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A Long Night

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The Novaks are known for their ruthlessness and their sadistic personalities. But unbeknowst to most people, one Novak was kinder than the others. Yes, he’s strict, but he still knew umanity. His name is Castiel.
Living in a mansion by the cliff near the sea, Castiel owns alot of things, including SLAVES. His favorite by far, was one of Dean Winchester. Born to the world of slavery, he was raised to offer himself to his Master. When Castiel had bought him, Dean was a broken man. Feeling his gut wrenched, Castiel finaly nursed Dean into health and taught him what’s it’s like to be human. Castiel only asks for one thing, which is for Dean to not dissobey his orders. Imagine his wrath when he found out that Dean had done tha=e exact thing.
~
Dean was layed down on the bed, naked. His hands are tightly bound to the head of the bed. His legs spread apart and tied to the foot of the bed. Cas stood in the corner and marveled how beautiful Dean looked. As much as Cas wanted to screw Dean till he can’t walk for a week, he needed to teach his slave a lesson. Dean had touched himself and came without permission, and Cas don’t want that to happen again.
He moved to the tray at the side of the King sized bed. Above lay atleast a dozen different dildos completed with collars, plugs, vibrators, cock rings, cock cages, nipple clamps, blindfolds, hand cuffs, and even a whip. Cas planned to use most of this on Dean tonight.
“Do you know why you’re being punished, Dean?”
“Yes, sir. I touched myself and came without your permission.”
Cas knelt next to Dean and rubbed his inner thigh. Dean drew in a sharp breath.
“Tonight, you will receive your punishment without a complaint. If it gets too much, use the safeword. You know which right?”, asked Cas.
Dean nodded. “Green for okay, yeloow for wait, red for stop.”
“Your punishment won’t last only tonight. We’re going to do the same routine I’ll be giving you tonight for a whole week. That should teach you not to dissobey me. Do you understand, Dean?”
Dean gulped, but he nodded anyways.
Cas smiled and he reached cock ring. Knowing to take precautions, Cas decided to use three. He went back to the bed and placed the ring on Dean’s cock. Dean whimpered, but didn’t complain. Cas then meoved to take the whip.
“You have been a very bad boy, Dean. To start your punishment, you will receive 15 whips to your rim. We are going to add 2 everyday. Is that okay for you, Dean?”
Dean shivered. The whipping is going to hurt for real, but knowing Cas, Dean knew that he will make up for it later. He nodded. “It’s fine, sir.”
“I want you to count, Dean. Loud and clear.” And with that, the whip came down to hit Dean’s rim. Dean muffled a scream.
“One.” Boy did it hurt.
The whip came down again.
“Two.”
By the time Cas has reached ten, Dean had tears in his eyes. Cas moved to wipe them.
“What’s your color, Dean?”
“Green, sir,” answered Dean.
Cas nodded and proceeded to continue his punishment. Eleven strikes and Dean finally groaned out. Twelve was followed with a whimper. Thirteen with a shout. Fourteen with pleads, and finally, fifteen with relieve.
Dean’s rim was red and hot after he whipping. Cas moved his hand to touch that part which made Dean whimper. He didn’t know if he could take it tomorrow. As Cas massaged Dean’s rim, the pain subsided and was replaced with comfort.
“Good boy, Dean. You did the first part really well.”
Cas moved to the tray to take on the smallest dilso. It was 5 inches and it’s perfect to loosen Dean up.
“There are 12 dildos that you will have to take tonight, Dean. You are not allowed to come before I said so. Is that clear?”
“Yes, sir.”
“Would you like to be prepped before, Dean?”
This is what Dean liked about Cas. Even though he was strict and his punishments were a pain in the ass (literally), he would let Dean make his choices.
“Yes sir.”
“How long do you need?”
Dean, wanting to make up to Cas answered, “15 minutes, sir.”
Cas raised his eyebrows. They had an agreement. 5 minutes of prep will leave Dean on the edge but not enough to come. 10 minutes if they were doing kinks. But 15 minutes mean that Dean was loose enough that he allowed Cas to stimulate his prostate to the verge of tears. They rarely do it, amd Cas was proud of Dean.
“15 minutes it is, then. Remember to give me your color, alright, Dean?”
“Yes, sir.”
Cas opened the bottle of lube and covered his fingers with it. Sitting between Dean’s spread legs, Cas pressed a finger on Dean’s opening. A shiver ran down Dean’s spine. Moving his fingers in circles, Cas slowly pushed inside trough the tight muscle. The finger went in smoothly, and Dean felt so good.
Cas started to move his fingers in and out of Dean. Dean was panting hard on the bed. When Cas felt that Dean was loose enough, he pushed in a second finger. It went it with some resistance, and Cas stopped to let Dean get used to the feel before continuing.
“Color, Dean.”
“Green, sir,” answered Dean hurriedly.
Cas moved the fingers in and out. Dean was moaning now. The air was filled with the sound of skin moving against skin and Cas’s name spoken out of Dean’s words.
Cas started to scissor Dean, and Dean can’t help but buckle his hip and contracts his hole. Cas chuckled.
“Relax, Dean.”
Dean could only nod, having the ability to speak torn away with Cas’s finger. Slowly, the walls around Cas’s finger lossen up, and Cas continued with his ministrations.
Searching for the bundle of nerve that made Dean crazy, Cas was rewarded when Dean screamed out and his hips arched against the bed. Dean was so hot that Cas felt his erection hardening.
Cas then hit the area again, making Dean plead to let him come. Cas wasn’t having any of that though, as he nailed Dean’s prostate over and over again. When 14 minutes have passed, Cas pressed Dean’s prostate and pushed it. Dean screamed and begged for Castiel to let him cum. Cas held his fingers there, occasionaly pushing more till the 15 minutes are up. Dean whimpered at the loss of Cas’s finger, but he stayed silent and waited for the next stage of his punishment.
Taking the small dildo, Cas lubed it and prodded it against Dean’s hole. Pushing it inside, Dean arched his back as the dildo hit his over-stimulated prostate. When it was fully seated inside of Dean, Cas took the remote and set it to the lowest setting. A sound came from Dean’s mouth, between a whimper of pain and pleasure. Normally, it would be embarassing for Dean, but right now, he couldn’t care less.
Cas moved to touch Dean’s cock. Dean shuddered. Cas spoke in a husky voice, “Who does this belong to, Dean?”
“Yours, Cas. Always yours.”
“Yes, Dean. Your body mine. And what happens if you touch it without my permission?”
“I got punished, sir.”
“Good. I want you to remember that, Dean. From now on, every time you are going to be penetrated, you will say ‘My body belongs to my Master, Castiel.’ Do you understand?”
“Yes, Master.”
“Now say it.”
“My body belongs to my Master, Castiel.”
Cas turned the dildo to a higher level and Dean shouted. Moving the dildo in and out of Dean, Cas spoke, “Louder, Dean.”
“My body belongs to my Master, Castiel.”
Without warning, Cas turned the dildo to a higher setting and Dean screamed so loud while arching his back to show his perfect body.
“Louder!”
“MY BODY BELONGS TO MY MASTER, CASTIEL!” Dean practically screamed.
Knowing that Dean had learned his lesson, Castiel turned the dildo off after a few seconds. Dean was a moaning mess on the bed right now.
Taking a bottle of water, Cas opened it and let Dean drank a few gulps. Putting the water back to the bedside table, Cas removed the dildo from Dean’s hole. A cold rush of air hit Dean and he whimpered at the loss.
Cas took another dildo. They repeated the same process again. Soon, Dean has taken 11 dildos and his hole is a puckered mess. Dean was crying in bed and begging Castiel to let him come. Cas approached and rubbed his head gently. Dean tensed at first, but seeing Cas’s intention he relaxed.
“Shh... It’s okay, Dean. Do you want to stop?”
Dean sniffled. He shook his head.
“No, just, plese let me cum when we’re done.”
“Of course, Dean.”
Castiel took the last dildo and examined it. 12 inches with tiny bumps that guarantees prostate stimulation. Dean was oversentitive for a week when they fist used this. Cas was doubtful that Dean would be able to handle it. Cas approached Dean and said, “The last one is really hard, Dean. Are you sure you don’t want to stop?”
A moment of silence passed before Dean spoke, “No, sir. I want to make you proud. You’ve prepped me well. I can take it.”
Cas felt pride rise in him. He kissed Dean’s forehead and said, “You make me so proud, Dean. I love you, you know?”
“I love you too, Cas.”
Cas kissed Dean’s foehead before moving to lube up dildo. Pressing it against Dean’s entrance, the dildo went in smoothly without too much resistance. Turning the vibrations to the middle setting, Cas pushed it in and out of Dean. Dean moaned and writhed against his restraints. It felt so painful and good at the same time.
“You’re doing so good, Dean. Such a good boy,” Cas praised, knowing that Dean loved it really much.
“Please, sir. Please let me come! I’ve been such a good boy, Master, please let me come!” Dean shouted.
“Shh... It’s okay. Since you’ve been such a good boy and didn’t ask to stop, I will let you come, but only tonight, alright, Dean?”
“Yes, sir. Thank you, Master. Thank you!”
Castiel removed the cock ring from Dean and pumped the dildo faster. Dean came with a shout a second later. Thick white spurts of semen painted Dean’s stomach. The orgasm was so intense that Dean lost concioussness for a while. Cas kept moving the cock, milking Dean through his most intense orgasm.
“Thank you, Master! Thank you.”
“Shh... It’s okay Dean. You did very well. You were very good.”
After a few minutes, Dean finally calmed down. His prostate was still overstimulated, but it felt good to finally please Cas.
“There is still one last part of your punishment, Dean. Do you think you can handle it?”
Dean look at Cas with tired but lustful eyes. He was very exhausted, but he still wanted more.
“Okay, Master. I can do it.”
Cas took a cup from the floor and placed it infront of him.
“You stilll have some come left. Since tonight is all about you, I want to make you come till you’re dry into this cup. I well then proceed to put your seed inside of you through the night. How’s that sound, Dean?”
Dean gulped. He’s still horny after his treatment from he night, and beeing filled felt really good. Dean nodded. “Okay, Cas. Fill me up with my own seed.”
Cas smiled and proceeded to give Dean a hand job. Moving his hand up and down Dean’s shaft, Dean moaned incoherent words. When Cas pressed his thumb against the slit, Dean jerked, and he came into the cup. Cas knew there was still some more in Dean, so he stuck two fingers inside Dean and gave Dean one of the most intense prostate massage Dean has ever endured. All too soon, Dean was dry, and the cup was filled a little more than halfway up.
Taking a syringe (without the needle), Cas filled it with Dean’s come and pressed it against Dean’s hole. Going as deep as he can, Cas pressed the syringe, and slowly, Dean was filled with his own seed. It felt weird to Dean, but it was also quite plesurable.
Taking a butt plug from the tray of toys (apparently they didn’t use all), Cas pushed it inside of Dean without any lube to ensure it stays in. Cas then removed Dean’s restraints. Cas helped Dean to sit up and gave his shoulders a massage.
“You were amazing, Dean. I’m so proud of you.”
Dean could only chuckle, feeling to exhausted to talk.
“Come on, let’s get you to bed.”
Slowly, Cas helped Dean get on his feet. The plug brushed againsts Dean’s prostate, but it felt great. Moving to the bathroom on the training room, Cas quickly showered Dean in warm water before putting Dean in pink laced panties that showed of his ass. Cas rubbed it and gave it a squeeze, earning a groan from Dean.
“Tomorrow morning, we’re going to do some training. Trust me, Dean, by the time this week has finished, your hole will be spent and you won’t be able to walk for a month.”
Dean could only groan out in response. Cas then put on Dean’s collar back and his uniform nipple clamps. Cas marveled at Dean’s beauty. Unlocking the door of the training room, Cas called in his other slaves and ordered them to prep the room for tomorrow night. Leading Dean into the master room, Cas layed Dean down on the bed and took the bottle on the drawer beside him.
It was filled with Cas’s cum, as a reminder of who Dean belongs too. Dean, knowing what was happening next opened his panties and layed on his stomach. Cas pouring some cum onto his hand smoothed it out on Dean’s back and perfect round ass. Massaging his back, Dean purred at the feeling of being taken care of. When most of the cum has dried, Cas ordered Dean to lie down on his back. Dean did as he was told.
Cas then stripped and took a quick shower. When he came back, Dean was barely awake. Moving to cuddle him, Cas kissed Dean’s forehead. Looking at the time, it happened to be 12 a.m. Dean had been in the training room for 3 hours.
“I’m so proud of you, Dean. Tomorrow, we’re going to continue your training. But for now, go to sleep, okay?”
“Mmmhm...” replied Dean.
They both slept for 9 hours in the warmth of each other’s embrace. To other people, it might seem weird, but Dean and Cas don’t care. They love each other, and that was what mattered the most.
~