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Fandom: Supernatural
Pairings: Meg/Sam, Ruby/Sam, Jody/Sam, Abaddon/Sam, Castiel/Sam
Word Count: 4800
Alternate Link: AO3

Warnings/Kinks/Tags: Pegging, manhandling, rough sex, begging, crying, object insertion, some dub-con and some consensual sex, tentacles, humiliation, dirty talk, desperation, pain play, elements of D/s, aggression, sounding

Summary:  samanddeaninpanties answered a “top five dicks you’d like to see in Sam,” and it sounded like a to-do list.  So I did it.  Hope you like it 🙂

Five Times Sam Was Topped

He didn’t know she was a demon.  At least not
until he was on his back, legs in the air, and the hot blonde was
ramming into him so hard, fucking him so good that he didn’t even care
anymore when he saw the smirk, the eyes turn black.  Sam whimpers and
begs when she pins his wrists to the bed, but he’s not begging to be let
loose.

“Please let me come,” Sam says, eyes wide.  "Please, Meg.  Please!“

She’s
got him bent in half, and he knows he probably should’ve realized
something was wrong when a chick not even close to his weight class
shoved him back onto the bed and worked him open with his own bottle of
lube, shoved her way into him with his own strap-on.  She’d found it at
the bottom of his duffel.

And as the demon pours itself into him,
his orgasm making the whole thing so good it hurts, he begs her not to
tell Dean.  Because he’s fucked up.  He’s gotten soft in his time away
from his family, and he doesn’t want to see the look of disappointment
on Dean’s face when he realizes his little brother not only begged a
demon to fuck him, but that he’d do it all over again if he could.

*

It’s
Ruby’s mouth that does it.  She kisses him just a little too hard,
sucks hickeys into his skin a little too close to the line of his
clothing, and she licks his asshole just a little too long.

"Fuck
me!” Sam growls, on his hands and knees, spread wide for her.  The rough
cement under his knees hurts, but he doesn’t care.  "Just fuck me
already!“

Ruby chuckles.  "So impatient,” she says.

But
Sam’s had a good dose of blood, and he’s not ready to be teased.  He
wants to get fucked.  He spins around, the demon blood in him giving him strength and speed, which means he can catch her by surprise.
 She squeaks as he pounces, straddling her smaller body and lowering
himself down over the strap-on.

“Oh, fuck yeah,” he groans as he sinks down, eyes closing while he grabs a breast in each hand and squeezes.

He
doesn’t hesitate or let himself adjust to the fairly large dildo in his
ass.  He just starts fucking himself on her cock.  He doesn’t care if
she gets off.  He doesn’t even want to ask her if she’s having a good
time.  In fact the smirk on her face is annoying, so he leans down and
bites her shoulder.

“Fuck!” she yells, back arching as he breaks the skin and sucks.  "I already gave you some.“

"Want more,” Sam says, words muffled by her skin.  Then he’s hissing as she drags her nails down his back and over his sides.

She
takes advantage of his momentary distraction and pushes him off.  
Before he can recover, she’s on top of him, right hand grabbing a good
chunk of his hair and holding his head down to the floor while she
wrenches his left wrist up and behind his back.

“Yeah, fuck me,” Sam says as she slams back into him.

She
laughs, but she does as she’s told.  Sam tries to relax when she pushes
his wrist up even more.  If he makes a move, he’ll dislocate his own
shoulder.  It’s nothing he can’t handle, but it would be an
inconvenience, so he lets her do whatever she wants to him.

His
hard cock drags over the concrete below him, but it only makes him
harder.  She’s close, almost there.  He knows because of the way she’s
panting.  He’s fucked her and been fucked by her enough times to know
exactly what she sounds like when she’s about to come.

“Fuck,
Sam,” Ruby hisses, and then she’s coming, fucking him so hard he knows
he’s going to have some abrasions on the right side of his chin.

But
then he’s coming too, and the pain in his chin, the pain on the
underside of his cock just doesn’t matter at all when he’s screaming his
way through an orgasm, making a mess of the concrete and his stomach.

She pulls out of him and slaps his ass playfully.  "Next time you get to top,“ she says.

By
the time he gets to his knees and starts pulling his clothes back on,
she’s gone.  All he has left is the emptiness in his ass, the
uncomfortable stickiness of the lube drying on his ass cheeks, and a
nice thrum of power running through his veins.

It’s more than worth it.

*

He
doesn’t know her very well, and she’s eying him up like he’s some
hardened criminal even though Bobby put in a good word for him.  She’s
holding her nightstick, twirling it as she paces in front of the cell
she’s locked him in.  He’s standing in the middle of the cell, not
really upset over what’s happened.  He’d been snooping, and it wasn’t
the first time he’d been in a jail cell.

"Bobby says I should let you go,” Jody says.

She practically fondles the nightstick, hands running over it in a way that has Sam getting hard in his jeans.

“But,” she drawls, “I’m tired of haulin’ you two in here.  Apparently my last warning meant nothin’ to you.”

She
taps one of the bars of his cell with her nightstick once, twice, then
wraps her left hand around it, caressing it.  It’s distracting, and
Sam’s not even sure he wants her to let him go at this point.

“Sam?” she says.  "I’m talking to you.“

Sam
blushes, forcing himself to meet her glare.  She noticed.  She’s been
watching him and she saw him practically drooling over the fucking
nightstick.  He can see it in her eyes, the way she’s smirking, and by
the tilt of her head.

"Yes, ma’am,” Sam says, but he has no idea what he’s agreeing to.

“So you do think I should keep you in here ‘til Monday morning?” she asks, voice thick with sarcasm.

Sam
mentally kicks himself.  He must’ve been so focused on the stupid
fucking nightstick that he didn’t hear her question the first time.

“No,
ma’am,” he says, but he’s not even convincing to his own ears.  He’s
never been more grateful that Dean’s passed out drunk at Bobby’s,
drooling on the couch.

Jody taps the shaft of the nightstick on
the palm of her left hand, then wraps her fingers around it again.  This
time she’s not even trying to disguise the fact that she’s stroking it.
 He whimpers, blushing harder when he hears himself make such a needy
noise.

“Maybe I’m going about this wrong,” Jody says as she pulls
out her keys and unlocks the cell door, the creaking of the hinges
loud in the otherwise empty precinct.  "Maybe punishment is what works
best with your brother, but you need a reward system.“

Sam’s
nearly shivering now that she’s only about two feet away from him, still
caressing that nightstick as if it’s his cock.  Or maybe hers.

"Yes, ma’am,” he says politely, glancing back and forth between her too-intense gaze and her nightstick.

“I think a strip search is in order,” she says, then taps his belly with the end of the nightstick.

He’s
pulling his clothes off before she’s even done saying the words, and
when he drops down onto the cot, making the springs squeak, she
chuckles, obviously pleased by his enthusiasm.  He makes quick work of
getting his shoes and socks off, and scrambles back off the bed,
stepping out of his jeans and underwear, standing naked before her, cock
hard and leaking.

“Good boy,” Jody says as she runs the nightstick over his cock, a gentle touch that has Sam whimpering, his cock twitching.

“Please,” he says, and it sounds broken, desperate.

She likes it.  He knows she likes it because she smiles with approval, the nightstick running under his balls.

“Which
end are you beggin’ for, sweetheart?” she asks, holding the nightstick
up between them, letting him see the smoother, longer end of the stick,
caressing it before she switches hands, holding the longer end with her
left hand, letting him see the rippled handle with the mushroom head end
cap.

“Fuck,” he breathes.  He wants it in him.  He wants that
mushroom head, wants those ripples fucking into him.  He wants her to
fuck him with it.

She points toward the cot.  "On the bed, on your knees, legs spread, ass toward me.“

He’s
already climbing on the cot, getting into position, but he hears her
walking away, her boots receding.  He panics a little, wonders if this
was all a big joke and she’s going to leave him like this, alone and
horny while he pulls his clothes back on.

"Stay in position,” Jody barks.

Sam
chuckles, lowering his forehead to the bed and sticking his ass out
like she’d asked.  He doesn’t care that he’s leaking on her cot.  For
all he knows, he’s not the first to spread for her like this.  He hears
her rummaging around in a desk drawer, then she’s walking back into the
cell.

“Beautiful,” Jody says.

Sam flushes again, the
compliment making his cock twitch again.  His asshole clenches in
anticipation as she runs her hand over his left ass cheek.

“You ever been filled up before, Winchester?” she asks.

He opens his mouth to answer, then gasps when he feels a dry finger circle his hole.  "Y-yes, ma’am.“

"Did you like it?” she asks, and really she doesn’t need to.  Sam couldn’t be more obviously ecstatic about this.

“Yes, ma’am,” he says, voice shaky with arousal.

She
chuckles, a throaty sound that makes him shiver.  "Do you think you can
take me?“ she asks, tapping his ass with the end of the nightstick.

"Yes, ma’am,” he says, pushing his ass out even more.  "Please!“

He
makes some sort of noise that only comes out of dying animals when she
pushes two lubed fingers into his hole, fucking in and out roughly.  
He’s almost worried she’ll back off because really, that noise was
pretty ridiculous, but she must’ve realized it was a good dying-animal
noise.  She adds a third finger and taps his ass with the nightstick
again.

"Please, please, please,” he begs into the bed, wincing as he fights to stay in position.

She
pulls her fingers out, and he almost comes just listening to her slick
up the nightstick.  It’s wet and squelches, and he knows it’s going in
him, can’t wait.

“Please, ma’am,” he says.  "Please fuck me.“

"Oh, my, you’re so polite,” she says, rubbing the mushroom head over his hole.

He
tries to push back, but she just moves with him, the stick running over
and around and teasing and infuriating and frustrating and, “Oh, fuck,
yes!” he hisses as she pushes the handle into him.

It feels better
than he imagined it would.  It fills him, the mushroom head and ridges
making him squeak and almost fall out of position as she pushes it all
the way in, the hilt resting against his crease.

She doesn’t give him time to adjust.

“Fuck!
 Fuck!” he growls into the bed as she starts fucking him with the
nightstick, the mushroom head dragging over his prostate in a way that
has him babbling, begging, leaking on the bed.

It’s all over so
fast.  Too fast.  He’s coming, blowing his load on the bed and his
stomach, yelling nonsensical words without a care in the world that
anyone else might hear him, his asshole clenching around the nightstick.

He
hears her chuckle behind him.  That throaty laugh again.  It’s still
hot.  She pulls the nightstick out slowly.  It makes him gasp and squirm
now that he’s already come, his asshole used and sensitive.

“I’ll let you out in the morning,” she says, patting his ass and walking out of the cell.

By
the time he flops over, naked and spent on the cot, she’s locked the
cell and is heading for the desk.  She sits down and starts doing some
paperwork.  He doesn’t notice right away, but soon he sees the
nightstick on the cot next to him, still slick with the lube she’d used.
 He doesn’t know if it’s a promise for more of the same or just a
reminder of what she did to him.

Either way, he knows he’ll be getting in trouble fairly often whenever he’s in town.

*

Abaddon
has him by the throat, and all he can think is that he’s relieved she’s
going after him and not Dean.  He has no idea where Dean is, and he
hopes his brother is okay.

“Ow, fuck,” he whimpers as she slams
him down on a table, his legs sprawled out over the wood, his hands
grasping at her hand, trying to pull her off.  He likes rough sex, but
he also needs to breathe.

He’s naked, just out of the shower, and
he feels exposed on the wobbly motel room table, his torso the only
thing really supported by it, his ass half hanging off the end of it.

“Aww, did you change your mind?” she asks, face hovering inches from his own.

His
asshole clenches, his stomach almost sick, that feeling you get when
you’re falling and you don’t know when you’ll hit the bottom.  But his
cock is hard.  He knows what’s under her jeans.  Or at least he knows
what he’s read about.  He wants it.  Wants it inside him.

“No,” Sam says, voice strained.

“Ya look a little scared, Sammy-boy,” she teases, grinning.

“Didn’t expect to-,” he says, then coughs as she loosens the hold on his neck.  "Didn’t expect to lose the ability to breathe.“

She
lets out a cackle that makes his skin crawl, tipping her head back.  He
hears the zipper of her jeans, but both her hands are still on him.

"Oh, fuck,” he moans when he realizes every word he read about her is true.  And he can’t wait to see it.

The
Queen of Hell has many responsibilities.  One of which is to create
more demons than just the ones sent down to her.  A Knight of Hell is
always equipped to step up to the plate, taking their place as queen.

Something’s
touching his leg, slithering over it.  He flails, trying to sit up.  If
it’s going to be inside him, he wants to see it.  Prehensile.  He
remembers reading that.  But he hadn’t been able to find anything about
the size of the thing.

“Shit,” Sam says as his eyes widen.

The
main tentacle is about as big around as his wrist, but the seven, maybe
eight other tentacles are smaller, longer.  They’re all wet, all shiny
black, and he thinks he sees suction cups.  Nobody fucking said anything
about suction cups.

“Oh, fuck, wait!” he says, scrambling a bit,
panicking as he realizes the vulnerable position he’s put himself into.
He wanted it, but now that he has it, he’s not so sure he wants it
anymore.  And the gleam in her eyes says she can kill him without even
putting much effort into it.

“You’re not the endgame,” she says,
smirking at him as the tentacles slither over his legs, tickling his
balls and wrapping around his cock and poking at his hole.  "You’re just
a good time while I’m up top.“

It was meant to calm him down, and
it works.  She’s not going to kill him.  She’s just going to fuck him
with those things that are said to be addicting.  He doesn’t care if
they are.  He’s already a slut for any woman ready to fuck him in the
ass.  Abaddon is just another, slightly more kinky version of that.  He
just wonders if she’ll ruin him for other women.  Prehensile, his brain says over and over again.

She
lets go of his neck finally, her hands smoothing down his sides as she
nudges her way between his legs, grabbing his thighs and spreading him
for her.

"Ah, fuck,” he yelps as his back arches, the larger
tentacle pushing its way into his hole.  The other tentacles are rolling
his balls and jerking him off, making the whole thing easier to take,
but it’s still big, and she’s not giving him time to adjust.

It’s
tapered, and it’s lubed with something he really doesn’t want to think
about, but it feels amazing, hurts like a motherfucker, but he’s getting
filled, the odd not-quite-firmness of the thing inside him different
than anything he’s ever felt before.

He’s whimpering, loud and
pathetic, but he can’t stop himself, doesn’t even try.  His fingernails
are digging into the splintered wood of the table, back arching as he
tries to spread his legs more, spread himself open for her.

“What
the fuck!?” he hisses as the thing in his ass gets bigger.  No, it’s not
getting bigger.  It’s rippling.  Waves of pleasure as the thing moves
inside him, hitting his prostate just right.

He squeezes his eyes
shut, clenching his teeth as some of the tentacles wrap around his
balls, adding some pain to the mixture while the tentacles around his
cock speed up, stroking him like no hand ever could.

“Hey!” he
yelps, eyes opening as he tries to sit up, watching with no small amount
of panic as one of the tentacles pushes its way into his slit.

He
whimpers, the strange invasion only making the rest of what she’s doing
to him feel even better.  His head thunks back down onto the table.  He
moans, not even embarrassed that Abaddon sees him like this, not when
she’s doing whatever the fuck it is she’s doing to him.

“Oh, oh, oh,” he cries out as yet another tentacle presses on his taint.

He
feels himself floating, never having felt this much stimulation at once
before.  He realizes she really has ruined him for other women.  He’ll
worry about it later.

“Such a slutty little boy,” Abaddon teases, scratching her nails down his chest and stomach as she comes inside him.

He’s
not even thinking about the small paragraph he’d read.  He’s gone.  
He’s coming harder than he ever remembers coming, possibly screaming his
way through it, flailing on the table.  He hears the table creak and
doesn’t care if the thing breaks apart beneath him.

It’s over too
soon, but he’s still high on whatever endorphins all that stimulation
released.  It’s not enough to override the sensation of her pulling out,
the odd fullness remaining.  And that’s when he remembers that little
paragraph he’d read.

“Thanks for the fuck, Sam,” Abaddon says, smacking his leg before she heads for the door.

“Wait!”
Sam says, trying to get his limbs to obey him.  "How do I-?“ he starts,
but the door slams and he’s left alone.  "Fuck.  Fuck, fuck, fuck.  
Fuck!”

The table falls over as he’s flailing desperately,
tripping on his way to the bathroom and landing hard on his knees.  It
doesn’t slow him down.  He’s crawling so fast there may as well have
been a Hellhound after him.

Sam doesn’t know if it would work in a
human up top, but he’s not taking any chances.  He snags the gallon of
holy water he’d left in the bathroom, a long tube lying beside it, and
doesn’t waste any time cleaning himself out, trying to forget about the
word eggs.  He’s cleaning out come, nothing else.  She came inside him.
That’s it.  He’ll be okay.

It’s still worth it.

*

Sam
thinks Cas is adorable.  Especially when he looks so vulnerable.  Sam
doesn’t know how a creature as old or as powerful as Cas is could look
so fragile at times, but he does, and after he gets his grace back, he
doesn’t lose that lost look he had during his time as a human.  Sam
knows it’s because Cas’ wings are damaged, and Cas feels useless,
scared, alone because now he’s lost his friend and that person he had
the profound bond with to the influence of the Mark of Cain, to Hell.

Sam
really shouldn’t have pushed.  Shouldn’t have teased.  But he’s just so
angry.  At the world, at his brother, and at the forces or powers that
be who continually screw all of them over.  And over and over.

He
doesn’t even see Cas move, but suddenly the creature is snarling in his
face, holding him against the wall with powers that are more than just
physical.  Sam almost pisses himself.  Because he can feel it.  He can
feel that sense of something larger than what his eyes are telling him
he can see.  It’s never been directed at him before, and he’s terrified.
 He doesn’t even want to think about what this would feel like if Cas
was at full power.

“Is this what you wanted?” Cas hisses in his
face, giving him a little shake, which makes Sam’s head smack back into
the wall he’s pinned against.  His own fucking wall in his own fucking
bedroom.

Sam can’t make himself speak, and as Cas leans in closer,
letting out a sound that can only be called a growl that rumbles
through him, Sam finally loses the battle with his bladder.  He pisses
himself.  Warmth spreading over his crotch and down his legs.  It turns
cold much too quickly, and the way Cas’ lips twitch only adds to the
humiliation.

“Staying out of your head is a courtesy,” Cas says,
voice low, “one I offered to you and your brother because of everything
you’d done for the world.  Pushing me the way you’ve done over the past
few weeks?” says, then cocks his head to the side, “You no longer have
the privilege of privacy.”

Sam feels tears gather in the corners
of his eyes.  He’s so scared that he can’t even control the way his
bottom lip is quivering.  Cas is shorter than him, but he’s never felt
more overwhelmed, more surrounded by another individual.  He doesn’t
know what to say, what to do.  He’s teased, he’s pushed, he’s needled,
and this is what he’s gotten.  He deserves it, but that doesn’t mean
he’s going to be able to handle it.

He tries to remind himself
that Cas loves them, has fought by his side.  But Sam, of all people,
knows how far someone can go, how they can hurt someone they love.  
Especially when they’ve been pushed to their breaking point.

“You’ve manipulated,” Cas says.  "You’ve coerced and lied.“

Tears
run down his cheeks.  He knows exactly what Cas is talking about.  
Charlie. He’d hidden it from Dean, caused yet another death.  Cas blames
him.

"No,” Cas says, giving him another shake.  "You’re not
paying attention.  You’re assuming.  She made her own choices.  We all
hid it from Dean.  You’re no more to blame than the rest of us.“

He
can’t stop the tears, and soon he’s sobbing, heaving breaths that make
his chest ache, his eyes burn, and he feels like a rag doll hanging from
Cas’ hands, his energy drained.

"You’re still looking at life through the eyes of a victim,” Cas says.  "Stop.“

"I d-don’t know what you mean,” Sam says, sniffling as he blinks the tears from his eyes.

“All
of us are warriors,” Cas says, “and so was Charlie.  She didn’t need to
die the way she did, but she didn’t regret her decisions.  She died
trying to save Dean, and she gave us a key that even Rowena couldn’t
give us.  We’re not victims.  We’re warriors.  She should be honored as
such.”

But it’s his fault.  It’s his fault The Darkness has taken
over the world.  His fault cities are dark and Dean is running Hell with
the Mark burned into his arm yet again.  It’s his fault thousands of
people have died.  It’s his fault that he and Cas can only fight
hundreds of tiny wars instead of fixing the apocalypse he’s started.  
Again.

“You really think Dean’s down there torturing souls and earning black eyes?” Cas asks, lips twitching again.

Sam feels more tears run down his cheeks.  "It’s my fault.“

Cas lets out a huff of laughter.  "You know your brother better than that.  You know me
better than that.  The only one you don’t know is yourself.  You’re not
going to quit, and neither are we.  We never have before.”

“How
do you know?” Sam asks, because Cas can’t go to Hell in his condition.  
Fuck how well he thinks he knows Dean.  Cas doesn’t know what’s going on
down there.

“Crowley gave you that book,” Cas says.

Sam
looks over at the desk in the corner of his room.  His stomach nearly
rebels when he thinks about all the people who are enslaved, who can’t
have a home anymore, can’t have a desk of their own while he’s staying
in the bunker, everything just as nice and clean as it was before The
Darkness.  It’s a shock when he goes on a food run, seeing the
devastation out there, and it’s only by some miracle that millions or
possibly billions of people aren’t dead.  Maybe they’d be better off if
they were dead.  Living life as a zombie isn’t really living.

But
yes, the desk.  On top of it, open and waiting for him to finish it is
the book Crowley has given him.  He didn’t think much of it at the time,
and he still doesn’t really know why it’s so important.

“The binding on the book,” Cas says.

Sam nearly rolls his eyes.  Cas has him pinned against the wall.  He can’t see the binding.

“You already saw it,” Cas says.  "You know where it’s from.“

And
Sam does.  At least now he does.  Human hands didn’t make that book.  
It’s from Hell.  And if he just finishes it, figures out what Dean was
trying to tell him by using Crowley as his errand boy, maybe they can
save the world.

"But you were too distracted,” Cas says.  "You were reading through that book like it was a fairy tale.“

"I’m sorry,” Sam whispers.  He’s failed again.

“You
were distracted because you’ve been fighting The Darkness for three
years now,” Cas says.  "Nonstop, only eating and sleeping to keep
yourself fit for battle.  You haven’t smiled or laughed in all that
time.  You haven’t pleasured yourself.  You haven’t accepted the touch
of anyone in that time.“

Sam can’t look Cas in the eye anymore.  
It hurts.  Because it’s true.  He’s been focused on fixing everything
he’d fucked up, cutting out everything he didn’t deserve.  He lets out a
squeak as Cas leans in and kisses him.  It’s soft and gentle and
everything he doesn’t deserve.  It’s wrong and fucked up.  But he melts
against Cas all the same.

He doesn’t want gentle, but he kind of
does.  And as Cas spreads him out on the bed, Sam cries.  His brother
was right.  Sam Winchester cries during sex.  Especially when Cas kisses
every part of him like he’s precious, fingers moving over his skin
whisper soft, not leaving bruises or scratches behind.

And when
Cas pushes finally pushes into him, after Sam is a begging, shivering
mess, Cas’ cock fills him up in a way he hadn’t experienced since before
he’d doomed the world.  Sam lets him in, lets Cas take care of him,
lets Cas whisper words of love and devotion against his skin.  There’s
no aggression, no pain, no hurry to the end, and when he comes, Cas’
cock moving in and out of him slow and steady, Sam cries out into Cas’
mouth, arms wrapped around the smaller body, holding on for all he’s
worth.

When it’s over, Cas kisses his cheek, his forehead, his
neck, then his mouth again before giving him one last smile and walking
out of the room, leaving Sam to his research.  The book was never meant
for Cas.  Sam knows that now.  Cas wasn’t meant to figure this out, and
Dean knew exactly what he was doing when he sent Sam the book.

Sam
rolls out of bed and sits down at the desk, Cas’ release leaking from
his hole, but he doesn’t care that he’s possibly ruining the wood of the
chair.  There’s an answer somewhere in the pages of this book, and he’s
going to find it.  He’s a warrior, not a victim.  He’s going to fight.