Requested by dilflover24

Y/N sighed wistfully as she watched Dean go to the copy machine for what seemed like the millionth time this day.

"Why don't you talk to him about something other than the weather?" Teased Kate, her work friend.

Y/N groaned. "I can't! He's out of my league, for one thing."

"You have no idea how many other women here might wanna get him."

It was true, Y/N wasn't the best looking, but she wasn't ugly, either. Sure, she had had a few boyfriends here and there, but she felt like a nobody compared to Dean.

He had charcoal eyes, matching slick hair, and wore round glasses. He was also notorious for smoking.

Some of the people at work had complained about his smoking habits, but he'd done it outside anyway, so what were they whining about?

It never bothered Y/N that he smoked. Her dad and grandfather were smokers, but maybe she was used to it because of that.

And Dean was very respectful of everyone, very mysterious yet friendly. There was no way Y/N was more than a co-worker to him.

Kate smirked. "You want me to talk to him for you?"

"No! Please, don't do that."

Y/N covered her face, groaning. She then wrote a few things down on the sheets she needed to get to her boss that afternoon.

"Well, you better make a move."

"I don't even know how he feels about-"

"Hey, ladies. Y/N, can I borrow a pen?" Spoke a deep voice.

Y/N and Kate
looked up from their cubicle.

It was Dean.

He wore a black button up shirt, and matching pants. His sleeves were rolled up, showing off his impressive forearms.

"Oh, hi Dean! Yeah, sure, here." Y/N handed him a blue pen from her desk.

"Thanks, Y/N."

He took it with a smile, and then strode off to his cubicle on the end of their aisle.

Kate covered her mouth. Her eyes were glittering. "Talk to him, dang!"

Y/N grimaced. "Did you even see that? I could barely speak."

"He smiled."

"It was just a smile."

"He rarely even smiles. Go talk to him."

Y/N swallowed. "Just be yourself. And relax, you look like you're in a front of a firing squad."

Kate giggled.

"Ow!" She winced and Y/N smiled proudly. "I don't have a problem with approaches. Are you sure you don't want me to talk to him-"

"Yes." Y/N whispered. She glanced around, but everyone mostly had earphones in. She narrowed her eyes.

Y/N sighed and arranged her papers neatly. Then she smoothed her hands over her arms.

"I'll figure out something."

Kate rolled her eyes, but she turned back to her cubicle.

Y/N spent the rest of her shift writing, copying, and more writing before her papers were done for the day.

Her head and neck were aching, and she cracked her neck. A pop sounded throughout the room, causing a few heads to turn.

"My neck. I just cracked it. Don't worry." Y/N smiled, and some of them nodded.

She then realized Dean never gave back her pen he borrowed.

Her shoes clicked on the floor as she made her way to Dean's desk.

His area was very neat, all his papers stacked well. His laptop was closed, and he was writing furiously on a sheet, but what caught her eye was-

"You have pens of your own."

Dean turned around, the top two buttons of his shirt undone. Y/N swallowed.

"They're out of ink."

"Then why are you keeping them?"

Y/N pinched her arm subtly when she saw his eyes glint with alarm.

"(Boss's name) likes blue ink on the papers, remember?"

He wasn't wrong. Their boss for some reason and a fixation with blue ink. If you signed a paper, it had to be with blue ink.

She nodded, shrugging. "Well then. Can I have it back, please?"

He handed it over wordlessly.

"Hey, Y/N, Dean, are you guys going to the staff party tonight?"

This came from another coworker, Teddy. He was a twenty five year old man, who liked meeting people. He also tended to annoy some of them, but it was all in good fun.

"I might." Y/N said, "There's food, so why not?" She chuckled.

She quickly glanced at Dean to see if he would laugh, but he just smiled gently.

"I can't. I have too much paperwork."

"Bullshit, Dean. You always get your stuff done on time-"

"Oh, shut up." Dean gathered his stuff, playfully hitting Teddy's shoulder.

"Besides, I'm busy tonight anyways."

"Doing what?"

"None of your business."

"Come on, Dean!"

It was obvious that Y/N was out of the conversation, so she just excused herself and went back to her desk.

I don't think I'll get anywhere with him. He seems to just see me as a co-worker.

The rest of her evening was uneventful, knowing that Dean wouldn't be at the party.

Y/N sighed, glancing at the clock. It was only ten PM, and their parties seemed to go into the wee hours of the morning.

Kate had been texting her a few times to come along, but Y/N had kept refusing.

Finally, after what seemed like the longest mind battle, Y/N got up.

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"There she is!"

Cheers erupted when Y/N walked in, wearing a black wrap dress that fell to her knees. Stilettos tapped the floor, and she smiled at her co-workers.

The attire was semi formal, so everyone wore simple dresses and shirts.

Her boss had treated them all to a sushi restaurant. He wore a cream colored button up shirt, rolled at the sleeves.

Y/N smiled, glancing around for Dean. Eventually she spotted him. He was seated at the table, on the left side of-

Y/N swallowed.

Daria Ferris.

She was the secretary at work, and she was undoubtedly pretty.

Her long auburn hair curled against her skin. She wore a dark green sleeved dress, with lace details on the shoulders.

He was smiling and nodding as Daria spoke, about what, Y/N didn't know. But she sat down in an empty spot and sipped water.

I can barely speak to him, and yet here I am hoping I have a chance.
-------------------------------------------------

The sushi was amazing, and by the end of the night, everyone was full. Y/N spoke with Teddy and Kate, and a few of her co-workers throughout the party.

Her boss paid for the food, (even though a few had insisted they split it), but he'd been adamant about getting the bill and then slowly, everyone started to trickle out and go home.

Y/N dug through her bag, sighing in relief when she located her keys.

Even though she'd cleaned out her purse, it always seemed to get full again with receipts and other junk.

"Y/N?"

She glanced up to see Dean.

He stood with his hands behind his back, a small smile on his face. His glasses were shiny and polished.

"Yes, Dean? What's up?"

A tinge of red colored the tops of his cheeks. Y/N started to smile, but her heart skipped a beat.

Why is he suddenly so nervous?

"Could I get a ride home with you, please? If that's okay."

Y/N knew that Dean took the transit. He drove, but he didn't own a car, but he lived downtown, close enough to walk to work.

But it wasn't safe for anyone really, to be out this late.

Her phone's clock said twelve thirty AM.

"Okay, sure. Let's go."

The walk to the parking lot was quiet, with a bit of banter here and there. Y/N glanced at Dean once more.

"Like what you see?" He teased.

Y/N started. "I didn't mean to-"

Dean chuckled, smiling at her. "I'm kidding, Y/N. So there's something I've been wanting to talk to you about lately. "

She clicked the button on her keys. The front door unlocked and she nodded at Dean to come in.

He sat down in the passenger seat, glancing around.

"This is nice."

She shrugged. "Thanks. I bought it last year."

The weather on the backup screen said there's be a chance of rain tonight, but so far, only a few drops had splattered the windshield.

Y/N turned on the car, letting it warm up for a bit. "I've noticed."

She turned her head, brows furrowed.

"Noticed what, Dean?"

He smirked slightly, her confusion adorable. "That you've been staring at me. A few times. Is it so hard to say it?"

Y/N averted her eyes, heart racing. He gently grabbed her hand, and with his other hand he turned her head to him, so he was looking at her directly.

"Do you like me, Y/N?"

Of course he noticed. I think everyone knew. Dang it.

She swallowed quietly. "Yeah. Do you?"

He chuckled in disbelief.

"Remember today when I asked for a pen from you? And I later said mine were out of ink?"

Y/N's eyes widened, and she covered her mouth to keep from laughing out loud. "Oh, my God-!"

He looked away as Y/N giggled in realization.

That was an excuse!

He waited until she was done, mostly breathless at that point. "I like you too, Y/N."

They both grinned.

Neither of them had even put on their seatbelts, Y/N realized as she noticed how close they were leaning to each other.

Dean's breath stirred her eyelashes as he tipped his head to hers gently. "May I?"

As soon as she nodded, his lips were on hers, slow and hot.

She cupped his neck, shyly slipping her tongue into his mouth, tasting the champagne he drank that evening.

His palms smoothed over her dress, rucking up the hem when he pulled her to sit on his lap.

His faint groans were like music to her ears when she sucked and kissed at his neck, his fingers tightening on her hips when she sucked under his left ear.

"Right there-" he whispered, head thrown back against the seat.

Y/N smirked, feeling him under her. She pulled away, panting and smoothing her hair down.

"Are you sure about this?" She asked, suddenly very aware that they were in a parking lot.

He shook his head. "Yes and no."

"I'm sorry?"

He sighed and opened his eyes. Y/N felt a rush of pride when she saw how his eyes were glassy.

"I want this, I want you, but not in a fucking parking lot. Let's go to my place." He groaned.
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Dean's breath tickled her neck as she writhed against him, guiding his hand.

By now, they were both nude, his hard chest rubbing her shoulder as he leaned over her, propped on his side. His glasses were off, set on the bedside table.

She was throbbing, tightening around his fingers when he hit her sweet spot. "You're so beautiful." He murmured, leaving kisses of fire across her breasts.

With one final thrust, she grunted against his mouth, grinding on his hand.

He slowed, letting her ride it out, before setting her down against the sheets. "Just a sec."

He reached into his bedside table, pulling out a condom.

Y/N's chest was rising slowly, her eyes wide and glassy. There were a few bite marks and hickies across her chest and thighs.

She sat up slowly as he rolled it down over himself. "Can I?"

He clenched his jaw, wanting to get inside her before he went off. He could probably cum just like this, actually.

Regardless, he nodded, and she smirked when his hips jumped towards her hands when she finished rolling it down the rest of his length.

"Tease," he chuckled, before pushing her back against the sheets. Her eyes were wide and wild, a smile playing on her lips.

He wrapped his arms around her thighs and dragged her towards him, lining himself up. Never breaking eye contact, before he kissed her slowly.

Y/N whimpered. She cupped his face, her thumbs in front of his ears.

When she pulled away and put her cheek against his, her soft breath tickled his ear. "Dean. Hard, please."

With a growl he buried his face in her shoulder, pressing forward. Y/N immediately gasped, her back arching towards him as she took his length.

His fists were clenched so hard beside her head, his knuckles turned white. Even better than he imagined.

With a slow roll of his hips, he pulled his face away to watch Y/N. Her head was thrown back, eyes lidded with bliss.

He'd known she liked him, even before he said it. She was way too obvious, barely meeting his eyes, a small smile on her lips whenever she spoke to him. She always looked so happy to see him when they'd accidentally bump into each other at the office.

"Oh-oh, right there." Y/N purred, pulling him closer, her small gasps and moans in his ear better than any porn. Her fingers slightly twitched as she ground against him, scraping his shoulders.

Dean chuckled breathlessly, leaning down and kissing her deeply as he kept his pace, but she felt too good, that he could feel himself slipping faster than he'd like to.

Hell, if it hadn't been a while.

But he gripped her hips tighter and gave her hard thrusts, making her body bounce roughly, just like she'd said. Her ankles locked around his back and he nearly choked, the feeling in his lower abdomen rising in intensity.

"So beautiful like this, baby girl. You like that?"

On 'that' he gave an extra hard thrust, and she mewled, giving him a salacious stare. The pupils of her eyes were dilated, the irises just barely showing her (eye color). She groaned, dazed with pleasure.

"Please make me cum, Dean."

Well, that was it. With his own orgasm approaching, he grit his teeth, giving her what she wanted.

And then everything turned to white as he grit his teeth and shuddered, before rubbing at her clit with his thumb- "Like that?" He gasped, and she nodded frantically- "Yes, yes."  feeling her spasm around him, even as he was soft.

Y/N let out a sharp gasp with her high, rolling her hips against him beautifully.

He carefully sank down beside her on the bed, pulling the covers around them both. She gave him a shaky smile as she came down.

"I love the things you do to me," she started, and Dean smiled, touching her cheek.

"Well, I enjoyed it too." He replied, his heart nearly melting when she covered this hand with hers. "Did you mean the sex, or that we really like each other?" He winked.

Y/N laughed. "Both, thank you." She scooted closer, nuzzling his hand.

        He sighed softly before settling in, both of them in slumber and bliss.

*This is very unedited, but I hope I did your request justice!