Chapter Text
Castiel Novak, the personal assistant to the director of Sales and Marketing, had one job: to keep Dean Winchester happy. He was good at his job, quite exceptional at it actually. He had been at the company for six months and was handpicked by Mr. Winchester himself.
Castiel was on call at all hours for his boss, but he had no complaints. If Dean Winchester needed something in the middle of the night, Castiel was the first person he called. He bent over backward for the man but was rewarded greatly for his loyalty. Castiel wasn’t in need of anything since his boss always padded his checks with extra money any time he went above and beyond the call of duty.
Friday started off as any other day of the work week. Castiel woke at five that morning and went for his morning run. After that, he hit the shower then stepped out, dried off, and dressed in a deep blue button-down that accentuated his eyes, a black tie, and black slacks. He slipped on his socks and shoes then walked over to the mirror. He ran a hand through his perpetual sex hair that never stayed down. Deciding he looked presentable, he grabbed his cell phone and keys and headed out the door.
Thirty minutes later, he arrived at work, parked his car in his assigned space and headed inside. Castiel said good morning to the front receptionist and then went up to the tenth floor. He headed into the executive lounge that he had access to so he could make Mr. Winchester’s coffee. He grabbed one of the disposable cups and poured the steaming liquid inside, added two scoops of cream and one sugar. Once he fastened on a lid, he walked out of the lounge and down the hallway to his boss’ office. Castiel knocked twice and opened the door. Mr. Winchester was on his Bluetooth with clients already. He looked up from his desk, gave Castiel a lazy smile and motioned for Castiel to sit down. Castiel placed Mr. Winchester’s coffee on his desk and sat down in the seat in front of it. He crossed his legs and patiently waited until Dean was off the phone.
“Yes, Mr. Hamilton. I’ll have my assistant send an email to you with all the details. We look forward to your business. Thank you for considering us. You have a good day.” Mr. Winchester hung up the phone and grabbed his coffee. He took a long sip and leaned back. A soft moan escaped and he closed his eyes. “Just the way I like it. You’re so good to me, Castiel.” Mr. Winchester opened his eyes and looked over at Castiel as he placed the coffee back on the desk. “So I’m sure you followed that call. I’ve written down the details of the email to send. I have a presentation today if you could set that up for me. Also, I have a lunch meeting with a new client. I will need the boardroom set up and lunch catered.”
Castiel nodded, “I set up boardroom one yesterday in advance for your presentation. Everything you need is ready to go. I’ll get boardroom two ready to go and I’ll call Buca di Beppo’s for lunch.”
Mr. Winchester lifted the coffee and took another sip. “I had a craving for Italian food. Good call, Castiel. You know me so well.”
The praise made Castiel blush and a huge smile crossed his face. “That is my job, to keep you happy.”
Dean licked his lips and smiled. “Those are dangerous words, Castiel.”
Castiel felt his pulse quicken. If anyone else had said that it wouldn’t have had such an effect on him, but truthfully the air of dominance that surrounded Mr. Winchester had a pull on him. His boss was gorgeous from the freckles that spattered across his nose and cheeks, his deep green eyes, to his pink plush lips. More than once Castiel had fantasized about running his hands through his boss’ short brown hair that was always styled perfectly.
Their eyes locked in a long gaze and finally, Castiel found his voice again. “Will there be anything else, Mr. Winchester?”
His boss didn’t answer just shook his head no and smiled again. Castiel stood up and made his way to the door.
The call came at eight that night. It didn’t surprise Castiel in the least.
“Mr. Winchester?”
“Castiel, I’m sorry to call you so late. I left the office in a rush and left some reports on my desk that need to be finished. Would you be able to pick those up for me and bring them to my house?”
“Of course, I’ll be there in about an hour,” Castiel replied. After their goodbyes, he hung up and looked at himself in the mirror. He was wearing a black Henley and faded blue jeans. Castiel decided he looked fine and slipped his tennis shoes on.
***
An hour later on the dot, Castiel stopped out in front of the gates of the Winchester estate. He punched in the gate code and waited for it to open. As soon as he was able, he drove up the driveway and parked in front of the mansion. Castiel was always in awe of the place each time he visited. As he stepped out of his car, a loud clap of thunder roared in the distance, the sky light up with streaks of lightening. Castiel walked up the steps and rang the doorbell. After about five minutes, the door was opened by a maid, Rosalyn, and he was ushered inside.
When the door closed, Castiel looked in front of him and watched his boss descend the stairs. Mr. Winchester was still wearing the clothes from earlier that day. However his hunter green button down was un-tucked, the tie was gone, the top four buttons were undone, his belt was gone, his feet were bare, and his hair looked like someone ran their fingers through it. The image made Castiel’s mouth go dry and he had to force himself to speak.
“I have the reports you needed, Mr. Winchester,” he said and willed his voice not to waver.
The other man gave Castiel a slow smile. “Call me Dean. Have you eaten, Cas? May I call you Cas?”
Castiel nodded, “Yes, of course, Mr.. err, Dean. And yes I’ve eaten already.”
“Good. Good. Well, would you like a drink? There is a shit storm coming and I would rather you not be out in it on account of me.”
Castiel nodded and Dean placed a hand on the small of Castiel’s back and showed him to the lounge room.
***
Dean and Castiel were sitting side by side on a very plush black leather couch. Dean had just refilled their glasses of whiskey. For the past hour, while rain poured outside they talked about their lives. Dean spoke of his family history and owning half the company, but wanting to remain only the director of the department. His brother Sam controlled the other half. He asked Castiel about his family and what his ambitions are in life. Castiel found it easy to talk to Dean. He told Dean that his dream was to be a writer one day. Maybe travel the world and find inspiration in different places.
Castiel looked around at the room. Everything was done in black and whites. There was a large flat-screen TV on one wall and large collections of DVDs under it. To the right of him was a long white chaise lounge. To the left were floor to ceiling bookshelves full of books. There was meticulous order to everything in the room.
Feeling a little bold after his second drink, Castiel relaxed and asked the question that had been burning in his mind. “So if I may ask, is there a Mrs. Winchester?”
Dean laughed and leaned back against the couch. He was turned facing Cas. His right leg pulled up on the couch and would brush against Cas when Dean would move. “No, there isn’t a Mister Winchester.”
Castiel reached and rubbed the back of his neck, a blush creeping across his face. “Oh… oh. Well…”
Dean threw his head back in a full body laugh.
Castiel tilted his head to the left and smiled. “What’s so funny?”
“Nothing. Nothing at all, Cas. But to answer your other question I know that you’re thinking, I don’t have a boyfriend either.”
Apparently, Dean could read Castiel like an open book. Because that was a question he wanted to ask but didn’t feel it was appropriate. “Why not,” Castiel asked.
Dean sat up a straighter. “I’ll be honest there is someone I’ve had my eye for quite some time now.” He smiled and ran a hand through his hair then moved a little closer. “I’ve never made a move on this person because he is an employee of mine. I never cross that line. But with him, I feel I can’t hold back.”
“Who,” Castiel asked before he could stop himself.
Dean looked Castiel straight in the eyes and without hesitation said, “You, Cas.” He reached out and placed a hand on Castiel’s left cheek. “Since you walked into my office the first day I’ve felt drawn to you. I tried to ignore it. I never wanted to put you in a position where you felt you had to do anything. Then I found reasons to call you so I could be around you more. I’ll be honest I do want to see where this could go. But I want to make it perfectly clear that if we cross that line or not, it will never affect your job.”
Castiel’s heart jumped and his pulse started racing. He couldn’t find words to speak so instead he leaned into Dean’s touch and nodded. Castiel felt like he had to be dreaming. This was too good to be true. His brain screamed to stop and think it over, but he trusted Dean.
“Because my desires are unconventional, I have to know, is this something you want?”
Again, Castiel just nodded. Dean smiled then said, “Use your words, Castiel.”
“Yes.” It was just above a whisper, but Dean heard it and his breathing hitched. He leaned forward and brushed their lips together.
Castiel let out a moan his head swam with desire. His jeans were suddenly too tight. He was a twenty-five-year-old man and he popped a boner from just one kiss. Dean’s hands found their way to Castiel’s hair and he deepened the kiss. Castiel’s eyes shut and he lost himself to the feeling of Dean’s tongue running over his. Dean broke the kiss, stood up and reached for Castiel’s hand. When he felt Castiel’s hand in his he smiled and led Castiel into the foyer. At the bottom of the stairs, Dean stopped and looked into the other man’s blue eyes almost like asking again if Castiel was sure.
“Show me, Dean,” Castiel said. Dean smiled and continued up the stairs they turned left and went up another set of stairs. Castiel’s hand was still in Dean’s and he followed Dean down to the fourth door on the right. Dean opened the door into the master bedroom. The color scheme for the room was much the same as the lounge with blacks and whites. The difference was there were splashes of red. In the middle of the room was a king size four-poster bed made of painted black wood. The bedspread was a vibrant red. There were back night stands on each side with lamps that had red shades.
Dean pulled Castiel in the room and kicked the door closed with his foot. He turned around and his hands immediately flew to the hem of Castiel’s shirt. Dean yanked it up and over Castiel’s head and threw it. He stood back and ran his eyes over Castiel’s bare chest. He groaned, “So beautiful for me, Cas.” Dean moved into Castiel’s space and picked him up, crashing their lips together. He bit at Castiel’s bottom lips and growled when he heard Castiel moan in response. Dean grabbed Castiel’s thighs, turned them around and walked to the bed. When Dean’s knees hit the edge of the bed he laid Castiel down. His ran his hands over Castiel’s chest and worked their way down to unbutton Castiel’s jeans. Dean locked his green eyes on Castiel’s blues. He unzipped the jeans and pulled them off along with Castiel’s boxers.
Dean threw them off to the side, stepped back, and ripped his shirt off the rest of the way, buttons flying off in every direction. He unbuttoned his pants and pulled them off with his boxers never breaking his eye contact with Castiel. Castiel’s breathing hitched at the sight. Dean backed up and switched on the lamp on the left table. He flipped off the main light and the room was washed in a dim red. Dean opened a drawer and pulled out a condom and lube and a blindfold. He set it on the right side of Castiel. The he crawled up the bed and straddled Castiel’s hips. Dean leaned forward and captured Castiel’s lips with his own. His tongue ran across Castiel’s lips, “Open for me,” he breathed out. Castiel didn’t have to be told twice. He opened for Dean and his tongue ran slowly across Dean’s making the man above him moan.
Dean pulled back a little and Castiel tried to chase his lips which made him chuckle. “Eager are we,” Dean asked and kissed down Castiel’s jaw. He moved up to Castiel’s left ear and spoke in a whisper. “Submit to me, Castiel, and I’ll show you a world of pleasure you never even knew existed. I’ll awaken your body to feel things you’ll never forget.” He kissed his way down Castiel’s neck, across his clavicle, biting along the way. He ran his tongue up the right side of Castiel’s neck and spoke in his ear, “But tonight I’m going to worship your body.”
Castiel writhed underneath Dean and moaned. He clawed at Dean’s arms. “Do you want that Cas?” Castiel tried to form words and finally his brain kicked in. “Yes. Yes. Please, Dean. I want you.”
“Patience, my pet,” Dean growled and reached for a blindfold. He looked at Castiel, “You have to trust that I would never do anything to hurt you, Cas. Do you trust me?”
“Yes,” was the only response Castiel could manage.
Dean placed the blindfold over Castiel’s eyes and then reached for the lube. He moved to the back and sat on the bed, pushed Castiel’s legs up as he coated his fingers with lube. Dean circled the pad of his finger against Castiel’s ass coating it well and then pushed a finger in past the tight ring of muscle.
“Oh fuck, Dean.” Castiel panted. Dean worked his finger in and out. When he felt Castiel open more, he added a second finger. Dean leaned forward while moving his fingers inside Castiel and hit his prostate. At the same time, he bit the inside of Castiel’s thigh.
“Fuck. Dean, please, more.” Castiel screamed out.
Dean moaned and hit Castiel’s prostate again. “You’re so good for me. I love hearing you beg.” Dean quickly added a third finger and twisted them around. Castiel bucked his hips.
“Dean… oh… fuck… me please,” Castiel said through moans. Dean removed his fingers and chuckled when Castiel whimpered. He sat up on his heels and felt for the lube and condom, ripped it open with his teeth. Dean rolled it over his cock and poured lube in his hand then coated his length with it. He repositioned himself between Castiel’s legs, putting his right arm on the side of Castiel and held his weight on it. He grabbed his cock, lined up, and pushed inside past the tight muscle slowly. He stopped allowing Castiel’s body to adjust to his size. When Castiel nodded, Dean pushed deeper inside until he bottomed out.
“Uh… so tight for me, Cas.”
Dean listened to Castiel’s breathing for any sign to stop.
“More, Dean, please I need more.”
“Shhh, Cas. No talking, no thinking, just feel.”
With that, Dean gripped Cas’ hips and pulled back and thrust in harder. Cas’ back arched, he had never felt a sensation quite like what he was feeling at that moment. Dean rolled his hips to change his angle and the next thrust ran over Castiel’s prostate. Dean watched Castiel’s body shake in pleasure and come apart under him.
“That’s right, my pet, just feel every thrust inside your beautiful tight body pushing you over the edge.”
Dean’s thrusts became hard and more erratic. The moans and whimpers coming from Castiel let Dean know he was close to the edge. He didn’t hold back any longer. Every thrust in hit Castiel’s sweet spot.
“Come for me, Castiel,” Dean said in a commanding voice. Those words are what sent Castiel over the edge. His back came off the bed and he dug his nails into Dean’s back. Watching Castiel come drove Dean over the edge himself. Two more thrusts and he came with Castiel’s name on his lips. Dean collapsed on top of Castiel. He reached up and pulled the blindfold off. Dean crushed their lips together and kissed Castiel deep.
Dean broke the kiss, “So good for me, Cas. You were so good. Watching you come drove me crazy,” he panted. Then he pulled himself out and rolled off the side of the bed. He removed the condom, tied it off and tossed it in the trash. Dean walked into the bathroom that was connected to the master bedroom and grabbed a washcloth. He wet it and went back to Castiel. Dean ran his finger in the come on Castiel’s stomach and brought it up to his lips and into his mouth. Dean smiled at Castiel.
“Mmm, you taste good,” Dean said as he ran the washcloth over Castiel’s body. Once he was clean, Dean crawled back up on the bed. He motioned for Castiel to lay by him. Castiel curled up against Dean’s side as Dean pulled the covers over them. He leaned over, turned off the light, and settled in next to Castiel.
“Dean?”
“Yeah, Cas?”
“You said your desires are unconventional. What did you mean by that,” Castiel asked.
Dean laughed and ran his hand through Castiel’s hair. “Maybe I’ll show you next time. If you’re ready that is. Let’s sleep.”
“Good night Dean.”
“Good night Cas.”