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Office Affair

Chapter Text

She loved her job. Really she did. She didn’t have a shitty boss - not like inthe past. He was kind to her, he remembered her name, her birthday, hell last Valentine’s Day he’d walked in carrying a fancy flower arrangement; she had asked if he wanted her to have it delivered to his girlfriend, but instead he just shook his head. “It’s for you” he’d said gently placing crystal vase on her desk.

Dean Smith was hands down the best boss a girl could hope for. She was taken from her thoughts when the intercom on her desk buzzed.

“Y/N. Could you come in here please?” Mr. Smith’s came over the intercom.

She pressed the return button. “Yes sir, I’ll be right there.” She grabbed her legal pad, and pen, and headed into his office.

“What do you need sir?” She smiled, standing in the doorway.

He looked up at her, taking his headset off for probably the first time all day. “Alright Y/N, I’m going to talk fast because this all needs to get done today” He began.

“Bring it on sir, I got this.” She grinned.

“Of course you do. Two years, and you haven’t let me down once. This stack of files” He placed his hand on a tall stack “need to be alphabetized, and handed out to the right people. The distribution list is here on top.”

She nodded scribbling on her pad.

“That needs to be done by the end of the day. I also need you to file all of the reports I’ve finished. That also needs to be done by the end of the day. I need you to order my lunch for me a-”

“A Cobb salad, ranch on the side, I know sir. Although I would say I know don’t where this new health kick has come from, but it’s completely unnecessary.”

Dean sat back in his seat, eyebrow raised. “Oh?”

“If I’m being too forward, I apologize, but to be honest sir, you look great. You always do. You have no idea how many of the women here come by just to tell me how jealous they are I get to work with you.”

Dean smirked, amusement clear in his expression. “Well what do you think I should get for lunch then?”

“I think you’ve earned that burger you so much from Harvelle’s Bar and Grill.”

“With a pile of steak fries just the way I like’em?”

“What’s a burger without fries?”

Dean laughed. “Alright then, you win.”

“Don’t I always sir?” She smirked.

“One more thing before you go.”

“Coffee refill?”

“You read my mind.”




It was eeking on four-thirty when she stormed into the office. She was pretty, long dark hair, and a dark complexion to match.

“I need to see Dean.” The woman demanded standing at Y/N’s desk.

I’m sorry Miss, he’s in the middle of a meeting, would you mind waiting? He shouldn’t be much longer.”

The woman frowned. “Just take a message then.”

Y/N nodded grabbing her pad, “Alright, what would you like me to tell him?”

“Tell him it’s over, I’m moving out, and here’s his fucking ring back.” The woman slammed an engagement ring down on Y/N’s desk, then walked away. Y/N watched taken aback as the woman got on the elevator. She picked up the ring to examine it. It was a thin silver band, with a perfectly sized diamond in the center. It was simple, but beautiful.

Not five minutes later Dean’s office door opened. He, and Mr. Adler exited the room.

“So we’re still on for golf next weekend?” Mr. Adler smiled.

“Wouldn’t miss it for the world sir.” Dean replied. He waited until Mr. Adler was out of sight, and headed to Y/N’s desk, seating himself of the edge of it.

“What did I do to deserve you?”

“Excuse me?” she asked confused.

“Mr. Adler was in there telling me how promptly he received the files he asked for. He asked for them this morning, and was surprised to have them before lunch. You Y/N, are amazing.”

“Well alphabetizing files, and delivering them isn’t exactly rocket science. But um sir… there’s something I need to tell you.”

He folded his arms, leaning closer to her. “What’s on your mind?”

“A-a woman came by looking for you, and um… she wanted me to tell you it’s over, and to give you this.” She held out the ring to him. Her heart practically broke when she saw the way his face fell. “I’m sorry sir.” She whispered, as he took the ring.

He sighed, “No. It’s my own fault. I should’ve paid more attention to Lisa, instead of working so much.” Dean stared at the ring a moment longer, and then tucked it into his pocket.

“Head home early, Y/N. Get a start on your weekend.”

“Oh…um, no sir. That’s fine, I’ll stay. I don’t mind.”

Dean smiled, it didn’t reach his eyes though his heart wasn’t in it.

“Go home. That’s an order.”

Y/N sighed. “Yes sir.”




“I told you to go home.”

“Holy shit!” Y/N jumped, nearly knocking her drink over. She was sat at the bar of Havelle’s Bar and Grill; it was the closest bar to the office, and as such it saw a lot of business. Dean sat himself down next to her.

He smirked at her, his hair ruffled like he’d been running his hands through it his tie was gone, and a few buttons of his shirt were undone. She had to say, tipsy looked good on her boss.

“Well?” He demanded.

“It’s Friday, sue me I wanted a fuckin’ drink. Why aren’t you at ho-” She cut herself short. “Shit. Sorry.”

Dean either didn’t notice, or ignored her slip up, and continued on, “You have quite the potty mouth off the clock.” Dean noted.

“I ain’t getting’ paid to be a kiss ass right now am I?”

Dean frowned. “Is that all you think it is? You’re just getting paid to kiss my ass?”

“Don’t get me wrong Mr. Smith, I love working with you. I mean…you’re probably the nicest boss I’ve ever had. You gave me flowers on Valentine’s Day.”

Dean looked away sheepishly. “I was actually going to have you deliver those to my girlfriend at the time but…she had left me that morning.”

“Fuck man, dumped on V-Day? You got shit luck when it comes to the ladies huh?”

“Well the woman I thought I was going to spend the rest of my life with left me today so…yeah. It sucks.”

“Look at you two.” The bartender came over to them, a smile on her face, dark hair framing her face. “My son ain’t givin’ you a hard time is he?”

Y/N’s eyes widened.

“Son?” She demanded looking at Dean, “Your mother owns the bar?”

Dean chuckled, holding out his glass for his mother to refill.

“Ellen Harvelle…well Smith, but Harvelle is my maiden name.”

Y/N took her offered hand, and shook it.

“Now I know why you love the food here so much.” She shook her head.

“If he starts misbehavin’ you let me know. I’ll set him straight.” Ellen offered, hand reaching out to ruffle Dean’s hair.

“I’ll be sure to” She chuckled, watching as Dean tried to swat her hand away. Ellen walked away, laughing to herself. “Well if you didn’t treat me right before, you’d better now otherwise I’ll have to tell on you.”

Dean sighed, scratching his forehead. “You wonder why I didn’t tell you my family owns the place.”

“So um…are you okay?” Y/N asked voice laced with concern.

“I will be. I just want to get drunk, and go home, and pass out.”

“I can drink to that.”




“I really shouldn’t be doin’ this” Dean grunted, his voice losing that college boy edge, it was deeper, his accent a little more pronounced.

“Like we’ll remember in the morning?” Y/N panted as he mouthed at her neck. He had her pinned against the door of her apartment. They were both drunk, and had taken a taxi back to her place. He hadn’t wanted to go to his apartment, after all his ex-fiancée was still moving out.

“I… I’m just thinkin…maybe I didn’t think this through all the way.”

“Mr. Smith-”

“See! You’re still callin’ me Mr. Smith!”

Y/N took a deep breath, “Dean. Look at me.”

His eyes locked on hers.

“Dean, I think you’re attractive. I’ve been wanting to fuck you since day one. This isn’t something spur of the moment, it’s been building up for a long time…and I feel like feel it too.”

Dean stared a moment longer, then gripped her hair in a tight grasp yanking her head back.

“I’ve always wanted to bend you over my desk, and fuck you till you couldn’t walk straight. Everyone at work would know I was the one who fucking did that to you, they would know you were mine. Maybe I still will, and mark you up real good while I’m at it. Get that I.T. guy to stop coming by your desk every day, finally get him to fuck off!” Dean growled against her throat.

Y/N tried to breathe, but Dean was making it hard to. “S-Sam? Sam’s harmless.”

“You fuckin’ know his name?”

“What’re you jealous?” She smirked, Dean pulled away looking right at her.

“Yes. You’re mine Y/N. Since day fuckin’ one.”

“And what’re you gonna do about it?” She knew she was goading him on, but she didn’t care.

“I’m goin’ to fuck you into your mattress. Fuck you so hard you’ll feel me for days. Fuck you so good you never think of another man but me.”

“Oh God, please!” She begged, her voice edging on a whine.

“You’ll get what you want sweetheart. Where’s your bedroom?”

“Down the hall, on the left…fuck Dean, I need you right now.”

Dean practically growled in response as he dragged her to her bedroom. He pushed her down on to the bed, yanking his tie off, and throwing it across the room.

“You have too many clothes on.” He grunted, fumbling with the buttons of his own shirt in his inebriated state, but he managed to undo them all without ripping them off. Y/N took that as her hint to start undressing.

As soon as Y/N had managed to finally get her bra, and panties off Dean was on top of her, his cock hanging hot, and heavy pre-come glistening at the tip.

“I hope you’re ready sweet heart, ‘cause I don’t got time for foreplay. I gotta get in that sweet pussy.”

“Fuck, yes. Want you, want you in me.”

“Goddamn, I don’t have any condoms on m-”

“Nightstand drawer.” Y/N grunted reaching, and pulling it open to reveal an assortment of condoms. Dean tilted his head in question.

“What the fuck?”

“Well I mean it’s not like I have guys over here every fuckin’ night. But it never hurts to be prepared.”

“Is that a glow in the dark one?”

“My friends are assholes. Now get a condom, fucking put it on, and then fuck me till I can’t walk straight just like you promised me.”

“My pleasure.” Dean grunted fishing a condom out of the drawer. He made a show of tearing the wrapper open with his teeth, waggling his eye brows at Y/N. She scoffed.

“Quit bein’ a show off.”

Dean chuckled, quickly rolling the condom down his cock. He leaned down, and kissed her hard. Their lips were red, and swollen from the kissing they had done earlier in the evening. Dean nipped at her bottom lip, pulling away, and kissing along her jawline.

“You ready for me sweetheart?”

“Fuck, Dean. Yes.”

“I dunno. Maybe I should check.” He smirked against her skin, lowering his hand down to her cunt. He slid his index finger through her slit. “Fuck, baby, you’re practically drippin’ for me aren’t you?”

“God, yes Dean. Fuck me, please.” Y/N would never admit it, but it was definitely a whine.

“I’m gettin’ there sweetheart, I’m gettin’ there.” Dean gripped the base of his cock, and lined himself up with her cunt. He slowly pressed himself in, allowing Y/N time to stretch, and accommodate to his girth.

“Oh fuck. Fuck, Mr. Smith!” She cried when he was fully inserted into her.

“Fuck, call me that again.” Dean demanded.

“Fuck me, Mr. Smith.” Y/N grinned up at her boss.

“Fuck, Y/N.” He set up a fast rhythm, the dirty sound of skin against skin filled the room. “I’m not gonna last long like this sweetheart.”

“Fuckin’ come Dean. Do it.” She reached a hand down, and started rubbing her clit. She was reaching that cresting point just as teams rhythm turned erratic, and then stilled completely.

Y/N smiled, and wrapped her arms around his neck as he rested his forehead against her neck. Dean finally looked up at her, smiling in the afterglow of orgasm.

“That was amazing.”

“Good.” She pressed a kiss to his cheek.

“Did you…?”

“No, but it’s alright.”

“No it’s not.” Dean grunted pulling himself from her arms, and tossing the used condom into the trash. He kissed neck, then along her throat, then down her body before he settled himself between her legs.

He kissed along her thighs, working his way to her core, where she was practically aching with her need to come. When he decided he’d had enough with teasing her, he descended on her like a man starved. He ran his tongue along her slit, dipping it into her opening, teasing her with the pressure of his tongue.

She bucked into his mouth, wanting, needing, more.

“Fuck, Dean. I’m close, I’m so fucking close.”

He finally took pity on her. She settled his mouth over her clit, and began to suck, and lick it, at the same time he slid two fingers inside hooking them to rub against that spot inside of her that made her see stars.

“Fuck!” She screamed thrashing against his mouth finally coming undone. Dean helped her ride through the waves, and pulled away once she stilled completely. Her chest heaved as she tried to get her breath back.

Dean sat up smirking, wiping the back of his hand across his mouth. “How was that sweetheart?”

“Amazing.” Y/N sighed.

“Perfect.” Dean fell face first into the pillow beside her. “I’m stayin’ here for the night. Don’t think I could move even if I wanted to.”

Y/N chuckled, turning to get more comfortable. “Fine with me.”

Chapter Text

The first thing that crossed Y/N’s mind when she woke up was ‘thank God it’s Saturday’ the second was ‘I have a horrible hangover’. The third thought didn’t occur until she registered the weight in her bed, and the sound of light snoring beside her. The third thought? ‘Oh fuck, I fucking fucked my boss.’


“Fuck” She grunted squeezing her eyes shut tight at the bright light coming from her window. She stumbled up from the bed, and over to the window yanking the curtain shut.


“Fuckin’ hate the fuckin’ sun.” She grumbled falling back into the bed, ignoring her sleeping boss for the time being. Then he wrapped his arm around her shoulders, and nuzzled his face into her neck.


“Thanks, Lis.”


She gasped in anger, and pushed Dean away sitting up, and wrapping the comforter around herself. Dean barely had time to catch himself on her nightstand before he hit the ground.


He pulled himself up, resting an arm on the bed, and glaring at Y/N.


“What the fuck?”


“You fucking called me another woman’s name you asshole!”


Dean’s eyes widened. “Shit.”


“Yeah. Shit is right.” Y/N folded her arms across her chest. She looked to the alarm clock on her dresser, it read 11:15. “It’s almost noon. I’m sure Lis is gone by now, so why don’t you go home.”




“Go home Mr. Smith. Please.” She hissed. Dean sighed, knowing when he was defeated, and began to gather his clothes, and dress himself.


“I’ll see you at work Monday.” He said, hesitating in the doorway.


“I’m gonna be sick Monday. And Tuesday. It seems I’ve suddenly come down with something.”


“Y/N c’mon, don’t do this to me.”


She glared at him once more. “I’m sorry to inform you Mr. Smith that I’ve suddenly become ill, and will not be able to make it to work Monday, or Tuesday. I’m very sorry sir, have a good day.”


Dean was suddenly struck with the thought ‘if looks could kill’. He sighed, knowing that giving up was better in this situation. “Very well Y/N. Get better soon.”


She was right. He really did have shit luck with the ladies.





She was contemplating calling into work when Wednesday rolled around. She had a lot of vacation, and sick days saved up. But she knew that she would have to face Dean at some point. So she sucked it up, donned the typical pencil skirt, and matching blouse, and drove to work.


She was always there before Dean, it was her job to be. She had to have his schedule for the day written for him by the time he got in-who he was meeting with, what time to expect important phone calls, etcetera, etcetera,


So when she got to work that morning to find not only the biggest, and prettiest bouquet of flowers she had ever seen in her life, there was also a large container of her favorite chocolates. She wasn’t stupid, she knew this was Dean trying to get back in her good graces. After all, nothing like a pissed off assistant to really make your life shit.


She noticed Dean’s door was cracked open. Sighing, she sat her purse down underneath her desk, and hung her jacket over her chair, then made her way into Dean’s office.


“Good morning Mr. Smith.” She spoke. He looked up from his laptop, a smile spreading across his face.


“Y/N, thank God. It’s been hell here without you.”


“It’s been two days sir.”


“Did you see the gifts on your desk?” He asked, his expression hopeful like a child’s.


“Yes, I did. You didn’t need to do that.” She folded her arms over her chest, and leant against the door frame. Dean stood, and walked over to her.


“Yes I did. Look, it was stupid of me to…do what we did right after I had been left by Lisa. But Y/N you got to know that that was a slip up. I didn’t mean it.”


“Trust me, I know that entire night was just one huge fucking mistake.” She scoffed.


“No!” Dean insisted, “That’s not what I meant. I meant having done what we did so quickly after Lisa left me was a mistake. Look…could you, and I start over?”


Y/N looked away, “It’s not a good idea. There’s a whole chapter on why inter-office relationships aren’t supposed to happen in the freakin’ manual.”


“Oh please, like anyone follows that rule? Mr. Adler’s wife was his assistant before they got married, and she kept working for him for years after they got married.”




“Let me make it up to you. Let me take you out to dinner, or a movie, or…somewhere.”


“I’m not gonna be your fucking rebound!” She yelled. Dean stepped back from her in shock. “Your fiancée fucking left you like five days ago, and you’ve already fucked your secretary, and asked her out? No wonder you have such bad luck with women; you’re always moving on to the next piece of ass that looks your not even a week after your last girl leaves you!”


“Y/N I swear, that’s not what you are. You are not a rebound.”


“Yeah fuckin’ right. Look, I have work to do, and so do you. Now if you don’t mind, I’m goin’ to get started on it.”





“I’ve missed you here for the last couple days.” Sam smiled as he walked up to her desk.


She looked up from her computer, smirking at him. “You shouldn’t be spending your coffee breaks coming to visit me Wesson. I’m a busy woman, can’t afford to be distracted.”


Sam chuckled. “So where were you?”


Y/N sighed, “I had some shit to deal with. Needed a couple days to myself you know?”


Sam nodded. “Yeah I get it. Hey, so I have tickets to Watchmen tonight, and I know you’re into the superhero stuff…so if you wanna go…”


Y/N chuckled, “You’re a persistent bastard, Wesson; I’ll give you that.”


“Is that a yes?” Sam smiled all dimples, and puppy dog eyes.


“What’s going on here?”


Sam stepped away from Y/N’s desk as Dean stepped out of his office.


“Nothing, Mr. Smith. Just chatting with a co-worker.”


“Last I checked Wesson, you worked in I.T. That’s a different department, so Y/N isn’t really your co-worker.” Dean glared.


Sam stood to his full height. All muscles, and intimidation, even in that ridiculous yellow polo. “Well, last I checked Smith it’s my business who I talk to, not yours. And I’m sure it’s the same when it comes to Y/N.”


“Sam was just asking me out on a date, and I was just saying yes, Mr. Smith. That’s all, he’s leaving now.” Y/N smirked at Dean, knowing she’d just hit a nerve. She looked back to Sam, watching as a smile spread across his face. “What time is the movie?”




“Pick me up at my place at six. I’ll text you my address later.”


“Alright. Can’t wait.” Sam grinned, and walked away.


Dean placed his hand on her shoulder, “Y/N, can I see you in my office, right now?”


“Actually sir, I’m busy right now replying to your e-mai-”


“It wasn’t a request” Dean growled, and yanked her up by her arm, taking her into his office. He closed the door behind him, and pushed her into the center of his office making sure to block the door from her.


“Goddamnit Dean! What is your problem?” Y/N snapped, fists balled up in anger.


“My problem? My problem is you just said yes to that I.T. fuck right in front of me!”


“I’m not yours!”


Dean smirked, “If you honestly think that then you must’ve missed the part where we said we’ve wanted each other since day one.”


“I was drunk, and you were drunker.”


“We both know that you’re just making an excuse right now. Y/N you don’t want to go on a date with Wesson.”


“I don’t? Then pray tell, what do I want?” She folded her arms, and stood straighter trying her best to look intimidating.


“You want to get bent over my desk, and fucked like the whore you are.” Dean strode over to her, and gripped the back of her neck in one hand, and her hip in the other pulling her body in close to his.


She gasped placing her hands against his chest trying to find some space to just breathe. It was so fucking hard to breathe when he was this close to her, teasing her.


“I’m not a whore.”


“Only whore’s let their bosses fuck them.” Dean’s hand slid down to the hem of her skit, slowly hiking it up so that he could place his hand on her ass. “And I think you’re going to let me fuck you again. Bent over my desk. Just like I told you.” He pressed his face closer to hers their noses practically touching, from here she could count all of the freckles on his face.


“Mr. Smith….” She breathed, he smirked, finally closing the gap, and kissing her. She fastened her arms around his neck trying to pull him in closer. He pushed her skirt up to her waist, and tugged her panties to the side so that he could run his finger along her.


“You wet for me sweetheart? Been thinkin’ about this all day? Cause I have.”


“Fuck, Dean. Just fuck me, and get it over with already, I can’t take this shit right now.”


“I don’t think so Princess, I think I’m gonna take my time with you.” Dean chuckled right into her ear, sending a shudder down her spine.


“You have a meeting with Mr. Novak at one. It’s twelve-thirty now.”


“Plenty of time.” Dean grunted, pushing Y/N over his desk. It was always well organized, just a computer, an in/out box, and his name tag on it at any given time. The wall behind his desk is where he hung his pictures, and degrees.


She heard the moment Dean unzipped himself, but it still surprised her when she felt him press against her.


“Fuck, Dean. Do it, do it now.” She whined, as he pulled her underwear down letting them fall to her ankles.


“I don’t have a condom sweetheart, what do you think I should do?”


He was teasing her at this point. Legitimately teasing her, and she didn’t like being teased.


“How about, I eat out that sweet pussy of yours, and when I’m done you get down on your knees, and put that pretty mouth of yours to good use?”


“God, yes, please.”


Dean sat down in his chair grabbing Y/N’s hips. “Turn around sweetheart, and sit on the desk.”


She sat herself on the desk facing Dean; he scooted his chair in, and pulled her legs, pulling her panties off the rest of the way, and dropping them under his desk. He hooked her ankles behind his shoulders.


“Lay back Y/N. You won’t fall.”


She laid back, and pulled the hem of her skirt up again. The first touch of Dean’s tongue to her aching cunt had her head lolling back as she tried not to make too much noise.


“Who knew eating girls out was your second job.” Y/N chuckled. Dean pulled away his chin, and lips slick with spit, and Y/N’s own wetness.


“Sweetheart, eating pussy is my first job. And my favorite.” With that said Dean once again took to licking her like his life depended on it. He slid his tongue inside her, and she groaned. He pulled his tongue from inside her, and slid it up until it flicked across her clit lightly. She squealed.


“Fuck!” She cried, her hips jerking. Dean pulled back to look at her, that smirk still on her lips.


“Maybe I should make you wait. Get you all wet, and needy for me. Make you beg for me to fuck you.”


“Dean, please! Fuck, I need it” She groaned.


“I’ve got you Y/N.” Dean smiled, finally taking pity on her. He stood up, and leaned over her body so that he could kiss her, while his fingers went to work on her clit.


“Shit!” She gasped, hips jerking again.


“You’re mine aren’t you Y/N?” Dean breathed, looking her right in the eyes.


“Oh, God, yes.”


“Are you still gonna go on that date with Wesson?”






Her entire body tensed beneath his fingers working over her, and then suddenly she was coming. The pleasure washed over her in ways, as her walls rhythmically clenched around nothing, wanting something inside her so badly. Dean pulled his fingers away, shiny with her slick.


She sat up, trying to catch her breath as her heart pounded in her chest. A crooked smile found its way across her face. “I think you mentioned something about me putting my mouth to use?”


“I think I did.” He smiled back.


“Have a seat Mr. Smith. We have business to discuss.”


“Of course Miss.” Dean sat himself down, spreading his legs wide to let her in between them.


She gripped his cock taking the head into her mouth, just as there was a knock on the door. She knocked her head on the edge of the desk as she tried to stand; Dean pressed her shoulders down.


“Get under the desk!” He hissed, scooting the chair in so he couldn’t be seen from the waist down.


“Come in!” Dean called.


“Hello, Dean.”


“Hey, Cas.” He called.


Y/N cursed. She had lost track of the time, Mr. Novak was here for his meeting with Dean. Now she was stuck down here until the meeting was over, with her boss’s erection in her face. How had this become her life?


They began to talk business, Y/N didn’t bother to pay attention to it. It was always boring talk about sales percentages. It never interested her. Not even a few minutes into the conversation, Dean’s hand cupped the back of her neck urging her closer to his cock.


Her eyes widened, there was no fucking way he wanted her to suck him off while he was talking with his friend, and co-worker. But he didn’t let up, the tip of his cock pressing insistently against her pursed lips.


She pinched his thigh, his knee’s banging against his desk.


“Are you alright Dean?” Castiel asked, concern clear in his voice.


“Yeah, Cas. Just uh…a muscle spasm. I had a really rough work out earlier, and just…uh yeah. I’m fine.” Dean assured. He gripped her neck harder, and she rolled her eyes. Fine, she thought, why the fuck not.


She took his cock into her mouth once more, focusing on the head, as she wrapped her hand around his shaft, jerking him.


“By the way Dean. I noticed Y/N wasn’t at her desk. Is she still out sick?”


“No she came in today.” He grunted gripping her hair tightly. “I sent her to an early lunch.”


“Oh. Well I’ll let you get back to work, we can meet at Harvelle’s tonight for drinks, and catch up some more.”


“Sounds good.”


Dean waited until the door clicked shut behind Castiel before he pushed himself away from his desk.


“Fuck, Y/N. I could barely keep it together with you down there!” He snapped. She smirked taking him into her mouth one final time, just holding him there as she jerked him to completion. She released him, his cock twitching against his stomach having nothing left to give.


“I have the greatest assistant ever.” Dean huffed, leaning back in his seat.


“Look Dean. I have some rules I wanna set.” Y/N stood up, her knees aching from having been kneeling on the floor so long.


“Sure Y/N. Anything.”


“No more of this you own me shit okay? It’s all starting to get a little too 50 Shade of Grey for me to be honest. I know you’re a good guy, and all but we need a few rules.”


“Of course.” He agreed.


“No more fucking in your office in the middle of the work day understand? I wanna keep my job. No more sucking your cock when there are other people in the room, that’s fucking too much for me.”


“Anything else?” Dean asked, an amused smirk settling on his features.


“I’ll think of it as we go. In the meantime you should get back to work Mr. Smith, and so should I.” She lowered her skirt, and headed for the door.


“Oh Y/N?” Dean called, she turned to look at him, hand on the door handle. He held up her panties, her eyes widening at the realization. “I’m just going to hang on to these alright?”


She shook her head, “You’re a dirty bastard Mr. Smith. I like it.” She left his office closing the door behind her, and getting herself back to work.

Chapter Text

“This is a really fancy place.” Sam whispered across the table.


“Oh, well nothin’ but the best for you.” Y/N winked.


Sam chuckled, “Seriously though? How could either of us possibly afford to eat lunch at a place that has a freaking dress code?”


“Well, for my last birthday Mr. Smith gave a voucher to have a meal…or date here. He’s a member of the country club, so basically the voucher just bills it to his personal account, and then he takes care of it.”


“He’s really nice to you isn’t he?”


“Mr. Smith? Yeah, he is.” She smiled. “So uh, sorry about canceling on the movie.”


“I think you did me a favor, this is a thousand times better than some nasty movie theater. And neither of us is paying for it, I can get behind that.” 


Y/N shook her head. “I’m really startin’ to like you Sam.”


He grinned. “You called me Sam. Not Wesson.”


Y/N rolled her eyes. “Shut up Wesson.”

“What do you say we get us some lunch before we tee off for the back nine?” Mr. Adler asked, looking to Dean beside him in the golf cart.


“Lunch would be great” Dean agreed offering his boss a smile. This hadn’t just been a social call, he had been planning on discussing with Mr. Adler his long overdue promotion to head of sales, and marketing. It was early Saturday afternoon, and it seemed the country club was packed with people. 


“Would you like to sit at the table, or the bar?” Mr. Adler asked.


“Whichever you’d prefer is fine with me Sir.”


“Table it is.” Mr. Adler hailed a waitress, and they were being led across the dining room. Dean found himself looking around at the people dining, as they were led to Mr. Adler’s reserved table. Suddenly his eyes caught on two familiar faces just as the waitress stopped them at the table. She left them with menu’s, and a promise to be back in a few moments.


“What’s caught your eye Smith?” Mr. Adler smirked. Contrary to what most of his employees knew about him, the man was the sweetest man ever, and a total romantic at heart.


And when he took an interest in an employee, it was only inevitable that he took an interest in their romantic life.


“Uh...nothing sir.” Dean shook his head, trying to look away from Y/N, and Wesson. Mr. Adler just shook his head, and followed Dean’s gaze.


“Oh. Isn’t that your assistant? What’s her name again?”




“Right, Y/N. Lovely girl. And whose that she’s with?”


“Just one of the I.T. workers at Sandover & Bridge.”


“They look like a happy couple.” Mr. Adler turned back to face Dean, a pleasant smile on his face. “And you seem like you don’t like that.”


“Excuse me sir?”


“Which one of them is it?”


“I’m not sure I understand what you’re asking me sir?” Dean finally looked at Mr. Adler, confused.


“Which one of them is it that you seem to be in love with? Y/N, or the I.T. worker?”


If Dean had been drinking his water, he probably would’ve spat it out right then, and there.


“Si-sir, my fiancee left me barely two weeks ago. I’m not really ready to jump back into the thing.”


“Of course not.” Mr. Adler smiled knowingly. “You should go over, and say hello.”


“Sir I do-”


“Go say hello Smith.” Adler insisted. Dean sighed, and stood. He strode across the dining room to where Y/N sat.

“So, you know how first kisses are usually really awkward?” Sam asked.


“Yeah?” Y/N narrowed her eyes playfully, challenging him.


“Yeah. So I was thinking we could just you know...get it out of the way, make it less awkward.”


Y/N rolled her eyes. “If you wanna kiss me Wesson, just do it already.”


“Well, if you insist.” He grinned, sliding across the booth seat to get closer to her. His large hand practically engulfed her cheek, holding her in place as he leaned down slowly to place a gentle kiss against her lips. She gripped the lapel of his suit jacket, tugging him in closer, trying to get more from him. He smiled against her lips.


“Y/N, I’m really not that kind of girl.”


“Aw c’mon baby, I promise you’ll love it.” She breathed, playing along.


“Look, Y/N, I really like you.” Sam smiled, pulling away from her, he stayed close, draping his arm around her shoulders.


“I like you too, Wesson.”


“That’s why I think we should try to take this slow. I mean...I’m still coming off a bad break-up, and I just...I don’t know what went wrong with her, but I know that we tried to do things to fast.”


Y/N nodded “I understand Sam.”


“Oh fuck.” Sam retracted his arm from around Y/N, and scooted away, leaving her confused.


“What?” She demanded.


“Hello Y/N.”


Her eyes widened as she looked up. “Mr. Smith! Wha-what are you doing here?”


“I’m here playing golf with Mr. Adler. What are you...and Wesson doing here?” Dean asked. She couldn’t tell if he was upset, or angry, or what. And that scared her.


“We’re here on a date Mr. Smith.” Sam answered.


“Is that right?” The look he gave Sam was condescending. 


“Yes. Sir. We’re here on a date.” Y/N spoke, her tone challenging.


Dean fixed her with a gaze that she couldn’t quite read. He seemed equal parts jealous, and angry, but there was also something more to it. Something she still couldn’t put her finger on. She didn’t like not knowing exactly what it was Dean wanted from her.


“Very well then. I’ll see you at work Monday.”


“Yes sir.”


They watched as Dean walked back across the dining room to where he was seated with Mr. Adler.


“Holy shit, I thought he was going to kill me.” Sam finally spoke.


“So did I.” Y/N laughed, looking at him. “I’m really sorry about that. Mr. Smith is very...uhm protective of me.”


“Protective? More like possessive.” Sam shook his head, and adjusted his jacket. “Seriously what the hell is his problem?”


Y/N shrugged. “If I knew, I’d do something about it. So uh...are you ready to go?”


“After that? Yes.” Sam scooted his way out of the booth, and waited for Y/N. She followed suit, pulling her phone from her pocket as she felt it vibrate.


My apartment. Tonight. 8 pm.


“Who is it?” Sam asked, offering his hand to her.


“Just my mom checkin’ up on me. I told her about our date, and she just can’t wait for the details.”


Her phone buzzed one more time, and she looked back down at it.

Don’t be late.

She didn’t know why she was there. It’s not like she needed to go to his apartment; he wouldn’t fire her. At least she thought so. She at least hoped Dean had managed to understand that their relationship-whatever it was at this point-didn’t need to bleed over into their work relationship.
Still she showed up, 8pm on the dot. She knocked on the door, and a moment later it opened. Dean stood there, only his towel around his waist, hair, and skin still wet from his shower.


“You’re early.”


“I’m on time.”


Dean leaned back to look at something, probably a clock. “So you are. Come in.” He stepped back, opening the door wide to allow her in. She’d been to his apartment before, but the last time had been for a party that he had thrown to impress the higher ups. It had just been work, she had been there to make sure everything went smoothly for him.


“Dean, about earli-”


“Have a seat in the living room. Let me go put something on, and then we can talk.”
She sighed sitting her self down on one end of the ‘L’ shaped couch that took up his living room, watching as he headed down the hall towards his bedroom. He emerged a few moments later, wearing jeans, and a plain black t-shirt. Y/N had never seen her boss in anything other than a suit, and she couldn’t keep herself from thinking that she really really liked this look on him.


“So Y/N. Why do you think you’re here right now?” Dean demanded, treating this like any situation in the office. Taking control, asserting himself. Being dominant. She really needed to stop being turned on by this crap, it was ridiculous. 


“Because I went on a date with Sam.” 


“Good girl. And do you know why it may have upset me that you went on a date with him?”


“Because I promised you I wouldn’t.”


“We’re two for two sweetheart. Lets see if we can go for three. Why shouldn’t you have gone out with Wesson?”


“Because I’m yours.”


Dean clapped. “We have a winner.”


Her face burned with embarrassment. She was a grown woman for fucks sake, and she could do whatever she damn well pleased, and yet here she was feeling like a child being scolded.


“You talked about rules last week.” Dean began, “I think it’s time I set my own rules.”




“Yes. They’re simple don’t worry.”


She finally managed to look at him, that stupid smug smirk on his face. “Your rules were no sex in the office, or with anyone in the room. I can live with that. My rules however may prove to be more of a challenge, and if you don’t like them...then you’re free to end this...whatever it is. I won’t hold it against you. You go back to being my assistant, and I go back to being your boss.”


“Alright? What’re your rules?” She asked warily.


“There will be no one for you but me, and there will be no one for me but you. No more Wesson, he’s out of your life completely.”


“Anything else?”


“Never lie to me. You lied about not going out with Wesson. I don’t like being lied to.”


“And I don’t like being treated like a child!” Y/N hissed.


“Then stop acting like one!” Dean snapped back. “You tell me one thing, they go behind my back to do another. I don’t like that!”


Y/N took a deep breath, and nodded. “Fine. Fine. You’re right. Is there anything else?”


Dean sat back, looking at her, studying her. “The next part is completely optional...but something I would like you to consider.”




“Move in with me.”


“I’m sorry, it sounded like you just asked me to move in with you.”


“Like I said, it’s optional. I just want you to consider it.”


Y/N exhaled the breath she had been holding, and nodded. “Is that it then?”


“That’s it.” Dean nodded.


“Can we have make-up sex now?”


Dean chuckled, and held out his arm in invitation. “How about instead we just sit here, watch a movie. Maybe go to bed early?”


Y/N smiled, “Yeah. I like the sound of that.”


Chapter Text


Y/N hummed to herself as she organized the papers on her desk. Currently her boss Cain Faris, was having a meeting in his office with some young up, and comer at Sandover, and Bridge. Suddenly the door opened, and Cain led a young man out.


“I look forward to working with you Mr. Smith.” Cain smiled, shaking the man’s hand.


“I look forward to it too.” Mr. Smith smiled brightly, and Y/N couldn’t help thinking to herself that he was handsome. Bright green eyes, soft lips, and a strong jawline. He looked over, and saw her.


“And what would your name be sweetheart?”


Y/N blushed, and looked away, chastising herself for being caught staring.


“This is my assistant Y/N.” Cain stepped over to Y/N placing a hand on her shoulder. “Without her, I’d be lost.”


“He’s kidding, I’m just an assistant.” Y/N shook her head.


“Nonsense, Y/N is one of the hardest workers here at Sandover, and Bridge. She just won’t admit it.” Cain rubbed his thumb into her shoulder in a comforting manner.


“Maybe I’ll just have to steal you away from Mr. Faris then.” Mr. Smith chuckled. He said goodbye once again, and headed for the elevator.


“Y/N, could I see you in my office?” Cain looked down at her, a smirk playing at his lips.


“Of course sir.” She smiled, heart racing.


She followed him into the large office. It was sparsely decorated with a large glass desk in the center, matching chairs, and a few potted plants. Otherwise the office was very utilitarian.


“Lock the door please Y/N. It would be a shame if anyone bothered us.” Cain called, as he seated himself at his desk.


“Yes sir.” She turned the lock, and turned to face her boss. He leant back in his seat, a serious look on his face.


“What a naughty girl you were, looking at another man when I was right there.”


Y/N mustered up the most innocent look she could, and pouted. “I’m sorry daddy. You know you’re the only one for me.”


“Nice try my sweet girl, but I know that’s a lie. After the way you fucked Mr. Novak at the Christmas party, I know all you want is a nice big cock to fuck you.”


She didn’t even try to hide the smirk on her face. “But yours is the best daddy.”


Cain undid the buttons of his suit vest. “Is it? Why don’t you come, and prove it to me?” He removed his jacket, followed by the vest.


“How do you want me to prove it daddy?”


Cain rolled up the sleeves of his white button down to his elbows. He scooted his chair out, “I think you know how I want you to prove it. Get me ready for you.”


Y/N fell to her knees in front of him, undoing the button, and zipper of his gray trousers, and pulling his cock out. It was already half hard for her as she took him into her mouth.


“I love your mouth.” Cain grunted, “I love the way you’re just always ready to suck me off.” Y/N hummed as she bobbed her head, the vibrations around Cain’s cock making him groan. He wrapped his hand in her hair, “My sweet girl” He praised. A few more moments, and he gently tugged her hair.


“Something wrong daddy?” She smiled.


“If I let you continue, I’ll never get to fuck you. And where would we be if daddy didn’t fuck you?”


“I’d be very sad.” Y/N breathed.


Cain smirked, and stood up. He turned Y/N around, and placed his hand on her back, pushing her down over his desk; he rolled her skirt up her thighs, bunching it around her waist.


“You didn’t wear panties today.” Cain noted, his voice deeper now.


“I did it just like you asked daddy. Does that make me a good girl?”


“You are far from a good girl Y/N. You have been very, very naughty as of late, teasing your poor daddy.” Cain’s hand rubbed over her ass, kneading the flesh. “And naughty girls get punished.” He raised his hand, and brought it down quickly against her ass. Y/N hissed, pressing her forehead against the cool glass of Cain’s desk.


“Good girl, not making any noise when we’re at work.” Cain praised, “But you’re going to have to do better than that if you want daddy to fuck you.” He brought his hand down hard again.


Y/N gasped, “Daddy, please, please fuck me daddy. I know I’ve been bad, but I need you. I need you so bad.”
Cain brought his hand down for a third time, and a fourth, and fifth time in quick succession. Each hit left Y/N a panting, writhing mess.


“How badly do you want me Y/N?”


“So bad daddy, more than you know.” Y/N whined. She watched as Cain pulled one of the drawers of his desk open, and reached for a condom.


Before she could prepare herself Cain had already sunk into her wet channel, thrusting hard, and fast. “Daddy’s very sorry, but we have to make this quick Y/N. I have a meeting with Mr. Adler in an hour, and as much as I would love to draw this out, I can’t.”


Y/N rested her cheek against the desk, a smile making it’s way across her face. “S’okay daddy.” She felt her release coming quickly anyway, she had been horny all morning. She loved it when Cain wore his three piece suits, and he knew it.


“Are you going to come my girl?”


“Yes daddy, I’m so close.”


“As am I. I need you to come now Y/N/.” Cain grunted, reaching his hand around to rub her clit. She keened, back arching as she came at the touch of Cain’s hand on her. He followed shortly after, stilling in Y/N completely as his climax hit him hard.


Cain pulled out slowly, rubbing Y/N’s ass gently. “Are you sore?”


“I’ll be fine.” Y/N looked at him over her shoulder.


“Regardless, I’m still going to rub some lotion in.” Cain reached into his open desk drawer for the lotion he kept there for such occasions. He took his time, making sure that the lotion was rubbed in completely. “Better?” He asked.


“Much.” Y/N sighed lifting herself off his desk, and pushing her skirt back down. Cain pulled her in quickly for a chaste kiss.


“I must be off to my meeting, I want you to head out to lunch alright?”


“Okay. Enjoy your meeting” She kissed him again. Cain chuckled.


“As much as meeting with Mr. Adler can be enjoyed. Now go.” he patted her ass gently, pushing her towards the door.


“See you later daddy.” She called, smirking to herself.


“You’re just begging for another punishment aren’t you sweet girl?” Cain muttered to himself, shaking his head as he watched her go. 


Chapter Text

“Mr. Novak! What a nice surprise to run into you.” Y/N smiled as she walked into the copy room with a stack of papers in her hands.


“Oh, Y/N.” He smiled back “We always seem to meet like this.”


“Isn’t this what you have an assistant for?”


“Samandriel is out sick for the next couple of weeks. He contracted mono while he was visiting family in Chicago.”


Y/N hummed. “That’s unfortunate, luckily he has such a kind boss.”


“You think too highly of me Y/N.”


“Nonsense, you’re a perfect gentleman.”


Mr. Novak smiled once more, and turned to look at the copy machine. “I’d get out of your way, if I could figure out how to make this thing work.”


Y/N chuckled. “May I?” She asked stepping forward, shoulder pressing into Mr. Novak’s arm in the cramped copy room.


Mr. Novak ran a hand through his hair in frustration, “By all means, please.”


Y/N pressed a few buttons, and finally the machine came to life accepting his papers, and spitting out copies. She turned to face him, “So how have you been Mr. Novak?”


“Please, Y/N, call me Castiel.”


Y/N’s face split into a grin, “If you insist. How have you been Castiel?”


“Quite well, and yourself?” He smiled back, “How is it working with Cain?”


“Mr. Faris? Oh, well enough I suppose. He’s nice for the most part.”


“Will you be at the Christmas Party tomorrow?” Mr. Novak asked.


“I was going to stay home actually, maybe head to my parents a day early. Why? Is there a reason I should stay?” Y/N smirked. They had been playing at this flirting thing for a few weeks, and it was about time they stopped beating around the bush.


“I can’t catch you under the mistletoe if you aren’t there.” Finally the copy machined stopped the wheezing copier noise to indicate it was done. Mr. Novak reached around her to grab his stack of papers. “Hopefully I’ll see you there Y/N.”


She watched as he walked away, tilting her head to watch his ass. “If I go to that party we better be doin’ more than gettin’ caught under the mistletoe.” Y/N muttered to herself as she turned to the copy machine.




“You showed up.” Cain noted as Y/N made her way towards her boss.


“Well, I was given a reason. Just thought I’d come, and say hello.” She looked him up, and down hardly containing her laughter. “So, was the Santa suit your idea or....”


“Mr. Adler said I’d make an excellent Santa thank you very much.” Cain looked away, trying to maintain what dignity he had left.


“Uh huh, you look good in red...and fat.”


“It’s a pillow.” Cain patted his extended belly.


“I can’t believe you actually agreed to this, and I can’t believe I almost missed it.”


“Mr. Adler asked me to, and everyone kno-”


“Knows you can never say no to Mr. Adler, yeah, that’s why I’m your assistant remember?”


“Why did you show up?” Cain asked.


“If you must know, Castiel, and I have plans.”


“Castiel? You mean Novak?”


“Yeah, so?”


Cain shook his head, “You’re a grown woman Y/N, it’s none of my business.”


“You’re right. It’s not. Now if you’ll excuse me sir, I am going to go find him.”


“Maybe I’ll see you later in the evening; you could even sit on Santa’s lap” Cain smirked.


Y/N snorted, “Yeah, you wish old man.”




“I have been looking for you all night” Y/N huffed as she finally came to stand beside Mr. Novak at the table full of food, and drinks.


“Y/N! I thought you weren’t coming!” Mr. Novak smiled at the young woman.


“Well you did say something about me, and you under some mistletoe, so here I am.”Y/N smirked.


Mr. Novak choked on his drink, trying not to spit it everywhere; he looked at Y/N face flushing red. “Y-you’re serious?”


Y/N’s face fell, and she began to talk quickly, trying to disarm the situation“Well, I mean, if you don’t want to...I just-just thought you were flirting with me, and that maybe you wanted-”


“No I-I was flirting, I ju-just thought that you weren’t interested in me!” Mr. Novak finished, face still red, and looking quite uncomfortable.


“Of course I’m interested in you. Freakin’ look at you, and you’re like the sweetest guy I ever met. Why wouldn’t any girl want you?”


If it was possible Mr. Novak’s face seemed to get redder, “Because I uhm....I like certain the bedroom.”


“What? You’re kinky? I like kinky.” Y/N smirked, finding her confidence again. Kink was something she understood, she had a few of her own.


Mr. Novak looked down at his feet, trying his hardest to avoid eye contact. “I-I’m sorry Y/N, I don’t think I can do this.”


She reached out to take his hand, when he looked at her she smiled softly, “Lets go to your place yeah?”




“This is what you were worried about? Seriously?” Y/N asked incredulously. They were both at Castiel’s apartment-a nice penthouse in one of the many tall buildings downtown. They had very quickly ended up naked, and in his bed with her straddling his waist as he laid beneath her.
Castiel turned his face into his pillow, “Y/N, can’t you at least pretend to understand why this would be embarrassing for me?”


“What? You like chicks to fuck you with a strap-on? So fuckin’ what? It doesn’t make you gay if that’s what you’re scared of, and it doesn’t make you less manly. It just means you like gettin’ fucked up the ass.” Y/N grabbed the harness, attached to it was a realistic dildo, about six inches long, and not very wide. Inside the harness was an even shorter plug in the center of it.


“If...if you don’t like that one, I also have one without the... you know; I just thought you might....”


“It’s fine, Castiel. Are you sure you want to do this? I can tell you’re...having some sort of issue right now.”


Castiel chuckled, finally looking Y/N in the eyes. “I’m not having an issue...I’ve just never met a girl who was as okay with this as you are. I mean the girlfriend who introduced me to it was pretty into it, but she was also pretty’s just refreshing that you’re so calm.”


“I’m glad you think so, cause now that we’re this far I really wanna fuck you.”


They both laughed, and Y/N was more than happy to make Castiel more comfortable if this was what it took.


“Alright” Y/N clapped her hands together, “You ready, and I’ll get this thing on.”


Castiel smiled wide, the space by his eyes crinkling. Y/N scooped up the harness, and one of the bottles of lube Castiel had provided, and headed into the bathroom. When she came back out the harness was tightened, and fitted just right so as to not pinch her skin; the sight that greeted made her jaw drop, and made heat pool in her gut.


Castiel was laid out on the knees up, and his legs spread wide as he opened himself with his fingers gasping, and huffing. His cock laid half hard against his stomach; the tip just beginning to glisten.


“Holy shit that’s hot” Y/N all but groaned as she placed a hand against her stomach, and the frame of the bathroom door to keep steady.


Castiel chuckled, pulling his fingers away from his hole. He scooted up the bed to make himself more comfortable against the pillows. “Are you ready?”


“After watching that? I’ll be ready for the rest of my fucking life.”


“Only you can make a man blush like a school girl,” Castiel shook his head, the smile on his face affectionate. Y/N just chuckled, and climbed on to the bed, she again straddled


Castiel her own fake cock laying beside his as she pressed a kiss to his lips. Barely breaking from Castiel’s lips for longer than it took to take a breath Y/N reached for the lube, and slicked up the dildo.


“Are you ready?” Y/N panted, gripping the fake cock tight in her fist.


“God, yes.” Castiel grunted. Y/N pressed the head of the dildo to his hole, and slowly pushed in. When she was fully seated into Castiel, she looked down at him, and grinned wolfishly.


“I’m kinda liking the view here,” she reached out to give his cock a few tugs that had him gasping, and twitching underneath her.


“Fuck, Y/N, you have to move please!” Castiel begged, trying to push back against her.


She griped his hips, and set a slow rhythm. Castiel threw his head back with one thrust, baring his throat to her; she pressed her lips there working her way over his neck, and jaw as she kept up the slow rhythm.


“Fuck, Y/N please.”


“Please what?” She whispered in his ear.


“Go faster, turn on the vibrator, just do...something more!”


Y/N dead stopped, drawing a confused whine from Castiel. “This thing fucking vibrates too?”


Castiel couldn’t help but snort at her own confused tone. He reached for her hips, and easily located a wired box that had been attached to the back of the harness. He flicked the switch to a high setting that had Y/N keening.




“Is it too high?” Castiel asked. Y/N shook her head.


“Fuckin’ perfect, Jesus Christ.” She muttered as she started her rhythm again. She didn’t know how much longer she could keep this up, so she reached for Castiel’s cock, and jerked him.


“Fuck, fuck!” Castiel shouted, arcing off the bed as he painted his chest with his release. Y/N gave a few more thrusts to help Castiel ride out his own orgasm as hers finally overtook her. She pressed her forehead to Castiel’s chest as her thighs began to tremble with the sensation overload. Finally the vibrator shut off, and she let out a breath she didn’t even know she’d been holding in.


Y/N gripped the base of the dildo, and slowly pulled out of Castiel, finally collapsing beside him on the bed.


“Fuck, that was awesome.” Y/N sighed.


“I’m glad you thought so.” Castiel leaned over, kissing her softly then setting to work on removing the harness from her. “Maybe later I can fuck you.”


Y/N smirked, “Well that was what I originally came here for, so it would be a shame to leave before that huh?”


“I’ll try not to disappoint.”


“After that, I don’t think you can disappoint me.”


Castiel chuckled once more, “Just rest Y/N, I’ll be back in a few moments.” Castiel headed for the bathroom, and Y/N could hear the shower turn on as her eyes began to close.