1 - 20 of 145 Works in Age Play Little Dean Winchester

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  1. Tags
    Summary

    One of Dean's quiet little days. What will ensue?

    Language:
    English
    Words:
    2,390
    Chapters:
    2/?
    Comments:
    3
    Kudos:
    28
    Bookmarks:
    4
    Hits:
    341
  2. Tags
    Summary

    Dean age regression and age play one shots (requests open)

    Language:
    English
    Words:
    9,291
    Chapters:
    9/?
    Comments:
    34
    Kudos:
    135
    Bookmarks:
    12
    Hits:
    3616
  3. Tags
    Summary

    "Hey."
    Cas says in a soft timid voice,
    His hand ceasing its movement in my hair,
    But not pulling away.

    "What's wrong Dean?"
    --------------------
    "I Know I don't say this often Dean,
    But I'm really proud of you.
    And I'm happy that you have finally found that slice of apple pie,
    You have been dreaming off our whole lives."
    ------------------------------------------
    "You Damn idjits!
    I have been standin out here in the boiling heat for 10 whole minutes!
    What did you guys forget ya invited company?"

    "Well hey Bobby,
    I missed you too."
    ---------------
    "Because it's not normal Dean and I don't want to push your boundaries and do something that may make you uncomfortable.
    Or ruin what we have when your little
    Or-"-
    --------------
    A four chaptered section in my ongoing series Little did you know.

    Series
    Language:
    English
    Words:
    5,630
    Chapters:
    3/5
    Comments:
    20
    Kudos:
    47
    Bookmarks:
    4
    Hits:
    739
  4. Tags
    Summary

    Tumblr Post by bend-me-shape- me, requested by ladystiltskin67 / transparentparadisglitterzombie / blazeeblake / tinyteacupsfan / joham-fate to be turned into a fic:

    Deaged dean following cas everywhere, not wanting to do anything if cas isn't there, always running after him and gripping the back of his trench coat "cas don't leave!!" even if cas was just going to his room and coming back in less than a minute and sam watches them wondering if this is just a normal thing for a little kid to do or if this just dean's deep fear of losing cas emerging

    Series
    Language:
    English
    Words:
    2,847
    Chapters:
    1/1
    Comments:
    8
    Kudos:
    52
    Bookmarks:
    7
    Hits:
    347
  5. Tags
    Summary

    Prompt - Sam gets Dean in trouble for breaking a costly vase that he didn't break, and cas believes sam and spanks dean, and in anger dean goes into a secret hiding place and after a few hours of looking for him cas hears sam talking to his stuffed animals about getting dean in trouble on purpose and has sam show him where deans hiding spot is and after a lot of convincing deans comes out and sam apologizes, but he doesn't walk away without punishment and gets a timeout and sent to bed, after dean and cas cuddle and the next morning all is forgiven.

    Authors note - yeah, i didn't stick to the prompt very well but idc. i write it how i like and that's all that matters.

    Series
    Language:
    English
    Words:
    1,186
    Chapters:
    1/1
    Kudos:
    24
    Hits:
    448
  6. Tags
    Summary

    After one of the many times Dean and Sam die, God decides he’s done bringing them back to life. He gives them an ultimatum - they can die and go to heaven, or they can come back to life as an angel.

    Together, the brothers choose to be nestlings, and Castiel and Gabriel are more than happy to help.

    Let’s just say it’s quite an adjustment

    ** This fic is inspired by the absolutely WONDERFUL fic by SailorChibi called Hatchling

    Language:
    English
    Words:
    7,785
    Chapters:
    6/?
    Comments:
    68
    Kudos:
    352
    Bookmarks:
    64
    Hits:
    5604
  7. Tags
    Summary

    Deans always knew that sleeping with a pacifier in his mouth isn't normal but when has his life ever been normal? He's tried to justify it and tell himself that when his mother died, this was the result of that. It stunted his mental growth in that particular area so whenever he thinks about his mother, he needs his pacifier. Sam doesn't know and he never will know. This is Dean's dirty little secret. This is what Dean sucks on for a few minutes after a particularly hard hunt.

    Series
    Language:
    English
    Words:
    1,278
    Chapters:
    1/1
    Comments:
    1
    Kudos:
    34
    Bookmarks:
    3
    Hits:
    319
  8. Tags
    Summary

    A collection of infantilism one shots that people have requested and what I have done myself. A winter gift for Into_Oblivion!

    VERY IMPORTANT NEWS IN CHAPTER 29!

    Language:
    English
    Words:
    31,908
    Chapters:
    29/?
    Comments:
    322
    Kudos:
    735
    Bookmarks:
    71
    Hits:
    36646
  9. Tags
    Summary

    Request: How about this littles Sam & Dean are playing on the floor with their toy cars ! Sam is wearing a pull up & Dean is in a green t shirt that is the color of his emerald eyes & batman underwear ! They are playing nicely until Sammy grabs the toy car Impala away from Dean & Dean gets mad & pushes Sammy backwards causing him to hit his head on the hard floor & he screams & cries & caregiver Castiel comes in & gives Sammy hugs : kisses his boo boo away & calls him his little baby boo & then he gives Dean . . . u decide the rest a spankjng time out or. ? But Dean does feel guilty of courses !

    And...

    Something with an angel.

    Series
    Language:
    English
    Words:
    1,224
    Chapters:
    1/1
    Kudos:
    14
    Bookmarks:
    1
    Hits:
    288
  10. Tags
    Summary

    Dean Winchester's going to get coffee and doesn't realize his zipper is undone, but Castiel does. Little does Dean know that he just ran across a very sexy, experienced Dom who now has his eye on him. These are their stories. *dun dun*

    Language:
    English
    Words:
    90,245
    Chapters:
    23/?
    Comments:
    622
    Kudos:
    1018
    Bookmarks:
    195
    Hits:
    25744
  11. Tags
    Summary

    Prompt: Could you please write one where Dean has had a long hunt and has come back worn out. It's only Cas and Dean so Cas takes over as Daddy and helps him get clean, take care of any wounds, and wraps him up for bed. Dean has a nightmare and Daddy Cas is there to make it all okay?

    Series
    Language:
    English
    Words:
    554
    Chapters:
    1/1
    Kudos:
    19
    Bookmarks:
    1
    Hits:
    435
  12. Tags
    Summary

    Request: Can you do little Dean, Mommy Jo and big brother Sam? Dean gets hurt on a hunt, and needs lots of kisses and cuddles from his Mommy.

    Series
    Language:
    English
    Words:
    1,126
    Chapters:
    1/1
    Comments:
    3
    Kudos:
    16
    Bookmarks:
    1
    Hits:
    352
  13. Tags
    Summary

    Before God left, He gave instructions for a new method of creating angels: one that allows an angel to take a consenting adult human as their child. By feeding them grace over the course of an unspecified amount of years, the human's - now known as a nestling's - soul will change enough to be able to produce a modified form of grace, thereby keeping angels from dying out.

    After the end of the apocalypse and with Sam having returned to Stanford, Dean is at a loss. When Castiel offers to take Dean as his nestling, Dean has no idea how far Castiel plans to take this - or how much he'll end up needing and enjoying it.

    Series
    Language:
    English
    Words:
    177,717
    Chapters:
    83/?
    Comments:
    3727
    Kudos:
    9419
    Bookmarks:
    1035
    Hits:
    373629
  14. Tags
    Summary

    prompt: dean is in a bad mood because of something going wrong in his big life (maybe a hunt, or if it’s an AU he didn’t get the job he wanted, anything like that). he kinda feels like a failure so even though he wants to be little in order to feel better, he fights it hard. cas knows what is happening and slips into daddy mode to gently coach dean into little space, and then they do some calming stuff and dean gets lots of cuddles and love (and they talk about what was bothering dean after when they’re both big, but it doesn’t have to be in the story only if you want to write it).

    from instagram

    Series
    Language:
    English
    Words:
    1,153
    Chapters:
    1/1
    Comments:
    3
    Kudos:
    27
    Bookmarks:
    1
    Hits:
    705
  15. Tags
    Summary

    Dean Winchester has a bedwetting problem. Castiel has a solution.

    Language:
    English
    Words:
    17,873
    Chapters:
    7/?
    Comments:
    5
    Kudos:
    116
    Bookmarks:
    13
    Hits:
    3149
  16. Tags
    Summary

    Dean has messed up, big time. John, worried for his safety and his capabilities to handle hunting, decides on a fitting punishment: Dean is no longer to be an adult, but rather, he is to be a baby, John's baby, until he is ready to act like the responsible little soldier John knows he is.

    Language:
    English
    Words:
    35,507
    Chapters:
    14/?
    Comments:
    194
    Kudos:
    584
    Bookmarks:
    92
    Hits:
    22923
  17. Tags
    Summary

    I had another prompt idea. When you have the chance to write it of course. Definitely no pressure. I was just....what about a story where Sam makes a picture with fingerpaint, and it;s the messiest glitter/sticker covered mess ever...but Sam says it;s for Dean and that it’s Baby, the toy car Dean plays with all the time. And Dean loves it and Cas puts it on the fridge? :D --- anon from tumblr

    ** This was adorable, as usual. I'm so obsessed with these little fics. Stay tuned, because I'm working on a special project with Sam/Dean nestlings that I think you'll all (hopefully) love as much as I already am!!

    Series
    Language:
    English
    Words:
    1,154
    Chapters:
    1/1
    Comments:
    8
    Kudos:
    60
    Bookmarks:
    7
    Hits:
    829
  18. Tags
    Summary

    "Do you do prompts still? Your last one with baby Sammy was so cute, I’d love to see you write more! How about one where Sammy is playing hide and seek with Dean and he hides in the closet...but the door accidentally locks behind him. So he’s scared that he’ll be stuck in the closet forever, because he’s so small and such a good hider. But then Dean hears him crying and gets him out and “saves his little infant brother”! - anon prompt from tumblr <3

    -- Dean 3-4, pull-ups still mostly, Sammy 1-2, still in diapers

    Series
    Language:
    English
    Words:
    1,720
    Chapters:
    1/1
    Comments:
    9
    Kudos:
    79
    Bookmarks:
    10
    Hits:
    1381
  19. Tags
    Summary

    Prompt: Cas loses dean at the playground/park by their condo, so it’s pretty private. Cas is the caregiver. Dean is the little. Dean just calls him “papa”. Comfortable with anything, diapers, bottles, anything honestly. Cas is ready a book, Dean sees a squirrel or something so he walks away and follows it until Cas looks up and panics. I do want the ending to be Cas getting angry with Dean because he left and dean cries, but Cas comforts him later.

    I hope that’s not too complicated

    Series
    Language:
    English
    Words:
    967
    Chapters:
    1/1
    Comments:
    2
    Kudos:
    27
    Bookmarks:
    1
    Hits:
    768
  20. Tags
    Summary

    "Not sure whether this prompt is something you’d take up, but what about Dean needing a booster shot for something? Maybe Meg could administer it, as she’s done some nursing, and daddy Cas has to calm our little boy down." -Rachaelzi

    Thank you so much Rachaelzi for this lovely prompt. Sad little Dean hurt my soul, so I made sure his daddy made him feel lots better after <3 Enjoy (:

    Series
    Language:
    English
    Words:
    1,706
    Chapters:
    1/1
    Comments:
    6
    Kudos:
    68
    Bookmarks:
    7
    Hits:
    1255

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