Chapter Text
Charlie came and sat down on the couch across from Dean – sitting sideways to stretch her legs out across the cushions – bringing with her two bowls containing heaping helpings of vanilla ice cream.
"Aren't you literally lactose intolerant?" Dean smirked as the redheaded girl shoved a spoonful into her mouth.
"Aren't you literally a little bitch?" Charlie retorted, scrunching up her nose at him.
Dean chuckled and took a bite of his own ice cream. "God, ice cream is so good."
Charlie nodded. "I hope whoever invented it got their dick sucked clean off."
Dean made a face at that. "Kind of sexist of you to assume it wasn't a woman," he joked.
Charlie rolled her eyes at him. "Oh, so women can't have dicks all of a sudden? Grow up, Winchester."
Dean groaned. "I didn't mean it like that!"
Charlie shook her head, a faux-offended expression on her face. "No, no, you were being transphobic."
The man rolled his eyes. "How am I going to be transphobic when my best friend is trans?"
The girl shrugged. "It's possible, but I know you're just jealous of all my t-girl swag."
They both laughed for a second before a beat of silence.
"Speaking of dicks, though…" Charlie started, setting her bowl aside and turned to face Dean. "How was your appointment?"
Dean frowned, feigning innocence. "Appointment?”
Charlie hit him with a throw pillow for that, and he supposed he deserved it. "With Castiel, numb nuts!"
Dean rolled his eyes and shrugged. "We're going out to dinner together tomorrow night, so… I think it went well." He felt a blush rise in his cheeks, and he kept his eyes fixed on the frozen treat in front of him.
Charlie squealed and stuck out her foot to kick his leg. "That's amazing! You liked him?" She suddenly got very serious. "He didn't hurt you, did he? Because, Dean, if he did, I swear–"
Dean rolled his eyes and looked up at her. "Charlie, you work for the guy!"
"Doesn't mean I can't kill him for hurting my best friend!”
Dean shook his head and sighed, shaking his head. "He very much did not hurt me." He chanced a look at her again before stabbing at the ice cream with his spoon. "He was actually amazing. I've never had anyone treat me like that before. He was so…" he paused, searching for the word, " kind ."
Charlie smiled at that. "He fucking better have been!"
Dean groaned, and looked up only when he felt Charlie softly kick him again.
"For real, though, Winchester, I'm really glad. I've worked for Castiel for about a year now, and he's always seemed really genuine. We've never actually hung out or anything, but I definitely consider him a friend at this point. He's super chill."
Dean frowned. "How come you never told me about him?"
Charlie rolled her eyes. "Didn't exactly know you were into getting bossed around in the sack, did I? No! Because I'm fucking chopped liver to you apparently!" She threw her hands up and sighed dramatically.
Dean held his hands up defensively. "Okay, forget I asked!"
"Oh no, you don't get off that easy, mister." She paused for a moment before smirking at him. "That's what he said!"
Dean laughed and threw a throw pillow at her head, which she dodged expertly. "Shut the fuck up, demon child!"
She winked at him. "You love me."
"I don't know. I'm transphobic, remember?" He winked back at her.
Charlie's mouth fell open on feigned shock and she crossed her arms over her chest.
Dean chuckled and changed the subject. "How did you even start working for Cas, anyway?" Dean asked, taking a bite.
Charlie retrieved her own bowl and also took a bite as she shrugged. "He hired me off of Craigslist to build him a website."
Dean raised an eyebrow. "Craigslist?"
The redhead shrugged again. "What, am I supposed to put an add in the newspaper for my hacking abilities??" She rolled her ryes. "Listen, he also asked if I could do background checks fast and offered to pay me under the table, so I didn't ask any questions. It was only later that I discovered what he did for a living."
Dean nodded. He guessed that was fair. If someone is asking you to do a job like that and offering to pay you illegally, you don't really ask any more questions than absolutely necessary. "Does he still pay you under the table?" The fact that Cas had offered that in the first place kind of weirded him out. He wasn't sure he wanted to get involved with someone like that. Who was to say what else he was involved in?
She rolled her eyes again. "Dean, I'm a hacker. Why are you so concerned about legality all of a sudden?" She took another bite of ice cream. "Plus, he's not part of the mob or anything, if that's what you're thinking." Charlie laughed out loud at the thought. "Nah, as soon as he got the business on its feet, he put me on the paperwork. And now I have to pay stupid taxes on everything he gives me." She pouted at the last part. "All because Mr. Man was too afraid he'd get audited or some shit."
"That's a valid concern, Charlie."
Charlie stopped mid-bite of ice cream. "Where is the rebellious, shop-lifting, stealing-Sam-his-Christmas-presents, bad boy outlaw that I fell in love with, Dean?"
This time he rolled his eyes. "I was never an outlaw." It was true, but he had luckily never gotten on the wrong side of the law. He'd fled from the cops a few times for stealing, but never had gotten caught.
She gave him another soft kick.."Not with that attitude." There was a beat of silence before she nudged him once more with her foot. "You're going out with him, though?"
Dean nodded, looking down at his lap. "Yeah. If he doesn't change his mind." Castiel changing his mind was always a possiblity. He hoped not a very likely one, but a possibility nonetheless. Part of him had also kind of wondered if he had still felt everything he said when he went home that night. Maybe the man had had a moment of clarity and realized he really needed to charge Dean for his services. Maybe--
Charlie groaned and picked the throw pillow back up, smacking him with it again, pulling him from his thoughts. "Hey, idiot, can you stop being mean to my friend Dean, please? I'm trying to have a good time over here."
Dean chuckled and threw the pillow back at her. "How's Dorothy?"
Charlie shrugged. "Didn't work out."
Dean frowned. "Why not?"
"Her dad passed away, and she said she's not in the right headspace for a relationship right now."
"Understandable."
"Yeah. True. Still sucks, but I'm respecting her wishes. So now I'm single and ready to mingle, baby!"
Dean shook his head. "Are you okay, though?"
Charlie thought on that for a second. "Yeah. I don't think we really had much going for us to begin with." She paused and tossed her head back and covered her face with her hands. "Except the sex. God, that was good sex."
Dean chuckled. "I'm sure you'll find some other girl to distract you soon enough."
Charlie eyeballed her friend for a moment. "I hate you. That's literally exactly what Castiel said."
Dean smirked and shrugged. "Great minds, and all that, I guess."
—
Dean found himself pulling into Castiel's driveway at 6pm sharp. The older man had offered to drive, but Dean didn't want to miss an opportunity to show off Baby, his 1967 Chevy Impala.
The body of his Baby was black with silver detailing. It had originally been his father's, but when the man had died of a alcoholism induced heart attack, Dean had taken the car as his and loved it like it was his child.
As he put Baby in park and turned her key till the purr of the motor silenced, all he could hear was his own heartbeat.
Getting out of the car, he took a look around. Before him was a two-story house with white siding and black shutters on its windows. There was a lush, circular flower garden on the right side of the front lawn with a ring of river rocks around it as a border. He could see multiple bees and butterflies landing on the different flowers, probably drinking from them.
"Aren't they beautiful?" called a Castiel that had suddenly appeared at his front door, leaning against the frame. He chuckled at the shocked look on Dean's face and shrugged. "I heard you pull up."
Dean's mouth went dry, but he still darted his tongue out to try and moisten his lips. Should he have brought flowers or something? He wasn't even sure what kind of flowers he would have brought.
Castiel casually pushed off the doorframe and turned to lock the door before stepping off the porch to come meet Dean. As he crossed the yard, Dean noticed he was once again wearing a nice white dress shirt – with the sleeves rolled up to his elbows, slacks, and dress shoes. His hands were in the pockets of his pants in a way that should not be so masculine and sexy.
When he reached Dean, he reached out and touched Dean's shoulder before leaning in and kissing him on the cheek. "Hello, Dean."
Dean had to blink for a moment to let his brain come back online. "H-hey, Cas. How are ya?"
Castiel gave a small smile. "Better now that you're here. Shall we?" The question was accompanied by him motioning a hand toward Baby.
Dean cleared his throat and nodded and walked back toward the driver's side. How was Castiel so effortlessly attractive? Confidence was seeping from his pores, and it made him so fucking hot.
They drove, making casual conversation about life and the car, until they pulled up in front of a small mom-and-pop diner.
"Does this look good? A buddy of mine owns it. The food is incredible." Dean rubbed the back of his neck, suddenly nervous.
Castiel smiled at him. "Of course, Dean. Will I get to meet him?"
Dean blushed. "O-oh, well, I'm not sure if he's working-"
"I definitely do not have to meet him if that makes you uncomfortable. I was simply making conversation," Cas stated, looking sincere.
Dean sighed and nodded before mustering up the courage to get out of the car. He felt under dressed next to Cas in his blue jeans, work boots, and Henley. He knew he didn't need to dress up for this. He also knew Benny would tease him if he showed up in anything different.
As they walked in, the bell on the top of the door rang, indicating their presence. At the sound, a man with a round face, stubble, and a newsboy cap peeked around the corner. When Benny spent more time in the gay scene, people called him a bear, which Dean had to agree with. The man was large and hairy and muscular, leaving twinks lusting after him wherever he went.
Dean had never been immune to Benny's muscular build and Southern charm, and he and the man had had a short fling before agreeing they were better off as friends.
"Bonjour, cher," Benny said with a grin, locking eyes with Dean for a moment before looking Castiel over. God, Dean would never get tired of the man's Cajun accent. "Who's your date?"
"Hey there, Benny," Dean greeted. "This is Castiel."
Benny fully rounded the corner now and held out a hand for Cas to shake. "Pleasure to meet you." He clapped a hand on Dean's shoulder. "I've known this one for years. Take care of him, alright?"
Cas gave a single nod. Something possessive flashed in his eyes. "Oh, I intend to."
Dean looked between the two of them and huffed out a breath. "Yeah, yeah, Charlie already gave him the "hurt him and they'll never find your body" speech. Can we sit down now?"
Benny chuckled. "Absolutely, mon cher. I'll be out with some menus shortly."
They sat down and Castiel leaned in to whisper, "If I didn't know better, I'd think he was in love with you."
Dean smirked and rolled his eyes. "Yeah, well, we're just friends. But we did used to date years ago." Some sort of emotion flashed across Cas's face, so Dean quickly followed that up by saying, "He's married now. To a woman."
Benny then appeared next to their table, gingerly setting down two menus. He eyed Castiel. "What's your order, hoss?"
Castiel frowned and picked up a menu, looking it over. "I think I'll need a few minutes, actually."
Benny shrugged, and Dean tried to diffuse the situation. "How's Andrea?"
Benny's face lit up at the subject change. "Beautiful as ever." He leaned in slightly and whispered. "We're having a baby."
Dean jumped up and wrapped his arms around the man's neck. "Benny! That's so exciting!"
The Southern man hugged him back. "Thank you, cher. We're really excited."
Dean pulled away and sat back down. "When is she due?"
"September!" Benny beamed. "Still have plenty of time to prepare."
"Happy for you, man. You two need to come over sometime."
Benny looked between Dean and Castiel for a moment before saying, "Double date?"
Dean rolled his eyes. "We'll see how tonight goes, alright? This is only our first date, technically."
Benny hummed and nodded, walking away to give Castiel time to look at the menu.
Castiel frowned down at the menu for a good five minutes before nodding and closing his menu. Then he looked up at Dean. "I think I will have the chicken and waffles. What do you normally get?"
"Usually the chicken and waffles, too, but I like mine Nashville Hot style."
Cas nodded again, considering. "I'm intrigued, but I think I will stick with my gut on this one. It's good, though?"
Dean nodded eagerly and gave him a big, toothy smile. "Benny puts this homemade Cajun seasoning in the batter of the chicken that's incredible. It's still a little bit spicy as it is, but I like mine to make me sweat a little."
The other man smirked at that comment. "I see. Well, maybe sometime soon we can find other ways to 'make you sweat'." There was a glint in his eye that made Dean squirm in his seat. As if on cue, Benny seemed to materialize next to their table.
"You decide what you want, brother?"
Castiel's demeanor suddenly shifted from "teasing dominant" to "innocent patron" so fast it gave Dean whiplash. "I will have the regular chicken and waffles. Please and thank you."
Benny nodded and gathered the menus from the table. "Dean, you're getting your usual, yeah?" When Dean nodded, Benny smiled. "Coming right up." As he left, he gave the younger man a wink – his way of giving Dean shit for his date having a similar order to his own.
Benny had always made fun of couples who both order virtually the same thing. "Where's your sense of adventure?!" he would say. Dean usually just rolled his eyes at him, which was exactly what he did now.
The two sat and talked and laughed through their meal, pausing every so often to acknowledge the deliciousness of the food.
"So… what makes someone decide to tie people up for money?" Dean smirked while leaning forward onto his elbows.
Castiel chuckled, and there may have been a hint of a blush on his cheeks. The man gave a small shrug and paused to think for a moment. "I suppose it just sort of happened. I got into the scene in college after one of my friends told me how much submitting to someone helped her anxiety in the bedroom. So I tried it." He scrunched up his nose a bit and took a small bite of chicken. "Wasn't really my thing. Then I tried being the one in the more dominant role, and…" he trailed off for a moment, presumably trying to gather his thoughts. "I felt like a god." Castiel's eyes sparkled with mischief as he looked over at the submissive man. "I felt more confident than I had ever felt in my life, and it was absolutely intoxicating."
Dean chuckled lightly. "Oh yeah?"
Castiel seemed to compose himself and then shrugged. He picked up his fork again and began poking at his food. "I don't have very good social skills outside of a scene. I'm likely autistic, and having a set of rules and set boundaries is very convenient for me." He then smiled at Dean. "I also love reading the kink lists people fill out. It's like a menu, and all I have to do is choose."
Dean smiled back at him and rubbed the back of his neck shyly. "Well, hey. I'm pretty sure I have that ADHD thing or something. Charlie has it, and she says I do too."
Castiel nodded. "It makes sense why you like submission then. It helps quiet the brain."
Dean nodded too as a couple beats of silence passed between them. "What made you want to do it for money, though?"
"I thought I might be able to help people, as twisted as that sounds. I thought that if this was what helped me, it might help someone else."
Dean smirked. "Like a fucked up sex therapist."
Castiel nodded and chuckled. "Like a fucked up sex therapist, exactly."
Once they finished their meal and paid, they thanked Benny for his hospitality. Dean's eyes almost bulged out of his head when he saw Cas slip Benny a crisp fifty dollar bill as a tip, once again shaking his hand and praising him for his cooking.
—
When they got back into the car, Dean turned the key and looked at Cas. "What's next?"
When Castiel just blinked at him, Dean back-pedaled.
"Or I can just take you home."
Cas sat in silence for a moment. Just as Dean was considering apologizing for saying anything at all, the other man spoke up. "How about we go to my place and have a drink?"
Dean's heart almost started beating out of his chest . "S-sure."
Castiel rested a hand on Dean's knee to get his attention as he started backing out of their parking space. "Again, Dean, I do not intend to sleep with you tonight. I would not be upset if that happened, but there is absolutely no pressure."
Dean nodded, Castiel’s statement doing nothing to calm his jitters. They rode in silence back to Cas's house. Cas didn't remove his hand from Dean's knee until they were parked in his driveway.
The raven-haired man led the way into his house, and slipped his shoes off at the front door. Dean followed suit, unsure if it would be rude not to. Once he stepped further into the home, he took a look around. It looked completely unlike what you would imagine a professional dominant’s home to look like. There were pictures of Castiel with his arm draped around the shoulders of who Dean assumed to be friends and family. In some of the photos, Castiel was tossing his head back with a laugh, and in others, he was smiling fondly at the other people in the frame. In the background of the pictures there were forests and snow-topped mountains and beautiful white sand beaches, but no matter the scenery, Castiel was the most beautiful thing in those frames.
Dean smiled to himself as he examined the photos.
“Those are good memories.”
Dean jumped, not expecting the voice of the older man to come from directly behind him. “Jesus, Cas, you scared the shit out of me.” Once he had calmed, he continued. “Who are these people?”
Castiel pointed to one of him and another man who was considerably shorter than him. The man looked younger, probably about twenty years old, with shaggy blonde hair. “This is my little brother Gabriel.”
Dean smiled. “You two don't really look alike.”
Castiel chuckled and took the opportunity to poke Dean in the ribs. When the younger man yelped, Cas explained, “We were foster kids, but we grew up together so he’s my brother nonetheless.”
“Ohhhh.” Dean felt like his skin was on fire. After Castiel had poked him in the ribs, he had let his hand come to rest on Dean’s hip.
Castiel then leaned in, his chin brushing against the other man’s shoulder. Dean let himself settle in here, allowing Castiel to wrap his arms around his waist and rest his chin fully on his shoulder. Cas seemed to sense that there was some tension, so he spoke up.
“Is this okay?”
Dean swallowed hard and nodded. “Yeah. It’s really good, actually.” He focused his attention back on the photos. “What about her?” The photo was of Castiel and a woman who looked about his age. The woman was slender and beautiful with long light brown hair.
“My sister Anna. She's a year older than me.” He pointed to another photo that Dean had not noticed of him and a man that looked exactly like him. “My twin brother Jimmy.”
Dean laughed. “I didn't know you were a twin.”
Cas nodded against his shoulder, humming quietly. “Most people don’t. I don't talk about him much. He and I don't see eye to eye anymore, though, so we don't really talk.”
Dean frowned. “I thought nothing could separate twins. Don't you have a special bond or something?”
Cas frowned. “Used to. He became a youth pastor, though, and… he's not very cool with me being gay.”
Dean hummed. “I’m sorry, Cas.”
“He’s also pretty pissed that I’m attaching our face to my business. In my line of work, though, you need to be able to have photos of you online and in the building so that people know you’re a real person, but he doesn't get it. I know he tells people he’s an only child so there won't be any chance of them finding his face attached to a BDSM business.” Cas smirked. “It makes me feel like I won that battle slightly.”
Dean laughed. “I think you did win, for sure.”
They stood there in silence for a few minutes. Cas held Dean tighter and they swayed a little bit, still taking in the wall of pictures. After a bit, Dean felt Castiel’s hand push on his hip, no doubt to turn him around. He complied, turning in the other man’s arms to face him.
“I would like to kiss you,” Castiel whispered.
Dean smiled and wrapped his arms around Cas’s neck. “I would like that very much.”
Cas hummed and leaned in, placing possibly the softest, sweetest kiss on Dean’s lips that he had ever received. He never deepened the kiss, just let them continue sharing one small kiss after the other.
After some time had passed, Castiel groaned and straightened up, taking a step back and letting Dean go. Castiel was looking at him with a level of kindness that made him squirm.
“Shall I give you the tour?”
Dean smiled and nodded. “Lead the way.”
Cas took his hand and led him around, waving a hand in the direction of the rooms as they passed. “Upstairs is my bedroom and primary bathroom. This is the guest room, the bathroom, the playroom-”
Dean stopped in his tracks as Cas gestured to a room that had its door closed and locked. “You have a playroom in your home ?”
Cas sighed, as though he was hoping Dean wouldn't ask. “Yes, Dean, I have a playroom in my home.”
“Well, can I see it?”
“You will,” Cas said with a smirk. “Eventually, I'm sure.”
Dean rolled his eyes. “Smartass. I meant right now .”
The older man sighed again, “Alright, fine, since I am apparently hopeless to deny you.” Dean watched as Castiel grabbed his car keys off of the hook by the door and thumbed over to a small brass key. “It's nothing special, I assure you.”
Dean pushed passed and found himself standing in the middle of the room. The space was small, but it had everything. There was a St. Andrew’s cross in one corner, a spanking bench along one wall, a queen sized bed with several very fluffy blankets, a wardrobe to hold… God only knew what. Before he turned to face the Dom, the last thing he registered was a neon sign that read “Yes, Sir!” on the far wall.
“This is awesome,” Dean stated. “This is fucking awesome.”
Castiel shook his head and chuckled, motioning Dean out. “Come on, eager boy. Let's go have that drink we talked about.”
Dean padded out into the living room and flopped himself on the couch, which was a soft, deep brown leather.
Castiel made his way over to the bar cart over in the corner. “Whiskey?” he asked as he pulled out two rocks glasses and uncorked his decanter.
“Please.”
“How would you like it?”
“Neat, please,” Dean responded, and reached out a hand to receive his pour of brown liquor. He was expecting Castiel to sit down, but instead, the man remained standing.
“I didn't ask you hardly any questions about yourself, I’m realizing.” Castiel said, swirling his glass.
“What do you wanna know?” Dean’s tongue poked out to wet his bottom lip. He watched as the Dom’s eyes tracked the motion and darkened. Dean could see the moment he made the decision to do nothing about it.
“I wanna know everything. Your interests, hobbies…”
Dean rattled off a few of his favorite things, from hanging out with his best friend Charlie to his favorite diners with the best burgers. At the end of his rambling, he looked up from his hands that were tucked in his lap to see Castiel sidling up to stand in front of him. Castiel took two fingers and placed them under Dean’s chin, tilting his head up to look at him. Dean let his lips part as he gazed into the dominant man’s eyes.
“You’re so beautiful when you talk about the things you love.” Castiel’s voice was low and deeply exciting.
“I thought you didn't want to have sex with me tonight?”
Castiel smirked. “I said I do not intend on having sex with you. My pretty boy, there is never a time where I don't want to just eat you alive.”
Dean reached out and palmed the Dom through his jeans, noting that he was already hard. He then batted his eyelashes up at the man. “You wanna show me your playroom again?”
Castiel moved his hand so that he was now gripping Dean’s jaw fully. “I don't know. Are you willing to beg for it, boy?”
Dean swallowed and nodded. “Please, sir. Please play with me. Please, I'll be good, sir.”
Castiel leaned down as though he was going to kiss Dean but stopped short. “Such a good boy for me. Go to the room and wait for me on the bed, okay?”
“Yes, sir.”
“Good. Now go. I’ll be there in a moment.”
Once Castiel stepped back and let Dean go, the sub scrambled to obey and bounded into the playroom, instantly stripping off his clothes and getting into presenting position on the bed.
This is a good first date, he thought to himself as he felt subspace begin to fog up his mind.