Posted originally on the Archive_of_Our_Own at https://archiveofourown.org/
works/6819040.
  Rating:
      Explicit
  Archive Warning:
      Underage
  Category:
      F/M
  Fandom:
      Supernatural
  Relationship:
      Dean_Winchester/Mary_Winchester
  Character:
      Dean_Winchester, Mary_Winchester
  Additional Tags:
      Extremely_Underage, Vaginal_Fisting, Vaginal_Fingering, Hand_Jobs,
      Mother-Son_Relationship, Young_Dean_Winchester, Supernatural_Kink_Bingo
      2016
  Series:
      Part 1 of SPN_Kink_Bingo
  Stats:
      Published: 2016-05-11 Words: 2053
****** Eager to Please ******
by babybrotherdean
Summary
     Dean's always been a curious boy.
Notes
     Written for @spnkinkbingo. Filling my "fisting" square in the most
     sinful way possible.
     Enjoy the trip to Hell, everyone.
See the end of the work for more notes
If Mary’s little angel is anything, he’s a quick learner.
Eager to please also tops the list; from the very first time he asked to touch
her, Dean had wanted nothing more than to make her happy. Spreading her legs
that first time, just sitting back and allowing him to explore…
She misses John every day, but her little boy has become the light in her life,
and he seems entirely happy to fill every other empty role, as well.
She used to just let him do as he pleased. Dean’s always been a curious boy,
and there was something terribly arousing about the way he’d catch his lower
lip between his teeth while he learned his way around, a delicate wrinkle
between his brows as he concentrated. He’s always so serious, so worried about
doing well, and all Mary can think about are how soft his tiny fingers are
against her skin.
Now, though- now Mary has taken to teaching him. She shows him how to slip his
fingers inside her, how to curl and move them to make her feel good. Dean
blossoms under praise, beams at her and tries even harder like it’s his only
mission in life. These days, it might as well be. He does well in school, and
she’s doing her best to give him the childhood he deserves, but-
Well. Things are hard, sometimes, when they’re all they’ve got. Mary has lost
too much to allow Dean to slip through her fingers.
So it’s become habit. Dean will come home from school, and he’ll do his
homework, and Mary will make dinner for them both. They eat, and they talk, and
Dean smiles wide and excited when he tells her about his day, and Mary thinks
that she’s done absolutely nothing to deserve the beautiful, selfless, perfect
little boy she’s been graced with.
After dinner, though, and after Dean’s done his best to help her with the
dishes- he’s not quite tall enough to reach up to the high counter, but he does
his best and Mary lets him stand on a chair so he can do the drying- is always
her favourite time.
“Momma?” he’ll ask, all big green eyes and fingertips that catch in the hem of
her shirt, “can we cuddle?”
It’s the damn innocence that gets her every time, his honest, childlike
excitement that has her smiling so soft, reaching down to brush gentle
fingertips against freckled skin. “Yeah, baby,” she’ll tell him, savouring
every moment he spends with his eyes so lit up. “Let’s go to Mommy’s room.”
Her bed is infinitely more comfortable than the couch, and she’ll lead him
upstairs with her hand curled around the entirety of his, forever in awe at how
small he is. Dean hasn’t quite hit his growth spurt yet and Mary is more than
happy to cherish the time she has to love him just as he is like this.
Dean’s always the first to jump into bed, and this time is no different. He
climbs up and wiggles out of his shirt, then his socks, and finally his pants.
Mary’s already got his pyjamas ready for him because he’ll always stop here
before making it to his own room- if he even gets that far- and he’s old enough
now to get himself changed while Mary worries about herself for a few moments.
She hasn’t worn panties to bed in years, and will simply slip into one of her
soft nighties after dropping the rest of her clothes. Dean’s waiting for her by
the time she’s done, looking warm and soft in his Batman pyjamas and scrambling
to curl up to her as soon as she’s in bed.
He always starts beside her, but inevitably, he’ll start inching downwards-
Mary already has her legs spread, and he nestles himself between them like he
was made to be there, nudging her nightgown up gently until it bunches around
her waist and he’s left to rest his cheek against her bare thigh, humming
happily.
He’s told her in the past that this is his favourite way to be. Curled up
close, just the two of them. Mary worries that maybe he’s too attached to her,
too dependant- of all things to be concerned about in their relationship,
really- but always manages to convince herself that it’s okay. That without a
father or any siblings to cling to, it’s okay for Dean to attach himself to his
mother in every way he knows how.
If their way is a little abnormal- well, it’s a good thing that it’s their
special secret.
“Can I?” Dean asks, then, fingers already curled gently against her inner
thigh. Mary’s already wet, feels the way her clit aches for stimulation, but
she’s gotten very good at keeping her hands to herself while they do this- or,
at the very least, she’s learned to keep her hands off of herself. Dean’s a
very tactile child, and responds well to touch, and she isn’t about to take
that away from him. “Can I, Momma?”
“’Course you can, angel.” She reaches out to card her fingers through his hair
and he leans into her touch, eyes going half-lidded with pleasure. “Do whatever
you want.”
He opens his eyes against just to smile at her, but then he’s off to work,
focusing hard down between her legs. Mary spreads them a little wider out of
habit and just watches with bated breath as he moves in.
He starts with his fingers, like always. Spreads her apart carefully like he’s
afraid to hurt her or do something wrong and Mary can only watch, can only feel
that first tentative stroke that dips inside and let her eyes flutter shut as
she exhales sharply. Dean’s gentle, fingertips stroking along the insides of
her lips and she knows he wants to be good. Wants to learn the best way to do
this and there’s nothing better than her baby boy trying to understand.
Mary’s quivering, doing everything she can to stay still. It’s hard not to
press closer, to lift her hips and encourage Dean to keep going, but she
manages. She doesn’t want to take his control away, even if that just means
sitting back and letting him do as he pleases. When he finally presses one
finger into her, barely long enough to tickle, she tips her head back and
breathes out her first real moan, toes curling lightly with the sensation.
It’s easy after that, something they’ve practised a million times. Dean slowly
adds more of his fingers, glancing up at her for approval along the way while
Mary pants softly and encourages him, whispering praise and running her hands
over his head, carding through baby-soft hair. He’s focused, worrying his plump
lower lip between his teeth and, several minutes after starting, leaning in
close to give her tiny, tentative kitten licks. His tongue is maybe even better
than his fingers, the way he’ll tease over her clit without really meaning to,
working little sighs and hitches of breath out of her that just drive him to
work even harder.
Mary’s lost count of how many fingers Dean’s using- he usually stops at three
and works from there- but when he looks up at her with big eyes and asks, in a
soft, entirely too excited voice, “can I keep going?” she has to stop and check
and. And oh.
Dean’s lifted his head a little bit, so it’s easy enough for her to sit up and
see the way he’s got his hand curled where his fingers disappear inside her.
The three usual fingers, his pinkie, and- and he’s got his thumb pressed flat
to the palm of his hand, waiting and expectant, and this is something she
hasn’t even really allowed herself to fantasize about before.
But Dean’s waiting for an answer, and Mary can’t so much as try to deny how
much wetter she’s getting just imagining it. “Yeah,” she replies, voice a
little too breathy and cracked. “Yeah, you- of course you can, sweetheat. Go
ahead.”
He smiles at her again like she’s just told him she’s making pie for dessert,
then looks down to focus once more. Mary watches, too, completely rapt as he
starts pushing in a little deeper. Watches as his knuckles slowly breach her
cunt, feels the way he’s stretching her open wider than he ever has on just his
fingers- thinks maybe, for one terrible, exhilarating second, that it’s maybe
just as wide as John used to get her on his cock alone- before it’s his thumb
slipping inside, too, the widest part of his hand insider her and he doesn’t
stop.
By the time he’s wrist-deep, Mary feels like she can’t breathe, can barely see
straight in the midst of her arousal. Doesn’t really realize she’s staring,
lips parted and entirely speechless, until Dean speaks up, sounding nervous.
“Is it… is it okay, Momma?”
She doesn’t allow herself to hesitate this time, nods quickly and cups his
cheek in her hand, the pad of her thumb sweeping over his skin. “It’s perfect,
baby,” she tells him, a sense of awe in her voice that she doesn’t try to
disguise. “Could you- could you try moving your fingers? Like you’re rubbing
them against something.”
So Dean nods and smiles and does just exactly what she’s asked, and it’s
goddamn perfect, has Mary moaning again and bringing a hand up to try to stifle
herself, feeling her orgasm built tight and warm at the base of her stomach.
Dean just works harder as a result, though, and when he leans in to lick gently
at her again, eyes on her face and seeking approval- she's done.
Mary comes like she always does, thighs clamping tight around Dean’s arm and
fingers catching in his pyjamas, holding him tight while she rides it out,
gasping out his name and his father’s in a mess that ends up less than
coherent. It’s hot and dizzy and she doesn’t know how long it lasts, but when
she finally relaxes her grip and Dean can pull his hand free, it only takes a
moment before he’s crawling up alongside her, snuggling into the curve of her
body while she tries to catch her breath.
“Did I do good?” he asks her anxiously, the way he always does, and Mary’s hit
all over again with how much she doesn’t deserve her beautiful little boy. “Did
you feel nice, Momma?”
Mary can feel him where he’s settled against her, pyjamas tented with an
erection that he’s too young to really know what to do with. She wraps her arms
around her son and pulls him close, peppers his cheeks with kisses. Smiles when
he giggles and squirms around. “You did perfect, Dean. Always got a surprise
for me, huh?”
He’s still smiling, cheeks pink and soft and shy when she lets her hand slip
down the front of his pyjama bottoms, and he doesn’t so much as question her
before she’s wrapping her fingers around his little dick. He does make sounds
for her, though- little whines, hitches of breath, moans that sound excited and
confused all rolled into one and shouldn’t be nearly as beautiful as they are
to her ears.
Dean’s not built to last, and he shudders to completion within seconds,
shivering with oversensitivity as she keeps her hand there, fingertips rubbing
gently into his softening cock. Thinks maybe she can train him a little better
like this, to last longer and teach him how to let her make him feel good for a
change, but for now, orgasms are purely a reward and she’s happy to let them
stay that way.
By the time he’s finished, Dean’s eyelids are drooping, and Mary knows he won’t
make it back to his own room tonight. She gets them both underneath the covers
without a word, lets Dean cuddle up to her side and cling to her while she
reaches out to turn off the light.
“Goodnight, little angel,” she whispers, and Dean’s already drifting, his
fingertips loosening their grip in her nightie. “Sleep well.”
They have lots and lots of time to learn, and Dean already knows so much.
There’s no telling how much more she’ll be able to teach him.
End Notes
     Welcome to Hell.
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