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Holiday Mixtape 2018, ProfoundBond Fic Recs, The Destiel Fan Survey Favs Collection
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2019-01-01
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A Simple Plan

Summary:

Cas and Dean have been driving Sam crazy for a decade with their pathetic mutual pining, so Sam's slightly manipulative sex party solution seems more than fair. Now it's just a matter of some shopping for supplies, and a bit of reverse psychology.

Notes:

Thanks to my wonderful beta, Blindswandive, the awesome people on my discord, and julia-sets, who suggested the pivotal ship.

**Don't Try This At Home:** Manipulating people into having sex is inappropriate in real life, even if they've been secretly pining for a decade and are driving you crazy. There are also brief comedic mentions of incest, though no one endorses it, and I make light of Dean's internalized homophobia for comedic effect.

(See the end of the work for more notes.)

Work Text:

"Mom?!" Dean hisses at Sam, from behind a display case of 19th century treatments for hysteria. "You invited Mom to the sex party?"

He rubs the back of his neck nervously and tries to disappear into the History of Vibrators exhibit like shopping with Sam at a sex toy store for their party supplies is the most scandalous thing he's done in his entire life. Which, considering he tortured people in Hell for a living, and he and Sam have almost destroyed the world multiple times and are chronically only a few bad calls on cases away from becoming serial killers, seems a little over-dramatic to Sam.

"Of course I invited Mom," Sam explains, as patiently as he can. It's been a long day of listening to Dean bitch about the crappy New England weather and the winding cow paths Massachusetts apparently mistook for roads back when it was a colony of King George and hasn't widened since. "We can't very well kick her and Bobby out of Donna's cabin so we can host a party there without her."

Sam realizes in retrospect he should've let Dean drive them back to the bunker before implementing this particular part of his Get Dean And Cas Laid (By Each Other) scheme. Dean would've been more comfortable there, and the planning would no doubt be going a lot smoother. But Fall River, where they'd killed the Yule cat that had been terrorizing people over lack of appropriately ugly Christmas sweaters, is a mere hundred miles from one of the best sex toy stores in the county. Since freeing Dean from Michael, Dean and Cas have been even more pathetic than usual in their mutually clueless pining, and Sam, quite frankly, is sick of it. He wanted to close the whole party deal as quickly as possible, and now here they are.

Dean inches closer to the door back out of Toys of Aphrodite, gazing longingly towards the slush-covered streets of downtown winter Provincetown.

"What part of not a tupperware party did you miss, Sam? You can't invite your own mother to an orgy," he complains. "That's incest." His lips sneer around the word 'incest' like he hasn't nailed both twins and triplets, and also confessed he thought 1970s Mom was a babe.

"Mom doesn't even like tupperware," Sam replies."And you're aware you don't have to personally bang everyone there just because you're the host, right? You don’t even have to be in the same room as her if it makes you uncomfortable."

Honestly, Dean looks uncomfortable already and they're not even in the same state as Mom. But if he thinks Sam hasn't been plenty uncomfortable himself, watching Dean and Cas make moony eyes at each other for ten years, he's got another think coming. There's a time for patience and letting things develop slowly, and that time was nine and a half years ago.

By the way," Sam says, as he skirts around Dean to get himself between his brother and the door to freedom, "did you know she got it on with Ketch? It'd probably be awkward if we invited him too, huh?"

Dean groans and pinches the bridge of his nose. "Gee thanks for burning that horrifying image into my brain forever. And yes, Sam, if you google the word 'awkward'; a picture of Ketch, AU Bobby, and Mom at our sex party is the top freaking result."

"At least he's not our Bobby," Sam says contemplatively. He picks up some strips of condoms in colorful foil squares, and holds them out to Dean. "Should we get the 'ribbed for her pleasure' ones, or just the regular?"

"Put those down!" Dean snatches the condoms out of his hand, and returns them to their display rack.

From the actual purchasable products part of the store that thus far Dean has been too cowardly to set foot into, an attractive heavy set woman wearing jeans and a black T-shirt with a rainbow Nike swoosh above the words "Just Do Her" approaches in that unnaturally friendly let me help you buy stuff way that salespeople have.

"Happy holidays. Can I help you guys with anything?" she asks. Her name tag reads Molly, and has a tiny rainbow unicorn decal on it.

"That'd be great," Sam replies. "We're hosting our first sex party, and we're not sure what supplies we should buy."

Behind him, Dean makes a horrible choking noise that Sam hopes wasn't loud enough for Molly to hear.

"Well," says Molly helpfully, "it's really up to you how much you want to supply and how much is BYO. Just be sure to communicate your expectations clearly to your guests beforehand."

Sam nods happily. This is basically research, and Sam loves research even when it's on tedious topics, which How to Throw a Sex Party and Get Dean Laid decidedly is not.

"I see you've found the condoms," she goes on. "Those are always a good bet. And some individual sized bottles of lube can also be a considerate amenity to have on hand."

She beckons Sam and Dean deeper into her store like the Vanna White of orgies, to a shelf of at least fifty kinds of personal lubricant. There are sampler bottles to try and hand-lettered recommendation signage from the staff.

She dabs a bit of oil on one wrist from a black and gold bottle marked Jill's Dessert- Apple Cinnamon Spice, and holds it towards Sam. It smells pretty good; authentically like cinnamon. Dean is still rather closer to the exhibit section of the store, where the door is, than the products part, where Sam and Molly are, but the promise of lube that smells like food entices him in.

"Holy crap," he exclaims, when she holds her wrist in the vicinity of his nose, "is that pie lube? It is, isn't it? Molly, you're an angel, and not the dicky kind either. Can I taste it?"

Sam is forced to kick him surreptitiously in the shin to get him to shut up, since he can't very well say she's a Lesbian, even your dumb but weirdly effective pick up lines won't get your tongue on her wrist. But Molly only beams at Dean like he complimented her first born child, calmly takes his hand, turns his arm so the inside of his wrist is face up, and dabs a little on.

Dean licks it back off.

"It is!" Dean says. His eyes sparkle with gratitude. "It's pie lube, Sam. Try some, dude, it's incredible!" He shoves his wrist at Sam's face like Sam might ever in a million years put his tongue anywhere near Dean's lube-slimy arm.

Molly shows off the rest of the flavors in the Jill's Dessert line to the sound of Dean's enthusiastic praise, while she quizzes them on the features they'd like their sex party to include. All male or mixed? Focused more on group sex or on pairing off?

Eventually Sam gets bored and wanders off to look at the bondage supplies. Maybe if he handcuffs Dean and Cas together they'll be forced to talk honestly to each other like in the movies. He gets bored with that idea pretty fast too though, because knowing them, Dean would spend the entire time silently convincing himself he's some kind of magic Cas poison, and Cas would spend the time convincing himself Dean is only using him for his mojo.

Sam sighs, and fishes in his jeans pocket instead, for the copy of the guest list Dean dictated to him while he drove here. It doesn't have many names on it, especially considering how many women Dean's slept with over the years, and while that works out well for Sam's matchmaking plans, it also tugs on his heartstrings in a way that makes him want to bang his head against the dressing room wall. It's not Sam's fault Dean is some god forsaken hybrid of a man-whore and a high school girl too shy to talk to her beau, so it hardly seems fair he should have to be the one to fix it.

In its entirety, Dean's guest list reads:

Jody
Donna
Claire
Dark Kaia
Alex
Patience
Charlie
Cas

Donna and Jody are currently dating. Claire and Charlie are Lesbians. Alex and Patience are too young. Also, everyone on there but Charlie is one big family, of which Dean is already sort of a part, so Sam suspects in addition to the other issues, they all go in the Incest Cooties category too.

Which leaves only Cas.

Dean is so transparent it's almost cute.

"Found something for you." Dean saunters over from the Erotic Fashion area, holding up a naughty maid lingerie set, complete with a purple feather duster for tickling purposes. He smells like apple pie. His new sex/dessert mentor is across the store helping another customer. She seems to have cured him of his fear of toy stores.

"Bet you'll look great in it, Sam. It'll help you get a date."

He holds it up to Sam's chest. Not surprisingly, it's about fifteen sizes too small.

"My dance card's full, as you'd know if you'd bothered to look at the names I added to the list. Good thing I put some on there for both of us; for an alleged sex god, you didn't have many picks."

Dean returns the maid outfit to the rack.

"Not alleged, Sammy, but fine, whatever." He grabs the list out of Sam's hand, and frowns as he reads down it. "Rowena? You think I should bone Rowena? No way in hell is that happening. She's a witch, Sam."

"Don't worry," Sam reassures him. He holds out the ten-inch green silicone dildo he's been eyeing. "With Rowena, you won't be doing the boning. Do you think she'd like this one better or the purple double-headed one?"

Dean rolls his eyes. "How would I know?- You're the fifth base expert, not me. And what's up with the rest of these suggestions? Garth? Really? He's a dude, Sam, so no."

Molly the Orgy Educator finishes up with her customer, and comes back over for a second round of Divest the Winchesters of Every Non-Credit Card Fraud-Related Penny They Have, so that saves Sam from having to deal with Dean's insistence that he won't date men. They end up buying condoms and lube as practical gifts, plus lipstick-shaped vibrators for the women, and glow-in-the-dark cock rings for the men. Molly said outright they don't need all that stuff, but she's such a good salesperson he buys it all anyway.

He carries everything to the register, and Dean rejects people at him while Molly rings up their purchases.

"Max Banes: dude, and a witch too. No way. Jesse and Cesar: double no. Dudes, and they're also freaking married, man. Walt...

Wait; you mean like Walt-and-Roy Walt? Oh come on, Sam, he killed you! That's just pathetic."

"He killed you too, Dean,” Sam points out. “But he's been sad since Roy died. I thought it'd be a nice gesture."

"Banging someone is not a gesture! Also, why are there so many dudes on your list?"

Sam shrugs. "Why are there so many Lesbians on yours?"

Molly bags up their purchases in hot pink tissue paper inside a high-end black bag with the store's logo emblazoned boldly in red. Her lips quirk up at the corners, and Sam thinks she might be laughing at him and Dean on the inside. But that's fine, because if he wasn't so irritated, he'd be laughing at him and Dean too.

Dean is still too busy ranting about the inappropriateness of everyone on Sam's list to really process that they're done shopping, so Sam holds the door for him, and the two of them walk through the sleet with their brand new scarlet letter bag of toys to the nearest burger joint.

 

-*-*-

"Sorry, but that's it, Dean," Sam says, once they've been seated at a corner table. On the inside, the restaurant turns out to be more of a bar than a burger place per se; loud and kind of dark, with a beer list the size of Sam's arm. "I don't know what else to tell you. You've rejected everyone except Cas, and clearly you're not gonna sleep with him either."

"Damn straight," Dean says emphatically. He feigns engrossment in his menu for a few minutes, and then adds (a little petulantly, if Sam does say so himself), "Obviously I'm not gonna make whoopie with Cas. Why would you even bring that up?"

Through sheer force of will, Sam keeps his eyeballs from rolling so far back they pop right out of his skull. "Oops, sorry, yeah. I don't know why I mentioned it. There's the male vessel problem of course, since you keep insisting you don't sleep with men, but mostly it's the incest thing, right?"

Dean makes a face like he swallowed a bug. "The... what?"

"The incest thing. You think of Cas as a brother, so obviously you wouldn't want to fuck him. That would be disgusting."

"Uh," Dean replies intelligently.

The waiter comes by to take their orders. Sam offers up a fervent prayer to Chuck he got within earshot at the 'uh' part of the conversation, rather than the 'incest' part. He orders a salad and a craft beer. Dean orders a burger with everything and “whatever beer has the highest alcohol content. Today's been really trying”.

He rubs at the back of his neck and mutters, "Maybe not exactly like a brother."

Sam pretends he didn't hear, which isn't a stretch given the noise level, and continues on faux-obliviously, "Fortunately I don't think of Cas that way at all. It's gonna be a challenge fitting him into my schedule, what with Rowena and Walt and Max, and I promised Donna and Jody I'd do a threeway with them. But I'd hate for Cas to not find a partner, and he is pretty hot, you have to admit. Maybe we should stop at a drugstore on the way home so I can steal some viagra."

Dean is atypically silent. The waiter brings their drinks over, and Dean gulps his down like it's soda. Sam's craft brew is pretty good, made right there on the Cape. Their lunches come, and Sam's salad isn't too bad either. The lettuce is a little wilty, but it's December, so what can you do.

Dean picks at his burger.

"You'd really have sex with Cas, Sam?" Dean's voice is subdued and his expression is eerily similar to a lost puppy in a rainstorm. It makes Sam feel guilty, and he has to remind himself Dean and Cas have been pulling this shit for ten whole years now.

Sam would really have sex with Cas. In fact the only reason he's never pursued it is because Cas and Dean are so obviously smitten.

"Sure," he says. "He's a great person-- well, great entity, I guess. And he's courteous and giving, and game to try new things. I bet he'll be wonderful in bed. And I care a lot about him. Why wouldn't I have sex with him?"

Sam finishes his salad, and Dean desultorily eats three french fries. The waiter gets bored of their slowness, or has to meet his 'move your customers along' quota or whyever they come back when you're obviously not done, and offers dessert. Dean shakes his head, and Sam doesn't usually get dessert, but desperate times call for desperate measures. He orders for both of them; flourless chocolate cake for himself, and blueberry pie and a second beer for Dean.

Sam digs right in.

"Listen Dean. We're not as young as we used to be," he says as he eats. The cake is quite good; rich and overpowering, just like it's supposed to be. "I can't really bang six people in one night. Be a good wingman, and do Cas for me. It'll be totally heterosexual and meaningless, I promise. Just bros being hos, doing a favor for your little brother and nothing more."

Dean scowls, but he eats a bite of pie.

"You thought up this entire sex party thing just to get me and Cas in bed together, didn't you?"

No point denying it. Dean was sure to figure it out at some point. "Yup," Sam says, and shrugs.

Dean eats a couple more bites of pie and drinks some beer. "You're an asshole, Sam. Did you really promise a threeway to Donna and Jody?"

"Yup."

"And you and Max are really gonna-" Dean makes the international 'finger of one hand poking through a finger circle of the other' sign for fucking.

"Yup."

"Whoa, dude. Well, can't say you didn't commit."

Dean sighs dramatically, and chews on a mouthful of blueberries. "Okay, I tell you what, Sam. I'll have sex with Cas once. Heterosexually. For you. On one condition."

Sam smiles inside in triumph, but he keeps his expression carefully neutral and open. "Sure Dean, whatever you want. What's the condition?"

"Don't bone Walt, Sam. He killed you, dude. That's just wrong."

 

~

Notes:

Thanks for reading, I hope you enjoyed my slightly slutty version of holiday fluff. The toy store is based fairly closely on Toys of Eros in Provincetown, MA. The dessert lube line is based on JO Gelato lubes, which don't have an apple pie flavor, but do have an incredible tiramisu.

*Potential ships mentioned in the fic that are immediately and roundly rejected:* Mary Winchester/Dean; Ketch/AU Bobby/Mary; Rowena/Dean; Garth/Dean; Max Banes/Dean; Jesse/Cesar/Dean; Walt/Dean.
*Potential ships that are eventually rejected:* Cas/Sam; Walt/Sam.
*Potential ships still in play at the end of the fic:* Dean/Cas; Rowena/Sam; Max Banes/Sam; Donna/Jody/Sam.
If I've forgotten any, feel free to let me know in comments; it was a lot of ships to keep track of.