Archive of Our Own ^beta

Chapter Text

The windows were fogged up, the air in the confined space humid and thick, in stark contrast to the chill night air just outside. Y/N focused on the cock she was currently riding, hoping to get herself off. Her date kept a steady stream of dirty talk, but she did her best to tune it out, his voice more than a little grating on her ears.

Finding their way to his backseat after dinner, Y/N hoped the strong and handsome man could give her just what her body had been craving. She needed to cum, and not just by her hand or toys as usual. And car sex was usually one of her favorites. Spontaneous, the creaking of the seats, rocking of the vehicle, all giving way to this lustful act.

But it was quickly apparent to her that even though he was packing, he didn’t know what the hell to do with it. He had her laid out on the backseat, his hips pumping a steady rhythm. But he apparently thought his length was enough as he slammed into her again and again.

This was getting her nowhere fast. With a grunt and a light shove, she halted his movements. She pushed and moved him in the backseat until she could ride him, hoping to give them both what they needed.

“Fuck, I’m gonna cum,” he groaned after just a few short minutes, grabbing tightly onto her hips and stilling her movements as he spilled within the condom.

Great -Y/N thought to herself, disappointed at yet another man who couldn’t last long enough to get her anywhere- Why do I even bother?

She reluctantly righted her clothes as her date smiled at her like a dope. Yeah, she knows how great she was. The problem was she couldn’t find a guy that could give her what she needed, no matter how many dates she went on.

Not that she had much time for dates, or interest really. Her career was all that mattered. She didn’t need anyone or anything else in her life. All she needed was a little relief now and again.

But she was striking out again.

Her date drove her home, with promises to call soon followed by an awkward kiss goodnight.

As she entered her apartment, she leaned her back against the door, groaning at her misfortune. Stripping off her layers as she went, she made her way to the bathroom. She turned on the shower, the inviting warmth of the steam filling the small space quickly.

She stepped under the spray, letting it wash over her, chasing away the cold and easing her tension. She wasn’t going to bother with masturbating tonight. It rarely worked anymore anyway, and she did not need to be more frustrated than she was already.

Making her way to bed, she hoped maybe her next encounter would be better.

A week later, she relaxed in her large tub at home, anticipating a quiet weekend. No work that needed immediate attention, no godawful dates to pretend to enjoy. She took a sip of her wine, setting it back on the table she set up by the tub, relaxing back into the warm water, the bubbles giving off a lovely aroma.

Just as she closed her eyes, her phone buzzed on the table. She cursed herself for bringing it in the first place, but old habits died hard.

She sat up, quickly drying her hands and leaning on the edge of the tub as she checked her phone. She perked up, however, when she saw it was an email from The Lion’s Den.

After her failed encounter the week before, she decided to do research on safe and reliable hookups in the area. It wasn’t long before she came across a website for The Lion’s Den, a legalized male brothel in her city.

Intrigued by what the website promised, she submitted an application complete with a photo, hoping to get a coveted interview to become a potential client. The cost wasn’t an issue. She had plenty of money and was willing to spend extra if they were worth it.

Reading through the email, she was elated to find she was accepted for an interview. They wanted to meet with her tomorrow night and scheduled her to talk with someone named Crowley.

She quickly sent a response, confirming the interview. Settling back into the tub she grinned. If all went well, she wouldn’t have to worry about random dates anymore. Hell, by this time tomorrow she could finally have that itch scratched.

When Y/N signed up to join The Lion’s Den as a client, she wasn’t entirely sure what she would be getting. Legalized brothels was a relatively new thing and still gaining ground with new customers. The website provided information, but no pictures.

Arriving at the designated location, she was pleasantly surprised. The exterior was unassuming, except for the security men waiting outside the door. When she gave her name, they opened the door wide for her with brilliant smiles. If the men inside looked anything like the men at the door, she was certainly in for a treat.

The inside, however, was grand. So many people were all around, but it still felt comfortable and not crowded. She let her eyes wander the room. Couples sat about, drinking and chatting, some getting passionate or wandering off to other parts of the facility. She felt charged with energy and ready for a great night.

She was quickly led to one of the tables at the back of the room, her eyes landing on a suited man whose mere presence seemed to command attention.

“Ah, Ms. Y/L/N,” the man stood from his seat, kissing the back of her hand as he greeted her warmly, ushering her into a seat before settling once more.

“You must be Crowley?”

“At your service,” he smirked at her, pouring her a glass of wine from the bottle on the table, “Please, tell me what brings you to our humble establishment, Ms. Y/L/N.”

Y/N grinned as she accepted the glass, taking a long sip and savoring the rich flavor. The wine, the place, the man before her were all high-class and served to only entice her further.

“Please, call me Y/N,” she insisted, “And to be quite frank, Crowley, I don’t have time or patience for the game of dating.”

“Ah, I understand,” he nodded, knowing her background from her application, “But what was the final straw that brought you to us then?”

“You want details?” Y/N asked, a bit surprised at his forwardness.

Chuckling in understanding he nodded once more, “The more I know the better I can serve you and match you to someone who will meet your needs.”

She hesitated, not sure if he really needed to know all of that information. Couldn’t he just match her with someone available that she thought was attractive? Isn’t that how these things usually worked? Not that she knew. But something about him seemed to cast a spell over her, relaxing her and making her feel compelled to tell him.

“Well, it started as a dinner date,” she began after taking a large drink of her wine, “That part was fine enough. Then we drove and parked and I was excited,” she beamed, “Car sex is so spontaneous and fun,” she admitted, gathering herself to continue her story. Crowley was more than a little amused, but was paying rapt attention, “It started off hot and heavy and I was loving it. But then it was clear he didn’t know what the hell he was going, like most men,” she scoffed with an eye roll.

“Mmm, and were you left unsatisfied?” Crowley’s tone dripped with sin and Y/N clenched her thighs reflexively.

“Which is why I’m here,” she smiled warmly at him.

Crowley sat bat in silence as his eyes trailed over her. She felt as if he was undressing her in the most tantalizing ways. She wondered what he had in store for her. If he would be gentle or rough.

“Yes, I think I know just the man for you,” Crowley grinned.

Y/N was confused as she watched him wave someone over to their table, whispering something to the man who nodded and went off, presumably to do whatever Crowley had just told him.

“I’m not here to see you?” Y/N pouted a little, having gotten herself worked up over this man who deliciously filled out his suit and had her wondering what lay beneath.

The smirk he flashed her was pure sex, sending a ripple through her body, “Unfortunately, no. This is my establishment. I like to meet the clients and personally match their needs.”

That made sense, she supposed. Still, it left her disappointed that Crowley wouldn’t be hers for the night. She hoped whatever he had in store for her slaked her thirst.

As Crowley rose from his seat, she followed. He took her hand in his once more, kissing the back of it and gesturing to the assistant from before.

“Kevin will take you to the room where you will meet your date for the evening.”

As instructed, she followed Kevin who lead her up a large staircase and down a hall of several doors. Stopping before one, he opened it wide, gesturing her inside. Before she could thank him, he had closed the door behind her.

Chapter Text

Y/N let her eyes wander over the room. It was small but lavish. Candles were spread around the room, giving a warm and inviting glow. She made her way to what looked like a cross between a bed and a couch, sitting on the edge. As soon as she sat, the door opened and closed once more.

“Hi, Y/N, right?” The man greeted and Y/N’s breath caught in her throat, “I’m Castiel.”

He was beautiful, of average height and build. But his stunning blue eyes and gentle, warm smile melted her heart on sight. He took his hand in hers, kissing the back of it, and Y/N briefly wondered if that was a thing they all did. Not that she minded.

“I’ve never heard that name before,” she responded, mentally kicking herself for her apparent lack of smoothness. “Sorry,” she chuckled lightly, “I’ve never done this before.”

“First timer, huh?,” Castiel said as he sat next to her, opening a bottle of champagne that sat in a bucket on the table before them. He poured them both a glass, handing one to her and lifting his own in a smile, “Well I consider myself lucky then.”

Y/N flushed, ducking her head and sipping her glass, “This kind of feels like a date,” she admitted.

Castiel smiled even brighter, if that was possible, the smile echoed in his sparkling blues.

“It’s my understanding that dating hasn’t gone so well,” Castiel added, setting aside his glass and placing a hand on her thigh above her knee, “So what better way to introduce you than with a date gone right.”

“Well you’re already doing better than the others,” Y/N laughed, Castiel joining her.

They continued to chat, small talk that was all too familiar to her at this point, but she didn’t mind. The champagne and conversation was making her relaxed, and she was more than ready to see what Castiel could do for her.

Setting her glass on the table, she scooted closer to Castiel. He allowed her moves with a smile, patiently waiting to see what she would do. Leaning in she kissed him hesitantly. She pulled back, looking into his eyes and wondering if it was okay.

Castiel grinned, lifting a hand to cup her cheek and bringing her in for another kiss. This one much more intense than the first, it lit a fire within her belly. As his kisses trailed along her jaw and neck, his hands acquainted themselves with her body. She gasped, the sensations revving up that unsatisfied desire within her to near alarming levels.

Her kisses became more urgent and hungry. Without words, Castiel seemed to understand and he began carefully removing her clothes, his lips ever present on her skin as he did. Her head was swimming with his delicate and purposeful touch.

Before long they were bare, Castiel having laid her back on the soft sofa-bed, his lips tasting and worshipping her body.

“You’re so sensitive,” he hummed against her lips, “So responsive.”

Y/N moaned as his fingers found a nipple, gently twisting and tugging.

“You okay?” Cas asked, sending a chill through her naked body.

“Just a little cold,” she smiled reassuringly at him. She didn’t want him to stop whatever was about to happen.

“Mmm, relax, let me warm you up.”

Castiel kissed her deeply before he began a journey down her body. Y/N sighed and relaxed further, though her need was growing more and more unbearable. He kissed down her chest and stomach, his hands holding and squeezing along her sides and hips as he went. When he reached her mound, he sat up once more, leaving her momentarily confused and bereft.

“Can I try something?” he asked, reaching to the table and retrieving one of the lit candles, “I think you’ll really like it,” he insisted, running one hand up and down her side soothingly as he patiently waited for her response.

She’d never really tried this before, but she was familiar with it. She was nervous, but also excited, and willing to at least give it a try. She came here for something other than the norm after all.

Relaxing back, she nodded to him, her fingers running gently over his thighs that were resting under her slightly parted legs. He grinned, leaning forward to kiss her once more. Pulling back, he held her gaze for a moment before looking down at her chest.

Tolting the candle, a small trickle of wax dribbled over the edge, landing along the swell of her breast. She jumped at the sensation, more surprised than anything as the heat of the melted wax quickly cooled against her skin, further hardened by the gentle stream of air Castiel blew over it. She shivered, the mix of sudden heat and sudden cold making her wet.

“Again?” Castiel asked and Y/N nodded, biting her lip in anticipation.

He continued to drip the wax in different areas of her exposed torso, testing her sensations and responses. He would kiss and nip at her skin to soothe or even slightly further ache the areas.

She was beyond riled, his rapt attention and the overload of sensations making her crazy with want. Writhing like a cat, she reached a hand down between them, finding his hard length and stroking slowly.

Castiel moaned in response, seemingly pleased by her actions. His eyes closed and mouth hung open as she worked at him. When he sighed and bit his lip, she decided she was more than ready.

“Want you,” she breathed, releasing him and watching as he quickly sheathed himself with a condom.

Spreading her legs wider, her arms brought him close. He slid in to the root, Y/N moaning at the blissful stretch of him. His lips and hands continued to caress her as he slowly took her apart.

She thought he might be rough or fast, rushing to get through one client to the next. But he took his time, gradually bringing her closer to that precipice she so craved.

When she bucked beneath him, her hands desperately grabbing at his lower back to pull him into her, he knew she needed more. Lifting one of her legs higher and adjusting his angle, he increased his speed slightly.

“Yesss,” Y/N hissed out as Castiel hit all her right spots, bringing her closer to an orgasm than she’d been in forever. He was eager for it, hungry and desperate and feeling mad with want.

The climb was slow and seemed to drag on forever, but when his thumb found her clit and applied just the right amount of pressure, she exploded.

Her eyes squeezed shut, her body clamping down around him as she finally -finally- felt that euphoric bliss that had been denied to her for so long. She had never had one this powerful or last this long.

As she came down from her high, she was met with sparkling blue eyes watching her carefully.

“How do you feel?” Castiel asked as he slowly withdrew, discarding of the condom.

“So amazing,” Y/N chuckled, the broad grin on her face going nowhere soon.

Castiel climbed back into the bed beside her, wrapping an arm around her and resuming his kissing of her chest and neck. It only furthered her bliss, bringing her gently back down to earth.

Once she could move, she quickly cleaned and redressed, Castiel sitting dressed and waiting with a smile. She didn’t feel rushed. If anything, she felt completely in control.

Castiel met her at the door to the room. She smiled up at him, lifting a hand to cup his cheek and pecking his lips sweetly.

“Thank you, Castiel.”

“Hope to see you again. Soon.”

She smiled and thanked him again, making sure she was presentable before making her way back downstairs. Crowley was in the lobby and greeted her as she came down.

“Ms. Y/L/N,” Crowley grinned, his eyes travelling over her and seeing a new glow and less tension, “Can I offer you another drink?”

“No, thank you,” she beamed, “I need to head home. But I hope to be back very soon.”

“Excellent news, and we look forward to seeing you.”

Y/N made her way out of the bar and back home, feeling exhausted by the time she shut her front door. But it was more than worth it. Every penny. She was grateful they simply kept a card on file and emailed receipts. So anytime she went there, all she had to do was enjoy her time.

She was definitely going back again. As soon as she had another free night.

Chapter Text

It had unfortunately been several weeks before Y/N was able to find the time to return to The Lion’s Den. Work had kept her constantly busy, with long hours and barely time to sleep, let alone other activities. She was wound up and itching for a way to ease the tension. So when Crowley confirmed her appointment for that evening, she was ecstatic.

“Ms. Y/L/N,” Crowley greeted, helping her into a chair at his table, “Always a pleasure.”

“So when do I get a chance with you?” she flirted, grinning broadly when she saw his flushed response.

“Hmm, maybe one day,” he smiled, “So what is it you’re looking for this evening?”

“Well,” Y/N shrugged, disappointed that Crowley wouldn’t be hers. Maybe she’d eventually get him, “Last time was absolutely lovely,” she beamed, “But this time I think I’m craving…more.”

“More?” Crowley asked with a raised brow.

“More everything, but different,” she confessed excitedly, “I’m not really sure. Just…more.”

Crowley grinned, eyeing her for a moment before gesturing for the young man, Kevin, to come to their table once more. He whispered to him and Kevin went off as before. Crowley rose, helping Y/N from her chair and slowly walking her across the lounge to the staircase.

“I hope you have an open mind,” Crowley offered once more, handing her back over to Kevin when he returned.

The room was not what she expected and completely different from last time. It was colder and industrial, the walls made of concrete. There was a firm black leather bed in the middle of the room, a column with straps off to the other side. As the door closed behind her, her eyes fell on the man in the room.

Unlike before, her date for the evening was already waiting for her. A tall man, with large and defined muscles, longer hair, and well over six feet of pure fuck me. He was shirtless, dressed only in a pair of loose track pants.

“I’m Sam,” the man introduced, taking her hand in his own and kissing the back of it, his eyes never leaving hers.

He was enormous, dwarfing her entirely. His gaze was intense and she felt like whatever was to follow would be as intense as that look.

“Y/N,” she mumbled in response, still in awe of the man before her.

“Are you experienced with any play or kinks?” he asked, his long fingers trailing down one side of her neck and collarbone as his lips and hair tickled the other.

“N-not really,” she responded, her throat feeling dry. Play and kinks? Her gaze drifted to the column with straps and she clenched her thighs.

He hummed, gently leading her backward until her back hit something firm. She realized she was pinned against the column from before.

“Would you like to try?” he asked, his lips still teasing her neck and collarbone, his longer hair tickling her skin.

“Yes,” she admitted, though a bit shy and embarrassed but the smile he graced her with made her feel infinitely better.

“Would you let me restrain you? Do with you as I please?”

Fuck. Suddenly it was all she wanted.

“Yes.”

Sam took several steps back, his eyes devouring her from head to toe.

“Strip,” he commanded, his gaze steady and arms crossed as she waited.

The tone in his voice left no room for argument and she did as commanded. Once bared to him, she waited for whatever he wanted from her next. She wanted to please this giant of a man and have him use her.

He approached her then, pressing her back into the column as he kissed her for the first time. It was passionate and rough and just what she needed. She responded eagerly, kissing him back just as hard, allowing her fingers to tangle in his luxurious locks. He pulled back suddenly, spinning her to face the column.

She gasped as his hands trailed down her arms to her wrists, lifting them above her head slowly. He shifted so both her wrists were held in one of his large hands.

“I’m going to restrain you,” Sam whispered in her ear before biting at the lobe, “I will use colors for your first time,” he explained, his hot breath fanning over her, “Green means you’re good, yellow means you need a minute, and red means stop. If you say yellow or red I will stop everything until you tell me to continue. I want you to be comfortable and safe above all else. Understand?”

Y/N nodded, but Sam wanted more.

“I need you to use your words, Y/N.”

“Y-yes, I understand, Sam.”

“Good girl,” he praised and she loved the sound of it.

Sam tied her hands together and to the post with the attached straps. Once her hands were secured he teasingly trailed his hands down her body until he was kneeling. He gently spread her legs retraining each one in a strap. When he was done, she was wide open and exposed, unable to see him or know what was coming.

It made her heart pound in her chest. She tested her bindings, finding very little give and doubting she’d be able to release herself if needed.

“How does that feel?” Sam asked.

Y/N tested her bindings once more, “It’s not too tight,” she tried being positive.

“Are you okay? Do you need a minute?”

Y/N paused, taking a deep breath. It was just different and new and exciting all at once. But she had a feeling it would test her limits in the best of ways and be memorable.

“I’m good,” she breathed out, feeling the tension seep from her as she did so, “Green,” she added with a smile.

“Very good,” Sam praised once more as he stood behind her.

His hands went from her waist, trailing over her hips to come around and cup her ass. She moaned at the feel of his large, warm hands.

“Such a beautiful ass,” Sam commented as he leaned in to whisper in her ear, “Can I spank you?”

The slight growl in his whispered tone sent chills through her. She’d been spanked before and liked it when done right.

“Yes,” she half-breathed, half-moaned, desperate for him to do something, anything.

She heard the first smack before it truly registered. She jumped from the sting of his hand, large enough to cover the whole cheek as he slapped. Another slap on the other side made her jump once more, but an involuntary moan pulled from her throat. The sting was sore, but the burn was pleasurable, his touch strong but controlled. She knew he could do more, but he wasn’t aiming to hurt her. Once she realized that, she was in the zone and completely surrendered to Sam’s will.

Several more smacks and her ass was burning, but her arousal was dripping down her thighs. She needed this more than she realized. Somehow, despite the pain or the situation, it relaxed her, easing the tension and stress from her body.

“So beautiful,” Sam admired the red of her cheeks, massaging them with his hands.

He pressed his body to hers, his hands reaching around to find her nipples. As he began to twist and pinch them, making Y/N cry out, he rutted himself against her aching backside. She gasped at the feel of him, so large and hard, his thin pants doing little to conceal his excitement.

One of his hands left her breast, his touch slow and firm as he dragged his hand down the front of her body. As he reached her mound, her breath hitched. His fingers found her slit, dipping into the wetness he found there before gently swirling around her sensitive nub.

Y/N gasped harshly before moaning, her thighs quaking as she attempted to clench them. She hadn’t realized just how wound up the spanking and his touch had gotten her.

“So fucking wet for me,” Sam breathed against her neck, nipping at her shoulder and making her hiss, “Gonna fuck you good and hard,” he promised, making her moan in anticipation once more.

Sam stepped away from her, leaving her bereft of his touch. She could hear the rustling of clothing, but Sam remained just out of sight. Part of her lamented the fact that she wouldn’t see him as he tore her apart.

That part of her was silenced as she felt him press himself against her again. His length, now released from its confines, pressed against the crack of her ass. She could feel the weight and length and thickness of him, causing her to squirm against him, silently begging for him.

“This what you want?” Sam asked, teasing his condom-covered length against her entrance.

“Yes, please,” she shamelessly begged, trying to buck her ass against him but finding little room to move with her restraints.

“Then take it,” he growled into her ear before slamming deep into her core.

A guttural groan ripped from her throat as he slammed home. Giving her no time to adjust, Sam began a brutal pace. The sounds of skin slapping against skin echoed in Y/N’s ears, mixing with her desperate moans and screams of pleasure.

She came quick and hard, screaming her release into the void, but Sam didn’t relent. He went harder, faster if it were even possible, continuously pummeling her core with his shaft, nearly lifting her off the ground with its force if she wasn’t tied in place.

“Again,” Sam demanded, his grip tightening on her hips.

She couldn’t fight it, the second orgasm ripping from her body without notice, following his command without her permission. Her eyes squeezed shut, she could only make inhuman sounds as Sam rode her through her high.

She wasn’t sure if the orgasm continued or launched into a third under Sam’s continued ministrations, but her mind was too blissed out to care about any of it.

Sam stilled with a vicious roar, his length buried deep, his hands squeezing her hips so tightly she knew there would be bruises. When he pulled out, Y/N slumped in her bindings, her body thoroughly spent and high on pleasure. Her whole body shook and twitched with the aftershocks of her orgasms, her breath stubbornly refusing to calm.

She allowed herself to lean against the pole, the strength went out of her. She felt Sam’s hands once more, unfastening the bindings at her ankles and then her wrists. Unable to hold herself up, she slumped to the ground, but Sam was there to quickly gather her in his arms.

Holding her bridal style, he carried her to the black leather bed, laying her gently upon its surface. Hovering over her, he brushed the hair back from her face, looking down at her as she slowly came back to her senses.

“How do you feel?” Sam asked, his tone and demeanor gentle and caring, in stark contrast to the man that just fucked her within an inch of her life.

“Like I may never come down,” she giggled, making Sam laugh with her.

He left her to lay in the bed while he cleaned himself up and disposed of the condom. When he returned to the bed, Y/N was coming back to herself. He handed her a bottle of water which she gratefully accepted, sipping on it gingerly.

“What are you doing?” Y/N asked as Sam presented a washcloth.

“Cleaning you up,” he smiled, such a boyish grin that made her wonder how two completely different people could exist in one person.

Too tired to complain, Y/N allowed him to clean her, making her feel refreshed. Though she’d still need a shower, she already felt better. Then he carefully checked her wrists, ankles, and ass, soothing each with a balm.

“Mmm, this part might be just as good as the sex,” Y/N mused, making Sam chuckle.

“It’s important to bring you back down, make sure you’re okay and not injured,” Sam explained. Y/N nodded, appreciating his attentive aftercare.

It took her longer than usual to recover, but she supposed she’d never really had sex that intense before. Once she felt reasonably recovered, she dressed, stealing glances of Sam’s physique for her memory bank as she did.

“I hope I get to see you again,” Sam said as they stood by the door to the room. 

Sam gently held her chin in his fingers before leaning in and kissing her sweetly. 

“I hope so too,” she smiled before letting herself from the room.

Chapter Text

Y/N was excited to be back at the Den. Her experience with Sam had left her satisfied, and a bit sore, for a while. She loved it. She wasn’t sure how, but everyone here seemed to know exactly what she needed every time.

However, this time there seemed to be a delay and she was directed to the bar to enjoy a drink or two while she waited to speak with Crowley.

“Hi, I’m Garth,” Y/N smiled at the bartender, a thin and goofy looking man that she wouldn’t have expected to see in a brothel, “Crowley’s a bit tied up at the moment. Can I offer you a drink while you wait?”

“Yes, Sir, thank you,” she responded, being polite and nervous and not having talked to him before, “So do you also see clients?” she curiously asked.

“I just tend the bar,” he smiled and she found it infectious, “But, if I may,” he added, leaning his elbows on the bar to share a secret, “I think I might have just the man for you.”

“Oh?” she was truly intrigued, sipping on her drink.

“Give me a minute,” he smiled, standing back up and knocking on the bar top before disappearing somewhere into the club.

She continued to sip on her drink, feeling a little down and wondering if she was not going to be able to be seen tonight. She was pulled from her reverie by a deep, charming voice beside her.

Turning her head she caught eyes of a gorgeous man. He was older than the others, but still stunningly handsome. He sported short salt and pepper hair and a matching beard. But his eyes and smile took her breath away.

“Is this seat open?” he asked and Y/N nodded dumbly, before shaking herself from her stupor, “Yes, Sir, please,” she offered the chair beside her.

His smile grew wider at her response. As he took his seat, his eyes roamed over her and hers over him. It didn’t take him long to have her swooning, his charm oozing from him effortlessly and sweeping her into his clutches.

“I’m John,” he introduced with an extended hand, Y/N shaking it in return as she gave her name, "Are you waiting to see someone in particular tonight?“

"No,” she admitted with a shake of her head, finishing off her drink and seeing Garth suddenly back at the other end of the bar, “I’m not sure if I’ll be seen tonight.”

“Well, I wonder if you’d allow me to be that lucky man this evening?”

“Yes, Sir,” she teased after a long pause, feeling like he could totally boss her around and just look great while doing it.

The brilliant smile he gave her made her feel like she was the lucky one.

John led Y/N down the familiar hallway of doors, stopping in front of one she had not been in before. He smiled at her before opening the door, allowing her to enter, and shutting it behind them as he followed.

She was surprised. This room looked more like a luxurious office, with a large wooden desk and leather armchairs. Though the desk and room were devoid of actual office supplies.

As she turned to face John, he was already right there smiling at her.

“Are you feeling playful, Y/N?” he asked, his gaze alone intense and commanding.

“Yes, Sir,” she smirked.

John hummed in approval, stepping around her to the desk and leaning against its edge. Crossing his arms, he chewed on his lip and eyed her up and down before flashing a toothy grin.

“Let’s see how much of a good girl you can be,” said John.

Y/N dropped to her knees slowly, arching forward to place her hands on the floor. Keeping her gaze trained on him, she began a slow and sensual crawl towards where he stood.

She wasn’t entirely sure what came over her. But suddenly she wanted to be the best girl for him. As she reached his feet, she sat back on her heels, looking up at him as she bit her lower lip.

“Stand up,” he commanded, though his tone was gentle.

She rose to her feet, still holding his gaze. John hummed approvingly, his thumb running over her chin as he licked his lips.

“You want to be my good girl, don’t you?”

“Yes, Sir,” she breathed out wantonly.

John smirked, before spinning her around and gently bending her over the edge of the desk. He gripped the hem of her pencil skirt, shifting the tight material higher and higher until her panty-clothed ass was bared to him.

John hummed once more, his fingers running over the white lace thong and garters that accentuated her pert ass. He drug an open palm down the back of her thigh before applying light pressure to scratch back up her leg, squeezing her ass at the end.

She moaned out obscenely, and he’d only just started with her.

He continued running his hands and nails over her exposed flesh, offering a light smack here and there. It didn’t hurt, didn’t even leave a mark, but the playful sensuality of it had her smiling.

“Do you like that?”

Y/N nodded as she bit her lip, her hips squirming into his hypnotic touch. Another smack sounded as he spoke against the shell of her ear.

“What does that nod mean? Need you to use your words.”

She moaned with the next smack and smiled, “Yes, Sir.”

His fingers teased over her covered folds and along the crack of her ass, before teasing over her cheeks and thighs once more.

Before long he had removed all but her thong, garters, and stockings, but he was still fully clothed.

He had her standing, held against his chest as he kissed her. One hand gently resting around her throat, the other trailed down her body and slipped beneath the lacey thong, finding her wet folds.

He continued kissing her deeply as he toyed at her clit and entrance, gathering her wetness and spreading it around. She could feel his growing arousal and pressed back against it.

John growled, turning her to face him as he kissed her once more. His hand found its way back to her folds, a single finger rubbing expertly at her clit. She focused on unbuttoning and removing his shirt as he continued to drive her wild.

“Do you wanna cum?” he breathed against her lips. She trembled in his arms, both from his tone and her need.

“Yes, Sir,” she managed to huff out a breath, gasping as he rubbed harder.

“Mmm, such a good girl. Go ahead, come for me, pretty girl.”

Her body followed his command, a small but pleasant orgasm tingling through her, but she was ready for so much more. She pouted as he removed his hand to take off his shirt, tossing it to the side as he began to work on unfastening his pants.

Without hesitation, Y/N dropped to her knees, pushing his hands aside and taking over. John smirked down at her, her eagerness making him chuckle.

When he sprang free, she smiled. Not a single man at the Den had disappointed her yet and John was just as thick and beautiful as the others. She leaned forward, sucking the tip into her mouth before she added a hand and began gently working him over.

John’s hand smoothed into her hair, brushing it back and petting her as she pleased him. After a few moments, he stopped her.

“Would you let me fuck your mouth?”

“Yes, Sir,” she moaned, her pussy throbbing with her complete arousal.

Seeing his cock twitch at her words, she realized he liked ‘Sir’ as much as she did, which only made the whole thing that much hotter for her.

She leaned forward, taking just the tip in her mouth, and relaxed as she looked up to John and waited. He threaded his fingers through her hair, gently tugging her back and forth as he moved his hips to begin a slow and easy rhythm.

Before long, drool was spilling out the corners of her mouth, a small choking sound coming forth with each thrust in and out of her throat. He had to make himself stop before he came, pulling her off of him and back to his mouth so he could devour her.

Without notice he picked her up, her legs wrapping around his waist with a surprised squeal. He carried her to the desk, laying her back on its surface. He stepped away for only a moment, grabbing a condom and sheathing his length.

Y/N smiled and spread her legs as he returned to her, having removed only the thong and leaving the garters in place. Holding one leg against his shoulder, the other spread wide to the side, he slid inside. She moaned and wriggled against him, trying to get him to do deeper. He laughed at her petulance, only letting half of his length penetrate her before slowly pulling out and teasing to the same depth.

“Please, Sir, please,” Y/N begged, finding very little leverage to move with the form and steady hold John had on her.

At her words, he suddenly thrust fully within her, making her moan loudly. The more she moaned, the faster he moved, ensuring he gave her all of him on each pass. Wrapping one arm behind her neck, the other still holding her leg, he had her nearly bent in half towards him, using his grip as leverage as he thrust harder and deeper.

Her orgasm was sudden, her walls clenched so tight that it pushed John out of her. With a grunt, he pulled her from the table, turning her to bend her over its surface. Lifting one of her bent legs onto the desk, he opened her up wide before slamming home once more.

She screamed as the action lurched her forward. John set a harsh pace, his hands holding her firmly. She tried to grip onto the table, finding only flat surface gliding beneath her fingers. One hand found the back of her neck once more, holding her firmly in place as he pounded them both to orgasm, her third of the night.

As he pulled out, she remained bent over the desk, her legs shaking and trying to calm her erratic heart and breathing. At this point, she knew he’d be there to care for her, as they all had, and it might have been her favorite part of the whole experience, every time.

She felt the warm cloth that cleaned and soothed her, John’s hands delicate and caring. When she stood up, she felt his arms around her, lifting her from the ground and carrying her.

John sat back in the large desk armchair, draping Y/N across his lap, her legs dangling over one of the arms. She curled into his chest as she calmed, his hands rubbing over her soothingly as she came back down.

“You okay?” he brushed the hair back from her face as she met his eyes with a sleepy grin.

“Yes, Sir,” she chuckled, John joining her.

Chapter Text

Y/N let out a long and happy sigh, then tension eased from her shoulders as soon as the club came into view. Thanking the driver, she exited the vehicle, the doormen smiling wide and greeting her by name as she passed through the familiar doors.

She didn’t have an appointment this time, but as a regular client, she didn’t need one just to come to the club. 

“Hey, Garth!” she greeted the quirky but loveable bartender.

“Ms. Y/L/N,” he returned with a bright smile, “The usual?”

“Please,” she nodded, accepting the drink with a smile as he went to serve others.

She leaned against the bar, her eyes roaming the lounge of the club. It was busy tonight, people all over having a grand time. Sipping her drink she let the alcohol relax her.

Work had been rough lately. Though she was given the promotion she had been vying for, it was only after her predecessor fucked up royally and lost them the deal. A deal she put a shit ton of work into and thought was in the bag. The stress of the deal and the increased workload had her nerves frayed. She needed the comfort of the club, where she could relax and not think about work. Not think about anything.

She’d never spent much time in the lounge, mostly just coming to fulfill her needs and head back home. Polishing off her drink she turned back to the bar, finding Garth already ready with a refill. New drink in hand, she decided to walk around and explore, possibly mingle.

As she stood watching several couples making out in the comfortable chairs and sofa, she was caught off guard by a pair of hands sliding around her hips and pulling her back into a firm body.

“Glad to see you again,” the deep voice rumbled into her ears, making her smile brightly as she turned to face the source.

“Well, Hello, Sir,” she purred, John grinning with his approval.

“Please tell me you’re here to see me, Doll?” he asked and she couldn’t help but swoon under his attentions.

“There’s no way in Hell you’re getting seconds with her before I do.”

Y/N chuckled, knowing that voice without having to see him. She gently removed herself from John’s hold, turning to see Sam smirking devilishly at her. He pulled her into his arms, the heat of his body igniting a fire in her belly.

“There’s still so much I wanna do to you,” Sam growled out low and Y/N couldn’t stop the moan that spilled from her lips.

Sam’s gaze, his touch, and his voice sent chills through her, his hands splayed across her back and hips. It was hypnotic and she was about three seconds away from letting him do whatever he wanted with her.

“Who’s your friend?” she heard an unfamiliar but deliciously deep voice that managed to break her from the spell Sam had cast upon her.

Sam groaned and rolled his eyes, releasing his hold on Y/N, leaving her bereft of his touch and warmth. But her disappointment didn’t last long as she laid eyes upon one of the most stunning men she’d ever seen.

“Y/N, this is Dean. Dean, Y/N,” Sam introduced, he and John watching as Dean smirked. He took her hand, kissing the back of it as he repeated her name, “My brother.”

That got her attention, making her glance wide-eyed between the two of them. Brothers. Her mind began conjuring the most sinful of thoughts involving the both of them and she visibly flushed.

Dean chuckled, clearly amused with how affected she was.

“So when do I get some time with the lovely lady?” he asked her and Y/N could already feel herself getting wet. 

“Whenever you want,” she breathed out, the men chuckling around her once more.

Dean grinned triumphantly, “I’ll book you an appointment,” he promised, kissing her hand once more before excusing himself.

She was really looking forward to that.

“Excuse me, Gentleman,” Crowley suddenly appeared, Y/N loving his suit choice this week. He seemed to have many of them, all of them tailor-fitted, and all of them making her desperate to see what lies beneath, “I’m afraid I need to steal the lady away.”

Sam and John both groaned but relented, each reminding her that they couldn’t wait to have her again. Crowley’s hands wrapped around her from behind, turning her and guiding her to walk with him as he left one arm around her hips.

“I wasn’t expecting to see you today,” Crowley spoke with a small smile, “But I’m glad you’re here. I have a gift for you.”

“A gift?” Y/N was surprised but immensely curious.

He pulled her to a stop at the base of the grand staircase that lead to the hall of rooms. A man stood there with a quirky grin and blond locks, an air of absolute menace about him that only served to entice her further.

“This is Gabriel,” Crowley introduced, Y/N extending her hand and receiving the usual kiss on the back of it. She really liked that part.

“Nice to meet you, Y/N,” he spoke, pulling her gently from Crowley’s arms, keeping ahold of her hand. She cast a glance over her shoulder at Crowley who merely nodded and smiled. Turning back to Gabriel, she allowed him to lead her up the staircase and to one of the many rooms.

Gabriel shut the door behind them, walking over to a small bar set up in the corner of the room. Y/N slowly wandered around the room, taking in all the details. Faux fur-covered seating, a golden shimmering pole, and a small black leather bed. But it was the small, black, saddle-like machine sat in the center of the room that made her swallow hard and clench her thighs.

Gabriel returned with a drink, ushering her to sit with him. She smiled gratefully, sipping at the offered drink, her gaze continuously drifting to the machine. 

“You ever tried one?” Gabriel asked with a smirk as he removed the plastic cover from a lollipop and slid the treat between his lips.

“No,” she admitted, flushing at the thought. She had heard of machines like this one, but she’d never tried it.

Gabriel leaned forward with a wicked grin as he removed the lollipop from his mouth, “Would you like to?”

Y/N glanced between him and the machine. She was nervous, more so than she had been with the others. 

“Okay,” she agreed with a grin, setting her glass aside.

She stood, keeping her eyes trained on him as she slowly removed her clothing. Gabriel sat back, the white stick of the confection sticking out of his grinning mouth as his eyes consumed her revealed flesh.

“Hmm,” he hummed as he stood, “I can see why everyone likes you so much.”

She swooned under his compliment, Gabriel clearly satisfied with himself. He took her by the hand and led her to the machine, assisting her to straddle the contraption. She was already wet and ready, just being in the club signaling to her body to prepare.

As she sank onto the machine, the attached dildo slid easily into her core. She settled on it with a sigh, adjusting her hips. Gabriel pulled up a chair to sit in front of her, crossing his legs as he sat, before holding up a small remote in his hand and waving it at her.

“Relax,” he insisted, “We’ll start slow, okay?”

Y/N nodded, her eyes locked on his. Even though she watched him hit a button, she was still surprised by the vibrations that began gently coursing through her core. A gasp gave way to a moan as the vibrations slowly tantalized her.

As she relaxed into it, Gabriel hit another button, the dildo attachment now slowly moving in and out of her. When he increased the speed, an orgasm ripped out of her unexpectedly, making her laugh as it subsided. Gabriel smiled along with her, enjoying seeing her relax and come undone. But he didn’t stop, instead increasing the speed of the vibrations and thrusts gradually.

Before long, she was writhing on the machine as it pummeled her pussy relentlessly. Her legs shook, her grip tight on the machine. She chanced a glance at Gabriel, that damn stick still sticking out between his ever-grinning mouth.

He seemed to be able to read her very well, changing the speeds to drag out her experience and tease her to highs once again. 

“You’re so fucking hot,” Gabriel commented, standing from his chair and brushing along her cheek and jaw with one hand. His eyes drifted down to her stuffed pussy, the black leather of the machine glistening from the wetness that drenched its surface.

He removed the candy from his mouth, the lollipop half gone already. He lowered it to her parted lips, running the sugary treat along them, allowing her to suck it into her mouth briefly before returning it to his own.

He held her on the edge, Y/N beginning to grind against the machine, desperately seeking another orgasm that was just out of reach. 

“Please,” she panted, feeling like she might burst or scream, the continued orgasms leaving her overstimulated. 

“Mmmm, one more for me, Pretty Girl?” he asked and she nodded, her eyes fluttering closed as he increased the speed to maximum levels.

Y/N did scream then, the intense pleasure and pounding sending her into an orgasm that shook her whole being. The movements slowly ebbed away until the machine was shut off. 

Y/N was so overwhelmed and exhausted that she nearly slid to the floor as she tried to climb off the machine. Gabriel was at her side in an instant, helping her to lay back on the small leather bed beside the machine.

Gabriel laid beside her, propped up on one elbow as he admired the muscle twitches and spasms still coursing through her.

“Love watching a woman come undone,” he confessed.

Y/N turned her head to him, barely able to hold her eyes open, only to be met with amused but kind eyes.

“Well that was fun,” Y/N huffed a laugh, an arm thrown over her eyes as she waited for her body to calm.

“I agree,” he teased, popping the almost gone sucker from his mouth and offering it to her with a raised brow. 

She smiled, opening her mouth and allowing him to slide the treat between her lips. It actually helped to soothe her, the sugar satisfying to her palate after the intense experience. Gabriel trailed his fingertips over her chest and torso, completely avoiding her most sensitive areas, toying with the goosebumps that popped up on her skin.

“That was an awesome gift,” she huffed as she finally sat up, throwing away the now empty stick. Gabriel slid off the bed to his knees, settling between her legs and slowly laying her back with a wicked grin.

“Allow me to clean you up,” he teased before gently lapping along her thighs and folds. 

Y/N relented, her fingers running through his soft locks as he gently brought her to yet another orgasm. Though small, it shook her whole being, her body thoroughly sated and feeling like she could sleep for days. 

The tension she’d been carrying was gone from her body and the weight and stress vanished from her mind. She had to remember to thank Crowley. He always knew exactly what she needed, even if she wasn’t sure herself. She hoped she might get to thank him properly.

Chapter Text

“Ms. Y/L/N!” Crowley greeted, rising from his usual table in the club and kissing the back of her hand as he ushered her into a seat. “Always a pleasure,” he grinned from across the table.

“Mmm, so when am I going to get that date with you?” She teased, sipping from her glass and locking her eyes with his. The charming grin he flashed had her hungry for more.

“You’re very persistent,” he commented, biting his lip as he shamelessly let his eyes trail over her form. She relaxed in her seat, letting him get his fill.

“I know what I like,” she shrugged.

“As do I,” Crowley agreed, the two of them sharing a silent moment of secret smiles. The pleasant tension between them was interrupted as the young man, Kevin, came back to Crowley’s table, whispering in his ear. Crowley nodded and dismissed him, rising from his seat and offering Y/N his hand.

“Your company for the evening is ready for you,” he led her himself this time up the grand staircase and to the hall of rooms, stopping before one of the doors.

“Next weekend,” he promised, kissing the back of her hand, “You and I can get…better acquainted.”

Y/N swooned at the thought, feeling like she was on cloud nine. She felt a tinge of disappointment at his departure but remembered why she was there. Turning towards the door, she took a deep breath and entered the room.

As the door clicked softly behind her, Y/N’s breath caught in her throat at the sight of the man in the room. He was all she could see, stood tall and center, his torso bare and jeans slung low on his hips. His green eyes flashed with mischief as he bit his lip and looked her over like a predator about to devour its prey.

“Y/N,” he greeted with a devastating smile. “I’m Dean,” he reintroduced, kissing the back of her hand and standing straight once more.

“I remember,” she smirked back. Though their previous interaction had only been for seconds at best, it had certainly left an impression. She had heard the buzz over Dean - the most requested of all the men - and she knew whatever came next was going to be noteworthy.

“I’ve been waiting for this,” he admitted, stepping up to her with confidence, his hands landing on her waist. “Been waiting for you.”

“Oh?” she asked breathlessly as he turned and moved her where he wanted. She was so entranced by his mesmerizing eyes and touch that it blocked out everything else.

“Mmm,” he agreed, his lips finding her neck and kissing up to her ear where he nibbled on the lobe. “I’ve planned out a really fun time for us. Have to outdo the others, you understand." 

His words were lightly muffled against her skin but she’d heard them clearly, giggling at his playful words and loving that they all seemed to want and enjoy her. He began removing her clothes and she was swept up in his touch, in the heat and pressure of his soft lips on her skin. By the time she was naked, she was already soaked, his wandering lips and hands igniting a fire under her skin.

He gently coaxed her to sit on the end of the bed in the room, the soft sheets cool against her heated flesh. He smirked and stepped over to a table of implements, casting a glance at her over his shoulder before picking one and returning. Her eyes went wide at the object he held and her thighs clenched.

"Ever used one of these?” he asked, holding up the long metal bar with cuffs attached to the middle. She swallowed hard but clenched once more in excitement.

“No,” she admitted. “But I have been restrained." 

She thought back on her time with Sam, how nervous she was, but how pleasurable it all felt. It was different, freeing, to hand over the reins to someone, to trust them and let them have their way with you. If it were just a normal guy, she’d probably never consent to such a thing. But being in the club, with these men, gave her a sense of safety to explore herself and her pleasures.

He leaned down to whisper in her ear, his breath causing a few hairs to tickle against her skin, "Would you let me restrain you? Have my way with you?”

Her whole body shivered at his words, a deep moan tearing from her throat and Dean chuckled.

“Yes,” she breathily responded, making him chuckle once more.

“Safeword?”

“Colors?” she shrugged and he nodded.

He set the bar beside her on the bed before cupping her face and kissing her soundly. His lips were Heaven, the perfect softness and give as he kissed her deep and with hunger. She could tell he wanted this as much as she did.

His kisses consumed her and he used the momentum to guide her to lay back on the bed. Only then did he break the kiss, but only to trail those perfect lips down her throat and chest. By the time he made it between her legs, she was already squirming with desire.

When he removed himself from her, an involuntary whine left her throat. He chuckled again, and it was both beautiful and infuriating in the best of ways. 

“Ready?” he asked, holding the bar in his hand. 

“Yes.”

Dean moved her onto her hands and knees, his touch gentle and guiding. He positioned her legs apart enough to strap each ankle into the ends of the bar. Once secured, she tested the bindings, finding that her legs couldn’t move at all, the bar holding her wide open and exposed. 

“Good?” he checked in with her and she agreed, giving a ‘green’ with a smile. “Now your hands,” he insisted, helping her guide her hands between her legs to be bound with the cuffs in the center of the bar.

Once complete, he took a step back, admiring his work. Y/N could see nothing, her body not able to move much at all. Her cheek lay against the bed, her ass high in the air, but she didn’t feel panicked. If anything, she felt a little embarrassed at being so utterly exposed.

“You look so fucking hot right now,” Dean growled out and her thighs attempted to clench at the sound, to no avail. “All tied up for me…Fuck, I bet you’d look great in rope.”

His labored breaths let her know just how into it he was and it made her want to please him even more. She’d never been tied in rope herself, but she had seen a few videos on the topic. With the way Dean was talking, the way he sounded, she’d do literally anything he wanted.

She felt him shift on the bed behind her, his weight sinking the mattress a little between her legs. When his warm hands landed on her ass, she moaned, the firm massage he gave her cheeks introducing her to his touch. He moved one hand, teasing his finger along her rim and down through her aching and dripping pussy.

She bucked at the touch and Dean hummed at the wetness he found there. He continued teasing her, his finger running through her lips but not touching any of her most sensitive areas. He gently flicked her clit and she jumped at the sudden sensation, making him laugh before he slid a single digit deep into her core.

They moaned in tandem at the feel, Dean slowly working and feeling her inside, watching as her hips began to buck and bounce. He added a second, her pussy stretching to accommodate him. She moaned louder, trying to buck harder for more pressure, more speed, just more. But Dean was insistent on taking his time, teasing her.

“Dean!” Y/N whined, trying to buck against him. He slowly removed his fingers, her whine coming forth again.

“Color,” he demanded, hands soothing over her ass.

“Wha- green,” she swallowed, wriggling her hips. “Please…”

He chuckled, leaning forward and blowing a stream of air from her asshole down over her wet folds and to her clit. Hands planted on her cheeks, he repeated the same path, this time with his tongue, firm and slow against her, licking up her slick in its wake.

He pulled back, humming and licking his lips, before diving in once more. His grip tightened on her ass, holding her open as he circled his tongue around her clit, then drove deep into her, gathering her slick from the source.

Words escaped her completely as Dean set in, the sounds of his slurping and smacking lips enhancing the feel of his warm, wet tongue devouring her. She’d never had someone eat her out so enthusiastically and he was skilled. 

Just as she felt a climax cresting, her hands clamped around the bar between her legs in anticipation, he pulled away. Her breath punched from her, feeling incredible and bereft all at once. 

“You taste so damn good, Y/N,” Dean spoke with a deep, gravelly tone. 

He leaned over her from behind, kissing along her lower back to her ass and nipping at the plump flesh. She bucked and squirmed, that damn amused chuckle reaching her ears.

“Please, please,” she shamelessly begged, her core throbbing and dripping.

“Mmm, you beg so pretty, Babygirl." 

A heartbeat later she was rewarded with Dean’s cock breaching her entrance, her body so very eager and ready for him. She had no idea when he’d managed to get undressed and don a condom, but she didn’t care. She was panting, the sudden fullness of him making her elated and overwhelmed all at once. He was large and long, filling her completely and in this position, she felt like he was splitting her open, and it was fucking perfect.

"Relax,” he urged, kissing along her shoulders and biting down a little, making her gasp and buck. He sat back up, hands on her hips, pulling back slowly, he slammed back home, making her scream out. Instantly setting a brutal pace, he fucked her hard, her body having nowhere to go, held in place to take him again and again.

Her eyes rolled back in her head as her first orgasm washed over her, mouth hung open in a silent scream. When she could draw a breath, it was deep, immediately released in a pleasured scream, her body shaking with the intensity of it.

But he didn’t stop.

If anything, he got faster.

He shifted his hips, his grip tightening. The growls he gave with each thrust were one of the most erotic sounds she’d ever heard. Another thrust and he hit her g-spot, making her cry out, squeezing her eyes shut as she came hard a second time.

“Fuck, you feel so. good.” Dean moaned, leaning over her to adjust his angle once more, still pounding away with no end in sight. She careened into another orgasm or continued from the last, the pleasure mixed with pain making her body sing. 

Her throat was raw and dry, her body spasming but she couldn’t get enough, and apparently, neither could he. The whole mood shifted when a sudden aching cramp took hold of her thigh, making her scream out in a way that immediately caught Dean’s attention. He slowed his pace and it was enough for her to catch her breath and call out.

“R-red,” she uttered, in pain and feeling terrible at having to stop, but the cramp in her leg wouldn’t relent, clenching the muscle hard and painfully. 

Dean worked fast and in a second, had her hands and ankles released, flipping her to her back to check on her. He leaned over her, cupping her face, the look of concern there would’ve melted her heart. But her hands immediately went to her thigh, clutching it tightly.

“Cramp,” she complained through clenched teeth.

Dean didn’t hesitate, his eyes following her hands and moving them out of the way as he gently massaged the muscles in her leg, up and down, easing the cramp and tension. His strong fingers worked at the muscle, digging just right and rubbing with his palm to work away the pain. His fingers were slightly calloused and she wondered how he had a working man’s hands in this profession. But they felt perfect, relaxing her, taking away the pain, and reigniting her desire all at once as she relaxed back into the bed with a content sigh.

“Thank you,” she rasped and Dean jumped from the bed, fetching a bottle of water and laying on the bed beside her as he helped her sit up and drink it. She smiled meekly at him as she sipped, handing it back to him and laying back against the sheets.

“Are you alright?” he asked, that sweet look still on his face, his eyes bright and shining with worry. She absolutely understood why he was a favorite.

“I’m fine,” she nodded, “I’m sorry-”

“No, you have nothing to be sorry about. If anything, I’m sorry I pushed you that far.”

“You didn’t,” she laughed and he perked up at the sound. “It was just a cramp. It was pretty intense,” she laughed, the euphoric feeling washing over her again. “Maybe we could go again, except I can see you this time?”

A grin broke out on his face as he climbed over her, settling between her legs, “Now, that I can do.”

Dean moved his arm under one of her legs, his hand splayed on her lower back as he tilted her hips. He slid inside with a groan, her core drenched and walls quaking upon his reentrance.

She was so grateful she got to see him. Especially like this. His mouth hung open, his eyes fluttering, cheeks reddened and she could tell he was enjoying her as much as she was enjoying him, which only made it that much hotter.

Her hands roamed up his arms and stopped on his muscular shoulders. She smiled coyly at him, pursing her lips as she locked eyes with his stunning emerald orbs. 

“Fuck me, Dean.”

He gave a crooked smirk before plunging deep and hard, working himself up to a steady pace, though it was less intense than before. She clung on for dear life as he drove them both higher, his hips slapping hard against hers, his hand holding her hips in place. Her eyes devoured his body, the muscle movements, the sheen of sweat, his plump lips that got redder from biting as he tried to hold himself back. 

The fact that he was working so hard to retain and control his own pleasure in wake of hers was even more erotic, shooting her ever closer to her climax as she clung to him desperately.

“I’m gonna cum,” she moaned out, locking eyes with him once more. He nodded, shifting his hips and finding her g-spot once more, driving fast and hard to get her over that edge.

She went with stars in her eyes, her head thrown back, allowing the loud moans of pleasure to escape as she screamed her release to the sky. Dean pumped a few more times, his head dropping to the crook of her neck as he held her tight and came with a muffled cry. It was intense enough that she could feel it even though the condom, the spurts of it jolted her body, his cock throbbing against her rippling walls.

“I can see why you’re everyone’s favorite,” Dean smirked as he removed himself, tossing the condom away and dropping onto the bed beside her with a dramatic sigh. She turned to look at him with a giggle, him smiling in return, and she loved the easy and casual feel of it all.

“Well, I could say the same. And you're definitely worth the wait,” she countered, Dean beaming as he leaned in to cup her face and kiss her sweetly, sharing in the post-coital bliss. It would probably take a while for the two of them to come down. As he kissed her breathless, she suddenly wondered if she could book him just a little bit longer.

Chapter Text

It had been weeks since Y/N had last been at The Lion’s Den. She was supposed to finally have her chance with Crowley, the delicious tease that he was. However, duty called, and work needed her time and attention. Crowley was more than understanding, as she expected he would be, and rescheduled her for a private session. Though, she had to admit, after their phone call it felt more like a pending date and she wasn’t so upset about that.

Now that she finally had the time to return to the Den, eager to satiate her desires, Crowley was away on his own business. Most likely expanding his empire seeing as The Den was doing so well. While she was pouty that she would have to wait a little longer for a peek beneath those tailored suits, she knew the club had plenty to offer to fulfill her needs and hold her interests.

Greeting Garth at the bar, she ordered a drink, settling in on a stool and surveying the room. The men she was familiar with were not around, but there were plenty of others for her to feast her eyes on. She wasn’t sure what she was looking for or even what she was in the mood for, suddenly missing Crowley’s intuition all the more.

Until she saw him.

Tall, chiseled jaw, looking like a living, breathing marble statue as he glided through the room. She bit her lip as his eyes locked with hers across the room, a sinister smirk tugging at his lips as he made his way over.

Y/N turned back to the bar, taking a sip of her drink, smirking when she felt his presence. She turned her head towards him with a smile as he took the stool beside her.

“You are Y/N, right?” he spoke, his voice sounding so strong, his words spoken with precision. “Crowley and others have spoken highly of you.”

“Glad to know I’m a favored client,” she chuckled.

“More than that, maybe,” he said but continued before she could question. “I’m Gadreel.”

He accepted her hand, kissing the back of it, to which she was now accustomed. Though it still made her heart flutter the same every time, the simple sweetness of it took her breath away.

“Are you spoken for this evening?”

“Not yet,” she grinned, loving his charm. “But I’m wondering if you’re available?”

“It’d be my absolute pleasure,” he responded, his voice deeper as he helped her off the stool.

She was giddy as she allowed Gadreel to guide her up the familiar staircase to the hall of rooms. She wondered what this large and solid man with an air of mystery had in store.

As soon as the door closed behind them, she pounced, her desire ramped up after weeks without. Wrapping her arms around his neck she kissed him hard, pressing herself against him. He responded eagerly, letting her take what she needed from him.

Clothes were stripped and strewn carelessly, Y/N’s need driving her into a frenzy. It didn’t hurt that he seemed to ooze absolute want for her. As his body was revealed to her, her eyes widened, taking in the taut skin and muscled physique. Was every man at The Den a chiseled God? She pressed herself against him once more, moaning into his mouth at the feel of his firm body against her own.

With little effort he hoisted her up onto his hips, kissing her breathlessly as he moved. When the kiss broke she realized he was sitting in a chair and she was straddling him. She moaned, her hands running over his chest and abs as she ground against him.

His kisses alone completely distracted her, his lips and tongue tasting and consuming her, stealing her breath away. She gasped as she felt his hand reach her eager core, his fingertips teasing lightly against her dampened folds.

Y/N ground her hips against his hand, silently urging him to touch her how and where she needed. She could feel the smirk against her lips as he found her clit and teasingly rubbed small circles against it.

“You’re a tease,” she whined against his mouth, gasping once more as he slid a finger deep into her core.

“Mmm, and you’re needy,” he responded against her flesh as his lips wandered along her neck and collarbone.

“Please,” she begged, not caring how desperate she sounded.

It had been far too long for her liking since she’d been with anyone and the attentions she received at The Den only left her craving more and more. Now that she found and frequented this place, she wasn’t sure she could do without it.

And really, why would she want to?

Sliding two fingers within her core he instantly found her most sensitive spot, making her choke on a breath. He held his fingers firm against her spot, barely moving them, creating intense pressure and desperation. Her hips began grinding against him of their own accord, seeking much-needed friction.

Gadreel chuckled as he studied her intensely, catching her off guard by suddenly fucking her swiftly with his fingers, unrelenting on her g-spot.

“You’re so responsive,” he groaned, never missing a beat in his ministrations, adding his thumb to her clit to make her gasp and squirm harder. “No wonder everyone enjoys you so much. The perfect playmate,” he moaned as her juices dripped down his wrist.

The teasing was too much, holding her on edge but keeping her just out of reach of her climax. She wanted him just as desperate as he made her. Slowing her grinding, she slid a hand down his torso to his throbbing length, grinning as she took him in hand and he groaned.

“You’re pretty responsive yourself,” she teased back. His responding snarl made her wetter than his fingers had.

Producing a condom from seemingly nowhere, he continued to devour her mouth as he slid it on with practiced ease. He smirked, an arm wrapped around her waist, his muscles bunching beneath her fingers as he hoisted her just enough to slowly lower her down onto him. Her mouth hung open as she slid down his length, her ass settling against his thighs.

“Go on then,” Gadreel teased, nipping at her ear lobe, his grip still tight around her. “Ride me.”

He emphasized his point by thrusting his hips upwards. Y/N groaned, starting a gentle rock as she lifted herself and dropped back down onto him, gasping as each stroke hit her deep. She tried to move faster, but his grip on her was unyeilding, controlling her movements and driving her mad.

She quickly realized that just because she was on top, didn’t mean she was in control. The thought had her clenching around him, drawing a deep moan from his throat. One of his hands rested on her lower back, the other over her collarbone. His hand drifted towards her neck, his fingers wrapping ever-so-lightly.

Her breath hitched and her hips stuttered at the implication.

“Have you ever tried breath play?” Gadreel asked, his hot breath fanning over her ear as he slowly thrust upwards into her heat.

“No,” she responded in a breathy moan. The thought excited her. Everything she had tried so far had been amazing, she wasn’t about to stop now.

“Mmm, I think you’d really like it,” he explained, thrusting harder. “I know Crowley loves it, both on him and others.”

Well, she really wanted to please Crowley when she finally got the chance to be with him.

“Okay,” she agreed with a nod, holding his gaze so he knew she meant it.

He increased his pace, bouncing her on his lap, his grip around her throat tightening with his pace. She could feel the air being cut off making her lightheaded, but the pounding of his thick cock into her pussy was amplified, building into a crescendo. Her heartbeat throbbed in her temples and the walls of her pussy. It felt like a race: would she cum first, or die?

He released his grip and she took in a deep breath, her orgasm crashing into her as she did. The intensity of it had her wrapping herself around Gadreel, desperately clinging to him as if she might fly off somewhere if she wasn’t grounded. Her whole body trembled, her walls convulsing and throbbing desperately against his thick and unyielding length.

“So beautiful when you cum,” Gadreel whispered reverently, his hips working a steady rhythm as she ground against him, working through her high and building back up once more.

He took her hand, guiding it to wrap around his own throat, “Try it on me,” he insisted with an encouraging nod.

She nodded in return, moving her hips and riding him harder as she began to squeeze.

She could see the change on his face, the same as she felt it happening to her, as he grew close. She released her grip and Gadreel shouted, holding her hips tightly as he fucked them both through their final orgasms.

“Oh my God,” she chuckled, her body still twitching and spasming from the intense encounter.

“You okay?” he asked, his hands running soothingly over her body, helping to ease and soothe her muscles.

“Yeah,” she nodded, climbing from his lap now she felt more stable. “That was…incredible,” she admitted.

He lowered his gaze bashfully, a light blush adorning his skin, “Thank you for allowing me to be your date tonight, to share something new with you.”

As she headed home, she thought over the different men she had spent time with and the various things they had opened her up to experience. She was eager to take her new knowledge and apply it to Crowley when she got the chance.

Chapter Text

Y/N took a deep breath to calm her nerves as she exited her hired car, the all-too-familiar door of The Lion’s Den glowing brightly, beckoning her within. She pulled the gold-embossed invitation card from her clutch, handing it to the doorman who smiled warmly and opened the door for her to enter.

The Den was buzzing with life and activity like a nightclub - music blasting, drinks everywhere. All the staff and the most elite of clientele were invited, closed to all others. It was a private celebration of the anniversary of the club’s opening. The sounds of laughter and joviality rang through the ever-sex-tainted air.

Grabbing a champagne flute off a passing waiter’s tray, she began to walk the room, letting her eyes take in the abundance of sensations around her.

As she surveyed the party-goers, her eyes paused as she caught each man that she’s enjoyed separately, each surrounded by clients, both favored and prospective. Playing coy and unaffected - and truly just anticipating her time with Crowley - she passed by each of them, their eyes findings hers and giving her a sultry look that made her reminisce of her times with them.

Before long, Crowley’s young assistant, Kevin, found her amongst the crowd, inviting her to follow him to his boss’ private table.

“Crowley’s been waiting for you,” Kevin told her as he effortlessly maneuvered through the crowds and to the familiar, secluded booth Crowley liked to occupy.

She was eager and excited but tried her best to hide it. She’d learned to hone her poker face over years of business meetings and negotiations. The Den was one place she felt she could let her guard down and relax.

“There she is,” Crowley greeted as she approached his private booth. He stood beside the alcove, straightening his suit and eyes raking her body, draped in a simple gown for the evening’s events.

“Crowley,” Y/N responded with a smirk, offering her hand. Crowley grasped it gently between both of his hands, bending down to kiss the back of her knuckles.

“Thank you for accepting my invitation,” he gestured to the booth and Y/N slid into the seat, Crowley sitting opposite of her.

“I was wondering if I was ever going to get this one-on-one with you or if you were going to keep teasing me,” she pouted playfully.

“Ah, yes,” Crowley sighed, nodding his head. “I’ve been rather busy lately,” he explained. “Expanding my empire, you understand.”

“I do,” she agreed quickly. “And I’ve heard of your successes. Opening a new club?”

“Yes, and I heard of your latest conquering as well. You’ve been all over the papers recently. I have to admit, I’m a fan of your work.”

Silence fell between them as fresh drinks were delivered. Y/N took a long sip, her eyes trailing over Crowley in yet another perfectly tailored suit.

“How have you been enjoying the club?” Crowley inquired, easing the momentary lull in their conversation.

“You should be able to tell from my monthly bill how much I enjoy this club of yours,” she smirked behind her glass, feeling mildly tipsy and relaxed in Crowley’s presence.

He chuckled, “Yes, well, what if I told you that I’d like to make a deal with you,” he challenged, a glint in his eyes.

Y/N sat up straighter, gently setting her drink on the table. She eyed him carefully, as anyone would a potential opponent. Her eyes sparkled and her heart raced, ready to broker another deal. After all, it’s what she lived for. With a silent gesture of her hand, she urged him to continue.

Enjoying the game as much as Y/N did, Crowley prepared to lay out his offer.

“You can have me tonight, however you want, as a client. I am more than willing.”

Y/N’s heart raced differently, Crowley’s proposal cutting to the chase of what she’d been after since she laid eyes on him. Biting her lip, she was eagerly anticipating the rest of his proposal.

“Or, you can agree to be mine and I’ll fuck you for free, whenever you want.”

“Be yours?” she inquired with a quirked brow, more than intrigued by his proposal.

“I’m a King without a Queen,” he sighed. “You are smart, beautiful, cunning. Together we could expand my empire and be unstoppable. And of course, you can continue to sample the wares, so long as you remain mine.”

“Think it over. In the meantime, I believe we have much more pressing matters,” his smile morphed into a grin as his eyes shamelessly trailed over her body.

More pressing matters indeed.

She would definitely think over his offer, though she was sure what she’d most likely say.

Welcoming the distraction, and far too eager for this long-awaited encounter, Y/N allowed Crowley to lead her by the hand away from the staircase and familiar hall of rooms and into a long hallway that led to somewhere much more private.

It was his office, she quickly realized, and it was single-handedly the most expensive and lavish room she had seen in this entire place so far. The soft click of the door behind her made her smile, her anticipation ramping up, her panties already growing damp.

“I enjoy rare and beautiful things,” Crowley spoke as he walked comfortably across the office, unbuttoning his suit jacket and casually leaning against the edge of his desk.

She glanced around the room, indeed eyeing many things that piqued her interest. Her eyes floated back to him. The electricity in the air between them crackled with heat, the delicious banter and teasing drawing out, being savored between them.

“And you are the most rare and beautiful thing I’ve ever encountered,” he breathed out. She felt her body slump and swoon, the seriousness flickering in his eyes making her desperately ravenous.

She wasn’t one for relationships, her career at the forefront of her mind, the Den a way for her to feed her needs and desires without the complexities of relationships. The look in his eyes made her realize they might be dancing on a line here, but it also made her want to take a chance and step right over it.

Meeting his eyes once more, she knew her fate was sealed.

“You want to be mine?” Crowley asked as he leaned back against his desk with a knowing smirk. “Show me, My Pet.”

A flutter ran through her body as she was more than eager to comply. She knew he wanted her as much as she wanted him. Holding his gaze, she slipped off her dress, revealing she was completely bare beneath. His eyes roamed over her body with admiration and lust.

“Stunningly beautiful, Y/N,” Crowley praised. Standing straight, he raised a single finger urging her to come forth.

She gave a crooked smirk as she slowly dropped to her knees, her hands hitting the ground next. She curved her back like a cat as she slowly crawled towards him, the way that John appreciated. As Crowley rubbed his hand against his strained and hardened cock, Y/N knew he too appreciated her moves.

As she reached Crowley, Y/N used her hands to crawl up his thighs, straightening her naked body against his legs. She ghosted along his covered shaft with her nose, her hands settled on his hips.

“My, you are a good pet, aren’t you Love?”

Tilting her head back she met his eyes, his hand cupping her cheek.

“Yes, Sir,” she responded, doing her best to maintain doe-eyes and a straight face.

Crowley growled before leaning down to crash his lips into hers. Pulling back he whipped off his jacket, the matching vest underneath following closely behind. His hands tucked under her arms - with a strength she didn’t know he possessed - he lifted and carried her easily, laying her back on the lush chaise lounge off to the side.

She relaxed back into the soft and plush material of the ornate sofa, her legs falling open to reveal her dampened core. Crowley stared at her hungrily as he loosened his tie, just enough to slip the loop off his head and over hers, adjusting the tie to lie between her breasts.

“Looking more and more like mine by the minute,” Crowley smirked, rising from the sofa to strip himself bare.

Y/N watched with hungry eyes, licking her lips as his glorious cock was revealed to her. From head to toe, he was every bit as delicious as she’d imagined he’d be, still emanating power and authority without the amazing, tailored suits.

She licked her lips as he slowly climbed over her, his lips ghosting along her body but not quite touching, the tease of it making her squirm. He lapped at her nipple before encasing it in his mouth, humming at her responding moan.

In her distraction, he moved his mouth lower, sucking a mark on the underside of her breast. She jumped and hissed, the sensation making her core clench. She glanced down, seeing the mark he left behind, and giving him a questioning gaze.

“Only where it won’t be seen,” he answered her unspoken concern. “Want to see my Pet covered in my marks,” he growled at her, settling in on her other breast.

He worked his way down her body, leaving hickeys and love bites as he went, adorning her in his marks. She shivered beneath him, each new mark drenching her core. He worked his way between her thighs, teasing her and leaving even more marks, avoiding the sensitive areas where she was desperate for his touch.

Finally, he turned his attention to her needy and dripping core, lapping up her essence before focusing his energy on her clit.

With mostly his mouth and a little help from his hands, he guided her through a slow-building, slow-crashing orgasm that washed over her like a wave. The scratch of his beard against her sensitive skin added to the euphoric feeling.

He stood suddenly, making her whine from the loss of his touch. He smirked down at her as he rolled on a condom. She licked her lips once more, writhing with neediness.

“Hands and knees, Pet,” Crowley grinned, helping guide her into position. She gripped the armrest, curving her back and spreading her legs, her dripping pussy on display.

He groaned, gripping her ass in both hands and kneading the cheeks before slapping the right one harshly. Y/N jumped and moaned, the sting further igniting her lust.

“So responsive, Y/N,” Crowley crooned, before sliding deep within her core in one smooth stroke. “So eager; so much fun to play with,” he moaned, pulling out and thrusting in hard, relishing her surprised gasps.

Crowley set a fast and harsh pace, the slap of their skin leaving a red tint on Y/N’s ass and thighs. She let out a guttural moan as he hit her deep, rubbing deliciously over her g-spot and slamming into her cervix. The mix of pleasure and pain was setting her alight. Her hands clung to the armrest, her nails digging into the upholstery. Part of her was afraid she’d claw it to pieces; part of her didn’t give a damn.

His fingers found the tie, still around her neck, turning it to now lie down her spine. He gently tugged on the tie, showing her his intent.

“You good, My Love?” he asked, his hips never stopping their harsh pace.

“Y-yes, S-Sir!” she moaned out wantonly. He held her expertly on a high but kept her from crossing over, the torture of it exquisite.

Crowley wrapped the end of the tie around his hand, the other hand on her hip to steady her to take his cock. He tugged on the tie, simultaneously pulling her back on his cock and beginning to cut off her air. Her pussy fluttered and she let out a groan that made no sound, the pressure and pain bordering too much.

Suddenly, the pressure released and she sucked in a large breath of air, her pussy clamping hard around Crowley’s unrelenting length. He growled, both hands on her hips as he fucked her near flat on the sofa. She came hard, gushing around his cock, screaming out her release that seemed to reverberate off the office walls around her.

The intensity of her orgasm pulled Crowley into his own, thrusting deep within her and filling the condom, his hips still moving to extend their mutual highs.

After catching his breath, Crowley removed himself, disposing of the condom. Y/N lay on the sofa, the cool air of the room against her heated skin refreshing. She was thoroughly fucked and sated. Crowley more than delivered, the real thing far better than her fantasies could have conjured.

Hearing the clinking of glass, she rolled over, resting her head back against the armrest. Crowley approached, now wearing his slacks, with two glasses in hand. He offered her one, lifting her feet to sit on the sofa, and setting them back across his lap.

She took a sip from the glass, eyeing Crowley warily, his words and proposition from before still present in her mind.

“So,” she glanced at her glass, swirling the liquid within before meeting his eyes once more. “Be yours?”

He grinned and she matched his expression. He set his glass on the side table and rose, moving to his desk and digging in the drawer, finding what he was looking for and setting it on the small table beside her.

“A contract?” she asked excitedly as if he’d slid a jewelry box across the table to her.

She gave it a cursory review, finding it to be a detailed partnership agreement. She loved reading through contracts, finding loopholes, and exploiting or eradicating them, whatever suited her and her clients’ interests best.

It was solid, ironclad, and perfect. More perfect and romantic than flowers and dates and frivolous things that she wasn’t interested in. It was a great deal and one she was more than willing to accept. Included in their partnership was a VP position for her in Crowley’s firm - a right hand to the man himself - and control and Madame of the new female brothel that he intended to open across town.

Aside from more money and a great opportunity, it was a chance to share her life with someone. It wasn’t something she was ever really interested in, but with Crowley, her passion for business and appetite for sex crossed into a perfect match.

“And you wouldn’t be upset about me continuing to see your gentleman?” she asked with a quirked brow. She did not expect his hearty chuckle.

“My Dear, fuck whomever you want. It’s your heart and soul I’m after,” he grinned, cupping her cheek.

After reviewing the contract - and knowing she’d have her lawyers review it before signing anything - she grinned, “You little devil,” she teased.

Climbing into his lap, she wrapped her arms around his neck, grinding down against his cock which was already hard and ready for her.

“I accept.”

Chapter Text

Y/N woke up, groaning when she found the other side of the bed empty. She sat up against the headboard, wiping the sleep from her eyes. It had been a few weeks since Crowley presented her with his proposal and just a week since the paperwork had been signed and finalized. In that time, she spent most of her nights staying over at Crowley’s lavish penthouse.

She had given notice at her company but had a gap until the Partnership would take effect. So she found herself with an abundance of time and nothing to do. A vacation - or staycation, as Crowley put it - wasn’t something she’d ever really had. If she wasn’t working, she filled her time with things to help forward her career path.

Truth be told, she hated it. She was bored out of her mind and her restlessness was creating an itch under her skin. Crowley had even made a passing joke about it, having free time making her grumpy.

On top of it all, Crowley was busy with business which kept him away most of the time. She didn’t blame him, rather she was lousy with jealousy. She missed being busy.

Her phone chimed on the nightstand and she practically dove for it, almost hoping it was something business-related. It was a message from Crowley, but it still made her smile. She couldn’t wrap her head around this giddy little girl feeling she got when it came to him. She wanted to be disgusted at herself, but the twitter-patted little girl wouldn’t be deterred.

Meet me at the Den, I have a gift for you. XXX

Crowley. The Den. A gift? She practically hopped from the bed to the bathroom, getting herself ready for whatever Crowley had in store.

The Den was a welcome escape after the past few weeks. Crowley had spent as much time as he could with her since their first time together. She hadn’t had the time, or occasion, to return but she was certainly glad to be back. It was a haven for her, a place where she could let go and relax, not have to think but only feel.

She was warmly greeted by each staff member as she passed, though quite a few were missing, she assumed with clients elsewhere. She was starting to feel more at home, less like a client and part of the family. She hoped to get to know all of Crowley’s staff better over time, especially since she would be taking up VP of his enterprise. These were her people now, too.

As usual, Kevin found her before she had even seen him amongst the crowd. She followed him to Crowley’s table, said man’s eyes lighting up as she drew closer.

“My Love,” he greeted, kissing the back of her hand and excusing Kevin. He ushered her into the booth, her favorite drink already waiting for her. “How have you been enjoying your alone time?”

“It is terrible that I can’t wait to get back to work?” she huffed with a smirk.

He chuckled in understanding, “I know, Love. Just a few more days to finalize everything. I’ve already been compiling plenty that requires your attention.”

Her eyes lit up, Crowley always knowing just the right things to say and do to please her immeasurably. He understood her and shared her passions, and it only made her more and more sure of their partnership.

“In celebration of the signing of our agreement, I have a gift for you. A sort of ‘welcome to the family’ if you will,” he smiled warmly at her. “You’ve been so tense, so restless. So I’ve arranged for a very special treat for you, the very best, top dollar.”

Taking her by the hand he led her to the familiar staircase. She hadn’t walked the steps in quite a while, the familiarity of it all making her heart race in anticipation. The last time Crowley had a gift for her, she experienced Gabriel and the Sybian. It was an amazing, unforgettable experience and Crowley always seemed to know just what she needed, better than she did herself.

He led her down the hall of rooms but passed by each that she was familiar with, stopping at the very last at the end of the hall. He paused with his hand on the knob, smirking at her.

“Are you open-minded tonight, my Love?”

“Absolutely,” she grinned, the nervousness and fear that she used to feel gone, replaced by eagerness and trust in those around her.

Crowley let the door swing wide, ushering her inside from behind with his hands on her hips. It was a large and ornate room, a huge poster bed dominating the middle of the room. It was a lot like his office, but a bedroom. There were various furniture pieces, a few hanging swings and other playthings.

But what took her breath away was the sight of both Sam and Dean standing by either post at the end of the bed, wearing only loose hanging pants, their torsos and feet bare. They both flashed her a mischievous smirk, licking and biting their lips in turn as they eyed her hungrily.

“As I said before,” Crowley spoke into her ear, his hands wandering over her hips, “You’ve been so tense. There have been many changes in your life, many adjustments. You’re wound so tight, My Love.”

She hummed in agreement, her head lolling back on his shoulder as his hands and lips teased her, riling her up for what was to come.

“You need to be broken, ripped apart, so you can rise and move forward, leaving the ache and tension and worry behind you,” he whispered as he kissed along her neck and shoulder, his hands still teasing over her hips and thighs. She rolled her hips back into his, her eyes on the other two men.

Sam was biting his lip, his eyes taking in every detail of her body, every way she responded to touch. Dean was watching with a predatory gaze, fidgeting with a bit of rope in his hands. It made her clench her thighs, all three men chuckling as they took notice.

“Are you willing to be their playmate, my Love?” She nodded emphatically, swooning at the thought. Crowley gently pushed her forward, Dean stepping up to take her into his arms, turning her so she now faced Crowley, her back to his chest.

“She may be your Mistress now,” Crowley spoke to Sam and Dean. “But at the moment, she belongs to you.” He smirked as he left the room, closing the door behind him.

“You hear that?” Sam asked as he walked to stand in front of her, his fingers under her chin to lift her gaze to his. “You belong to us.”

“You want that?” Dean asked, rutting himself against her ass, kissing along her neck.

“Yes,” she breathed out in desperation. She had loved her time with each of them. It was rough and different and fantastic. Having both beautiful brothers together, to use her however they saw fit, seemed like exactly what she needed.

Sam gripped her chin a little tighter, forcing her attention on him. “You will call me Sir,” Sam corrected. “You may call him Dean.”

“Yes, Sir,” she nodded, her legs going weak as she was overwhelmingly aroused, Dean’s grip tightening to hold her upright between the two large men.

“We discussed it and we have a plan,” he continued. “We would like to tie you up, have you restrained and open for us. Would you like that?”

“Yes, Sir,” she moaned as Dean began to strip off her clothes very slowly, hips lips trailing along her neck and shoulders as he did so. They had thought about this, with her. How long had Crowley been planning this? Or was this something they planned themselves? Either way, it amped her arousal up to new and unfamiliar levels.

“Also, I am in charge. Neither you nor Dean will do anything, including cum, without my permission. Understood?”

Fuck. She was gonna die from dehydration at the rate she was slicking up. She had to be dreaming, but the sudden pinch of her nipple by Dean let her know it was all very real.

“Y-yes, Sir,” she responded, gasping as Dean’s fingers slid between her folds.

“Fuck, Sam, she’s so damn wet already.”

“You really are so perfect,” Sam praised, making her swoon once more. He grinned, loving her reactions. “Use your colors, okay?”

She nodded, gasping as Dean slid two fingers into her core, making her choke on her response to Sam.

“Dean,” Sam took on a commanding tone, “Get the rope, help me dress her up for us.”

Dean nodded and Sam guided Y/N back to the bed, letting her fall back onto its plush and inviting surface.

In a seemingly choreographed synchronicity, the brothers moved in tandem, securing rope and harness to bind her as they pleased. Their hands teased as they secured the various knots, their lips teasing over her skin, nipping and licking, making her squirm in desperation.

In a matter of minutes, they were complete, standing back to look over their handiwork. A sort of harness was fashioned around her torso, the rope outlining and lightly squeezing around her breasts. She was face down, ass up on the bed. Her arms were secured behind her back, her calves tied to her thighs, and her body posed in a hogtie, open and on display for the two gorgeous men.

“Fuck,” Dean cursed, his voice laced thick with arousal. “Knew you’d look good in rope.”

Y/N smirked, thinking back on her time with him when he had spoken those words to her. She squirmed, testing her binds, finding little to no give. She wasn’t scared, knowing they would take good care of her and stop anytime she needed.

“Color, Y/N,” Sam commanded.

“Green, Sir,” she cooed. Her pussy clenched in anticipation, feeling how wet she was already as the cool air of the room hit her exposed folds.

With her ass in the air and her face smashed into the sheets, she could only hear as they shuffled around the room behind her, the sound of rustling clothing and shuffling feet letting her know they were getting ready for her. Her breathing picked up with excitement. The bed dipped as she lifted her gaze enough to see Sam settling at the head of the bed, knees bent and hard cock hanging between his legs, but just out of reach - not that she could reach out to him in her bound state. She moaned at the sight, her breath hitching as she felt Dean’s hands grazing over her thighs and hips.

“We’ve been dying to get our hands on you again, you know that?” Sam asked as he languidly stroked his cock, her eyes glued, absentmindedly licking her lips, her mouth watering at the sight. Dean hummed in agreement from behind her. “So responsive, soft, wet…best damn pussy we’ve had in a long time. And that’s saying something,” he added with a smirk.

“Loved having you restrained and spread for me. Just like this,” Dean spoke, his lips ghosting over the skin of her backside and thighs, teasing and working her up without even really doing anything.

“Mmmm,” Sam hummed in agreement. “So many things I still want to do,” Sam added ominously.

“Sam,” Dean’s voice croaked as he squeezed her flesh a little tighter. “Wanna taste her. Please?”

Something about Dean asking his brother’s permission - begging to taste her - made her hot all over, an involuntary shiver running through her. Sam’s long fingers tucked under her chin and lifted her gaze to meet his eyes.

“Wanna watch your face while Dean eats you out,” he whispered, his filthy words igniting her further. “You should see how hungry he looks. Do you want him to taste you?”

“Yes,” she responded breathily. Sam’s tsk made her pout.

“Yes, what?” He corrected, pinching her chin a little more firmly. His commanding tone had her pussy clenching around nothing.

“Yes, Sir,” she amended, purring under his approving hum.

“Go ahead, Dean,” Sam encouraged with a nod. “Show her how good you are with that mouth of yours.”

Dean responded with a desperate groan. A second later, she felt his tongue spear her open, licking against her eager walls. Dean’s hands spread her cheeks wide, her dampened folds glistening in the light of the room. His noisy slurping, grunts, and groans had her breath stuttering, her hips attempted to grind back into him but she couldn’t move.

Dean certainly knew how to use his mouth, bringing her to the quickest orgasm of her life, her moans and breath bouncing off Sam’s face as he held her chin and gaze steady.

“Dean, stop,” Sam’s commanding voice spoke. Dean immediately stopped leaving Y/N bereft of his touch, her soaked folds catching the chill in the air. Her eyes met Sam’s intense gaze and she knew she was in trouble. Her pussy clenched at the thought. “Do you know what you did wrong?” he asked, still holding her chin firmly in his grasp.

“I-” she worked her dry mouth, wiggling in her bindings. “-I came without permission.”

“You did,” he confirmed. “Now you’ll be punished so you remember the rules,” he smirked, releasing her chin.

She lay limp on the bed, her ass still in the air, as she watched Sam move from the bed. Dean slid into his place, leaning against the headboard and watching with a broad grin.

“I’m going to spank you,” Sam spoke, his hand caressing her ass cheeks. “I want you to count.”

“Yes, Sir.”

She was wetter than she had ever been in her life. As his hand came down for the first smack, she yelped in surprise before moaning wantonly. With each smack she counted, her moans increased in volume. By the time he was done, her ass was red and sore, pulsing with heat, adding to her ever-growing need for more.

“So beautiful,” Sam praised, leaning in to peck her lips. “Such a good girl for us.”

“T-thank you, Sir.”

Dean moved away, leaving her missing his touch immediately. Sam’s chuckle had her turning her gaze to him once more.

“Dean’s going to fuck you first,” Sam explained, rising to his knees in front of her. “I want that mouth on me,” he declared, stroking himself and licking his lips as he stared at her mouth.

The thought of being impaled between them, the two of them using her for their pleasure had her damn near cumming again. She was repositioned, now facing Sam where he stood at the end of the bed. She could feel Dean shifting behind her, getting into position. Her body clenched in anticipation over and over.

“Y-es!” she exclaimed, her voice broken as Dean suddenly thrust deep within her, holding still and squeezing her hips as she adjusted. Her mouth hung open and Sam took the opportunity to run his cock along her lips before slipping into her hot and wet mouth.

Using the rope that bound her for leverage, Dean pulled her back into his every thrust, letting him hit deeper and harder than she’d felt before. Sam fucked her mouth and throat, seeming to know when she needed air and when she could swallow him down. Though Sam was so big she was struggling to take more than half, but she was determined. Sam didn’t seem to mind, using her mouth for his own pleasure, his intense eyes studying her every move, his ears tuned into her every sound. She relaxed a little, despite the tension building in her body and core, knowing they would take care of her. She had no reason to worry about anything except absolute pleasure.

“Fuck! So fucking good,” Dean groaned, his hips slapping hard against her ass again and again. He was struggling to maintain control himself, his eyes glued to his cock sliding in and out of her soaked pussy. She clenched particularly hard around him and he let out a drawn-out groan, his head rolling back on his shoulders.

Feeling herself growing close, she pulled back off of Sam, her mouth hung open as she tried to get herself to form words. “P-please,” she whined, her breath broken by every hard thrust Dean gave, his own moans driving her further. She wasn’t sure she could hold off her climax much longer. “Please. Sir,” she gasped, looking up at Sam through her lashes as Dean continued to pound her ruthlessly from behind. “Please let me come.”

“Dean, stop,” Sam commanded, Dean immediately stopped his thrusts and pulled from within her core, leaving her to gasp out in disappointment and loss.

In a flash, she was flipped on her back with her legs spread and arms tucked behind and under her forcing her to arch her back, her breasts bound and exposed, perked up by the angle and the bindings. Dean positioned her head in his lap, cradling her face and smiling down at her. She turned her head, wanting to get her lips around his hard shaft that still glistened with her arousal.

“No,” Sam rebuked, gently slapping her inner thigh for emphasis and turning her attention back to him. “You already got him so worked up,” Sam teased the two of them. “He’s got no control with you,” Sam smirked, Dean uttering 'bitch’ under his breath.

“But you do?” she breathlessly teased, smirking when Sam’s gaze grew darker.

“He's always in control,” Dean responded, leaning over her to catch her gaze again. She was distracted by Sam’s hands roaming her thighs and avoiding her most intimate areas, but Dean held her gaze on him. “It’s kind of annoying,” he added, making her chuckle.

It amazed her how they could still be playful brothers with her bound and open and merely a plaything between them. It made the whole thing feel less sordid and more…fun. Like friends just having a good time, hanging out, fucking each other senseless.

“You ready for more?” Sam teased, lowering his head to kiss along her breastbone, his fingers still teasing over her skin, raising goosebumps.

“Yes, Sir,” she crooned effortlessly, her eyes fluttering closed as his lips wrapped around a nipple.

“So beautiful,” Dean praised, his hands gathering her breasts and pinching her nipples when Sam moved away.

Sam grabbed her hips, placing her ass on his thighs. Rubbing the head along her folds and bumping against her clit, he covered himself in her juices before entering her in one smooth and harsh thrust. She cried out at the sudden intrusion, not painful but surprising.

“Color,” Sam demanded through clenched teeth, holding himself still and deep.

“G-Green,” she cried out, trying to wiggle her hips for friction but having zero give between her bindings and the two glorious men.

Dean’s eyes left hers to trail down her body, stopping where Sam penetrated her. She allowed her eyes to follow the same path, finding herself split wide open by his impressive girth. It made her gasp and Sam chuckled in response. Holding her hips tight in his large hands he pulled nearly all the way out before slamming himself back home again. Sam fucked her slow but deep and hard, watching her breasts bounce with every thrust.

“Damn, that’s hot,” Dean spoke, watching Sam thrust deep within her again and again, her body firm in his hold. “Love seeing women take that monster,” he chuckled, looking down at Y/N in his lap, his gaze growing darker. “Never seen anyone take every last inch though.”

She moaned as Sam adjusted and hit a spot within her that had her seeing stars. Dean sucked two of his fingers into his mouth, saturating them in his spit. With a wicked grin and his eyes locked on hers, he moved his hands to her folds, his fingers landing either side of her clit. He began to gently massage, testing her reaction as Sam increased his pace, lifting on his knees to spear her harder and deeper. Her hips held tight in his capable hands she squeezed her eyes shut tight against the onslaught of sensations coursing through her. Careering towards her climax at an alarming rate, her eyes popped open in urgency.

“Please! Sir, Dean…I’m gonna-”

Dean’s hand disappeared and Sam stilled his hips. She whined and tried to wriggle against him but could barely move, her walls clenching against Sam’s cock repeatedly. Four hands helped move her, sitting her upright in Sam’s lap, still impaled on his thick cock. His hands cocooned her against him as he peppered her neck and chest with kisses, silently urging her to calm down.

“Not yet,” Sam whispered, wiping the sweaty strands of hair from her brow. “Dean and I are gonna fuck you together now,” he spoke, Dean’s hands reappearing as he teased at her back entrance.

Before he could ask, her eyes were rolling back in her head as she groaned, “Green.”

The brothers chuckled as Sam returned to his calming ministrations, gently rocking himself into her. Dean’s fingers returned, now with what felt like lube, as he breached her rear entrance, prepping her to take them both. She wiggled in Sam’s lap, growing impatient and desperate to cum but held off by the capable, infuriating, and incredibly sexy men.

“Please,” she begged as she tried to squirm again. “I’m ready. Want you both.”

She went still as Dean worked himself inside her. She felt stretched to her limits, every nerve ending on fire as they were both finally settled within her.

“You okay?”

“Yes Sir, Dean,” she moaned, her eyes opening to lock onto Sam’s.

With the same synchronicity they showed while tying her in rope, they moved in tandem, fucking her deep and fast, her body held tight between them as they worked to bring them all to an end.

“Fuck, you’re so hot,” Sam groaned. “Didn’t get to see your face when you came for me last time,” he continued, glancing down at where he fucked into her and biting his lip, meeting her eyes again. “Dying to see you come undone for me.”

She was absolutely floored at their stamina. No wonder they were the most requested of all the males on offer at the Den.

“She’s fucking stunning,” Dean growled from behind her, his hips picking up pace, cock throbbing with his impending release. “Her eyes roll back, her skin gets flushed, her whole body tenses, and she makes this high-pitched keening sound like she’s just winding up too far until she snaps.”

“Fuck,” Sam groaned. “That sound!”

They both fucked her harder, chasing her release more than their own. She was surprised that their talking about her in such a way only wound her up more. She clenched hard, feeling herself climbing to that crescendo much as Dean described.

“There it is,” Sam and Dean spoke in unison as Y/N’s voice began to hitch higher and higher, her muscles tight in anticipation of her release.

“Not gonna last,” Dean huffed, his cock throbbing and twitching hard with every brutal thrust.

“Fuck, me either,” Sam’s eyes rolled back as he thrust harder. “Go on then,” Sam commanded. “Cum.”

As if waiting for the words, Y/N and Dean came together. Dean ground hard into her as she shook in their arms, a scream tearing from her throat. Sam growled as he came, her squirting and quivering pussy too much and too good for him to hold out any longer. Her body was spent, her energy drained with the most powerful orgasm she’d ever felt. She was only vaguely aware as they pulled from within her and laid her back on the bed.

Eyes closed, catching her breath, Y/N could only hear and feel as they worked to remove the rope from her body. They gently straightened out her limbs, massaging the aching muscles. A sweet smell reached her and she felt the coolness of the balm as they soothed her sore and well-fucked body.

“You were so good, Sweetheart,” she heard Dean’s voice, his breath fanning over her neck. Her eyes fluttered open and she was met with stunning green, an amused smile on his lips. “How’re you doin’?”

“Floating,” she managed, feeling the dopey grin that spread on her face.

They continued to massage and soothe her, cleaning up her body, sitting her up to drink water, and praising her repeatedly. God, the aftercare alone was worth the cost. Sitting back against the headboard she let her eyes roam over the brothers, both laid out along the ends of the bed, admiring her right back.

“Thank you,” Dean spoke, lifting her hand and kissing the back of it. “For being our playmate.”

She grinned and turned to Sam when he took her hand, kissing it the same. “And welcome to our little family,” he grinned with a glint in his eyes, “Mistress.”