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You never took Sam for the dominating type.
If you were being completely honest, you had always thought that Dean would be the more dominating one. Of course until now, you’d never been in bed with a Winchester.
After a long, alcohol fueled conversation with the youngest brother, his kinks came to surface, as did yours. You’d never been tied up in a sexual way before, and you were dying to try it. But you of course wanted to try it with someone you trusted, so naturally you figured it would just never happen.
That’s when Sam mentioned he would be willing to do it with you.
It was the next day now, and you were in the dungeon with Sam, the door to the room locked and you had even told Dean not to come knocking… no matter what he heard.
Totally naked with your arms shackled above your head with devil’s trap chains, and you stood on a small platform against the wall so that your arms weren’t too stressed while Sam did his thing.
Sam still wore his boxers and a tshirt, and you watched with anticipation as the table that was typically used for torture devices was currently filled with sex toys like you wouldn’t believe. A flogger, vibrators, lube, a paddle, and even nipple clamps.
You weren’t quite sure if you’d get through all of it, but you wanted to at least get through most; and so did Sam.
Sam ran his fingers over the toys, not quite sure where to start, so he asked you, “What do you want me to use on you first?” There was a fire in his eyes that you hadn’t seen before, and a smirk that reminded you of his soulless days.
“Start light, I guess.” you said, watching as Sam looked up and down your body, totally exposed and ready for him. You were totally confident in yourself, and if you were being quite honest you’d been wanting Sam to look at you like that for a long time.
Sam stepped forward then, not stopping until he stood just inches from you. Even with you on a platform you were still shorter than him, but not by much. You looked up at him, your lips parted, expecting him to lean in.
Instead, you felt his hand on your waist. His hand was warm in the chilly dungeon. It sent a chill through you, as his finger tips travelled up and around to your front and up your torso. Looking down, you watched as his fingers traced the underside of your breast, and then up to your nipple.
Sam took both hands then, placing two fingers around each nipple and teasing lightly, sending the small pleasure right to the most intimate parts of your body. You took your bottom lip between your teeth before looking back up at him, letting his thumb circle each nipple as if your body belonged to him.
“Is this light enough?” he asked, getting a feel for what you could handle.
“Too light.” you breathed as you resisted the urge to press your legs together, knowing this game that you were playing didn’t allow that. Not yet, anyway.
Sam licked his lips just then, watching you watch him, just as he began using both his forefingers and thumbs on your nipples, and twisting lightly. He raised his eyebrows, inquiring if this was still to light.
“Harder.” you said, never for even a second breaking eye contact with him.
The sensitivity of your nipples was increasing, and just as you spoke, Sam pinched down; not hard, but enough to make you squirm.
You let out a small whimper, and let your head fall back just a bit. Sam’s touch was gentle. Too gentle. You wanted something harder. You needed more.
“You know what you signed up for, don’t you?” Sam asked just then, bringing your attention back to him.
“I don’t wanna know.” you said in a low, breathy voice.
Your hands wrapped around the chains that cuffed you to the ceiling, and you enjoyed it as Sam’s hands then covered your breasts before he went back to feeling you… all over. Though the place you wanted to feel him most went untouched.
“So sensitive,” he said as his fingertips brushed over your neck, “we might not even need some of those toys.”
With your heart pounding, you looked down, noticing his cock already pressing against his boxers, probably throbbing and ready to take you right then.
“Safe word?” you asked.
“How about ‘stop’?” Sam suggested, bringing a smile to both your faces.
“Works for me.” you said.
Sam stepped away then, over to the table a few feet away from you, just out of your reach. He looked over everything again, wondering what to do next. Glancing between you and the table, he noticed your gaze landing on the nipple clamps.
He picked each of them up just then, they weren’t attached by a chain like most would be. Surprisingly, they were something that you had already owned. They were something you liked to use when you were alone. He looked at the small heart shaped clamps, and walked back towards you.
You watched Sam as he adjust each of them to fit on each of your sensitive nipples perfectly, not tightening them too tight. The cold metal of the clamps sent another chill through you, causing you to absentmindedly rub your thighs together, which made Sam stop.
He only looked up at you, and reached up to run his fingers through your hair. You didn’t speak, trying to stay as good as you could… no matter how badly you wanted to come already.
“First time you get off easy,” Sam began, “next time… not so much. Understood?”
You nodded, careful not to let his tender yet dominating actions turn you on even more.
Sam stepped back, watching you watch him again as he reached down into his boxers, pulling his long, thick cock out and smiling as you took in a sharp breath.
Fuck, you wanted him inside you.
He pumped himself, slowly, and groaning with each stroke he made. Using your body as something to get off to. You could feel just how wet you were, and you were wondering just how long it would be before your inner thighs would be slick with your own arousal.
You wanted to touch him, you wanted to suck his cock, make him writhe under your touch.
“Please, Sam.” you begged. It didn’t help that he stopped touching himself then, and pulled his boxers back over his erection.
“Soon enough.” was all he said before grabbing the smallest of the two vibrators that sat on the table.
They were both yours. One you typically took with you when travelling. The other was for when you were home in the bunker, and needed to have a good time with yourself.
The smaller one was compact, maybe four inches long, used for clit stimulation only. Sam clicked it on, and flipped through the settings, seeing how hard it could vibrate. He stood in front of you now, with it on the highest setting, and held it against one of your nipple clamps, making you sure that you could come just like this if he held it there long enough.
You swallowed thickly, watching as he adjusted it down again, to the lowest setting. Meant for teasing, not for coming.
Sam trailed the small toy down the front of your body, letting the light vibrations make everything around you feel like white noise. It wasn’t until the toy reached the lips of your pussy that it got really hard to hold still.
You pulled on the chains, letting Sam do everything he wanted as you tried like hell to be good; to be patient.
“Don’t come.” Sam said. His voice was just as low as ever and you wondered if he was struggling with the need to come as well. You didn’t get the chance to look at him before the toy touched your clit.
It was like a shockwave, racking your body with intense pleasure. You were already so close, you just wanted Sam to let you come.
He rubbed the toy against your clit, and each time it stroked over your sensitive bud, your body jerked from you trying to keep from enjoying it too much.
“Sam.” you moaned, your hips bucking, your breaths coming in short pants.
“So worked up already,” he whispered just before clicking the vibrator up to the next setting.
“God, fuck.” you whined. This time you were totally unable to keep yourself from moving around.
You pulled at your restraints again, making the chains rattle as you took some of your weight off of your legs. It was the only thing you could think to do to keep yourself from coming.
“You’re being such a good girl.” Sam praised you. But just as quickly as he’d started really torturing you. He’d stopped.
The loss of the vibrations against your clit caused you to whine, and you wanted nothing more than to beg Sam to fuck you. Technically, fucking wasn’t even in the plan.
Your thighs were slick now, and your walls were fluttering around nothing. The nipple clamps gave you something to focus on, at least.
Sam set the vibrator down. It was undeniable that he just wanted to touch you, to feel your soft skin under his finger tips again, to kiss you, to bury himself balls deep inside you. But he knew just as well as you that this would all be worth it.
You couldn’t see it, but this was just as much torture for him as it was for you.
He walked back to you now, placing his hands on your hips and looking down into your eyes. He licked his lips again, and you stood up straight now, to show him that you were good, that you deserved to come. Sam didn’t miss a beat as his hands moved from your hips directly up to your face as he softened for a moment to kiss you.
That definitely wasn’t what you’d had planned. But at this point, it was inevitable. You wanted him, and he wanted you.
It was a rough kiss, one that sent even more of a tingling feeling down south, directly to your aching pussy. And you felt it as his tongue slid into your mouth, passionately, and possessively. It was like he was sliding into you. The most torturous part was that he wasn’t. You were just that on edge.
He pulled away then, both of you breathing heavily. Sam suddenly seeming to disregard the rest of the toys, as his hand travelled down your body, and as he dipped his fingers into your soaked folds.
It was so much better than the vibrator, so much better than anything you could’ve imagined up until this point. And he knew just what he was doing. Your eyes fluttered shut and your head fell back as you completely gave yourself up to him.
“Can I?” you whispered.
“Just once.” Sam said, and you finally let everything go. You let yourself go, and you let Sam’s fingers work magic on you.
His free hand found your breast, and he tightened one of your nipple clamps just slightly as the pad of his middle finger circled your throbbing clit. Your legs were shaking and threatening to give out, but you didn’t care. These chains that were holding you up were there for something.
As he began to roll your clit between his middle finger and thumb just then, you let loose. You moaned loudly, your face contorting with pleasure, your lower belly tightening as you drew closer to your release.
“God, Sam… yes.” you cried, the sound of your wetness as Sam took a moment to move his hand back to tease your entrance filling the dungeon.
“Open your eyes.” he said, and you forced them open, being met with his sparkling hazel ones as his fingers brushed against your clit again.
“You gonna come for me?” he asked, earning a nod from you. Or at least.. You thought you nodded. One couldn’t be so sure in this state of pleasure.
“Yes, Sam.” you moaned, and just as you felt your orgasm creep up on you, just as you began to feel that very anticipated release… Sam pulled away.
But that didn’t stop your orgasm.
Your body screamed at you, begging for contact… from anything. The waves of your orgasm were strong. But without the stimulation of Sam’s fingers… they were slow. Too slow. You tugged at your chains and begged Sam to touch you. You tried to rub your thighs together, only for it not to help in the slightest.
And when your body had finally calmed down… Sam smiled.
“What was that?!” you asked, slightly annoyed but remembering that you agreed to this.
“I let you come.” he said, his eyebrows raised. And you couldn’t resist him. You couldn’t be annoyed. That was only your natural reaction. It was in fact incredibly hot and you could only imagine how Sam felt as he ruined your orgasm.
You smiled just then, and laughed slightly, noticing the thin layer of sweat that now covered your body, “What else you got for me, Winchester?”
Surprisingly, Sam reached up then and began to remove your nipple clamps. He tossed them back onto the table and made eye contact with you yet again. He turned and looked at the table again, wondering what to do next.
“Paddle.” you said, not even giving him the chance to think about it. Sam looked at it, studying the leather object. It was one of the few things you both went and bought before all of this.
Sam then grabbed it, but he also grabbed the larger of the two vibrators that rested on the table. You wondered what he was thinking, but didn’t ask. But before moving any further, he grabbed the key for the chains that held you up, and looked over at you.
“You’re gonna need your hands for this one.” He said.
It took no time at all. Sam let you down off of the platform, and situated you on a chair. You were leaning over the back of it while you kneeled on the seat; Sam making sure it was secure and wouldn’t tip over before he found some rope that was stored on one of the bookshelves that led into the dungeon.
You weren’t going to get off so easily (so to speak), and before you knew it your wrists were bound again, by this skinny black rope.
“Now,” Sam finally said, “I’m going to give you this,” he went on as he held the vibrator up, “and you’re gonna fuck yourself with it.”
Fuck, Sam Winchester, you thought.
Really, you weren’t sure how much better it you could get, but he clicked the vibrator on to one of the lower settings and helped you position your arms properly, so that you could do what he wanted.
“Comfortable?” he asked.
You answered him with a moan as you went ahead and slipped the vibrator in. It wasn’t as big as Sam’s cock was, but it was enough for now. As it usually was.
Your hands reached perfectly, and Sam walked around behind you, watching as you slid the device in and out of your pussy. You were completely exposed to him (more so than before), and so open and confident, and he loved it just as much as you did.
He resisted the urge to touch himself again, because he knew he wouldn’t want to stop if he did. Watching you as your worked yourself over, fully intending to come again (and soon) was unlike anything he’d ever imagined.
You couldn’t see what Sam was doing, but you assumed he was going for the paddle, and you only smiled as you waited to feel that pleasurable sting while your favorite toy was inside of you. You were certain that you were the loudest you’d been as of yet when you felt it come down on you the first time, landing on your ass with a loud smack.
“Again, Sam.” you begged. And you wish you could’ve seen the look on his face when you begged him.
The paddle came down on your ass once again, and you body jerked from the sting, but your pussy throbbed as you came closer to another orgasm.
There had to have been a fair amount of red marks on your ass when Sam was done, and you were good the whole time. You didn’t come once. You really wanted to… but you wanted Sam to be the reason you did.
“Keep fucking yourself.” he said, and you heard the sound of the paddle hitting the table and then a second later, you felt Sam grip your ass.
Your eyes rolled into the back of your head as Sam’s mouth landed on the back of your thigh, kissing you, and tasting you. You were craving him so badly. He took the vibrator from your hand then and started thrusting it in and out of you himself, allowing you to move your hands back up and get comfortable again.
Sam turned the dial on the vibrator, turning the speed up to a higher setting (but not the highest) as he continued fucking you with it, faster than what you were able to. His mouth was on your ass before you could so much as cry out for him, like he knew just what you wanted.
He rimmed you, his tongue working you over in another way you didn’t know was even possible. He was completely in control now, not that he wasn’t in control before… but now he was taking you all the way.
Sam pulled the vibrator out of you just then, and clicked it off before moving his tongue down to your pussy, licking your entrance and moaning as he tasted your walls.
“Sam,” you said, unable to take it anymore, “fuck me, please.”
He moved quickly, without you needing to tell him twice, and pulled away to stand and help you up off of the chair. He’d taken his shirt off, and you were all over him as he worked to remove the rope from your wrists.
Once your hands were free, you all but jumped up and wrapped your arms around his shoulders as you crashed your lips into his. The bruising kiss told him just how desperate you were for him as he wrapped his arms around you and picked you up, allowing you to wrap your legs around him as he made his way to the nearest wall; backing you up into it.
The wall was cold and you brought your hands around to his face, feeling his five o’clock shadow on his skin as you tasted yourself on his tongue.
He moved around, using his hands to both explore your body and pull his boxers down, the rush to get inside of you probably slowing him down more than anything. But you didn’t care, this was the single hottest thing you’d ever done. So you just kept kissing him, you kept rolling your tongue against his.
And finally, finally, you felt the tip of his cock pressing at your folds. Your stomach did flips as your feelings for Sam finally came to surface, though you were sure they already had when he kissed you for the first time earlier.
He used your wetness to slick his cock against you, those extra couple of seconds torturing you more than what you could handle as you bucked your hips, helping him slide into your entrance in one quick movement.
As he sank into you, both of you let out the most pornographic of noises as your walls adjusted to his large size. You didn’t need to tell him to move, he needed to just as much as you needed him to. And it wasn’t long at all before he began fucking into you at an agonizing pace, causing black spots to fill your vision, and you weren’t sure if you’d ever been so loud during sex.
You felt the tightening in your belly again, and finally, you knew that Sam wouldn’t leave you hanging like he did last time. Your nails dug into the skin on his back as he rested his forehead against yours as you both watched his cock sink into you repeatedly.
Sam held onto your hips as you arched your back off of the wall just then, giving him a perfect view of your body. “Let me know when,” he said, “I wanna come with you.”
The pressure was building up inside of you and it wasn’t but a few seconds before you cried, “Now!” just before your release took over.
Your walls clenched around his cock and his hips stuttered from the feeling, your tight pussy feeling better than anyone he’d ever had. The sound of him pounding into you filled your ears as the waves of your orgasm moved along much quicker this time, and much more intensely.
Your heart was pounding and as he pushed his cock even deeper into you. You screamed, unable to handle anymore but not wanting it to stop. All of that build up worth all of this.
Sam moaned as his hot cum spilled into you, his cock twitching as he eventually stilled, aftershocks of your orgasm still keeping you busy. Your pussy was so sensitive… and all you wanted to do was go back to your room and fuck yourself senseless.
“God.” you moaned as you finally opened your eyes. Sam was calmed down a bit now too.
“Y/N…” Sam said.
“Yes?” you responded as he looked up at you, still inside you, not wanting to move.
He kissed you, instead of saying anything else. And that kiss said it all. Maybe you’d had a small crush on Sam. But who wouldn’t? But now… maybe it was the sex, but you didn’t care. You wanted him, all of him, for however long you could have him.
“Shower?” you asked as you pulled away, still wrapped around him.
“Absolutely.” he smiled, and he let you down from his embrace, excited to continue this with you in any room that he could.