Perks of the Job

I stood on the outskirts of the high-rise buildings, digging a finger into the collar of the starchy dress shirt I wore. It was wholly uncomfortable, made only worse by the fact that I was incredibly nervous about whatever the hell I was walking into. I’d gone to the address Mr. Hill had given me and found myself at the bottom floor of the headquarters for All Tech, a huge electronics company based out of Chicago. I knew Mr. Hill did something important, considering the size of his house and all of the crap that Sean was able to afford while at school, but I had no idea he worked here.

I walked in through the revolving glass doors and made my way to the front desk and after mentioning a meeting with Mr. Hill, the receptionist at the front pointed me towards one of the private elevators, telling me that the office I needed was on the 53rd floor. The large metal doors slid shut and I now found myself alone in the elevator, with the sole thought on my mind being Mr. Hill.

As best I tried, he hadn’t really left my mind all night, making it incredibly hard to fall asleep as every image I conjured in my mind just made me incredibly horny. Even after taking a nearly ice-cold shower, I wasn’t able to control it and I knew that if I just gave my cock a few strokes, I’d shoot all over my chest and be able to sleep. But Mr. Hill had told me not to and by God I was gonna follow through on that order. Even now, as I had my back against the rising elevator, I could feel the front part of my dark, well pressed pants tenting obscenely and I reached down to adjust my semi hard cock. I tucked it to the side of my briefs and willed myself to think of anything other than the night before.

After just a few moments, the elevator opened up to a sprawling office floor, two hallways fanning out behind a large central desk manned by a handsome young man. Again, I asked for directions to Mr. Hill and was told his office was the last one down the right hall. I noticed as I went that this time, the guy pointing the way gave me a solid once over before giving a smirk as I turned away. Not sure if the look was out of jealousy or if the guy was just interested in office gossip, I did my best to look professional and dignified as I walked off, which was truly an astounding feat considering my cock was still throbbing as it was pinned against my thigh.

Making my way down the hall, I hesitated for just a brief moment outside his office. I asked myself if I was truly prepared and ready for whatever was to come and I gave a deep breath, knocked on the door, and walked in after hearing a shout of greeting from beyond the door.

Fuck, I thought to myself, he looks even better in the day. I knew that he was a handsome man, but seeing him here, truly in his element, was a sight to behold. Mr. Hill sat at his ornate wooden desk, chatting on the phone as he glanced over at me, that same cocky grin plastered on his face as he spoke to whoever was on the other end. Since it seemed I had time to wait, I really took in the man before me. His height and size were even more impressive, as his thick arms and chest stretched his starched, pale blue shirt to the limit. I glanced up and took in his handsome features once again. His eyes seemed to glow a golden, green color behind his glasses, and while I’m sure most would wear contacts, Mr. Hill truly made the glasses work for him. His hair was styled in a heavy swoop, with his sideburns and temple fading to grey along with the scattered flecks of grey throughout the rest of his dark black hair. If I had to guess his age, I’d assume he was somewhere in his late forties or early fifties. I moved my eyes downwards and caught myself licking my lips as I saw the tuft of chest hair poking out from the top of his dress shirt, but a sudden clearing of a throat pulled me away from my prize.

Apparently, Mr. Hill had finished up his phone call and must have liked that he caught me staring, as his grin remained. I stood awkwardly near the front of his office, not sure if I should come forward. His deep, resonating voice seemed to wrap around me as he spoke.

“Well, I must say, I’m not surprised you showed up after last night’s ‘festivities,’ considering how excited you were, but still. I’m pleased to see you again boy.” He motioned me forward and I walked closer to his desk, taking my place in one of the chairs across from him. Crossing his fingers together, he rested his chin on them as he leaned forward.

“First things first, I believe proper introductions are in order. While I very much enjoy calling you boy, I think it best that I know your given name, wouldn’t you agree?”

I felt my face blush as I realized he was right. I’d never actually told him my name before I unloaded everything on him. Hell, I’d basically told him I wanted him to own me and he didn’t even know who I was. Deeply embarrassed, I lowered my eyes from him as I told him, “My name is Jesse, sir. Jesse Reeds.”

“It is a great pleasure to meet you, Jesse. My name is Benjamin Hill. And I expect you to look me in the eye when you talk to me from now on, even though you look adorable when you’re flustered, understood?”

“Yes sir.”

“Good. Now, I’m sure you’re wondering what I’ve brought you here for and the answer is simple, boy. I have a job for you, should you want it and pass the interview process.” He told me, a hint of excitement and mischief in his eye.

I was surprised to say the least, but replied, “I’m interested sir, but…what exactly would I be doing.”

“I am in dire need of an assistant. Someone who can help me keep track of things, answer calls, plan my schedule, and advise me on important decisions. However, from our little chat last night, I gather that you are pretty bright and I wouldn’t want to completely waste your talents, so you’d be working half the time for me and the other half of the time in one of the other departments. You mentioned that you studied environmental science during school and I’ve arranged a spot for you in our environmental compliance department.”

Holy shit. I couldn’t believe it. While it wasn’t exactly the job I’d been looking for, it sounded interesting enough and I knew that All Tech would be a huge stepping stone for my career. I thought about having to fetch coffee, man the phones, and performing other menial acts of labor, which wasn’t exactly appealing until I remembered the other duties involved. Mr. Hill had clearly emphasized the fact that I’d be around him for most of the day, and just the thought of being alone with more often started to make my cock grow rigid in my pants. I shifted in my seat a bit at the thought and watched as the man across from me glanced down at my crotch, licking his lips as he did. Ignoring that for now, I tried to focus on the rest of the offer.

“Well sir, this all sounds amazing, but you mentioned an interview too. When would that happen and who should I get in contact with?”

“Oh, my dear boy, your interview starts now,” he said, leaning away from me and reclining further in his leather office chair. He placed his feet on the desk, looking very relaxed before he spoke up again. “Strip for me.”

In a fit of confusion and surprise, I stammered out a weak, “Ex…excuse me, sir?”

“You heard me, boy. I said, strip. Now.”

There were dozens of thoughts running through my head and emotions playing out on my face at the moment. Surprise, indignation, anxiety, but at the base of it all was this growing sense of warmth, like my body was slowly igniting. I knew from walking down the hallway that his office was fairly secluded, but there was still the massive glass wall behind him that looked out on to the other financial buildings of The Loop. There was a big chance that someone from the building across the street could look over and see what was going on over here, but never the less, I slowly reached up and started to unbutton my shirt.

Keeping my eyes locked on Mr. Hill, I noticed the flicker of surprise on his face for just a second, before he replaced it with a look of deep lust and desire. If I was going to strip, I was sure as fuck going to do it well. While I slowly peeled off the stiff dress shirt he’d instructed me to wear, I gently placed it on the back of the chair. I was less careful with the plain white undershirt I wore and slowly tugged it from the band of my pants. I could see his eyes glance down at the small treasure trail that poked out from my pants and I think he was pleasantly surprised by the amount of hair on my chest, as I gradually shed my shirt and tossed it aside.

I kicked off my shoes next, not caring about the loud clack that echoed around the otherwise silent office as they struck the hard floor beneath my feet. I started to unbuckle my belt, but pulled my hand away for a second, reminding myself that this was supposed to be an interview, and I wanted to make my enthusiasm apparent. I moved across the room, circling behind Mr. Hill’s desk, his head and body swiveling in the chair following my movements, as I stopped in front of the large window. Continuing with my belt and pants, I slowly pulled down my waistband, leaving myself in just a pair of black dress socks and white briefs that I wore especially for him after seeing his own last night.

My cock was throbbing in my tight underwear and there was a growing wet spot on the front from the constant drip of precum I’d had going since I walked into the building. I stood before Mr. Hill, watching him palm his own cock through his pants. “All the way, boy,” he said, motioning with his other hand to my still covered cock.

I gently tugged down the band of my briefs, giving him a peak at the dark hair that grew around my cock. I preferred to keep it mostly trimmed, as I didn’t have much to show down there and didn’t want my cock to get lost in a tangled bush. Right now, my five-inch cock stood out rock hard, slowly dripping precum from the sheer pleasure I was experiencing from showing off for Mr. Hill. With my now slightly damp briefs in hand, I wanted to show I had at least a bit of say in this whole arrangement and tossed them to Mr. Hill.

Not breaking eye contact, he snatched them from the air and without hesitation, brought them to his nose and gave a deep inhale. The moan that issued from his mouth was so deep and guttural, it brought back all the memories of the night before and my cock bounced heavily, my precum flinging off the end and falling to the floor in front of me.

I remembered he said all the way off, so I reached down and pulled of the last stitch of clothing I had on and threw my socks to the side, now fully naked in front of the sexy man before me.

“Face the window, boy,” he said, before taking another huff from my briefs that he still clutched in his hand. I complied, placing my hands against the window, presenting my ass to him and presenting my cock to the rest of Chicago. I could feel his eyes on my ass, which were no longer sore from the night before, but the intense stare I now felt honed in on me was enough to bring to mind that deep thrum of pain and pleasure, as echoes of his slaps replayed in my mind.

“I want you to start stroking your cock, boy. Get yourself close to cumming, but stop before you shoot. Understand?”

I gave a nod to him and reached down, grasping my hard cock in my hand and gave a few slow strokes at first. I usually didn’t leak this much precum, but I also don’t usually strip naked in front of hot men and present myself for the world to see, so everything was a bit new today. The slick, warm liquid coated my hand and made it easy to glide my encircled fist up and down. I glanced out at the vast expanse before me, looking out across the road and could see a handful of people in the nearby building, although I didn’t see any of them glancing up here just yet. My breath was now coming out in short, quick huffs, fogging up the window in my excited state.

I heard a faint snap behind me, but I was focused on the task in hand at the moment. It was only about a minute or two of stroking before I had to take my hand off it and whimpered out, “I’m close sir.”

“Good boy,” I heard from directly behind me. It seems Mr. Hill had stood up from his desk and now hovered near me. I felt his hot breath on the back of my neck, followed quickly by a handful of tickling kisses as his mustached brushed against my overly sensitive skin. I now knew what the snap was from as I felt the cold liquid slowly being spread across my hole, as he slid in one of his thick fingers deep inside me. I gave a sharp cry of pleasure as he instantly hit my prostate, making it clear that he’d done this before.

“Keep stroking, but stop when you’re right on the edge.”

I nodded, lost in the pleasure coursing through me, but understanding his demands. I picked the pace back up and continued jerking off, but again, it was less than a minute this time before I moaned out again, “I’m going to cum, sir.”

With one hand, he reached out and stopped me stroking, his vice like grip on my wrist holding me in place, while his other hand continued to prod deeper in my ass. In fact, he started to thrust his fingers forward, giving me the feeling of being fucked even though I knew it was just one of his thick digits inside me.

We continued this whole process for a few more minutes, him fucking me with his finger and me being brought to the edge and back several times. By now, I was writhing in his grasp, vibrating with the pent-up energy from our current activities and the leftover horniness I’d been left with the night before. It felt like an eternity before I felt his bristles right on my ear as he spoke, “Cum for me, boy.”

He slammed his finger in one last time and I didn’t even need to have my hand on my cock before I felt jet after jet of hot cum shoot out onto the window. I cried out loud this time, not caring if the rest of the office heard me as I was lost to the overwhelming sensations Mr. Hill was bringing out in me. After a few moments of me catching my breath, I glanced down and saw the massive load I’d spilled all over the window. I was amazed by the display in front of me, but my attention was drawn elsewhere as I felt the finger slowly being pulled out of my well stretched hole.

I turned around and Mr. Hill still towered over me, and I nearly melted to the floor at the look of pride he gave me. I noticed he glanced down past me to the window before he spoke up again.

“Well, well, well, boy. You made quite the mess, didn’t you? Clean it up for me.”

I looked back towards his desk and the rest of his office, trying to find a rag or something, before I felt his hand gently grab my chin and making me meet his eyes again.

“Uh uh. Lick it up, boy,” he said, and pushed my face down towards the glass. While not painful by any means, the pressure of his grip forced me to my knees and I found myself face to face with the enormous mess I’d created. I figured by this point hesitation was bad and with my tongue outstretched, I began to lick up and down the cum splattered all over the glass. I’d only ever tasted my own cum a handful of times before and while it wasn’t gross, I didn’t enjoy it as much as I expected. However, today, it was fucking hot.

As I was down in front of the window, I felt Mr. Hill kneel beside me, his gaze just inches away as he watched my progress. He spoke up in a gentle tone.

“Needless to say, boy, but you have the job if you really want it.”

I paused for just a second, muttering out a breathy, “Yes sir, I do,” before I went back to cleaning up the mess before me. It took maybe a minute more before I’d gotten up all traces of our encounter off the window and turned my head to meet Mr. Hill’s.

“There are just a few ground rules I want to lay out for you before you start here,” he said, and I nodded along.

“First things first, you don’t mess around with any other guys. You’re mine, got it.”

“Yes sir, but I’m a bit confused…” I said.

“What is confusing about that, Jesse?” he asked, a slight tinge of annoyance entering in his words.

“I’m confused as to why you’d think I would want anyone else, sir.”

He paused for a second before bursting out with laughter, “Oh my, you really are a good boy, aren’t you?” he said, giving a small pat on the cheek. I blushed furiously as he continued with his rules.

“Two, I am a very busy man and we might not be able to do this as often as you would like, but I still expect you to follow rule number one even if there has been a long break since the last time. If you ever feel like I am neglecting you, tell me and I will do my best to fix it.”

I nodded along once more.

“Lastly, as I’m sure you are aware, I am fairly into the domination side of things. We will go over your limits and interests at another time, but I want you to be aware that if at any point you grow uncomfortable, tell me. You are not beholden to me and if you do well in your other job here, you are free to cut ties with me and continue on working with the company. Is that clear, boy?”

“Yes sir, I understand,” I said, nodding enthusiastically.

“Good. Now, I’ve already pushed back two meetings for us to conduct this little interview and I must ask that you let me get back to work. Please put your clothes back on and tomorrow you will report to Lyle at the front of the office. He can help you get settled in, answer your questions, and show you around.” He said, getting up from beside me and returning to his desk. I was thrown off by the quickness with which I was dismissed, but I gathered my scattered bits of clothing and started to put them back on when I noticed that Mr. Hill still had my underwear.

Without even glancing at me, he spoke, “If you are waiting for these, I am afraid that you will not be getting them back.” He held up my briefs in his hand. “And from now on, I expect you to only wear white briefs like this when you step into the office. If that is a financial burden, let me know now.”

I thought for a second and remembered that the white pair currently clutched in his hands were actually quite expensive. I had another pair, but they were black. “Actually sir, yes. They are a bit expensive and those are the only pair I have in white.”

He glanced at me and gave a curt nod. He reached into one of his desk drawers and pulled out his wallet, pulling out a sleek credit card from within before placing it in front of me. “Purchase more and put them on this card. And please, do not lose this as they are hard to replace,” he said. Noticing my confusion, he turned away from his computer and gave me more of his attention. “There will be times when I need you to fetch things for me, whether that has to do with work activities or not, and I need you to be able to purchase them quickly and reliably. I understand you just graduated, so I don’t expect you to pay for these things. This is the simplest solution.”

I sputtered a quick reply, “That is very generous sir, thank you.” I grabbed the card from his desk and put it in my pocket, awkwardly feeling the pocket liner rub against the bare skin of my thigh.

He turned his attention back to the computer and although it was not spoken, I understood that I was dismissed. Gathering my belongings and my thoughts, I turned and walked out of the office, a spring in my step as I realized I’d scored a hot new job and a fucking awesome guy in the same day.