Show Me | Part 3

Pairing: Sam x Jack x Reader 
Rating: 18+
Tags: Bi!Jack, Bi!Sam, Age Difference, Pseudo-Incest, First Kiss, Mutual Masturbation, Sexting, Phone Sex, Sex Toys, Fleshlight, Sloppy Seconds, Pining!Sam, Eventual Dom/Sub Relationship, Dom!Sam, Switch!Jack, Sub!Reader
WC: 3k

A/N: @jackandthesoulmates commissioned this piece and I’ve had so much fun coming up with all these sexy scenarios 🖤 thanks so much for your continued support babe, and for your filthy, twisted mind 😘

Show Me Masterlist

Sam is not jealous. He’s just… concerned. He saw how anxious Jack was before he left for his date with Y/N, the boy was nearly vibrating with nerves. Sam offered to drop him off at the restaurant, to help keep him calm in the car ride over. Jack had eagerly accepted, but he hadn’t spent it how Sam assumed he would. The younger man was quiet and fidgety the whole way, turning up the music as soon as they slid in the car in an effort to distract himself. 

Sam had thought Jack would have a load of last minute questions. Tonight was the big night after all. Jack hasn’t just booked a table at the nice little Italian restaurant on the main drag in Lebanon, he’s also reserved a room at a decently nice little hotel just outside town. Dean and Sam both agreed that bringing Y/N back to the bunker wasn’t an option at the moment, and would likely not help Jack get laid, considering several rooms were literal torture dungeons. That sort of thing tends to put people off. 

So Sam had dropped Jack and his hotel key off at the restaurant with a parting hug, meant to be comforting. There’s a chance it had come off a little more… possessive than reassuring, but it was too late to take it back now. And Sam had pulled the car away, watching Jack’s stationary wave goodbye in the rearview mirror. 

Then he’d pulled the car down a side street, parked up, and took up residence at a window seat in the café across the street from Jack’s date. Again, not jealous. He’s just looking out for the kid. He wants to be close by, just in case he needs something. 

Just in case. 

Jack is twitchy. 

He can’t sit still in the restaurant booth. He checks the clock on the wall every fifteen seconds on the dot, wondering why it’s moving so much more slowly than usual. He’s early, like he planned to be, but now he’s here he wishes he hadn’t been quite so early. He should have stayed in the car with Sam a little longer. Asked… anything, really. He still has so many questions. 

The tall, chipper waiter that had brought Jack to his table is walking toward him again, and Jack straightens up and tries to school his face into an expression somewhere closer to happiness than sheer panic. Y/N steps out from behind the shadow of the waiter, smiling lightly. 

“Hey,” Y/N gives Jack one of the short, still waves that she teases him for so often, and it breaks the tension a little when he laughs brightly. Jack stands and pulls her into a hug, risks a small kiss on the cheek, and when he pulls back to look at her, she’s flushed, her skin hot against his. 

“You look so pretty,” Jack blurts out when they’re both seated and the waiter has left them to fill their drinks order. Y/N tries to suppress her smile, but Jack can tell she’s pleased with the compliment. And he meant it, she’s always pretty, but something about the way she looked tonight – it’s like she’s glowing. 

“How are you?” Y/N makes small talk. The waiter brings their drinks. They order dinner. 

“So, um,” Y/N clears her throat and takes a sip of her wine before trying again. “You got the hotel room, right?” 

“Uh-huh,” Jack nods nervously, ashamed of how close his answer had been to a squeak. 

“Can I tell you something?” she asks softly, looking around as if they would be overheard. Jack leans in to listen. “I’m really nervous, are you?” 

“Oh my god, yes,” Jack sighs, happy that he’s not alone in his internal turmoil. 

“Why are we so awkward?” Y/N giggles, visibly relieved too. 

“Well, I know why I am. I have the social skills of a three year old,” Jack jokes, and Y/N snorts into her wine, not knowing just how serious Jack is about that statement. “Your reason might be something to do with that laugh,” Jack teases, taking a drink from his own glass. 

“You’re so mean!” Y/N sounds affronted, but jovially so. “It’ll be fine, right? We’ll be fine.” 

“Yeah, of course,” Jack nods more confidently than he feels. “Completely fine.” 

They’re not so fine. 

Why is it so awkward now that they know they want to go all the way tonight? Jack had had a hard time stopping himself after their last date, when they’d been making out in the dark of her car, parked in the driveway. Y/N had been running her hand over Jack’s groin the way Sam had taught him to touch himself, and it had felt fucking amazing, having Y/N’s hands on his dick, even through his khakis. But they’d both agreed they should wait, and do it right. It would be their first time, after all, and not just with each other. Ever. 

But now they’re in the hotel room and they can’t seem to calm down or get started. They’re sitting on the bed, cross legged, still fully clothed, just…staring at each other. 

Jack’s phone dings, and they both jump. He reaches for the phone beside him, sees it’s a text from Dean in the group chat, prays it’s some kind of supernatural emergency. 

Dean: Nice knowin ya kid, when you come back tomorrow you’ll be a man 

Sam must have told Dean about his date tonight. He blushes furiously. 

Sam: Dean! I told you not to text him, knock it off

Cas: What is going on? 

There’s an array of small dots flashing at the bottom of the screen and Jack mutes the chat. 

“Sorry,” he says awkwardly, looking back to Y/N. She shrugs forgivingly. 

“Anything important?”

Jack shakes his head, but then another ding goes off with a new text. He grimaces another apology, looking down at his phone. It’s not the group chat, just Sam. 

Sam: Sorry about Dean, you’ve got this buddy, have fun 

Jack sees their earlier messages on top of Sam’s newest one. A photo he’d sent of the fleshlight Sam loaned him, his cum leaking out of the pussy shaped end, to prove he’d been practicing, just like Sam instructed. 

… just like Sam instructed. Jack has an idea. 

“Y/N…” Jack trails off, still looking at his phone screen, the photo, the message from Sam, “Y/N, do you trust me?” Jack flicks his eyes up, gaze meeting hers hopefully. The nerves on Y/N’s face soften, and she smiles. 

“Yeah, I do,” she nods. 

“I have an idea, it’s a little… unusual? But I really think it can help us.” Jack’s earnest. Desperate, at this point. He never thought it would be this hard to just have sex with someone. And it was always so easy when Sam was there to tell him what to do. 

Sam’s phone rings a minute after he texts Jack, and he looks at it curiously before picking up. He hopes he didn’t interrupt at a bad moment. Except maybe he hopes that he did. 

“Jack? Is everything alright?” He sits in stunned silence as Jack voices his proposal. He wants Sam to help him, to help them, like he’s been helping Jack before. He wants Sam there, with them. Sam’s heart swells with the warmth of being needed, feeling wanted, and then he pauses to consider exactly what this would mean. He would be there while Jack and Y/N… he would see them, maybe even touch them. His cock swells even more than his heart. 

“Is Y/N okay with this?” 

“She trusts me,” Jack says simply. Right now, that’s good enough for Sam. 

Sam gets to their room quickly, he’d only been down the street. Not that Jack needs to know that he’d followed Y/N’s car when they left the restaurant after dinner. Jack opens the door with a relieved smile and pulls Sam inside by the hand. 

“Thank you,” he whispers, and Sam smiles and nods in acknowledgement. “Y/N,” Jack speaks more loudly, turning back to the girl on the bed, “this is Sam.” 

Sam stands at the foot of the bed where Jack leads him. Y/N is sitting in the middle, staring up at him with wide, glassy eyes – visibly perplexed. 

“It’s nice to meet you, Y/N,” Sam smiles, puts on his best comforting, helpful tone of voice; the one he uses a lot with nervous witnesses on cases. He sees her breath hitch in her chest when he says her name and stores that information for later. 

“Nice to meet you too,” she stammers politely, looking quickly between Sam and Jack. Jack sits back down on the bed and reaches confidently for Y/N’s hand. Sam sees her squeeze his fingers tightly, a silent sign that she does still trust him, even if she doesn’t understand what’s going on, yet. 

“Do you remember when we went for that walk in the park, by the pond?” Jack asks, eyes only for Y/N at the moment. She nods demurely. “How I told you, you’re the first girl I ever kissed?” Another nod. “And you made a joke – about how I must have had a good teacher?” Y/N’s eyes flick to Sam at Jack’s words. Sam sees the puzzle pieces connect for her. 

“Sam… taught you?” she asks shyly, eyes sliding back to Sam before she could help it, then jumping back to Jack as soon as she caught Sam’s eye. Jack was nodding. 

“Sam taught me everything,” he smiles, then hesitates, “well… everything I’ve done so far. But I thought, if, um, if you wanted…” Jack looks back to Sam, and Sam smiles encouragingly. “I thought maybe Sam could teach me this, too. Teach us this.” Jack swallows thickly, Sam sees his throat bob with the effort. 

Sam stays quiet, lets Y/N consider. She looks at him more closely now, eyes scanning, weighing up her options.

“How?” she asks eventually. Jack visibly relaxes, tension melting away, because now he can look to Sam for the answers. Sam steps forward and folds himself down onto the edge of the bed, still giving the couple their space. 

“I’ve helped Jack in a lot of different ways,” he explains gently. “Sometimes I show him what to do and I talk him through it. Sometimes I do it to myself and he copies me… sometimes we practice together.” Sam’s eyes move to find Jack, who’s smiling warmly at him, Y/N’s hand still in his. Y/N looks between them again. 

“And you– um, you can tell us what to do?” Her tone is nervous still, but there’s a flash of something more in her eyes. Hope, maybe. 

“If that’s what you both want,” Sam nods. 

Y/N and Jack look at each other simultaneously, and Sam is pleasantly surprised to see how in sync they are with each other. They’re strangely peaceful, now that he’s here; now that they know it doesn’t have to be solely up to them. Someone else can be in charge. They’re both more comfortable with that, Sam can tell. He settles himself into the control while he waits for their answer, confident he already knows what it is. 

She takes her time, considering in silence, before giving Jack a nod, a small smile on her face. 

“Yeah?” Jack checks carefully, but Sam sees his fingers twitch around hers. She nods again, smiling a little easier. 

“Y/N,” Sam speaks up, “this might seem a little overboard to you, but I need you to use your words. Consent is very important to me, and to Jack.” Sam tries to stress this as gently as possible but he knows he needs to be careful in such a delicate situation, and he could never stand it if he hurt someone, or made them uncomfortable. 

“Yes,” Y/N answers, without hesitation but not in a rush. There’s a calm surety to her tone as she looks Sam in the eyes, and Sam believes her. 

“Alright then,” Sam breathes, like he’s gearing up for something, even though he knows right now he won’t be participating, their first time should only be about them. If he plays this right though… 

Jack beams and leans forward to give Y/N a small kiss, and Sam takes advantage of the natural start to the proceedings. Pushing forward over the bed, he presses a hand to the back of Jack’s head so he can’t pull away. 

“Keep kissing her Jack,” Sam speaks softly against Jack’s ear, but makes sure it’s loud enough that Y/N can hear his instructions too. “Take her breath away.”