Mixing Work and Pleasure

Jackson was having a miserable day at work. He’d lost his progress report and had to print out a new one before the meeting, only for the printer to jam. Then he got sprayed with ink when he tried to fix it, ruining his shirt. He’d gotten reamed by the boss during the meeting for being ‘unprepared,’ and unprofessional. It wasn’t fair. Robert wasn’t usually a bad boss, but those reports had been important and corporate was breathing down his neck about layoffs. He didn’t want to fire anyone, but he’d already been made to dismiss five employees. The stress was getting to him.

The rest of the day was uneventful, with Robert swearing up a storm in his office while Jackson just tried to remain invisible and get his work done. It wasn’t easy, but he managed… mostly. A few of the guys picked on him during lunch, but that was nothing new. As the only out gay man in the office, he was an easy target. Most of the time, he just shrugged it off, not caring about what they said. Something about today, however, had him nearly in tears as he shoved past them and ran to the bathroom. Their laughter echoed in his ears as he splashed water on his face, trying to force the thoughts away.

Robert paused when he entered the bathroom, frowning when he saw Jackson so upset. He knew what was going on. He had talked to the other guys before about leaving him alone. Seems they hadn’t listened. He washed his hands quickly and left the room, marching over to the employee lounge. He grabbed Mikey and James by their collars and shoved them back a couple feet. “Leave Jackson alone. If I find out you two been saying shit, you’ll be in the next round of layoffs. Is that clear?”

They huffed, but nodded. They needed their jobs.

Robert sighed, heading back to his office to replay the morning meeting in his head. He had been too hard on Jackson, himself. Poor kid. He was barely 22, the youngest in the department. Boy was he cute, though. And handsome, too. There had been many lunch hours spent dreaming about that young man, his mouth around Robert’s thick hard -

He swallowed. No no. It wouldn’t be right. He was the boss. That’s how people get into trouble, dammit. But oh how he was tempted. He wondered if Jackson was dominant in the bedroom, or if he was submissive… or maybe a switch? God how he wanted to find out. Just once.

Famous last words, amiright?

Mikey and James waited in the parking lot after work, shoving Jackson to the ground when he neared his car. They taunted him, asking if the boss liked having his dick sucked. That had to be the only explanation as to why he told them to lay off of Jackson. The words turned physical, fists raining down as Jackson curled up into a ball and took it. What else could he do? He was scrawny, weak. He couldn’t fight back.

A shout rang out, echoing in the parking structure as footsteps approached. The bullies ran off, leaving Jackson bleeding and shaking on the ground. He wanted to cry, to give up. It was just like highschool again.

Brown loafers stopped in front of Jackson, his vision blurred. He couldn’t make out who it was. Didn’t want to. Didn’t want to admit to needing a savior.

Strong hands helped him to his feet and over to another car. Not Jackson’s car. Jackson’s car was rust and off white. This car was sleek and black. The door opened and he felt himself sat down in the back seat, legs hanging out the window as his guardian angel rummaged through the trunk. He came back with a first aid kit, cleaning the cut on Jackson’s temple. It stung, the young man hissing in pain at the alcohol.

Robert’s voice asked him if he was okay. But why? Why would Robert care?

His vision focused, settling on the handsome face in front of him. Robert’s face. Robert’s car. Robert. Why Robert?

He let him bandage him up, the whole time watching his movements carefully. “Are you alright, Jackson?”

He nodded, a bit dumbstruck that Robert Jones, THE Robert Jones was talking to him in a non work capacity. It didn’t make any sense. It seemed like he had always gone out of his way to avoid him. Finally he came to his senses, pulling his head out of his ass as he stuttered out an “I’m, I’m f-fine.”

“Are you sure? You don’t need to go to the hospital or anything do you?”

Jackson shook his head. No, he didn’t need a hospital, but he probably shouldn’t drive. “If, uh, if you could… just, call me an uber or something, I’ll be fine.”

“An Uber? Hell no, not in your condition. Come on, I’m gonna take you home.”

Jackson was still too out of it to question why Robert knew where he lived. I mean, he was the boss. It was his job to know, right?

He wasn’t expecting to see the black car again in the morning. Nor was he expecting Robert to pound on the door until he answered. “I’m coming, I’m coming, chill, geez.” He threw on his robe and opened the door, somewhat annoyed with his boss. “What?”

Robert shrugged. “Nothing. Just… making sure you’re still alive. You didn’t answer your phone.”

Oh. That was it then. He was just checking up on his employee. That was all. Disappointing, sure, but Jackson was used to disappointment. “Oh, um, sorry. I had it on Do Not Disturb. Just wanted to rest, you know?”

“Yeah, okay. Comeon, get dressed. I’m driving you to work. Your car is still there.”

“Oh, um, alright, I guess. I’ll be ready in five.”

Robert nodded, sitting down on the couch while Jackson finished getting ready. It was tempting to join him, but Robert simply shifted his position on the couch and waited.

The drive to work was awkward as hell for both of them, neither one wanting to break the silence. There were too many expectations and too little space.

Robert seemed to forget about the incident for a few days, flat out ignoring Jackson unless he was required to talk to him for work. Jackson didn’t know what was going on, what was happening. But did it matter? It wasn’t like there was any chance for the two of them. He sighed, going back to work. It wasn’t like him to get his hopes up, but he had with Robert. He guessed he was wrong.

Or at least, he thought he was.

It was a week later when Robert cornered him in the parking lot, backing him up against the wall and placing his hands on either side of Jackson’s head. Robert huffed, his eyes dark and full of lust as he leaned forward and captured Jackson’s lips in a kiss. Jackson whimpered, pulling back for a moment before he sighed and leaned into it, his hands wandering the back of Robert’s jacket. The kiss was hard and needy, Robert’s whiskers rubbing a red rash on Jackson’s sensitive skin as their lips mashed together. He pulled back, eyes searching for consent, for permission to keep going. Instead of words, Jackson wrapped his hand around the back of Robert’s head and pulled him in for another kiss, then another, until their hands were roaming and curious about what they could and could not touch.

“Fuck me, Jackson. I’ve been wanting to do that since I hired you.”

“Really? I thought you hated me.”

Robert shook his head. “No. I could never hate you. I’m just hard on you cause I know you can handle it.”

Jackson nodded. That made sense. Kind of. Whatever. He was liking this moment anyway. Plus they were the last two at the office so there was no one to catch them. He let out a shaky breath, pulling Robert in for another kiss. Mmm, he hummed, something that made Robert chuckle. “Enjoying yourself, Jackson?”

The young man nodded. Fuck yes he was enjoying himself.

“How about now?”

Jackson gasped as Robert grabbed his hardening length through his pants. He groaned, pushing his hips forward into his grasp. “Fffuck.” he stuttered, not expecting the contact. It wasn’t unwelcome, that was for sure, but couldn’t they get in trouble for this? Jackson closed his eyes, focusing on the words that didn’t want to leave his tongue.

“Don’t um, can’t… I mean, won’t we, won’t w-we get in t-trouble for this?”

Robert shrugged as he undid the belt around Jackson’s waist, working on freeing his erection. “I’m not gonna tell. Are you?”

Jackson shook his head. No. He was not going to tell. Who would believe him anyway?

He opened his eyes, watching as Robert pulled his hard cock from his pants. It was already dripping with precum, a dark wet spot forming on the fabric. Robert knelt down, and while Jackson was more than eager, he still hesitated. “You don’t, you don’t have to do this, Sir.”

Robert almost purred. He liked it when Jackson called him Sir. “Oh, I know, but I want to.”

Jackson nodded, watching as Robert leaned in to lick the salty precum from his dick. Was Robert gay and Jackson had just completely missed that fact? No, he went on dates with women all the time. Bi, maybe? Did it matter? Robert was humming in enjoyment at sucking his dick, that was all that mattered. His tongue was magic. Robert knew his way around a cock, that was for sure. Jackson wasn’t going to last long with this treatment. He felt himself growing closer, and he tried to pull Robert away, to stop him before something happened that he couldn’t take back.

Instead of complying, Robert redoubled his efforts, drawing the orgasm from the depths of Jackson’s balls before he swallowed down every last drop. Jackson had to lean back against the wall to steady himself as the world spun. Holy fuck. That was hands down the best blowjob of his life. Robert really knew what he was doing.

He hummed, standing up as he licked his lips. Then he kissed Jackson again, made his knees wobble and his resolve weak with the way he moved his tongue. “Jackson…” he breathed out, his voice heavy and full of lust.

“Yessir?” Jackson breathed, panting heavily as he waited for Robert to continue.

Fuck. There was that Sir again. Something about it made Robert’s insides tingle. He certainly didn’t mind, that was for sure.

“I want to fuck you. I want to take that hot little ass of yours and make it mine. I want to mark you as mine, leave hickies on your neck just below your collar. I want you, all of you, and I want you now.”

Jackson whimpered. He hadn’t expected Robert to be so straightforward with his intentions. Slowly, he nodded. “I want that too, holy fuck, please.”

Robert growled, kissing him one last time before shoving him towards the black car. “Get in. We’re going to my place before I take you right here and now.”

Jackson quickly slid into the passenger seat, holding on as Robert floored it, speeding the whole way to his house. They made the 20 minute trip in nearly half the time, and they were kissing before they even got to the front door. Robert was doing his best to unlock the door without letting go of Jackson, but he finally held up a finger and motioned for him to wait as he fumbled with the key.

Once the door was open, they were back in each other’s arms, hands touching and feeling and knowing just where to go next. It was as if they were one body, seeking the ultimate pleasure.

Jackson excused himself to go to the bathroom while Robert picked up his room a little and got out the lube and a condom. When Jackson returned, Robert frowned. “Jackson… why are you wearing clothes?”

Jackson blushed, suddenly self conscious as he began to get undressed. It was hot, watching him strip. He had a nice body, just not one that was made for fighting. And that cock, mmm, that cock was beautiful, just like the rest of him.

“Now come undress me.” Robert ordered, his voice soft yet firm. Jackson swallowed, looking down for a moment before walking over to him and undoing the buttons on his shirt. It took a few minutes with how shaky his hands were, and Robert stopped to grab his hand and look him in the eye. “Jackson, it’s okay. We don’t have to do this if you don’t want to. I know this is moving kind of fast.”

Their eyes met, and the last drops of hesitation left Jackson with those words. He was safe. This wasn’t something that would backfire if he backed out. This wasn’t his ex. This was Robert.

Robert was safe.

Kind.

Knowing.

Robert wouldn’t hurt him.

He shook his head. “N-no. I want this. It’s just… it’s been awhile, that’s all.” Jackson quickly undid the rest of the buttons and Robert’s belt before undoing his pants. Jackson’s dick was already half hard again, and the sight of Robert’s cock was enough to make him moan. Robert was long and thick, very decently sized. Maybe even too big, Jackson thought with wonder. He shook the thought away, grabbing the lube from the bed as he dropped to his knees. He opened his mouth around Robert’s hardness, barely able to fit it in as he swirled his tongue around his length. Eventually he was able to take in a few inches, but not more than that. With one hand, he pumped Robert’s erection. With the other, he forced lube inside his hole, fingering and stretching himself as he moaned around the cock.

Robert sighed at the treatment, pulling back without warning before shoving Jackson onto the bed. “Turn over, on your hands and knees.”

He did as he was told, waiting patiently. He yelped as Roberts tongue made contact with his asshole, rimming him and shoving inside. He moaned into it, pushing his ass back onto Robert’s tongue. Jackson sighed, his eyes rolling backwards at such a new sensation. He hadn’t known just how good that could feel, holy fuck.

And then the tongue was gone, replaced with a finger that slowly pushed inside. Jackson hissed, allowing himself to enjoy the feeling. One finger became two, became three, and he winced at the slight burning pain in his asshole. Robert shushed him, whispered sweet things in his ear as he prepared the younger man for his cock.

After a few minutes of slow fingerfucking, Jackson was literally begging for more. “Please, sir, Please just fuck me.”

And how could such a gentleman refuse?

Robert grinned, squeezing a large amount of lube onto his cock, rubbing it in before pressing the head into Jackson’s entrance. Jackson cried out at the intrusion, squeezing his eyes shut against the pain. Robert kept going, knowing it would be better once the head was inside.

A couple sharp thrusts and he was in, the bulbous head popping past the ring of fire. He grunted, Jackson whimpering as his body adjusted. Robert stayed still for a couple of minutes, until Jackson was starting to rock his hips back and forth against his length. Robert smirked, picking up on that small fact as he started to thrust his own hips. In and out, in and out, in and out, until he was slowly fucking Jackson’s ass. Jackson moaned, pumping his own length back to full hardness as he was fucked by his boss. “Oh, god, boss, oh shit fuck fuck fuck!” Jackson let out a string of curse words as Robert started to speed up, thrusting his hips harder with each movement. Robert grunted, pouring all of his strength into each thrust, enough to lift Jackson’s knees off the bed. Robert grabbed his hips and held him close, his movements becoming more wild as his climax neared. Finally he grunted again, his cock pulsing as he came. Jackson felt himself be filled with Robert’s hot seed, and it sent him over the edge, pulling his own orgasm out as he shot cum on the bed.

Jackson collapsed on top of the wet spot, not caring about the mess. He was too satisfied. Robert pulled out, disposing of the condom before spooning up next to Jackson, kissing the top of his head.

It didn’t take long for Jackson to fall asleep, soft breaths that rose and fell with the movement of his chest. They could talk more when he woke up. For now, this was nice.

After half an hour, Robert pulled himself from the bed to go shower and make food. He knew Jackson would be hungry. And they had a lot to talk about. But such conversations could wait until after food. At this very moment, neither of them had anything to worry about.