SPN Rare Ship CC: Round 21 | rosemoonweaver vs. @tobythewise
Prompt: Cock Warming
Ship: Sam/Jimmy/Eileen
Word Count: 4,458
Tags/Warnings: First Time Threesome, Cockwarming, Pegging, Cunnilingus, Anal Sex, Bottom Jimmy, Top Sam, Top Eileen, Implied/Referenced Incest, Referenced Dean/Cas/Jimmy, Implications of Wincest, Vaginal Sex, Polyamory
Summary: Sam’s been lusting after Jimmy for awhile. After a lot of talking and some gentle shoving by Eileen, the three of them are finally going to take the plunge and see if they’ve got sexual chemistry. 
AO3 Link

“You’re nervous,” Eileen says, running her hand up and down Sam’s chest.

“A little,” Sam says. There isn’t any use in denying it, but honestly who could blame him? He is going to sleep with his brother’s boyfriend for the first time, of course, it’s nerve-wracking.

It all started at the Halloween party the year prior, when Cas, Dean, and Jimmy showed up as Superman, Batman, and Wonder Woman respectively. Cas was smartly attractive, as always, Dean looked like a giant kid and Jimmy… Sam had never seen Jimmy in anything other than tight blue jeans and thin shirts which were bad enough but in a skirt? Good god, that man has incredible thighs. Though Sam feigned irritation, the sight of James Novak in that tiny skirt and corset, flaunting his fucking legs and acting as unapologetically femme as he apparently was left Sam drooling and remembering all that terrifying “experimentation” from college.

While Sam was having his own mini-crisis, Eileen was as cool as a cucumber. She’d never been shy about her sexuality or about announcing that she found both Winchester and Novak brothers attractive. “I’m deaf, not blind,” she’d say. In fact, that’s exactly what she said when she called Sam out on his own attraction to Jimmy (and Castiel, but that was a different matter for a different day).

It was an awkward process after that. Sam didn’t want to perv but he definitely was more aware of Jimmy’s ass and thighs and biceps and smile and basically everything else about him whenever they all hung out. Eileen not only noticed but started making comments – though mostly in sign or when the both of them were alone – and Sam was faced with accepting the reality that he was hopelessly gone on his brother’s boyfriend. Which would be humiliating enough, but the reality that Jimmy was polyamorous meant maybe there could be a chance for something to happen. But Sam sure as hell wasn’t going to ask. He wasn’t going to make it weird and seem like he thought anyone who was in a polyamorous relationship was DTF whenever wherever. Of course, Eileen had no issue with asking. Thank whoever oversaw the universe that she was at least gracious about it, asking in terms of what kind of polyamory Dean, Cas and Jimmy operated under and whether or not they’d even considered dating outside their three-person couple.

Sam learned two things that day: one, the Novak twins were way closer than he’d originally thought, and two, Jimmy was definitely DTF whenever wherever.

So that leaves Sam where he currently is, five months post-Jimmy Novak, Princess of Themiscara and his Thights of Sexual Reawakening, waiting in the kitchen for the first of what may eventually be many, many play sessions.

“It’ll be fine,” Eileen says, leaning up to give him a kiss on the cheek. “It’s just sex.”

“Is it though?” Sam asks. “It’s sex with my brother’s boyfriend.”

“And if it goes well tonight he might be our boyfriend,” Eileen says.

“Yeah, but -” Eileen cut him off with a finger to his lips.

“You’re overthinking this again. Jimmy likes you. Jimmy’s okay with this. So are Dean and Cas. There’s nothing to worry about. If this doesn’t go well and you don’t like it we’ll stop and watch movies and then laugh about it in six months,” she says.

Sam sighs against her finger. She’s right. He knows she’s right. But he really wants this to work.

There’s a knock at the door and Bones jumps up from where he was sitting under the table, trotting up to the front door with his tail wagging.

“Come in,” Sam shouts, “it’s unlocked.”

The door squeaks open, Jimmy’s face poking. Bones tries his best to squeeze through the opening and nearly topples Jimmy over, desperate to get kisses. Jimmy laughs, patting the dog and letting him lick his hand until his little doggy heart is content. “I wasn’t sure if you two were decent,” Jimmy says, coming in and shutting the door behind him, “I have a history of walking in on people who’ve started without me.”

Eileen walks up, giving Jimmy a hug and kiss on the cheek before shooing Bones off. “No, we haven’t started yet. I think Sam would like a quick refresher on the rules. He’s a bit nervous.”

“Why are you nervous?” Jimmy asked as Sam took his coat and hung it up.

Sam shrugs, trying to play it cool but knowing the frown on his face gives him away, “It’s just, a new thing is all. I haven’t exactly done this before.”

“I thought you and that guy… what was his name, Brady? Or something? Didn’t you have a thing with him in college?”

“Well yeah,” Sam says, “he was my… boyfriend, I guess. I’ve been with a guy before. But I’ve never done anything with more than one person at the same time.”

“Oh! Right. Well if it makes you feel better it’s basically the same as having sex with one person just with more hands and tongues and places to touch. And quicker refractory, if you do it right.”

Sam snorts, rolling his eyes.

“It’ll be fine,” Eileen says, rubbing Sam’s shoulders. “Besides, we’re taking turns. It’s not like you have to pay attention to everyone at once.”

“You’re right, I’m just -” Sam doesn’t get a chance to finish his worrying before Jimmy is leaning up and kissing him. Jimmy’s lips are soft and warm and the contact sends a surprising little tingle up Sam’s spine. Jimmy’s hand comes up, over his shoulder, to thread through Sam’s hair at the base of his skull. Jimmy’s tongue teases at Sam’s lips, just barely enough to make Sam open up before he retreats, going back to laying soft, closed mouth kisses to Sam’s lips.

They pull apart after a moment, both breathing just a little slower. “Sorry,” Jimmy says, “you were in your own head so I figured…”

“That’s – uh – yeah, that’s okay,” Sam stutters, resting his hands on Jimmy’s hips. Jimmy smiles, leaning up to kiss him again. Now that Sam’s more aware of it, he takes more initiative sucking Jimmy’s lip into his mouth when Jimmy teases with his tongue. Jimmy groans, pressing closer and tugging Sam’s hair just a little. Sam leans in, pressing his hips against Jimmy’s stomach.

“Okay,” Eileen says, pushing them apart. “That’s enough for out here,” she hooks Jimmy’s arm with her own and leads him toward the bedroom. He pouts, just a little, and Sam can’t help but think it’s adorable.

Eileen directs Jimmy to stand by the bed while Sam walks over to the leather chair in their reading nook. “You,” she says, point to Sam, “strip.” She then walks over to Jimmy and starts undoing his belt. “You remember how to tell me to stop?” She’s staring him directly in the eye as she undoes his pants like she sometimes does with Sam. Needless to say, it’s just as hot watching as it is on the other end of her steady gaze.

“Yup,” Jimmy says, “tap your thigh twice if I need you to slow down, three times for stop.”

“Or?” Eileen asks, whipping his leather belt out of the loops.

“Or get Sam’s attention so he can tell you.”

“Good boy,” Eileen says, leaning in to give him a quick kiss. Jimmy, however, isn’t satisfied with that and chases her lips as she pulls away. Eileen fists a hand in the back of his hair, tugging sharp enough to make Jimmy hiss. “Did I say you could do that?” She asks.

“No, but I -”

“No, what?” Eileen asks.

“No, ma’am.”

“If you want kisses you need to ask for it,” Eileen says. Her voice is hard and serious, but she’s smiling. It only just takes away from the tone she’s going of, but perhaps that’s because Sam finds it endearing. Eileen’s tough as nails and downright scary when she wants to be, but she’s never been very good at bossing Sam around in the bedroom. She’s aggressive, sure, but the few times they’ve attempted roleplay she always winds up giggling and calling it off.

“May I kiss you, ma’am?” Jimmy asks, completely serious, and Sam definitely takes notice of it. Eileen’s not one to be told what to do in the bedroom, but maybe Jimmy is.

“You may,” she says, releasing her hold on his hair. Jimmy bends forward, kissing Eileen on the lips. He takes his time, teasing her the same way he’d attempted to tease Sam, but Eileen doesn’t put up with it either. She gives back just as good as she gets, taunting by pulling back with a smile on her lips and mischief in her eyes. She laughs as Jimmy growls, sinking his hands into her hair and holding on as dives in. Eileen moans, clutching Jimmy’s waist as he leans her back and off balance. A hot spike of envy stirs in Sam’s chest but he’s not exactly who it’s for. He loves the way Eileen digs her nails into his skin, the same way she’s doing to Jimmy right now, but he’s not sure if he wants that more than the way Jimmy’s teeth are scraping against her bottom lip. It’s definitely making taking off his jeans more exciting.

Jimmy finally pulls off, smirking just a little as Eileen flushes. She shakes herself out of it quickly, pulling Jimmy’s top off before ordering him to shimmy out of his jeans and underwear. She and Sam both take him in at the same time. He’s been holding out on them, really. His abs are flat but there’s definitely power in his build. His arms seem a lot bigger, now that they’re not covered, and his cock has already perked up, thick and ready to play. Sam licks his lips and doesn’t miss the way Eileen does the same. Sam hurries to strip the last of his clothes off until he too is stark naked. His cock is, whether fortunately or unfortunately, not fully alert yet.

Eileen doesn’t touch Jimmy. Instead, she makes her way over to Sam. “Sit,” she says, pointing at the leather chair. Sam plops down, legs spread as he gets comfortable. She leans over him, giving him a quick kiss.

“Jimmy, on your knees,” she points to the ottoman in front of Sam, kicking it just enough that it’s flush with the chair.

It takes a little adjusting and some unfortunate squeaking on the part of the leather, but Jimmy manages to maneuver so he’s on his knees, elbows resting on the leather right in front of Sam’s balls, face in Sam’s crotch.

“Take him in your mouth,” she says, making her way to the dresser. She whips her top off, tossing it across the room and almost making it to the hamper.

Jimmy does and Sam has to prevent himself from jumping. It feels odd, having his dick in someone’s mouth when he isn’t even hard. Not weird in a bad way, just not something he’s used to.

By the dresser, Eileen is putting her hair up and stripping down. “Sam? We agreed on the purple one, right?” She asks, opening their toy drawer and pulling the harness out.

“Yeah, my favorite one,” Sam says.

Jimmy catches his eye, one eyebrow raised in question.

“Dude, did you think she was going to suggest pegging you if she didn’t already have a dildo to do it with?”

Jimmy shrugs, careful not to jostle too much.

Eileen strips down to her panties, buckling herself into the black harness Sam had gotten her as an anniversary present. The purple dildo wasn’t as thick or as long as Sam himself, but he liked the bumps and ridges much more than the bigger ones they’d tried.

She comes up behind Jimmy, lube in hand. She coats the dildo as she continues to speak. “I’ll fuck you as long as Sam stays soft. Once he’s hard your time is up.” She trails her wet fingers down Jimmy’s spine. He shudders, whimpering just enough for Sam to feel it against his cock. “I’d advise you not to make too much noise,” she says, “I don’t mind it, but Sam likes it, a lot.”

Jimmy glares up at Sam as Eileen’s fingers trail down between his ass cheeks. “You prepped already?” She asks.

Jimmy throws a thumbs up behind his head, losing his balance enough that the head of Sam’s cock bumps against the inside of his cheek. It’s very nice.

“I’m just going to make sure it’s enough,” she says, and Sam doesn’t need to see what happens because he can see it in Jimmy’s eyes and the way he’s struggling not to make any noise. Eileen’s wrist moves a few times, just out of Sam’s line of sight, so he focuses on Jimmy instead. Jimmy’s eyelids flutter and his breath comes hot and slow out of his nose, tickling Sam’s belly.

Eileen then stands straight up, lining her hips up with Jimmy’s ass. She pushes forward and Jimmy can’t resist making noise this time. His groan vibrates over Sam’s cock, tingling the skin where Jimmy’s lips are sealed around it. Fuck, it feels good. Sam’s not going to be able to hold off on getting hard if this keeps up.

Eileen gives Jimmy a moment to adjust before Sam nods at her to continue. She rolls her hips fluidly, her breasts bouncing as she does. God, she looks great like this. Sam’s usually on his hands and knees when she’s got the strap-on on so he never gets to see her breasts bounce or the way she huffs on harder thrusts. He usually just gets to feel it. Now, that he gets to see the way she moves and how her cheeks color, he wants to see it as often as possible. Maybe next time he can convince her to fuck him while he’s on his back. His thighs and ass tingle with the thought.

Jimmy moans between his legs again, eyes rolling. His fists clench in front of him, and Sam can tell he wants to wail. He’s making frustrated little noises around Sam’s cock, and Sam is definitely stiffening. Poor Jimmy keeps trying to hold it in, but it just isn’t working for him. He’s holding his breath but every few thrusts he has to breathe more again, which makes him dribble spit out of the corners of his mouth. Sam bites his lip and closes his eyes, desperate to keep his mind off how good it feels and how beautiful Eileen is and how delicious Jimmy looks making a mess on his cock. He thinks about doing taxes, about how much he can write off this year and whether or not he should file this week or next, but it quickly devolves into Jimmy wearing sexy Clark Kent glasses while blowing him. He scrambles in his own mind, trying to think of any of the supposed boner-killers he’s heard work. But his mind doesn’t want to focus on puppies or kittens or taxes or sports. He tries thinking about his grandmother, but he never knew his grandmother, so all his brain does is drop Dean into his little fantasy space. Dean, who’s now fucking Jimmy as Jimmy blows Sam.

Sam groans, eyes shooting open. That’s it. He gives up. He’s going to get hard and ruin Jimmy’s fun. Eileen catches his eye, as she leans forward, digging her nails into Jimmy’s shoulders.

“You okay, Sam?” She asks. She’s breathing a lot harder now, too and her lip is red from being bitten.

“Yeah, just,” Sam gestures to his lap. He’s hard now. Jimmy’s lips are still wrapped around his cock, though they’re about halfway up the shaft now instead of flush to the base. He’s also moving now, though subtle, in time with Eileen’s thrusts.

“Ah, too bad,” Eileen says, straightening back up and pulling out of Jimmy’s ass. “Looks like your time’s up, Jimmy,” she says, patting his ass.

Jimmy slides off Sam’s cock, slow and making sure to lip the tip as he pops off. He groans, his head pillowed against Sam’s thigh. “Dammit,” he huffs, his voice a little rough.

Eileen steps back, helping Jimmy back into a kneeling position. His cock is dripping precome and he’s made a little puddle on the black leather. He crawls off the ottoman, still on his knees in front of Eileen. “Goddamn,” he says, his voice soft, “Eileen, I don’t tell you enough, but you’re gorgeous,” his hand trails up her calf, knuckles brushing against the inside of her knee.

“You’re just saying that because you want to come,” she says.

Jimmy shakes his head, eyes wandering over her naked body. He looks a little dazed and Sam definitely can’t blame him. Eileen is gorgeous. She’s the most gorgeous woman he’s ever met. Jimmy’s right to be a little awed.

“Eileen,” Jimmy says,  hands on her hips. “Can I? Please? It’s been… so long. And you’re so beautiful. I want to. I need to.” He nuzzles his nose against her thigh, fingers playing with the buckle of her harness.

She nods. Jimmy sighs, “thank you,” as he undoes the buckle. He licks her thigh once before pulling the harness off her hips and letting it fall. He slips his fingers into the waistband of her panties and peels them back, slowly. His intake of breath makes Sam wish he could see the look in Jimmy’s eyes, but Sam had agreed that he’d stay still until Eileen told him otherwise, that way he wouldn’t be tied up.

Jimmy rises to his feet, a new kind of determination tensing his muscles. Eileen walks backward, falling onto the bed with her legs spread. Sam get the barest glimpse of her glistening pussy before she’s adjusting, laying out on the bed so Sam can get a side view of her body. Jimmy follows, dropping to the bed on his knees like a man possessed. His eyes are wild, his chest heaving, and he wastes no time settling down between Eileen’s legs. He starts by kissing Eileen’s tights, nuzzling his whole face against them, before he finally ducks down to taste her core. Eileen groans.

When they all discussed what they wanted to do for their first time together, Sam had been the one to suggest cock warming. Eileen had suggested pegging. It was Jimmy who, much too shyly in Sam’s opinion, asked if he could go down on Eileen. It had been easy to forget that once upon a time, Jimmy had been married to a woman. In between the loud, flamboyant personality, his doting over Dean, and constantly reminding everyone that he is really into guys, it would be easy to think Jimmy was just gay. He isn’t, though. And if the way he’s moaning between Eileen’s legs and humping the mattress was any indication, he enjoys giving pleasure to women just as much as he does men.

Eileen moans, pinching her nipple as Jimmy goes to town on her cunt. Sam can hear the slick slapping sounds of Jimmy’s fingers thrusting in and out of her, the wet sucking and slurping he makes as sucks and tongues at her clit. It’s hot as hell, just watching as Eileen loses herself and Jimmy tries to get deeper inside her. Her thighs tremble as she digs her ankles into Jimmy’s back, and Sam knows she’s close.  

Her hand fists in Jimmy’s hair as she pushes him closer, her hips bucking off the bed. Sam clenches and unclenches his fists. He wants so badly to join them or to touch himself but he said he wouldn’t. He’s hard enough to pound nails, though, and his dick keeps twitching and jumping every time Eileen calls out Jimmy’s name in that delicious wailing moan she has. He’s never come completely untouched, but if Jimmy keeps this up, he might able to do it.

Eileen nearly arches off the bed as she comes, half-screaming a jumble of syllables that make no sense. She’s breathing hard, by the time Jimmy pops up, his face glistening with her juices. “Did you like it?” He asks.

She rolls her eyes and kicks him with her heel. “Don’t ask stupid questions,” she breathes.

Jimmy licks his lips, sucking his fingers clean. “You are delicious,” he says. He turns to look at Sam, the slightest hint of worry his face. “Enjoy the show, big boy?”

Sam lets out a slow exhale. “You wanna found out?”

Jimmy’s eyes settle on Sam’s cock. “God, I really fuckin’ do.” He taps Eileen on the shin. “Can Sam come teach me a lesson for fucking his girl, now?” He asks.

Eileen laughs. “I’d be disappointed if he didn’t.”

Sam rises up from the chair, his legs a little stiff as he walks around the bed. He shoves Jimmy down on his back and crawls over top him without preamble. Jimmy spreading his legs eagerly.

“Hey,” Jimmy says, all humor and mirth absent from his voice as he stares at Sam’s chest and arms.

Sam kisses him, hard and deep, hopefully conveying just how wildly turned on he is. He can still taste Eileen on Jimmy’s tongue and it turns him on all that much more. Jimmy groans into the kiss, letting his hands run over Sam’s side and pushing at his ass to get him closer. Sam responds by lifting Jimmy’s leg up as he tips forward, wrapping Jimmy’s leg around his waist.

“I hope you’re ready for this because I’m not gonna be able to wait,” Sam says.

“Fuck yes,” Jimmy says, throwing his head back.

Sam wastes no time lining his cock up with Jimmy’s hole and sliding inside. He’s plenty wet from the earlier pegging, but Sam’s perfectly aware of how big he is.

Jimmy’s eyes roll back, his head falling against the pillow. “Fuck, dude. Warn a bitch. You’re huge.”

“I thought you were well aware of that fact,” Sam says, running his hands up Jimmy’s silky thighs. He must’ve been shaving or waxing since Halloween because he’s very soft and smooth.

“My mouth and my ass are two different things,” Jimmy says.

“Could’ve fooled me,” Sam says, pulling out just enough to snap back in sharply.

“Fuck!” Jimmy gasps.

Sam sets a punishing pace, egged on by Jimmy’s filthy mouth. He keeps moaning and swearing, practically begging for Sam to give it to him harder and faster. Sam, of course, complies, driving fast and hard. He can see Eileen out of the corner of his eye and past his hair, laying next to them and groaning as she plays with her clit. The noise of the two of them could be enough to send Sam hurtling over the edge, but he does his best to hold it off. Jimmy has to come first.

As if on cue, Jimmy starts fisting his own cock, his hand flying up and down the shaft. He’s muttering swears and please, head thrown back on the pillow. His back arches and his walls flutter around Sam’s cock and he spills over his own fist with a wail. Sam would love to stay inside him and ride out the delicious clench, but Eileen’s stuttering gasps let him know she’s close, too. Sam risks it, pulling out of Jimmy and shifting between Eileen’s legs. He slides inside, accomplishing three more thrusts before she’s also squeezing him tight and Sam’s crying out, emptying himself inside her.

Sam collapses between Eileen and Jimmy, breathing heavy. No one says anything for a long while, though they do wind up curled towards each other in the center of the bed.

“So, how was your first threesome?” Jimmy asks, pillowing his head on Sam’s shoulder.

“Wish I would’ve lasted longer,” Sam says.

Jimmy snorts. “Yeah, okay Mr. Perfectionist. I think you lasted plenty long.”

“There’s always next time,” Eileen says. She’s been sitting up, watching them as she waits for the movie to load on their TV.

“You want there to be a next time?” Sam asks.

“Don’t you?”

“Well, yeah. If Jimmy’s okay with it?”

Jimmy rolls his eyes. “No shit, dude. You’re hot. Eileen’s hot. I already hang out with you both a bunch so I know I like you.”

“You like us?” Sam asks.

“No, Sam, I hate your guts. That’s why I come over to play Settlers of Catan even though that game makes me want to skip rope on the open highway,” Jimmy says.

“That’s only because you always lose,” Eileen says.

“Well yeah,” Jimmy says, sitting up. “But seriously. I know you guys have your own relationship and I’ve got my thing with Dean and Cas and if you want this to be strictly sexual between the three of us that’s fine. But,” Jimmy lets out a breath, “I like you guys as friends, too. And if you want to more than that we can see where it goes, too.”

Sam smiles and the knot in his stomach finally unravels just a little bit. “Yeah okay, I’m okay with that. Eileen, are you okay with that?”

“Of course,” she says, hitting play on the movie.

The Star Wars theme blares to live as she settles down next to Sam.

“The Force Awakens? As an afterglow movie? God, you guys are nerds,” Jimmy says.

“Like I don’t know you live with the same guy who has all of Empire memorized,” Sam says.

Jimmy laughs. “So you’re saying the dork is strong with your family? Your brother has it and you have it, too?”

“Oh see now who’s quoting the trailer of the dork movie?”

“Never said I wasn’t a big dork, too. I was Wonder Woman for Halloween, remember?”

“Oh, I remember.”

“Maybe this year I’ll be Huttslayer Leia.”

“Oh god,” Sam groans, “I don’t know if I could handle that.”

“Yeah! We should do that! Let’s do Star Wars this year instead of superheroes!”

Sam shakes his head. “Well, I’m sure Dean would like being Han Solo,” Sam says.

“Oh, no, Cas would call Han. We used to fight about that as kids. He’s always Han. I was always Luke. Not anymore though! This year I’m donning a gold bikini.”

“And who should Sam be?” Eileen asks, “if you three are hogging all the original characters.”

Jimmy smirks, eyes drifting to the TV. “Kylo Ren.”

“What? Why?”

“Sexy shape. Sexy baritone voice. You got the hair for it,” Jimmy says.

Sam rolls his eyes. “That makes you being Leia weird, you know that, right?”

Jimmy laughs, “I’m not hearing a no.”

Sam glances at Eileen who’s no longer paying attention to either of them but watching the screen instead. “I’ll think about it.”