pup's life
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2020-06-01 23:59:19

    After the retirement party had died down, and everyone had gone back to their offices to resume their work, you saw your opportunity.  This was his last day on the job after 30 years with the company.  Surprisingly, no one was lingering in his office.  At 56, Johnson was still a young man and far too active to become one of those retirees who sat in front of the TV and became overweight.  You’d heard he was starting up his own consulting business that he’d run out of his home for the time being.  You walked to his office doorway, expecting to find him putting his things in boxes.  Before you could notice he was on the phone and retreat quietly, you knocked on his door.  He looked up from the phone and motioned you to come in as he finished his call.

    “…yeah.  It was nice.  Everyone was there…..Yes, some people said some very nice things.  I think I’m going to be missed around here.  I’m sorry you couldn’t be here……I know, I know.  Work comes first.  Listen, someone just came in to see me.  I need to go.  I’ll see you when you get back from L.A.  Bye.”

    “I’m sorry, Mr. Johnson.  I didn’t meant to intrude.”

    “It’s okay, Bill.  I was just talking with my wife.  She wanted to find out how the party went.  Since she couldn’t be here.” and he added halfway under his breath, “…ever.”

    Trying not to react, you continue the conversation.  “Now that you’re retiring from the company, I’m sure that’s going to change.  You’ll be able to spend so much more time together.”

    He smiled at me, but it wasn’t a happy smile.  It was more of a grimace.   And the sarcastic tone of what he said next confirmed my suspicions.  “That’s not likely to happen.  You see, my wife’s job is incredibly important to her.  She’s just been relocated to Los Angeles, where she plans to be for at least two years.  So, you see, not only is she going to be working for two more years, we won’t even be in the same city.  Happy Freakin’ Retirement, Dave!” referring to himself in the third person.  Then suddenly, his demeanor changed and he appeared cheerful again.  “I’m sorry, Bill.  I didn’t mean to unload all of that on you.  What’s on your mind?”

    “Well…”  Suddenly, you weren’t as confident as you’d been when you were walking down the hall to his office.  “Uh….I…uh…”   Johnson’s warm smile - in addition to making your dick twitch - made the situation a lot less nerve wracking.  “Mr. Johnson, rumor around the office is that you’re going to be starting up a consulting business.”

    “Ah.  I see word travels fast!  Yes.  I am.”

    “I was wondering…well…I was wondering if you were going to need any help.”

    “I hadn’t really thought about it.  But I suppose I will.  Why do you ask?”

    “I’m sure you’re going to have to interview people.  But I’d like to throw my hat in the ring for a job with you.”

    Johnson appeared shocked that I’d even ask.  “I thought you were happy here at UniTech, Bill.”

    “The company’s been good to me.  But I feel like my job has run its course.  Everyone in the next position up the ladder is so far away from retirement.  I don’t feel like there’s any room for advancement here.  Besides, you’ve always been so good to me.  I’ve learned a lot about the business from you.  Not only do I want to keep learning more, but I want to repay you for all of your kindness

    A smile formed on the older man’s face.  I must’ve said something he needed to hear after a disappointing conversation with his wife.  “I’ll tell you what, Bill.  If you’re sure you want this, I’ll make you this promise…  You don’t even have to interview.  You can be the first official employee of Dave Johnson Consulting.”

    “Really?!  That’s fantastic!  Thank you so much, Mr. Johnson.  You won’t be disappointed!”  I wanted to hug him.  Actually, I wanted to do a lot more than hug him.  But if I played my cards right, maybe that “more” would come later.

    “I know I won’t, Bill.  I’ve had my eye on you,” my dick twitched in my slacks again. “You’re a good worker and a good guy.  We’ll do great together…really get this company off the ground.  Now, I have to warn you, I’m not going to be in a position to pay you well, at first.  But if you stick with me, I think the money will come later.”

    This was my chance.  If I was going to make a play for Johnson, he just gave me an opening.  “Mr. Johnson, money isn’t the only thing I’m interested.  I think there’s a lot more you can give me.”

    I had thought he was flirting with me but his reply made me think he was completely oblivious.  “Now, I know knowledge is invaluable.  But a young guy like you is going to want to get paid and be able to live comfortably.  I’ll be able to give you that eventually.  I just want you to go into this with both eyes open and realize we might be struggling at first.”

    Before I spoke again, I leaned back and looked down the long hallway, no one was coming.  It was now or never.  “As long as we’re struggling together, I’m okay with that.  But no, Mr. Johnson.  I’m not talking about knowledge, either.”

    “Okay.  I’ll bite.  If you’re not talking about money or knowledge, what exactly is it that you think I’ll be able to give you?”

    No time for nerves now.  Just go for it, Bill…  I walked around his desk and leaned over him.  He looked up at me, quizzically.  I could see the confused expression on his face, wondering what in the hell I was doing.  Without a word, I reached down with my right hand and grabbed his crotch, rubbing it and getting a feel of what seemed like a decent-sized flaccid penis.  At the same time, I leaned down and planted my lips on his before he could react to my fondling.  At first, he did nothing…stunned, I’m sure.  But eventually, he began to kiss me a little bit.  So as not to overwhelm him, I pulled back after a few seconds.  Waiting for what his reaction would be.

    For a moment, he sat back in his chair, wide-eyed and apparently confused.  “Uh….wow!  Bill, I had….I had no idea.  Uh, I think we might be able to work out a payment plan for your salary, after all.”  With that, I exhaled and all of my nerves went away instantly.  A smile formed on Mr. Johnson’s face.  “In fact, I’m starting to think that a big part of the job initially is going to involve a lot of work late into the night.  You’ll probably find yourself needing to stay over at my house pretty often.

    “I don’t have a problem with that at all, Mr. Johnson.”

    “Bill, please.  I think it’s time you started calling me, Dave.”

    “Sure thing, Dave.”  I smiled at my big gamble with Dave Johnson paying off.

    “By the way, Bill.  I’m really anxious to get this consulting business up and running.  Do you think you’d be available to come by tonight so we can get started?”  He winked at me and furtively brought his hand to his crotch and gave it a squeeze.  I licked my lips appreciatively and realized that this was going to be the beginning of a beautiful partnership.

    From Boss to Boyfriend, Chapter Five

    This is the fifth chapter of a story that I’ve been continuing on my Patreon. Now that chapter six is available to patrons, I’m posting this one publicly.

    Chapters: One | Two | Three | Four | Five

    “That’s it,” I groaned, my thick black-haired fingers clenched down on the head bobbing in my lap, “suck that fat dick, Avery.”

    He paused and tilted back to look up at me over the rim of my round gut, stretching out a blue polo. That pair of quizzical eyes met mine and I almost blushed. “Sorry, Jon,” I chuckled, loosening my grip. “I’ve had a weird week.”

    The young man dragged his lips back along my prodigious length until my glistening mushroom popped out of his mouth and he smirked, “You can call me whatever you like, sir.”

    I shook my head and tousled his hair. “Just keep sucking, boy,” I commanded in the stern voice that never failed to drive this burgeoning Broadway star wild. I leaned back and grinned as his mouth engulfed me once more.

    I’d met Jon back when he was stuck in the ensemble of some boring revival. Couldn’t recall which show, but my eyes were glued to the slender dirty-blond boy’s ass the second he stepped on stage. After kissing my date goodnight, I managed to pick him up at the stage door and drag him back to my place. I got my money’s worth for that price of admission.

    But even Jon, talented as he was, couldn’t get my mind off that wonderful and horrifying night. It wasn’t the first time a bout of my classically midwestern sincerity had gotten me in trouble, but Avery’s stunned, panicked look was hard to forget. We’d salvaged the night, but long after he was snug and asleep against my chest, I was still playing that moment over in my head.

    I’d startled awake, flat on my back with Avery sinking that tight ass down over my morning wood, and gladly busted a nut before reality sank back in. I gave him a sheepish kiss after dressing and jumping in a car back home to get ready for work.

    Just the thought of that perfect ass made me throb between Jon’s lips, feeding him a gagging gulp of precum. I grinned and grabbed him roughly to fuck that pretty face into a proper mess. My whole body spasmed with urgent pleasure as the haunting, lustful memory of Avery drove me into a primal frenzy of domineering strength until I erupted onto my cocksucker’s struggling tongue.

    “Oh fuck,” I howled, stoppering my lips before Avery’s name could sneak back out between them. “Swallow it all, faggot,” I said with a snarl, smacking the back of Jon’s head insistently. “Show me how you crave that daddy dick, boy.”

    Jon moaned around my member, his ecstatic harmony to my demeaning melody, and licked the meaty rod clean. Not a single drop escaped his hunger for me. This is what I love, I told myself. It’s simple. It’s satisfying. I didn’t need to be messing around with a rich daddy’s boy in a city full of eager sluts. Life was good.

    But still I woke the next day rubbing my morning wood into a pillow, aching to sink into the waiting warmth of Avery’s snug rear. “Fuck,” I muttered, irritated with the fantasy my sleepy brain so readily summoned for me.

    With a huff and a glance at my clock, its green light abrasively bright in the pre-dawn hours, I slumped back into bed and pumped my fist beneath the sheets. I closed my eyes and tried to imagine anyone straddling me, anyone but him bouncing atop my cock. But it just took a moment of weakness for me to let him in, to imagine Avery gasping with pleasure in my lap, for me to erupt like a milky volcano.

    A sliver of light from the horizon glimmered in the cooling splatters of jizz in my fur. My chest rose and fell with recovering breaths. Looking down at it, I felt a swell of pride at the amount. It was like my nuts were working overtime since they emptied into Avery.

    I waddled to the shower, washing it all down the drain in the rush of warm water. My half-hard member twitched at the thought of pinning that smooth skin to the tile, of making him mine at absolutely every opportunity. I hadn’t had it this bad for someone in a long while.

    I managed to lose myself in the routine—shave, brush teeth, check notifications as I walk, drink coffee, eat a bagel, tap out a few replies on the train, put on a smile in the office—and it was such a relief. For the better part of an hour, I didn’t have to think much about anything at all.

    And then Avery smiled at me, perfect pearlescent teeth shining as he chirped, “Good morning, sir.” His glittering green eyes followed me like a pair of lost puppies. He ran his slender fingers through that cascading cinnamon hair and my own hand twitched to touch him as I marched past.

    “Good morning, Avery,” I replied curtly, “in my office, please.” He practically jumped out of his chair to nervously follow in my wake. I took a deep breath as I stepped into my office, straining to turn my expression to stone. “Shut the door, Avery.”

    He obeyed as I turned to face him, a mischievous grin on his cute lips. He asked eagerly, “What can I do for you, sir?”

    “I think we should slow down,” I spat the words before I could stop myself, wincing at Avery’s crestfallen look. “There’s a lot going on coming up and we can’t be distracted by—” I paused, gesturing my hand at the space between us, “—this.”

    We stood, his pain raw on his face and mine bricked behind a stoic wall, in silence for a long moment before I continued, “You’re a cute guy, but you don’t know what it’s like to need a job. If I fuck up my career by banging my employee, I can’t just coast on family money for the rest of my life. If anyone found out about us…”

    Avery straightened as I spoke, that preternatural confidence of a person who never wanted for anything returning. He even smiled, perfect teeth gleaming, before he asked, “Do you know where my dad met his first wife?” I shook my head, and he said, “She was his secretary. And my mom?” He hardly paused this time. “His general counsel. And his third wife? A model who did the cover of one of his magazines.”

    “And in this analogy… I’m your father?” I vacillated between a smirk and a frown. He rolled his eyes and stepped toward the door to pull the shades. I raised a hand, protesting, “Wait, people might think we’re…” I trailed off as Avery unbuckled his belt and pulled down his suit pants and briefs to expose his perfectly round, smooth ass to me.

    He stepped to the floor-to-ceiling window looking out over Midtown, planting his hands on the glass as he bent forward. With a grin and a glimpse at the throbbing knob bulged halfway down my thigh, Avery said, “Come fuck me, Mike. You can go as slow as you want; I’m not in a hurry.”

    I was without words, so I chose action. I closed the distance between us, fumbling with my fly, and sank into his slicked hole with a groan. It wasn’t going to be that easy to get rid of this one.


    The road trip that summer while I was back from college took a turn…  Admiring what a man I’ve become during those first two years away from home - reaching over from the driver’s seat to run his hands over my muscular arms and shoulders and telling me how nicely I’ve filled out and bulked up, becoming a nicely handsome dude instead of just a cute teenager…then letting his hand drift down to my upper thigh for a series of squeezes - turned into me telling him that I’m just trying to keep up with the example he’s set.  I even reached over to place my hand on his knee and looked him square in the eye, showing him that, not only was I no longer a cute teenager, I wasn’t shy or bashful anymore either.

    Our mutual admiration society as we barrelled along the highway toward the beach turned into him pulling off the road into one of those hidden emergency pull offs in the median of the highway that cops usually use to stake out the road for speeders.  With the car shut off and only silence hanging in the air between us, we looked at each other.  Both of us knew what we wanted to happen…what was destined to happen.  But, neither of us seemed to have the guts to make the first move.  “Fuck it!” I thought to myself and leaned across the console between the driver’s and passenger’s seat to press my lips against his.  That opened the floodgates in a way I certainly didn’t expect.  Before I knew it, our clothes had come out and we’d found ourselves in the backseat…he on his back against the seat and me on top of him, nestled between his spread hairy legs,  We were still making out like if we didn’t, we’d both stop living.  All I knew is that I didn’t want this to end.  That, and I was horny.  Hard and horny as hell with desire.

    Our kiss broke and I looked into his eyes, silently questioning if we could go “there.”  He inhaled sharply, nodded slightly and bit his lips.  That’s all that I needed.  We were gonna fuck…right there in the backseat of his car.  And I was going to be the top in this situation.  Admittedly, it wasn’t happening in any of the thousands of ways I’d fantasized about it over the years.  But, it was about to happen.  Even if the rest of my summer break from college wasn’t worth shit and a litany of terrible things happened from next week until I had to return to campus in early August, this would be the best summer I’d ever have.


    We shouldn’t have been where we were right now:  a hotel room, getting dressed after an intense fuck followed by a tender make out session in the shower as we lathered each other up and washed each other off.  But really, we were too far down the rabbit hole to stop things now.

    The time to put a stop to it was a year ago…after that first time.  A late night talk had gotten deeper than I expected.  Our soul-baring had turned emotional…and our emotions drove us to kiss tenderly.  Tender quickly deepened into passionate and urgent.  The next thing I knew, we were tearing each other’s clothes off.  That first time, we just blew each other…then swore we’d never let it happen again.

    Of course, just two days later, it did.  Over the next few weeks, it was the same pattern of wash, rinse, repeat.  We’d give in to our basest desires, feel guilty, swear that was the last time, and then, inevitably, wind up naked together again, quenching the desire that it seemed like only each other could quench.

    Soon, the facade of guilt faded away.  We wanted…no.  We NEEDED each other.  There wasn’t any use pretending to regret what was happening between us anymore.  It wasn’t long after that that we progressed to fucking.  Some people say that sex usually ruins things.  It seemed to be the opposite for us.  It only served to deepen our connection.  Our bodies seemed to be meant for each other.  We seemed to know exactly what would make the other feel good or what the other wanted.  It was an almost mystical connection.

    Truthfully, I was starting to fall for him.  I was certain THAT would be a bridge too far.  I was beginning to have to work hard to control the way that I would look at him…not just in everyday situations were I had to act “normal” around him, but even when we were having sex, I had to be careful not to let my feelings show on my face.  It was starting to stress me the hell out!  When we were in bed or the shower or a hot tub or wherever it was that we were having sex, we were meant for each other  But, when it came to love…  Well…I was less certain of the strength of our connection.

    That’s why it was a complete shock to the system when he grabbed my arm as I turned to open the hotel room door so we could step out of the bubble we’d created together and get back to the real world.  “Curt, wait.”

    “Yeah?”  I stopped with the door halfway open.  I let it swing back shut and turn to face him.  God, those steel blue eyes of his…  I wanted to dive into them and never come up for air!

    “I-I’ve got something to say to you before we leave.  It’s something I’ve been wanting to say for a while now.  I’m not sure how you’re going to feel when you hear what I’ve got to say.  But, I can’t put it off any longer or I’ll never be able to live with myself.”

    “Shit!” I thought to myself.  “He’s about to end things!  So much for our connection…”  Out loud, I encouraged him to get whatever it was off his chest.  “I’m sure whatever you’ve got to say will be fine.”  I even smiled at him.  God, I was a fool!

    He raised his eyebrows and widened his eyes.  “We’ll see if you still feel that way in a minute.  You see…  What I wanted to say is…  Uh, Curt…”  After another brief pause he said the words I never thought I’d ever hear him say.  In fact, I didn’t understand what he meant at first.  “I’m in love with you.”

    Well…  It wasn’t “it’s all over between us.  We’ll have to figure out how to act around each other in social situations going forward.”  I was relieved.  But, I’d completely misunderstood what he was trying to say.  I opened my arms, leaned forward, and gave him a hug.  As I pulled back from the hug, I gave him a quick kiss.  “I love you, too!”

    He seemed dumbfounded by my reaction.  “No, Curt.  I mean, yeah.  I love you, too.  But that’s not what I mean.  I mean, I’m IN love with you.”

    What a sight it must’ve been to see realization wash over my face and my body in real time.  “You’re IN love with me?”

    “Yeah.  I am.”  He looked uneasy, still uncertain of what my reaction would be.  “I know we said we were just keeping things light and casual…just being there for each other, getting our needs taken care of in a way that they weren’t getting taken care of before.  But, things have changed for me.  I tried to stuff my feelings down, but that isn’t working anymore.  If hearing me say this is too deep for you, we can end it right here, right now.  I won’t be happy about it, but I’ll understand.”

    I couldn’t stop smiling.  I reached up to rub the side of his sexy, chiseled jaw.  “If I ever needed proof that you’re the one for me, I just got it.”

    He smiled and laughed softly.  “What do you mean?”

    “We’ve been on the same page without realizing it.  Things have changed for me, too.  I haven’t said anything because I thought knowing how I felt would scare you off.”

    He ran his hand through his hair and laughed.  “Life’s fuckin’ funny sometimes.”

    “You know what I think?” I asked with a shit-eating grin on my face because of what I knew I was about to do.

    “What’s that?”

    “This.”  I wrapped my hands around him, letting them graze over the muscles of his back that I’d come to know so well.  I leaned in for a soft, soulful lingering kiss.

    When we came up for air, he leaned in for another quick kiss before begrudgingly pulling away from me.  “We’d better get going.  They’ll notice we’re both gone if we don’t get back.”

    “Yeah…” I said, longing in my voice as he moved past me to open the door.  This time, it was me reaching out to grab his arm.  “Wait.”

    “What’s up, Curt?” he questioned.

    “I’m in love with you too.”

    He smiled broadly, setting off those sexy eyes and chiseled jaw of his.  Then, he bit his lip and leaned in for one last kiss before we really did have to leave the room.

    Things were already complicated for our relationship.  We had to take every precaution so no one in the office would find out.  After all, it wouldn’t be good for either of us if word got out that going-through-a-messy-and-protracted-divorce head of the office was screwing around with one of the guys in the mail room.  But now that we knew how we felt about each other, complicated was an understatement.  But damn if the boss wasn’t worth every bit of hardship!