Work Header

Contracts and Confessions

Chapter Text

Banner with Dean and Crowley


Crowley looked across his desk at his young protégé. Dean was reading through a written offer to transfer with Crowley to Germany. It was a more than generous offer considering Dean only had his B.A. and had not finished his M.B.A. due to financial issues. Relief was clear on Dean’s face, both he and Crowley knew if he stayed at the Ohio office of Sandover after Crowley left, Raphael would quickly find a reason to fire him. Crowley just hoped that the younger man was pragmatic enough not to get caught up in his own bias.

“What do you think, squirrel?” he asked the 22-year-old.

“I think this is awesome,” Dean’s whole face lit up, his moss green eyes sparkling with excitement, “Benny has already settled in Frankfurt and I know can room with him. I can send more money back to help my dad, and I can finish my M.B.A. for free. Seriously, Boss, thank you, I thought for sure I would get the ax after you left. I am going to kick so much ass for you.”

“You know I want you, don’t you, Dean?” Crowley asked. He had been milling over different ways to broach the subject and had decided that blunt was best.

Dean dropped the folder and met his boss’ soft brown eyes, “What?”

Crowley cocked an eyebrow and leaned back in his leather backed chair. “I. Want. You. You are very pretty, this can’t be the first time a man let you know he wanted to fuck, is it, Kansas?”

“First time at work,” Dean responded in a soft voice. Crowley couldn’t help the feeling of disappointment that grew in his stomach. He knew the Midwestern boy would be offended by being desired by another man. Such a pity, Dean was an excellent associate and Crowley could have used him.

“Yes well, I wanted you to know before you moved half way across the world.”

Dean stared for a long moment at the folder splayed across the desk. The job offer had been too good to be true. Slowly he met his boss’s gaze once again, this time his eyes were filled with fury, not excitement. “I am not going to fuck you for this job and fucking hell, I shouldn’t have to. I work hard for you, I am smart and loyal. I get shit done that you can’t do. I charm who you need, take the blame when you need, and come through when you need. You couldn’t have closed that Charleston deal without me. But if you can’t stop thinking with your dick to see what value I bring, then you have nothing to teach me.”

Crowley allowed his eyes to rake over the other man. Dean’s chest was heaving, and his fists were clenched. He painted such an erotic picture. “I am not making the job offer contingent on having sex with you. The job is yours if you want it. It is because I value you and respect my role as mentor that I am telling you this. When you work in a foreign country you get much closer to the Americans than you normally would. Plus, Germany is different, being openly pansexual is more of an asset than being out but discreet. I don’t want you to pack up your life and then be the straight boy panicking because you are desired by men.”

“I’m not straight,” Dean mumbled.

“What?” Out of all the responses, this is not what Crowley had expected.

“I am not straight. I guess I am bi or whatever.”

“Bi or whatever?” Crowley repeated, “Sounds like you’re so far in the closet that you have not really discovered what you are.”

Dean glared at his boss, still confused and very uncomfortable. Yet there was still a spark of hope that this could all be a huge misunderstanding and that everything would work out. “I am not in the closet. My friends and family know. I say bi because it is easiest, but I don’t really identify that way.” Here Dean furrowed his brows. “What’s pansexual?”

Crowley’s smile morphed from mocking to something softer as he explained, “It means I am attracted to people regardless of gender. Not that gender doesn’t matter, or that I don’t see it, just that I appreciate sexy in all its forms. Male, female, trans, genderfluid, non-binary, etc. Does that sound more like how you would describe yourself?”

“God no.” Dean’s face morphed to one of shock. “Shit, I didn’t mean it like that. I wish that described me. It sounds so much clearer. I am not even sure I am LGBTQ, I just know I am not straight.”

Crowley valiantly held back a laugh. God, Dean was young. “Well, what does describe you, Dean?”

“Okay, so I am not anti-trans or anything. I mean Laverne Cox is hot. It’s just I only tend to fool around with guys and date women. And before you rag on my family, it is not them. I tried dating a guy in college, brought him home for Thanksgiving and everything. Only thing Dad said was that adopted grandchildren are still grandchildren, so I had no excuses. But the guy dumped me right after Christmas. Said it was like dating his buddy. And that’s it. Most guys I am attracted to, I don’t even get physical with, we’re just friends. Or sometimes friends with benefits. Most of the action I get with men is random hook ups in a bar. But women, women I can date. Take them out, talk to, get serious with.

“So, I feel weird saying I am LGBTQ. I will probably end up married to a woman with 2.5 kids. I have never been harassed for who I was dating or how I looked. Most people think I am straight. But I am not going to freak out because a guy thinks I am hot or wants to fuck me. But I will freak out if my boss offers me a great job and tells me he wants to fuck me.”

At that Crowley chuckled, “True that was not my most tactful statement. Honestly, I have never coerced someone into sex, and I don’t intend to start now.”

“So, you just going to undress me with your eyes all the time?”

“Do I do that to young Ms. Cassie in accounting?”

“Hell no, course Cassie would have your balls if you did.  Okay, so say I am not concerned with sexual harassment or a hostile work environment. What would happen if I did let you fuck me?”

Crowley closed his eyes and let a shiver run down his back. Dean in his bed, being taken apart bit by bit, eager and inexperienced. “Not a good idea, squirrel. No matter how discrete we were, people would find out. The world is a cruel place and the young, inexperienced one generally pays the price. As long as you work for me, no fucking.”

Dean snorted, “Yeah I think I can live with that, boss man,” and he signed the contract.

Chapter Text

Crowley sighed and ordered a round of shots when he spotted Dean trying to bury his head in the wood tabletop of the bar. They had been living Frankfurt for six months and for the most part it had been going great. While Crowley had an amazing downtown loft with a view of the skyline, Dean shared a cramped one-bedroom apartment with Benny. Yet Dean seemed happy enough with his domestic arrangements, keeping the flat clean while leaving the cooking to the Cajun. Crowley didn’t understand how two attractive, not straight men, could live together without fucking, but once again, Dean was in the friendzone (and yes Crowley had gotten off more than once at the thought of the two young bucks going after each other).  He doubted that was the issue as Dean seemed genuinely happy to have Benny as his friend, instead of lover.

Work was good. They had just closed the Mallory deal and were supposed to be celebrating. Besides if Dean had screwed up at work, he would have admitted it and fixed the issue, none of this wallowing around. No, he only wallowed when he fucked up his love life and was embarrassed. As Crowley hadn’t heard of him doing anything devastating at work, he figured it was school related.

“Okay squirrel, tell Uncle Crowley all about it.”

Dean just groaned in response before a pretty waitress in a low-cut blouse dropped off their drinks. She bent much lower than she needed to and gave the older man an easy view of her rather spectacular breasts.

“Lena will be so mad she missed you, Crowley. Is there anything else I can get you?” she asked in rather accented English, while running a finger up his shirt sleeve.

“Ah Mia, while Lena is sorely missed, I admit that your -delightful- company warms my cockles.”

Dean groaned dramatically, “I am dying here, and you are flirting. Why don’t you ask me what I want, Mia?”

“Because Crowley is much more fun. How about I bring you a stein and a currywurst and you stop moping. Don’t you chicken block me Winchester!” she warned darkly.

Dean smiled charmingly up at the busty server and didn’t laugh, “For you Mia, anything. But it is cock block not chicken.”

“Chicken, cock, both are huhn, yes?” the German asked.

“Cock is schwanz, chicken is huhn,” Crowley explained. Mia giggled and went to place their order.

“Dude how big is your dick?” Dean asked, but Crowley just smirked.

“You will just have to find out for yourself sometime. But size alone does not keep the pretty people telling their friends. It is the entire package. Now tell me what is wrong and drink your whiskey,” Crowley commanded.

“Remember Castiel, my German as a second language study buddy?”

“The Russian?”

“Right. Well I took your and Benny’s advice and asked him out.” Dean admitted.

Friend zoned again?” Crowley truly was shocked. How did such a charming, handsome and intelligent man continue to strike out?

“Worse. He is asexual. But yeah, he really enjoys studying with me and hopes we can hang out,” bemoaned Dean.

“Do you know what asexual is?” Crowley asked.

“Yes… Okay I looked it up. Experiences no sexual attraction; neither wants nor needs sexual contact with another,” Dean answered.

“Generally, yes, but asexual is a spectrum just like being bi is for you. Did you ask him what being ace meant to him?” asked Crowley.

“He didn’t really leave an opening and honestly I don’t want to be that guy. I like him a lot, being his friend is a hell of a lot better than nothing.”

Mia interrupted their rather depressing conversation by dropping off Dean’s plate of currywurst (yes Kansas really did seem to agree with German food). The cook had arranged the sausage so that it made a happy face.

“Sorry your love life sucks, Dean,” Mia offered with a sympathetic smile. Dean gave her a watery smile in return and tucked into his food. “You boys drinking whiskey or beer tonight?”

“Two shots here. He'll have something fancy, with your tiniest umbrella,” said Dean.

Mia just cocked her eyebrow and looked at Crowley, not trusting the crushed pretty boy.

“It is tradition that every time I tell Dean to go for it and he strikes out, I drink something sweet, fruity, and often garnished with an umbrella or flower. It makes him feel better.”

“How often does he strike out?” Mia asked.

“Always,” Dean piped up, his mouth full.

“Not true squirrel, you do very well on the one-night stand front.”

Dean swallowed, “Yeah it is just when they get to know me that folks are turned off.”

Crowley sighed, “I am going to be with this mess for a bit, but if you are free tonight, I would love to spend some time with you, luv.”

Mia smiled. “I am off at 10.”

*          *          *

Hours later, Crowley had dropped a morose Dean off (he was officially Benny’s problem) and gone home to shower and change. It was just after ten when his town car rolled up in front of the sleepy tavern. Mia pops out of the tavern and headed to the car. She had changed out her work clothes and into black, pleather skinny jeans and a backless silver top. She slid into the back seat and right up against Crowley.

“Thanks so much for picking me up. I am so glad to be off and just want to dance and blow off steam.”

“I quite agree with you, luv.” Soon the two were dropped off at a night club. It was cold outside so Crowley wrapped his coat around Mia. She smiled shyly at him. It is a genuine smile in response to an honest kindness. They both know what is going to happen here. Crowley will wave a hand and they will skip the (rather long) line and head straight into the club. A scantily clad waitress will seat them in the VIP section. Crowley will order bottle service and they will do shots of ice-cold vodka. Mia will dance and Crowley will watch. She will bring a few more pretty young things back to the table. They will drink, flirt, and grope each other. It is a give and take, an exchange of abilities, neither taking advantage of the other and both getting what they wanted. But this, a warm coat on a cold night, this is just human kindness.

“Thank you, Daddy.”

An hour later and the night was moving just how Crowley had predicted. Mia has brought two new friends back to the VIP section. A rather muscular young man named Luka and a pretty foreign exchange student named Charlie. Everyone has been drinking, but not past the point of consent, at least as far as Crowley’s rather muted conscious was concerned.

Mia was sitting on Crowley’s lap, grinding on his thigh, while making out with Charlie. Luka ran his hands up and down Crowley’s other thigh. The best thing about the VIP section is that while you have an excellent view of the dance floor, you can also hear each other talk.

“Before we go much farther luvs, I must insist on the consent talk. While you are free to revoke consent at any point you like, much drunker or higher than this and you can’t really give consent. So, what is everyone up to tonight?”

Luka responded first, “I am up for everything, papa. I really want to put this to use,” he said as he stroked Crowley’s impressive and hard cock.

“Topping? Bottoming? Blow jobs? Ladies? Drugs?”

Luka’s blue eyes flashed impossibly dark as they filled with desire, “Yes, please yes, yes, yes and maybe? What kind of drugs?”

“I am sure there is an assortment at my place, but I like trailmix.”

Mia laughed, “Crowley likes to go all night long, Charlie. Well, I am happy for girls,” and kissed Charlie deeply, “Boys,” and kissed Luka with equal vigor, “And blow jobs,” and here she grinded hard onto Crowley’s cock, “But no drugs.”

The three of them then turned to Charlie to see what her limits were, “Oh yum, yeah. Same as Mia, girls, boys, blow jobs,” as she spoke her voice got softer and more mumbled. Crowley arched his eyebrow.

“Now my dear the whole point of a consent check is to see what our partners want. It is fine if you are shy, but don’t agree to something you don’t want.”

“No, no, I am good, I just don’t do drugs.”

“That’s fine, little treasure. I might do some trail mix or just pop the damn blue pill, but there is no pressure. Limits are respected,” Luka tried to reassure her. 

Charlie just smiled shyly and let Mia pull her into another deep kiss. Luka grinned and grabbed Crowley.

“Come on I have to piss,” Luka announced.

“What you need me to hold it for you?” Crowley asked.

“Yes, please,” was Luka’s glib reply.

As they stood in front of urinals, Luka kept glancing over. “Oy, eyes on your own business friend,” Crowley commanded.

“Maybe I just want a sneak peek at the beast.”

Crowley grunted at that, but still he made a show of unzipping his slacks and freeing his heavy cock.

“Wow,” now Luka gave a breathless reply.

“Stop that, it is hard to take a piss with you staring, getting me all hard.”

“It’s so big thought.”

“Feeling nervous, pet?”

“To be honest... a little. I don’t think I have ever had something that big up my ass.”

The guy at the stall next to them snorted and made side eyes to get a look. Crowley couldn’t resist letting him as well. It wouldn’t have been the first time a guy had offered to suck him off in the bathroom after seeing what he had to work with.

“Don’t worry, I know how to use it, and I can be gentle before I wreck your ass.”

Luka quickly zipped up his too tight jeans and washed his hands. “Can we go now? I don’t want to wait.”

Crowley washed up as well. “Do you want a little blue before we go?”

“Yeah, I don’t want to make Charlie feel weird.” They both tossed back the little tab.

“Oh, I think a lot of things are making Charlie feel weird. She is in over her head and doesn’t want to admit it to herself.”

Luka blinked down at the shorter man, “I am too drunk for games. Just tell me what to do, papa.”

“Oh, I love a boy who knows his place. Don’t touch her unless she touches you and be prepared for a stop. And remember, it is not a reflection on you.”

“Got it, let her lead, be ready for no, don’t internalize. But I can touch you right, papa?”

“I would be offended if you didn’t.”

When they got back to the VIP section Charlie are Mia were sprawled out on the love seat together. Charlie was on top, without her top. Her perky nipples were peeking out for her demi bra and Mia as eagerly sucking on one. A guy a few tables over was recording them with this phone. Luka went to deal with the perv, while Crowley got the girls decent.

“You’re so good to me, Crowley, always taking care of me,” purred Mia. “You are a super good guy. Can we go back to your place? I want to eat Red and ride the monster you have between your legs, while Luka chokes you on his cock.”

Crowley groaned low, “Damm it, Mia, I am only human.” Luckily their waitress appeared just then with the slip for Crowley to sign. It included a rather large tip for her service.

“There won’t be any other recordings of my two friends, will there?”

The server glanced at her tip and her eyes bulged a little. “Of course not, sir. The privacy of you and your friends is our paramount concern.”

“Thank you, Letta.”

By the time the quartet made it outside, the town car was waiting for them. Luka grabbed shot gun, while Crowley slid into the back with the girls. He tried to buckle Mia and Charlie in, but they were …difficult. Both of them had lost their shirts at this point and Mia was leaning back onto Crowley’s side as Charlie pinned her down.

“Fuck I love your tits, Mia,” Charlie panted. “They are so lush and just big. I love your nipples. Your pretty, pointy nipples. I love how you gasp and squirm when I play with them,” she rasped out while pinching and flicking Mia’s nipples. Then her mouth was better occupied with sucking and the only sound that filled the town car was Mia’s moans.

Somehow Crowley and Luka got the girls, who had no intent on stopping, into the elevator of Crowley’s parking garage. This time his wool coat was not used to protect Mia from the cold, but both the girls from prying eyes and security cameras. Other people may have been annoyed at the girls’ antics, but both Crowley and Luka chose to be amused. Finally, the foursome spilled into the penthouse. It became clear how much of a show Mia was putting on, when she instantly stopped dry humping Charlie to explore the apartment. Charlie was more affected and left stumbling and panting. Crowley quickly caught her.

“Make yourselves at home,” he called to Mia and Luka as he led Charlie to the kitchen and handed her a water.

“Thanks,” she offered after draining half the bottle.

“Of course. Charlie, if you don’t mind, why are you here?”

Charlie’s eyes flew up to meet Crowley’s gaze. “What? Why? I mean, I am here for the sex and booze.”

“Well I can see you and Mia are hitting it off, but you don’t seem really comfortable here, or at the club.”

“Oh, oh well. Umm... guys aren’t really my scene.”

“Would you like me to have Hans drive you home? Or I could order you an Uber with a female driver if you feel safer?”

“No. I don’t want to leave. I can be fun, I promise.”

Crowley frowned. “I am not kicking you out, Charlie and you already seem fun. But you are at bi/pansexual orgy with both men and women. I intend to fuck both Mia and Luka, and while he and I are fine with not touching you, I don’t think this is your idea of a good time.”

Charlie gave a wry smile, “I appreciate your concern, and I get that I am giving mixed signals. This might be a bad idea, but it is my bad idea. I get that you like being the “daddy” picking up the tab, arranging transportation, protecting the pretty, young things and what not. But in the end, I am an adult. I might be drunk now, but I still know my mind. I knew the minute I met Mia on the dance for that I would end up at your place to have sex with men and women. Please respect my choices.”

Crowley blinked as he processed Charlie’s drunk speech. “Of course.”

Out in the living room, Mia was riding Luka. Condoms and bottles of lube were spread out on the glass coffee table. They had turned on the gas fireplace and had gotten into the vodka. Thankfully, they had left the scotch alone.

Crowley stopped and just watched the two lovers fucking on his sofa. The simple sight of them so erotic with the open blinds bathing them in city light. He leaned against the door jamb as Mia called for Charlie to join them. The redhead quickly removed her pants and panties and climbed, naked, over the couch. She sat on the armrest and spread her legs so that Mia could lick her pussy while riding Luka. Luka moved sideways on the couch so that his legs were spread wide, one over the back of the couch and the other dangled to the ground. It afforded Crowley a perfect view of his thick cock plunging upwards to meet Mia’s greedy pussy.

Crowley poured himself a glass and sat in the wingback chair to watch Charlie wind Mia’s long hair around her fist and pull it back. She used her other hand to balance her body and arched her back, crying out in pleasure as Mia licked and flicked at her clit. Crowley felt his heart pound watching her small tits bounced back and for as she built towards her own orgasm. Mia’s ability to eat pussy with hard cock pounded into her was impressive. Crowley unzipped his slacks and allowed his cock to harden in his hand. These were the moments he lived for, sipping expensive scotch and stroking himself while watching three young and beautiful people pleasure each other.

Mia buried her face deeper into Charlie, licking and nipping, using her teeth and flicking her clit with her tongue. Charlie’s breathing became shallower, as her yips became sharper. Crowley bit back a groan, as he watched his own live action porn shoot.

Then Luka grabbed Mia’s hips and dug his fingertips in. He started pitoning harder into the lush girl. Mia buried her face into Charlie’s sopping wet pussy, just grinding. Charlie roughly pulled her hair, until the three of them climaxed in a mystical puddle together.

Chapter Text

Crowley leaned back in his office chair and allowed his eyes to rake over his half naked employee. Perhaps half naked was wishful thinking, but the beautiful boy was stripped down to his undershirt and a pair of dark washed skinny jeans that were molded to his perfect ass. He was currently holding up two different shirts and trying to decide which invoked the right look for upcoming night.

“You’re lucky you’re pretty, Winchester.”

“Come on boss, you know that I have two looks. Suit or flannel. These afterhours social events are beyond me. Clients I get, you lose the jacket and maybe roll up your sleeves. But a bachelor’s party? I’m lost.”

“Well you better figure it out, you know the Cajun will be expecting you to throw one if he ever gets the nerve up to ask the question.”

Dean laughed lightly, “Yeah, but that’s Benny. I’ll invite people we actually like, wear clothes I am comfortable in, drink in a place we can afford and let you be the best dressed person there.”

Crowley couldn’t help but smile at the thought. Dean was charming, intelligent and damn good at his job. He was also honest with a salt of earth quality that the more jaded man hoped he never lost. Most people sacrificed their good nature in pursuit of wealth and power. Crowley worried for his soul.

“Wear the red, you look good in it, plus it’s expensive but not formal.”

Dean turned and hit him with that 1000-watt smile, “Thanks boss”.

*          *          *

Hours later Crowley found himself at a high-priced steakhouse with a four month waitlist and Wagyu steaks as big as your head. Gabriel sat the head of the table as both the guest of honor and the sacrifice to the marital altar. Despite the no smoking codes, the air was heavy with cigar smoke. Crowley had to admit that Baltazar threw an amazing party. The prices were exorbitant, which Mick, Adler, and Ketch could all afford, but made Dean and Benny blanch. Or would have if Crowley wasn’t shouting for them. Still the boys ordered the second cheapest steak on the menu and Ketch was a prick about it.

Even so, the restaurant was fun, the whiskey smooth and the company, well mixed. Crowley did find it interesting that when he went to discreetly pay for Benny’s share that it had already been covered. Mick met his eyes from across the table as Crowley arched an eyebrow. Apparently, the other Brit knew how to take care of his people. He made a note to keep an eye on this development. Although he and Mick were not in direct competition, losing Benny’s loyalty could be problematic down the line.

Social events like this were always a game of chess, each action had potential for consequences far down the line. Some people found it exhausting, but Crowley thrived on it. The brothel would be a potential landmine, but one he and Dean had prepared for. Or at least he thought he had. The limo pulled up to a rather plain looking building advertising a gay FKK Club.

“Oh, what the fuck is this bullshit!” raged Adler.

Balthazar just laughed. “Oh relax, Adler, they let you wear a robe and there is a bar. Although the pools are sans clothing.”

“Honestly Balthazar, I get the perverse joke with a rather middling brothel, but why a gay one. I know you and Crowley will fuck anything that crosses your path, but Gabriel and I don’t do pork.”

“I thought Gabriel should be with a man at least once before he marries Kali. Although knowing that goddess he will probably find many other opportunities in the future.”

All eyes turned towards the Bride-Groom. But of course, that whiskey eyed trickster just popped a sucker into his mouth and shrugged. “First time for everything. I am sure someone in there can give a good blow job and that is something that Kali does not do.”

“Dude, I get that I am Smallville, Kansas here, but should you really be talking about your fiancée like that?” asked Dean. Adler scoffed loudly, while Ketch rolled his eyes. But Crowley noticed how their boss’ normal smirk turned warmer as he answered Dean.

“Kali proudly announces that she gets on her knees for no man. Balth wasn’t joking, she is a goddess and I am happy to worship at her alter. She also enjoys outsourcing tasks that she doesn’t feel like doing. I think that the only thing she will be pissed about is that she can’t direct my first time with a man. And frankly I am excited to thwart her plans,” Gabriel explained with an evil grin. Dean just shook his head.

“Okay I will be the other Pollyanna in the car, this is exploitive innit?” Mick surprised Crowley by asking. He couldn’t decide if was a genuine question or a ploy to impress Gabriel. Probably a mix of both, as that was Mick’s style.

“Prostitution is legal here. There are laws and such to prevent exploitation. Now can we just get on with this,” Adler snapped as he opened the limo door and got out. Soon everyone had piled out of the limo and made their way to the non-descript building. It was five stories with a store front and sandwiched between a Greek bistro and a wine shop.

Inside the bathhouse was filled with blacklight and neon. A handsome young man wearing just a silver thong greeted them.

“Ahh, you must be Gabriel’s bachelor’s party. We have been expecting you. I understand that this is the first time for some of you. I am Sasha and I am your host for the evening. Your party includes drinks at the bar. All of the employees wear a color wrist band. Feel free to invite them for a drink or to join you in the pool or sauna. There are menus in each room for services à la carte. The color of the wrist band corresponds to the price. We also have private rooms available for a rent if you and another guest hit it off. Everything will be billed at the end.

“Now let me lead you to the changing room where you can use a personal locker to store your belongings. Most of our guests and all of our employees choose to be clothing free, but if you prefer robes are available in the locker room for your comfort. And we have a special one for the bride groom! Which one of you is Gabriel?”

Balthazar quickly outed his boss and Sasha presented him with a gaudy, silk smoking jacket robe, in red with black trim. Soon they all stripped down and made use of the lockers. The Bachelor’s robe was so short that it barely covered Gabriel’s ass. Adler, Benny and Dean all opted for robes, while Ketch and Mick simply wrapped a large towel around their waist. Balthazar opted to go nude from the start, much to the other men’s groaning. Crowley was about to go nude as well until he caught Dean trying to sneak a peek. The younger man had been after his dick for months now, ever since a mutual friend of theirs commented on the size and girth. Crowley wrapped a towel around himself and smirked at Dean’s disappointment.

Soon the men made it out to the main bar where pretty men brought them drinks. They each wore a bracelet: green, blue or purple. While green was just €20 for a blow job, purple was half a grand for a private room and unlimited time. Soon Gabriel zoned in on a tall young man with shaggy brown hair and hazel eyes. He reminded Crowley of a golden retriever puppy.

“And what is your name, moose?” Crowley asked as the boy handed him a scotch.

“It’s Leon, sir,” the boy responded with a wry grin.

“Well my little lion, how are you at giving blow jobs?”

The boy’s face light up as he grinned “Very good sir, would you like me to demonstrate?”

“Actually, my friend is about to get married to a woman who does not give blow jobs ever.”

Right on cue Leon gave Gabriel his best puppy dog look. “Oh, no that is so sad. Perhaps I can give you one so that your cock is not lonely.”

Mick couldn’t hold back a snicker at the line, but Gabriel was gob smacked. Adler stood up, “I have had enough of this nonsense,” he announced and made his way over to the sauna.  Crowley decided not to warn him about what happened in there.

“You know, little lion, that sounds like an excellent idea. I don’t think Gabriel has ever had a boy suck his cock. Why don’t you go over and show him what he has been missing?” Crowley suggested as he tapped the boy’s wrist band, indicating that he would pay for the service.

Leon needed no more encouragement as he crawled down the bench to where Gabriel was sitting. The normally boisterous man was oddly quite as he watched the kid untie his robe and swallow him down. Crowley grinned. He noticed Dean looking uncomfortable and cocked a brow.

“Kid looks like Sam,” Dean whispered. Crowley laughed.

Soon more men were coming by and Crowley ended up with a cute little twink named Samandriel on his lap. He was most likely going to take him upstairs and destroy his ass, but it was a lot of fun to just paw and tease the pretty boy. Of course, part of the fun was calling him Sammy just to have Dean shudder. On one side his brother’s doppelganger was blowing his boss’ boss and on the other a guy named Sammy was calling his boss Daddy.  Dean was so relived to be distracted by another drink that at first, he didn’t notice who had given it to him.

“Cas?!?!” he cried out to the naked man delivering his beer. The incredibly handsome man smiled back at his study buddy.

“Hello Dean.”

Crowley tore his attention from the wanton man on his lap to take in Dean’s elusive crush. Tall, with dark hair and piercing blue eyes, he was every bit as attractive as Dean had described. He also looked both pleased and nervous to see his friend. Both Crowley and Dean seemed to notice at the same time that Cas was wearing a purple wrist band.

“I take it you work here then?” Dean asked, doing a fairly good job of concealing his embarrassment.

“Yes, I do. And you are here for the bachelor party? That makes me very happy,” Cas said as he slid up Dean’s legs to sit on his lap. The light robe did little to conceal his growing erection. Further down on the bench, Gabriel moaned loudly, lost in a slow and sloppy blow job. Sammy wiggled on Crowley’s lap and towel slipped open, freeing his erection to rub against the boy.

“I admit I was excited when I saw you were in this party. I even traded with a co-worker to bring you your drink,” Cas confessed as he slid Dean’s robe off his shoulders and exposed his perky nipples. Crowley kept petting and stroking Sammy’s body, but he could not drag his eyes away from Cas and Dean.

“Oh well, I um, I am surprised to see you. I am just here for the party, not really looking to hire anyone though.”

“That’s okay. It is my job to entertain the customers, and this is entertaining to your party as well,” Cas explained as he ran his teeth up and down Dean’s neck. “Unless of course this is making you uncomfortable. Some people don’t like it when they find their friends work at places like this.”

“We are friends?” Dean croaked.

Cas pulled back from his ministrations and looked into Dean’s eyes. “I think of us as friends. Is that wrong?”

“NO! I think we are friends too. And no, I am not uncomfortable. Or I mean I kind of am but a good uncomfortable, not a I want to pretend that I didn’t see you uncomfortable. I am really, really happy to see you,” Dean rambled.

“Good,” said Cas. He returned to lavishing Dean’s neck with tender licks and soft nibbles as he followed the line of his shoulders down to his hardened chest. He tilted his hips up allowing any passersby a tantalizing glimpse of the sparkly gem stone topped plug nestled between his ass cheeks.

Sammy rolled over on Crowley’s lap so that the two of them were chest to chest. He rubbed his small cock against the older man and leaned up to suck on his ear.

“You like to watch them, don’t you, Daddy?” he whispered.

Crowley nodded. Sammy traced his hand up and down Cas’ back side as Dean dropped his head back and moaned right before Sammy slapped Cas’ ass hard.

“Fuck that is hot,” Mick groaned.

Crowley was so lust dazed that he hadn’t realized the other Brit was still there.

“If Winchester is not tapping that then I am,” he stated as he reached for Cas’ wrist.

“No,” groaned out Crowley as he hit the purple band first. Cas popped his head up, and with lust blown eyes asked, “Hello, Sir, how can I help you.”

Before he slid away from a debauched Dean, Sammy shook his head to stop him. “No, Cassie, Daddy here is very generous with his friends. Look he bought a blow job for the bachelor and I think he wants you to keep playing with Dean, don’t you Daddy?”

It was all Crowley could do to nod. Dean was spread out on the couch, legs wide and cock standing tall and proud. Red streaks and scratch marks sketched across his torso. Sammy’s slight frame was pressed against Cas’ more muscled one. The twink looked at Crowley for a moment then turned back to Cas. Each man sat on the lap of a customer as they leaned in to wrap the other in an embrace. Sammy ran his fingers through Cas’s hair as he pulled him closer before they slowly made out.

When Sammy finally pulled away from the kiss he looked down at Crowley.

“Daddy do you want to play with me?”

Crowley nodded as he tapped the boy’s blue band. Sammy just smiled and helped Cas turn so that his ass was on clear display to Crowley. Dean whined and Sammy stroked his cock while grinding against Crowley. Absently Crowley thought how talented the boy must be to multitask so well. He watched as Sammy’s hand slid over Cas’ body and eased the plug out slowly eliciting a deep groan from Cas as it popped out. With a smile the boy rolled a condom over Dean’s weeping erection and guided him to Cas’ hole.

“Cas,” Dean panted. Crowley noticed the moment they locked eyes it seemed they were the only ones in the world.  “Oh fuck. Cas. I’m finally... inside you. I actually get to fuck you.” Dean’s eyes seemed to glaze over as his mouth continued moving, “You’re so fucking smart, and funny, and —holy shit— so tight, and I get to have this with you.”

“Oh yes.” Cas moaned as he slid down Dean’s cock to the hilt. “Fuck, Dean. You feel so big, stretching me so wide. So good. Fuck me, Dean. Hard.” Cas ordered before he leaned over and kissed Dean passionately.


Crowley couldn’t imagine a moment in his varied life where his dick was as hard as it was in that very moment. He wanted nothing more than to flip Sammy over and ram his cock deep into the boy’s tight ass, splitting him open. But Sammy had other ideas, as he dropped to his knees and devoured Crowley’s cock like a champ. Desire and a hint of jealousy shot through Crowley as he watched Sammy continue to touch and stroke Cas and Dean’s bodies in ways, he himself had only ever dreamed of.

Crowley’s orgasm was fast approaching, he looked over to Cas and Dean, eyes lingering where they were joined, and knew that Dean was just as close as he was. On the precipice of explosion Sammy pulled off his cock and started stroking it furiously, Dean shouted out his orgasm just as Crowley painted Cas’ ass in cum.

Sammy leaned over and used his tongue to clean Cas’ backside before giving the same treatment to Crowley’s head, then he leaned back in a mess of legs with a cum covered grin just for Crowley. Dean slipped out of Cas and held the other man tight as they both settled on the bench. Sammy leaned up and started to suck on Cas’s cock, both of the sex workers still quite hard. Crowley slapped the back of his head.

“Stop that, you naughty boy.”

“But Daddy, Cassie is so hard and so am I. Will you make me cum, Daddy?”

“Hrm, you are very good at your job, my boy. Cas, please take my lust drunk employee upstairs to a private room and enjoy the night. As you for you, my slutty boy, let’s round up a friend or two and take this upstairs as well.”

Crowley lost track of the rest of the bachelor’s party, but he did have a very enjoyable evening and hefty bill in the morning.

Chapter Text

Crowley managed to wait until lunch the following Monday before grilling his protégé and was damn proud of himself for the self-control. But as soon as the phones were off and the take out boxes open he snapped.

“So, squirrel what is the story with tall, dark, and pricey?”

“I don’t want to talk about it.”

“Tough, I paid, I want details.”

“Not much to say,” Dean paused to take a bite of his chicken salad, “We had sex, it was good. Do you want positions or what?”

“Well ideally, but I’ll settle for why he is working there and what it means for you two.”

“It’s a job. Company sponsored his visa, just like Sandover sponsors ours. He came here to be a student just like told me before. He does not advertise where he works, but it is not a secret. He doesn’t experience sexual attraction, but he is not sex repulsed,” here Dean shrugged, “It’s just a job. He doesn’t hate it, and he does not need rescuing.”

Crowley winced a little at the last statement, easily picturing Winchester saying something that required that response. He only hoped it was at least a post coital ramble instead of awkward pre-sex chat.

“So, what does that mean for the two of you?”



“Nothing. He hopes we can still be study buddies, he doesn’t want to lose friends because of this gig and I respect that. And I can’t afford 500 Euros a night to be with him. I have responsibilities, and even if I had that much money to blow, that’s a plane ticket for Sammy to come visit.”

“Blow jobs are a lot cheaper,” Crowley couldn’t help by offer.

Dean paused in his salad and looked his boss dead in the eye, “I will not be that guy. I can’t afford to be Cas’ sugar daddy so I will be his friend. I am not going to creep over on a Tuesday night to get my dick sucked and then copy his notes on Wednesday. I will never be that guy.”

“But he looks so pretty sucking your dick.”

“Ms. Mills is your 2 o’clock,” Dean countered. He grinned as his boss coughed up his club sandwich.

“Jody has an appointment? When am I just finding out now?”

“Cause I told Bela not to tell you.”

“Dean, you lumbering ass, why would you do a fool think like that?”

“Cause you don’t need to stress for a week on end. What you are wearing is prefect. There is nothing else that you could be wearing that will impress her more. I am prepped for the meeting because that is my job. You already know her company inside and out because you are obsessed. We will meet in the conference room, Bela will have tea and those little chocolate cookies, you two will talk while I take notes. From there we will develop a plan on how to best serve her needs. See, knowing in advance will not make anything better.”

Crowley rubbed his hands over his face, his sandwich suddenly tasting like dirt. Dean was right, he knew he was right, but still this was Jody, the most remarkable woman he had ever known. She owned her own international security company, but unlike others in that field, she was good. Not just honest or fair, but morally good. She gave him faith that Dean could be successful and still be Dean. Crowley was not good. He was not honest or fair either. But he did love good people. Just like he loved to take care of the pretty young things that filled his bed, he loved to protect truly good people, especially that did the seemingly impossible. The ones that were successful in business and kept their souls. Jody was all of that and incredibly beautiful, so of course Crowley was obsessed.

“Alright, I don’t like being handled, but I agree we are adequately prepped for her. Let’s make sure that Schultz is managed carefully, if we let him, he will monopolize all our time.”

“The reports are on your desk.”

“Fun. In the mean time I need you to dig into Adler. He is annoying me.”

Dean laughed. “Just because he annoys you does not mean he is doing anything illegal.”

“Ahh, my boy, we are all doing something illegal. Dig and you will find something on everyone,” Crowley responded with a smirk.

“Even you?”

“Especially me. But in Adler’s case I am fairly sure he is spying for Raphael. Gabriel doesn’t need that hanging over his wedding and I want Adler’s parking space. See, win-win,” explained Crowley.

Dean nodded, all traces of the teasing boy gone, replaced by a steely eyed professional, “On it, boss.”

And with that that lunch with over, work resumed, and all thoughts of a pretty blue-eyed prostitute flitted from Crowley’s mind.

*          *          *

The week progressed rather normally despite its dramatic start. Jody had hired t hem for an internal audit and rather basic financial services.  And while Crowley couldn’t shake the feeling that there was something else she needed, he had no idea what. Schultz was proving to be every bit the time suck that Crowley had predicted. At least Crowley was well versed in getting every cent he could in return. Each night Schultz expected to be wined and dined, which was just as well as Jody had refused each night. Tonight, he expected Crowley and Dean to take him to a brothel. Americans, Crowley had noticed, was obsessed with paying for sex. Perhaps it was because prostitution was illegal in the States, or something to do with the way sex was treated as taboo, but privately Crowley thought it had more to do with their desire to own another human. Regardless of the why, Dean, Crowley and Schultz found themselves being dropped off at a rather swanky building on a Thursday night.

This brothel was done up in black leather and red velvet with soft lighting. Most of the employees were nude women with a few men in gold shorts moving around. Again, a host led them to a VIP section of the bar, but unlike the bathhouse, the customers were all fully clothed and none seemed to engage in public sex. As soon as they sat down a lovely, naked woman was bringing them drinks. With a quick nod from Crowley, two busty women sat on either side of Schultz. More naked women came and sat with them, but unlike Gabriel’s party Dean and Crowley were simply there to work. They flirted but just enough to make Schultz comfortable. After all Schultz was a married man, so it was important for him to believe that Crowley and Dean shared his lack of values.

Crowley was barely into his second scotch when a man caught his eye. Checking to see that Schultz was adequately distracted, and keeping his voice low, he asked,

“Say, squirrel, how did you find out about this club?”

“Oh, I asked Cas to for a squawky place with plenty of beautiful women. He said this place was great on a Friday night. I am happy it is this good on a Thursday too. Why?”

“Oh no reason, except I see your school chum at the bar.” Crowley nodded. Sure, enough Cas was dressed in skin tight gold shorts and slinging drinks, not 50 feet away. Dean blanched.

“Eyes on the prize,” Crowley hissed. “Schultz here won’t be very comfortable if you are making moon eyes at your study buddy. Remember that is the point of this whole bloody night.”

“I got it boss. Take a pretty girl upstairs and tell Schultz all about it.” Just as Dean confirmed he knew how to do his job Crowley got a text that made him question his.

All alone. And a picture of a Manhattan cocktail on a Lindner Hotel napkin. Crowley swallowed hard as the text came from Jody Mills. Dean read it over his boss’ shoulder and said, “Go.”

“No, I should stay and take care of Schultz.”

“Schultz is surrounded by hot prostitutes, he is fine. I will handle my Cas problem and Jody is a customer, so it is your job to take care of her too.”


“Boss, trust me. I got this.”

Crowley gave into temptation and nodded his head. He turned to his slimy client and spoke a little louder to be heard over the music.

“Bill, my friend, there is an emergency in China I need to take care of. But Dean and the company card will stay to keep you company.”

Dean laughed and scooped the woman who had been at Crowley’s side onto his lap. “More for me boss. Don’t worry, Bill and I will have a great time while you handle paperwork.”

Schultz laughed, “Yeah Crowley, have fun with China.” Then he turned back to his lovely partners.

Crowley got up and headed towards the exist. Before he got there, he stopped at the bar and motioned Cas over.

“Hey daddy, looking for another party,” Cas purred.

“I thought you were Dean’s friend?” Crowley accused. Cas’ demeaner shifted from wanton to serious and Crowley could easily see him as a buddy of Dean’s.

“I am. Is something wrong? Does Dean need help?”

“You have to know the kind of guy he is. Why did you tell him to come to this club for work and not warn him you would be here?

“He asked for a club with a good Friday night. I never work here on Fridays. Sometimes I fill in at the bar on weekdays. I had no idea Dean was coming here today, nor did I know that I would be here tonight. I am not trying to mess him up.” Cas desperately explained. Crowley sighed.

“Alright, tonight Dean is entertaining an asshole customer, who is would be less than impressed if Dean selected a man for the evening,” Crowley explained as he pulled several hundred dollars out of his wallet. “I want you to help Dean entertain, have lovely ladies attend both men, and otherwise support him. If you end up his in room that is fine by me, as long as the customer does not see. Understand?”

“Da,” the blue-eyed man agreed. And with that little bit of support shored up, Crowley left.

*          *          *

When Crowley arrived at the Lindner Hotel 30 minutes later it was to find Jody sitting at table with another man. She was laughing at something he said, and the man leaned in closer. Jody was lovely as always, wearing a shimmery blue evening dress with a plunged back. He walked straight to her table and stole the open chair.

“So, what are we drinking,” he all but purred out. Jody smiled softly.


“Wow Jody, words cannot describe the disservice your photo does to you.”

Jody couldn’t help but duck her head and blush, recalling the first time they met in person and Crowley commented on how stuffy her official portrait on the company website looked. The man who had been keeping her company bristled at the implied familiarity and the impending loss of his mark.

“Excuse me, but the lady and I were having a conversation,” the affronted German stated. Crowley let his snarky grin spread as he took in the other man. Sleek suit that reeked of cigar smoke, poorly tied tie, rumpled. It was clear he had come from a work meeting, avoiding going home, most likely cheating. Crowley leveled a look and stated; “Leave.”

The man blanched, looked like he might argue, took Crowley in, and surrender.

“Ahh, Jody it was lovely talking to, but I need to go.” Jody just waved her fingers and turned back to Crowley. “I hate it when you do that,” she lied.

“Liar, you love it,” he responded as he waved the server for a scotch. Together they sipped their whiskeys. Crowley reached across the table and wrapped her hand in his. He turned it over and stroked her wrist with his index finger.

“Tell me, Jody Mills, what do you really want from me?”

She smiled softly and touched their hands with her other. “I don’t want to be alone tonight.”

“Well I can help with that.”

Hours later they laid in her hotel bed, Crowley had fetched a damp towel to clean her off and tossed his condom. He crawled back into the bed and wrapped his arms around the woman of his dreams.

“What do you really want of me,” he asked again.

“Nothing you can give,” was the honest reply.

“I think there is a misunderstanding on what I can give. I know that you are alone since Singer retired and Donna went back to the States. What do you want?”

“I want to not be alone anymore,” she repeated. “I want someone I can trust, who will be there for me. I want a partner. And you don’t do monogamy.”

Crowley paused and made sure to listen. “But you didn’t ask for monogamy. You asked for trust, someone to have your back. I can do that.”

“No, you can’t, and I don’t want to make you something you are not. You love being a sugar daddy and I don’t need one of those,” Jody resigned.

“Do you want kids?” Crowley asked suddenly.

“What? No, that ship has sailed a while ago. Anyways, aren’t you a little old.”

“Yes, I am. I don’t want kids either. Do you want to live with a man? Have someone you need to call when you are running late. Be accountable for your time? Share your space and answer to as a partner?”

Jody was quiet for a while. “So, if I don’t want to be owned by a man, I have to be alone?”

“No. And I am sure many married couples don’t feel like they are owned. But they accountable to each other. Is that what you want?”

“I just want to come first. To have someone there. I built this business from the ground up; I am not going to let up now.”

Crowley smiled. “Well now, I can give that, for the right person. I could insist they take a vacation and give my time. Be there on their birthday and holidays and lazy Sundays. I can put them first. I could even live with them, but I think you like living alone.

“I have people who are special in my life,” Crowley continued, “who I have to make time for, just like you do. My work is important to me, just like yours is to you. Just because I don’t do monogamy, doesn’t mean I don’t do commitment.”

“That’s a lot to think about,” Jody said after a while, snuggling in deeper.

“Well sleep and we can talk more later.” He pressed a kiss to the back of her head and drifted off to sleep.

Chapter Text

Crowley in profile with red background

Friday found Crowley with a spring in his step as he made his way into the office. Dean had texted that everything had gone well with Schultz the night before and Crowley anticipated closing with him that day. But even more than seeing the backside of Schultz, Crowley was looking forward to seeing Jody again. He had to leave the hotel early to go home and change. Jody slept through his walk of shame and Crowley couldn’t see waking her. He did leave a note, but he hoped today to see how she felt.

“Morning Bela,” he greeted his assistant. The beautiful woman was marrying money and would be quitting in about six months. Her future in laws were not the sort of people who worked. Crowley was not looking forward to losing such an intelligent asset, but that was a problem for future Crowley. Today’s Crowley had too much to look forward to. “What’s on the schedule for today?”

Bela handed him the daily roster, typed. “Your first appointment is with Mitch at 9:00 am. He has the new ad mock ups. Schultz is at 1:00 pm. The rest is filler,” she explained.

“When is Jody coming in today?” Crowley asked in confusion. He had her down at 10:30, but perhaps she wanted to sleep in.

Bela winced. “She breezed in about an hour ago and asked to meet with Dean. I told her that I could call you if she needed an earlier meeting, but she insisted that Dean could help her.”

“Oh,” was Crowley’s only response.

Getting though his meeting with Mitch was painful, and Crowley admitted that the other Brit didn’t deserve half his snark. But Mitch was a big boy who gave as good as he got and didn’t get hurt feelings. The phone calls dragged out the rest of his morning, but finally it was noon and Dean would be appearing with their lunch. Honestly the thought of grilling his associate was the only thing that got him through.

“Alright boss, I got you a Bacon Avocado Lettuce and Tomato on sourdough. I got Wiener Schnitzel,” Dean announced as he entered his boss’ office and handed him a box. Crowley waited until Dean sat before pouncing.

“Well, how did it go?”

Dean gave a wry smile. “Who do you want to talk about first?”

“Jody.” It wasn’t even a contest.

“I don’t know boss. She came in first thing in the morning, said she wanted to work with me. I did ask why; she bullshitted some then admitted she talked to much last night and felt better working with me. Compartmentalizing and all. She gave me all the specs she wants done. Honestly even with our current workload I can get her finished off by Tuesday. Do you want me to drag it out?” Dean asked as he took a big bite of his fried cutlet.

“No,” Crowley said softly. “Get her done quickly, but with your best service. Whatever is going on between her and I will work itself out in time. Now tell me about last night.”

Dean smiled as Crowley tucked into his sandwich. “Went according to plan. Schultz cheated on his wife, which I have receipts on. Both actual receipts for the credit cards and selfies with Schultz and naked girls. I paid for it all and took company upstairs. Cas did stop by, but he was actually a ton of help. You know, cheating husbands are not my scene, but Cas got a party vibe going.”

Crowley wiped his mouth to tease, “I am sure. Did young Master Cas help you with anything else?”

Dean ducked his head and blushed a little. “Yeah, I paid my study buddy to fuck me, again, and this time on the DL. Fuck, how is this my life?”

Crowley laughed. “Well, I am sure class will be interesting this afternoon.”

“Yeah, not awkward at all,” Dean agreed.

*          *          *

The rest of Friday progressed as predicted. Crowley finished with Schultz, netting a hefty profit for Sandover and tacking enough on the backend to pay for all the schmoozing. Three times over. Dean was studying so there were no Friday night drinks. Crowley left a message and exactly three texts for Jody, all left unanswered. Ball was in her court; anything more would be harassment. So, Crowley did what he always did when he a weekend free. He found pretty young things to shower money, attention and sex on. But with both Jody and Dean floating out there as unobtainable connections, he couldn’t help but walk in Monday morning feeling lonely.

Knowing that Jody was in the building but didn’t want to see him only made the feeling worse. It grew so bad that by Tuesday he skipped lunch with Dean and went out with Balthazar instead. The ass had only laughed when Crowley asked if had lunch plans.

“You poor bastard, both the objects of your affection are huddled together and you can’t have either,” Balthazar teased. “Come on, I know how to cheer you up.”

It was a testament to where Crowley’s head was at that he didn’t even notice that they were at the same FKK club where they had held Gabriel’s bachelor party weeks ago.

“Seriously, I asked for lunch, not a blow job,” grouched Crowley.

“Well here you can get both, along with a scotch. Come on the food is actually pretty good,” Balthazar said.

So, the two men found themselves once again at the bar. Crowley let Balthazar order for him, the bastard had great taste in food, if not clothing, and soon two familiar naked men was bringing them scotch. Crowley couldn’t help the grin that spread across his face.

“Sammy, Leon, what lovely boys.”

Samandriel smiled wide as he handed Crowley his drink. “I am so happy to see you again daddy. Your food will be out in about 15 minutes. Do you want company?”

“Yes, we do,” Balthazar interrupted and tapped both boys’ wristbands, indicating he would pay for sexual services. “Now, Sammy dear, Crowley is down in the dumps. His best girl is working with his number one guy and neither are actually willing to date him.”

“Oh Daddy, that can really hurt. Bet I can make you feel better though,” Samandriel gushed.

“Oh I bet you can,” Crowley growled out as he unzipped his pants and gently pushed Samandriel’s head forward.

Leon turned his big gold eyes on Balthazar, “what about you handsome? Did anyone break your heart?”

“Ahh love, I would have to have a heart for someone to break it. But lucky for you I am a hedonist so I will take a blow job.”

Leon smiled, “good. Sammy and I like to play a game. First one to make their friend cum gets to top tonight. And Sammy has a head start so I will have to work really hard.”

Balthazar laughed as he unzipped his pants and let Leon the Lion go to town. Leon and Samandriel worked hard, licking and sucking and choking themselves, but Balthazar came first. Leon drank him down but didn’t swallow. Crowley could see the cum on his face and in his mouth and that image sent him over the end. Sure, enough Samandriel did the same, catching all of Crowley’s cum in his mouth and then leaned over and kissed Leon. They passed cum back and forth before each swallowing.

“Damm I love cum play,” Crowley growled out.

Samandriel smiled, cum smeared over his face. “Come on Leon, let’s go get their food.” The two boys stood up and held hands as they left.

“Fuck that was hot,” commented Balthazar.

Soon enough the boys returned with hot plates of food and more scotch. Crowley thought how talented they both were to multitask between serving and serving, all while naked. He patted the seat next to him and Samandriel curled up at his side, Leon doing the same for Balthazar. There was something about eating steak and talking with his friend with a naked boy pressed up to his side that made Crowley feel like a medieval king or something equally fanciful.

As Balthazar was settling up, Crowley noticed Cas storming out of a room towards the back. It was clear Cas was very upset and also fully clothed.

“Wonder who pissed his cereal?” Crowley observed.

“Dick is dicking with his hours and pay cut,” Samandriel answered.

“Dick?” Crowley asked.

“Management. They have him working during class times and dropped how much he gets to keep of what each customer pays. I guess their talk didn’t go too well.”

“Does Dick dick with you too?”

“No,” answered Leon, “We are German, so we can always quit and go work somewhere else. It is the immigrants who get screwed. Dick has their work visas and passports. Quitting gets them deported.”

“Tell Cas to give Dean a copy of his contract and I will look it over. But don’t tell Dean what it is or what is going on.”

Samandriel grinned, “I knew you were a good one daddy. And if Dean spends all his time wondering what is going on between you and Cassie, well he should have just dated you and then he would know.”

Crowley laughed. Balthazar was right, the bastard, he did feel better.

*          *          *

The week got better. Jody was no longer in the building come Wednesday and Dean gave Crowley an envelope from Cas. To say his associate was curious was an understatement. But Crowley was sadist and refused to explain. What he saw in the contract made his blood boil and he made an appointment to meet with Dick on Friday night. But the highlight of his week was what Dean gave to him Friday afternoon.

Dean was due to leave for class in a few minutes, so Crowley was surprised he walked into his office with a canary eating grin.

“Who do you love?” Dean asked.

Crowley blinked. “Myself. What’s that you have for me Squirrel?”

“This?” Dean held up the folder. “What could this possibly be? Your birthday present?” Dean opened the folder and pretended to read it over. “Nope, it is too good for that.”

“Oh, my boy what do you have?” asked Crowley again.

“No this is a Dean is the best damn analyst in the world present,” Dean declared as he handed it over. Crowley skimmed the summary memo. “No,” he insisted.

“Oh yes,” countered Dean, looking ready to explode.

“You have proof that Adler has been spying for Raphael.”

“Emails, phone logs, texts and wire transfers,” Dean listed off. “Feeling happy now boss?”

Crowley’s low laugh was his only answer. As soon as Dean left for class, he headed upstairs. Normally he would have preferred to wait, really go over the information and find the best way to exploit it. But Gabriel was leaving for India on Saturday to get married and Crowley didn’t want to wait until after the honeymoon. He paused in his ascent at Kevin’s desk, the young man an excellent assistant and a surprisingly effective gatekeeper.

“He’s busy Crowley,” Kevin said without looking up from his work.

“Interrupt him,” Crowley commanded.

Kevin signed as he turned from his computer to look up at the older man. “Look, Crowley, he is swamped getting ready to leave for the wedding. Please, just save it.”

Crowley leveled the young man with a grim look, “No Kevin, this is important.”

Kevin met his stare for a moment and then swallowed hard. “Yeah, okay give me a minute.” A few minutes wait, and he was waved in.

“Crowley, I love you, but I don’t have time,” Gabriel announced as he scampered across his office.

“Adler is a spy,” Crowley stated calmly, an oasis in a hurricane. But Gabriel just laughed.

“I know you hate the dick, but you can’t have his parking spot.”

“Oh, by the time we are done I will have more than his parking spot, and you will have a new foot stool,” was Crowley’s dry response.

Gabriel finally paused and took in Crowley’s deadly serious visage. Just like Kevin he swallowed hard. Rarely did Crowley drop his sardonic and salty demeanor, but when he did, all were reminded why he was king of the crossroads deal.

“Yeah, okay.  You got proof?” he asked? Crowley just handed him the folder and Gabriel sat down to read. Long minutes passed before he looked up. “Fuck. Winchester did the brief?”

Crowley nodded. “I directed him to look into Adler, this is what he found. I know this is a lot, right before the wedding, but,”

“But there is a very real possibility that my brother will try to take me out at the wedding with the info that Adler has been feeding him,” Gabriel interrupted. “Fuck my family.”

“Indeed. The way I see it you have three options, turn, terminate, or trick.”

A large and deadly smile spread across Gabriel’s face, “Well you know what I am partial to.”

Hours later Crowley left Sandover with a plan and a new energy. Between them the trickster and the demon had a plot that would burn Raphael and destroy Adler. All that intrigue left him hungry for a metaphorical dessert, so he headed back to the FKK club to see a man about a contract.

Chapter Text

After a quick stop at home to freshen up and change into a suit that reeked of power and money, Crowley found himself being dropped off at the same club that a little less than a month started this whole story. Crowley grinned at the same host that greeted them before.

“Hello, Sasha,” Crowley greeted with a low voice. The boy preened.

“Hello again sir. Is it just yourself this time? I think Samandriel is free if you would like me to have him sent to the bar,” the boy offered.

“Thank you, Sasha, but unfortunately this is a business, not pleasure call. I need to speak to Dick rather urgently, I have an appointment.”

“Of course, sir,” Sasha responded before discreetly making a phone call. Shortly after he escorted Crowley to a back office and closed the door behind him.

Twenty minutes later both men emerged. Dick’s shark smile was all teeth, but Crowley knew he had the other man on a hook and there was no escape. Castiel, who had been waiting outside the door, stood up and looked between them. His face was pale, and his worry was evident.

“Castiel, come in,” Dick commanded and the three of them walked back into the office. Dick sat behind his large desk while Crowley continued to stand.

“Mr. Crowley has pointed out some… irregularities in your contract. I decided that it would be in the best interest of the club to allow Mr. Crowley to take over your contract and clear up those irregularities. Now as Crowley here does not run a brothel, you work would be reclassified as that of domestic service. Sign this new contract and then clear out your room.”

Castiel swallowed nervously and then said, “With all due respect sir, I would like to read the contact first.”

Dick stared hard at Cas. “Well if you don’t want to sign, I will just transfer you to the all you can fuck club. I am sure you will enjoy servicing 30 warehouse workers a night. Should leave you plenty of time to study,” Dick threatened.

It was clear that the threat hit its mark, but still Cas held his ground and Crowley couldn’t help but be impressed. “Even so, I need to read the contract before I can sign it.”

Dick waved a dismissive hand and Cas picked up the neatly worded contact that Crowley had written. When he was finished, he looked at Crowley and when the older man nodded, he signed.

“Well now that this drama is done, get your fucking stuff and get out my club. Oh, and Crowley, you’re banned. Step foot in any of my clubs and I will have you arrested.”

Crowley wrapped an arm around Cas’ broad shoulders. “Oh, I am sure I can keep busy.” Together Crowley and Cas walked out of the office and up the back stairs to the employee rooms. Cas lead the way to his sparse, dorm style room. He pulled on a pair of sweats and a tee shirt before grabbing a bag and shoving clothing and other belonging into it. Crowley helped by packing up his school supplies. In under ten minutes they had packed three small bags and every mark of Castiel had been stripped from the room. Two bouncers were waiting for them and escorted them out of the club.

“Do you need to say goodbye to anyone?” Crowley asked.

“No, I’ll text my friends later, they will spread the word,” Cas replied softly. Crowley’s town car was waiting for them and they both got in. The drive to his apartment was mostly quiet. Crowley let Cas be until he noticed the young man was shaking. Gently he rubbed a hand up and down his back.

“Now, now, luv, what’s this all about?”

“Nothing, I am fine. I really appreciate everything you have done. I guess I am a little nervous. I was not expecting to come home with you tonight,” Cas admitted.

“Would you prefer I take you to Dean’s or someone else?”

“No. I don’t want Dean to rescue me, besides his apartment is small for him and Benny, there is no room for me there. I don’t have any friends I could stay with. Anyways, my contract says live in house-boy, so I should start by living in, right?”

Before Crowley could respond they arrived at his apartment. Crowley thought that Cas was too overwhelmed for a building tour or to meet the door man, so they rode up the elevator from the parking garage directly to Crowley’s penthouse. Cas gasped as he took it all in.

“Here, why don’t I show you to your room first, let you shower and settle in and then we can talk, and I will give you a tour,” Crowley offered. Cas just nodded. The guest bedroom was on the other side of the apartment from Crowley and professionally decorated with a masculine feel. It had its own en-suite with a glass shower for two.

Crowley slipped to the kitchen and made a pot of tea. He found some biscuits in the cupboard and put them on a plate, then poured himself a tumbler of scotch. A house boy, what was he thinking? The negotiations with Dick had not gone the way he had expected. He thought he would be able threaten Dick into returning Cas’ pay and hours to how they were originally agreed upon. But Dick’s company had paid moving expenses including filing for visas and were taking payment with interest from Cas’ earnings. When Crowley had seen an opening to get Cas’ whole contract and debt away from Dick, he had pounced, not thinking about the ramifications of having that contract. He could and would release Castiel from his contract, but if he did there was very little stopping Dick from snatching him back up and demanding payment. Honestly Cas staying here was the safest option, if the most complicated.

“Hello, Daddy,” Cas called out, his voice like gravel and startling Crowley. The young man was still wet from his shower, his dark hair was standing on end. He wore a fluffy white towel wrapped around his waist and nothing else. Gone was the scared boy shaking in the car and in his place was a professional bent on seduction. Crowley looked him over from foot to head. Fuck the boy was lovely with bright blue eyes framed by dark lashes and soft, plush lips. His chest was broad and his bisects well defined. He was the same age as Dean, but not nearly the twink that the American was. Crowley wanted him. Honestly what better way to celebrate such a successful day, than to fuck the house boy. Except the house boy was young, scared, and tired. He sighed.

“We need to talk, Castiel. Please go put some clothing out and meet me in the living room,” Crowley commanded and expected to be obeyed. He set the tea on a tray along with the biscuits, sugar, milk and scotch. It was a very Scottish tray and it made Crowley feel more settled.

Castiel arrived in the living room just as Crowley sat down on the couch. The older man poured them both a cuppa and then fixed his with sugar and scotch. Castiel silently added milk and sugar to his cup and snagged a biscuit. They both sat in silence, allowing the healing liquid to work its magic.

“So Castiel, I thought you and I could talk. I wanted to see if you were okay with this.”

“This? You mean being bought? Did you know you could buy a person like that? You didn’t even pay for me, did you? Just walked in and then 20 minutes you own a person. Kind of beyond belief isn’t it?”

Crowley smiled softly. “It is rather amazing and horrifying at the same time. I have purchased a man’s soul, loyalty and time. But never his whole person like chattel. You can of course leave at any time. Unlike your previous employer I will give you your passport and help you find another company to sponsor your visa. But we both know that is not that easy. That any choice you make will have rippled repercussions that can be felt as far away as Russia. And there is little I feel inclined to do about that. You asked for help with a contract negation and I gave it to you.

“So now let’s get down to our business. Besides room and board, which I will provide, how much cash do you need a week?”

Cas named a number.

“Alright and what services will you provide for that number, food and accommodations?”

Cas smiled and leaned back on the couch. “I am very good at sex and you can have it, as much as want, whenever you want. I just need to be able to attend classes, otherwise I will make myself fully available whenever you need me.”

Crowley smiles. “As lovely as that sounds, I have to ask, what else. You already provided sex with many customers, far more sex that I could myself needing from you and I will be providing better wages, food and full run a rather nice apartment, instead of a small dorm with a shared shower.”

Cas chewed on his lower lip and looked over the apartment. “I can clean, I am rather good at it. Run all your errands, pick up dry cleaning, groceries and such. A personal assistant for the home. I can also cook. It is mostly Russian, but I can learn Scottish and American. What is Scottish food?”

“Terrible, worse than Russian. But I rather like the idea of a personal assistant for the home. Maybe even get you a uniform,” he said as he wrote a number on a piece of paper and slid it over to Cas. “Does this work?”

Cas couldn’t stop his eyes from budging a little at the number as he nodded. “Little gold shorts or frilly pink panties?”

“I am partial to panties,” Crowley all but growled, heat filling his voice. “Tomorrow I can teach you how to make my breakfast, go over my schedule and explain how the apartment works. We can get you a key, new cell phone and bank information, I’ll set you up with direct deposit. Also take you shopping for new clothing. You have had an exciting night and a busy day ahead of you, so I suggest heading to bed.”

Cas set his tea down and slid a hand over to Crowley’s knee. “I appreciate that daddy, but I think I would sleep so much better in your arms tonight.” Crowley studied the younger man’s face. Gone was the practiced desire of a man paid for sex. In its place the desire of a man who didn’t want to be alone. Crowley took him by the hand and lead him to the master bedroom, the dishes forgot until morning.

Crowley sat on the bed and pulled Cas next to him. Gently he cupped Cas’ face and pressed his lips against those soft pillows. Cas leaned in closer and opened his lips allowing Crowley’s tongue to enter him. Cas reached forward and slid his hands under the older man’s suit jacket. They held like that for minutes, just kissing, until Cas started to push the jacket off. Crowley let him and then pulled Cas’s tee shirt off. They kept kissing and Cas undid Crowley’s tie and started to work the buttons open. Crowley kept running his fingers up and down Cas’s back, pressing softly, and Cas moaned into the kisses. Soon they were both topless and Crowley eased them down to lay on their sides. Brown eyes stared into blue. They kept kissing and touching, fingers searching out warm flesh and the safety of being held by another person. Soon belts were undone, and buttons were popped. Crowley smoothly removing Cas’ pants, but the other man had trouble around the shoes.

Crowley laughed, low and throaty as Cas started cussing. They had to stop and let Crowley untie his shoes before they could both get naked. And then they were. Naked in Crowley’s own bed. Naked with a man he would live with, who he would be responsible for in a way he never was before. A man who depended on him for safety, for food and shelter. It was an awesome responsibility that honestly had Crowley terrified. But it also excited him, all his nurturing and daddy instincts coming to the surface. He wanted Cas to feel good, to feel cherished, and free.

Crowley traced his fingers up and down Cas’ length as he said, “You are so utterly lovely. So strong. Your skin is soft and firm and very smooth. I love the tufts of hair on your chest and down these muscular thighs. I want to know every inch,” Crowley leaned down and licked a strip down Cas’ chest.

“I want to know you too, Daddy,” Cas admits in a soft voice. Crowley presses Cas down into the mattress and cups both his wrists above his head. He licked and nipped his way past arms, collar bones, nipples, chest, to his tummy. Just as Cas tenses, Crowley blew a raspberry and the younger man laughed Crowley laughed as well and let himself be tackled back into the bed. Cas straddled the older man and took his turn pinning, licking and nipping.

“Oh, that’s my boy. So lovely, so strong,” Crowley moaned, his cock growing hard and ready.

“Damm, I knew you had a thick cock, but that is a fucking python,” Cas rasped out. Then he bobbed his head down and started to lick and suck Crowley’s fat cock, warming himself up.

“Ahhh,” Crowley cried, the pleasure of Cas’ warm mouth wrapped around him. With each stroke Cas took him deeper until he had swallowed the whole cock down. Crowley groaned out and gently ran his fingers though his thick hair, thrusting up to meet Cas’ lips. Then with a loud pop, Cas broke free.

“Where are the condoms?” Cas asked.

“On the dresser, but there is no rush, we could even stroke each other, I want this to be good for you.”

Cas smiled, his blue eyes so alight and excited. “Yeah, I want this, I am excited and ready.” Crowley relaxed while Cas grabbed the condom and lube. He laughed when Cas used his mouth to roll the condom on to Crowley’s aching cock. Then a snap of a lid and both were lubed up. Cas pressed himself down to Crowley’s prone form. For a moment they just pressed and held each other. It was different then the practiced moves of a professional earning this fee, or the wanton hedonism of normal orgies. Instead it felt like the beginning. When a new lover entered his live and they both had to figure out what the other wanted and what they wanted from the other.

Crowley spread his fingers on Cas’ hips and helped him angle onto his waiting cock. Slowly he helped the younger man open up and soon Cas was riding him with abandon. The room was mostly quiet, the only sounds were the squeak of the bed and the grunts of the men. Crowley spread some lube on his hand and started stroke Cas. Soon both men were cumming, Cas spilling his load all over Crowley’s stomach. Cas collapsed next to him and laughed.

“Well that was certainly nice.”

“I am glad you enjoyed yourself,” Crowley replied.

“You don’t mind that I came on you, do you?” Cas asked.

“Not at all love,” Crowley grabbed an undershirt off the floor and wiped himself clean. He then wrapped Cas up in his arms and held him tight, kissing his forehead. “Are you a snuggler?”

“Not normally but tonight I think I would like it. I need to get cleaned up first.”

“Yes, I would like a wet towel as well.” Slowly they separated and went to their own bathrooms to clean and get ready for bed. When Cas returned, Crowley was already wearing black silk pajamas and under the red silk sheets. The overhead light was off and the room was lit by a reading lamp. Cas only wore a pair of boxers and Crowley greatly enjoyed the sight. He lifted the bedspread and welcomed his lover to his side. As soon as Cas was settled, Crowley turned off the light and held the younger man close.

Chapter Text

Crowley woke with Cas still in his arms. The morning sun showed off the man’s face more clearly than he had seen it before. Young, handsome and peaceful in sleep, Crowley couldn’t help but watch him. Soon the pressure on his bladder forced him out of bed and to the bathroom. Since he was up already, he decided to shower. He was slightly disappointed to find a made bed when he came back out, Cas clearly up and about. Crowley dressed for the day and headed out towards the smell of coffee and bacon.

He stopped in the entrance of the kitchen, just watching Cas moving around. His laptop was on the counter and music was lightly playing. But what really set the stage was what he was wearing. Crowley’s only apron, a pair of pink panties and a big smile. A happy boy, at home in his kitchen, wearing panties, it was everything Crowley could want in a Saturday morning.

“What do we have going on here, my boy?” Crowley asked, alerting Cas to his presents.

“Morning Daddy,” Cas crossed the room to great him with a kiss, “So I don’t know exactly what I am doing, but I googled Scottish breakfasts and raided your kitchen. You have whole coffee beans and grinder on the counter, so I assume you like morning coffee. There is a cup waiting for you, but I don’t know how you take it. I found bacon and sausage, so I am cooking both. I have eggs out but I am timing them and I don’t know your style. I didn’t see any tinned baked beans and I didn’t want to try making those from scratch. But I do have tomatoes under the broiler.”

Crowley just laughed. “That sounds marvelous. I have to say I don’t recall you ever saying this much before.”

Cas blushed a little and went back to tend the bacon. “I am excited. I don’t mind sex work and most of the guys I worked with were great. But Dick was just making me miserable. I was so worried all the time about money and school. And I had very limited rights to refuse a customer, even he was a dick or made me feel like trash. This? Being here with you is a thousand times better. I get to cook again! I want to clean and keep this place looking perfect. It is just so nice. And last night….”

“Last night?” Crowley prompted.

“I don’t know, I felt cherished. Like I was having sex because I wanted to, not because it was my sift and I had to. I haven’t been able to do that in so long,” Cas tried to explain while taking the tomatoes out of the oven. “How do you like your eggs?”

“I am not picky, I’ll take them the same as yours,” Crowley answered, and Cas nodded as he started cooking.

“Did Dick have rules against dating?”

“Not exactly, but there was no time, barely enough to study and sometimes meet with friends. I didn’t have a place I could bring anyone, and it was just too much. Plus, I didn’t want to? Sex was work and I couldn’t see doing it in my few off hours. Would you prefer I didn’t date? It wouldn’t be any trouble, but I figured we should go over the rules.”

“No, I don’t mind if you date, and yes we should go over the rules, including yours for me,” Crowley answered as he helped set the table. “I want you to feel like you can bring people over, but I also want to keep my home feeling like it is my home. I haven’t lived with anyone in a long time, I realize that I like my space.”

“What if I text or tell you if I would like to bring someone home. And I keep them in my room. I mean that room is huge, twice the size of my old room. There is a couch and a flat screen. I would like to get a desk at some point for studying, but it is perfect to have a friend or two over and hang out,” Cas suggested as he served up the plates. Together both men sat at the table and tucked in.

“Castiel, this is very good. I think that plan will work quite well. I don’t mind if you use the kitchen or living room either, especially if I am not home. Can we talk about Dean?”

Cas paused mid bite and looked up at Crowley. “What about Dean?”

“Well first, how close are you two? I know from his point of view, but I am curious from yours,” Crowley clarified.

“Dean is my friend. I really care about him. I know he wants to date, but before that was just too much. I do like having sex with him. He talks to me. I know that you two have some chemistry and sexual tension. I know that you are very important to him, he talks about you often. I think that he will be very happy that I am in such a better environment. I don’t know how he will feel about you and I having sex though. Most likely jealous.”

“Is Dean one of those people you would to have over?”

“Yes, very much. Benny is a great guy, but their apartment is small and crowded. We mostly just meet up at the library to study. I love to be able to invite him to hang out in my own room and watch a movie or something. He is so American!”

Crowley laughed, “Yes a Midwestern American. You can have Dean over whenever you want. He has free leave of the apartment. I do care about Dean, not just as an employee or a crush, but as a person. I won’t be jealous if you date him, as long he does not get upset when we have sex.”

Cas nodded at that. “It’s not like we are lovers or anything. I am your mistress and housekeeper nothing else.”

Crowley shook his head. “It’s not that. I am polyamorous. That doesn’t mean I am giant slut or that I like to have sex with many people, although honestly both of those are true. But I like to have relationships with many people. Say I met the perfect lady and we got married. I would still like to have a boyfriend as well. Not as a side piece, but as an added part of the relationship. I would love it if my wife and boyfriend had a relationship too. I work a lot. My career is important to me, but more than that, I love the deal, the chase, the tricks and turns, I love closing. That takes a lot of my time. And the people that I am drawn too, people like Dean, like you, like others, are all very busy people too, with other passions outside of me. If you have a boyfriend and your studies, and you cook, clean, and warm my bed, I will be very happy.

“And if having a boyfriend means you want less personal sex that is fine too. Last night was special. We both had a lot of feelings going on and it was nice to take comfort in each other. But we don’t have to do that every time.

“But now let’s talk about your rules for me. How do you feel about me sharing you with others?”

“What do you mean?” Cas asked.

“Well say I want to host a dinner party, assuming I give you enough notice and budget, how do you feel about cooking, ordering, planning the event?”

Cas perked up. “I would love too. I really enjoy that kind of thing.”

“Great,” Crowley smiled, “How do you feel about me sharing you during sex? Say I bring home some lovely young things from the club, would it be okay for me to invite you to join us? How about if there is someone I want to have a threesome with? I have friends that I have sex with sometimes and I would like to invite them over for drink and sex with my pretty house boy.”

Cas thought for a moment as he ate. “I wouldn’t mind any of that. I like the idea of being invited if you are having a party, being able to say no if I am tired or something. The other thing, inviting a friend over to have sex with me, that feels more like the work at the brothel and I liked the work. I met people and I like sex. I still need the option to say no if the person is a dick or makes me feel like trash. And I would like advance notice so that I can be in the work headspace, but yes, I would fine with that. Could even be fun,” Cas agreed.

“You brought up a few times feeling like trash. What behavior brings that about?” Crowley asked.

“Getting called names or treated like I am stupid. I am not stupid. I speak three languages and I have a 3.75 GPA. If we are playing and you say to your friend what a pretty boy I am or how good I am, that is fine. But when people talk like I can’t understand them or I am just a piece of furniture, that sucks, you know,” Cas explained.

Crowley nodded. They had both finished the rather large breakfast. He helped Cas clean up and showed him how to run the dishwasher. They collected the plates from last night and Cas went to shower and dress. As they were getting ready to leave to get a house key and such Crowley brought up something he had been thinking about since last night.

“Castiel, how do you feel about working tonight?” he asked.

“Sex work? Did you want to invite a friend to play?” Cas asked back.

“Yes. Yesterday, before I ate Dick, I had a very good day at the office. It was in large part due to Dean. I would like to invite him over and both of us have sex with you.”

Cas laughed, “Damn man that is the least sexy invite to a threesome I have ever received.”

“I beg to differ,” Crowley argued, “Consent is very sexy.”

“Alright that is very true,” Cas agreed. “Yes, I consent to having a threesome with Dean. But I am not going to seduce him. I know you two have had some stumbling blocks preventing you from having sex. That is between the two of you. But assuming Dean consents I would very much like to be double stuffed by the two of you. Dean has a lovely dick, not as large as yours, but very nice. I am sure you will love the feel of his dick rubbing against yours as you both stretch my tight hole. The two of you inside me at once makes me very happy.”

Crowley grabbed Cas into a passionate kiss. It struck him that the very nature of their relationship meant that he could kiss, touch and fuck this man whenever the fancy struck. So worth it, he thought as he dropped to his knees and undid Cas pants. The wonderful boy was still wearing pink panties. Crowley wondered if he could get both Cas and Dean to wear matching panties. He licked up and down on Cas’ shaft. The poor boy just moaned, confused and horny. Crowley twisted his tounghe around Cas’ head and he shuddered, leaning forward and holding onto Crowley’s head for support.

Crowley chuckled as he pushed Cas’ cock deep into his throat. He sucked and ran his tongue around the head again and again.

“I’m close. Daddy I am so close. Can I cum? Where can I cum?” Cas begged.

Crowley pulled back with a pop and stroked back and forth, “Cum for my pretty boy, I want you to cum in my mouth so I can feed it back to you,” Cas shuddered at Crowley’s dirty words, “Cum for me and then drink it down you dirty boy,” Crowley taunted before he started sucking more. Cas barley lasted thirty second before he spilled his load, Crowley catching ever drop, then stood up, and kissed Cas, feeding him back his own cum. He held the younger man close as his body shuddered. Finally, Cas spoke,

“Oh Daddy, that was awesome. I love you feeding me my own cum. I hope tonight I get to drink both you and Dean down. Fuck you are hard. Let me return the favor,” Cas offered as he moved towards Crowley’s pants.

“No, no, my boy. I am an old man and I want to be able to perform tonight. Besides we have a lot to do today. I just love having you around.”


Hours later, and Dean was set to arrive any minute. Cas had prepared a lovely tray of meats, cheeses, crackers and spreads. Crowley had beer, scotch and wine. Crowley had to admit, at least to himself, that he was nervous. He had wanted Dean for so long, but it had never been right. Granted he had no plans to fuck or be fucked by Dean today, but to share Cas, that would be meaningful.

Cas was wearing his new clothing; new panties and a new vibrating plug that Crowley controlled with his phone. They had a lot of fun in the sex store, with Crowley now thinking about keeping Cas in chastity. But that would only work if he was not dating anyone. Crowley strongly suspected that Cas would use this night as a test to see if he and Dean could work as a pair. Crowley hoped they could, even if would mean his and Cas’ relationship would be less romantic than it possibly could be.

Cas started to rub Crowley’s shoulders to help him relax before the bell rang and they both knew that Dean was there.

Cas got up and answered the door.

“Hello Dean.”

“Cas, buddy, what are you doing here?” Dean asked, the surprise clear on his face.

“Come on in Dean, there is a lot going on.” Dean followed Cas to the living room were Crowley was still sitting.

“Hey boss, you havin’ a private party?” Dean asked.

“One could say that. Grab a seat, a drink and food, squirrel we have a lot to share.”

Chapter Text

One of the things Crowley loved best about Dean as that he never had to be told twice to eat. The boy was hungry, he shoved food in his face, horny, he got laid, a man of simple of pleasures, he didn’t hesitate to indulge. So, there he sat on couch spreading something on fussy little crackers then stacking them high with meat and cheese. Crowley just watched as Cas pointed out what everything was, the boy so proud to provide and entertain. Both of them more beautiful for being at ease.

“Okay boss, what are we celebrating?” Dean asked as he swallowed a mouthful. Cas poured both of them a glass of wine.

Crowley made a show of looking at his watch. “Well Gabe and I took that lovely file you put together and whipped up some bait for Adler. And the fucker has just swallowed it down.”

Dean laughed as he drank deep from him cup. “And I take it that the bait was poisoned?”

“Oh, most absolutely, but with a delay. You know the kind that you drag back home and poison all your little rat friends with,” Crowley bragged as he drank his scotch.

Dean laughed. “So, Raphael is going down to? This is big, boss, real big. We should be out. Call Benny and Balth. Mitch is pretty decent too.” Dean stood up and started to pace with his drink.

“Ease now squirrel, don’t spill your wine. We can’t spread the word until Gabriel is done. Right now, this stays under wraps. But since you did all the leg work, I felt you deserved a little celebration too, hence the party.”

“Yeah, party of three. What exactly do you have in mind, boss?” Dean stressed the last word as he gave a side eye.

“Well I plan on fucking Castiel here up the ass and I thought you might like to join me?”

Cas pulled off his shirt and tossed it at Dean. He then started to unbuckle his belt. “I’m getting double stuffed! Either you and Daddy or Daddy and a dildo. I do confess I prefer two dicks over a dick and a dildo, but both do leave me feeling so wonderfully full.” Cas smiled with pure seduction. Soon he stood in the room wearing only the pretty pink panties, his cock barely contained.

“Shit, is this for real?” Dean couldn’t help but ask.

“Very,” Cas commented as he climbed naked onto Crowley’s lap and started to unbutton the older man’s shirt. “Now strip,” he commanded Dean.

Dean wasted no time in getting naked and was done at the same time Cas had undressed his boss. “Okay so how do we even do this?” Dean asked.

“Well Crowley has the biggest cock, so he goes in first. I get on top and ride and you stand between our legs and enter from the back. It’s not nearly as complicated as it sounds.”

Crowley couldn’t help but roll his eyes at the level of unsexy in their dirty talk. Cas was hot as hell, but so very blunt. It was rather endearing. Since they were all mostly naked Crowley pressed his body against Cas and pulled his head back so that he could kiss him. Then Dean grabbed Cas’ head and kissed him deeply again. Dean and Crowley held eye contact for a long moment as Cas traced their bodies with his fingertips. Then Cas and Dean pushed Crowley down on the chaise. The two men knelt across him and made out. Cas kept stroking Crowley’s cock as his tongue danced in and out of Dean’s mouth. Crowley slipped Cas’s panties off, freeing his hard cock. Cas popped his ass and Dean saw the thick plug sparkling in his hole. He gripped the rim of it and started pressing back and forth in little movements.

“Damm Cas, your hole is so hungry, just gobbling that plug back and form. It looks so pretty pressing your little rosebud open,” Dean gave a particularly ruthless thrust in and Cas cried out, rubbing his hard cock against Crowley’s equally hard member. “That’s it, baby, you need to be ready to take Crowley’s fucking monster and my cock. And you know that I am not small,” Dean taunted as he slipped a finger in with the plug. Cas howled. “Damm Cas you are such a wanton little slut. So smart and fun and fucking slutty as hell. One cock not enough to you, you got to have two sandwiched in. You want to feel Crowley and me rubbing against each other. Stroking ourselves as we stretch you wide open. You fucking slut, we better get you ready.” Dean grabbed a condom and used two hands to slide it down Crowley’s cock, feeling the entire length.

“Fucking A Crowley that is a monster, a pet python and you are going to feed that whole thing to Cas’ greedy little hole?” Crowley moaned at the feeling of Dean’s hands stroking and fondling his cock. With a final twist, Dean popped the plug out and true to his word he fed Crowley’s cock into Cas’ ass. Both men were panting so hard as intense feelings racked their bodies. Once it was about half way in Dean let go and grasped Cas’ waist helping to thrust him up and down, working more cock in.

Finally, Crowley pressed his whole length deep into Cas’ hole. Dean leaned forward and started to lick and nip as Cas started to ride. Crowley threw back his head and moaned, pleasure coursing through his body. Every time Cas lifted himself up Dean’s hot tongue glided up his shaft until Cas’ hungry hole swallowed it back down. It was a delightful tease that was driving him insane. He watched as Dean stood between his legs and grabbed Cas by his hair, pulling his head back. Crowley kept thrusting his hips up as Dean shoved his tongue down Cas’ throat. It was so erotic to watch the two making out, passion and feelings waring with each other. Crowley grasped Cas’ cock and started to stroke in time with his trusts. Cas’ eyes flew open, but Dean still had ahold of his hair and complete control of his head. The pretty boy was well and truly caught between two predators intent on their prey. Crowley felt more lube being rubbed against his cock and knew Dean was ready. He increased his pressure on Cas’ cock, wanting to keep the boy in state of pleasure. Slowly, so fucking slowly, Dean pressed in. Crowley’s eyes held a laser focus on his protégé’s mouth as it plunged into his houseboy’s lips. That was Dean’s cock rubbing against his. How often he had thought about clasping both their cocks in his hand and stroking, now a beautiful boy’s ass was doing the clasping, but Dean and Crowley were still rubbing their dicks against each other.

With his free hand Crowley pinched and twisted Cas’ nipples, causing the pretty boy to cry out in Dean’s mouth. Dean locked eyes with Crowley and rolled his hips forward sliding his cock against his boss. Crowley lifted his hips and slide back. They were fucking each other inside of Cas. Dean let go of his hair and Cas fell forward, his arms barley holding himself above Crowley, as Dean pushed his full-length in.

“That’s it, Cas, your doing so good. Take my cock. God I can’t believe how amazing you are,” Dean growled out, “FUUUCK Crowley, you are a monster. I knew your cock was big, but this is so fucking much. And Cas, my sweet Cas, you’re just taking it,” Dean thrust hard, “just taking both of us. You are so fucking amazing,” Dean praised. Soon both he and Crowley were working in tandem, thrusting and sliding inside of Cas, who was barely holding on.

“I’m close,” Dean cried out. Crowley picked up his pace on Cas’ cock, stroking faster and twisting as he got to the head. Dean started jackhammering into his study buddy and Cas simply locked eyed with Crowley and went for the ride.

“Ahhh,” cried Cas, his orgasm building. Crowley’s hand matched pace with Dean’s dick.

“That’s it, cum for me, you beautiful slut. Cum hard you fucking, boytoy. Cum with two cocks in that ass of yours,” Crowley taunted. Cas’ breathing picked up and it was clear that he was close to losing. Again, Crowley met Dean’s eyes. He lifted his hips and thrusted hard.

“You feel that squirrel? You feel my cock rubbing against you? Feel it sliding and stroking every inch of your cock. Your friend’s ass is holding is close and I am fucking ruining you.”

Soon both boys were cumming in union. It was one of the singularly most erotic things Crowley had ever seen. As they finished and Dean slipped free, Crowley pulled out as well. He slipped off his condom and grabbed both Dean and Cas by their hair.

“On your knees, my lovely sluts,” he said as he forced them to their knees and stood up. With one hand he grabbed Dean’s head and the other he jackhammered his cock into his hand. Cas, being the ever-good boy he was, simply waited with his mouth open. Soon hot, white, ropes of cum sprayed onto his face.

“That’s it you pretty slut, take my cum, let it mark you,” Crowley shifted and covered Dean’s face in his cum too. As soon as he finished, Cas leaped forward and started licking every drop off of Dean’s face. Dean followed suit, licking Cas and eating Crowley’s cum. Crowley kept ahold of Dean’s hair and forced him down to where Cas’ cum painted his stomach and chest.

“Come on you slutty boy, lick your him clean. You got to play with my toy, you had best clean him up.” Dean needed little encouragement as he licked Cas clean. He looked up at both of them with a big, loopy, cum covered smile. Cas bent his head and kissed him deeply, then turned up and kissed Crowley. Soon they all collapsed on the floor, spent.


Long minutes later Crowley was the first to rise. He grabbed a package of wet wipes and a waste basket to clean himself off, before tossing the wipes to Dean. Soon they were all clean and the condoms disposed of. Dean and Cas still set on the floor, now wrapped in a shared afghan and munching on lovely platter Cas had put together. Crowley sat on the chair near them, sipping Scotch.

“So boss, this was a hell of a thank you. Mind if I crash in the guest room tonight, don’t feel like making the trek home,” Dean asked.

“You’re welcome to stay the night, squirrel, but Castiel has dibs on the guest room,” was Crowley’s response.

“Oh cool, you’re here for the whole night? That’s awesome,” Dean said as he wrapped an arm around the other boy’s shoulder and kissed the side of his head. “How long can you stick around in the morning? I can make you both my famous Winchester breakfast.”

“It’s pancakes and bacon,” Crowley clarified.

“Yeah, world famous pancakes and bacon,” Dean argued back.

“Standard American, overkill breakfast, pancakes and bacon,” Crowley countered.

“Pancakes and bacon that you love, want me to make and will enjoy eating,” Dean declared, playing his trump card. Crowley conceded the point as he did enjoy Dean’s breakfast and he felt he had bought Cas enough time to determine what, if anything, he wanted to say.

“Yes, Dean I will be around in the morning. In fact, I will be around a lot as room and board are part of my salary,” Cas offered.

“Why is the bathhouse paying you to live here?”

“They’re not. My contact has been transferred and I work as a domestic now for Crowley. My official title is Houseboy. Rather nice ring to it don’t you think?”

“Wait, I thought you were working tonight? Are you here because you want to be?” Dean asked with equal parts hope and confusion.

Cas took a deep breath, “Dean I want to you to show me some respect and really listen to what I am saying, before you start judging me,” Cas paused, and Dean nodded in agreement.

“I like sex work. I did it in Russia and I knew I would be doing it here in Germany. No one tricked or forced me. I do know that happens, but it didn’t happen to me. I didn’t like how my boss was taking advantage of me. Because I am immigrant, he could take advantage of me and threaten my visa. He even kept my passport. And if I went to the cops or something like that, he could make trouble for my family and friends back in Russia. Crowley found out about my employment dispute and offered to negotiate on my behalf,” Cas laughed a little. “I don’t think I need to tell you that he is really good at that. We walked out with a new contract, that I signed, with a new job title and employer. I am happy with this change. Okay now you can ask questions.”

Dean smiled a little, but it didn’t reach his eyes. “Why didn’t you tell me you were having contract issues? I could have helped, or gotten Crowley to help sooner,” Dean asked.

“Because, you, my friend, want to save the world. I don’t want you to rescue me, and you would have gone over kill and tried to take down Dick’s whole operation. You are my friend, Dean and we share a bond, but sometimes you just get to gung-ho.”

Dean nodded, not liking what Cas said, but understanding a little. “What would happened if you didn’t sign with Crowley?” he asked in a soft voice.

Cas signed, “Dick would have transferred me to an all you can fuck place. I would not have been able to finish school and he would have used some tricky accounting to keep me working there to pay off debt. I didn’t have a lot choice in coming here, but that doesn’t mean I am not happy.

“I like your boss and I like having sex with him. I freaking love this apartment and I will not mind keeping it clean. I like cooking so making dinner for another person is nice. Instead of having a lot of customers a night, this is just Crowley and the occasional party. And unlike the bathhouse I can easily say no to a party if the other people are assbutts.

“The pay is better, the food is better, I will have more time for school and I can have a life. Dean, I can invite you over to my own room with my own flat screen and we can watch those American movies together. I haven’t had the opportunity to do that since coming to this country. Having a place, I can be proud of, have friends to and belong? This is a big deal for me. Hell, I could even date!”

Dean had started to smile as Cas explained what he liked about his new job, but at the last statement his face froze. “You want to date?” he asked.

“Yes, if I find a guy that can accept that my job includes fucking his boss and I like it, but that is just work and different then sleeping with my boyfriend,” Cas explained.

Crowley just sat drinking and watching the drama unfolding around him. Dean was quite but he held Cas’ hand tightly.

“I need some time Cas. I am happy that you like this job so much and I don’t want to mess this up. You have to know how much I like you, but this is messing with my head,” Dean confessed.

“Why though?” Cas asked, “You still wanted to date after you found out I worked at the bathhouse, now that I have time and in a good place, it is too much for you? That is selfish.”

“Before you were just having sex with strangers. You might have a few regulars, but these were just guys looking for sex. Your living with Crowley!” Dean chanced a glance over at his boss and saw that he was being watched intently. “Fuck it. Cas, if I had your job, cooking, cleaning, fucking and living with Crowley, I would start to develop feelings. So, I am worried that even if we start dating you and Crowley will be more than just a job.”

Crowley blinked at the confession. He could recognize the logic in it. He knew that Castiel was a lovely young man and that it would be hard for him to not develop feelings. The whole thing was needlessly complicated.

“Castiel needs employment to keep his visa. He also needs a place to live. I would be willing to alter the contract to not include room, board or sex. Cas just comes over to cook and clean each day and he can live with you and Benny,” Crowley offered.

“Is that what you want?” Dean asked before Cas could respond.

“Not really. I admit to being excited to have a houseboy. I don’t love living alone, but there are not many people I would like to live with. This arrangement fit my lifestyle very well. But I know how you feel about Castiel and I don’t want to be the reason you lose out.”

“No,” Cas interrupted. “I am not a piece of baggage to be traded between my betters. I am a person capable of choice. I don’t want to be given to Dean to take care of. We are not even dating yet; I don’t want to be his live-in SO earning my keep with sex and housework.”

“But you would do that for Crowley!” Dean interrupted.

“Because that is my job! He is not my boyfriend. Can’t you understand? I want to be an equal partner with my boyfriend. I want to be able to invite him to my space just like he invites me to his. I want to pay for dates, just like he pays for mine. I want to have sex because it is fun and I want to, not because I owe him. Crowley is my boss not my partner. He is a good boss and I like working for him. I feel respected and safe. Can’t you understand the difference? Beside.” Cas paused and looked at Crowley. He shook his head. “Nevermind.”

Crowley cocked an eyebrow. Dean looked between the two of them and sighed with relief. It was clear he knew what Cas was about to say and was grateful for the reprieve.

“Okay, Cas,” Dean said with a soft voice, “Okay, I do see your point. I know it sounds silly considering how much sex we have had but let’s just move slow. Get used to having your own space and freedom. Invite me in. I’ll see that your relationship with Crowley is a comfortable employee employer and we can go from there. I want to watch American movies with you.”

Cas smiled, “I want that too Dean.”

Crowley yawned. “Well as lovely as that was, I want to head to sleep. You both know where the linen is, figure out sleeping among yourselves,” Crowley commanded as he got up and got ready for bed. Some long minutes later he emerged from his bathroom to find both Cas and Dean snuggled up in bed.

“Night Daddy. Dean and I decided your bed is the most comfy,” Cas announced in good boy voice.

“Even a king feels small with three grown men,” Crowley insisted.

“Guess we will just have to cuddle,” Dean responded.

“I guess we will.”

Chapter Text

Over the course of the next week Cas and Crowley developed a routine. Cas got up in the morning while Crowley showered, and made breakfast wearing just an apron and nothing else. They ate together and then Crowley left for work. Cas cleaned, did homework or went to class depending on the day. When Crowley got home, around 6 or 7, a hot dinner was waiting for him along with pleasant company and little clothing. Cas was intelligent and listened with interest to his boss’ day. More than once he had already heard the story from Dean, which was slightly disappointing, but Crowley felt he could deal. The younger man was also surprisingly well-read and informed on current events. Dinner was stimulating and not just because his houseboy was wearing bootie shorts. After dinner Cas would clean up, while Crowley retired to his study with paperwork or reading for work. It was all very domestic, from a time in history well before either man was born.

Yet for all that familiarity in their day to day, the sex was anything but. Kinky, respectful, brutal, exciting, yes, but never intimate. By some unspoken agreement they did not have sex in either of their beds, optioning instead for the living room, study and even kitchen. They certainly did not sleep wrapped in each other’s embrace. While Crowley had enjoyed the intimacy that they had shared their first few days, he knew the depth of Dean’s feelings and didn’t want to stop his young protégé from having a relationship. Crowley wondered if they would work up to using the BDSM playset in his room at some point, but on the whole, he was pleased with the arrangement. Yet sometimes at night as he tried to drift off to sleep, he was reminded that he was not loved. It would be nice to be loved one day.

When Balthazar found out that Crowley had his very own houseboy, he insisted on coming over for a party. Cas quickly agreed, and Crowley suspected the boy felt like he was not earning his keep. Not that Crowley agreed, morning blow jobs and hard fucking during the stock report was plenty for him. Balthazar brought Samandriel and Leon with him and instead of being awkward, it was quite enjoyable. All three men were professionals and recognized they were being paid to be fucked. Completely different then the following week when they turned up at Cas’ invite.

“My, what a lovely sight,” Crowley commented when he got home and saw Cas in his little gold booty shorts pulling out a pot roast. Samandriel and Leon were both dressed casually, Samandriel making a salad and Leon finishing the mashed potatoes.

“Hi Daddy,” came the choirs of replies. Cas sat the pot roast down and turned to properly great his employer with a cocktail and a smile. “Dinner will be ready in a few minutes. Why don’t you get washed up?”

By the time Crowley returned to dining table was set, food laid out and Cas sat across from Samandriel and Leon. Crowley took his place at the head of the table. For a few minutes there was no talking as everyone tucked in. Finally, Samandriel asked,

“Why isn’t Dreamy here today?”

“He and Benny are getting ready for his brother Sam to visit,” answered Cas.

“He isn’t coming for another month and a half,” complained Crowley.

“Well you have seen the apartment; they are just trying to make some more space. Sammy is staying the whole summer after all,” explained Cas.

“Sammy? Is that why you made such an issue of Samandriel Sammy at the bathhouse?” Leon asked in surprise.

Crowley just grinned wickedly, “Oh I do so love to torment my squirrel.” Samandriel laughed. “Oh I will have to play into that next time I see him. You are an evil daddy.”

“Regular demon they say. Speaking of the Bathhouse, how are things? Was there any fall out with Dick?” Crowley asked.

Samandriel shook his pretty head, “Not for us. Dick did have all his work visas audited though. Those that weren’t high performers had their visas terminated. He wants to keep control but still stay in the letter of the law.”

“He didn’t do anything to the German workers?” Cas asked.

“Course not. We have resources. He only fucks with the immigrants,” replied Samandriel.

“Inias and some others are talking to a lawyer for one of the anti-prostitution groups,” confessed Leon.

“And those prudes will exploit the situation for their own benefit,” complained Samandriel.

“You don’t think they have a right to ask for help?” queried Crowley.

“Of course, they do. But that group doesn’t care about a bunch of Russians and Ukrainians. They don’t want them in this country in the first place. The just want to use their suffering to criminalize sex work again.”

“And that would be a bad thing? You wouldn’t have to pay taxes then,” Crowley commented.

“Oh trust me, the government always gets her taxes. Yes, exploitation is hard to prosecute now that it was before. But any system based on the work of vulnerable people will by its very nature be exploitive. You know people working in the garment and agriculture industries are always exploiting cheap foreign labor. Hell, even the tech fields bring in cheap programmers from India so they can pay less wages. Pushing prostitution back into the shadows will only endanger more lives and make it harder to get help,” explained Samandriel.

“I am impressed, Castiel, your friends are both lovely and clever,” commented Crowley.

Samandriel blushed and looked away, “Sorry, I get a little passionate.”

“Don’t be sorry, I appreciate the education. I myself am on a work visa, but I realize that my experiences and Castiel are quite different. I appreciate the well thought out argument.”

“Sometimes Sammy likes to put his college education to use,” Leon said. Crowley blinked in surprise.

“Oh do tell.”

Samandriel simply shrugged. “Not much tell. I graduated, went to college, got my two-year degree and found out I could make a lot more money having sex then working in an office. I haven’t looked back since.”

“Yeah but even without dick, working in a brothel gets old after a while,” commented Cas.

Samandriel countered, “All jobs get old after a while. What is this, pick on Sammy day? Leon, tell everyone you dark secrets.”

Leon laughed and gracefully turned the subject.

After dinner Crowley retired to his study while the boys tidied up. When they finished Cas knocked on the door to his study before coming in.

“Hey daddy, we are going to watch movies in my room and drink good wine. You don’t mind if they crash in my room, do you?”

“Not at all. But you don’t need to hide. You can watch movies in the living room if you like.”

“We like crowding onto my bed,” Cas said as he dropped to his knees in front of his boss. “Makes it all nice and cozy. We like that.” Cas undid Crowley’s belt and unzipped his pants. “Do you like that thought of us all cuddled up around each other, daddy?” Cas stroked Crowley’s cock as it got hard. “Yeah I think you do. Daddy loves the idea of smart pretty boys sleeping together, doesn’t he?”

“Shut up,” Crowley growled and pushed Cas’ head forward until the younger man was swallowing him whole. Normally Crowley would have made him draw it out, maybe even warm his cock while he worked. But he was respectful of Cas’ time and made quick work of his houseboy’s mouth, cumming down his throat.

Crowley popped his dick out and smeared cum around Cas’ lips as the boy swallowed his load. “Yes I do like the idea of the three of you cuddled together. Now go along and give both boys a big kiss from me before you watch your movie.”

“Yes daddy,” Cas answered before leaving the room with a smile.

Chapter Text

Crowley tossed his phone onto his desk as he leaned back into his chair. Cas was game to go out to a club tonight to find new friends. He had just closed a rather large deal with an American banker and felt the need to celebrate. Part of him toyed with the idea of trying to invite Jody out for steak. Dean had been working on a project for her company and Crowley had seen her in the offices a few times. It had been awkward, and he hated awkward. Frankly, there was no reason for it. Yes, they had chemistry and feelings, but Crowley could easily be a woman’s friend if that is what she needed. He wanted to know if she still felt alone. Just as he leaned forward to grab his phone again, Dean meekly entered his office.

“Squirrel,” Crowley greeted, “Aren’t you supposed to be in class?”

“Umm yeah boss, but there was something I needed to talk to you about first,” Dean stammered. Dean never stammered. Crowley grinned. Oh this was going to be fun.

“The answer is no,” he bluntly stated.

“What? But I didn’t even ask anything,” Dean argued.

“You want me to promise to not hit on the littlest Winchester and I simply can’t do it. Sammy is 18 and a high school graduate. That means fair game.”

“No boss, it’s not that. Besides Sammy is taller than me now.”

Crowley cocked an eyebrow. “Really. Well this mythical younger brother sounds better every day. So, you don’t mind me wooing him.”

“No, I don’t mind. You will respect consent and his no. Sammy is straight, so you are not getting anywhere with him,” Dean declared.

“Even if I let him drive my Jag on the Autobahn while I give him a blow job?”

Dean blinked. He seemed to have forgotten that his boss sold sin to saints on a daily basis. “No, please don’t hit on Sam. He is just a kid. And he is stupid. I mean yeah, he got a full ride to Stanford, but that is just because our dad doesn’t make a ton, not because he is smart. I mean he is smart, but you’re Crowley. No seducing 18-year-old farm boys before they have their hearts ripped out in college.”

Crowley just laughed. Suddenly Dean went pale. His eyes glassed over, and he looked away. When he handed Crowley an envelope, he couldn’t meet his mentor’s eyes.

“What’s wrong, Dean?” Crowley asked, sitting upright his chair and leaning forward.

“Just read the letter.”

“I don’t want to read the letter. Tell me what is wrong, Dean.”

“I like it when you laugh. You are a force when you are pissed. I love to watch you rip into a guy who underestimated you. You gave me a chance when no one else would. You have spent so much time and taught me so much. And all that would be fine, you would be an amazing boss, but it would be fine, except you taught me so much more then work. You’re such a bastard most of time, but you have made me a better man. I am so lucky to know you. And now I am going to hurt you. I don’t want to hurt you, but I am going to do it. Because it is better for me. Isn’t that the most selfish thing you have ever heard?”

Crowley stood up and moved around the desk to stand in front of Dean. “I think it is rather beautiful actually,” he ran the back of his hand down Dean’s face as the younger man shuddered. “But I really don’t want to hear what you have to say next. I want you take that letter and burn it and we never speak of this again. If it is money, I can give you a raise. If it is Castiel, we can work it out. I really don’t want to hear what you have to say next.”

“I quit,” Dean whispered. “I have accepted a job at Mills security. It is better pay, better title, more responsibilities. But I know that I could get all that here. Sandover is filled with killers and predators, trickster gods and crossroad devils. I know who and what I will be if I stay here. I want to know if there is another way. If I can be a good man and a successful one.”

Crowley’s face twisted into a myriad of emotions from grief to rage to something that might have been understanding. Before he could say anything though, Dean roughly grabbed his head and pulled him forward into a harsh kiss. Crowley kissed back, deepening, allowing the younger man to explore his mouth and nibble his lips. Dean franticly worked his former boss’ buckle and pants open, freeing his dick.

Dean groaned deeply as he stroked the length of his boss up and down. He had been dreaming about this moment for years and the three way with Cas had not satisfied the fantasy. He pulled the older man’s pants all the way down and took a tiny bottle from his pocket. He popped the cap and smeared lube over his fingers before pulling Crowley’s cheeks wide.

Crowley broke the kiss as Dean’s fingers pressed lube into his hole. “You came prepared.”

“You promised me this back in Ohio. I will be dammed if I don’t collect,” Dean growled out as he undid his own pants one handed.

“I seem to recall promising to ride your ass, not the other way around,” Crowley panted as two fingers invaded his body.

“Things change,” Dean said before removing his fingers. He stared into his boss’ eyes and lifted him onto the desk. He stepped between his legs and pressed his cock inside, never blinking or looking away. It was the eye contact that laid Crowley bare. This beautiful boy that he loved so deeply was pressed inside of him. Slowly rocking his cock in and out as his fist pumped his cock. The only sound in the room was that of their bodies sliding back and forth until Dean broke the silence.

“I love you. I have loved you for so long and I will keep loving you.”

Crowley lifted his hips and thrust back against Dean with such force. The younger man met the challenge and brutally fucked into him all the while chanting, “I love you.” Neither man lasted long, and Crowley came all over his stomach just as he realized Dean hadn’t used a condom.

“Get out. I want your desk cleaned out by the end of day. Don’t bother with two weeks’ notice.”

Dean pulled out and tucked himself in. He grabbed a wetnap left over from lunch to wipe off Crowley’s stomach. “I wish I could plug you full of my cum for the rest of the day,” Dean whispered as he watched his cum leak out of Crowley’s ass. The older man tried to get up, but Dean pushed him down, his eyes still watching the creampie. “My desk is already empty. All my files are updated with complete details on each project and client. I gave Bela a complete run through and introduced my clients to her. Everyone thought I was just preparing to take time off and visit with my brother. No one knew I was leaving.” He let Crowley up and stepped back. He pulled out his name badge and tossed it on the desk.

“I will be gone before security even gets up here.”

“See that you do,” Crowley said. As Dean turned to leave, he couldn’t help but blurt out, “You broke my heart, Kansas.”

Dean turned and smiled looking both breathtakingly beautiful and completely wreaked. “But that is proof you still have one.”

*          *          *

For a long while Crowley sat in stunned silence. Finally, he got up and cleaned himself off in his private bathroom. His protégé has left him for the woman he loved. Not just left him but been seduced away. Before he had thought Jody requesting Dean was a reflection on their relationship, but now he recognized it as a clear opportunity for her to poach his best employee.

Cleaned and presentable he made his way across town to the offices of Mills Security. He made it past the front desk and across the floor with just the storm clouds around him, only to be stopped before he reached Jody’s office by her red headed assistant.

“Sir, you can’t just go in there,” the girl said.

Crowley looked her up and down, it is taking him a moment in his rage to place her. “Charlie, right? You see Mia lately?” he asked. The red head paled and flushed at the same time; her embarrassment easy to see.

“You knew who I was when you came home with me didn’t you? Is that why you fucked a bi girl on my couch? I admit I thought it rather odd why you were there with two blokes when you so obviously preferred the sole company of women. Did Mia know that the only reason you spread your pale legs for her was to spy on me? Poor girl didn’t deserve to be used so.”

“Neither does my assistant deserve to bear the blunt of your temper,” Jody interrupted. “So why don’t we speak in my office.”

“Gladly,” Crowley growled out and he passed Charlie.

Jody sat behind her desk and motioned for Crowley to take the free seat. He declined.

“Charlie is my right-hand woman and friend. I talked about you before I hired you the first time. Charlie didn’t seek you out, but when she recognized you at the club, she got curious how much of the rumors are true and went home with you. She was not spying, more like gossiping. And the gossip was both truthful and flattering.”

“You poached my best employee,” Crowley accused her.

Jody smiled, “I poached your protégée, crush and friend. And you made it easy by not putting a broad non-compete clause in his contract.”

“You used my feelings for you to steal from me!”

“You can’t steal a person; Dean makes his own choices. And I respected your feelings by not seeing you while plotting behind your back.”

“I gave you space to respect your feelings and to ensure you didn’t feel uncomfortable. If you had not slept with me, I would have seen you and Dean coming and been able to stop it!”

“Maybe, but that is your own assumptions coming into play. You assumed everything I did was about you, when really it was about me.”

“I will tear you apart in the courtroom,” Crowley threatened.

“Maybe. Neither Dean nor I have done anything legal. He is not stealing clients or even directly competing. He is just trying something new. But I am very aware of what you can do.”

“And still you choose to do this? Put your whole company at risk? Because believe me, it does not matter that you did nothing illegal. I can ruin you,” Crowley growled out.

“I know. Dean was worth it. You are worth it. Whatever you do, please realize, he is not even leaving you, he is leaving Sandover. That boy will always have your back,” Jody countered.

Crowley sneered. He didn’t know what he wanted and that was a dangerous place for him to be.

“Forgive me,” Jody demanded. Crowley cocked an eyebrow.

“Why would I do a such a magnificently stupid thing like that?” Crowley scoffed.

“Because I want Sundays,” Jody declared as she stood up.

“What?” Crowley asked, her answer confusing him out of his rage for a moment.

“Months ago, in the hotel, you offered me birthdays, holidays and lazy Sundays. You said you could put me first and I could count on you.”

“And you said you needed to think.”

“I did. I liked what I thought about. But I couldn’t ask you to have my back while I was plotting steal the guy that had yours. I did what I did, and my cards are all on the table. I want to have someone to talk to. I want to have good sex with someone who knows what I like and who I don’t have to impress. I want to work hard all week and play hard on the weekend. I want time for my friends. I don’t want to be accountable to someone, but I want Sundays.

“I want to spend lazy Sundays with my lover. I want to read the newspaper and drink coffee. I want brunch and walks in the park. I want dinner with our friends and to go to sleep in his arms.

“I can live with you being a bastard most of time. I don’t need to tell you how to do your work or change your morals. I accept that you have a houseboy that is dating my employee. I know that you will want to have sex with men and woman and that you will spend a good deal of money on them. I value you that love other people, that I am not the only one that you will care for. I hope that Dean will be on that list.

“I require that you protect me from negative consequences of those relationships. I get an STI, I am killing you. Someone has drama, I blame you. I refuse to deal with baby mamas or angry exes although I fully expect you to take care of your responsibilities. I will not be blown off for a hangover or a party. I trust you to manage your money well enough so that we can do the things that we want to. I expect a heads up for any relationships or other information, I don’t do secrets. Can you do that?”

“I need to think,” Crowley said, before he turned and walked out of the office.


*          *          *


Crowley walked. Frankfurt was lovely, all lit up in the setting sun. The warm breeze promised an early summer. Lovers walked down the street holding hands. Men in suits gathered at bars. Women with children laughed. Everyone around him had someone and Crowley had never felt more alone.

He came home early to an empty apartment. Something was bubbling away in the crockpot and Castiel was supposed to be at school. Crowley wondered if he knew. Had he been plotting with Dean? He knew he shouldn’t, but Crowley opened the door to Cas’ room anyways. The bed was neatly made, and the room tidy. Crowley opened the closet and saw the suits he had purchased neatly hung up. He opened the dresser drawers and noticed they only had a few items in each. Some of pictures were missing from the walls. The photos and the painting Leon had done. He swung around and found the lock box in the back of the closet. He had installed it so that Cas could store his passport and other important items. Cas didn’t change the passcode. It was empty. Castiel knew.

Crowley staggered across the apartment and to the bar in the living room. He grabbed the bottle of scotch and sank into the pillows in front of the fire place. He was the master of the deal; he always came up on top. But these people, these horrible, beautiful people that he had welcomed into his home, into his heart, had completely gutted him.

That is how Cas found him, sitting on the floor, watching the fire burn, a €200 bottle of scotch cradled in his arms. He sighed and let his backpack slip off his back, before he padded across the living room to sink into the carpet. For a while they both sat in silence. Finally, Cas spoke.

“Want some dinner to go with that scotch?”

“You here for the rest of your stuff?” Crowley countered.

“Not unless you are firing me,” Cas replied.

“You already moved half out.”

“Force of habit. I just took the stuff I couldn’t leave without. Dean didn’t think you would take it out on me, even if you did kick me out, he was sure you would let me get my stuff. I thought so to, but I just couldn’t leave it all here. Just in case.”

Crowley nodded, still staring at the fire. He took a long swig from the bottle. “So you knew.”

“Yesterday. Dean wanted to give me warning so that I was not blindsided. He didn’t tell me any sooner so that I was not keeping secrets from you,” Cas leaned his head against his boss. “I have to say you are taking this harder than I thought. Did anything else happen?”

Crowley shrugged, Cas’ head moving up and down with his shoulders. “I spoke to Jody.” Cas grimaced picturing the scene. “More like ranted,” he laughed a little. “She wants Sundays. Offered me everything I wanted with her. Now that she has finished plotting against me, that is.”

Cas gasped, “But that is good right?”

“Depends. Everything I want if I can accept being betrayed and knowing that she could always do it again if we are on opposite sides. I honestly don’t know if I can do it,” Crowley confessed.

“Well just make sure that you are not on opposite sides again. Talk it out,” Cas suggested.

“Sounds easy. But I had no inclining that she was planning this, how could I protect myself when we were together?”

Cas was quite for a while. “What are you going to do?” he finally asked.

“Get drunk,” was the response.

*          *          *

 Monday came too early for the bender that Crowley went on. His head was still pounding when Bela brought in their lunch. In an uncharacteristic fit of kindness, she designed to eat her lunch with her boss. Unfortunately for Crowley, Bela didn’t know how to be kind and spent the whole lunch talking about her wedding. So, the knock at his door felt like a reprieve from the torturer’s blade.

“Come in,” Crowley called out, interrupting an in-depth lecture on silk.

A blond boy with a mail cart opened the door and crossed into the room. He was handing Crowley an envelope before he the older man recognized him.

“Samandriel?” Crowley whispered as the boy dropped his head. Crowley had seen this boy in many different ways, naked in bath house, laughing with his friends over dinner, passionately discussing the issues with legal sex work, passionately riding Crowley’s cock while sucking down Balthazar’s. But he had never seen him truly shy.

“When did you start working here?” Crowley asked, his voice gentle.

“Today is my first day. Dean helped me get a foot in the door,” Samandriel explained.

“What about your other job?” Crowley asked.

“I still do it on Fridays and Saturdays. That’s when I made the most anyways. Best of both worlds and all that.”

“Quite,” was Crowley’s only response as he watched the boy quickly retreat. He winked and Samandriel smiled with a soft blush before closing the door. Maybe things were not as bad as they had seemed.

Chapter Text



Midsummer had finally arrived, and every window and door of the penthouse was flung open. Balthazar, Gabriel and Kali, Benny and Andrea, Charlie and Mia, Samandriel, Sammy, and Jody all mingled though the party. Castiel kept popping in and out of the kitchen with more food and Dean manned the bar. Crowley leaned against the railing of his balcony and watched the clear view of his apartment.

“How did you pull this off?” Gabriel asked as he leaned next to him.

“Castiel did most of the work. Boy is a born entertainer.”

“No, I figured that much out months ago. How did you end up a woman as amazing as Jody, a sexy houseboy, and a torrid work affair?”

“Oh, I wouldn’t call Samandriel and I torrid, I am merely mentoring the boy,” Crowley defended himself.

“You are fucking him.”

“But that is just so that Dean can hear me calling out Sammy,” Crowley laughed.

“I know for a fact that you are fucking him over your desk ever lunch.”

“Can you prove that?” Crowley asked.

Gabriel pouted, “No.”

Crowley just smiled.

Balthazar joined them with fresh drinks. “A toast, to Crowley. A man who is well and truly loved.”