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One of the few good things about having to dress up like FBI agents all the time was that suit ties did an excellent job of securing your wrists to the headboard of a motel bed. You and Dean were drinking the other night, made a bet –that you lost– and now here you were.
“I never took you for the dominating type.” you told him as you laid there already undressed as he tied you up.
“Well, if I’m being honest-” Dean began as he stood up to finish taking his own clothes off- “there’s somethin’ about you sweetheart.”
Your stomach felt as if it was doing back flips from his words and your eyes drifted south as he shredded his last piece of clothing, allowing his cock to spring free. You were certain you let out a whimper at the sight of him.. Dean was quite the sight to see.
If you had told anyone you were doing this, they’d think you were crazy. You and Dean were the best of friends, you got drunk together all the time, you made drunk bets with each other all the time, but…this time was different. This time, you both involved your true feelings for each other. Which neither of you had admitted to yet, even though you were about to have sex. Which would only make you both sound even more crazy.
“So what’ll it be first?” Dean asked you as got back on the bed and lowered himself over you slowly.
“I’m the one tied up Dean,” you swallowed thickly as his lips brushed against yours, “you tell me.”
“Alright then.” He whispered. You could tell that he might’ve been a little nervous - almost like he was afraid he might break you; and if you had use of your hands right now, you would’ve brought your hands to his face and told him that you weren’t as fragile as he thought you were.
Dean used one of his arms to support himself as he glanced down at your lips. Your tongue darted out to wet them as his green eyes bored into you. His free hand found your waist and without any prompt of you lifted your head up just enough to crash your lips into Dean’s.
He didn’t protest –though you knew he wouldn’t– and the second your tongue touched his, it was all over.
Dean’s hand slid up and cupped your breast, he settled more comfortably between your legs and his cock brushed against your belly. You bucked your hips up slightly, causing Dean to groan slightly as the motion massaged his cock. Dean kissed down your jawline until he reached the crook of your neck whenever he decided to reach down in between your bodies and tease your pussy by rubbing his length against it.
You were already wet, but feeling Dean push just the tip of his cock into your entrance made you even wetter. You pulled at your restraints and bucked your hips but Dean only held you down as he fucked you with the head of his cock.
“Dean.” you breathed just before you felt his teeth drag along the sensitive skin on your neck.
“Too much?” He asked before looking at you, not once stopping his agonizing teasing.
“Not enough.” you whined as he began to move faster.
“Well baby, I could do this all night if you keep soundin’ like that.” he smirked.
Your heart fluttered when he called you baby, but your pussy throbbed whenever Dean’s fingers ever so slightly teased your clit. His fingertips spread your folds as he stilled with the head of his cock still in your entrance, and flicked your clit with one finger. You pulled at your restraints again as your head flew back.
“Mmm, make me come.” you begged him.
Dean let out a low chuckle just as he pushed his cock inside you a little more. But still not nearly enough.
“Dean please.” you begged again.
“You tied up for nothin’ or don’t I get to have a little fun with ya?” He said, pushing his cock inside you a little more again, your walls slowly, very slowly, stretching to accommodate him- “I’ll make you come, I promise. I’m gonna take care of you.”
Just as he finished talking his finger brushed against your clit again, causing your body to jerk, and Dean pulled out until he was fucking into you with just the tip of his cock yet again.
It had been several minutes since Dean had first begun toying with you now, and you were panting, shaking, begging, whimpering, and mewling for Dean to do something more. Anything more. Whenever you body would tighten up just before you came, he would pull his hand away - only to stop your protest by capturing your lips with his.
Kissing was another thing he was incredible at. Each time he kissed you, it was like time would stop.
“You’ve been doing so good.” He praised you, kissing you on the lips once more before he pulled his cock and his hand away from your now dripping wet pussy. His lips were swollen from kissing and there was a thin layer of sweat on both of you, because even though he said he could do this all night, it was teasing him too.
You felt a warm wave wash over you whenever Dean started to go down on you. Your body was already responding to the change of pace and you lifted your head to looked down at him. His hands roamed your body and he took one of your breasts into your mouth. Dean swirled his tongue around you rnipple and flicked it with his tongue, making you crave more.
At this point you honestly didn’t care how Dean touched you, you just wanted him to touch you - period. And you only wished you could touch him.
After playing with your breasts he trailed open mouthed kisses down your torso, nipping and biting along the way. Dean didn’t have to tell you to spread your legs for him, you just did. And the moment you did, he wrapped his arms around your thighs to keep you from moving.
Dean made eye contact with you ask he kissed your inner thighs, and he smirked at you whenever he used his tongue - loving the way you jerked around under his touch.
“Dean-” you whined as your head flew back against the pillows- “please.”
You cried out a moment later when his lips connected with your aching pussy. His tongue darted out and he moved down to lick a long stripe from your entrance to your clit, then stopping to flick up and down with his tongue.
With each flick, your body jerked and your eyes squeezed shut as you began tumbling over the edge, not needing more than a few seconds before your toes were curling and you were letting out an involuntarily scream. The pressure within your lower belly had been so built up that it just exploded, clouding your mind with stars as you came.
“Oh god, Dean-” you cried as you squirmed- “we’re gonna get kicked out.”
“Then stop screaming.” He took a moment to say once you came down, flashing a smirk at you.
You didn’t say anything, or rather, you didn’t have the chance to say anything else before his mouth was back on you. He moaned as his tongue went for your entrance. He teased you and licked your walls and lapped up your juices while reaching out with his hand and very gently began circling your clit with his thumb.
“Dean-” you moaned again. What? You begged for an orgasm and now he wasn’t going to stop giving them to you?
By now you were certain your wrists would be red all the way around from how hard you were pulling on the ties that held you in place. You had to admit, Dean was good at tying people up. Had he been your captor, you weren’t so sure if you could break free.
His tongue went back to focusing on your sensitive bud - circling around it and making your back arch off the bed. Dean moved his arms so that he could simply keep your thighs pushed apart with his hands…and so that he could dip two fingers into your entrance. You did everything you could but Dean only held you down.
His fingers scissored inside you as he kept circling your clit with his tongue. Your legs shook and your lower belly tightened again and your hands gripped onto your restraints. You heard the headboard creek and you half wondered if you could just simply break the wooden bars off of the frame if it meant you could just thread your fingers through those short dirty blond locks of Dean’s.
Your breasts bounced as your back arched again and Dean’s free hand trailed up your stomach until he was gripping onto your breast. You tried to jerk away but he was swift with his tongue and followed every movement you made.
You came for a second time and this time you tried your hardest to keep your mouth shut as Dean squeezed your breast and as he buried his face into you even deeper.
If you didn’t know any better, you’d say Dean was enjoying this more than you were - and you were enjoying it a lot.
The erotic sounds of your wetness filled the room as Dean began curling his fingers up inside you. He removed his mouth from your pussy for a moment to look at you, too look at your overworked body. All he could think about was fucking you until you couldn’t move.
“You ready to take me sweetheart?” He asked.
You made eye contact with him, his face glistening with your slick as he smiled at you.
“Yes. Please.” you panted.
Dean kissed his way back up your body until he reached your neck and until you felt the tip of his cock at your entrance. You wanted to grab his face and kiss him, to feel his tongue against yours, to taste yourself on him - but again, the inability to move your arms prevented you from doing so.
“Dean.” you said before he pushed into you.
“Hmm?” He unlatched from your neck to look up at you.
“Kiss me.” you whispered, making eye contact with him. His usual forest green eyes blown black with lust.
It was almost like he saw something in your eyes, because he had to shake himself out of it before he leaned down to kiss you. You rolled your hips as your lips connected, encouraging him to push into you.
You only kissed him harder whenever his cock stretched open your walls. Dean of course moaned into your mouth, the man had basically been teasing himself while he worked you over. After only a moment, he could no longer control himself as he began fucking into you harder and harder. With one last kiss he sat up on his knees and pushed your thighs back, wrapping his arms around them to get situated.
You tugged on your restraints some more as you prepared for what Dean was going to do next. It came as no surprise whenever he started fucking you as hard as he possibly could. His cock brushed against your g-spot with every thrust, causing your walls to clench around him as your juices flowed out of you and around his cock and then onto the mattress. You started to scream again and before you knew it you were coming for a third time, without any clit stimulation. It took you by such surprise that you thrashed around as you clenched around Dean’s cock.
“God Y/N.” Dean groaned as his thrusts became erratic and he tried his hardest to keep fucking you but he stilled inside you involuntarily as he came undone. You watched his face as he came inside you and fuck if you could you’d come again.
But you were spent, and breathing heavily as Dean pulled out of you and immediately untied you. You couldn’t have moved faster a moment later whenever you grabbed his face and pulled him into a kiss. He laid down next to you and your body moved with him.
Dean’s hand found your waist and pulled your close as you kissed him. You were worn out but at the same time you wanted nothing more than to roll Dean over onto his back and make love to him.
“Dean.” you said as you forced yourself to pull away. It was time you fessed up.
“Yeah?” He breathed, obviously still just as worked up as you were.
“I lost the bet on purpose.” you admitted.
“I know.” He smiled before leaning in and kissing you again.
You smiled with your lips against his as you realized that this was only the start of something amazing.