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As It Seems

Summary:

Thick leather boots, snug leather pants that looked like jeans, a leather belt and a leather chest harness with four belts that had double holes; all in black. The harness revealed a hairless but muscled abdomen and strong arms that made Dean nearly drool. The motherfucker looked like a leather daddy, and Dean's dick twitched within the tight confines of his jeans at the sight of the Dom.

"Hello, Dean," Castiel greeted, practically lounging on his chair. Dean gulped and dragged his gaze up the man's body to his eyes, flushing lightly at the amused sparkle within them.
--
It was supposed to be one Friday night, one quick and fun night of play; but then it turned into two nights and that turned into three... and four and five and six and after that, they just stopped keeping track.

Previously named: Best Shot

Chapter 1

Notes:

As It Seems
Best Shot

I think I just like making problems for myself. Sigh. Oh well. This is just lots of kink with a dash of aftercare and a hint of attraction. I have no idea where this is going and I don't really know if I'll find out but I'll try. Also, it's basically (almost) limited third person and it'll be changing between Dean and Castiel. So right now, this is Dean's Third POV.

Unbetaed and not proofread, pointing out mistakes (or inaccuracies with the binding and stuff) would be helpful~ Thank you! Enjoy!

Warnings are tagged at the end, and will always be tagged at the end.

(See the end of the chapter for more notes.)

Chapter Text

Dean

Dean stepped up behind a man with dark, messy brown hair and a lean build, clearing his throat to get his attention. "Name's Henry, you?" Dean held up two fingers, and the bartender, Benny, nodded at him, continuing to pour another man's drink. The man in front of him turned around, and Dean was suddenly attacked by intense blue eyes.

"Can I help you?" The man asked, raising a brow.

"Sure, you can," Dean shot him a charming grin. "You into doing a scene?"

"Depends," the man tilted his head, eyes darkening with something sharp and suspicious. "What do you want?"

"Anything you're into works." Dean grinned at Benny as thanks when he set down his glass of whisky. He picked it up and took a sip. "I'm assuming you're a Dom?"

"Yes, and I do not switch if you were wondering."

"Ah," Dean licked his lips. "I'd prefer to Dom but I'm cool with subbing. Wanna scene?"

The Dom tilted his head further, eyes squinting. Then he straightened and chuckled, lips quirking up in amusement. "Somehow, I don't believe that's true." The Dom picked his glass up and lifted it to his lips, throwing back the caramel colored liquid with a flick of his wrist. "What are you looking for?"

Dean frowned at the statement, wondering if he should be offended. "Just a whipping, or paddling. Anything like that."

"Sex?"

"Uh, if you want," Dean smirked.

"No, thank you." The Dom turned away, eyes flashing over to the only empty play stage. It was raised about a foot off the ground and had multiple bolts in the ground. And it was dark, none of the above lights on considering no one was there. "Go over to stage seven, remove your clothing, fold it and set it on the table, then kneel on the pillow." Stage seven was owned by the club owner's brother.

"Dude, we're not allowed over there."

"Boy," the Dom growled, disappointment clear in his voice. "I gave you an order. Follow it."

Dean clenched his jaw, nerves eating away at his insides. He could get in a lot of trouble if he went over there. "No."

"Then leave." The Dom began to turn away. "Either follow my orders or get lost. I'm not in the mood for a brat."

"I'm not-" Dean cut himself off and sighed. He chewed his inner cheek and stood from his stool, clearing his throat. Dammit, he was desperate. "Okay.. I'll-" He looked away and then started towards the stage, climbing up the stairs and walking to a table pushed against the wall and full of cuffs and chains and rope and whips and canes and so much more.

Dean glanced behind himself at the crowd that barely paid him any attention, and then back at the table. He removed his clothes quickly and loosely folded them, dropping them onto an empty corner of the table. He stepped away and moved towards a black pillow placed conveniently on the floor, he knelt down on it and folded his hands behind his back.

The moment he did, the lights above flickered on and multiple pairs of eyes flashed towards him, curious and shocked that stage seven was actually being used for once. He swallowed and bowed his head, closing his eyes. He breathed deeply, trying to push away the feel of their lusty intrigued gazes.

"Hey," Dean lifted his head and turned to the right, spotting a big, beefy security guard heading towards him. "You're not-"

"Leave," the Dom from the bar suddenly appeared behind the guard, and leveled him with a cool stare. The security guards eyes widened and he immediately looked apologetic.

"I'm sorry, Mr. Novak," he gasped, stepping away. He glanced at Dean and then hurried away, heading towards the hallway leading to the backrooms and offices.

Mr. Novak, huh? That meant this man was Lucifer's younger brother, James Novak. James walked towards him, and Dean realized he had taken his jacket off and rolled his sleeves up to his elbows. And damn, he looked a lot hotter. The stubble and bedhead and unbuttoned shirt and rolled sleeves made him look like an incredibly hot librarian. Christ, talk about a man worthy of a wet dream.

James stepped up beside him and Dean quickly lowered his gaze and turned his head straight, lowering it as well. James didn't make a sound as he walked around him, eyeing him with a gaze that was twenty percent approving and eighty percent judging. 

A hand stroked his hair, and he gasped, tensing and lifting his gaze. He felt the tremor of initial fear disappear and he flushed in embarrassment, lowering his head and eyes. James had an indifferent look on his face, like he was bored or disinterested.

"Stay relaxed, boy," James said, his gravelly voice sending shivers down Dean's spine. Dean nodded obediently, closing his eyes as the hand in his hair dipped down to the back of his neck and squeezed. "Good." His chest warmed at the slight praise. "Let's go over a few rules, boy."

The Dom let go of his neck, and walked around him slowly, his gaze heavy and strong. Dean forced his body to stay still and not twitch, clenching his wrist tightly to help himself. He heard a chuckle, from James, he assumed, and frowned, wondering if he was laughing at him.

"First, you shall address me as Sir," James began. "Second, you will only speak when spoken to. Third, you will do everything I tell you without hesitation. Fourth, we will be using stoplight. If you need to safeword, do not hesitate. What are your safewords?"

"Red, yellow, green, sir."

"Good, I'll be checking in with you every little while. I won't be using a gag on you, so there's no need to worry about non-verbal safewords. Do you have any questions?"

"No, sir."

"Hmm," the Dom stepped in front of him, revealing fancy dress shoes to his lowered gaze. "Stand." Dean loosened his arms, letting go of his wrist but not moving his arms to his sides. He stood and spreads his legs, once more grabbing his wrist tightly. "Hands out." He held his hands out in front of himself, palm down.

The blue eyed man moved his arms from behind his back, revealing a pair of padded black buckle cuffs with double D rings. He easily buckled them onto Dean's wrists, making sure they are secure and tight. The Dom stepped back, but Dean didn't lower his arms, there was no order given for such. After a moment, James smiled and began to walk around him again.

"You may lower your arms." He obeyed, letting them fall into a relaxed position on either side of himself. James walked in front of him again, with two more sets of identical cuffs and a cock ring. He knelt and made quick work of sliding the ring onto Dean's half-hard member. Then he buckled one set of cuffs just above his knees and the other around his ankles, all tight and secure. These cuffs were different than the one's on his wrists, while the wrist cuffs had D rings on one side - the inner part, the thigh and ankle cuffs had D rings on either side.

James stood and walked away again, stepping up behind him seconds later and adjusting a spreader bar between his ankles, forcing him to stand with his feet a little less than a meter apart. Then he attached another bar just behind his thighs, forcing him to keep his knees apart at half a meter.

"Color?"

"Green, sir," Dean answered immediately, breathing deeply. The Dom didn't reply, instead placing his hands on Dean's hips and carefully guiding him backwards a few feet then turning him around so they faced each other, and the crowd was behind Dean. He lifted Dean's hands one by one and attached the wrist cuffs to a chain hanging from above. A moment later the chain was lifted and Dean was forced onto his toes.

"I'm going to flog you. Do you have any places you'd rather I not hit?"

"Face, arms, below the knee and lower back, sir," Dean kept his gaze on the ground, still breathing deeply. James hummed again and stepped away, picking up a black and red Diamond-Handled Flogger - with at least twenty-five tails that were half an inch wide and square tipped - and testing it. He turned to Dean, stepping closer so he could see it properly. He flicked his wrist, letting him see the way it moved.

"Can you handle this?"

"Yes, sir." Dean shuddered as he slowly, lightly dragged it over Dean's stomach and thighs, allowing him to feel it.

"Good. You may be as loud as you like, but do not jerk around too much. I have exceptional aim but I would hate to strike you somewhere unplanned." It was a threat. And it was as much arousing as nerve racking.

"Yes, sir. Thank you, sir," Dean closed his eyes as James walked around him. He braced himself for a hit, but it never came. He kept his tense position until it hurt his body to maintain it, and so he slumped, unwillingly relaxing. A moment later, a sharp hit came across his thighs, and he moaned, his body jerking a little.

"Turn to the side." Dean struggled but managed to turn to the left so his left side faced James and the majority of the crowd. "Good." From the corner of his eye, he saw James pull his arm back and flick it towards him. He assumed it was headed for his ass, but he didn't realize it was going for the middle of his back. Dean grunted, hissing through his teeth.

The next hits were so random that they made his head spin when he struggled to think where they were going. James didn't increase the pressure one bit, letting the whip hit him with only a small amount of strength behind it. Dean couldn't stop the small whine that left him, and though he knew no one heard it, he still felt embarrassed for it. He slumped, letting himself be held up by the chain and not caring about the way the cuffs dug into his skin.

That was when the blows got harder, snapping against his skin with a hidden strength. He gasped, arching and crying out multiple times as he was thoroughly flogged over the outer and front part of his thighs, his stomach and chest and back. James didn't hit his inner thighs, his cock or balls or his ass. And it was incredibly frustrating.

Too soon, it was over. And James was walking towards him. He stopped in front of him, gently cupping his jaw and lifting his head. Dean blinked at him, panting softly. "What's your color, boy?"

"Green, sir," he rasped, watching a small smile spread his lips, disappearing as fast as it appeared. James let go of him, but Dean struggled to keep his head up so he could watch. James set the flogger on the table, and picked up a riding crop and paddle. He stepped up in front of Dean and held the crop up horizontal.

"Open." Dean opened his mouth and accepted the crop, biting down on it. "If it's too much, let the crop fall and safeword." Dean nodded in understanding. "Walk yourself backwards." Dean struggled but he managed to tiptoe backwards until he was forced to lean forward. "More." He bit the crop to stop a glare and obeyed. "Good."

The Dom disappeared behind him, and Dean heard the distinctive sound of chains. He glanced down at his ankles and watched as James hooked the chain to the D rings on the outer rings of the ankle cuffs before pulling them taut and attaching them to the ground, forcing Dean to practically hang in the air, only the very tip of his big toes brushing the smooth wood below.

It was hard to keep his body straight, but he managed to do a decent job. Or so he though. James didn't. James picked up a leather belt with rings and attached it around his hips, securing it tightly. He snapped his fingers and a moment later Dean felt chains being hooked onto the outside rings. His hips were raising into the air until the cuffs were pulling almost painfully on his ankles.

His ass was up and presented for all too see, set at just above waist height for a six foot man. Dean's shoulders quickly began to ache for the position and his hips hurt from the way the leather and a couple extra rings dug into the flesh surrounding.

The paddle touched his cheeks and he shuddered. It moved over each cheek slowly, stroking his skin, then it dipped down to his thighs. With feather like strokes it touched the backs of his thighs and the insides. Then it was gone. 

A hand appeared on his back, gently pressing into the warm skin, as if to sooth or ground him. Dean let his head hang between his arms and bit hard on the crop, breathing loudly as he readied himself for a hit. Dean heard it before he felt it. A sharp crack breaking through the air and slamming into him, his body jerked and then he felt an immense amount of pain on his right cheek. Dean groaned, tugging at the binds. He curled his toes as another identical hit came down on his other cheek, hissing through his teeth and the crop, his body jerking again.

Then, Dean was grateful for the hand on his back, because it made him feel safe and it told him to be still and good and it also silently asked him to trust James. He could trust James, if only until this was done. Dean closed his eyes and breathed heavily as another crack sounded and a hit came down on the back of his sensitive left thigh. A few more hits came down in quick succession, sending waves of pain and excitement through him.

Dean felt his body slowly becoming loose, and his mind began to drift. His worries disappearing and his thoughts becoming nothing. He slumped in his binds, suddenly grateful for the belt around his hips even if it dug into his skin and would leave bruises later. He was absently aware of the throb in his cock but didn't really care about it, more entranced by his ass than cock.

James stopped hitting him and just gently rubbed the paddle over his hot ass and thighs before disappearing. The hand slowly slid off his back and disappeared completely as well. Dean opened his eyes, staring down with a blurry gaze. He waited as patiently as he could, and he waited some more, and some more. But nothing came. 

Suddenly, there were multiple cracks in the air and immense and immediate pain spreading across his ass and thighs. Dean cried out around the crop, tears glazing his eyes and threatening to fall. The pain absorbed him, making him float and grounding him at the same time.

The Dom worked him over thoroughly, hitting the tops of his cheeks and his sit spots and his inner thighs. The hits were even more brutal on his ass than thighs, for which he was grateful and then not. He writhed in his binds, a few tears and probably snot and drool sliding down his face and neck and splattering onto the floor. And still, his cock was shamefully hard and throbbing and dripping precum onto his leg and the wood below.

Dean felt a new need building deep inside him, and another need being filled for the first time in what felt like years. James stopped paddling him and walked in front of him, cupping his face once more, stroking his cheek gently. "What color are you, boy?" He asked, flipping the paddle upside down in his hand and removing the crop with the same hand.

"G-green," he slurred, coughing and sniffing lightly. "Sir." Dean felt pleasantly high on endorphins, body loose and floating - literally.

James hummed in response, wiping away his tears. "Would you like to come?"

"Please," he moaned, trembling vaguely. James smiled indulgently and stepped away, putting the paddle away but not the crop. He returned and once more had Dean hold it in his mouth. Then Dean was slowly lowered and the belt around his hips was removed. He tiredly glanced up as his arms were moved backwards and half-watched as the chain pulled him back and up until the cuffs tried to pull him down and it was too painful.

He was only a foot off the ground, he realized, but it felt like more. The Dom stepped close and removed both spreader bars and the thigh cuffs and cock ring, dropping them onto the table close by. He then took the crop from Dean's mouth and swung it in the air a few times, testing. He looked back at Dean, locking eyes with him and grinned, ferally. It was then Dean suddenly realized the crop was firm tipped, meaning when it struck, it wasn't going to bend or anything of the sort, it was going to strike the designated spot and it was going to sting like a bitch.

"I'm going to hit your little cock until you orgasm."

James didn't ask if he was okay with it, didn't bother waiting for a reply. He just lifted his hand and slapped his cock with the end of the crop. Dean jerked his legs and tugged at his arms, arching his back and crying out at the sharp pain. The hits came fast and hard and felt absolutely divine. James hit his cock and balls and taint and his inner thighs, he even hit above his cock and his lower abdomen. And occasionally, when he went for his taint, he hit his delectably sore ass and it earned him a sharp cry and hard thrust. Sometimes, he switched sides, moving left and right, but he favored the right more - he was right handed after all.

The hits bordered on too intense, too much. But then James hit a spot just behind his balls and Dean just about screamed as he came. Head thrown back, shoulders and arms trying to come down and knees bending as he tried to curl in on himself. His cock jerked around, thick and long splatters of white shooting out and painting the wood white. He shook from pain and pleasure and moaned over and over, thrusting his hips continuously.

And then his legs were being uncuffed and body lowered, wrist cuffs quickly following the ankle cuffs and ending up on the floor. Dean was then wrapped up in James' arms and he buried himself into the Dom, shaking.

"Shh. You did so well," James murmured, slowly forcing him to walk and guiding him down the short stairs and towards the backrooms. He stumbled along, weak and barely aware and just wanting to curl up and sleep. James opened a door and led him towards a bed. He made him lay on his stomach - and though it hurt his cock and thighs, it was better than being on his backside - while he went to fetch some things.

Dean closed his eyes, limp and pliant against the sheets and very easy to take advantage of. He briefly wondered if James would, but then thought against it. The man didn't seem the type.

James came back and ran a hand through his hair. "Hey, come on. Can you get up?" Dean groaned and tried, falling back against the bed. James chuckled, or Dean thought he did, and then the bed dipped and shifted and Dean was being gently dragged up and into a pair of arms and against a warm chest. He sighed and tried to bury himself deeper into the warmth, rubbing his cheek against smooth fabric.

He felt something press against his lips and blinked his eyes open, staring cross eyed down at a small juice box that said Five Alive. He parted his lips and let the straw be pushed inside, then weakly sucked on it, his mouth exploding with different flavors and moistening. He swallowed and was quietly relieved when the juice soothed his sore throat.

He sucked and swallowed until there was nothing left to drink and then pulled his head away, licking his lips and relaxing against James. James stroked his scalp and neck, massaging gently and soothing him. Dean sighed softly and closed his eyes.

His muscles were sore, both pleasantly and unpleasantly. His lower half burned hot with pain and he felt every pulse his heart gave in his entire body. And his mind was calm and satisfied and the burning need he had felt for the past month was gone and replaced with a warm, satiated fuzzy feeling.

Notes:

Warnings: Spanking: Flogging, Paddling, Riding Crop. Cuffs. Spreader Bars. Chains. Suspension. Cock Ring. Public Scene. Aftercare.