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Five Times Sam Was Topped

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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.