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The Journey To Sam Winchester's Hidden Kink

Summary:

DISCONTINUED.

“Take the pillow with you. Once you’re in position, lock your wrists again.”

The almost inaudible sound of Dean’s button popping open has Sam’s cock thumping against the couch. He’s so hard he doesn’t know what to do with himself, but he angles his hips as far away as he can so that he doesn’t rut up against the soft, inviting solid structure in front of him. He hasn’t been told that he can, and he also isn’t so sure he can go more than one stroke before coming embarrassingly fast.

“Such a good boy… My good baby boy. You’re killing me here, Sammy,” Dean comments, tugging down his zipper and freeing his cock in the next few seconds, jeans bunched up underneath his thighs–crushed against the couch cushions. Sam moans as Dean angles his cock towards him, leaking slit pointing directly at the crease between his mouth. There’s nothing he wants more than to get his lips on it, but he’s prepared to wait as long as it takes for Dean to tell him to, “You want to suck my cock, sweetheart?”

Notes:

(See the end of the work for notes.)

Chapter 1: In The Beginning

Chapter Text

Dean collapses on top of Sam, mind fogging over as Sam’s ass wrings the last remnants of his orgasm out of Dean, leaving him sleepy and sated. He can’t believe that Sam had been in the mood after a night like tonight, but he’s not gonna complain about it.

“Dude, you’re heavy. Get off,” Sam mutters, weakly pushing at Dean. Sex does tend to suck the energy right out of Sam, so Dean takes pity on him, and lethargically rolls over onto his back, trying to get his breath back after their activities.

He pats Sam on the chest twice with his closest hand in way of thanking him, crossing his arms behind his head afterwards and breathing in deeply through his nose, relaxing after their vigorous lovemaking.

“That… Holy shit, Sam… That was awesome,” Dean manages through attempting to get his breath back, nudging Sam’s heel with his big toe under the covers, another way of saying thank you. The sex they just had deserves a playback, in Dean’s opinion.

“When I said you could fuck me as hard you wanted to, I assumed you wouldn’t push it past your limit,” Sam admits, looking over at Dean, pleased to see him looking so relaxed and happy. That grin on his stupidly handsome face is going to be there for a while, and Sam’s completely fine with that.

“Hey, you gave me free rein. Of course, I’m gonna get as much out of it as I can,” Dean reasons, breaths starting to even out. Through his orgasmic haze, Dean spots something troubling Sam in his eyes, which have always been his easiest tell. Dean twists onto his side and thumbs Sam’s cheek, turning his head to lock their eyes. “What’s up, Sammy?”

Sam falters under Dean’s gaze, the affectionate touch a bittersweet moment, due to the fact that Dean has locked on to the fact that there is something bothering Sam, however, he’s really not sure how to go about explaining it.

“Am I… Uh, y’know…  Boring?” Sam mumbles, turning his head out of Dean’s grasp.

“What do, uh… What do you mean?” Dean inquires, a little confused by the sudden Q and A.

Sam shifts onto his side as well, arguing internally with himself that Dean may or may not take the piss out of his confession, but he will still be understanding in his own way, so there’s no reason for him not to say anything.

“I know that you’ve done a lot of stuff… A lot of, uh… Kinky stuff, and I guess I haven’t, so I thought maybe you were getting bored,” Sam confesses, shrugging one shoulder at the end, unconsciously fiddling with the creases in the sheets.

“So, what, you wanna get kinky?” Dean surmises, head filling with all sorts of naughty shit he can do together with Sam. He dials it back when his cock starts to take an interest. Dean really doesn’t have it in him to go at it again right now, so he’s going to have to save those types of thoughts for the shower.

Sam nods. “I guess I just wanna try some stuff out… See what I like.”

“We can do that,” Dean agrees, not seeing why Sam should be so embarrassed by this admittance. “Just be straight with me when you don’t like something, so we can cross it off the list. I don’t want you putting up with it just because I might be getting off on it.”

Sam frowns at that. “That’s not really fair to you, Dean—“

“Trust me, Sammy—if you pretended you enjoyed something just because I was, and then I found out that you hated it, I’m not gonna be happy about it, believe me,” Dean states, pressing a gentle kiss to Sam’s lips, solidifying that factoid.

Sam understands that the kiss means more than Dean can bring himself to say, which is that he really would appreciate it if Sam didn’t do something just for him, just because Dean likes it—that he wants it to be equal between them, though he’s more than willing to help Sam find his kink.

“All right, Dean. I won’t,” Sam agrees, laying his head on Dean’s chest, comforted by the rise and fall of Dean’s body, the heart beating defiantly against his ear always enough to calm him in any given situation.

“Good. We’ll start light. Work our way up. There’s bound to be something that gets your rocks off, that Earth Dwellers frown upon,” Dean muses, running his hand up and down Sam’s arm, eyes closed.

“Yeah… So, what gets your rocks off?” Sam asks, curling his leg over Dean’s, synchronising their breathing. He has a few ideas about what Dean likes, but so far they haven’t really done anything other than having sex. Sex with Dean is great… Sam never thought he would love having his ass fucked as much as he does, but he’s come to terms with it over time and is no longer embarrassed by how much he enjoys it. Still, they haven’t gone passed that, so Sam’s never done anything… Kinky with Dean before.

“Uh, I don’t really know with dudes, since you’re the only one I’ve ever been with, but I love girls in lingerie. Really skimpy clothes, like they’re almost completely naked. I had a major thing for cheerleaders back in High School… Don’t worry, I’m not gonna ask ya’ to get all kitted out in cheerleader gear, screaming “Go Lions” with red, puffy pom-poms, while yo—“

“Okay, stop. The more you explain, the more it sounds like you really want that,” Sam cuts him off, a shudder of disgust thrumming through him at the imagery Dean created.

“Anyway… I’ve done, uh, some stuff. Not like a boatload, but enough to be just over the line of sexually adventurous,” Dean explains, wondering what sort of things he might find that he likes himself throughout this endeavour.

“So, we just start at the bottom of the barrel, and…” Sam trails off, noticing that Dean’s breathing has evened out, and he’s no longer awake.

Sam smiles, pressing a gentle kiss to his chest, and falls asleep shortly after.