Cas over, almost trying to read into Cas’s mind and figure him out. Cas felt his heart beating a tattoo into his ribs, wondering what the hell Dean was going to say. His friend seemed off but Cas couldn’t tell why. Dean didn’t seem mad but he certainly didn’t seem happy.

“I’m sorry,” Cas added, knowing he’d probably messed up more than he realized, especially if Dean didn’t even want to help him find another partner someday. He moved to get off the bed but Dean’s words stopped him.

“We can try to do… more.”


Cas couldn’t believe his ears. Was Dean really agreeing to—

“But I’m not having sex with you,” Dean cut in to his thoughts. “We aren’t going to cross that line.”

He was stuck in a mixture between relieved and disappointed and didn’t know what he was supposed to say. He’d asked if they could start having intercourse and Dean was saying no but he was telling him they could do more? What more could they do if they didn’t go all the way?

“Then how?”

It looked like even Dean wasn’t certain but then his friend was saying, “Toys—we’ll start experimenting with toys or something. It will be almost like the same thing.”


“That’s my offer.”

Cas let out a huff of frustration. He’d known Dean would try and talk him out of their arrangement going further. He’d known that Dean was only doing it to look out for him and ensure that Cas didn’t regret his choice but Castiel couldn’t help but feel a bit… rejected. Did Dean just not want to go further with him?

Obviously. What the hell was Cas thinking? He was a guy. No way was Dean sexually attracted to him. He probably thought Cas was pathetic, practically begging for Dean to fuck him. He was such an idiot. Why would he ever think that Dean would ever want to have sex with him?

Dean had signed up for blowjobs, nothing more. At least he was giving Cas a little mercy and letting them explore just a little bit more… whatever the hell that meant.

It had to be good enough for now.

“Okay.” Cas agreed, trying to plaster on a convincing smile.

Chapter Text

“Why are people bothering to even go back home for break? I mean can it even be called break? How can the school count the weekend as part of the break? It’s a three-day weekend, not a break.”

Dean looked out the window scornfully at all the kids with duffels over their shoulder, piling into cars and driving off to wherever the hell they went over break. For all his ranting and raving he was a little jealous of their ability to just return back home whenever they wanted.

He knew Bobby and Jody were doing okay money-wise but he couldn’t bring himself to ask for a plane ticket no matter how bad he was missing them. They always told him that he could come home any time but he also knew they had Sammy they were still looking after. With his brother in the midst of applying for colleges and scholarships and eventually needing a reliable car to get him around whatever town he was going to go to for school, Dean just couldn’t let himself take any money that should be going to Sammy. Plus, it’d become a thing that he and Cas would sit out the shorter holidays and wait until the longer ones to go back home. Cas’s dad lived in L.A. and Dean’s family was in Sioux Falls and even though the drive from Las Vegas to L.A. wasn’t a bad one and Cas could even fly there for fairly cheap, he seemed to be willing to hang out with Dean’s sorry ass.

“Veteran’s day is in a few weeks and we have Thanksgiving break a few weeks after that,” Cas responded easily, unbothered by the traveling students outside.

“Hooray, a four-day weekend this time,” Dean exclaimed sarcastically, waving his hands in the air in mock excitement. When he already had Fridays off and therefore had three-day weekends every week, an extra Thursday didn’t really do much for him.

“Five if you have a professor who has a flight to catch that Wednesday,” Cas added nonchalantly.

“At least we don’t have classes,” Dean declared, finally pulling himself away from the window. “So what’s our game plan this time?”

Cas had somehow managed to take over most of the futon so Dean playfully shoved his friend’s feet out of the way as he planted himself on the seat. The TV was on and Cas was entranced as he flipped through the options to stream.

“Can we watch The Handmaid’s Tale?” Cas asked suddenly, the poster for the series up on the screen.

“Seriously?” Dean exclaimed. It wasn’t exactly in Dean’s top five of ways he wanted to spend the weekend alone with Cas.

“Hannah recommended it. She said it’s really good.”

Dean stared at his friend for a little waiting to see if Cas was joking or not but the open and waiting expression on Cas’s face had Dean rolling his eyes and agreeing to Cas’s wishes.

“Kay, fine. But then we watch all Star Wars.”

Cas shrugged, “Obviously, that’s expected.”

“Even the new ones.”

“Dean that’ll take three days!” Cas protested, looking a little put out at the prospect. “How can we watch the show and all the movies?”

Dean really was just fucking with Cas, he knew his friend didn’t love Star Wars to the same degree Dean did, plus Dean didn’t actually mind binge watching another TV series with his best friend but he rolled with the joke anyway. “Who needs sleep?”

Cas still seemed unsure of Dean was joking or not but slumming it around the dorm for three days seemed to be an okay idea for him since he bargained, “You’re making the popcorn and buying the candy.”

“Puts you on beer duty,” Dean said with a grin.

Cas slumped further into the futon and huffed, “Fine.”

Dean would never admit how endearing he found grumpy Cas to be but damnit the guy was like a sulking cat when he didn’t get his way. Dean could just tell him he was fucking with him but where was the fun in that?

He patted Cas’s leg and asked, “What do you want for dinner, grump?”

His friend thought about it for far too long before stretching and yawning. It was unfair how sweet he looked as he turned to Dean and asked, “Can you make burgers?”

Looking at that face, Dean wanted to say yes and give Cas anything and everything he wanted but he knew better.

“I’m not going in the kitchen.”

“Come on, it’s break. No one will be cooking in there,” Cas protested, nearly pouting. Dean had to laugh at his friend because that guy loved burgers more than anyone Dean had ever known but cooking in their dorm kitchen?

“Hard no. Last time I was in there I ended up giving half my food away and you had to eat cold lasagna.”

He thought Cas would laugh at the memory too but instead the other man’s face fell a little as he turned back to the TV where the show was waiting to be played.

“Fine,” Cas huffed, sounding very clearly not fine.

Something was up, and had been for a few days and Dean knew it was his fault.

Ever since they’d talked about going all the way or not, Dean noticed that Cas seemed pretty bummed. He wasn’t an idiot so he knew he made Cas feel rejected, he just didn’t know how to tell his friend that he wasn’t rejecting him.

He knew it was supposed to be the “smarter” choice, saying no to having sex with Cas, but he wasn’t going to lie to himself and say he was happy with having to say it. What would have actually been the smartest choice would have been ending it altogether, telling Cas that he really was going to be okay going out and finding someone else but the thought—

It still twisted in his gut as he played back Cas asking him for help finding someone. Why did it make him want to break something even just thinking about Cas getting help from someone else?

He was an idiot, a selfish idiot, who couldn’t stand the thought of not getting to do anything with Cas anymore. He wanted to tell Cas that he’d have sex with him in a heartbeat if he knew for sure it wouldn’t blow up in their faces but he was trying to be better than that.

He still hated seeing Cas look so bummed.

“I’ll order sushi for you?” He ended up asking, though he was ready to go out and buy everything to make burgers if that was really what Cas wanted. He’d even brave the damn communal kitchen and the dozen or so students who would undoubtedly try and mooch some of the food. Luckily Cas’s face lit up at the sound of sushi.

“Spicy tuna rolls?”

“You got it.” Dean got off the couch to grab his phone that was plugged in on his bed. As he was finding the number for the restaurant they liked best, Cas got up and crossed the room to go to the restroom. He patted Dean on the arm as he walked by.

“Thank you, Dean.”

“No problem.”

He resisted the urge to reach out and pull Cas towards him and wrap him up in a hug. It’s not that they never hugged but not in the way Dean wanted. He wanted to stand there and keep Cas close, maybe breath in the scent of his friend in the way he always tried to hide when they cuddled. A simple ‘bro-hug’ wasn’t going to do it.

This whole situation was starting to mess with his mind a little bit. One minute all he wanted to do was hold Cas and touch him and just be with him and the next minute he couldn’t stop thinking about getting his friend naked and doing any and all things possible with him. And now he had the new struggle of figuring out how to make Cas satisfied with going further without actually having sex.

It was a sham and Dean knew it, he just wondered if Cas knew it too. What could Dean do for Cas with toys that Cas couldn’t do for himself?

He wasn’t sure if he was ready to give Cas a blowjob or even jerk him off, but he figured since Cas hadn’t asked, that maybe it was something the other guy wasn’t interested from him? If Cas ever did bring it up, Dean would give it a try, not that he thought he’d be good at it or even like doing it, but he’d at least try. It just didn’t seem like Cas’s mind was even there?

But he’d promised his friend they’d do more, so Dean still had to figure out what more meant. Cas seemed to really want to go all the way and Dean knew that meant they’d be finding out what felt nice when it went—

He didn’t want to mess this up and he didn’t want to make it suck either. Cas deserved something good, really good, and it was a shame all he had was Dean around to help him.

He knew the smart thing to do right now would be to have a good long chat and maybe set some more boundaries and rules for what they were about to try but Dean was pretty sure everything would work out. He’d just keep following Cas’s lead.

Chapter Text

This was new territory for them and Cas was a little out of his element. He was starting to learn that the hardest part about entering the world of sexuality was actually asking for what he wanted. He knew Dean was open to trying things out with him but the words still stayed at the tip of his tongue, especially since he and Dean had talked about doing more.

He knew eventually he’d need to build up the courage to ask but a huge part of him was just hoping Dean would take the lead. It was his own insecurities making him think that if Dean was the one to bring it up again, then maybe he wouldn’t lose interest as quickly. Castiel hated thinking about it but he feared that if he was the one receiving the pleasure, even if from some toys, Dean wouldn’t care to do this with him anymore. Cas had promised Dean that he wouldn’t have to do anything, that this arrangement would be solely based on Cas giving the pleasure… he didn’t want Dean to hate him for changing the dynamic.

Castiel knew he was fully capable of using toys on himself. He knew he didn’t need Dean to assist him with using them but…. He felt a thrill every time he thought about Dean using them on him. About Dean maybe touching him more than just on his thighs or his chest like Dean’s hands sometimes fell.

What would it feel like to have Dean’s fingers in him, opening him up so that he became loose enough to take a dildo? What would it feel like if Dean’s hands wandered a little too much and his knuckles brushed against Cas’s shaft, even if just accidently? What would it feel like to have Dean pressed up against him, pushing a toy in and out of Cas’s channel? Despite basically being constantly horny, he knew he wasn’t able to outright ask for any of that, but he did know how to entice his friend into at least being naked with him.

He showered quickly and thoroughly as he’d taken to recently (just in case), forgoing his shirt but settling into his lounge pants. Maybe it was the growing need inside of him but he marched with a purpose over to the couch and plopped down beside Dean.

“Take them off?” he requested, tugging at the edge of Dean’s pants which quickly vanished right after.

Instead of moving to the floor, Cas shifted to lie on his stomach across the unoccupied space of the couch and had Dean’s dick bobbing in and out of his mouth in no time. He wasn’t sure if he was getting any better at this but he did know he was having more and more fun each time he did. That had to mean he was pretty okay, right? It’s just that he really liked hearing how Dean sounded when something felt nice, and he wanted to do anything he could to keep hearing that. He figured that’s why people did this in the first place.

He always assumed that it would be a dull task to take someone in his mouth and spend who knows how long trying to get them off. He’d assumed that there’d be no satisfaction for himself but if he cared enough about the person he was with he’d endure it anyway. But that’s not at all how it felt at all. It thrilled him to not be bad at this. It made his mind a little hazy every time he discovered new ways to take Dean’s length and be rewarded with a moan. And the way Dean would mutter encouragement and practically vibrate from his moans and groans… it was dizzying.

With Cas on his belly against the couch, sucking Dean, the other man’s arm was left to rest steadily on his back. There was something so gentle about how Dean would rub Cas’s back like he didn’t know what to do with his hand most of the time but every so often he’d trail it up to Cas’s hair and tug a little, eliciting a small whine from Cas’s throat, making them both laugh a little.

After a little bit of time, instead of Dean’s hand just resting on his back it started trailing up and down Cas’s naked spine, a sensation that felt too good to be real. Dean’s hands were warm and broad and left goosebumps on Cas’s skin as he trailed them up and down. Cas’s attention was too preoccupied with making Dean feel good that he didn’t notice as Dean’s movements grew bolder and his fingers started inching closer and closer to the waistband of Cas’s pants.

Two… three… four times Dean’s fingers dipped just under the waistband before retreating away, back up Cas’s spine into his hair. He wasn’t sure if Dean was actually considering touching Cas’s ass and didn’t want to pressure Dean into touching him anywhere he didn’t want to, but Cas still craved it all the same.

He felt a little sloppier as his mind was now swirling with fantasies of Dean touching him there, so when Dean’s fingers slipped under the band of his pants and made their way towards his crack, Cas had to pull off to let out a whimper. He panted as he allowed himself to just feel Dean’s fingers making their way to where he’d been dying to be touched. Right when he thought Dean was finally going to do it, the fingers moved to the side, gripping the roundness of one of his ass cheeks instead.

Cas’s forehead dropped to Dean’s hipbone.

“Don’t stop,” he heard Dean breathe from above him.

Looking up, Cas wound up entranced by lust filled eyes. “I’ll keep going if you want but I want you to keep… uhm, keep doing what you were doing too,” Dean explained.

Dean’s palm was still flush against his ass and Cas could only imagine how it’d feel if Dean kept exploring with that hand. Needing Dean to touch him in a way he’d never been touched before, Cas nodded and brought his mouth back down to engulf Dean’s cock more enthusiastic than ever.

As promised, Dean’s fingers started their decent back down the hills of his ass, trailing every which way but not quite reaching the proper destination.

He couldn’t have been more needy if he tried, Cas thought, as he canted his hips back, trying to press into the touch that kept evading his desires.

He didn’t have time to worry if Dean was second guessing himself because before he knew it, the pad of Dean’s finger trailed lightly over his hole, making Cas keen from the feel of it.

He’d touched himself there before, a few times, most recently in the shower but feeling someone else’s touch, Dean’s touch there was completely different. It was unpredictable and more hesitant than any way he’d touched himself before but Cas figured Dean was still deciding if he was okay with it. Eventually Dean’s fingers stopped merely trailing over Cas’s hole, before finally starting to circle around it, pressing against the rim with a gentle pressure.

Cas’s own cock was rock hard now. He was in no way ashamed of now rutting against the couch, wantonly moaning around the dick in his mouth. He doubled his efforts then, using his hand to massage Dean’s balls, while bobbing his head quickly, trying and failing to not think about the fact that Dean had his fingers against his rim.

Unexpectedly, Dean’s hand pulled away from him and for a moment Castiel thought his friend had changed his mind, but before he could pull off of Dean’s cock, the hand was back, and those fingers now wetter than they had been. He suspected from Dean’s own spit. The pressure was back too, more intent than it had been before. Cas’s legs instinctively spread as he waited for what his body seemed to be burning for. He tried to stay focused on sucking Dean off but his mind couldn’t stop drifting to the feeling of Dean pressing against him.

And then it was there, the feeling he’d been dying for; Dean’s finger pushing through the ring of muscle, oh so slowly. He couldn’t stop himself… he let out the most pathetic whine around Dean’s length and then suddenly Dean was coming down his throat and Cas was choking for the first time in weeks. Cas hadn’t even noticed how close Dean had been.

Everything seemed to happen very quickly as he tried to get his coughing under control. With a few mumbled directions, Dean had Cas turn over onto his back and then Cas’s pants were off and Dean was sitting on the other side of the couch with his fingers circling Cas’s entrance.

Cas could only stare at his friend who looked just as overwhelmed as Castiel felt. He thought about telling Dean that it was okay if he didn’t want to keep going—that he’d understand if Dean wanted Cas to finish himself off because his friend had already achieved orgasm, but Dean moved towards the ottoman, fumbling inside a little until he pulled out a travel size bottle of clear liquid.

“I uh—I got this the other day—just… uh, just in case,” Dean explained, his cheeks tinged red from his orgasm.

Cas didn’t really know what to say, so he nodded instead and waited as Dean clicked open the cap and poured some of the contents onto his fingers. Instinctively he let his knees drop a little further to the sides as Dean’s hand came back.

It felt a lot more intense being able to stare up at Dean like this and watch his friend’s features as he brought his finger back to Cas’s entrance and pushed in. He really liked having Dean touching him and that feeling just kept growing as Dean moved his finger in and out for a little before slowing to a stop.

“Hey, touch yourself,” Dean commanded gently, voice sounding deeper than Cas had ever heard it before. Cas’s eyes flew opened, though he didn’t remember ever shutting them. He watched Dean staring down at where he was fingering Cas, and something about the look on his friend’s face made his own need feel ten times hotter.

He didn’t rush himself as he wrapped his hands around his cock, just stroked it enough to keep his dick interested but not enough to distract him from the feel of Dean now pressing two slick fingers inside of him. But he wasn’t used to this feeling and he knew he was approaching his orgasm faster than he ever had before so when the slight burn of a third finger came, Cas knew he was done for. It took only four quick strokes before a silent scream ripped the air from his lungs and he was coming all over his chest and stomach.

If fingers felt that good, he couldn’t imagine what it’d feel like to have all of Dean inside him but for now he’d take what he could get because—

“Holy fuck.” Dean spoke, completing what Cas was thinking. His friend’s fingers had just now stopped moving inside of him and slowly pulled out making Cas shiver.

His arm flew over his face as he tried to catch his breath. He’d never known something like that could feel so fucking good. He wanted a repeat of that performance pronto. His mind was complete mush.

“You okay?” He heard Dean ask worriedly but Cas could barely even complete a nod.

“Mhm,” he tried to ensure, a grin pushing at his cheeks.

“Your brain a little fried?”


Dean laughed a little. “Can you form real words?” Cas pulled his arm away from his face and finally looked over to Dean. The look Dean was giving him was a bit unreadable at the moment but Cas smiled softly at his green-eyed friend anyway.


“Was that—did you like that?”

Cas couldn’t help but laugh and roll his eyes at the other boy. “Maybe a little.”


He hadn’t noticed that Dean’s hand was soothing up and down his thigh. The touch felt good, calming. He let himself be comforted by his friend’s hand just a little longer before he found his voice again.

“Did uh—did you… were you okay with that?”

“Yeah.” Dean answered instantaneously. Cas watched as his friend’s eyes roamed down his body before coming back up to lock with Cas’s. “It was different but… honestly? You’re—you’re uh… you’re like, really fucking tight.”


“For what?” Dean’s confusion was evident but Cas himself didn’t know why he felt like he needed to apologize. Was being too tight a bad thing? Did he like… did he squish Dean’s fingers?

“I don’t know?”

Dean’s look was still that of confusion but he shook it from his features a moment later and smiled down at Cas again.

“I’m gonna clean you up. Stay here.”


Cas felt a little like he could take a four-hour nap and he didn’t want to fight it. He let Dean run a cool cloth over him and between his legs before he felt his friend nudging him over on the futon.

“Okay, lazy, move over.”

Once Cas was settled, Dean pulled him into his arms. It was admittedly a small fit on the futon and they probably should have laid the couch into a bed but Cas was not complaining about being pressed up close to his favorite person. Too foggy minded to really think straight Cas nuzzled his nose into the crook of Dean’s neck and found his eyes start feeling very heavy.

If he happened to take a two-hour nap on his best friend’s chest… well that was nobody’s business but his own.

For the record: right before he drifted off to sleep, his heart told him to be careful.

Chapter Text

He was mostly staring at his computer screen wondering when the surge of motivation would hit him hard enough to finish the conclusion to his ‘History of The Beatles’ paper he was writing for one of his electives. Generally, he was pretty eager to hash out work for this course but his mind felt a little… off. No matter how much he tried to focus he kept coming back to the same thoughts and he was eager to ignore them just a little bit longer. Thankfully his buzzing phone called for his immediate attention.

He picked up on the first buzz and felt his face light up when he heard his adoptive father’s voice on the other line.

“Hey kid.”

“Hey Pops,” Dean greeted back, already feeling ten times better just knowing Bobby was on the other end of the phone.

“Haven’t heard from you in a little bit, you doing good? School okay?”

Dean moved away from his desk and laptop and clambered onto his bed, settling in for a chat.

“Yeah, I’m ready for break already though.”

His dad harrumphed on the other end. “Classes getting harder?”

He’d never admit it but he loved the concern he always heard in Bobby or Jody’s voices when they called him during the week or the way the sounded genuinely interested in listening to anything that bothered him. Really, he just loved remembering sometimes that he had people somewhere that missed him.

Everything he had and everything he was, he owed to those two. Without a doubt, his life could have been so much different—and so much darker—if it weren’t for the two people he was lucky enough to call his parents.

He vaguely remembers the shit his biological father put him through. He sometimes finds his mind flashing back to hazy memories of wrapping his baby brother in a blanket and holding him tightly at the bottom of the closest to sleep that night if his dad smelled funny again. He knows there was abuse. He knows that John hit him and yelled a lot and left a few circular shaped scars on the back of his left shoulder but his memory isn’t all there for most of it—something he’s both thankful for yet often frustrated about.

He wishes he could remember the first few months with Jody but those memories are mostly lost to him as well, only vague flashes of moments, but most of what he knows is based on what his mom told him. When he asked her about it, years ago, she said he’d been timid and refused to let anyone hold Sam or feed him for nearly two whole months. She said that it even took Dean close to a year to really warm up to her and start accepting hugs. And it wasn’t until well over a year of living with Jody that Dean seemed accepting enough to be around Bobby more often.

Dean does, however, remember how happy he’d been when Bobby did come to live with them. Bobby had set up the living room with Batman decorations and the two of them had a movie marathon watching all the cartoon Batman movies that Bobby could get his hands on. Dean even remembers that it was raining and Bobby let Dean go jump in the puddles with him. It was one of those nights that Dean assumed would be played on a reel if he ever made it to heaven or whatever. He remembers it as the first night that he thought that maybe he got to have a good family like all the other kids at his school and on the TV too.

Jody and Bobby ended up being the best thing to ever happen to him and Sam, and aside from a few dozen nightmares that still crept in, or a handful of childhood depression related issues, Dean had turned out pretty okay. He owed a lot to them and he didn’t know if he’d ever be able to show them just how grateful he was for everything they’d done.

So, where some kids got annoyed with their parents calling all the time, Dean loved it and he’d humor his dad talking about school any day.

“No, the classes aren’t getting harder but the professors are getting pettier. I mean I have this one who keeps giving us these damn essays with weird length requirements. The last essay had to be six and a half pages long and this one has to be eleven. Eleven, dad! It’s stupid.”

The sound of Bobby laughing on the other end of the line was enough to make Dean crack up too. The old man sounded like he was smiling when he asked, “But you’re still doing okay in your classes overall?”

If it weren’t for Bobby working with him when all Dean’s teachers tried to write off his lack of attention as ‘lashing out,’ Dean’s pretty sure he wouldn’t have made it through high school let alone gotten into college.

Bobby stuck by him, no matter how much Dean had pushed back. He found ways to explain things to Dean’s racing mind and made learning not so grueling. Dean knew that even now, if something was too difficult for him, Bobby was just one phone call away and would stay on the phone with Dean for hours until it started making sense.

“Yeah, I’m doing fine in them,” Dean confirmed. “I have a few friends in most of them so they’ll study with me and we work on a few papers together here and there.”

“And how’s everything else? Car okay? You got enough money for gas and food?”

“Yeah I’m all good there.”

“Glad to hear it.”

“Is everything good at home? Is Sammy good,” Dean asked, realizing just then, that it’d been a while since he’d called home. He suddenly felt like a jerk. He’d been missing his family so much yet had been too distracted with everything with Cas to even call. He hated not being able to drive home and see them whenever he wanted to.

“Yup, he’s working on scholarship applications and there’s a few more schools he’s been looking into.”

“His grades holding up?”

“You know it.” Bobby said with a snort, as if Sam could ever get anything less than an A plus. “Anything new with you kid?”

Like every time Bobby asked this over one of their phone calls, Dean had to forcefully shove any image of naked-Castiel from his mind.

“Uh. Not really,” he answered lamely.

“Any girlfriends I should know about?” Bobby teased, as usual. It was a dad thing, Dean knew, yet it made Dean stammer anyway.

“Nah. No. No, I don’t have time for that.”

He heard a low laugh on the receiver. “Oh really?”

“Yeah. No girls. I’m not dating.”

There was a pause on Bobby’s end, like he was waiting for Dean to say something more but eventually the silence ended, “Good. Keep it that way, idjit. Anyway, how’s Cas doing?”

“Wh-what?” Dean nearly choked, feeling like Bobby somehow knew but there was know way he’d know. He tried to keep his cool. “Oh Cas? Yeah, he’s good. Cas’s real good.”

Great job Winchester, real smooth, he thought, smacking himself in the head. Apparently, Bobby was oblivious since he kept on talking.

“Jody’s been wondering if he’s going to come for winter break this year.”

The momentary worry that Bobby somehow knew that he and Cas were having secret rendezvous in their dorm, immediately diminished hearing his dad ask that. He felt a little silly thinking that his parents would somehow just intuitively know that he and Cas were hooking up in secret, it made infinitely more sense that they’d want to know if his best friend was joining them for the holidays. But that left Dean wondering if Cas was coming home with him. The previous year had been the first year Cas had come with him but their first two years they’d spent apart.

Of course Dean wanted Cas to if his friend was interested. He loved having Cas around on breaks. The guy was his best friend and he missed him when they were apart but… with the shift in their dynamic? Would it be awkward if they were around Dean’s family?

Would Sam, Bobby, and Jody figure out what they’d been up to?

Shit… he’d need to talk to Cas about that.

“We haven’t talked about that yet actually,” Dean answered honestly.

“Let him know he’s always welcome here.”

“I will.” He smiled knowing that his family really did love Cas, but he couldn’t help but wonder if they’d still feel the same if they found out what he and Dean had been up to?

He couldn’t see his family being against him being with a guy but what he and Cas were doing? This hooking up, no strings attached, friends with benefits type deal didn’t seem like something his parents would understand. He had a feeling they’d be disappointed in him for not treating Cas the way Cas should be treated. Hell, he was mad at himself for it too.

Before he could spiral a little more into his thoughts, Bobby kept talking, “Oh. That reminds me. You need to call your brother. He still wants to come out and see you and Cas but he wants to do it when schools in session. He’s been bugging if we can send him out right before you go on winter break. Maybe even Thanksgiving break.”

Dean perked up at the mention of his brother coming to visit.

“Alright, I’ll call him now.”

“Good. Miss ya’ you idjit.”

“I miss you too.”

He hung up with Bobby but wasted no time before he found his brother’s name in his contacts and pressed call.


“Hey Sammy.”

“What’s up?”

“Dad said you might want to come out for a little?”

“Oh! Yeah!” It was the genuine excitement in Sam’s voice that had Dean smiling over the phone. “I’m thinking about it. Him and mom said they’d be cool flying me out if I could stay with you. I don’t know when’s a good time for you though.”

Out of habit, Dean peered over at the calendar on the opposite wall. “I have most Friday’s off but I don’t want you to miss any school. So probably on one of the breaks would be best.”

“I kind of want to tour it when school’s in, though,” Sam’s voice had just enough disappointment in it to make Dean want to fold like a card table but the thought of having to still go to classes while his brother was visiting didn’t sound as much fun as getting to hang out with Sam as much as he could.

“I don’t know if that’s really gonna work for me though, dude. I won’t really be able to give you any tours if I’m in class.”

“Would Cas be able to?”

“Maybe? He has mostly afternoon classes so he could probably take you in the morning.”

“I’ll text you more and figure it out okay?”

“Yeah!” Dean actually felt giddy at the thought of Sammy coming out and visiting him at UNLV. He knew logically the kid probably wouldn’t end up going to his school since he’d always seemed pretty set on living in California or any state with a beach, but Dean still wanted to have the chance to convince his brother to be a little closer to him.

Damn, he missed having his brother around all the time. As much as they’d pick on each other and as much as Sam could be a snot-nosed brat at times, he was Dean’s closest friend growing up.

“How’s everything back home?” Dean asked, not wanting to get off the phone just yet.

“Same as normal. Nothing really special going on.” Sam shrugged off like a typical teenager. Dean could hear the video games through the receiver and knew his brother was only half listening to him.

“Okay, well I’ll let you get back to your eventful life.”

“I miss you.”

A surge of emotion hit him and Dean tried not to let himself get misty eyed. “Miss you too, kid. Text me okay?”

After hanging up the phone with his brother, Dean had a new sense of energy about him and managed to bang out his essay in record time. He even got a head start on some proofs he had for one of his engineering courses. Needless to say, he was in a good mood when Cas came walking in the door and dumped his bags.

“Heya, Cas! Day okay?”

“It was.” There was a smile in Cas’s voice. “You seem happy. I take it your day went well also?”

“I called Sammy earlier and he said he wants to try and find a time to come out and see the campus.”

Cas looked genuinely pleased by the news. “That’s exciting. It’s been a while.”

“He wants either you or me to give him some tours around campus. I told him you’d probably be up for that.”

Dean watched unabashedly as Cas stripped out of his school clothes and into a pair of pajama bottoms. He wasn’t sure if getting to watch his friend half naked was really a part of their deal but he really couldn’t help himself. Cas was… fuck, Cas was hot okay? It didn’t take anything more than a pair of eyes to see that even though Cas was still filling out and was more on the lanky side, that his lean muscle was getting a little bulkier every year and he was starting to get kinda… ripped. He was a hot guy. It wasn’t like Dean was the only one who noticed that fact about him. Other people had eyes too.

His heart rate picked up a little watching the muscles of Cas’s back shift as he pulled up his pants and tied them off. Warmth started to fill his belly just thinking about getting Cas all the way out of his pajamas—why wear them around anymore anyway? It’d be so much easier if they both just came home and were naked all the time, right?

“Of course I’ll take him,” Cas declared, pulling Dean’s mind out of the gutter that it’d been so perpetually stuck in lately he was probably about to find Pennywise. What was Cas doing to him?

“I’ll let him know,” Dean said with an awkward cough, trying to casually readjust how he was sitting on the couch.

“Sounds wonderful.”

Cas plopped into his beanbag and wrapped his blanket around himself before flicking the TV on and getting the next episode of Dr. Sexy up. “So, what’s supposed to happen this week with Dr. Piccolo? Did she survive the bomb in that man’s rectum?”

Dean tried to ignore the little sting of ’rejected’ he felt when Cas didn’t choose to sit next to him on the couch, but… it wasn’t like he offered either. Besides, it wasn’t like they cuddled except for when they engaged in their “learning” and he sure as hell did not expect Cas to want to touch him every single day. So it was definitely normal for Cas to not sit next to him if he didn’t want to “learn” with Dean today. It was fine. Really.


What was wrong with him? He was starting to act like such a melodramatic teenaged girl on all those TV shows.

He was screwed.

Friday October 27, 2017

He’d just been three fingers deep in his best friend’s ass and now he was holding him against his chest like it was normal.

And okay, maybe it was their normal but it was starting to make Dean wonder if there were any other friends out there who finger fucked their best friends after getting an extremely sloppy blowjob from said friend.

Probably somewhere in the world, right?

He just didn’t know how much longer Cas would want to do this with him before he started asking for more again and Dean honestly didn’t think his resolve was strong enough to withstand Cas asking for sex again. He knew just one look into those pleading blue eyes and Dean would probably crumble. He was barely keeping his resolve together by a tiny thread because when Cas asked him if they could have sex, Dean wanted more than anything to say yes.

But now? Now that he’d felt how fucking velvety and warm Cas felt around his fingers he couldn’t help but wonder what it’d feel like to have Cas’s body underneath his—to have his cock inside that tight—

He needed to stop letting his mind go there because he couldn’t do that. He was already crossing so many lines to begin with but he couldn’t do the most inherently wrong thing he could think of. He could not steal away Cas’s last bit of innocence just because his libido was raging all the time now, no matter how much he wanted to.

He was the worst kind of asshole imaginable. But he’d never hurt Cas. He would not do that to his friend.

But he could give Cas what he wanted in their own ways and he wanted to do as much as he could for Cas because seeing his friend come? It was like watching someone completely crumble into dust under his fingertips after dynamite went off inside of him.

Dean didn’t think he was bad in bed, in fact he always thought he was pretty decent but… Dean had seen nothing like this from anyone. Yeah, maybe it was different because Cas was a dude and maybe dudes got off a little more explosively than girls did, but even Dean was coming harder than he ever had, even with the bendiest of chick’s he’d fooled around with.

It was different with Cas and Dean didn’t know (or didn’t want to know) why.

Still, he wanted Cas to feel amazing. He wanted to draw as much pleasure out of his friend as he could so that Cas would know how good sex and fooling around could feel. He wanted Cas to be confident in himself so if he ever were in relationships in the future, he’d have a frame of reference. Dean wanted Cas to know what to ask for to give himself the best feelings and the best time.

Dean was still a little horny and apparently so was Cas because even though they were technically in the cuddling stage, Dean still had one of his fingers lazily pressing in and out of Cas’s loosened hole. He couldn’t help it, okay? He liked the little mewls that were escaping Cas’s lips.

“Dean,“ Cas breathed hotly against his collar, making Dean smirk a little. He loved that he affected his friend this bad.

“Yeah?” His question was innocent but the deep press of his finger was not


“What do you need?”

Cas’s leg that had been thrown over Dean’s own shifted just enough to align Cas’s dick against Dean’s hip. His friend seemed almost unaware of the fact that he was grinding into him and Dean didn’t care in the slightest. He just pressed another finger back into Cas’s ass, pumping with more of a purpose now.

Cas breathed into his neck, mumbling incoherent words and making pitiful sounds that only increased the speed that Dean thrusted his fingers. His friend’s hips started moving with more of a purpose.

Dean had gone insane. Each and every day he kept crossing more and more lines but fuck if he cared. Not when Cas’s dick was literally four inches away from his and the walls of Cas’s ass were fluttering around his fingers. “Oh fuck. That’s it. You’re gonna come again aren’t you?”

“Hng—yeah. Oh! Dean.”

Dean’s eyes rolled into the back of his head as he groaned. How the fuck was this so hot? He’d literally just gotten off fifteen minutes ago.

“Wanna come with you.” He declared.

And that’s when Cas got with the program, reaching down to tug on Dean’s cock as he continued thrusting against Dean’s hip.

They were so close like this, so much skin was touching and it was making Dean lose his fucking mind. All he wanted at that moment was to pin Cas down and wrap his friend’s legs around him. He wanted to press into the tight warmth that was currently encircling his fingers. He wanted to fuck his friend hard and deep and watch as Cas fell apart beneath him. He wanted to hear Cas rasping his name and feel him clawing at his back.

Holy fuck he wanted to fuck his best friend.

He wanted it so bad.

“Fuck, fuck, fuck, fuck, fuck.” Dean cursed as his second orgasm of the night hit him like a train. It wasn’t even a beat later that Cas followed behind him.

“Dean, I—Dean. Ugnh!” Cas’s moans were muffled by the crease of Dean’s neck.

It took a few moments for both of their spasming limbs to start to calm down. And even though no part of him wanted to stop touching Cas he finally pulled his fingers away, wiped them on the sheet, and started gently rubbing Cas’s back as he slowly stopped shaking.

Dean couldn’t move. He definitely had Cas’s come on his hip and his own on his stomach and they were definitely chilled from their sweat damp bodies and the AC so they were probably not in the most comfortable position but his limbs felt like lead and Cas felt like dead weight at his side.

“You okay?”

“Mhm.” Cas mumbled into his neck. A moment later Dean felt his friend shiver at his side.



Dean kicked his feet, trying to get the sheets untangled from the bottom. Eventually he got enough up to tug at the thin twin sized material that hardly did anything to warm them up, but it was better than nothing for the time being.

He thinks they dozed for maybe twenty minutes or so but eventually he knew both of them were awake yet neither of them were pulling away from one another.

It scared him how comfortable this was. Shouldn’t it feel weird to have his best guy friend lying next to him naked? Shouldn’t it feel weird to feel a soft cock against his hip and the scruff on his friend’s jaw against his shoulder? Why did it feel like everything Dean couldn’t put words to? Why did this feel right?

Dean could feel his heart and his mind going at it, full battle axes and armor and everything, lashing out against each other trying to prove that one was correct. Knowing the internal battle he was facing Dean still felt inclined to listen to his mind; Cas was his best friend, he was only here to help Cas out, there was no way anything would come out of this arrangement because all it was, was an arrangement. Cas was using him to get experience to use with other future partners. It was not to use with Dean in some kind of relationship.

Dean was the one to help him because he was the most convenient. It wasn’t like Cas picked him because Dean was special or anything; it wasn’t like Cas had feelings for someone like Dean... No Cas could do way better. He would do better than Dean once Dean stopped being selfish and decided to let Cas go out into the world to use his new skills.

Dean’s heart just needed to learn to shut the fuck up and stop getting too overeager when it came to the blue-eyed sex God he had in his arms.

But not yet…

“So I was thinking we should probably get you some toys soon? Start trying them out,” he asked, trying to sound casual.

Cas shuffled a little before he sat up enough to look down at Dean. He seemed to be pondering the idea of getting some toys before he turned a slight shade of pink and turned away. Bashful almost. “I uh—I should probably order them online?”

“I think it’s better if you go to the stores and test them out.” Dean shared, moving to sit up on the bed as well. “That way you can check the sizes and everything.”

“Have you... been to a sex store?”

“Uh. Once. This one girl I fooled around with was into toys.” Dean didn’t bother to say much else and Cas didn’t ask any questions. Instead, he continued looking mortified at the thought of actually stepping foot into an adult shop.

“I don’t... I don’t think I’d be comfortable going in there by myself. Online is probably best. I’ll just—I’ll just order a few different things.”

Fuck. Why was it so fucking cute to see Cas blushing like this?

“We can go together.” Dean said quickly, trying to put Cas out of his misery. “Just not to one around here or anything.” He added, thinking about how awkward it would be to run into someone they knew as they were trying to buy dildos. Yeah, he’d definitely rather not deal with that.

Cas didn’t seem convinced though. “I’m sure online is just fine.”

Dean rolled his eyes. He knew Cas was shy and would probably be a bit anxious going in but Dean also knew his friend would feel much more comfortable after he talked to a consultant and got something that would actually be good for him instead of based on what some online review said.

“The consultants there know their stuff. You’ll find something right for you faster than online.”

“Okay,” Cas agreed quietly, he looked uncomfortable but he must’ve known Dean wouldn’t just throw him to the sharks since he nodded and smiled slightly. “We can go. Is tomorrow okay?”

“Works for me.”

For a moment it looked like Cas was going to say something or maybe lean back in and lie down with Dean for a little while longer but his hand trailed through a glob of come still on his stomach and he grimaced.

“I should go shower.”

That same sting of rejection from a few days ago hit Dean again but he forced it away and gave his friend a winning grin. “Need a buddy? You know, I don’t want you to slip and fall or something.”

“You’re incorrigible.”

“You love it.”

All that earned him was an eye roll.

Saturday October 28, 2017

As they had discussed, they drove a few miles away from the college to find a store they wouldn’t be recognized in. Being as they were in Las Vegas they really had a slew of places to pick from and decided to go with one that didn’t have garish objects in the window. He didn’t want Cas to have an aneurism from anxiety after all. (Okay, maybe Dean was a little intimidated by mannequins dressed in leather and feathers with floggers in their hands—sue him).

This place felt clean and simple. There were of course some more obscure items that Dean didn’t think he’d ever find sexy but there weren’t dicks and strap-ons hanging from the ceiling so that was a plus.

When they walked in a woman came over and asked if they had any questions and Cas had taken off with her, leaving Dean to peruse the store for the time being. He started wandering the small trinket area with the dick straws and magnets before he found himself wandering the aisles. He was blown away by the sheer amount of vibrators that were offered. Seriously, how was someone supposed to pick which level of vibration was ideal? And the different shapes and textures that went along with them? It was insane.

Eventually he found himself drifting around the store aimlessly after a while and just staring at the different objects on display wondering how many people actually used them. Currently he was in an area for anal stimulation. That’s how one of the consultants cornered him.

“Are you interested in any of these?”

“Oh what?” Dean stammered for a second before he followed her gaze to the items on the shelf. “Am I? Oh—no. No. Just trying to figure them out.”

“They’re prostate massagers.”

He felt himself blush as he tried to not be an awkward fuck talking about ass toys. “You just stick them in and then let it do its thing?”

Smooth, Winchester.

“Essentially.” The woman agreed. She had blue and green hair and a metal lip ring but looked far less terrifying than most people with wild colored hair who worked in sex stores. She looked normal, really. Even her attitude was kind as she explained the toy Dean was standing next to. “People like to masturbate while using them generally.”


“Would you be interested in something like that?”

“Oh. Oh no. I uh.” He felt like an idiot stammering like this but the thought of something that bulbous going into his—nope. No thanks. “I’m not into anything going—no. I was thinking for my friend?”

“Blue eyes?”

“Yeah, he’s uh, new to this and I wanted him to come here to get some things he could try out.”

“What a considerate partner… friend?”


The woman accepted his answer for what is was, but even Dean knew he didn’t sound all that convincing.

“Were you hoping for items you could use together or for his use?”

“His—his use. That maybe could be used on him by a p-partner.”

The woman nodded her head and gestured to a device that was a bit longer than the other ones he’d been looking at but still stated it was a prostate massager.

“I would recommend this massager as many of the reviews have reported hands-free orgasms from it. It’s also easier to find the prostate since it’s larger than many of the more targeted ones.”


“But if this isn’t something you’re looking for there are some dildos I can show you that might be good.” Dumbly he followed the woman around the corner and to the next aisle where she pointed to one of the smaller dildos. This one had a bit of a curve to it.

“So this is my recommendation for beginners since it is a very pliable silicone and the length and width are not outrageous. Many costumers of varying experience levels and sexualities have recommended it.”

“Okay. That, uh, that sounds—“ A few feet away down the aisle was his friend and Dean breathed a sudden sigh of relief. “Oh Cas, there you are, come here.”

His friend smiled and showed off the store shopping bag that had a few items in it. “Dean! The lady has been showing me so many things. I had no idea that there were such specific items. Did you know they make anal plugs with tails on them?”

“Ha-uh, no.” Dean blushed, rubbing at the back of his neck. “I did not know that. Uh, did you get one?”

“Oh no. Well not one with the tails but I thought getting a plug would be something worth trying. Have you found anything?”

“Yeah she was—“ Dean looked around to see that the consultant had left them, “She was just here but she uh was telling me that this a good beginner uh, toy. I think you should go with this one.”

He showed off the smaller dildo that definitely looked the safest choice to him. Especially when he glanced all the way towards the end to see one that looked about the size of his fucking head. How did anyone… nope! He wasn’t even going to finish that thought.

Cas apparently was displeased with Dean’s choice as he assessed the object. “But it’s so... small.”

“Dude, that’s pretty much the size most guys are.”

“You’re significantly bigger than this though. Why would I want to get this one?”

If Dean’s chest puffed out just a little at that remark, he hoped no one saw but… damn. Bless Cas and his smooth ego stroking abilities. Still, Dean trusted the woman and figured that if she recommended the smaller ones for beginners then it would be for the best, right?

“It seems like a good beginner one though. And I’m telling you most guys will not be this big.” Dean said, gesturing to some more girthy ones.

“But this one looks more like your size.” Cas’s eyes were focused on one that was actually more comparable to Dean’s own size, this one perhaps had an inch on him.

“Cas, it’s kind of big to start with.” He argued anyway making Cas huff a little.

“But if you’d have agreed to have sex with me I would have been ‘starting with’ a penis this size. It’s not like it’s not going to fit with adequate prepping.”

Dean sucked in a breath realizing just how right Cas was. If Dean had agreed to it, he’d have had to get his dick into Cas’s tight hole somehow… and that thought suddenly made him very anxious. What if he’d have agreed and had hurt Cas? Which he would have because, holy fuck, Dean didn’t know what the hell he was doing.

He was going to hurt Cas and he was going to make Cas hate having sex… what the fuck was Dean even thinking? How could he have agreed to do more with Cas without having any fucking clue what he needed to do to make sure that his best friend wouldn’t get hurt. Hell, he’d only randomly thought about grabbing lube last week because it suddenly dawned on him that his own ass didn’t get wet when he was turned on which meant that if he wanted to finger Cas it wouldn’t have gotten slicked up on his own like a girl does.

Suddenly Dean felt overwhelmingly out of his element.


“I’d rather go with one more sizable and comparable to the penis I have experience with.”

“I’d feel more comfortable going with the smaller one. It’s not going to be comfortable your first few times.”

“Then we get both.” Cas said with a shrug, grabbing each box and putting them into his bag. “When the smaller one proves not to be as pleasurable, we’ll switch to the larger one.”

“You’re a stubborn bastard. I’ll give you that.” Dean’s anxiety still felt palpable but he didn’t want to dampen Cas’s mood. His friend actually seemed excited to be here and experiment with the things they were buying.

“Would you like to see what else I got?” Cas asked with a grin, looking like he’d just purchased a bucket of candy or something.

Dean couldn’t stop himself from smiling. “Yeah, show me.”

October 29, 2017

Cas had bought a green silicone butt plug, blue anal beads, a vibrator, and the two dildos that they’d argued over. He’d been very interested in starting off with the anal beads and of course Dean couldn’t say no. So after washing it thoroughly they’d played around with them that night. Dean could tell they weren’t Cas’s favorite since neither of them really knew what to do with them, and even after pausing for a little to Google what to do, they were still clueless. Regardless, Cas had a good orgasm but Dean could tell that it wasn’t as toe-curling as he’d gotten use to watching.

So when Cas had asked if they could try one of the dildos the next night, Dean readily agreed, wanting to redeem himself a little.

Even though he didn’t care if he didn’t get off at all, and was solely focused on making sure that Cas came better than he did the night before, Cas seemed focused only on Dean’s own orgasms. Like the first time Dean had ever fingered Cas, his friend laid down on the sofa to suck Dean down so that Dean could get his fingers in him and every time he had Cas like this, Dean couldn’t help but feel like a virginal teenager again getting to touch someone for the first time.

He tried not to get embarrassed each time touching Cas’s ass made him shoot at ten times the rate as usual, but fuck… every fucking time. “It’s getting embarrassing how fast you can get me to blow. Like damn dude, are you trying to set a record?”

“Maybe…” Cas grinned devilishly, suckling around Dean’s spent cock.

“You’re making me feel like I’m thirteen again. Can’t even last five minutes.”

“I like it.”

Dean felt a jolt of something course though him just looking down at Cas in that moment but he tried to tamper it down, not wanting to fuck with those types of emotions at the moment. He had a job to do, and that job involved getting a fake dick up his friend’s ass until his friend came as hard as possible.

“So do you want to do this on your back or stomach?” He asked, watching with silent glee as a flush crawled up Cas’s neck.

“Uh, stomach is fine.”

Dean nodded in agreement and had Cas climb onto his bed and get a pillow under himself while Dean went to grab the toy from where they’d left it on Cas’s desk.

When he crossed over to the bed Cas had a look on his face that gave Dean pause.

“What’s wrong?”

“I was just thinking…. I can—I can prep myself if you don’t want to… I can—I can just do it all myself… I—I shouldn’t have assumed…”

“No!” Dean practically shouted. He back peddled quickly, not wanting Cas to think Dean was too eager. “I mean… it’s cool. It’s like—it’s like we’re pretending to have real sex. What it would be like, right? So you kind of need a partner for that right?”

“Uh, yeah—yeah I guess so.”

Dean could still sense some hesitance in Cas’s voice and he scrambled to convince Cas that this was a good idea. Fuck. Dean needed Cas to say yes to let Dean help him with this. He didn’t want their arrangement to end here, especially since Cas hadn’t even gotten off that well yesterday and Dean didn’t want Cas’s last memory of their time together being a shitty orgasm.

“You do. And—and this way you can learn how to vocalize the things you want. Yeah, that’s actually really important to learn.” Dean was thankful that his slight desperation was actually kind of making sense. “You have to be open to communication with your partner because if they’re doing something you really don’t like and you just keep silent about it thinking it will get better… it will never get better. So you—you need to learn how to say what you want, you know? You won’t be able to learn that if you’re just doing this by yourself.”

“Oh. That—that makes a lot of sense. Okay.” Cas agreed, he looked a little more comfortable. “You’re sure though?” He asked.

“I want you to feel comfortable when you are with a real partner. I want it to be good for you. Only if you want to do this.” Dean was quick to add. He realized that maybe his panicked attempts to keep Cas weren’t fair, especially if Cas really didn’t want Dean’s help anymore. “If you don’t want my help though, I can just leave and let you do this yourself?”

“I do! I still want your help.” Cas said suddenly. That’s when moved to roll over again but Dean stopped him before he could.

“Wait. How about—how about you lay on your back? I want—uh most of the time first times are uh in the missionary positions so I uh, I want you to experience it that way but if you hate it you can lay on your stomach obviously. Or if that’s how you’d prefer it then it can be on your stomach I was just thinking…”

“I’ll lay on my back.” Cas said calmly. Maybe he could tell that Dean was just as nervous as he was. He moved the pillow under his lower back and put a few under his head as well. “This okay?”

“Perfe—yeah—yeah, you’re good. You’re good like that.” Dean stammered, looking down at his naked friend. He couldn’t get over how fucking perfect Cas looked. How much skin was there just for Dean to touch—no. He couldn’t let himself touch or else he’d probably never be able to stop. He had to remind himself he wasn’t helping Cas out for his own pleasure, it was for Cas. To make Cas feel happy and confident. That’s what mattered.

“Uh, maybe, maybe bring your knees up?” Dean suggested. Cas complied immediately, bringing his legs up just enough that Dean could now see his hole. “Yeah, like that. Good.”

Nervously excited, Dean crawled up to the end of the bed. His mouth went a little dry as he looked down at Cas laying there with alert, eager eyes. Dean didn’t exactly know what he was doing apart from some frantic googling when Cas was sleeping the other night but he figured as long as he took care of Cas he’d be fine.

He reached over to where they’d dropped the lube on the bed and clicked it open. He drizzled a little onto his fingers and took some time to warm it up. There was something charged in the way Cas’s eyes refused to leave Dean’s as Dean moved further between his legs and rubbed the warmed lube around his hole. And Dean too couldn’t look away. He was drawn into the way that Cas’s lips parted as Dean’s first finger breached his rim and slowly began pressing in. A small whine escaped in a breath and Dean instantly soothed his hand up and down Cas’s thigh.

“Is that okay?”

“Mm? Oh—oh yeah. Yeah, it’s good.”

He took his time. He didn’t care if it took him nearly ten minutes to work just two fingers into Cas… Dean needed this. He needed to touch his friend the only way he was allowed to for as long as he was allowed to.

And Cas let him.

He had no clue how long it had been until he was able to fit three of his fingers.

“Do—do you feel stretched? Nothing hurts?” He asked softly, hardly a whisper.

“I’m good.”

“Okay I’m going—I’m going to uh—I’m going to use it now.”


There were nerves in Cas’s voice but they verged more on eagerness than anxiousness. Dean took his time slipping his fingers out of Cas and lubing up the toy generously before lining it up with Cas’s fluttering pink hole.

“Tell me if you’re okay.”

And maybe because Dean was still trying to draw this out as much as possible, he didn’t press in right away. Instead he rubbed the silicone head around Cas’s perineum and traced it over his hole just to watch the way Cas squirmed and hear how he gasped.

It was when Cas let out a whispered version of his name that Dean couldn’t deny him any longer. Gently he pressed the tip of the toy inside his friend and slowly rocked it in and out until Cas’s body accepted it fully.

A sharp breath of, “oh,” was pressed from Cas’s lips.

All of Dean’s movements stilled in that instant, assuming the worst. “Am I hurting you?”

“No.” Cas breathed out. “No. It—it doesn’t hurt at all. Just—just feels… full?”

Dean’s own breathing was heavy and his dick was definitely interested in this situation but he ignored his own needs and focused on the most important ones.

“Are you ready? Can I move it?”

“Yes. Please,” Cas panted. So Dean did what he needed to. He slid the toy nearly all the way out before pressing back in, doing his best to imitate what he would do if he were the one inside of his friend. “Oh whoa.” Cas said immediately. Dean continued with his movements and Cas continued with his stunned vocalizations. “Oh whoa… that’s… whoa.”

“Good whoa or bad whoa?” Dean asked, still pressing the dildo in and out of his friend.

“Hngh—g—good whoa.”

Cas’s hands seemed to tremble at his sides as he tried to clutch at the sheets. Soon enough his hands were wandering across his chest, splaying out and clutching like he was trying to get a grip of something clawing through his body. Into his hair they went and back down his chest, caressing down to his tummy and back up again. It looked like he was searching for something, trying to get hold of something to tether himself to the world.

Dean couldn’t keep his eyes off him, even as he pressed the dildo in and out of Cas’s ass, he couldn’t keep his eyes on the way Cas’s eyes closed and his body writhed on the bed. Not able to think straight, Dean let his left hand wander up Cas’s thigh and up across his belly, suddenly meeting one of Cas’s stray hands and gripping onto him tightly.

Cas held onto his hands with a vice grip.


“You okay? Is it too much?”

“No—no. S’good. Can—can you go—can you try it faster?”

Dean had to swallow a groan, as his mind surged with images of Cas whispering that into his ear as Dean fucked into him. “Yeah…” Dean whispered, immediately indulging in Cas’s wish and jerking his wrist faster. “Like this?”

“Mmm—yeah—yeah that. Oh god.”

“What do you need?”

“I—I need—oh god.”

Cas’s hips were wriggling on the bed and Dean could see the way his cock was practically begging to be touched.

“Touch yourself. Come on.”

Even though Cas wasn’t left-handed, his right hand was currently latched onto Dean’s. He brought his non-dominant hand around his shaft and started tugging with a purpose.

He was so worked up that Dean thought it’d only be a matter of seconds before his friend exploded. Yet, right when Dean thought Cas was at his peak his friend slowed down the movements of his hands.

“Dean—Dean—Dean…. Wait.”


“I—can I—I wanna try the bigger one.”

“You’re so close though.”

“Please—please I… I wanna feel.”

There was no way Dean would deny Cas this with the way he sounded. But the way he looked? Dean was done for. Cas’s skin was flushed and his hair was standing on end and he just looked so damn perfect. Something primal in Dean sang knowing he’d done this to Cas—Dean made him look like this.

Without any argument Dean pulled the toy out of his friend and crawled off the bed to grab the larger piece. It was garish and pink and weighed his hand down significantly more than the other one, but the detailing on it looked so much more like a real dick.

His mind was so kind to remind him how Cas compared it to his own and now Dean was about to put it into his best friend’s ass. He wasn’t going to survive this.

As quickly as he could, he slathered lube all over it and brought it back to Cas’s entrance and pressed in, looking for any single sign that it might be too much.

“Hngh—oh, oh fuck.”

Dean stilled immediately again, worried as hell. “Is it hurting?”

“S’big. Not—not hurting.”

The way Cas’s eyes scrunched made Dean wonder if he was lying or not. It sent all of Dean’s aflutter. “Cas—I’m not sure—“

But Cas’s eyes opened at that moment and he sought out Dean’s hand once more. “Please? Want more.”

There was a plea in Cas’s eyes and Dean couldn’t help but give into it. “Okay—“ he agreed again right before he pressed the toy a little deeper.

“Ohh, mmm.”

He’d never heard Cas sound like this, so vocal with need.

“Fuck… are you sure?” He asked, feeling more overwhelmed than he had in a long time in the bedroom.

“Yeah—yeah. Dean… Promise.”

This time Dean kept his movements slow and kept his eyes locked on Cas’s face, making sure that his friend wasn’t showing any signs of discomfort whatsoever. It was when Cas’s hips started to press down to chase the toy and his friend’s hand was flying over his dick that Dean started to speed up his movements.

“Oh—oh god. Oh god, Dean—oh!”

He knew Cas was close. He couldn’t fucking wait to see this orgasm. “Come on.”

His wrist was starting to ache but he didn’t let up even a little.

“Yesyesyesyes---“ Cas half-whispered then suddenly those words were cut off by a silent scream.

Dean pressed the dildo deep, right at that moment wishing more than fucking anything it was him who got to be inside Cas at this moment. That Cas could have wrapped himself around Dean and rode out that orgasm with Dean’s cock deep inside him.

God Dean was jealous of a fucking toy because he wanted to feel Cas clenching around his dick. Fuck. He didn’t know if he’d be able to keep his sanity much longer if he watched his friend come on these toys anymore and this was only the first time he got to see such a glorious fucking sight. What would he even do if he saw this for days? Weeks?

There was no way he could survive seeing Cas so fucking perfect like this.

Dean wanted him so bad it made him insane.

He pulled the toy out of his friend and dropped it on the bed. He moved between Cas’s legs, hovering above him a few inches and took his own cock in his hand. As Cas laid below him Dean couldn’t help but stare at the come that had splattered on Cas’s chest and stomach. And like that Dean was blowing his load again, mixing his own release with Cas’s.

He fell to the side, careful not to land on his friend. This time Cas was the one who pulled Dean into his arms. This time Dean was the one who buried his face in Cas’s neck. This time Dean was the one who fell asleep on his friend.

This time Dean realized that there was nowhere he’d rather be and he was fucking terrified.