So most of them are PWPs but there’s some longer one too. I don’t really know what’s your most preferable twink I hoped it’s between 14-18 years. Here you go:
UNDERAGE!CAS

A Brief GlimpseRating: PG-13Word count: 12,356Summary: Castiel is utterly convinced he can’t love anyone, but Sam, so when a strange occurrence at a carnival shows him otherwise, he doesn’t know what to do.
Note: very cute I guess I recced it before.
A Moment To Be RealRating: NC-17Word count: 62,758Summary: Dean is a janitor at a religious highschool, Castiel is a preachers son, but he’s not as good as you’d expect. Dean’s rather surprised too. Rebellious underage Cas/Janitor Dean. WARNINGS FOR INCEST.
Note:Hm the first few chapter are good but then it’s a mess.
All That JazzRating: NC-17Word count: 4,100Summary: “No one’s ever done this to you, have they?” he murmurs. “No one’s ever touched you like this before.” Cas shakes his head, cheeks flushing prettily, and when he twists around to look at Dean his face is half frightened, half eager, and all innocence. 
Note:Wow okay, so if you were looking for very young Cas and middleage Dean pwp this is your stuff. 
Baby I Got Your MoneyRating: NC-17Word count: 4,300Summary: Twinkie hooker Cas has a rough night with Dean, or does he?
Note:I hated it at first but then :) plot twist
Boys Next DoorRating: NC-17Word count: 7,485Summary: Castiel Novak has got a crush on the boys next door.
Note:It’s wincestiel but it’s hot.
Drunk On YouRating: MWord count: 4,645Summary: Cas is Sammy’s best friend, and Dean is the older brother who accidentally wants the seventeen year old. Sam and Cas are both seventeen, and Dean is twenty-one.
ForbiddenRating: MWord count: 107,385Summary: With a past behind him, seventeen year old Castiel has escaped and is starting afresh in a new high school. He meets, Dean Winchester, his older and more mature teacher who knows right from wrong but sometimes temptation is just too much to overlook.
Note:Now this is a longer and a good one.
Heat of the MomentRating: NC-17Word count: 12,120Summary: Dean finds a sixteen year old omega living on the streets during his first heat, so he takes the kid home to keep him safe. But, as it turns out, he’s finding the kid difficult to resist, himself.
Heaven on EarthRating: MWord count: 4,907Summary: Dean and Cas have been together for three months after Dean found sixteen year old Cas wandering around during his heat and mated with him, and Cas’ unwavering nausea is rocking the boat a little.
In Another Life It Could Happen To YouRating: NC-17Word count: 3,100Summary: Dean is a college professor, and Cas is his gifted, but shy student. Only, as it turns out, maybe not so shy after all.
Note:Read it.
It’s A ComplexRating: NC-17Word count: 5,996Summary: Cas is Dean’s next door neighbour back in his hometown, and Dean hasn’t seen him for two years. In those two years, the kid turned sixteen, got hot, and wormed his way into all of Dean’s fantasies.
Let Me Follow You DownRating: NC-17Word count: 6,794Summary: In which Dean Winchester comes back to his home town for longer than a week for the first time in five years to find nothing much has changed.. except puberty has been really kind to the former babysitter of his younger brothers, Castiel Novak. Which wouldn’t exactly matter if Dean doesn’t have to find a babysitter for his brothers at a couple of hours notice.
Together, They Fright CrimeRating: NC-17Word count: 86,657Summary: Dean is an ex-Green Beret who hunts monsters for the FBI. Castiel is a teenage psychic on his last chance. Together, they fight crime.
Note:Long and TRIGGERY, very.
Wanna Steal Your InnocenceRating: NC-17Word count: 6,634Summary: Dean’s a mechanic in his late 20s and Cas is a freaking sixteen year old high schooler. Dean shouldn’t want to fuck the kid as much as he does.
Welcome to Uncanny ValleyRating: NC-17Word count: WIPSummary: Prompt: Dean, a lonely engineer/scientist, has a secret. He’s attracted to young boys, but he doesn’t want to risk getting caught nor does he actually want to hurt a child. He decides to create robot!Cas, a legal and “ethical” alternative. Cas is highly advanced and looks like a very real 9-12 year old boy. He can do anything a human could do: he can move, walk, and talk, perform tasks, and can serve as an outlet for Dean’s desires. Though at first Dean only sees him as a very expensive sex toy, he begins to develop feelings for the robot after a while which leads to much angst and thought. Would like to see Dean starting to expect human things out of Cas before catching himself, like telling him to come eat and then remembering Cas can’t eat or asking him his opinions on things before realizing that Cas can’t form opinions, all of his opinions are just programmed in. Dean eventually even wants genuine love from Cas, though he knows he’ll probably never get it. Up to author whether or not Cas can ever feel anything back (maybe Dean programs feelings into him? Maybe he’s more advanced than Dean realises? Maybe it’s magic? Maybe it’s Maybelline???). Robot!Cas should be like show!Cas: awkward, very serious and literal, generally clueless about all things human.

UNDERAGE!DEAN

Dustbowl DanceRating: MWord count: 12,000Summary: Dean and Sam live alone on the edges of a no-name western town after the death of their parents. While 17 year old Dean struggles to keep them both in home and food, Cas and Jimmy - notorious criminals - ride town to town leaving chaos in their wake. Dean never expected them to ride to his town.
FatherRating: NC-17Word count: 3,000Summary: Even though he’s new to their church, Dean knows Father Castiel wouldn’t hurt him. Not ever.
GrownRating: NC-17Word count: 2,900Summary: It’s bad enough he has to have a sitter. The fact that it’s Cas is almost unbearable.
I Pray the Lord, My Soul to KeepRating: NC-17Word count: 3,400Summary: The entire town of Lawrence, Kansas, thinks Castiel is the best preacher they’ve ever had. He’s kind of quiet, and intense, but he’s devout and very polite. Only Dean Winchester knows what his priest is truly like, and he’s not talking.
Summer Vacations SuckRating: NC-17Word count: 4,500Summary: Summer vacations suck, and Cas seems bent on making it awkward for Dean.
Note:Wow that fucking car scene. That. Fucking. Car. Scene.
Teenage Dream (Confessions of a Pizza Delivery Boy)Rating: NC-17Word count: 3,600Summary: The first time Dean delivers pizza to 401 Lazarus St. is when Castiel Milton instantly becomes the man of Dean’s teenage dreams.
Note: Cute and Castiel is in character.
Your Dirty SecretRating: NC-17Word count: 5,400Summary: “Your yard looks like crap. I’ll come round after school and sort it for you if you pay me ten bucks.” Those were the first words Dean ever said to Castiel. How was Castiel supposed to know then that he was going to fall in love with Dean? AU.
Note:I liked it very much.

BOTH OF THEM (basically all the high school AUs)

A Long Time ComingRating: TWord count: 1,515Summary: Dean and Cas have been friends for as long as they can remember. It might be the slowest love story in history.
Among the WreckRating: NC-17Word count: 110,000Summary: The fate of the world has been decided and two human vessels are the key to the final battle that will trigger the apocalypse. Not content to leave anything up to destiny, Heaven takes matters into its own hands. But a simple assassination is complicated by the interference of one of their own, leaving the future in limbo and the angel Castiel to pay the ultimate price for his actions. But what should be the end is only the beginning. The angel’s fall from grace crash lands him in the body of a young Jimmy Novak as his soul departs. The process leaves Castiel with no memories of his celestial past; he knows himself only as Jimmy Novak, a sickly child whose overnight recovery is nothing short of miraculous. But as Jimmy’s life starts anew, Dean Winchester’s has all but ended.It’s under these circumstances that these two boys come together and forge a friendship that slowly develops into something more. But their path was never meant to be easy and fate eventually intercedes, thrusting them both into the roles they were always meant to play: the angel and the hunter. The Righteous Man and his Protector. 
Friends Will Be FriendsRating: NC-17Word count: 4,000Summary: Cas was his best friend, and it’s not like he’s gonna do or rather request anything unusual, well unusual for them anyway.
HomecomingRating: NC-17Word count: 8,400Summary: AU PWP - Dean just got kicked out of military school, just as his Dad got remarried to Anna - bringing her techie nerd son right into his house - and right under Dean’s nose. Smut, total, smut.
Unconditionally Horny and Eternally SadRating: NC-17Word count: 31,700Summary: It’s your typical boy-likes-boy story. Boy 1 is sad, Boy 2 is horny. Let’s call Boy 1 Castiel Novak; he’s spent his entire life being left behind by everybody around him. Boy 2 is named Dean Winchester; he just wants Castiel to fall in love with him, and is determined to show Cas he isn’t everybody.
We Became the Gravel Beneath the TiresRating: NC-17Word count: 19,700Summary: College!AU in which Dean hasn’t seen Sam in months- or heard from him in weeks. It’s hard staying in touch when Dean lives across the country and his brother’s a genius studying law, but he’d be lying if he said he didn’t miss the stupid Sasquatch. Cas, who’s tired of his cookie-cutter lifestyle and is Dean’s best friend/roommate, sees it as a perfect opportunity for a road trip. Despite Dean thinking Castiel has gone absolutely insane, they embark on a journey across the United States- the road a catalyst for finding things in themselves and each other. Crappy motel rooms, roadside diners, and cigarettes, become the perfect mix for falling in love, but roads aren’t complete with twists and turns, and cheap wine on a warm, spring night might not have been such a great idea. 90% Fluff and Other. 10% Angst.
With All The Lights Turned DownRating: M/NC-17Word count: 4,331Summary: Childhood - Highschool AU. Dean and Castiel’s discoveries in sexuality begin at the tender age of nine. Warnings for underage and sensitive subjects.

art link

So most of them are PWPs but there’s some longer one too. I don’t really know what’s your most preferable twink I hoped it’s between 14-18 years. Here you go:

UNDERAGE!CAS

A Brief Glimpse
Rating: PG-13
Word count: 12,356
Summary: Castiel is utterly convinced he can’t love anyone, but Sam, so when a strange occurrence at a carnival shows him otherwise, he doesn’t know what to do.

Note: very cute I guess I recced it before.

A Moment To Be Real
Rating: NC-17
Word count: 62,758
Summary: Dean is a janitor at a religious highschool, Castiel is a preachers son, but he’s not as good as you’d expect. Dean’s rather surprised too. Rebellious underage Cas/Janitor Dean. WARNINGS FOR INCEST.

Note:Hm the first few chapter are good but then it’s a mess.

All That Jazz
Rating: NC-17
Word count: 4,100
Summary: “No one’s ever done this to you, have they?” he murmurs. “No one’s ever touched you like this before.” Cas shakes his head, cheeks flushing prettily, and when he twists around to look at Dean his face is half frightened, half eager, and all innocence. 

Note:Wow okay, so if you were looking for very young Cas and middleage Dean pwp this is your stuff. 

Baby I Got Your Money
Rating: NC-17
Word count: 4,300
Summary: Twinkie hooker Cas has a rough night with Dean, or does he?

Note:I hated it at first but then :) plot twist

Boys Next Door
Rating: NC-17
Word count: 7,485
Summary: Castiel Novak has got a crush on the boys next door.

Note:It’s wincestiel but it’s hot.

Drunk On You
Rating: M
Word count: 4,645
Summary: Cas is Sammy’s best friend, and Dean is the older brother who accidentally wants the seventeen year old. Sam and Cas are both seventeen, and Dean is twenty-one.

Forbidden
Rating: M
Word count: 107,385
Summary: With a past behind him, seventeen year old Castiel has escaped and is starting afresh in a new high school. He meets, Dean Winchester, his older and more mature teacher who knows right from wrong but sometimes temptation is just too much to overlook.

Note:Now this is a longer and a good one.

Heat of the Moment
Rating: NC-17
Word count: 12,120
Summary: Dean finds a sixteen year old omega living on the streets during his first heat, so he takes the kid home to keep him safe. But, as it turns out, he’s finding the kid difficult to resist, himself.

Heaven on Earth
Rating: M
Word count: 4,907
Summary: Dean and Cas have been together for three months after Dean found sixteen year old Cas wandering around during his heat and mated with him, and Cas’ unwavering nausea is rocking the boat a little.

In Another Life It Could Happen To You
Rating: NC-17
Word count: 3,100
Summary: Dean is a college professor, and Cas is his gifted, but shy student. Only, as it turns out, maybe not so shy after all.

Note:Read it.

It’s A Complex
Rating: NC-17
Word count: 5,996
Summary: Cas is Dean’s next door neighbour back in his hometown, and Dean hasn’t seen him for two years. In those two years, the kid turned sixteen, got hot, and wormed his way into all of Dean’s fantasies.

Let Me Follow You Down
Rating: NC-17
Word count: 6,794
Summary: In which Dean Winchester comes back to his home town for longer than a week for the first time in five years to find nothing much has changed.. except puberty has been really kind to the former babysitter of his younger brothers, Castiel Novak. Which wouldn’t exactly matter if Dean doesn’t have to find a babysitter for his brothers at a couple of hours notice.

Together, They Fright Crime
Rating: NC-17
Word count: 86,657
Summary: Dean is an ex-Green Beret who hunts monsters for the FBI. Castiel is a teenage psychic on his last chance. Together, they fight crime.

Note:Long and TRIGGERY, very.

Wanna Steal Your Innocence
Rating: NC-17
Word count: 6,634
Summary: Dean’s a mechanic in his late 20s and Cas is a freaking sixteen year old high schooler. Dean shouldn’t want to fuck the kid as much as he does.

Welcome to Uncanny Valley
Rating: NC-17
Word count: WIP
Summary: Prompt: Dean, a lonely engineer/scientist, has a secret. He’s attracted to young boys, but he doesn’t want to risk getting caught nor does he actually want to hurt a child. He decides to create robot!Cas, a legal and “ethical” alternative. Cas is highly advanced and looks like a very real 9-12 year old boy. He can do anything a human could do: he can move, walk, and talk, perform tasks, and can serve as an outlet for Dean’s desires. Though at first Dean only sees him as a very expensive sex toy, he begins to develop feelings for the robot after a while which leads to much angst and thought. Would like to see Dean starting to expect human things out of Cas before catching himself, like telling him to come eat and then remembering Cas can’t eat or asking him his opinions on things before realizing that Cas can’t form opinions, all of his opinions are just programmed in. Dean eventually even wants genuine love from Cas, though he knows he’ll probably never get it. Up to author whether or not Cas can ever feel anything back (maybe Dean programs feelings into him? Maybe he’s more advanced than Dean realises? Maybe it’s magic? Maybe it’s Maybelline???).
Robot!Cas should be like show!Cas: awkward, very serious and literal, generally clueless about all things human.

UNDERAGE!DEAN

Dustbowl Dance
Rating: M
Word count: 12,000
Summary: Dean and Sam live alone on the edges of a no-name western town after the death of their parents. While 17 year old Dean struggles to keep them both in home and food, Cas and Jimmy - notorious criminals - ride town to town leaving chaos in their wake. Dean never expected them to ride to his town.

Father
Rating: NC-17
Word count: 3,000
Summary: Even though he’s new to their church, Dean knows Father Castiel wouldn’t hurt him. Not ever.

Grown
Rating: NC-17
Word count: 2,900
Summary: It’s bad enough he has to have a sitter. The fact that it’s Cas is almost unbearable.

I Pray the Lord, My Soul to Keep
Rating: NC-17
Word count: 3,400
Summary: The entire town of Lawrence, Kansas, thinks Castiel is the best preacher they’ve ever had. He’s kind of quiet, and intense, but he’s devout and very polite. Only Dean Winchester knows what his priest is truly like, and he’s not talking.

Summer Vacations Suck
Rating: NC-17
Word count: 4,500
Summary: Summer vacations suck, and Cas seems bent on making it awkward for Dean.

Note:Wow that fucking car scene. That. Fucking. Car. Scene.

Teenage Dream (Confessions of a Pizza Delivery Boy)
Rating: NC-17
Word count: 3,600
Summary: The first time Dean delivers pizza to 401 Lazarus St. is when Castiel Milton instantly becomes the man of Dean’s teenage dreams.

Note: Cute and Castiel is in character.

Your Dirty Secret
Rating: NC-17
Word count: 5,400
Summary: “Your yard looks like crap. I’ll come round after school and sort it for you if you pay me ten bucks.” Those were the first words Dean ever said to Castiel. How was Castiel supposed to know then that he was going to fall in love with Dean? AU.

Note:I liked it very much.

BOTH OF THEM (basically all the high school AUs)


A Long Time Coming
Rating: T
Word count: 1,515
Summary: Dean and Cas have been friends for as long as they can remember. It might be the slowest love story in history.

Among the Wreck
Rating: NC-17
Word count: 110,000
Summary: The fate of the world has been decided and two human vessels are the key to the final battle that will trigger the apocalypse. Not content to leave anything up to destiny, Heaven takes matters into its own hands. But a simple assassination is complicated by the interference of one of their own, leaving the future in limbo and the angel Castiel to pay the ultimate price for his actions. But what should be the end is only the beginning. The angel’s fall from grace crash lands him in the body of a young Jimmy Novak as his soul departs. The process leaves Castiel with no memories of his celestial past; he knows himself only as Jimmy Novak, a sickly child whose overnight recovery is nothing short of miraculous. But as Jimmy’s life starts anew, Dean Winchester’s has all but ended.It’s under these circumstances that these two boys come together and forge a friendship that slowly develops into something more. But their path was never meant to be easy and fate eventually intercedes, thrusting them both into the roles they were always meant to play: the angel and the hunter. The Righteous Man and his Protector. 

Friends Will Be Friends
Rating: NC-17
Word count: 4,000
Summary: Cas was his best friend, and it’s not like he’s gonna do or rather request anything unusual, well unusual for them anyway.

Homecoming
Rating: NC-17
Word count: 8,400
Summary: AU PWP - Dean just got kicked out of military school, just as his Dad got remarried to Anna - bringing her techie nerd son right into his house - and right under Dean’s nose. Smut, total, smut.

Unconditionally Horny and Eternally Sad
Rating: NC-17
Word count: 31,700
Summary: It’s your typical boy-likes-boy story. Boy 1 is sad, Boy 2 is horny. Let’s call Boy 1 Castiel Novak; he’s spent his entire life being left behind by everybody around him. Boy 2 is named Dean Winchester; he just wants Castiel to fall in love with him, and is determined to show Cas he isn’t everybody.

We Became the Gravel Beneath the Tires
Rating: NC-17
Word count: 19,700
Summary: College!AU in which Dean hasn’t seen Sam in months- or heard from him in weeks. It’s hard staying in touch when Dean lives across the country and his brother’s a genius studying law, but he’d be lying if he said he didn’t miss the stupid Sasquatch. Cas, who’s tired of his cookie-cutter lifestyle and is Dean’s best friend/roommate, sees it as a perfect opportunity for a road trip. Despite Dean thinking Castiel has gone absolutely insane, they embark on a journey across the United States- the road a catalyst for finding things in themselves and each other. Crappy motel rooms, roadside diners, and cigarettes, become the perfect mix for falling in love, but roads aren’t complete with twists and turns, and cheap wine on a warm, spring night might not have been such a great idea. 90% Fluff and Other. 10% Angst.

With All The Lights Turned Down
Rating: M/NC-17
Word count: 4,331
Summary: Childhood - Highschool AU. Dean and Castiel’s discoveries in sexuality begin at the tender age of nine. Warnings for underage and sensitive subjects.

art link

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