Late Nights: Overtime with Sean

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Daniel spends more time with his boss Sean than expected.
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All Characters in this story are above 18 years of age.

"He smells amazing," Daniel thought, pressing his waist back into Sean's firm torso, making room as the others packed into the elevator, grinding gently against his crotch. He watched as the elevator passed floor after floor, biting his lip as Sean began thrusting lightly against his ass. Glancing around nervously, he made sure no one else paid attention as he rubbed his cheeks slowly along the bulge poking into him.

They were quiet the whole ride down, touching but ready to separate if someone caught on.

As the elevator arrived at the basement, Sean exited first, tracing his pinky across Daniel's hand before turning right and walking briskly to his car. Daniel watched him leave, eyes glossy with fantasies about the two of them together and how he would taste.

"How long are we going to keep doing this?" Daniel thought to himself while pulling out of the parking lot. Night after night, they worked together, and night after night ended the same. It was all he thought of from morning until bed.

Luckily, the wait would soon be over.

The Next Day

Subject: Overtime

Hi Daniel,

Layla called in sick earlier today, to meet next week's deadline I will need you to stay for overtime. Come visit my office at 4 and we'll sort out the details for later.

Regards,

Sean

Daniel's eyes lit up as he read the email, tonight would be only the two of them working together. He glanced over to Sean's desk where he was on the phone, fingers pressed against his temple, having a difficult conversation. Overtime was the last thing he wanted on a Friday, but when it came to Sean he was happy to make an exception. That would go for anyth--

"Danny!"

Daniel swiveled around to see Mark, glowering over at him, a stack of paperwork in hand. "Uh yea, hey Mark. What's up?" said Daniel. Mark shook his head "What's up? I asked you for these documents an hour ago and you're here fucking around as usual. What are you even doing?"

"Sorry boss, really. I think I just lost track of time, won't happen again I swear" said Daniel.

"You're right it won't, next time you'll be going home without a job. Get your shit together" said Mark before storming off. Daniel stuck up the middle finger to Mark's back as he left, "Dickhead" he thought.

Turning back towards Sean's office Daniel saw him watching from his desk, he felt his face turn a deep, flushed red, burning with embarrassment. Locking eyes he smiled nervously and mouthed, "I'm sorry" with a half shrug. Sean just shook his head and turned back to the pile of sheets that covered his desk,

"Real smooth, Danny, real smooth" Daniel thought to himself.

4 PM

Daniel saved the most recent update of the presentation being prepared for next week and transferred a copy to his USB. After logging out and grabbing his bags, he made his way over to Sean's office and knocked on the door.

"Come in!"

Daniel stepped into the office and saw him hunched over the computer, typing furiously on the keyboard. "Hey Sean, how it going?" he said as he hung up his coat and pulled out the new designs he had been working on earlier.

"Not good, I've been going back and forth all day with the Angelo's. I think they're ready to pull out" said Sean. He slumped back against his chair, closing his eyes and sighing deeply. "We've got to really knock it out of the park at our next pitch meeting or we can forget the account, and our monthly targets."

"Don't worry, we'll be fine. The teams working night and day, it's one of our best concepts to date, and we have Sean Stone leading with the magic touch," said Daniel smiling.

"Really? From what I saw between you and Mark earlier, looks like not much is happening and the "team" isn't really pulling together, you hear what I'm saying?" said Sean sternly. Daniel felt his stomach turn, he never knew with Sean. One moment a warm and kindly man, the next a pillar of stone, tough, cold and unwavering.

Daniel's eyes fell to the floor "I um... you're right. How I behaved was unprofessional and I should have handled the situation better". Sean stared him down "I don't really know what to do with you Daniel, I know you work hard, I see you staying late, I see a lot of potential but then I turn around and you're acting like this".

Daniel swallowed "I'm sorry, I don't know what to say. But from here on out I'll keep on top of it and anything you need, just say the word". He squirmed in his chair, this wasn't how he planned this meeting going but he felt ready to melt as Sean fixed his gaze on him.

Sean stood and faced towards the window, "Alright, whatever you say". Daniel eyed Sean up and down, older around 50, with a large belly stuffed into his pants, firm barreled chest, broad rounded shoulders like bowling balls that ran into a pair of meaty arms he dreamed wrapping around him. All dressed and packed into a fine, tight suit that bulged in all the right places.

"I have the designs you asked me to work on last week. If you'd like we—"

"To be honest Daniel I didn't ask you to come to talk about the project, I'm here to talk about you" Sean interrupted. "I'm going to be very upfront, I'm thinking about laying you off". Daniel's heart plunged, "Fuck, Fuck, Fuck" Daniel thought as he sat upright. He quickly responded "I am so sorry, Sean. Really, I'll do whatever it takes. I need this job, what am I—"

"Be quiet and let me finish, if you'll do whatever it takes then I need you to listen," said Sean. "I said I was thinking about it, it's not a for sure thing. And working together these past few nights have really shown me the quality of work you're capable of" said Sean.

Daniel felt himself blushing again; he was never great at taking a compliment. "Thanks, I appreciate it" said Daniel. Sean continued "But I've only seen you do this type of standout work on my assignments. When it comes to Mark, or Layla, or Donavon the quality plummets. Why is that?" he quizzed studying Daniel's expression.

"I just... I like working with you Sean. I learn a lot working together and I want to make sure to give you the best that I can," said Daniel looking softly into his eyes. "I remember you were the one to hire me and give me a chance, I always appreciated it and I've looked up to you ever since."

Sean's stare relaxed as he tried to fight back the starting of a smile "Well I'm flattered, and you are a bright kid. That's why I hired you, but I need to see this effort on all your work. Not just for me ok?"

"Okay" said Daniel smiling, fantasies floating in his mind.

"Now show me some of those designs you were talking about"

8 PM

The office was quiet and empty except for the light shining out of Sean's office window. They sat next to each other packing away the last their notes and discussing their approach for the client meeting. "I think you should start off the presentation after we finish introductions. You'll make a great first impression and I'll take any questions they might have" said Sean.

"Sure thing, I think this is one of the best projects I've gotten to work on and I'm looking forward to it. I'm going to miss working together once this is all over though," said Daniel. "I know. I never knew how well you could put together a pitch like this. I'm seriously impressed," said Sean.

Daniel beamed, feeling butterflies stir in his stomach and his heart beating its way out of his chest. Sean looked at him, his mouth opening and closing, ready to say something more. The office felt smaller and quieter than it ever had as they continued to gawk at each other.

"If we don't end up on anymore assignments, I want you to know you can come to me with anything Danny. I'm happy to help you out because I was serious before, you're a sweet kid, bright, likeable, and hardworking, I see a lot of potential in you." Daniel smiled and looked down at the floor nervously, "Thanks"

"That's why I took a chance on you, that's why I need you to stay around and cut out the silly crap like what happened with Mark earlier," said Sean placing his hand on Daniel's shoulder, sending a light shiver down his body.

Daniel swallowed and shifted closer "I know, and it's true. I'll make more of an effort to work with the others at the office. But, when it's you..." He looked up and saw Sean staring tenderly back. "I know," said Sean.

"Truth is, you remind me a lot of myself when I first started at this company," said Sean. "I had the drive and ideas but I was young, and it took finding a mentor to help get me on track," said Sean smiling and stepping forward, touching the tip of his shoe's to Daniel.

"And, that's why I want you, why I'm not letting you go" said Sean softly. Daniel took another step forward, smelling his aftershave and feeling his cool breath on his cheeks. "I see you the way you watch me at work," he said quietly.

With that, Sean leaned forward and kissed Daniel affectionately.

Daniel melted, pressing himself into Sean's beefy, strapping body as Sean slid his hand along his neckline, cupping his face and gently pulled him deeper into his embrace.

Daniel's arms rose up and along Sean's body until he was pawing at his pecs and slipping fingers through the buttons of his shirt to play with the chest hair underneath. He felt Sean wrap his other arm around him, caressing his upper back and tracing his spine down to his waist.

"Anything you want" said Daniel grinding his crotch against Sean's and feeling the man's considerable cock mashing back against his, threatening to rip through the pants that separated them. "I want this" said Sean as his hand slipped into Daniels waistband and gripped a meaty piece of ass cheek.

"Oh daddy!" Daniel gasped as his eyes closed while Sean gently nudged his middle finger around his asshole. Daniel could feel his dick leaking pre-cum, this was his dream every day and every night since meeting Sean.

He opened his eyes and saw Sean staring deeply at him, saw him thinking of a dozen ways to spread him open and make him moan. Daniel nodded, and without a word, Sean grabbed him and tossed him onto the table, knocking everything to the floor. The two continued to kiss as they ripped their belts off, unzipped their pants and threw their shirts to the side.

Daniel laid on his back, caressing Sean's body as their cocks slapped against each other, both leaking and sticking to each other as Sean continued to finger Daniel's asshole. "You're my sweet boy Danny" whispered Sean as he ran his hands down Daniel's thighs, parting his legs, revealing his soft, pink, butthole, wet and quivering with anticipation.

"Ohh, hmm. Fuck!" Daniel gasped as he felt Sean poke the head of his cock into his ass, his body twitching and whimpering as it moved deeper inside. He felt himself loosen as the rhythm of the strokes became more familiar and pleasant. He clung closer to Sean, giving himself over, a warmth overcoming him as he saw the hungry, adoring look in Sean's eyes.

Soon Sean was thrusting in and out with ease, running a tingle though Daniel's body each time he entered. Daniel nuzzled his face into Sean's thick body as his cock continued to slam into him, balls smacking against his ass and a feeling of fullness he never wanted to end.

A sudden spank opened his eyes as he saw Sean staring at him again, the sting snapping him out of his trance and sending waves of pleasure though his body. Daniel sent him a pleading look, asking him for more, biting his lip and trembling as Sean pounded against him.

"Oh daddy fuck me!" Daniel yelped as Sean clapped against his ass cheeks harder and harder. He closed his eyes and moaned as his asshole stretched, throwing his ass down, riding Sean's cock with each stroke, begging him to fuck him, harder, faster.

Sean pressed their foreheads together, tongues entwined as he smacked Daniel's beautiful, bubbly ass, jiggling with each spank. He felt his cock twitch and his balls starting to bulge; he started to speak before seeing Daniel looking at him, nodding, begging with his eyes. Sean couldn't hold back as the rich, thick cum burst out and poured into Daniel's ass, pumping and emptying into him.

Feeling Sean's hot load leaking out of his ass and the wet, hard cock deep inside him sent Daniel into orgasm as well. His eyes rolled back as cum spewed out of his cock, again and again with every pump, coating their bodies and mixing with sweat, making a musky scent that turned him on even more. His body twitched and had minor spasms as he wrapped himself around Sean, burying his face in his chest, feeling Sean stroke his head as the last few strands of cum leaked out of him.

They stayed like that, cuddling in cum, panting deeply before Daniel slid up to kiss Sean passionately. Staring deeply into his eyes Daniel whispered, "I think I love you". Sean giggled saying, "Stop it" before kissing him one last time. Slowly they put their clothes back on after Daniel used his underwear to mop as much of the cum off them as he could, throwing it into a garbage can.

After dressing, they grabbed their bags, flicked off the lights and made their way to the elevator. The doors opened and they hit the button for the basement, Daniel felt Sean wrap his arm around his waist, pulling him in and kissing his neck gently as he rested his head on his shoulder.

As the elevator arrived at the basement, Sean exited first, tracing his pinky across Daniel's hand before turning right and walking briskly to his car. Daniel watched him leave, eyes glossy with memory of the two of them together and the taste of him in his mouth.

"How long are we going to keep doing this?" Daniel thought to himself while pulling out of the parking lot. Night after night, they worked together, and night after night, he hoped it would end the same. It was all he thought of from morning until bed.

For now though, he would always think back to this late night with Sean.

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