Crowley’s face was stretched with a wide smile, he could not keep his maniacal laughter silenced. He couldn’t help it, he had always loved giving a needy sub a good beating. He loved hearing a pathetic little being tell him that he needed to be taken, to be hurt, and with that he would never complain. Crowley would never have guessed that Dean would be the submissive type, but he was quite pleased when he realized he was wrong. Crowley had taken up a second job of sorts after finding out that Dean Winchester craved extreme pain and punishment by another’s hand.
Over time, their encounters ranged from brutal torture sessions resembling what Crowley gives to the damned in Hell, to purely sweet caretaking sessions. At first, Dean was completely afraid to voice what he wanted, needed. Crowley had to coax the beautiful words out of him, had to build up a strong relationship built on trust. Dean had looked so beautifully pathetic, stuttering after he called Crowley, “Daddy”. After Crowley gave him a positive reaction, along with the token, “tell Daddy what you need”, Dean spit out everything he had been holding back before, his needs, wants, explaining he had next to no limits.
Crowley gave a hard pat to the chair that raised Dean up to eye level. He had grown quite fond of perching Dean up on the chair before laying into him. He had started to call it the “punishment chair”, which made Dean stay far away from it unless he was forced to. Dean avoided eye contact as he climbed up on the chair. He looked down at their pairs of feet, Dean without shoes, without socks, and Crowley fully dressed with his shiny black, pointy, dress shoes. He let out a little moan at the show of power imbalance. Crowley just examined him for a moment, smiled fondly, then snapped at him and barked, “look at me, Dean”. Dean realized this was when the show would officially begin, Crowley rested a hand softly against his cheek, wiping away tears he hadn’t realized had fallen. Crowley gave him a light kiss on the forehead and reassured him, telling him, “you know this is because Daddy loves you. This is for your own good, Daddy knows what’s best for his baby”. Dean whined a little, squirming uncomfortably in the chair as his cock had already started to harden in anticipation.
Crowley dropped the sweet demeanor, his eyes flashed red as he gave a mocking whine and mocked Dean for being a pathetic, needy little baby. Crowley’s left hand shot up to Dean’s neck, choking him with the red in his eyes burning bright. With his right hand, he gave Dean a good slap to the face, then another and another. Dean’s body was wracked with sobs by this point, he couldn’t get out words, and he could barely breathe but he knew this was only a warm-up. Crowley stepped back, removing both hands from his face and letting Dean sway forward into him a bit. Crowley swung and connected his fist with Dean’s face, hitting him hard. Dean cried out and swore, Crowley not relenting. He punched him in the same spot two more times as he exclaimed his love for Dean. He put one hand on each side of Dean and pushed him backwards, which caused him and the chair to go tumbling back into the couch. Crowley swiftly kicked the chair across the hardwood floor. He took a step forward, grabbing Dean and punching him in the mouth until blood dripped down Crowley grabbed Dean by the hair and pulled him so he was standing straight. He gripped his arm tight to keep him standing and leaned forward so he could lick some blood off the side of Dean’s face.
Dean whined and Crowley kicked his feet apart and rubbed his hand against the hard bulge barely hidden in Dean’s boxers. After giving Dean a little bit of relief he stopped, pulling his hand away. He tsked at Dean as he heard him whine, replying with, “oh you want to be greedy? Fine I’ll give you something to fucking whine about”. He pushed on dean’s shoulders so he dropped down onto the hard ground in front of Crowley. Crowley ripped apart his pants, pushed down his boxers and pulled Dean’s head forward until he felt the tip of his cock go down his throat. Dean cried harder, the pressure hurt his injured mouth even further, but he was trying to focus on being good, no biting and no throwing up. It worked for a minute, until Crowley decided it wasn’t enough and held Dean’s hair and fucked forward hard and fast. Dean tried controlling his gag-reflex, until Crowley held Dean flush to him so he couldn’t even breathe. He gave in and gagged, pulling back and slightly puking on Crowley’s cock. Crowley allowed him a second to catch his breath, then pulled him back while groaning and praising Dean, “You’re such a good boy for your daddy, poor little thing can’t take Daddy’s whole cock huh? Is it too big for a little baby like you? It feels so fucking good when you puke on me baby boy, your little throat gets so fucking tight around me”, all while he continued to fuck Dean’s throat. Dean gagged once again but this time Crowley held him forward so he couldn’t pull back, he choked further and spit up over himself and Crowley. Crowley gave him a hard slap across the face and finally came into Dean’s mouth.
He pulled Dean up onto his feet, not giving him a moment to steady himself before he shoved him onto the couch, but Dean wasn’t close enough so he fell mostly onto the floor. Crowley knelt in front of him, already fully dressed again, laughed at the sight of blood and puke covering his bare chest and the tent in his boxers. He knew better than to ask Crowley to let him cum, but he needed it, he couldn’t help it, he shyly asked permission to cum. Crowley’s eyes flashed red, he stood up and spit down on dean, giving him a swift kick to the stomach. Dean started to cry again, breathing heavily, trying to catch his breathe, he looked up and pleaded, “Please, Daddy, please. It’s been so long, Please Daddy”. Crowley rolled his eyes, put his foot out in front of Dean, and responded, “if you want to cum so fucking bad, you can rub up against my shoe until you do, but you also have to clean up your damn mess, Darling”. Dean nodded and with a smile, he quickly lunged forward and rubbed himself against Crowley’s foot, cumming quickly. It caught him by surprise and it pained him, but that only made it better. He then bent down and licked the cum off of Crowley’s shoe, showing Crowley his prize on his tongue, then made a show of swallowing. Crowley laughed, called him a good boy and a slew of other affectionate pet names that never failed to make Dean blush, even though he’d heard them thousands of times.
Crowley picked Dean up, kissed his face like a toddler kisses a dog, and carried him to their shared bed. They held each other uncharacteristically lovingly for a while, Crowley repeating how good Dean did, how he was a good boy and how he loves him very much. Dean latched onto Crowley like a koala, cuddling him like his life depended on it. He always needed a lot of comfort after any rough stuff, Crowley always wondered if that had anything to do with a traumatic event that happened in his life. As Dean dozed off towards dreamland, Crowley shook him off enough so he could be facing him, he gazed at his face, looked at the bruises that were already starting to form beautifully, he laid his fingers lightly against Dean’s bloodied forehead and cleaned him off. Crowley found that it was easier to clean up his way rather than the slow, power-less, human way. He laughed to himself as he saw Dean’s now cleaned face only littered with bruises against his slightly pale pink skin. He snapped his fingers, summoning a lowlife demon who worked for him, told him to clean up their play area and set things back up like they were supposed to, and told him to prepare a light, warm meal for Dean for when he woke up.