Hello!

I hope you like this one, I'm planning on doing a series of this, following Cas and Dean's life, to see how they grow, learn and love each other and themselves, experimenting with different kinks and "first times", so, if you like this one, please let me know, and if you have some kinks or ideas you'll want to see in the future, please, write them in the comments so I can see what are your preferences.

Please, keep in mind that english is not my first language, so I accept help and constructive criticism, but not hate by any means. If you want to contact me in a more private way, on my profile page of AO3 I have my email and my tumblr, feel free to contact me.

Anyway, I hope you like this fic!

The first time Dean sees Cas' dick is at a party.

Dean is wasted, after an uncountable amount of beer and, at least, eight shots of tequila, he's officially and utterly drunk. And he couldn't care less: next week his best friend Cas and him will drive far away from Laurence to begin new adventures in College, and the excitement had him drinking a little too much, but, who could blame him? After so many years listening to a never ending chant of "you're worthless and you'll never do anything in your life" from his teachers he managed to make it to school in a full ride. Cas had always said he could make it, but Dean didn't believe him, not until he received the acceptance letter, and after that, making a run to Cas' house to see that it was true, that Dean wasn't dreaming. But it was true, so Dean was partying like there was no tomorrow.

But, just after 2 A.M he started feeling a little dizzy. Dancing, jumping and maybe humping a little bit in the makeshift dance floor with whomever wanted to be close to him was fun, a lot of fun, and suddenly he really needed to sit down, and puke, preferably both, in a quiet place away from all the people, where he could listen to his own thoughts.

Once outside of the house, careful of stepping out of the neatly furnished wood porch from the backyard, he fell onto his knees in front of an empty plant base and puked for what it felt like an eternity. When it was out of his body, he felt so good that he had enough energy to stand up and pee, in the same base; but that was all the energy he had left, so rather ungracefully, he laid down on the floor, too close to the base full of vomit but too drunk to care for real, and started to doze off. Man, what a night, he thought, don't forget to dump this fucking base into the trash.

After that it was all a blur, a nice, calm and quiet blur, until the dreaming started, a really good dream. He couldn't recognize a face, nor really see clearly what was happening, but the moaning was enough for him to know what was happening: a nice wet dream. Only he didn't feel a thing, only heard the noises. What kind of shitty wet dream is this, he thought before waking up and sitting and trying to stand up using the wooden bars of the fence. It wasn't a good idea, apparently, because he ended up on his knees, with his face smashed against the wooden bars. Fuck, he thought, grunting from the pain, that will leave a mark. Fuck, this is so embarrassing.

And then he realized it wasn't a dream, at least not the moans he thought were part of the shittiest wet dream ever. No, in fact, there were people on the porch, making out heavily, discarding clothing and making a lot of noise. Dean couldn't recognize the person who was on top of the other, but the one sitting down was clearly Cas. He could recognize him in a crowd, blindfolded, and that was definitely Castiel in the middle of foreplay, just about to fuck someone at a party.

Dean felt like puking again but for a completely different reason.

The worst thing? He couldn't even stand to get away because he was so wasted. His legs didn't respond, and he was still grasping the wooden bars of the fence, face still plastered against it.

Heartbreak.

Heartbreak, all over again, like they were fifteen again. Cas and him had a history, they knew each other since they were babies. Charles Novak and John Winchester were best friends and neighbors. They spent so much time together that no one was surprised when Naomi and Mary were pregnant at the same time, and neither when their first borns became best friends since the moment they met: just two bald babies, who looked at each other and started to laugh —a toothless laugh, full of joy and glee, trying to touch each other with their chubby little hands. So it felt as natural as breathing when, during Castiel's 15th birthday, they kissed. It was the best kiss of Dean's life, he constantly fantasized about that moment, remembering how was to kiss Cas' lips, to have him so close, his thin body between his arms and soft fluffy hair between his fingers. It was heaven. But the Novaks were a conservative family, sort of, and even if Cas was a little more modern and liberal than his parents, some things can be untaught, and the next day Castiel appeared at his house, with a "promise ring" because he wanted to marry.

"Dean, after what... after what we did, I think it's the right thing."

"Are you fucking serious, Cas? We just kissed, nothing else. Maybe we can date but...marriage?! What the fuck, dude."

"I just...I just thought it was the right thing to do. It's the proper thing to do."

"Cas, man" Dean sighed. "Do you ever want to marry me? Or it's the bumbo-jumbo-crazy-shit your parents told you you HAD to do?"

"It's not 'crazy shit', it's a way to live a morally correct life, I thought you respected that."

"I do! Otherwise I wouldn't be your friend...look, Cas. Let's not get sidetracked, I know we...feel something, right?" Dean looked at the floor before speaking again. "I'm not that dumb, but, fuck, do you really want that? Or is just a duty call?" He was feeling exasperated. "Tell me the truth, man, you can't play with my feelings like that. Damn, Cas, I won't let you play with your own feelings like that."

And that was it, Castiel cried that day, because he truly felt that that was his duty and he didn't want to lose Dean's friendship because he was too conservative to kiss another person. Dean promised him that nothing could come between them, and that they'd always be best friends, no matter what. He told Cas that they should experiment, know other stuff before trying something as committed as marriage, and that maybe Castiel would realize the love of his life was out there and he wasted the chance to be with them just because he married the first person he kissed. But, secretly, Dean was dying because he was a closeted romantic, and he dreamed about having a love life like his parents, marrying his school sweetheart, having kids and a house. And if Cas had told him he wanted to marry him because he was in love with Dean, just as in love he was with Cas, he would have said yes, in a heartbeat. Yes, yes, yes. A hundred time yes, because he loved Castiel so much, but it looked like Cas didn't feel the same way. That, plus the fact Dean had troubles communicating and being open about his feelings, concluded in the mess he was in right now: hopelessly in love with his best friend, pining for him for another three years, while trying to get over him with other people, only making it worse. Falling even more in love with Castiel, only to see how Castiel tried, in his own way, to date and go out with other people, silently destroying Dean in the process. And now, now Dean got a premium seat to watch how someone, someone who was not him, tried to get in Cas' pants.

He knew his friends and him worked to make Cas more open minded, less conservative, so he'd try new stuff, meet new people and experiment some things before he got married. But knowing was a thing, watching it was a completely different story.

And Dean wanted to puke.

He saw in slow motion how the girl —now he was sure that the person on top of Cas was a girl—, slid her hand inside Cas' pants. That's it, it's over, fuck, Dean thought.

"Oh, oh, no, no, no way, no way that is getting in me in any way, no." The woman said, loudly, shaking Dean from his drunken stupor.

"What's wrong?" He heard Cas ask, fear tangible in his voice.

"I don't want to keep going anymore. Thanks for the good time, but that's enough." Dean had never punched a girl. Well...that's a lie, he had punched Jo several times, but it was not the same, Dean would kill her. How dare she make his best friend feel bad?

"Was it something I did? Was I not satisfactory?"

She had the audacity to laugh. Dean was so mad he actually separated his face from the fence, and started to stand.

"That's a way to put it. Don't think too hard about it. See you around, Clarence." And she left.

It was Meg, obviously, who else called Cas by that nickname? Fuck her, fuck her with a tree log, Dean muttered to himself, walking towards Cas without realizing, sitting down besides him. Suddenly, he wasn't as drunk as he was before. Honestly, he felt really sober.

"What happened over there, man?"

"Hello, Dean." he answered, then immediately asked "Is my penis ugly, Dean?"

"Whoah! What? No? I don't know, why are you asking? Did Meg said something?"

"Megan implied that something was not satisfactory about my penis after she tried to give me hand stimuli."

"So she freaked out after she grabbed you."

"Basically."

"Shit, man, I don't know what to say."

"Is it me? It's my pe-"

"Please, Cas, say cock or dick." Dean interrupted him, exasperated.

"I don't know what is wrong with me." Concluded Cas, gesturing at his crotch, the zipper still down and the fly open, and Dean had to double check because...yes, Cas was still hard.

"Oh boy." said Dean. "I know what Meg's problem was." Cas looked at him with hope. "The problem was...is...your dick is huge, man" Dean felt his face turn red, embarrassed to the core.

"Excuse me?" Exclaimed Cas.

"I think she didn't wanna fuck you because you have a tyrannosaurus cock."

"I didn't want to have intercourse with her! I just...I just wanted to experiment, just like you guys said, but I never thought..."

"That your cock would scare her away?" Said Dean, smirking.

Now it was Cas' turn to blush.

"It's just...I never thought something so intimate about me would scare people away. What if it's always like this? I know it does not look like it but, I don't want to be rejected again."

Maybe Dean was still drunk because in a second he was kneeling in between Cas' legs, looking at him with big eyes, desperate for the other man. He wanted to see that dick, not only the bulge in Cas' underwear, but the real deal, in his mouth like, yesterday. Dean needed it so bad, and he felt no inhibition stopping him from begging for what he wanted. Because he was, suddenly, really aware that in any second anyone could come and snatch Cas away. Or that anybody could come and hurt him and make him feel ashamed of his body. Dean wouldn't let that happen.

"Please, Cas, please, let me suck your cock"

Cas nodded, muttering a soft "yes", looking at Dean with big, shiny eyes and ran his fingers through his hair. Dean moaned at the feel of Cas' fingers twisting at the nape of his head, kneading his hair.

That was enough for Dean.

He started mouthing at Cas' dick through his underwear, feeling the other man tremble against him, tightening the fingers on the back of his neck, encouraging him to lick more, feel more, make him harder. Cas smelled so good, he felt so warm and soft against his mouth, Dean couldn't help himself and started to lick him, still trough his underwear. Cas moaned pitifully, lifting his hips, rutting against Dean's face. Straightening his back a little, Dean worked Cas' dick out of his boxers and held it in his hand.

"Fuck" said Dean. It was huge. He thought he had a good sized dick, but Cas' was ridiculous. He was at least three inches longer than Dean. "Fucking Jesus Christ, it's like my arm"

"Don't be obtuse, Dean." Panted Cas, and Dean didn't have to be looking at him to know Cas had just rolled his eyes.

"How can you be snarky when you're about the get head?"

But before Cas could say anything, Dean lapped at his dick, making the other man moan loudly. Dean gave little licks to the head, tasting the pre-come at the tip, playing with Cas' slit, sucking slowly and wetly at the tip of his cock. It felt so huge, so fucking huge, Dean thought it'd never fit, but the want was so deep. He was hungry for Cas' cock in his mouth, against his tongue, thrusting into his throat. With a kind of determination he didn't know he had, he let Cas' dick get deeper into his mouth, sliding against his tongue while hollowing his cheeks, sucking slowly but surely Cas' dick into the channel of his mouth.

"I have dreamt about this" he heard Cas say. The dick in his mouth felt so thick, it was hard to breathe, his jaw hurt and he was starting to tear up, but he'd die before taking that dick out of his mouth. Dean wanted all of it, wanted to taste everything, wanted to hear every moan Cas had to give, and wanted to feel him cumming deep inside his throat. That, plus the speech Cas was giving made him hard as a rock.

"I've dreamed about touching you again, of having your body close to mine. I know I'm not supposed to do it, but I cannot help it, and I touch myself thinking of you. You look so beautiful like this, Dean." He could feel Cas' fingers touching his lips, where they were stretched around his cock. "I wish I knew before, oh Dean" Cas moaned really loudly. And Dean whimpered with his mouth full in return, making vibrations go through the dick in his mouth.

Now Dean was crying. He couldn't do anything about it, the stretch was unusual, but it felt so right to have Cas in his mouth. If only he could do this forever, having Cas always in his mouth, warm, practicing until he could fit the whole thing inside his mouth, deepthroating him to the root.

"Dean, Dean, Dean…" Cas was moaning, and thrashing against him. Dean held his hips, but Cas was lone gone; he felt him getting thicker inside his mouth, pulsing and emanating more warmth. He knew Cas about to come. He felt how the fingers against his head pulled calling his attention, making him groan with pleasure. He made eye contact with Cas, his blue eyes, clear, teary with dilated pupils and looking excited. Dean gave a little nod and five seconds later, Cas came into his mouth for what felt like an eternity.

The next morning Dean woke up sore, his head hurt, his jaw, his throat, his fucking knees hurt. He didn't want to open his eyes and start the day. His stomach rumbled, another part of his body that was complaining against him. Fuck, fuck, fuck. Everything that had happened the night before was still fresh in his memory, at least he hadn't forgetten. Did he suck Cas' dick after pucking? Man, that was awful, but he didn't have a bad taste in his mouth, it tasted only of mint.

Without opening his eyes he rolled on the bed, immediately he knew he was in his room, how did that happen?

Cas.

Without opening his eyes he knew, from the core of his heart, that Cas was there with him.

"Morning, sunshine." He groaned, rolling onto his back, opening his eyes to look at the ceiling.

"Hello, Dean. I'll bring you breakfast in just a minute, your mom saved some for you. Do you need anything?"

"Nothin'...maybe s'mthing for this fucking headache…"

"Look at your nightstand. I will be right back."

Just as Cas had said, there were two yellow pills beside a huge glass of water, he took the medicine and drank all the water. Two minutes later, he was feeling a little better. Everything in his room looked more organized, Cas woke up early, tidied the room, and gave him a shower and brushed his teeth, apparently.

Shortly, Cas was back in his room, with a tray full of food. The minute the tray was on his lap he started to eat. The other man let him eat in silence, Dean knew Cas must have eaten with the rest of the Winchesters earlier in the morning. Neither of them said anything. Dean was about to dig into the bowl of fruit when he saw a small velvet box hidden behind it. He knew what it was. He felt like everything in his body contracted, nevertheless, he still got the box with shaking hands and opened it.

Just as he thought: a ring.

"Cas...I know a blowjob is way bigger than a kiss...but we've been through this…and if last night..."

"Hear me out, please."

Dean just nodded.

"I know that when we were younger I rushed things, and you were right, I did not want to marry you at the time, it was because I felt it was my duty to marry the person who I deflowered. It's silly, I know, but that's how I grew up. My mother thought that when my father kissed her she would get pregnant. That's the kind of people who raised me, and you know it, but thanks to you and our friends I know better. But you were right. And this...this is about last night. I can't deny it, but Dean, it is not because I feel the obligation to marry you because you performed felattio on me and that I must marry the one I share carnal intimacy with. No…"

Cas stood up from the foot of Dean's bed and kneeled on the ground, taking Dean's hands.

"What happened last night showed me that I can't keep living my life knowing you can do that with someone else who is not me. That I can't let you, nor myself, keep experimenting before we settle down, because I know I want to spend the rest of my existence and after life with you. I can't be silent on how much I love you, not anymore. And yesterday showed me that."

"Cas…" Dean was at a loss for words. He needed to say so many things, how he also felt like dying when Cas was with another person, or how the other man could brighten his day with just a smile, how important Cas was in his life. They'd start a new life together, going to college, sharing a dorm, then a house, together...There were so many things, so many words that wanted to come out of his mouth. He didn't know where to start…

Man up, Winchester.

"I love you, Cas. I love you so damn much." He settled for that.

"Dean" Cas said, holding Dean's hands against his chest, nuzzling his fingers with his stubble while leaving little kisses against his knuckles. "I've loved you since the moment I pulled you out of that hell they call the sandbox, even when you stabbed me with that fake toy knife and made me cry. And now, after all those years, I love you more, so please, will you do me the honor of marrying me? Not today, not tomorrow, but someday in the future?"

Dean smiled.

"Of course I'll marry you."

And Cas surged to kiss him. Their first kiss since they were fifteen, and it was as good as they remembered, even more so when, in the middle of it, Cas put the ring on Dean's finger.

"Now that's out of the way." Said Cas, deep voice rumbling against his skin. "We have to talk about your hygiene habits."

"What?" Asked Dean, still dazed from the kiss.

"Dean Winchester, yesterday was a beautiful experience, but you performed oral sex after you vomited from alcohol intoxication. I had to wash your teeth for you when I brought you home!"

Dean laughed, hard, falling again into the bed, still holding Cas' hand, the ring a welcome weight in his finger. He really loved that man.

"Well...that explains the mint aftertaste"

Thanks for reading!