Supernatural
Awkward Dean
Tag · 78 works
46 works open to everyone here carry this tag; 87% are complete. The average one runs about 3,300 words. Read any of them in your browser, save it as an EPUB, or listen to it.
Works
Some results are potentially explicit
Supernatural
A potentially explicit work
Supernatural
Swipe Right
by Englandwouldfall
In which Dean sort of came out via Tinder, Castiel-from-across-the-hall never buys enough groceries and Sam and Charlie need to stop interfering with both his phone and his (none-existent) love life.
Supernatural
A potentially explicit work
Supernatural
A potentially explicit work
Supernatural
These Lies we Cherish
by Semira
“Shh,” Dean's voice, when he speaks, is scraped raw and bitten-back, his breaths broken, but Sam knows his eyes will be dry. This is a happy moment, and neither of them is allowed to cry right now. “Sammy,” Dean whispers, hands busy stroking through Sam's hair and down his back (gentle, feather-light so as not to disturb the broken ribs). “You hear that? The ambulance is coming. You're gonna be all right, huh? You're gonna be all right.” In other words: John responds a little too enthusiastically to Sam's snark when he uncovers his son's acceptance letter, and Sam leaves, injured and betrayed. Thankfully, it doesn't end there. For the prompt: What happened during the Stanford fight and how Dean felt about his brother leaving (and not wanting him to go). Anything about this would be great.
Supernatural
Homebound
by Semira
Dean does it—as he does everything—with a bang. Later, Sam won't be able to remember quite how it went down (he thinks Rowena in chains was involved, remembers sigils and spellwork and maybe even the actual door of the temporary cage being blown off), but he does remember, with perfect clarity, the very first moment he heard Dean's voice, raw and desperate. “Damn it, Sam, answer me if you can hear me!” He remembers staring, semi-conscious and trembling, through the bars of the temporary cage, remembers leaning toward the voice. In other words After what happened to his brother in 11x09, O Brother Where Art Thou, Dean will do anything to get Sam out and get him home. The rest they can figure out as they go. Needless to say, please don't read this if you don't want spoilers for the events of the episode.
Supernatural
A potentially explicit work
Supernatural
A potentially explicit work
Supernatural
First Impressions
by thatwriterlady
Cas is at the end of his college education. He only has a few classes left, one of which is history. He opts to take it at the end of the day, since he knows all of the material it should be a cakewalk. He even chooses the most laid back history teacher the university has. He should be able to skate through the course with his eyes closed. Except every asshole on the football team decided to take this class at the same time as he did. And his crush, Dean Winchester is in this class too. Oh, and of course the professor got switched out for the biggest dick they had. What else could possibly go wrong?
Supernatural
A potentially explicit work
Supernatural
Lollipop
by mattzerella_sticks
Dean Winchester isn't the most popular boy in his school. In fact, you couldn't get lower on the totem pole than him. But he's come to accept it, even if it means dealing with people like Gordon every time he tiptoes out of the status quo. Making first impressions is hard given that he's known most of his classmates since the beginning. But besides Charlie, he doesn't have anyone in his corner.Except for Castiel, the school's quarterback who transferred to their school last year. But he'd never go for someone like Dean...(This fic is based around the totally adorable Dean characterization in 14x04)
Supernatural
Sex on the Beach
by remivel
Dean isn’t a shy person. He has a lot of friends, and he never has problems picking up women at bars. However, there’s something about Castiel that makes him act like an awkward teenager. He’s been thinking of asking Castiel out for months. But first, he needs to muster enough courage to come up to him and say ‘hi!’
Supernatural
Dyslexic In A Library
by orphan_account
Dean is dyslexic. For that he is alienated at school, struggles to make friends and get good grades. In an attempt to pass English class, he goes to the town library to find a book to read and write an essay about. What he doesn't expect is to be found there by his long-time crush: Castiel.
Supernatural
A potentially explicit work
Supernatural
Twice Removed
by Semira
It takes until Sam is unconscious in a pool of his own blood for Dean to realize that maybe something's gotta give. So maybe Dean's angry. Maybe he gets a little reckless, slow to respond when he hears the sounds of a scuffle. He has a good excuse, though, airtight: he'll protect his brother to the end, no questions, but this? This isn't his brother. In other words... It takes near death for Dean to warm up to his soulless brother, but some things are just muscle memory. Sam refuses pain meds, Dean thinks the soulless guy is kinky, and in the end, maybe he understands the fathomless robo-Sam a little better than he did before.
Supernatural
Not in So Many Words
by Semira
Sam thinks something's wrong when Dean won't meet his eyes and leaves to buy pie by himself. He knows something's wrong when Dean returns with pies and a salad, for God's sake. He's absolutely beside himself when Dean offers to share the pie. Dean never shares pie. It's somewhere in the Book of Things that Are, right beside gravity and sunrises. In other words: Dean has a secret. Sam may or may not figure it out. Angsty, awkward brotherliness placed in the fourth season, somewhere between Jump The Shark and The Rapture.
Supernatural+1
I Sent Him An Owl
by aw_godusopp_no
Gryffindor courage? What Gryffindor courage? Dean's going through an 'I'm super gay for my Hufflepuff bestfriend Castiel' crisis and Sam has had enough, so he suggests Dean asks Castiel to be his date to the Yule Ball. Except things don't exactly go as planned.
Supernatural
The One Where Dean Buys
by mahbbys
Based on the prompt "Cas is the cashier at the sex store where Dean buys his toys/extra large condoms/lube." Dean buys his condoms at the local porn shop and strikes up an unlikely acquaintance with the cashier, Castiel.
Supernatural
Santas Gift
by thatwriterlady
Cas lives alone, and with the holidays arriving, he sets about filling his home with Christmas cheer, even if he's the only one that will be celebrating it. He's lonely, with no family, no real friends, and when he thinks about how he's going to be spending another Christmas alone, he whimsily makes a wish, asking Santa to bring him someone that he can fall in love with, and that will love him back. It's funny how sometimes, even the wildest of wishes can come true.