Show Me | Part 2

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

“Good morning,” Jack greets Dean cheerfully, getting himself a cup of coffee and sitting down across from the hunter. 

Dean grunts in acknowledgment of Jack’s entrance but doesn’t speak. His eyes are still closed. If he wasn’t sitting up and holding his own mug of coffee Jack would have thought he was still asleep. Leaving him be for the moment, Jack pulls the cereal towards himself and digs into his sugary breakfast – something he and Dean have in common, unlike their feelings towards mornings. 

Jack gets another cup of coffee when he finishes his first, and Dean stretches out his cup wordlessly, asking Jack to give him a refill as well. He grunts again in thanks and goes back to savouring his morning caffeine with his eyes closed. 

“Dean?” 

“Hmm?” he huffs, blinking his eyes open. 

“How do I know when I’m ready to ask her out?” Jack asks, shy but straight to the point. 

“Ask who what?” Dean squints at him, clearly confused. 

“The girl I like, Y/N,” Jack supplies, realising he never mentioned her name before. 

“Wait, wait,” Dean shakes his head and tries to focus, “before, when you were askin’ about sex and,” he waves his hand in vague circles, “whatever – you’re asking because there’s an actual chick you like? Not just… curiosity an’ shit?” 

“Yes, Y/N is an ‘actual chick’,” Jack nods, putting emphasis on Dean’s phrasing. 

“And you like her? Like, you don’t just wanna have sex with her, you actually like her, like her.” 

“Well, I do want to have sex with her. That’s why I asked you and Sam for help.” Jack isn’t sure what the distinction is. Aren’t you supposed to like all the people you have sex with? 

“Well, yeah, but you’re not lookin’ to hit and quit, you want to, y’know, date this girl. Yeah?” 

“Yes, I think so,” Jack nods. 

“Well that’s a whole different story man,” Dean laughs, scrubbing his hands through his hair. “Dating a girl, you’ve gotta go slow. You build up to things like sex, you don’t ever sleep with her on the first date, or she’ll think you’re way too pushy. You have to make her want to have sex with you, make her think it was her idea. ” 

“Oh,” Jack blinks, taking in this new information. “So how do you date a girl and make her want to have sex with you?” 

“Oh, my young padawan, I have so much I can teach you,” Dean grins, and Jack returns the smile. 

“Perfect.” 

Sam looks up from his laptop when he hears a knock on his door. “Come in!” he calls, knowing it will be Jack, Dean doesn’t bother with knocking usually. “Hey Jack,” he smiles when the boy ducks his head around the door. 

“Can I ask you a question, Sam?” 

“Sure, bud. What’s up?” Sam closes his laptop and pats the empty space on the bed next to him, which Jack takes. 

“I’m texting Y/N, and I don’t know what I should say,” Jack trails off nervously and Sam smirks. Jack and Y/N have been texting for a few weeks now, ever since Dean had taken Jack out for a lesson in how to ask for a girl’s number. 

Apparently Jack had been a natural, and had Y/N eating out of his hand in no time. Sam almost wishes he could have seen that, he bets Jack would have had the cutest flush… he jerks himself away from his thoughts and back to the present. 

“What did she say last?” Sam asks, clearing his throat awkwardly, hoping Jack didn’t notice his brief brain fog. 

“She sent me this picture,” Jack holds his phone out for Sam to see, and his jaw drops. The picture is of a stunningly pretty girl wearing nothing but dark blue lingerie, her lips pouting and shiny with gloss, and a finger twirled in her hair. 

“Wow,” Sam manages to stutter after a moment. 

“What do I say? Dean told me I shouldn’t be too forward, but I also should always tell her the truth, but right now the truth is that I want to have sex with her, but if I say that she might hate me,” Jack babbles, thoughts spilling out in a cascade, and Sam smiles widely at how cute he is when he’s flustered. 

“Hey, slow down, it’s okay,” Sam grabs Jack’s shoulder and squeezes, trying to ground him. “It looks like she’s trying to sext with you.” 

“She wants to have sex with a text message?” Jack questions, brow quirking up curiously. 

“Well, kind of,” Sam shrugs, “it’s like when you touch yourself, but instead of just imagining what you want to do with someone, you’re talking about it with them. It makes it more real, I guess. And sometimes along with the texts you send pictures, like that, to show what you’re wearing or, um,” Sam feels himself flush as he stutters, “what you’re not wearing.”

“What do I say?” Jack asks again, nervously, but Sam can also see a light in his eyes telling him he’s excited. 

“Well, when you saw that photo, how did it make you feel?” Sam asks, and Jack considers for a moment. 

“Tingly. And hot,” he settles on. Sam chuckles. 

“Did you get a little hard when you saw it?” he asks with bated breath, and Jack hesitates for a moment but then he nods. 

“Tell her that,” Sam pushes the phone back towards Jack. “That will make her feel sexy, she’ll know you want her the same way she wants you.” Jack types up a quick message and turns the phone back to Sam. 

“Like that?” 

Jack: Your picture made me feel tingly and hard

Sam tries to hide his laugh, not meaning it mockingly, and takes the phone from Jack. “Think about the way I talk to you when we have our lessons,” Sam muses, then types a new message for Jack. “Maybe something like this.” 

Jack: My god, you’re beautiful. That pic got me so hard baby

“Thanks Sam,” Jack smiles and hits send. 

“Anytime,” Sam swallows hard, giving Jack’s shoulder another friendly squeeze. Jack’s phone dings with another message. 

Y/N: Can I see?

Jack blushes fiercely and Sam smirks. When he looks at the boy’s lap, he can see a small bulge in his sweatpants. Sam gets up and closes the door. Jack looks up at him curiously while he returns to the bed. 

“Get comfy. I’m gonna help you sext her.” Jack looks visibly relieved and Sam feels a glow bloom through his chest. Jack needs his help, he wants Sam to do this. 

“Start teasing her a little, take a photo of your dick with your sweatpants on.” Sam climbs onto the bed behind Jack, straddling his legs around him and leaning back against the headboard with Jack sitting between his thighs. Jack leans back into Sam’s chest so he can get a better angle for the photo. 

“Show me,” Sam instructs, and Jack lifts the phone for him to check the picture. “I think we can get you harder than that, don’t you?” His voice spills out over Jack’s neck, low and warm. Jack nods and reaches to touch himself, massaging his boner through his sweatpants. 

“Yeah, there you go,” Sam encourages gently, brushing his hands up and down Jack’s arms. “That’s better, take another picture.” 

Jack takes one and hits send once Sam gives his approval. They only have to wait a few seconds for Y/N’s reply.

Y/N: Shit you look big

Y/N: That’s so hot Jack 

Sam reaches around Jack and takes the phone. “Touch yourself for me, baby boy. I’ll type, you just focus on feeling good. Tell me if there’s anything you want me to say to her.” 

“I want to tell her she’s hot too,” Jack breathes heavily, pushing one hand into his underwear and starting to jerk himself. 

Jack: Are you as turned on as I am? 

Y/N: Definitely 

Jack: Show me? 

“How do girls show you they’re turned on? They don’t get hard like boys do,” Jack asks curiously. 

“Girls get wet,” Sam answers. “And I’m hoping I’ll be able to show you what I mean in a minute.” 

He’s not disappointed when another text arrives a moment later with a photo attached. It’s a picture of Y/N’s panties, pulled down her legs and stretched between her thighs so they can see the bit of the material that had been between her legs. There’s a very obvious dark patch on the cotton where her arousal had leaked out of her, and Sam groans, unable to help himself. 

“See that spot there, Jack? That’s how you know she’s turned on. When you get a girl all wet and slippery for you, god, it’s one of the best feelings in the world, feeling that and knowing you did that to them.” 

“I– I did that to her?” Jack pants, bucking his hips up into his hand, squirming against Sam’s chest. 

“Yes you did,” Sam whispers in his ear. “And I think you should show her what she’s doing to you. Pull down those pants baby, send her a pic of that pretty cock.” Sam’s own cock is straining against his jeans, but he ignores it. He can take care of himself later – right now is about Jack and Y/N. 

Jack wriggles for a moment and gets his sweatpants and underwear down around his thighs. Sam wraps one of Jack’s hands around his dick, strokes him with it a few times, then holds him still. Jack uses his free hand to take the photo, showing Sam for his approval before he sends it. 

“So fucking hot, baby,” Sam growls against Jack’s ear, moving his hand again to encourage Jack to keep jerking off. He takes the phone back and sends Y/N a new text to go with the photo. 

Jack: Are you wet enough to fit this into you?

Her response is almost instantaneous. 

Y/N: Fuck so wet Jack 

“She’s got a fucking dirty mouth,” Sam chuckles darkly. 

He loves it, the thought of her dripping for Jack, begging for his cock. He thinks about what it would look like to watch him sink into her body. He wishes he could see Jack fuck someone, see him lose himself in some cunt. He gets an idea. 

“Stay here Jack, tell her about how you’re touching yourself, tell her you wish she was here to touch you.” 

Jack nods wordlessy, typing out what Sam’s told him to say. Sam gets up from the bed and goes to his dresser, digging through the shirts in the bottom drawer to a shoebox hidden beneath them. Inside is his stash of toys, including the one he’s after now. He pulls out the fleshlight and some lube and carries it back to the bed. 

“Wh… what’s that?” Jack groans, looking at the items in Sam’s hands. 

“This is called a fleshlight,” Sam holds up the toy so Jack can see the silicone mold on the end that looks like a pussy. “You use it on your cock, like it’s a girl, and you fuck into it.” 

“It, mmm,” Jack moans, air squeezing tightly through his throat when his fingers catch clumsily on the head of his dick while he’s not paying attention, “it will feel like sex? Like, real sex?” 

“Close as you can get without a girl here,” Sam chuckles darkly, drizzling lube into the crevice of the toy. “C’mere Jack, stand up.” Sam sits on the bed and takes Jack’s phone while he stands and struggles out of his sweatpants. 

“What are you saying?” Jack asks when he notices Sam sending another text. 

“I’m asking if she’s alone, and telling her to go somewhere quiet,” Sam smirks. “Take this off too,” he tugs at the hem of Jack’s shirt, and Jack pulls it off so he’s naked in front of Sam. 

Sam reaches forward and touches Jack’s cock gently, making the excuse mentally that he’s just making sure Jack is lubed up enough to use the toy, but he takes a moment to lose himself in the feel of him on his palm. The text tone pulls him out of his thoughts. 

Y/N: I’m all alone, no one here 

Y/N: what do you want me to do

Sam smiles, that’s exactly what he wanted to hear. He holds the phone out to Jack. 

“Call her,” he instructs simply. Jack blanches. 

“What?”

“Call her,” Sam repeats. “You know the way I talk to you when you touch yourself, that’s how I want you to talk to her. And while you do, you’re gonna fuck this fleshlight, and pretend you’re fucking Y/N.” 

Sam runs his hands along Jack’s cock again, jerking it lightly, and pulling the boy in a little closer. Jack looks nervously at the phone in his hand. 

“I’ll be right here to help if you get nervous baby boy, it’s okay,” Sam reassures him, pressing the toy lightly against the tip of his cock. 

Jack presses call. 

“Put it on speakerphone,” Sam tells him, and Jack nods obediently. 

“Jack?” Y/N picks up the phone quickly. Her voice is breathless, strained, and Sam can tell she’s been touching herself. 

“Y/N,” Jack sighs happily, his face lighting up when he hears her voice. “Oh my god,” he moans a split second later, because Sam starts pushing the fleshlight down his cock, sucking him into the tight, wet space. Y/N moans on the other side of the phone. 

“Fuck, Jack, you sound so sexy,” she whimpers. 

Fuck, she sounds sexy, Sam thinks. He takes a moment to rearrange himself in his jeans so he can see this through with a clear head. 

“Are– are you touching yourself?” Jack asks shakily, fucking his hips shallowly into the toy, into Sam’s hands. 

“Ever since you sent me that first photo,” she admits, voice pitching strangely when her breath runs out mid sentence. “Made me so wet, thinking about you getting hard to that picture of me.” 

“You’re so beautiful,” Jack moans, hips jerking in response to her words. 

Sam reaches forward and pinches Jack’s hip to get his attention, he points at the fleshlight and then at the phone, hoping Jack gets the message. “I– I’m touching myself too. You made me so hard, I couldn’t help it. I’ve uh, I’ve got this toy,” he grunts and takes a deep breath.

“Yeah?” Y/N asks, clearly intrigued. “What kind of toy?” 

“A, um, a fleshlight,” Jack goes bright red when he says the word, and Sam thinks it’s one of the prettiest things he’s ever seen. “I wish, wish it wasn’t a toy,” Jack stutters. “Wish it was you.” 

“Fuck, me too,” Y/N whines, voice high and thin, desperation bleeding through. 

“Yeah? You want me inside you?” Jack asks. 

Sam shudders. He looks down, watching Jack fuck in and out of the toy. He pinches Jack’s hip again and mouths ‘faster’. He pumps the fleshlight a few times, encouraging Jack to speed up, and he takes the hint, but loses his balance a little and falls forward, catching himself on Sam’s shoulders. Sam grits his teeth, unbelievably turned on by Jack fucking the toy in his hands while he braces his forehead against Sam’s neck, moaning down the phone to his little girlfriend. 

“God, yes, Jack,” she answers, and Sam thinks he can hear something else in the background. Buzzing. “I got a toy too. Needed something inside me, until I can have you.” Fuck this girl can really talk, Sam thinks. He’d like to give her something to fill that wet little hole with. “Are you close Jack? I’m really fucking close,” Y/N whimpers. 

“Oh god, so close, Y/N,” Jack breathes down the phone, and Sam knows he’s telling the truth. His hips are flying in and out of the toy in his hands, its wet slapping sound filling the room. “Cum, cum with me, yeah?” he moans, and Sam has to fight down a groan of his own. 

“Yeah, oh fuck, yes! Gonna cum, gonna…” 

“Cum for me baby girl, c’mon,” Jack grunts, hips thrusting sharply, until he finishes with a strangled groan, biting down on Sam’s shoulder to muffle the sound. Y/N’s own whimpers are still bleeding through the receiver. 

When Jack pulls out of the fleshlight, he groans, and Y/N laughs. The conversation is surprisingly easy and un-awkward between them, for someone as nervous as Jack usually is. Sam’s glad he’s found someone he can talk to. Jack cleans himself up quickly after he says goodbye to Y/N, and he tries to leave the room quickly but not before Sam catches him to ask: 

“Baby girl, huh?” It’s mostly teasing, he tries to smile, but part of him is also trying to probe just how serious Jack is about this girl. 

“Well,” Jack shrugs, mildly embarrassed if the colour of his cheeks is anything to go by. “I like it when you call me baby boy, so…” he leaves the statement hanging, and Sam feels his heart clench. 

“Yeah?” 

“Yeah,” Jack nods, smiling sheepishly up at Sam. 

“I like it too baby boy,” Sam smiles, and gives Jack a gentle kiss, before he ushers him out of the room. 

Alone again, Sam quickly sheds his own clothes and returns to his bed. He pulls out the lube and slicks himself up in his hand, jerking rough and fast to alleviate some of the desperation he’s been feeling. 

His phone is on the nightstand, and he grabs it and opens the new messages, going straight to the photos of Y/N and Jack he’d sent himself. Keeping the photos in view, Sam reaches for the fleshlight with his free hand and shoves inside. He can feel Jack’s cum, warm and sticky, lining the inside of the toy. He barely lasts thirty seconds before his own load joins Jack’s.