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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.