From Boss to Boyfriend, Chapter 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 over my interior window. 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.