Hookup Office

It was 3pm on a Tuesday and Jack was working from home. With two hours left in the workday, Jack was exhausted and completely over it. He had been stuck in back-to-back meetings since 9am. Now in his mid-twenties, Jack had been at this job since he graduated college. The monotony was truly getting to him.

Jack was also recently single. He had spent the last two years with a mediocre boyfriend, who wasn't all that nice, intelligent, or even good at sex. They had grown to be entirely celibate in the last 6 months of the relationship, which had driven Jack to insanity due to his love of bottoming. Feeling particularly lonely a few nights back, Jack had re-created his old hookup profile to get back out there. After going so long without sex, he was certainly excited for a few random hookups. That being said, his nerves had gotten the best of him and he hadn't gone through with anything yet. All day, Jack was trying to be professional by turning off his notifications. He didn't want to be distracted by the random messages from men looking for a quick hookup. But after 6 hours of meetings, temptation was starting to get the better of him.

"Just a quick peek," he thought, picking up his phone and looking through his recent messages.

As a fit twunk, Jack tended to get a good number of messages. Lots of them were always from men with no photos or information, or from people many miles away. But one message in particular caught his eye: Just twenty minutes before, a man had messaged Jack from only 900 feet away. Jack lived in a quiet and mostly residential part of a city, so he was surprised to see someone new nearby. He opened the message to check it out.

"Sexy photos. I love a bubble butt like yours. Interested in something soon?"

Jack checked out the man's photos. Identified only by the name Mark, he was older than the guys Jack usually went for. Mark appeared to be in his mid-fifties, with a clean-shaved face, short and dark hair, and a charming smile. Jack couldn't get a good read on his body since Mark was wearing clothes in all his photos, but he appeared to be tall and have a medium build. Jack was curious.

"Thanks, man," Jack responded. "Got any more pics?"

Mere seconds later, the man replied with three photos. In the first, he was standing in front of a mirror wearing just a pair of white boxers. Jack was impressed by his body, which wasn't necessarily toned but was certainly muscular. His skin was tan, coated lightly with black chest hair and a solid treasure trail to his crotch. He was definitely a daddy type.

The second photo was of his cock. Fully erect, it was next to a plastic water bottle for scale. It was impressive, about 8" long and reasonably girthy. Jack immediately noticed a thick vein that went the entire length of the shaft, reaching a bulbous head. Jack knew it'd be a hard cock to take, but would feel incredible when he loosened up again.

Jack loved the third picture best. Mark's cock was resting on top of someone's ass, which was covered in thick globs of cum. Jack could see cum leaking out the anonymous asshole, as well as a red handprint on the ass cheek. Clearly, Mark could fuck hard and shoot a load.

"Shit," Jack responded in brief. He was now rock hard in his home office, rubbing his dick through his pants.

"I'm only free for the next hour, so you'll have to come by soon," Mark responded in turn.

Jack looked at the clock, realizing that he would have to play hooky for the hook-up. Even if he could sneak away from work, was he ready yet to take a stranger's dick after such a long relationship? He couldn't tell if his nerves were keeping him from doing something he would later regret, or if they were simply getting in the way of a good fuck that would help him get over his ex.

A few minutes had already passed, and Jack knew he had to make a decision. As if his fingers had a mind of their own, he impulsively typed away "Now's good. Where are you?"

"At the office. Any chance you could act like I'm your realtor?"

This was getting kinkier by the second. Still, Jack couldn't back down now. This was the perfect chance to get back out there, get pounded by an older man with a huge dick, and even live out a fantasy of getting fucked in an office. Before he could think too much about it, he replied.

"Sure, I'll try to look professional. Address?" A moment later, Mark sent his location. After quickly putting on some nicer clothes and setting his slack status to "Be back soon," Jack headed out the door.

--

Jack approached the address, a discrete single-level office park nearby. He hadn't even noticed the realty sign before, which happened to have a small image of Mark's face on the side. Luckily, the business looked legitimate. Opening the front door, he entered a small, modern lobby with a sitting area to the right and a receptionist to the left.

"Hello, how can I help you today?" The receptionist looked to be about Mark's age, but much more flamboyant and considerably twinkier.

"Hi. I'm here for a meeting with my realtor, Mark." Jack tried to act normal and confident, and not like he was here for his first hookup in years.

"Sure. Mark just mentioned that he was expecting someone," the receptionist said with a soft smirk. "You can sit down while you wait."

Jack couldn't tell if the receptionist knew about the hookup, or if he was just acting paranoid. It's not like it would matter to Jack, since this wasn't his office. He tried to relax as he sat down on the couch nearby to wait. Luckily, he didn't have to hang out long.

"Good afternoon," Mark said confidently as he entered the lobby. As Jack stood up to shake his hand, he took in Mark's appearance. If anything, he looked better than his photos. About 6'2", he was wearing a well-tailored navy suit that accentuated his muscular frame. Besides a crisp white shirt and gold-colored tie, he wore an expensive-looking gold watch. His teeth were perfectly white and his eyes a dark shade of blue. This man clearly was successful.

"Hi Mark, nice to see you again," Jack said, trying to play cool.

"You too," Mark replied, clearly trying to play off the fact that he didn't even know Jack's name. "Want to head to my office?"

"Sure," Jack responded, following Mark back into the offices. It was a surprisingly large space, with rows of cubicles. They passed by at least twenty different realtors who were chatting on the phone or with clients in person before they arrived at the only private office that Jack could see. Mark motioned him in and closed the door behind them.

Jack sat down in a chair in front of the desk, while Mark sat on top of the desk directly in front of him. Both due to Mark's large stature and the height of the desk, Jack felt small in comparison.

"Thanks for coming on such short notice, um..."

"Jack," he said, finishing Mark's sentence. "I've never met someone in their office before."

Mark laughed softly. "I wish I could say you were the first, Jack. Let's just say it's a kink of mine."

Jack grabbed Mark's thigh and was immediately surprised by its thickness. "Seems like a benefit of being the boss and having a private office. But before we do anything, I have to tell you something."

Mark looked simultaneously intrigued and concerned, like Jack was about to tell him something that could ruin the moment.

"Well, I just got out of a relationship, so this is my first hookup in a while."

"How long has it been?" Mark asked curiously.

"About two years since my last hookup. But if I'm being honest, it's been about 6 months since I've had sex," Jack replied sheepishly. But to his surprise, Mark looked even more turned on.

"Even better," he said with a sly smile.

"Why's that?" Jack asked. "I was worried it would freak you out."

Mark looked down at him as though he was trying to pick the exact right words to express himself. "There's nothing I like more than a nice, tight hole. That's why I tend to seek out young, fit guys like yourself on these apps. And if you haven't actually had sex in 6 months, I bet your ass is extremely tight right now."

Jack smiled. "Yeah, I'm sure it is."

"But best of all, I can tell you want it bad," Mark continued. "That's why you came over here so fast. You just want to get pounded by the boss's big, fat cock."

"Yes sir, I can't wait for you to fuck my tight little hole," Jack begged, leaning into the fantasy.

In that moment, Mark effortlessly lifted Jack to his feet and kissed him. As they began to make out, Jack felt Mark's strong hands caress the back of his head, then lowering to his back before arriving at his ass. Jack moaned in pleasure as Mark squeezed his muscular cheeks over his pants.

"I'm going to fuck that tight ass of yours so hard," Mark whispered in Jack's ear.

Jack felt Mark's hand slide inside his pants. Mark's middle finger pressed firmly against Jack's hole as the rest of his hand spread apart Jack's cheeks. Jack moaned as they continued to kiss.

"Don't be too loud, or the other employees will hear us," Mark told him.

"Of course, boss," Jack nodded in agreement. He took the moment to whip off his shirt, exposing his hairless and muscular torso. Jack had spent a considerable amount of time in the gym, and it was paying off. His chest was well defined and his abs visible.

"You're so fucking hot," said Mark as he began to kiss Jack's nipples. "Now suck the boss's big dick," he commanded as he pushed Jack down to his knees.

Mark quickly unbuckled his belt and unzipped his fly, pushing his dress pants and boxers to his shoes, which were still on. Bare ass on the desk, he beckoned a kneeling Jack closer to his erect cock.

Jack could smell Mark's manly scent as he got closer. Mark's dick was exactly what he'd imagined. A veiny, 8" cock with a big mushroom head. Mark had a thick but trimmed patch of black pubes and low-hanging balls that glistened with sweat. Jack couldn't wait for it.

"Let me taste your big dick," Jack begged.

"You're hungry for it," Mark said seductively. He smacked his cock on Jack's cheeks a few times. "Let's see how much you can take."

Just then, Mark grabbed Jack's head and pressed it down on his erection. Unprepared, Jack did his best to open his throat and let in Mark's lengthy member. But still, he choked on it lightly as it became lubed with his saliva. Mark clearly loved taking complete control of the situation.

"Fuck," he moaned. "Suck boss's cock good."

Jack began to actively suck on Mark's dick, letting his head bob up and down to the rhythm of Mark's thrusts. He ran his tongue along the shaft, which Mark seemed to love. Finally, he held his mouth down so that he was basically kissing Mark's pubes. Just as he ran out of air, Mark yanked back his head.

"Show me your ass," Mark said assertively.

"Yes sir," said Jack as he threw off his shoes and socks, and then yanked down his pants and briefs. He was now standing fully nude in Mark's office. Jack's cock was so erect it pulsed in the air, sticking straight out from his groin. But Mark wasn't interested in that. Instead, he spun Jack around to see his backside.

"You have quite a bubble butt," Mark started. "I can tell you go to the gym a lot. You sure no one's fucked you in 6 months?"

"No boss, you'll be the first," Jack replied.

"Bend over," said Mark as he stood up, pushing Jack towards the desk. Jack spread his legs apart, and then leaned over so that his arms propped up his chest over the desk. Behind him, he could see Mark first remove his shoes and pants, and then slip off his coat and tie while unbuttoning his dress shirt. Now, Mark was wearing nothing but an open shirt and his gold watch.

Mark bent over to spit directly onto Jack's hole, then rubbed it in with his hand. Jack squirmed as Mark's strong fingers played with his ass. Even Jack could tell he was especially tight from such a long dry spell. Mark's big cock would surely set him right.

"You're such a little slut, getting fucked for the first time in months by a complete stranger in his office," Mark told him with a sexy grin on his face. "We'll see how you take this big dick."

Mark went behind his desk and opened a drawer, pulling out a small bottle of lube and a condom. Just before he ripped open the condom, Jack noticed and stopped him.

"I want you fuck my tight little ass bareback," he told Mark. "I'm on PrEP," he added assuringly.

"Fuck yeah," Mark replied, throwing the condom to the ground and pouring lube onto his dick. "You want to take the boss's big dick raw, don't you?"

Mark was now slapping his cock on Jack's hole. Jack turned around to nod, hornier than he'd been in months and excited to get stretched out by an older daddy. Seeing Mark's cock, he knew it could be painful. The tip was easily 2 or 3 times wider than Jack's hole.

"Stretch my ass," Jack moaned. "Put it in me, boss." Jack loved being submissive, especially with an older man.

Just then, Mark leaned over and wrapped his left hand around Jack's neck. With the other, he positioned his dick right at Jack's hole.

"Don't make a sound as I put it in you," Mark told him. "Can't have my other employees getting jealous, after all."

A moment later, Jack felt a forceful pressure on his asshole as Mark pressed his cock inside. Jack tried to hold in his squeals but couldn't keep silent entirely. Mark quickly covered Jack's mouth with his hand to dampen the sound, but continued to thrust inside Jack's hole unrelentingly.

"Take this big cock," Mark whispered in his ear. "You're going to be completely stretched out after I'm done with you."

After the initial pain subsided, Jack felt the incredible pleasure of a huge cock filling his hole. Mark held his cock inside, rotating his hips laterally to stretch out the hole even more. Jack could feel Mark's shaft against his prostate, making him more sexually charged than he'd been in months.

"I love your raw cock inside me, Jack whispered back. "Now show me who's boss."

Mark got to work. Standing up straight and holding the top of Jack's muscular ass, he thrust hard and deep. Each motion was long and fluid, letting all but his tip leave Jack's ass before completely filling it up again. As he moved, his open dress shirt blew back and forth. Jack could even feel Mark's hanging balls slap against his taint.

"I bet your old boyfriend could only dream of fucking you this good," Mark grunted passionately.

"Yes sir. He wasn't nearly as big or manly as you are," Jack moaned.

Mark's thrusts became shorter and faster with time. He now grabbed Jack's shoulders for added leverage, allowing him to ram his whole groin against Jack's ass. Each rounded cheek became bright red. Jack was in so much ecstasy, he didn't feel the pain one bit.

"You've got me so close, boss" Jack moaned back to Mark.

"Me too," groaned Mark. "You ready to take boss's big load?" He pulled up Jack from the desk so that his muscular chest pressed against Jack's back.

"Yes, Mark," replied Jack passionately. "Give me my first load in months. Breed my hole raw!"

As the wave of Jack's orgasm crested, he felt Mark's thrusts build up as he began to shoot his load. Silently but with heavy breaths, they both shot their loads forcefully. Jack's dick sprayed cum out onto Mark's desk, covering a stack of papers with his white, sticky seed. Mark unloaded deep inside Jack's hole, pumping out countless fat globs of jizz.

When they caught their breaths, Mark pulled out his cock in one slow, long motion, letting his cum spill out to the carpeted floor beneath them.

"I came so much in that little hole of yours," said Mark as he wiped the sweat from his face. "Hope you had fun."

"Are you kidding, that was easily the best sex I've ever had," Jack replied with a huge grin. "Thanks for the fuck, boss." He winked.

"We better get cleaned up. I do have to run to a meeting in a few minutes," said Mark, wasting no time. "But maybe I'll see you again sometime?"

"Sure thing. Gotta keep the boss happy, after all."

--

After hastily throwing back on his clothes and trying not the let Mark's cum leak from his now gaped ass, Jack had run home to return to work. Getting back to his desk just before 4pm, he was reinvigorated and perfectly satisfied after a long dry spell.