Alright Guys here it is… The chapter you have all been anticipating! I hope I did a good job with this and this will probably be the most sexual it will get (But I may still have a few surprises up my sleeve for future chapters) so I hope you enjoy and please don't forget that I won't be able to update everyday anymore because of school. I really hope that you all enjoy this chapter and please review, follow, and favorite!

*WARNING: Non-Con, Language!

"Oh Jack," Pitch chuckled darkly as he turned his attention to the frightened winter spirit, "It's my turn now…."

Pitch snapped his fingers and the nightmare sand dissolved, causing the winter spirit to fall weakly to his knees.

"Oh my god Pitch… not that! Please," Tooth screamed as tears streamed down her face. Pitch waved his hand annoyed over Tooth as his back sand wrapped around her mouth, efficiently gagging her.

"Tooth!" Jack screamed out as the nightmare king towered above him.

"Don't worry Jack, I won't touch her anymore as long as you behave yourself…," Pitch sneered as he ran a hand through the spirits white hair.

"Fine, as long as you don't hurt her again!" Jack wasn't even listening to himself anymore… he wasn't thinking about what was about to happen to him; all he cared about was keeping Tooth out of harm's way, even if that meant he would be the one that would be getting injured even more, "What do you want me to do?" The winter spirit hissed through his gritted teeth.

Pitch grinned sadistically as he began to slowly remove his black robe, "I thought you would never ask…."

Jack quickly caught on to what the Nightmare King was about to do. Before he even had a chance to scream out, Pitch filled his mouth with his cock. The Guardian's throat burned by the sudden impact and pressure being shoved down it as Pitch's manhood stretched his mouth wide and made his jaw ache. The Nightmare King laced his fingers into Jack's frosted hair and slowly began thrusting his head until it was in sync with his hips. Moans of pain escaped the winter spirit as Pitch continued to buck his hips, shoving his hard cock further down Jack's raw, burning throat. The Guardian of Fun could tell that Pitch was reaching his climax as he his sharp nails gripping his hair began to dig lustfully into his scalp. With one final thrust, Pitch shoved all the way into Jack's weak mouth, gagging the winter spirit as he came. Jack couldn't breathe… he coughed and sputtered against Pitch's cock as his black cum dribbled out of the corners of his mouth. Pitch released his grip on Jack's hair and the winter spirit fell to the floor as he choked on the black cum he was spitting out, trying desperately not to swallow.

"Don't start throwing a fit now, Jack… the fun is just about to start," Pitch laughed venomously.

Jack was beginning to hate that word… Fun! Coming out of the Nightmare King's mouth, it sounded like the most evil, terrifying word, and Jack hated it! He knew this was what Pitch wanted… he wanted Jack to resent the very thing he swore with his life to protect. He would steal away all the innocence, purity, and fun out of the spirit until he was as cold and barren as the winters he creates. The worst part of it all was… it was working! Jack no longer felt like the happy, mischievous spirit of winter that everybody knew him to be… he just felt broken, impure, and empty. Cold tears of shame welded up in his eyes and began rolling uncontrollably down Jack's bruised cheeks.

"My, my Jack… for a virgin you sure seem to know what you were doing," Pitch cooed, gripping the winter spirits chin and forced him to look in his eyes as he brushed away his tears with his thumbs.

"I-I don't… Stop talking like t-that!" Jack choked out as he closed his tear-filled eyes and tried to jerk his chin out of the Nightmare King's grasp, but his sharp nails just dug into his cheeks and drew blood.

"You can try to fight it Jack," Pitch hissed into his ear, "But it is going to happen… you're mine!"

With those words, tendrils of Nightmare Sand shot from the shadowy wall of the cell, tangling themselves around Jack's pants, tearing and shredding at them as they tugged at the Guardian's limbs, forcing him to wrap around Pitch as he hefted up against him, pressing his back against the cold wall and tying his hands above his head.

"Are you ready to lose your virginity, Jack?" Pitch asked cruelly pinning his body up against the fully exposed Guardian.

"Tooth," Jack begged through tears, "Please look away!"

Tooth nodded weakly as tears slid down her soft cheeks. She regretfully closed her eyes and looked away from the trembling spirit, not wanting to see what was going to happen to him.

Nothing could have prepared Jack for the pain he felt as Pitch entered him. His felt like he was on fire as a searing pain shot throughout his body. Jack let out a bloodcurdling scream as he felt the pulsing of Pitch's cock inside of him. Pitch kissed Jack's neck and grinned as spirit shuddered beneath him. He loved feeding off the intoxicating fear Jack produced, but he had never sensed it so strongly and so intimately. He roughly thrust against Jack as he softly moaned in pain. Hearing the soft sound made Pitch growl softly in response and jerk his hips entering the small spirit's body even further. Jack was so tight and delicious, that it made the nightmare king crave for more of his perfect body. His mouth began to explore the guardians pale neck and in a matter of seconds, he discovered a spot on Jack's neck that was more than sensitive.

"P-Pitch!" Jack moaned when he felt his lips brush against it. Pitch gave a wicked grin – he knew exactly what it was doing to him. "Pitch, o-oh my god," he hissed through his teeth. Pitch continued to suck on the spirits sensitive spot as he began thrusting even harder, becoming more and more aroused by the young Guardian's constant cries of hated pleasure.

Goddamit Frost, Jack's conscious scream to him, He's the Nightmare King… he's your fucking enemy! Why are you allowing him to get to you like this! He's stealing your virginity and all you can do is just let him…? You're not even trying to fight back or stop him! Think about Tooth! Think about the Guardians!

Jack's mind and body wrestled with each other; fear over pleasure. As much as he tried to fight it, Jack couldn't help but feel a slight tingling sensation begin to creep its way up his trembling body. His body and mind were caving in; he couldn't hold back any longer or fight against it anymore! Tears streamed down the Guardian's face as he completely succumbed to the Nightmare King.

"You belong to me, Frost… Your body, mind, and spirit are mine!" Pitch murmured into Jack's ear as he bit at it.

Jack could feel Pitch getting on his pleasure high. He thrust even harder and faster until the last second and gripped the spirit's hair roughly as he came inside him. The black cum burned inside Jack and seemed to writhe around in his body like the nightmares Pitch control causing him to feel sick to his stomach. As Pitch pulled his cock out of Jack, the nightmare sand holding him by his wrist dissolved along with Tooth's and the spirit fell weakly to the ground. Toothinana scrambled painfully on the ground to Jack, grabbing his frosted hoodie and wrapping it around his trembling body as she held him in her arms like a child, comforting him as he silently wept into her chest.

"You're a fucking bastard, Pitch!" Tooth spat furiously at the Nightmare King, "He's just a child! Look at what you've done to him!"

"I've broken his center," Pitch smiled sadistically as he wrapped his black robes around himself again, "Don't worry Jack… it won't be much longer now!" Pitch ran his spidery hand through Jack's hair softly as the sprit buried his face terrified into Tooth's feather chest. The Nightmare King smiled and took a step back to admire his work; the Tooth Fairy… bloody, cut up, feathers ripped out with black lashes all across her back and Jack… bruised, bloody, raped, terrified, and broken. After wallowing in his sadistic victory, Pitch bid the Fairy and Jack goodnight as he disappeared through the shadows in the room.

"O-Oh god Jack… I'm s-so sorry! Please forgive me, p-please," Tooth begged through tears that streamed down her face as she hugged the winter spirit tightly, "He should have done that to me! I could have handled it!"

"T-Tooth," Jack coughed out almost inaudibly, "M-my body h-hurts... it h-hurt s-so bad!"

"I know baby, I know! I'm gonna get you some help," Tooth promised as she cradled Jack's feeble body.

"I-It's gone…," Jack whimpered as tears formed in his eyes and shamefully rolled down his face, "He's done it… he's b-broken my c-center! It's g-gone!"

Awwww it's so sad! Poor Jack's center has been broken! What did you guys think of this chapter? Let me know and keep an eye out for the next chapter!