He was tempted to scream, but the only noises he'd made since it began were the worst kinds. Fingers grasped the edge of the wooden frame, an opening he'd once gone over to avoid the confrontation of the hunter on his tail. But now it was something to hold onto, to brace himself. The worn red painters uniform he'd started this trial with was shredded at his hips, torn open so the hands that claimed him, embraced him and held him still could see the prize fully in front of them. His narrow hips were spread so wide he felt like he'd never be able to walk again, it had been an agonizing experience to let such a thick length push through between his cheeks and into the heat of his body. He would have taken a knife, a sword, even a club over this shame and torture. That deep hum had now turned into dark chuckles, breathless gasps of pleasure, light tickles of enjoyment as amusement dripped off the man. His feet couldn't even touch the ground, his body impaled on the shaft that drove into him repeatedly, letting Edgar feel the full length of the monstrous creature before pulling out to the tip. Whatever neat locks of hair were previously tucked under his cap had fallen loose over his forehead, the paleness of his skin now scarred with a brilliant ruby. If only he hadn't been the last one on the map, if only he had played his cards safer.

The clawed embrace of the hunter dropped from Edgar's hips to shift their positions. The young man could only cry out, a complaint as his legs were hoisted by his side, that window looking out at the misty grounds was the audience of their entanglement. "Such a skilled performer deserves the best of prizes, wouldn't you say?" A silk undertone of mocking flowed from those masked lips and Edgar could only look over his shoulder at the hunter with a look of horror on his face. In this position, the world could see Edgar's legs spread, could see the cock nestled too perfectly inside. Despite the original fear that his body would tear in half from the act, somehow it also managed to grow accustomed to the limb. His back was pressed to Jack's that muffled breathing overlapping with his own as he let his head lull back just enough to look at the ceiling. He knew he had been a bad kid growing up, and now that he was older, he hadn't changed very much. But coming to this hunting game was his choice, his need to find some kind of inspiration. Instead, he learned that the only thing he was good for was entertaining this murderer. Jack seemed to slow, managing to catch on that Edgar was losing focus. There was no growl, no hint of annoyance, they were like minded- an aspect he was ashamed to admit.

"Inspiration is the key to any creative experience… so let me aid you." Edgar made a noise which quickly turned into a shocked gasp as that clawed hand that had taken off half of his clothes raked down his front. Pain, it suddenly exploded in his nerve system as he stared down at the wound starting from his right shoulder and down to his left hip. "H-How…!" Panicked tears began to form, he could take being used like this, take being hunted, but this kind of pain was not what the high class system readied him for. "Allow me…" The Ripper replied with a hidden smirk. The pair moved two steps to the left where there was no longer a window but instead a blank wall. Edgar was too focused on the mess of his uniform and body to really pay mind until he was forced forward, back down so his hands had to brace him at the wall for fear of falling forward onto the ground. A strong arm kept him up, clearly their escapade wasn't over and it was accompanied by a forceful thrust that left Edgar's toes curling and breath hitching. He bit his tongue, never wanting to let the man see the pleasure that he caused. "What exactly are you doing!" The brat hissed, looking over to the best of his abilities at the shadow of a being behind him. That mask was still present, still hiding the features of the man that seemed to care a lot for Edgar's well being… at least in regards to pleasure. A hum was his answer and anger flared in his chest. "You don't even give me a direction, you just take me like I'm yours without even showing me your face!" He kicked out in desperation, the original fight between them starting up once more. That deep chuckle echoed through the rundown shed and whatever the painter was trying to achieve by fighting him was once again nullified by a hand grabbing the back of his neck and forcefully straightening him up. Jack was bigger, taller and had incredible strength, in some ways it made Edgar wonder if this would end in his death. He growled out through gritted teeth, seething. "If that's all you need…" That sultry tone was back as Jack began to lean into Edgar, removing his hand from the back of his neck. "Let me guide your hand in this creative pursuit..." Edgar could hear the distinct sound of leather clasps coming undone and his sapphire blue orbs shot towards the one behind him, trying his best to see as Jack the Ripper finally removed his mask.

Whatever Edgar had expected, it was not that, and it caused the boy to turn back towards the wall. Luckily the colour had remained on his face so it would not give away the physical reaction… from what he knew. A laugh and Edgar did a double take, seeing the flash of fangs in the handsome man's mouth. "Clearly you like what you see…" He leaned in and Edgar looked away, staring ahead at the blank wall even as the dark one brushed his lips against the teen's ear. "You tightened right up." How blunt! Edgar would have scolded him if Jack didn't take advantage of the shock to thrust deep inside. Edgar couldn't hold back the moan that followed, causing the swelling of pleasure inside to grow ever faster. "Please…" He began to whisper, he was growing tired of this game, he was growing used to Jack being inside him, it was embarrassing… he didn't want to beg. "Please just take me…" He whined with his feeble attempt to squirm by kicking his dangling legs out. Jack continued to look amused, like a cat finding a mouse backed into a corner. "Ah, but that would ruin our precious moment and I do look forward to seeing you on the field… in fact I will now make sure you're the last every time, little one." His declawed hand dipped under the painter's torso to touch the bloody mark. "Now I've given you a canvas… I've given you inspiration… the tools are before you if you can manage." Manage? Edgar opened his eyes to blink, manage to paint now!? It took a moment for his brain to catch up with what Jack was implying but as soon as he did, his mouth opened to protest. However, Jack was also willing to fight back if Edgar refused. His hand trickled up Edgar's chest to his throat and soon the teen found it difficult to refuse, difficult to even breathe. "I don't like repeating myself, little painter." The words were purred out even as the colour in Edgar's face began to drain. "Don't worry, your reward it only moments away… if you comply." He managed to nod, making a small straining agreement sound to let Jack know his choice and therefore the hand dropped and the thrusting commenced.

"D-Damn you!" There was a hesitancy in his motion as his thin fingers went to his chest, to the very wound that mixed pain with pleasure so fluidly. Wincing as his body was forced more against the wall, an elbow acting as his only brace. Red tinted fingers went to the old wood and Edgar fumbled with the crude drawing. This wasn't meant to be training or some way to better himself, this was fun for Jack and nothing more. To have this young survivor bent over against a wall, painting the very scene with his own blood must have given him all the joy.

Once the last line was drawn and the worst sketch was revealed to the pair, Jack let out another series of laughs that were no longer muffled and no longer held back. "If I had known you were this amusing-!" Edgar gasped as he was pulled off of the length but his small body did not get a break, instead, he was thrown across the wooden boards, tumbling until he couldn't roll any further. Naked from the waist down, Edgar tried to force himself up, tried to get his legs to work but by the time he even managed to move onto his side, a hand grabbed his ankle and he was lifted by his leg towards the kneeling hunter. Back onto the tip, letting the thick limb enter him once again, Edgar's nails clawed at the floor as a scream ripped from his throat. "Louder!" There was something wrong, something off about Jack now as those crazed eyes bore down on the small brunette. But he barely had time to question before the man impaling him shifted his form, at least his left arm into glowing gold tendrils that lashed out at his face, taking the second Edgar opened his mouth and using it against him.

Muffled screams could be heard outside as crows flew up into the air. Just like the cock mercilessly spreading him further apart with each thrust, whatever airflow that Edgar could manage only happened after the tentacle pulled out then went back down his throat. It covered his lips, partly wrapping around his neck, pushing him into the floor where Jack could get leverage to pound into him. Tears leaked out of the corners of his eyes as the pleasure mounted to an unbearable pressure inside. Suddenly he screamed again, but it was he who coated his front with the white of his juices. "Good boy~" That silk voice sung, though he was hardly finished. The hunter used his normal hand to grip the teen's hips, forcing them up to meet him as he thrust down onto the poor painter's body. Whatever limb was entering from the mouth now reached further down Edgar's throat, as if trying to meet the other side without killing the boy. With the cum mixed with the blood and the sight of the human at his mercy, Jack finally let out a soft, low moan as his climax projected into the other's form, claiming him finally after days of chasing.

Pants were buckled back up and the tentacle was shifted back into a claw, though Jack got up from the floor, Edgar wasn't moving. For a second, concern flashed through those deadly crimson eyes but when he saw his chest rise and fall, that emotion disappeared. A small sigh released from his lips and a tinge of a smile crept onto the youthful face. "Already out cold… poor thing." The hunter was tender as he lifted the young creature up into his arms, a head resting against his chest caused a flurry of emotions to spread throughout his form as he carried Edgar outside. Now what to do with him… Jack glanced at the open door, the way out, the only way Edgar would be able to escape - and never see Jack again. He hesitated, that soft moment between them was clouding his judgement. He knew what the right thing to do was but…

Jack walked over to the chair, wishing there was a less aggressive way to send Edgar home, their home. He admitted that letting Edgar go back to his people and his life was the proper thing to do after everything, but the idea of never being able to see the young painter again… it was too hard to say goodbye to things he wanted to keep. Securing the small frame against the chair with the harness in front, Jack took a step back as the chair activated. Blue eyes only opened in time to see a faint smile and hear a whisper from those normal concealed lips before he was rocketed back to the manor.

"Until next time, little love."