Supernatural
Insecure!Dean
Tag · 15 works
Works
Some results are potentially explicit
Supernatural
A potentially explicit work
Supernatural
Loyalty
by Dancingdog
Dean accompanies Cas to a weekly 'Asexual Awareness' meeting and they make some friends (and enemies) along the way. However, Dean is shocked when someone approaches him with the intent to not only cheat on their own partner, but to make sure Dean cheats on his as well. Cas catches them in the act...
Supernatural
Just the Right Shape
by FluttersnFun
Dean wants to ask Cas out, but doesn’t believe he should until he gets into better shape.
Supernatural
Its better
by Morethancupcake
" Because Dean didn't take pictures now, didn't sing birthday songs loudly. And certainly not with him."It's 4 in the morning, and Castiel is thinking about all that is wrong in their life. But then Dean wakes up.(link to the wonderful art by linneart in the notes)
Supernatural
A Date with the Director
by Aria_Lerendeair, StarlightDragon
Sequel to "Letter to the Director of Admissions" Dean and Cas have their second first-date. Dean's more nervous than he wants to admit to, but this is Cas, and things were always easy with Cas. He's just not sure that's still the case.
Supernatural
Dating the Director of
by Aria_Lerendeair, StarlightDragon
A look into a few of the milestones of their relationship as Dean is dating the Director of Admissions.
Supernatural
A potentially explicit work
Supernatural
You are more than that
by IronEyes, NotfunnyDean (IronEyes)
Dean doesn’t want to go with Sam to his fancy Christmas party, that changes when he meets Castiel Novak.
Supernatural
Entreat Me Not
by OhSnap9292
Whoever said that couples who argue together stay together clearly had not considered that an emotionally stunted monster hunter and an angel of the Lord would end up shacking up together.
Supernatural
A potentially explicit work
Supernatural
Secrets
by spn-x-reader (rimesire)
You finally have the relationship with Dean you've always wanted, but does he feel the same?
Supernatural
A potentially explicit work
Supernatural
A potentially explicit work
Supernatural
Dizzy Daydreams & Drunken Hazes
by billyteddytrash
There's nothing more intimidating to Dean Winchester than attention from one Castiel Milton. He was the ideal crush, all shaggy hair and blue eyes, not to mention totally and completely unattainable. Nothing in the world would get Cas to give Dean even the slightest bit of recognition. Up until the second half of his senior year, he didn't need to worry about any attention from Cas. But for some reason, halfway through January, Castiel starts acknowledging him. Long looks and suggestive smirks, winks for no reason, the whole ten yards. When Dean confronts Castiel about the constant distraction, things get a whole lot messier and a whole lot more interesting. With only five months left of high school, what will these mixed signals and long-suppressed feelings lead into?