Posted originally on the Archive_of_Our_Own at https://archiveofourown.org/ works/6571717. Rating: Explicit Archive Warning: Underage Category: M/M Fandom: Supernatural Relationship: Castiel/Dean_Winchester Character: Castiel Additional Tags: Masturbation, Masturbation_in_Shower, Twink_Castiel, Teacher_Dean, Anal Fingering, Alternate_Universe_-_High_School Series: Part 1 of Dear_Mr._Winchester Stats: Published: 2016-04-16 Words: 1158 ****** Dear Mr. Winchester ****** by thelonelywriter Summary Cas has some explicit thoughts of his History teacher Mr. Winchester whilst in the shower. Said thoughts lead to some explicit activities... Notes HOT OF THE PRESSES, I wrote this like twenty minutes ago. I don't know how many of you guys will actually want to read this since it's literally just Cas masturbating to the thought of Dean in the shower but I wrote it because for some reason lately I have had the great, deep need to write some twink!Cas and I found a piece that I wrote out like on paper that was just Castiel masturbating so I figured, hey, why not just write this with Cas as a twink and see what everyone thinks ¯\_(ツ)_/¯ I tagged this as underaged just because they do have a major age difference, Cas is in the range of sixteen to eighteen, you pick what age suits your fancy!! Alright, I'll shut up now so that you guys can read!! (Side Note, this now has a sequel and the link for it is in the end notes!!!) See the end of the work for more notes Castiel grumbles to himself as he tosses his bag down by his bed and plops down on it with a sigh. He’s had a shitty day at school and he just wants to eat some Ramen and read fanfiction ‘till he falls asleep. But the load of homework and upcoming tests contained in his backpack plead another story. Cas, eager to dismiss the whole entire test thing, the whole entire homework thing, stands up, beginning to shuck off all of his clothes. He toes off his shoes and socks, steps out of his jeans and boxers, tugs off his t-shirt until he’s fully naked. Once he is he grabs a towel, heading to the bathroom. There’s no one home tonight, both his Mom and Dad are still at work so Cas doesn’t have to risk being seen completely naked as he wanders down the hall and towards the bathroom where he shuts the door behind him. He hangs up his towel and immediately turns on the water tap, turning the temperature up to a nice, hot spray of water. He waits a bit for it to warm up before he steps in and lets the water run over his body with a sigh. Sure, maybe he’s not going to be reading fanfiction and eating Ramen, but at least he can have a little peace and quiet. He tries to be mindful the first few minutes of being in the shower, tries to keep thoughts of school and grades and everything away as he rinses the shampoo from his hair. But slowly, those thoughts creep back into his head as he grabs the soap. He thinks over his day, his day that was awful because he had stayed up way too late the night before so he was sleep deprived. But, as he’s going over his day in his head, his mind catches on something. His History teacher. Cas bites his lip as he thinks over his features. His name is Dean Winchester, though to Cas he’s known as Mr. Winchester. Dean is one of the most attractive people that Castiel has ever believed to have seen. Light brown hair, muscular build, tan, freckled skin, and these eyes that are green but have little specks of gold in them that you can see if you look hard enough and of course Cas is looking hard enough because Christ, what Cas would do to have those eyes looking down on him with Dean’s cock shoved down his throat. Cas blinks, looking down. He’s already getting a little hard and he knows that this is wrong, he shouldn’t be jerking off to the thought of his History teacher, but he can’t help it if he has a vivid imagination and is great at picturing what Dean’s cock looks like. “No,” Castiel simply says, looking down at his dick that is desperately trying to raise itself, getting harder every second. Cas chews on his bottom lip, letting the arm that was hanging by his side bend, his hand coming up, slowly creeping up his thigh until it’s wrapped around his cock. “Or yes,” Castiel sighs, relenting in what he knows that he shouldn’t be relenting in. He turns a bit, leaning his back against the shower wall and letting the warm water of the shower wash over him as he begins with lazy yet firm strokes to his cock. He still has some soap on his hands so things are slick and fucking perfect. Cas closes his eyes and just thinks of Dean for a second. Of that low, smooth tone that Cas would beg to hear moaning his name. Cas thinks of how muscular he is, of how he could probably pick Cas up and slam him against the wall, fuck him until Cas can’t walk straight. Cas groans at the thoughts, his hand speeding up. But then he gets an idea. He opens his eyes to find the soap, and he reaches out for it, getting some onto his fingers. He reaches back, letting one finger brush that furl of muscle that he’s looking for. He slips one finger in with a sigh, feeling the pleasure that’s settled in his groin jump just the slightest at the pleasant intrusion. He wraps his other hand around his cock, fucking up into his fist lightly as he pumps one finger in and out of himself. He lets out a pleased moan at the feeling, thankful that no one’s home so that he doesn’t have to bite back any noises. He lets himself drift back to the fantasy of Dean, just Dean in general. He thinks about Dean’s fingers, how they would probably feel so good inside of him. Cas knows what Dean’s fingers are like, he’s taken note every time he hands in papers and their fingers brush. He’s got thick fingers, perfect fingers just like the rest of him. God, he probably has a thick cock too. Cas groans at the thought and slips a second finger in, fucking them in and out of himself as he keeps thrusting up into his own fist. The pleasure inside of him is hot and the water falling over him is too so it feels like he’s on fire but in the best way imaginable. Cas tilts his head back, imagines what it would feel like if Dean were there to suck bruises into his skin, to let everyone know that Cas is his. Castiel soon crooks his fingers in just the right way, hitting his prostate and sending pleasure to every nerve inside of him. He lets out a loud moan in response, hurriedly slipping in a third finger. He’s panting by now, his chest rising and falling quickly, pleasure burning throughout his whole body. He can feel the stretch of three fingers and it’s marvelous, perfect really. All he can imagine is what it would be like if those were Dean’s fingers, Dean’s fingers opening him up to take Dean’s cock. “Fuck,” Castiel hisses as he gives a light squeeze to the base of his dick. God, he wants that so bad, for Dean to bend him over his desk and fuck into him so hard that the desk jolts across the floor. Castiel can feel the wave of heat, of pleasure inside him beginning to crest, and with a few jabs of his fingers against his prostate, a few firm strokes of his cock, that wave is cresting so beautifully that Cas comes with a shout, come pulsing over his stomach as his hand slowly stills, his fingers doing the same. Castiel pants, slowly pulling his fingers out of himself and resting against the shower wall, the come on his stomach slowly washing away from the spray of the water. “Oh, God,” Castiel pants, still coming down from the high of his orgasm. One thing’s for sure, he’s definitely not going to be able to look Dean in the eye tomorrow. End Notes Side Note: I know that I have some prompts that need to be filled, I promise you that I am doing my best to get those to you guys, sorry that it's taking so long!! Other than that, let me know what you guys thought!!! Maybe you liked the whole going solo thing, maybe you missed Dean and Cas actively together, or maybe you just hated it!! Either way, feedback is marvelous :) Though I am currently swamped with prompts you can send me one over_here and I will try my best to get it to you as soon as possible!! You can also just talk to me, send me ideas, headcanons, all of that is welcome!! Thank you guys so much for reading, I hope that all of you guys are doing well :D <3 Xoxo (There's a sequel over_here if you guys want to read that!!!) Please drop_by_the_archive_and_comment to let the author know if you enjoyed their work!