Dean's head hit the wall hard, causing an ache but it was an ache he preferred to what Azazel was doing. An overwhelming need to vomit washed over him like a wave of ice water as he watched Azazel lean into him, watched him lick his lips and cringed to such gestures. It made his skin crawl and the pit of his stomach churn like rancid butter. His lip curled up a little, disgust on his face to the sort of eyes Azazel was making at him in his father's body. It was almost more than the demon could take: the pleasure in how it was making Dean squirm was almost torturous. He let his eyes drop, running his gaze down Dean's face with a sensual intake of breathe. Dean was a stunning example of Humanity: Strong jawed, fine featured. His lightly tanned skin currently adorned with cold sweat and the dirt from the struggle. Every inch of him was muscle, a defined and well crafted body. Azazel was almost sorry that it wasn't Dean he was steering, but that wouldn't much fit into his plans for tonight. Couldn't break Dean by driving him, for Dean was a martyr and would no doubt prefer being possessed to watching his family in the same position.

No, what he was going to do would be so much more damaging.

Sam was now growling from his perch on the other wall, watching Azazel torment his brother with suggestion. It made him feel equally sick. His breathing was still heavy and laboured as he pitted his muscle against the demon hold on him, without any affect at all. Soft grunts and groans from him spoke of his struggling, his anger, and how much Sam clearly wanted to rip him away from Dean. Sam was a fighter that was for sure, no diplomacy in this man, just war. Dean clenched his jaw, his expression remaining disgusted but turning a little harder as he starred Azazel right in his butter-yellow eyes and growled sternly.

"Do it already."

Dean wouldn't give him the pleasure of making him nervous, making him turn his head. He sure as hell wasn't going to beg him to stop, wasn't going to whimper and bleat like a goat on the slaughter table. Fuck that. If Az' was going to play these twisted games, Dean would let him. And endure. Because that was how Winchesters did things: they endured, and they remained solid. Azazel grinned nastily and quickly, before he obeyed. He pressed John's lips firmly against Dean's, raising his hand to Dean's cheek as he guided Johns body against him, engaging Dean in more than a simple kiss. Pressing the manly frame he currently had hold of against the younger Winchester, he couldn't help but half smirk through the kiss, allowing a faint moan occasionally so no matter how hard Dean clamped his eyes shut he could still hear his father's voice as it vibrated up through his mouth. Dean's face scrunched up, his expression repulsed and his eyes shut hard but he didn't falter. He reminded himself this was not his father, but even that thought brought him little comfort. He was still lip-locked with a demon, a MALE demon. Johns stubble was painful against his chin, like sand paper, and left rough red scratches. None the less, Azazel was not breaking him, Dean even found it in himself to kiss back a little although it made his expression worsen to do it and near made himself gag. Deans own personal 'Fuck you'.

Azazel drew back slowly, having expected much more of a struggle from Dean. He'd been surprised at Dean's endurance of it, surprised he hadn't buckled and pulled away. He was harder to break than he had anticipated. The somewhat disappointed demon let his head lull back and starred at Dean, who was now open-eyed and starring straight back defiantly. That defiance was going to get him into more trouble than it was worth. Yellow eyes folded John's arms across his chest, frowning as he pondered the taste of Dean, which had been – wholesome. Sam had gone quiet, and although he hadn't looked, Azazel assumed it was from shock. Producing a smirk across John's face after a few seconds, Azazel raised a brow.

"Enjoy that, Winchester?"

Dean would have shrugged, if he could move at all. Hell, if he could move at all he'd have punched him.

"I've had better."

Another smart arsse comment.

Sam had been starring open mouthed, Shock having chased him to silence and more controlled breathing as he watched his father and his elder brother with a look of sickened horror in his deep green eyes. He was stunned into an almost numb state of mind, his brain still processing what he'd just seen Azazel put Dean through, and how Dean was handling it. If his brain was functioning on any level except sheer flabergaspery, he might have felt impressed by his brother's strength. He'd certainly not have given the same reaction.
Azazel's soft chuckle was louder this time, the demon mutilating a laugh that was usually hearty and amused into something sinister, with intention. It just didn't sound right on John. Again, Dean reminded himself this was not John, not in the slightest. Stroking the line of Dean's cheek bone with his thumb somewhat affectionately, he took a good look at his face. That pretty face. It wouldn't be so pretty in a moment.

Azazel turned a moment, looking around at the room, noting where things on the walls were: Hooks, nails, old picture rails, chains. Smirking, he turned back to his prize. Reaching up he took hold of Dean's top and ripped it open at the front, all the way down, repeating in other directions until he could pull it off him.

"...I'm sorry to hear that."

He muttered. His hand was on Dean's throat before the Winchester registered it, lifting him off the wall and marching him across the room, to where old picture hanging nails still protruded from the walls. Holding him up, he pushed Dean's back up against the wall, slowly forcing the blunt ends of the nails to break the flesh on his back and push into the muscle. This drew a very satisfying couple of winces from him as Azazel eased the Cm long blunt spikes into him. Blood trickled down his back from the two puncture wounds. Dean clenched his jaw as hard as he could to stop winces becoming screams, concentrating on keeping his whimpers to a minimal. Azazel held him there for a few seconds, before starting to lower him, the nails dragging up his back, tearing his flesh open and causing blood to pour down instead of trickle. This made Dean scream. He could feel his back tearing open like a Christmas present. In the dim light Azazel's eyes flashed with enjoyment. The smell of blood, and the sound of that scream did more for him than was considered healthy.

The scream tore Sam back to reality, and he started to growl and shout, swear even as he watched the blood flow freely from the large deep gashes on his brothers back. Azazel turned his head to look at Sam, grinning like a maniac as he lifted Dean off the nails, throwing him to the floor before Sam.

Dean could barely keep himself up on all fours. His now exposed back told Sam all he needed to know as to why. Deep claret rips in his skin about 9 inches long were still oozing vast amounts of blood that was running down either side of Deans flanks now, having already left a waterfall trail down towards his belt line. Strips of torn muscle were exposed; no doubt meaning Dean would have trouble standing even if he could. He was shuddering on the floor, trying to control the pain and the accompanying sickness that came with it, trying to fight off on-coming shock. He could smell the blood in the air, thicker than damp smell the room already had.

Azazel sauntered up behind Dean, looking straight at Sam now as he stopped and plunged his hands into his pockets.

"Wanna help? Hm? Well, I tell ya what..."

He pulled one hand free from his pocket and gestured to the cult still lying on the table to the side of Sam.

"...You can help any time you want. All you need to do is pick up that Cult, and shoot."

Mocking Sam, knowing he wasn't strong enough yet. He couldn't pull himself out of the demon hold, and even if he could, he wouldn't shoot dear old dad. Looking down to the mess on the floor before him, he sighed dramatically.

"Looks like Sam isn't playing today, Skippy. Just you and me."

He brought his foot down hard on Dean's back, pushing him to lay flat on the floor. Dust and dirt from the bottom of his shoe mingled into the wounds, making them still more painful and drawing more winces, this time accompanied by a mumbled 'ima-kill-you-you-sonova-bitch'. Leaning down as he lifted his foot off him, keeping him down with demon hold, he eased Dean's blue jeans down to his knees, getting a mumble from a worried but agonised Dean. Sam watched with increased horror as Azazel made easy enough work of Johns Belt, and unzipped his flies.

"What are you doing?"

Sam's voice betrayed his disbelief, his disgust, his horror as he watched. It was all he could do. Azazel eased John's jeans down a little until they hung low enough on his hips for the open flies alone to be enough exposure.

"No...No no..."

Sam muttered, with increased volume as he became to realize what Azazel was going to do. Azazel simply lifted his head, pointed at the Colt a second time, and smiled.

"You know what to do..."

He then dampened his fingers in the blood on Dean's back, drawing painful twitches from the oblivious Winchester whose head was swimming with the pain and the blood loss. He wasn't so numb though that he didn't feel it as Azazel's blooded fingers brushed over him in a most unwelcome spot. His body went into spasm in panic, but was unable to move. The demon then went about coating John's member in the same fluid, which he was thankful to have control of. Were he not steering all parts he doubted this would even be possible. Ignoring further shouts from Sam, Azazel leant down over Dean, smirking, whispering to him.

"I ought to do you dry, be thankful I'm a charitable sort o'chap..."