My first time hooking up with a boy on a work trip

(All parties are 18+)

It was the fantasy any daddy dreams about. I was in town for the weekend, staying at the Hilton. Convention and meetings all day. I went down to the pool in the morning to squeeze in a swim I barely had enough time for. And stepping out into the hot Arizona sun, he was the first thing I saw…

He was wet, sprawled out on a lawn chair, his lean, smooth body still glistening in the sun. Messy hair slicked back, but a light brown tangle of it falling into the mirrored lenses of the aviator sunglasses that were almost too big for his sweet face. As I walked by I couldn’t even tell if he was looking at me. His pink lips scowling at the bright sun. He had on a green pair of board shorts, hung low past his narrow, but defined abs. And his toned legs were angled just enough for me to catch a glimpse of the paler, less tan skin underneath. Almost enough to see…

He shifted, cutting off the view, and moving to fold his hands behind his head. I walked past, my shadow crossing his face, long enough to make him stop frowning, and… was that a smirk?

I tossed my shirt on a chair a few down from his. And got into the pool, plunging into the cold water. As I made a lap, circling back, I casually found a way to scan the row of chairs. Gone. An empty wet lawn chair. Of course, shaking my head. Not even the chance to watch his little butt walking away from me.

A few more laps and I got out to walk towards the hot tub. A glance at my watch told me I should already be toweling down and headed back. A couple was getting out and as they passed my vision, a pair of blue eyes, hovering above the bubbling water, locked with mine. There he was. Aviators casually removed, narrow shoulders flexed as he leaned back in the jacuzzi, arms resting on the ledge. He was still here, alone in the tub. And if I didn’t leave right now and get dressed, I was going to be late for my first meeting. I moved to join him.

His blue eyes were still watching. He held the stare as I stepped into the water and sat down across from him. It was definitely a smirk on that cute angular face. I returned it. The boy smiled, flashing white teeth behind those pink lips.

I realized right then, I was going to miss my meetings today.

***

He smelled like chlorine as he passed close by me in the elevator. Giving his head a toss, that floppy damp hair of his drying and getting blonder by the second. I was nearly a foot taller than him. God, he was cute. His T-shirt was sticking to his lean body, making me wish he was shirtless again. I smiled to myself. Patience. He’ll be naked soon enough.

He caught me watching him again and gave a grin. I tapped my floor and the doors started closing. I stepped closer to him, tempted to start pushing my tongue into him right here in the elevator. He was smirking again. “Skipping out on your meetings today, daddy?” He said it playfully as our elevator reached my floor.

“Something far more important came up.” I fished out my keycard. “You remember the room number, right kiddo?” I continued the naughty roleplay that he’d decided to start us down. Had to pull him away from randomly trying it on the nearest door, and he turned it into a game of keep-away. I was enjoying his laugh, catching my breath as I opened the door to my hotel room and let him inside. The door closed, locking.

He held that playful stare of his, grinning. Then his hands were on my chest, craning up to kiss me. I pulled him against me, my bigger hands on his small butt. He moaned softly. I moved to kiss his neck and he moaned louder, wrapping his arms around my shoulders. I could read his mind, picking him up into the air. He laughed again, wrapping his legs around my waist. I could feel his hardening cock through his board shorts and playfully dropped him to the king sized bed.

He pulled the t-shirt off over his head, I admired his toned, lean chest again. Before I could start taking off mine, he was pulling off the green swim suit and kicking it off to the floor, completely naked, still damp from the pool. He gave me a sultry look, my cock stiffening immediately. He crawled forward, arching his bubble butt into the air. The perfect view of his face and ass all at once. And then he was pulling down the waistband of my trunks.

I felt the head of my throbbing cock sink into his warm, wet mouth. Those pink lips wrapping around the thick helmet head. I breathed a deep growl of a sigh. And he looked up at me with those blue eyes. And then got down to sucking daddy’s cock.

He made a loud gag, his tight, warm, wet mouth pulling up and off of my swollen cock. I watched him cough, sniffling as he looked from the dripping, sticky cock that glistened in front of him, then up at me. He grinned. God, those big blue eyes. I smiled back, reaching out to wipe away the tear on his cheek. He moaned at the touch. My fingers in his almost dry, strawberry blonde hair. He reached out and played with my erection, still wet from his mouth.

“So big,” he whispered, giving me a hungry look. I went from a caress to a firm hold, guiding his cute face to the head of my cock, and watching it disappear as he closed his eyes, unconsciously opened his lips, and took it back inside his mouth.

He was new to this. He told me it wasn’t the first cock he’d sucked. But it was definitely bigger than he’d experienced so far. Our age difference excited him too. I surprised him by going in deeper, feeling my thick helmet head sink and abruptly stop at the back of his mouth. He started to gag again. I brought up my other hand to firmly hold his head.

“No,” I instructed, my voice deep, louder than his playful whispers. “All the way, c’mon.” His eyes fluttered open, I sunk forward. And felt my cock enter his throat. “There we go. Attaboy.” He was fighting hard not to pull away, tears running out again. My thumbs caught them. We held the stare.

He exploded up off of it, gasping for air, smooth chest heaving. A messy trail of saliva connecting his lower lip to the tip of my cock. He caught his breath, his eyes still on the target. I gave him a few more encouraging words. Reassured him he was doing a good job.

Then it was his turn to surprise me. He gripped the base, spat on the head, and engulfed his mouth on it again, gagging loud, letting my hard cock push down into his throat. “Oh good boy…” I praised. And he began to bob and swivel, fucking his throat on my cock.

My balls were tightening, he was dangerously close to making me cum right then and there, straight down his throat and into his tummy. He was making the naughtiest sounds, foam flooding his mouth and practically pouring down his chin and onto his chest. He sank down impressively deep, and stared up with those big, now very red and wet, blue eyes. I held the stare and gave him a wink. He pulled back, big smile on his face as he played with my cock in his hands.

I reached for one of his ankles and his face got excited as I manhandled him onto his back. His narrow arms going behind his head as he watched me fold him over, legs in the air, that tiny tight hole of his exposed.

And I brought the head of my throbbing cock to tap against it…



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