Posted originally on the Archive_of_Our_Own at https://archiveofourown.org/
works/4050439.
  Rating:
      Explicit
  Archive Warning:
      Underage
  Category:
      M/M
  Fandom:
      Supernatural
  Relationship:
      Dean_Winchester/Sam_Winchester
  Character:
      Mary_Winchester, Anna_Milton
  Additional Tags:
      Age_Difference, Older_Man/Younger_Man, Old_Man_Dean, Young_Twink_Sam,
      Incest, unknown_incest, Voyeurism, Voyeur_Dean, Dirty_Talk
  Collections:
      Weecest
  Stats:
      Published: 2015-06-01 Words: 3622
****** Neighbourly ******
by Miss_Lv
Summary
     Kink Meme: Older Dean fucks a teenage but of legal age Sam, with
     emphasis on age difference.
Notes
     So Sam is seventeen in this, just a fyi.
     Also this is straight up porn.
See the end of the work for more notes
Mr. Winchester had lived across the fence from their house since Sam was a baby
since his mom was young even. Both their families had owned their houses for
six or seven generations.
“He’s a nice enough old man if a bit of a perv,” his mom would say lightly and
his dad would chuckle. It was well known that Mr. Winchester had been a bit of
a bad boy and chased all the girls around when he was younger. He had never
married, but he had lived with a variety of women over the years. Kids that
weren’t his had grown up in that house and they still came to visit; called Mr.
Winchester ‘dad’.
Plus everyone knew that the yoga instructor from the college had an affair with
Mr. Winchester ten years ago. Her son Ben looked nothing like her husband and
everything like Mr. Winchester.
There were a lot of rumors about kids who looked like Mr. Winchester, about the
women who he’d messed around with.
But he was a charming man with a sly smile and an endless depth for kindness.
When the Mosely family had lost their house in a fire they had stayed at
Mr.Winchester’s place for six months and Sam remembered hearing the old man
refuse any sort of payment.
“I don’t want your damn money, let me do a good thing. Tell you what, when I’m
old and useless come visit me in whatever home I get shipped off too.”
Sam doubted Dean would lack visitors, the man was a horrid gossip, people were
constantly stopping at his porch, sitting with him and sharing the latest news
around down.
Sam was out pumping the tire of his bike once and he overheard the porch
gossip, his mom was leaning on the fence right in the thick of it with Mr.
Winchester and Miss Novak from down the street.
“Pregnant again, and the dad’s run off with the accountant! The male
accountant,” Miss Novak said it like it was dirty and Sam felt a familiar
weight in his chest when people spoke about homosexuality with that tone.
“Naomi, don’t be daft,” Mr. Winchester cut in with a stern tone. “I’d bet my
Impala that boy didn’t father that kid. No, he just needed to hide and she
needed someone to marry her without questions. Two idiots messing up. Least
he’s gotten himself figured out and she had her head held high when she walks
around town. No shame in a baby without a man, it’s not the 1950s anymore.”
Miss Novak had looked sour, but Sam’s mom had been nodding along.
“Still makes for good gossip though,” Mr. Winchester added and both women had
laughed. Mr. Winchester had a way with people, he could give you a talking too
and then sooth the sting of it with a smile and joke.
He was crafty but good-hearted so Sam never thought badly of him. No one in
their town did really, he was just another face everyone knew in the small
community.
But Sam knew things no one else did about Mr. Winchester, or they never talked
about anyway. Like how Sam saw men leaving by the back door just has often as
women. Or the way Mr. Winchester would watch him in the yard sometimes.
On sunny days, Sam’s mom would kick him out to get some sun so Sam usually
ended up their back deck reading. He’d sit in his mom’s patio chair and lazily
read through some book that had his current attention. He never dressed
inappropriate, shorts and t-shirt usually and sometimes he’d take the shirt off
if he got too hot. It was perfectly normal, but he never missed the way Mr.
Winchester would find a reason to be in his own yard. He usually had things he
needed help with too and Sam would end up working a sweat under the man’s gaze.
One time Mr. Winchester had just leaned against his doorframe and sipped a
beer, watching Sam bluntly.
It should have been creepy.
It was unsettling in a remote way, improper. Sam was seventeen and his old
neighbor was generations older than him.
But he never did or said anything truly wrong; the man would just look at Sam
with such a dark weight in his gaze. If made Sam want to squirm and it always
came back to him when he jerked off. He thought of the old man watching him and
some twisted part of him liked it. It made him feel good to know he was wanted
in such a base way. Sam felt like his body and looks had to be good to draw the
man’s eye every time. So while it was so utterly inappropriate Sam never said a
word, never tried to discourage the looks or hide from them. If anything he
might have even encouraged them a tiny bit, with weak smiles and flushed looks.
 
One summer day his mom and dad were out and Sam was prepared to lie out in the
sun. The first thing he did though was take a long shower with a thought jerk
off session. With his parents out Sam took a toy and worked himself open,
fucking his ass as he jerked off. He’d come to know his body well enough to
know he loved being fucked. Nothing felt quite as good as the stretch and
friction of something inside him. Unbidden the thought of Mr. Winchester
watching came to him and Sam shivered as his cock twitched and he got off.
Sucking in shaky breaths Sam watched his come wash down the drain.
Mr. Winchester was in his yard and he asked Sam to come help him dig up the
garden soil as soon as he saw him. Sam wondered idly if the man had been
waiting for him. Usually in the summer Sam found a reason to be out back when
his parents weren’t around.
“Needs to be turned over or nothing will grow good.”
Sam nodded his head and did the work, the old man settling on the back steps of
his house and watching him work. His ass was still open and slick and Sam tried
to ignore it, willing his cock to stay down. If felt tense again, that strange
thrill of being watched as he worked. Sam could feel the dirty intentions of
the man, but he said nothing, working to get the dirt loose with a shovel.
It was hot out and by the time he was done he was a sweaty mess. His cock was
half hard and Sam knew it would take a breeze to get him fully erect and
tenting his shorts.
“Come get a drink,” Mr. Winchester called and walked into his house. Sam
hesitated; there was no way this was about a simple drink. He saw the man
chopping wood last week so Sam doubted Mr. Winchester had really needed his
help at all. He had just wanted to watch Sam work and now he wanted him in his
house.
Sam could feel his dick filling out all the way, just the idea of it. Red faced
he ducked into the backdoor and followed the man.
Mr. Winchester had a glass of water waiting and Sam had to step close to him to
get it. Standing at the counter he picked up the glass and swallowed a few
gulps. Mr. Winchester watched this with an intense stare and when Sam set the
glass down he felt the man’s hand on his back, rubbing slow circles and
drifting low.
“How’s school been Sammy? Excited for the summer break?” He asked like
everything was perfectly normal. Sam swallowed nervously, fingers gripping the
edge of the counter as he struggled to answer.
“G-Good, its good. Summers…summer is good too.”
Before Sam could berate himself for sounding so dumb the older man gave a
chuckle and dropped his hand to cup Sam’s ass. His hand felt huge as he groped
Sam and the boy bit his lip but didn’t say anything. Red faced he let the older
man touch him as he felt his cock fill out in his shorts.
“Look at you all grown up,” Mr. Winchester teased as he reached around and
rubbed Sam’s cock. It wasn’t the first time anyone had touched him, Sam wasn’t
a virgin or anything but just the fact that is was Mr. Winchester made the
touch feel more intense.
Sam shivered but held still as the old man pushed his shorts down and cupped
his ass again, squeezing and kneading. Sam was facing the counter, hands braced
on the edge as Mr. Winchester stood beside him, facing Sam as he touched as he
pleased right there in the kitchen like it was nothing.
“Look at this ass, fucking perfect,” he muttered more to himself then Sam it
seemed as thick fingers pressed until they were rubbing against his asshole.
Sam swore, jerking as the man pressed his fingertip at his entrance.
“Pretty pink little thing,” Mr Winchester crooned and Sam felt his face burn.
Gripping the edge of the counter harder he bit his lips but stayed right were
he was, even spread his legs a little.
Mr Winchester’s finger slid in easily, Sam was still open and wet from his
shower fucking. There was still lube inside him and it slicked the way.
“Greedy hole,” the old man chuckled, sliding his finger back and forth. “Looks
like you nice and opened up for me huh?”
Sam couldn’t get his voice to work so he settled for a nod of his head.
“You like getting fingered?” Mr. Winchester asked as he slid a second in,
pressing two fingers into Sam’s ass. Against the boy could only nod his head as
the old man chuckled. He stepped closer to Sam his chest to Sam’s back and he
could feel the man’s erection rubbing on his ass.
His fingers worked smoothly, twisting and pumping as the man angled them and
made Sam jerk. Sucking in a shaky breath Sam tried not to whine out as the man
finger fucked him. Mr. Winchester was good at it too, he just seemed to know
the perfect way to shove into Sam.
“I’m gonna fuck your ass, ok baby boy?”
Sam managed a nod and the old man behind him chuckled that deep smoky tone
again. Sam could hear the zipper as Mr. Winchester got his cock out, didn’t
even undo his belt, just dropped the fly and got himself out.
He was going to fuck Sam, right there in his kitchen against a counter in broad
daylight. A man twice Sam’s age was going to pound his ass. Sam didn’t know why
but it really turned him on, just the idea of it.
Sam twisted his head to peer down at the Mr. Winchester’s cock, watching the
man give it a few strokes. He was hard and thick, not overly long but fat in a
way that Sam knew he was going to feel. Mr. Winchester took Sam’s hand from the
counter and wrapped his fingers around the heavy cock. It felt hot against his
palm and Sam shivered as he gave it a few weak pulls.
“Line me up,” Mr. Winchester said and stepped closer. Sam fumbled to obey,
leaning against the counter more to stick his ass out as he tried to get them
in position. He was trembling hard as the old man rest his hands on Sam’s
sides, rubbing him in soothing encouraging motions. Sam had never done anything
like this before. He was a good guy who never did anything so dirty. The only
sex he’d had before was locked in a bedroom in the dark of night, lights low.
The kitchen was bright and there were windows everywhere, the backdoor was open
with only the screen door to hide them. Sam could hear cars going by and
children playing.
It made his cock throb.
The thick head pressed against his wet hole and Sam whined as he pressed it
there, slowly easing it into himself as his body got used to the stretch and
burn of it. Sam pressed back inch by slow inch until he was fully seated. It
was bigger then his toys and throbbed in his ass. Probably the thickest he’d
ever had inside him. When Mr. Winchester shifted Sam jolted at the delicious
feeling of the cock moving inside him. The sensation of that always got to him.
“Easy baby, take it easy.” He rubbed Sam’s back like an animal, voice soothing
even as he rocked his hips a little. Sam whined at the feeling, the friction
inside him making his knees go weak.
Mr. Winchester moved gently at first, little swaying motions that eased into
longer strokes with more speed. Sam could feel the rough denim of the man’s
jeans touch his thighs when he was pulled back. The old man was fully dressed
while Sam stood naked; his shorts around his feet as he bent over the counter
and let the man fuck into him. Sam bounced on the dick and he felt the old
man’s hand run up his back, along the nobs of his spine.
“You feel amazing baby, a nice tight cunt.”
Sam’s face burned at the word, it made him feel filthy in the best way and he
jerked when the man’s hand reached to curl around Sam’s cock. No one had ever
dirty talked ot Sam before and he’d always thought it would sound ridiculous
but when Mr. Winchester spoke it made Sam shiver.
Mr. Winchester chuckled and leaned over Sam, licking his neck and shoulder as
he started shoving harder into Sam’s ass.
“You like that baby? Like getting your pretty cunt pounded?” He leered and Sam
whimpered. He could smell a heavy aftershave on the other man and just the
knowledge that the man was so much older then Sam made him shiver. Mr.
Winchester had to be in his fifties.
Sam could hear a faint slapping sound every time he fucked into him, the zipper
of the man’s pants poking Sam in a painful was that he sorta liked. He could
feel Mr. Winchester’s balls slapping up against his own and the hands on him
dug in a touch. Suddenly every sexual partner Sam had ever had before seemed
fumbling. The man worked Sam’s body with such a practiced ease, Sam couldn’t
get his brain to even think straight as he whined high in his throat.
Mr. Winchester straightened back up again, taking Sam’s hips in his hands and
starting to really slam into him, making Sam do most of the work as he was
bounced up and down.
Sam heard the familiar rev of his family’s car and he jerked, looking up and
over through the window, the position let him see his mom pull into the
driveway of their house. Sam jerked and tried to pull away but the old man on
him shoved him back down, using his weight to pin Sam to the counter as he
pounded into his ass.
It nearly made Sam eye’s cross. It was fucked up how good it felt.
Sam covered his own mouth to muffle any sound as the man behind him grunted
openly. The curtain of the window was blocking them but Sam could see the faint
outline of his mom and could hear her talking on the phone. The window was open
and a breeze made the curtain flutter. Sam could see peeks of his mom with her
back to him as she got grocery from the car, completely unaware that her son
was at the old neighbors house getting fucked.
Mr. Winchester didn’t notice Sam’s mom, fucking into him with a surprising
amount of force. He hammered into Sam’s ass as the boy bit his hand to keep
quite. He should say something but some dirty part inside him stopped his
voice. Instead he stood there bent over the kitchen counter as the old man
fucked him, his mom right there across the yard.
Mr. Winchester sank all the way in and grinded his hips making Sam shiver. When
the old man’s calloused hand reached to curl around Sam’s cock he whimpered.
The situation was too much for the boy to handle and he swallowed a moan as he
came. His come splattered on the counter side as Sam slumped down with a weak
shudder. It was by far his most intense climax ever.
The old man gave a few tight thrusts into him and then started a hard, fast
fuck. Sam could feel his own come on his thigh and lube from earlier dripping
out from Mr. Winchester fucking him. It was wet and warm and it felt
disgusting. Sam wanted to jerk off all over again.
The man rode his ass roughly, more harsh then before as he grunted under his
breath and just fucked into Sam. It felt like being used and Sam clawed at the
smooth counter as he was taken.
He felt the old man in him pulse once and Mr. Winchester gave a low groan as he
pressed deeply into Sam, coming inside him. It didn’t even occur to Sam to
protest.
Sam saw his mom turn and he froze as she walked to the house. The curtain hid
them thankfully but Sam’s heart was in his throat though.
When he glanced back Mr. Winchester grinned at him and Sam blinked in surprise,
the old man had known she was there!
He pulled out slowly, making Sam feel it as the cock in him came free with a
wet sound. Mr. Winchester stepped back and Sam immediately fumbled to get his
shorts from the floor back around his waist.
“This is our little secret right?” Mr. Winchester asked smoothly as he tucked
himself back into his jeans. “Right Sammy?”
Red faced, the boy nodded his head, no way was he telling anyone about what he
had done. What he had let this man do to him.
“Then maybe you could come around again next time your moms out?”
Sam’s face felt like it was on fire but he nodded his head jerkily. He already
knew he would, that he would let this old man do that to him again. He wanted
this man to fuck him all summer, to pound Sam with those sure steady strokes.
None of his boyfriends had ever fucked him that good. The idea of it happening
again made his spent cock twitch.
“Sam!” The call made him jolt, twisting to look at his mom who know stood on
the back porch looking for him.
“Go on now boy, tell your mom you came and helped me move some boxes in the
basement. Shower right away to get the smell of sex off ya too,” Mr. Winchester
directed and Sam nodded his head, nearly tripping over his own feet as he
rushed out the back door.
 
Dean gave a low satisfied smirk as the boy ran home, answering his mom’s calls
like an obedient boy. He had always wondered if there was anything of his mom’s
wild streak in the polite kid. Sam’s mom Mary had been a crazy child and then a
wild teenager. Dean was certain he’d lost a lot of his hearing just from her
stereo blasting all night. He also remembered the nights she’s sneak out her
window or sneak some boy in. Right at eighteen she had blown out of the quiet
town and Dean heard second hand stories of her outrageous adventures all over
the country.
Eventually she had come back and moved into her family home beside Dean. He had
fond memories of her lazing on his porch swing and talking about rock concerts
with him into the evening.
Dean had never said anything to anyone but one late night she had leaned
forward and pressed a warm kiss to his mouth. It had been tempting; Mary was a
beautiful girl after all. But the last thing she needed was a too old man
putting hands on her.
No, it wouldn’t have been right. Mary had her mama’s smile but her eyes were
Deans.
Anna had never spoken a word to anyone about it, she’d married some straight-
laced man when she found out and he’d raised Mary as his own.
But Dean knew the truth about who her father was and so he let Mary down gently
that night. Explained to her that she deserved far better then him and a few
years later she’d met a mechanic that was utterly smitten with her. They got
married right away and settled into a content life together.
They had little Sammy not long after.
Now Mary was one thing. The idea of her getting knocked up not knowing who Dean
was would be a too much of a violation, even for him. What more, Mary had been
looking for more then sex that night.
But Sammy was a young boy and he had grown up so pretty.
He was youthful enough that he didn’t even know what he wanted, much less whom.
He was wide eyed and still figuring himself out and he would move on
eventually. Dean would be a fond memory years down the road when Sammy settled
with some far off partner.
That was something Dean could live with.
And maybe he got a filthy little thrill, taking something so pure and innocent
and utterly taboo and dirtying it up a little.
Or a lot.
Dean leaned back on his porch swing and took a long drink of his beer. It was
going to be a good summer.
End Notes
     I wasn't going to make them related but in the end I could just see
     it, old man Dean perving on his secret grandson.
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