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Punishment: Part 24 of 6

Sans entered the bedroom. Chara was already waiting, her clothes off. She smirked at Sans, her red eyes eager.

Sans swallowed back the panic threatening to overtake him. He slowly slipped off his vest and pulled off his pants. Chara watched him undress, transfixed by him.

Shaking a little, Sans crept into bed next to her. Chara looked up at him, her crimson eyes filled with lust.

"You look so handsome, dear." She whispered seductively, tracing a finger down his spine.

Sans shivered as her hand traveled along his spine. He was so scared; what would she do to him this time? But he had to play along. He had no choice.

Sans pushed her down gently onto the bed, teasing her by rubbing up against her clit. She gasped, crimson eyes becoming dazed with need.

Taking a deep breath, he slowly began to force himself into her, letting her adjust to his size. Then he started to move. Chara keened with pleasure, wrapping her arms around him.

"H-Harder!" Sans swallowed back his revulsion, pushing himself even more forcefully into her, sweat beading on his skull from the effort. He leaned down and and gently ran his teeth against the side of her neck.

Chara moaned ecstatically, squirming underneath him. He was really good at this. Her black tentacles manifested, slithering up Sans's body and wrapping around him.

With a sickening "crack", Sans's left leg broke. Sans cried out in agony, tears falling down his face. He paused his motions, pain blanking out his mind.

"Why did you stop? Keep going!" Chara demanded, glaring up at the trembling skeleton. The tentacle set his broken leg back in place with a "snap", making Sans cry out again. The pain was almost too much, but somehow, he still managed to stay conscious. Green energy began to flow from the tentacle to his leg, healing the break.

Chara smiled. "Good boy." She purred. "Let's see how long you can stay awake."

(A few hours later)

Sans lay underneath Chara as she thrusted harshly into him. One of his arms and legs were broken and his entire body was spotted with minor cuts from Chara's sharp tentacles. Everything hurt so much: his broken limbs, his cuts, the motions from Chara. Tears streaked down his cheekbones as he whimpered against his tormentor.

One of Chara's tentacles entered Sans again, pulling roughly in tandem with Chara's motions. Sans screamed in intense pain. All of the pain from before seemed minor compared to the sharp tentacles.

"M-Master, please!" Sans cried, shaking. "Please st-stop! I-I-It hurts too much!" He hated begging to this sadistic jerk, but right now, he felt like he'd do anything to make it stop hurting.

Chara stroked his face almost tenderly, kissing away his tears. "I want you to remember this pain, so that you will know you are mine and only mine." She loved seeing him scared, his beautiful voice screaming in pain as he begged for her mercy. It made her heart flutter in excitement.

"I-I'm sorry, master!" Sans sobbed. "I-I won't do it again. Just pl-please! Stop the pain!"

Chara retracted all her tentacles and pulled herself out of Sans. He lay there, weak and shivering.

".2 HP." She thought, checking over his stats as Sans barely held on to consciousness. "Still room for a little more."

Chara bent down, licking Sans's neck and finding his sweet spot. Sans moaned weakly and trembled at her touch.

Suddenly, she bit down. Hard. Sans cried out painfully, flailing weakly against her hold. She bit down deeper into his neck. Sans screamed, but he was too weak to shake her off. He could only cry, his tears dripping down his face.

Finally, Chara let go. She licked the blood off her teeth. Sans gasped painfully, his breathing shallow. Blood dripped down, staining the bedsheets red.

Sans stared off into the distance with glazed eyes, his sockets closing as he finally fainted from the pain and blood loss.

Chara smiled down at him, feeling accomplished. But she was really tired. They had gone at it for a long time. "I'll heal him tomorrow." She relented, and fell asleep next to Sans.