Perks of the Job

It had been nearly three months since I started working for Mr. Hill. Every week was some new form of sexual experience and I have to be honest, I really enjoyed getting to worship this man at every opportunity. I’d finally moved into my own place, a far nicer apartment than I should have been able to afford, but with the amazing paycheck from All Tech, I’d managed to find a single bedroom away from the prying eyes of my college friends.

Now, every night when I got home from work, horny out of my mind from being teased by Mr. Hill, I’d take out those long-soiled briefs and jerk off before bed. And he was a true man of his word. Every Friday I’d wear them to work and he’d make sure I made it back satisfied, with new scents to explore for the week to come. However, even with our weekly dinners and several late nights, I still felt like there was something not right between us. During dinners, he’d ask me about my week and how work was treating me, but it always felt surface level, even though I thought there was something more to us. I also noticed how he would never let me kiss him on the lips, always pulling away or moving around so I’d end up on his neck. He sometimes kissed my body, but again, it was always intimate up to a point where I felt like he’d start to withdraw.

I’d tried to gently bring up what exactly our relationship was, but it seemed every time I tried, there was something getting in the way, whether it bit a phone call, some urgent meeting, or Lyle bringing in something to Mr. Hill from one of the other higher ups in the company. I still loved keeping him company, but I felt a little trapped in our situation. I now found myself just beyond the door to his office, building up the nerve to talk about my current feelings when the door opened up in front of me and Mr. Hill’s huge form barreled into me.

I gave a yelp of surprise, not only from the sudden weight nearly pushing me to the ground, but also from the strong hand suddenly gripping my lower back, holding me in place and keeping me from sinking to the floor.

“Ah, Jesse, I was just on my way to talk to you,” he said, pulling me back up to my feet before he stepped aside and ushered me into his office. I following, blushing slightly as I rushed into the room so no one on the floor could see my now very obvious hard on bulging out the front of my pants.

Mr. Hill closed the door behind me and walked over towards his desk, me trailing behind him before taking a seat. “Tell me, boy, did you have any urgent plans for this next week?”

Thinking for just a moment, “Uh, no, not really sir, why do you ask?”

He met my gaze for a second before letting out a gentle sigh. “Well, I was supposed to attend a business meeting in New York with another one of the VPs, but he pulled out at the last second and now has dumped all the responsibilities on me. I was hoping to have you tag along and help me ensure everything runs smoothly.” He said, taking in the look of surprise on my face. “I know you might not have as much experience, but you have proved to be a great assistant and from what I’ve seen of your job with me and your job with the other floor, I’m sure that you are up for this task. So, should I go ahead with planning on you joining me or should I ask Lyle to come instead?” He said, a glint of mischief in his eye, knowing I’d take the bait.

“Of course, I’ll go with you sir,” I said before smiling slightly. “Plus, I’ve never been to the Big Apple. Maybe I can see some of the sights while we’re there.”

He gave a light laugh at my enthusiasm. “Maybe I’ll join you on one of our days. Oh, and before I forget, the same rules I’ve given for you here will apply while we are away.”

“Yes sir, I understand.” I replied. To be completely honest, I’d come to like most of the changes Mr. Hill had asked of me. At this point, I had developed my own musky aroma, nowhere near as potent or mouthwatering as his, but still, it did make me feel a bit more attractive. Same goes for the now well-groomed beard and mustache I sported. I’d gotten a lot more compliments from my friends and I’d even noticed some guys checking me out as I wandered the streets of the city.

I was about ready to head out when he spoke up once more.

“Oh, and one last thing. I would ask that you bring along the items I asked you to purchase when you started working here.”

I turned around and was a bit confused. Of course I’d bring the fancy clothes and underwear he had me buy. I mean, they were pretty much what I wore on a daily basis nowadays. Seeing the confusion on my face, his grin grew wide. “No, boy, not those.”

Thinking for a moment more, I felt the heat rush to my face. Oh. Those clothes. 

The past few months had been so hectic and busy that I almost forgot about the leather gear that now sat in my closet. I remember going to the well-stocked sex shop near downtown and how the hunky worker there took some measurements for a custom order. Everything there was incredibly expensive, but I knew better than to question Mr. Hill when he wanted to spend money on something, even if I still felt odd that he wanted to spend it on me. A week later, the items I’d ordered showed up and I had a hard time focusing on anything else. I’d finally put them under some old clothes at the top of my closet and the busy work week helped push the thoughts from my mind. That is, until now.

“Yes sir, I’ll be sure to bring them,” I said, before pausing and adding in a bit of a quieter voice, “Will you be bringing something like them as well, sir?” I felt the blush creep even further up my face and I knew I must have been very red, which was only made worse by Mr. Hill adding in a deep, guttural whisper, “Oh yes, boy. Don’t you worry about that.” Still sitting behind his desk, he turned back to his computer.

“Now, I suggest you go finish your assignments and make sure you get whatever needs to be done for next week finished. We leave tomorrow and I want as little distraction as possible while we’re away. Understood?”

“Yes sir. See you tomorrow then?”

He looked up at me, a deep hunger reflected in his eyes. “See you tomorrow, Jesse.”

***

I wasn’t expecting to fly first class, but I certainly wasn’t going to complain. Even for a relatively short flight, it was nice to bask in the luxury, especially with my current travel companion. When he picked me up at my apartment, I was a bit shocked. It seemed like he dressed down for the flight, wearing some loose-fitting athletic shorts and a simple t shirt. Sitting in the passenger side, it took so much effort not to reach over and run my hands over his slightly exposed, hairy thighs, but I figured it was best to not make a mess of ourselves before a busy day of travel.

I now found myself reclined in a cushy seat at the front of the plane, reading some trashy fantasy book and sneaking glances at Mr. Hill. After take-off, I had to hide my amusement at watching him stave off sleep, as the noise of the plane around him and the comfortable seating tried to pull him under. Eventually, he succumbed to the temptation and gently slumped back in his seat, and the sounds of his deep breathing next to me kept pulling me away from my book. It became even harder to focus when he shifted in his seat and moved onto my shoulder, his head just a few inches from my face.

I’d never seen him in such a vulnerable, open state. The lines of stress gone from his face. In a moment of pure reflex, I gave him a kiss on his forehead, causing him to stir for a second before settling back into position. His well-groomed hair was close by and I was drawn to the rich, woodsy scent coming from him. For the rest of the flight, I just sat there finishing up my book, content with having Mr. Hill so close to me.

However, as the plane touched down, he finally woke up, and realizing his position, pulled back a little too quickly for my liking, a slight look of panic on his face. He quickly shook it off and turned on his normal boss mode, leading us through the airport towards our luggage and an awaiting car reserved for us. It took a while for us to get to our hotel on the south side of Manhattan, but I wasn’t complaining as I got to see so much of the city on the way.

Coming from Chicago, I wasn’t blown away by the towering buildings and the busy streets, but it was really amazing to see so many famous sites I’d only known through tv shows or movies. I made a note of the top things I wanted to do before we left, trying to think of something for the pair of us to do together.

We arrived at a luxurious hotel and I let Mr. Hill check us in while I marveled at the rich, old-world interior of the lobby. Soon enough, we found ourselves in a well decorated room with a huge canopied bed and a wide window that overlooked the city. Flopping down on the bed, I gave a deep sigh, sinking into the pillowy mattress below me. Thinking I needed to invest in a new bed when I get back home, I turned to my side just as I felt the mattress thud once more as Mr. Hill laid down and joined me. I just held his gaze for a minute before he spoke.

“Well, boy, I say for tonight, we get some food and sleep. Tomorrow is gonna be a long day of meetings and I want us to both be rested. Got to make sure we make All Tech look good.”

I just gave a tired nod of understanding as he called the lobby and ordered us some room service. After quick showers for both of us, we were enjoying our feast in bed, satisfying at least one of the types of hunger I felt at the moment. With the pair of us sitting under the covers, I couldn’t help but wish that this was my life. I wanted to be both Mr. Hill’s boy and his boyfriend. As we settled in for the night, I made a promise to myself that tomorrow, regardless of how things went at the meeting, I’d bring up my feelings for him, even if it made the rest of the trip awkward. I had enough money to get another room if need be, but I had hope that he’d feel the same way. As I crawled into bed, I noticed he was already asleep, his gentle breathing echoing around the room.

“Goodnight, Benjamin,” I whispered to him, before rolling over and joining him in slumber.

***

Turns out, I shouldn’t have worried at all about the meeting. Mr. Hill had given me plenty of time to look over and memorize the proposal details and between the pair of us, we nailed the presentation and won over the other members of the group. As we were leaving the board room, Mr. Hill looked to me with fire in his eyes, “I think this calls for a private celebration, don’t you think, boy?” he asked, whispering in my ear.

A quick taxi ride later and I stood in the bathroom of our hotel room, looking over myself in the huge mirror. I barely recognized myself anymore. The hair on my chest and around my cock was thicker and darker than ever before, as I hadn’t trimmed anything since starting with Mr. Hill. I’d also put on a few more pounds from our weekly meals of meat and potatoes and I looked far more like a stockier, shorter version of Mr. Hill. However, the biggest change came from what I wore.

Around my neck sat a hefty leather collar, with loops of metal around it which made me think it was close in function to the restraints on a dog collar. Around my upper chest I wore a well-fitting, metal and leather harness that crossed over and down along my stomach, latching on to the waistband of the leather jockstrap now covering my crotch. The pouch was held to the waistband with heavy metal snaps for easy access to everything and all together, it was actually really comfortable.

Mr. Hill had told me to clean myself and put everything on for him as soon as we got back, with him slowly stripping for me before shoving me into the bathroom with my things. Looking over myself one last time, I took a deep breath and walked back into the bedroom and stopped in my tracks. Mr. Hill stood just at the foot of the bed, his towering frame standing out even in the slightly dimmed light of the room. He wore a heavy pair of black jeans, though the tough fabric did little to hide the huge bulge I’d come to know. Over his hairy chest, he wore a simple leather vest, that was open and exposed his hairy, barrel like chest and well-padded stomach. On both arms, he wore leather bands across his thick biceps, and both of his feet were in chunky, military like boots.

“Get on the bed, boy,” he growled out. Even with his dominant demeanor, I could see the hint of approval and pride in his eye as he finally got to see me in all of the gear I brought. I climbed up on the bed and sat on my hands and knees, doing my best to show off my ass for Mr. Hill.

“Fuck yes, boy, that’s what I like to see,” I heard from behind me followed quickly by a loud slap as he smacked my cheeks, exposed in the leather jockstrap. I remembered my first night with Mr. Hill at his house and braced myself for another intense slap, but I was surprised to feel the gentle kneading of his hands on my ass next. I lost myself in the massage and gave a loud moan as I felt his tongue reach out and make its way over my overly sensitive hole.

He spread apart my ass further and shoved his tongue in deeper, opening me up far more than I was use to. My whole body shook from the intense experience, made even more amazing as I felt the coarse hair of his mustache tickle over the cleft in my ass. Every once in a while, he punctuated the rim job with a heavy slap on my cheeks and after a solid ten minutes of this, I was writhing on the bed, ready for more. Mr. Hill must have noticed this as he finally pulled away, admiring his handiwork as he looked over my stretched open hole.

I heard the squirt of lube behind me and the next thing I knew, I felt the heavy impact of him hitting my lower back with his huge, meaty cock. He hit me with it a few more times before I felt his hefty cock waiting at my entrance. I braced myself for him, but it didn’t come.

“Tell me what you want, boy.”

“Please sir, I want you. I want you to fuck me and use me however you want. Whenever you want.” I wasn’t sure where the words came from, but I knew I meant them.

“Good boy,” he said, gently running his hand up and down my back. I wasn’t expecting him to thrust in so quickly and I gave a sharp cry of pain, as I’d never had anyone fuck me as large as Mr. Hill. As he quickly sunk his nine-inch cock into me, my cries turned into a deep groan, as the mix of pain and pleasure overtook me. I was conscious of all the noise I was making, but I didn’t have to worry for long as I felt him bring something up to my mouth and shove it in.

At first all I could notice was the soft cotton on my tongue, but that was quickly replaced by the overpowering aroma of sweat and cum, as Mr. Hill put my filthy, cum rag briefs in my mouth to shut me up. I knew exactly what to expect from the flavor of them, as I’d indulged myself with several sessions with them ever since Mr. Hill had let me jerk off again. I’d never experienced anything like it, as I was simultaneously disgusted with myself, but deeply turned on by how slutty the whole thing made me feel.

I felt Mr. Hill reach up and clasp his hand over my mouth, keeping them in place as he continued to fuck me hard and deep, sawing his hips in and out in a steady rhythm that rocked the bed beneath us. I was disappointed in myself, as I knew I wouldn’t last much longer, from the incessant pressing of his cock on my prostate and the briefs in my mouth overpowering all of my senses. I could feel my cock pressed up against the supple leather of the jockstrap beneath me and with every thrust from Mr. Hill, my cock rubbed up against the pouch, adding another layer of friction to the already overwhelming sensations across the rest of my body.

“Oh yeah, boy! I can feel your ring getting tighter. You’re about to cum aren’t you, slut?” he yelled behind me, and all I could do was nod.

“Fuck yes! Don’t worry, I want you to let it all out. Let sir fuck the cum right out of you,” he spoke just next to my ear, as he now held me even closer as he jackhammered his dick into my well fucked hole. He rarely got this verbal, but it was having a huge effect on me and I could feel the warmth in me spread further. Thinking quickly, I unsnapped the clasps on the jockstrap and felt my cock swing out of the pouch seconds before I unloaded onto the bed below me. Thick streams of cum shot from my cock, spurred on by Mr. Hill as he unleashed his own load deep inside of me. He grasped the band of my jock and pulled me tight in one final thrust as he gave way to his own pleasure, groaning loudly as he came.

As we came down from our individual highs, I sunk back into the bed. My hips no longer lifted up and I felt my crotch hit the bed, meeting the sticky, cooling puddle of cum I’d left there. Mr. Hill also slumped over in the bed, rolling off my back and splaying his limbs out across the bed, his arms coming to rest across my back as we both took a few minutes for our breathing to return to normal.

I sat there, my whole body still warm in the afterglow of sex and I propped myself up on my elbow, taking in the sexy man beside me. He had his eyes closed, and his thick chest rose and fell with each deep breath he took. I reached out with my other hand and gently swirled my fingers through his hairy chest, playing with his hard nipples and enjoying the small sounds of pleasure he was giving me. As I sat there, I knew that I wanted more with this man and remembering my promise to myself, I spoke up before I could really stop myself.

“I think I’m falling in love with you Benjamin Hill.”

Mr. Hill shot up in bed, all the contentment drained from his body as he now sat rigid, a look of panic and what I was sad to see looked like regret, edging into the emotion of his eyes. I wasn’t sure what was happening, but I sat up with him.

“Sir, I’m sorry, I shouldn’t have said that without talking to you before,” I said as I reached out a hand towards him before he smacked it away with a force I wasn’t expecting.

“No!. Just…just don’t touch me!” he said, in almost a shout as he got out of the bed and turned to face the window. However, I could see the look of horror and disgust on his face as he did so and I could feel my own emotions getting the better of me. A wave of anger and confusion hit me as I really thought we were finally getting closer and I lost it.

“Fine.” I said, speaking to the back of his head at the moment. “Look, Mr. Hill, I don’t know what is going on here, and I’m sorry if I got the wrong impression about us, but this is ridiculous,” I said as I edged nearer to him.

“I’ve tried for weeks to get closer to you, tried to ask personal questions, and you always shut me out, or there was some convenient excuse to avoid me. But right now, I want the truth.” And I steeled myself to ask the question I was now so afraid to ask.

“Do you feel the same way?”

I waited for a few moments in silence, watching his body shake as he remained quiet. I gave a slight huff as I turned towards the bathroom having gotten my answer, when I heard a loud crash behind me and I swiveled around just as Mr. Hill hit the floor. I raced over to his side, “Oh god, Ben?” I asked, gently shaking him. His eyes were open, but I could tell they weren’t really focusing on me and he looked a bit lost. I continued to shake him gently.

“Ben, can you hear me?” I said, the panic now starting to creep into my voice as he tried to speak, but I could tell something was wrong. His words were weak and jumbled. I ran to the nightstand and immediately called 911, barely registering the woman’s words on the other end as she told me help was on the way. All I could do hold Mr. Hill’s head gently in my lap. I sat there, crying next to him as I waited for someone to come and help, just hoping that I wasn’t going to lose him.