Chapter Text
“It’s suicide, Dean!” Hailey shouted, slamming the bedroom door behind her.
She had just arrived at the clubhouse minutes earlier to find that her boyfriend, the president of the Kansas charter Fallen Angels MC, was on his way out with his boys to get some payback on a rival club for stealing one of their weapon shipments a couple weeks back.
“I know what I’m doing Hails,” Dean yelled, taking a step forward so that he was in her face.
“You’re unbelievable! The scenario you’re about to going diving into head first is unpredictable, fuckface. What if they are waiting for you? What if you walk into an ambush?” Hailey asked angrily, shoving Dean in the chest.
“You don’t think I’ve considered the possibility that this could be a trap? Of course I have! That’s why we’re going in guns blazing, baby,” Dean stated cockily.
“Oh yeah that’s right, I forgot you’re Mr. fucking Invincible. Well, tough guy, since you are so damn hell bent on disregarding your own safety, I’ve got a different question for you. What about me? What about Cas? Who’s going to take care of us if this shit goes sideways and you end up taking a bullet?” Hailey inquired, her blood boiling in her veins.
“You know I have a backup plan set-up for you and Cas in case something was to ever happen to me. You two would be well taken care of. Trust me, neither of you will want for anything,” Dean said, barely getting the words out of his mouth before Hailey slapped him across his right cheek as hard as she could.
“You heartless piece of shit! Do you really think Cas and I give a fuck about money?! We don’t want your money, you fucking bastard. We want you, alive and with us,” Hailey screamed, her face red with rage.
“Oh, so now you’re speaking for Cas?” Dean questioned, grabbing her by both her wrists to push her back against the computer desk that was positioned along the far wall of the room.
“Yes! And don’t you dare act like he doesn’t mean as much to me as he does to you. Cas is my everything. You both are,” Hailey confessed, yanking away from Dean’s bruising grip.
Remaining silent for a moment, Dean let his arms fall to his sides as he stared at her angrily, his chest heaving.
If he was being honest, he felt the same way Hailey did. Castiel and she were his life, and he would do anything to keep them safe. Dean had fought tooth and nail to be with them both, neither of them being in favor of sharing him at first, but now, five years later the three of them were in love and inseparable, and he wasn’t about to lose that. He only wished he could express that sentiment to the beautiful and passionate woman standing in front of him.
But he was too pissed. And being the vindictive fucker that he was, he just couldn’t make himself show her that he cared.
“Wow, I always knew you were a clingy slut but damn,” Dean taunted, refusing to let the devilish smile that was painted on his lips fade away when Hailey smacked him once more.
“Fuck you!” she yelled, spiting in his face.
“If that’s what you want, slut,” Dean replied wickedly, not bothering to wipe the salvia off his cheek before grabbing a handful of her long brown hair to pull her into a forceful, hate-fueled kiss.
Wrapping her fingers around the leather material of his kutte, Hailey kissed him back with equal intensity, moaning when Dean’s hands found her breast, massaging them through her black mesh shirt.
“I fucking hate you,” she breathed out as Dean moved his lips away from her mouth, trailing kisses down to her neck.
“Keep telling yourself that, baby girl,” Dean teased before sinking his teeth into her jugular, tasting blood as Hailey screamed in pleasure.
“Fuck!” she groaned, feeling Dean lap at the bite mark he had just made with his tongue.
“I bet that sweet little pussy of your is soaked by now,” Dean growled, sliding his hand down the front of her body to undo the single button on the denim skirt she was wearing.
“Y-you wish,” Hailey retorted, shivering when she felt cool air hit her thighs as Dean pulled her skirt down all the way so that it was pooled around her black stiletto boots at her ankles, his action revealing the pair of red, lacy panties she was wearing.
“Really?” Dean asked cockily, leaning forward to kiss the bruise that had already begun to form on her neck. “Let’s see about that, shall we?” he added as he started to rub her clit through her panties, smirking when he realized that the soft material was slick with her arousal.
“You are such a smug jackass,” Hailey gritted out, failing to stop herself from rolling her hips, working her pussy against Dean’s hand.
“You better watch that smart mouth of yours, slut. I’ve been lenient with you thus far, but you’re trying my patience,” Dean threatened, sliding his hand over her crotch so that he could use his palm to massage her clit.
“Oh, that’s right. I’m talking to the prez, aren’t I? A big, strong, alpha male like yourself can’t have a bitch like me telling him what a jackass he is, now can he?” Hailey asked maliciously.
Stilling the hand that was between her legs, Dean responded to Hailey’s sarcastic comment by backhanding her with his free hand, the force of his blow busting open her bottom lip.
“You wanna mouth off again, you filthy fucking whore?” Dean growled, roughly grabbing her by the chin to make her look him in the eyes.
“What if I did, macho man? You gonna slap me around until I behave like an obedient little bitch?” Hailey questioned, a sadistic grin on her face. “Good luck with that baby, ‘cause it’s never going to happen. If you want someone to submit to you, I suggest you call Cas. I’m sure he’d drop everything and leave work in the middle of the day if you told him to come sit on your dick. He loves it when you tell him what to do,” Hailey teased, making Dean let out a sharp gasp when she reached out to palm at the bulge in his jeans.
“Yeah, he does. And he also knows how to keep his mouth shut. Cas is good for me like that. He takes my dick so fucking good and does what pleases me,” Dean replied, praising his other lover in hopes of making Hailey jealous.
“That may be true. But what you don’t know is that when you are off on club business and it’s just me and Cas, your obedient little whore grows a pair and fucks me like a man should. He makes me cum so fucking hard on that big, gorgeous cock of his and it’s his name I’m screaming, not yours,” Hailey shot back, making Dean tremble with rage.
“What are you trying to say, baby?” Dean asked, his tone controlled by furious. “You trying to tell me that Castiel gives you what you need better than I do? ‘Cause that’s fucking bullshit and you know it,” he added, grabbing her by the hips to roughly shove her back against the desk, the edge of the wooden structure colliding with her low back, creating a long, purple bruise.
“Is that so? You think you’re the only man that can satisfy me completely?” Hailey questioned, ranking her fingernails down his chest and over the white t-shirt that he was wearing under his kutte.
“I don’t think that Hails, I know it. Yeah, you love Castiel and he means the world to you, but don’t forget that I’m the glue that’s holding you two together. At the end of the day, if push came to shove, the both of you would pick me over the other. You two would sacrifice each other in a heartbeat if it meant saving me,” Dean said, a twisted smile on his face.
“And you fucking love that don’t you? You sick fuck,” Hailey spat, her breath hitching in her throat when Dean sank to his knees in front of her.
“Guilty as charged,” Dean retorted, slowly pulling down Hailey’s panties, exposing her throbbing, wet pussy.
“You are disgusting,” Hailey said weakly, wishing that she meant it as Dean removed her skirt and underwear from around her ankles, tossing the material to the side.
“And it turns you on so much, doesn’t it baby?” Dean asked, scooting up to lift her right leg over his shoulder before slapping her pussy teasingly, making her cry out in pleasure.
“Yes, Dean please,” she begged, feeling him circle his thumb around her clit, the action setting all of her nerve endings on fire.
“That’s much better,” Dean chuckled, leaning forward to lick up the length of her pussy while simultaneously slipping his index finger inside her.
“Oh fuck!” Hailey mewled, running her right hand through Dean’s short brown hair as she threw her head back in ecstasy.
Swirling his tongue, Dean worked at her clit, licking and sucking at the sensitive bundle of nerves as Hailey used her hand to press his face further down into her pussy.
“So fucking wet for me, baby,” Dean moaned, pumping his finger in and out of her while she screamed his name. “Your pussy tastes so good,” he continued, looking up at her with a mischievous grin, his lips glossy and slick with her arousal.
“Dean! Oh God, please,” Hailey panted, shuddering when he started licking her pussy, the stroke of his tongue short and teasing.
“You want me to fuck you, Hails? Or are you are going to cum on my tongue like a desperate little whore?” Dean asked huskily before biting her clit, rolling the skin between his teeth as he tugged on it roughly.
“Holy fuck!” Hailey yelled, pulling his hair. “Want you to fuck me, baby. Fuck me hard, wanna cum around your dick,” she whimpered, her body tingling with pleasure when Dean slapped her pussy again, this time a little harder.
“Turn around,” Dean ordered, roughly pushing her leg off his shoulder as he moved to stand up.
Doing as she was told, Hailey positioned herself to face the wall, lying flat on her stomach against the desk so that her legs were spread apart and her bare ass was exposed to Dean.
“Damn, look at you,” Dean hummed, sounding completely wrecked. “You look so fucking good bent over in front of me wearing those fuck me boots and showing off that tight little ass of yours.”
“Dean, baby please. I need you inside me,” Hailey begged, gripping the top of the desk tightly when she heard the man behind her unbuckling his belt.
“I know you do, sweetheart. You’re so fucking wet that it's dripping down your legs,” Dean rasped out, running his hand up the inside of her left thigh, getting his palm slick with her arousal as he caressed her skin.
“Dean,” Hailey pleaded, crying out when Dean smacked her ass.
“That’s right. Beg for it, slut,” Dean demanded, placing both of his hands on her hips to pull her back against his erection, which was now free of his jeans and boxers.
“Oh fuck, baby please!” Hailey groaned, feeling his dick, wet with pre-cum, pressed between the cheeks of her ass.
“Tell me how bad you want my dick, you needy whore,” Dean said, slapping her ass again, marking her with his hand print.
“I want your dick so bad, baby. Want you to fill me up, make me cum so hard that I can’t breathe,” Hailey confessed, letting out a grateful little sigh when Dean lined himself up with her pussy, slamming into her.
Wrapping her tangled hair around his left hand, Dean began to thrust his hips violently, pulling her up off the desk so that her back was pressed again his chest.
“I love hearing you beg for my dick, slut,” Dean whispered in her ear, curling his right hand around her neck as he continued to pound into her.
“Oh, faster baby. Fuck my pussy hard! Fuck me like a man, Dean!” Hailey commanded, knowing her words would get a rise out of him.
“You want me to fuck you like a man, whore?” Dean asked, tightening his grip on her neck.
“Yes! Please, please!” she begged, gasping for air as Dean fucked into her relentlessly.
“That’s it baby, let me hear every one of those filthy noises you make when I’m splitting you open with my dick,” Dean said, nipping at her earlobe.
“D-Dean, I’m…so close,” Hailey whined, her whole body shuddering when Dean removed the hand that was tangled in her hair to reach between her legs and massage her clit.
“C’mon, whore. Wanna feel your soaking wet little pussy tighten around my dick when you cum like the desperate slut that you are,” Dean moaned, a warm sensation of pleasure pooling in the pit of his stomach when he heard Hailey scream his name in response.
Thrusting his hips faster, Dean squeezed the hand that was around her neck even tighter, cutting off her oxygen as he lowered his mouth to her right shoulder, biting down hard on the exposed flesh.
“Fuck, yes!” Hailey gasped, her eyes rolling into the back of her head as an orgasm hit her hard.
“Good girl,” Dean praised, continuing to roll his hips until she was whimpering beneath him.
“Dean, baby, I can’t take any more,” Hailey mewled, her body completely spent as she slumped forward against the desk when Dean finally released his hold on her neck.
“You jumped the gun on me, Hails,” Dean teased, pulling out of her gently.
“I know, I’m sorry handsome. How ‘bout I make it up to you by letting you cum on any part of my body that you want to?” she asked, earning a loud, animalistic moan from Dean.
“Fuck, I like the sound of that baby. And I know exactly where I’m going to blow my wad, all over this perfect ass,” Dean said, smacking her right ass cheek where the outline of his hand was still red and visible.
“Do it, c’mon Dean. Let go,” Hailey coaxed, looking at him lustfully over her shoulder as he began to stroke himself, positioning the head of his rock-hard, leaking dick over the crack of her ass.
“You’re such a mouthy, stubborn bitch,” Dean moaned, jerking his hand at a rapid pace. “But I fucking love you.”
“I love you too, Dean. I’d do anything for you,” Hailey confessed, biting her bottom lip sensually as Dean came, splashing long, warm ropes of cum all over her ass, the liquid oozing down to the back of her thighs.
“Motherfucker,” Dean mumbled under his breath, his eyes hungrily taking in the sight before him. “Stay still for a minute, baby. I want to enjoy this,” he added, admiring Hailey’s ass, red and covered in his hand prints, dripping with his cum.
“Like what you see, handsome?” Hailey asked, wiggling her ass at him.
“Oh yeah…As a matter of fact,” Dean said as he bent down to grab his phone from his jeans. “This is worthy of a snapshot,” he continued, unlocking the device to switch it to camera mood.
“That for your spank bank, Winchester?” Hailey joked, staring back at him longingly as he snapped the picture.
“Abso-fucking-lutely. But I’m also going to spend it to Cas,” Dean laughed, attaching the photo to a messaging that read, Wish you were here before sending it to his other lover.
“Poor baby, he’s working! He’s trying to be a productive member of society and you’re taunting him with dirty pictures,” Hailey scolded, finally standing up.
Gingerly, she turned around; her legs a little unsteady as she leaned back to sit on the desk.
“You know I hate that he works. This is my way of protesting,” Dean grumbled, walking forward to wedge himself between Hailey’s thighs, putting his cell phone on the desk next to her before wrapping her legs around his waist.
“Yes, I’m highly aware that you hate that fact that Castiel has a job. But it’s his decision baby. Not everyone likes being a kept whore like me,” Hailey teased before placing a chased kiss to his lips.
“You still mad at your sugar daddy?” Dean asked, running his hands up the tops of her thighs which were slick with sweat and cum.
“Honestly? Yes. I hate that you make such reckless decisions knowing that Castiel and I are going to be the ones to suffer from them…” Hailey admitted, resting her palms flat against his kutte. “I know if ‘you love the man, you’ll learn to love the club’ but it kills me knowing that you are putting yourself in unnecessary danger.”
“I can’t neglect my duty to the club ‘cause my old lady and my old man want to keep my ass outta the fire,” Dean stated as a matter of fact.
“…I know, and so does Castiel. Why do you think we put up with this shit on a regular basis? We know nothing’s going to change and you are going to do what’s right by the club. And even though we hate it, Cas and I stay because we love you. However, just because I know you’re a stubborn bastard and set in your ways, that doesn’t mean that I’m going to stop trying to talk you out of stupid shit,” Hailey said, ruffling his hair playfully.
“How’d I get so damn lucky to find the two of you?” Dean questioned, his tone gentle and affectionate.
“Cas and I just got low standards, I guess,” Hailey taunted, giggling when Dean started tickling her sides.
However, thankfully for Hailey, his assault was ended by the sound of his cell phone going off. Reaching over to pick up the device, Dean opened the new text message from Castiel, taking a moment to read it before busting out into laughter.
“What’d he say?” Hailey asked, taking the cell phone as Dean continued to howl.
To: Dean
From: Cas
Thanks for that, baby. ‘Cause the thing I needed most was to pop a boner while I’m at my job, as a kindergarten teacher, surrounded by CHILDREN.
“Oh that’s just not right,” Hailey chuckled, shooting Dean a sheepish grin.
“He’s going to be livid when he gets home,” Dean mused, mischief gleaming in his bright green eyes.
“Looks like more angry sex for you, Winchester. It’s the hard-knock life, isn’t baby?” Hailey inquired.
“It is. And I’m just trying to get by a little at a time,” Dean replied, unable to hold back a laugh.
“I love you…Even if you are a narcissistic bastard with a god complex,” Hailey confessed, kissing Dean again.
“Good. Now just remember that when I walk out that door in a few minutes to help my club with some payback,” Dean said, making her sigh.
“Just go, Winchester. But I swear on my life if you die, I’ll resurrect you so I can beat the fuck out of you and then put you back in the ground myself,” Hailey threatened.
“I’ll be fine, baby. I shouldn’t be out any later than midnight. Maybe Cas, you, and me can have some fun when I get home?” Dean suggested, cupping both her cheeks in his hands, rubbing circles against them with his thumbs.
“Can’t wait, baby,” Hailey said, reluctantly conceding to him, “Just be careful.”
“I will, Hails. I love you, baby girl,” Dean told her before kissing her passionately.