Raven's Choice

Dean's Descent

A little while after the big confrontation, Dean was sitting on a bench outside the Slayer school reflecting on the last week that Cas, him and Sam had been here. He was trying to think of a way to protect those he cared about the most. The only conclusion he had come to is he really, really missed Baby. The Impala was all alone, but at least Bobby would take care of her. He chuckled to himself shaking his head knowing that his love for his car was a little obsessive. Of course it’s the only possession he and Sam have that once belonged to their Father.

“You have been a very pensive young man this last week.” Giles said as he approached Dean. He stood there and waited, for what, Dean wasn’t quite sure. The guy had pretty much left Dean and Sam alone for the last week while Cas had his ‘quality’ time with the hot blonde. And for some reason this made Dean a little angry. After their talk in the den, he was sure there was going to be more. What more that was he still didn’t know.

“Yeah, well I’m kinda stuck in a country I’ve never been too, my car is…is…well I don’t want to think of what horrors have been happened to Baby. And I haven’t ganked any monsters in a freakin’ long time,” Dean raised his voice in anger, “All so Cas can get it on with some hot blonde, then you and you’re whatever it is…...” Dean looked full on at Giles letting all of his anger and frustration with his situation show.

“Dean,” Giles wanted to help this young man with his demons and he thought he knew how, but his approach had to be careful. He didn’t want to scare him, “My offer to help you still stands.” Here he paused and looked for the right words to say, “When I was touched by that demon, I was broken, scared, and angry. Physically it took a long time to heal, but mentally, emotionally even longer. My Wife was worried, she didn’t know what to do, so she searched for a solution and we finally found a way to deal with my problem.”

Dean wanted to ask, but for some reason he was afraid of the answer. “How….” He looked hard at the older man, and again Dean sensed a familiar darkness, a familiar pain, “How did she help you?”

Giles leaned down a little and looked into Deans very green eyes and said quietly, “I could show you.” Dean’s heart was pounding just a little too fast as he heard a dark promise in those words. Of what that was he didn’t know if he was ready to find out.

“So, is this like a gay thing? ‘Cause if that’s your thing that’s fine, but I’m not……” Giles looked at him with raised brows, almost knowing what he was going to say, “You know, gay.”

“No Dean, nothing so simple. Do you know what a Dominant Sadist is?”

“Whoa, um I don’t know where this is going……” He faltered because a part of him, a tiny voice, spoke up and said ‘hear him out’, but it scared him. He knew that once he stepped on that path, it would change him forever.

“Dean, I suspect deep down you have a masochistic side. In fact watching you with your brother this past week I am sure of it. You would let yourself be hurt for him, just so he doesn’t feel the pain. You take it, and you hold onto it almost like a badge of honor, but there is never any relief for you, for your pain.” Dean’s heart pounded just a little harder; he didn’t understand how this man, could see into those dark spots in his soul.

“What,” he said quietly, “What do you want from me, how can you help me?” Dean waited for an answer as he tried to understand his feelings and why he was drawn to the older man, and why was this offer so tempting.

“I often need an outlet for my dark….tendencies. My Wife is usually most accommodating, but once-in-a-while, I find someone I connect with, someone that wants or needs that release I can give them. It’s not often, but Dean, I find I am drawn to you, to your inner demons. If you want me to back off, if you’re not interested, I will understand.”

The thing was Dean didn’t want him to back off, he wanted to know more. “Tell me,” Dean said almost on a whisper, “Tell me I can be whole again. Tell me you can show me how to feel…..human again”. Giles moved in closer to the young man leaned down and whispered in his ear, “Meet me tonight, 10 o’clock. There is a room down the stairs from the den, if you want to know more, that is where I’ll be.”

Dean swallowed hard, anticipation and fear ran through him at the same time.


As the time ticked closer to 10 o’clock Dean’s anxiety rose. He didn’t know what Giles wanted, he didn’t even understand what he wanted, but he knew he was going to meet him. He dressed simply in jeans and a white t-shirt. He showered and shaved, for some reason he thought shaving was important. Nerves, like butterflies in his stomach, fluttered through him, but he made his way down the stairs and towards the den anyway. On the way he saw Sam in the library ‘God, the kid never stops’ he thought. Sensing someone watching him Sam looked up and saw a strange expression on Dean’s face and a sense of worry washed over him. He got up to go to his brother. Knotted brow and tilted head he asked “Dean, what is it? Where are you going?”

“Sam,” he stumbled on his words, looking back at his shaggy haired younger brother, “I’ve got something to do. Don’t worry if I come to bed late.” Dean couldn’t quite keep the anxiety out of his voice.

“Dean, is something going on?”

“Sammy, I just need to do….something and I need you not to ask any questions, okay?” Hearing the pain in his voice made Sam worry even more, but sometimes, and he learned this the hard way, he needed to let Dean work these things out for himself. He would eventually open up, hopefully.

Dean grabbed Sam’s shoulder and gave it a little shake, telling Sam with his touch what he was feeling even if it was hard to say with words.

“Okay Dean. Whatever you need to do, you know I’m here for you.”

“I know Sammy, I know.” He watched as Dean walked toward the den wondering what was going on, but wise enough not to push.

Dean didn’t tell Sam what he was about to do because he knew his brother would not agree and would try to stop him. He went down the stairs as instructed. He saw a large heavy door opened it and it easily swung inward on silent hinges. “Close the door.” Giles said. Dean did as asked and walked to the center of the room. He was actually surprised. He didn’t know what to expect from a kinky dungeon, but this was not it. Yes there was a bed with restraints, some bars hanging from the ceiling, a sort of tilted table and a large metal frame with restraints in the middle of the room. The sound proofed walls had various whips, riding crops, paddles and other instruments designed to administer pain when used by a deft hand. What he didn’t expect was the level of decoration and comfort. It wasn’t dark and dingy, but had a lot of light; the walls were covered in obviously expensive dusky gold wallpaper. Ornate tables, a leather couch and a couple of chairs were also scattered around the room. “Not what you expected?” Giles asked, standing there in khaki’s but no shirt. Dean noticed hard muscles and a defined upper body, he felt a little fear run through him at the thought of the force those muscles could exert, “No, I’m surprised. It’s kinky, but it looks, comfortable.” Dean said.

“Dean, you don’t have to do anything you don’t want to do. My offer always stands. Remember, in here you have all the control. You choose a safe word and you tell me your hard limits and I promise I will not violate either of those conditions.” For some reason, this relaxed Dean a little, but his heart was still beating hard, almost like it wanted to break out of his chest.

“Can I make one request? Can we have some classic rock playing? None of that namby pamby 80’s rock crap, but AC/DC, Led Zeppelin, Kansas, that kind of stuff?”

“Sure, just give me a moment.” Giles left Dean for a moment and he suddenly heard ‘Back in Black’ come over a hidden speaker. He didn’t hear his host come up behind him till he heard a whisper in his ear, almost predatorily. “Take off your shirt, if you’re staying.”

Dean’s breath hitched, he was afraid, but excited at the same time. He lifted the t-shirt over his head, exposing a hard muscled body riddled with scars and what Giles recognized as an anti-possession spell in the form of a tattoo. Dean looked at the older man, breathing hard with a mixture of anxiety and anticipation.

“What is your safe word?” Giles asked as he slowly walked around the young man.

Dean thought for a moment, “Kashmir.”

“What are your limits?” This back and forth negotiation was strange, yet kind of thrilling,

“No knives, no sex, and don’t scar the tattoo.”

“Sex is only reserved for my wife. Understand this Dean Winchester, once this starts, there is no going back, for tonight, you are mine until you give me your safe word, or I stop it myself, do you understand?”

Dean nodded his head that he understood fear climbed up into his throat. Giles moved very close to the young man, eyes so dark they were black, not demon black, but a darkness that Dean felt himself falling into, “I will hear you scream before this night is over.” Said Ripper, for at this moment he was no longer Rupert Giles.

Giles led Dean to the metal frame where his arms were lifted above his head and restraints were wrapped around his wrists. He was then told to spread his legs wide and Giles fastened his ankles as well. Dean tried the restraints out and knew they were very secure. He couldn’t get out of them, even if he wanted to. Around his waist was a sort of brace that was secured to the frame from both sides, “To help hold you up” Explained Ripper.

Ripper walked away for a moment from the young man, went to the wall and considered his options. He decided to go slow at first and grabbed the three tailed leather flogger. He walked around Dean, hitting him softly almost gently at first, building up Dean’s tension and anxiety. When the first real blow came it caught Dean off guard. The sting of it rang through his body, but he barely had time to process the first when he felt the second, and the third. By the time the fifth blow landed on him, Dean no longer resisted he let the pain in, let it wash over him in waves. This went on for several minutes while Ripper reveled in the welts rising on Dean’s body, which encouraged the older man to continue.

Ripper decided to change his instrument of choice, this time he went for a bullwhip that ended with a split leather tail. Dean was panting hard; he almost anticipated and welcomed the pain of whatever his torturer had in store. Ripper walked around the young man and flicked the whip towards the floor to create a cracking sound, trying to build up Dean’s anxiety and fear again. “Are you going to scream for me Dean?” He said as he cracked the whip around the young man’s waist.

Feeling the cruel pull of the whip around his body Dean didn’t want to give in and yet he did at the same time. His eyes were shut; mouth clamped in a challenge with himself not to scream out, not to give Ripper what he wanted. He felt each crack and flick of the wicked whip wrap around him. Ripper, no longer went easy on him as he tried to force Dean to give him what he wanted, the boy’s submission to the pain. After several minutes of this Dean couldn’t hold it back, he cried out and his cries were filled with the pain of the whip, the pain of losing his Father, the pain of Hell, from his years as a torturer and the pain of his guilt. He started to let it all out in his screams as each kiss of the cruel instrument wrapped around his tender flesh.

Ripper stopped, dripping with sweat from the exertion walked over to face Dean, lifted his head and asked, “Do you want me to stop?” Dean, eyes filled with silent tears, full of pain and also pleading looked at the older man, “No.” And hung his head, partly from the pain, and partly from the shame he was feeling, letting this man beat the crap out of his body, but it felt so…….good. Dean shut his eyes even harder thinking there must be something wrong with him.

Ripper laid the whip aside and went for a long thin flexible riding crop. He placed the middle part of it under Dean’s chin and lifted his head, “There is no shame in what you’re feeling, let yourself revel in the pain , let me hear your screams” he slowly lowered the instrument walked to the side of the frame and landed a powerful blow on Deans already tender back. The force of the blow ripped a scream from the boy, while Ripper continued to expertly land blows all over Dean’s torso, without breaking any skin and without disturbing the tattoo. This went on for almost an hour, the different instruments of torture changed from time to time which gave the young man different pain sensations.

Dean finally let it in, giving in to it, his head fell back and he began to enter a different state.

Ripper saw that Dean had entered that delicate, yet dangerous state of subspace. A state where pain is no longer felt, where each blow can felt like a kiss or a caress. He decided to end their session. In this state Dean would not use his safe word, he’d let the tortures continue till he was ripped apart and Ripper knew just what that felt like. He took off the stabilizing belt, then slowly undid each of the restraints, and lifted the young man up and laid him on the bed all the while Dean protested saying he could take more, he wanted more. Ripper went to the small bathroom to the side to get Willow’s special antiseptic and soothing lotions. Dean continued his pleading, while Giles gently applied the antiseptic and came down off his own high.

Dean started crying at the gentle touch, hard wracking sobs; he curled up into himself and let out years of buried emotional pain. Giles gently took the young man in his arms and rocked him and encouraged him to let it all out.

Finally, when he was spent, Dean laid back down and lets Giles smooth the cooling lotion all over his chest and back. “You can stay here for the night if you want.” Giles told him, “If you need anything, there is a phone right there and one of the night maids will take care of it.” Giles stayed awhile and watched the young man and wondered what more there was, what other emotions he was hiding. When he sensed Dean had fallen asleep he slipped out of the room and went to his ever patient wife to give her a good, hard fuck.

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