THE SINGING COWBOY

Rob Rosen

Hundred bucks,” said the man on the other end of the line.

“But I’m not a singing cowboy,” I protested.

“Ad says cowboy for hire,” he replied. “I’m trying to hire you.”

I sighed. Yes indeed, I had taken an ad out. After all, jobs for honest to goodness cowboys were few and far between. Still, this wasn’t what I had in mind, not by a long shot. “But you want an entertainer, mister; I’m a cowboy. I herd cattle. I tend to cows and horses. I don’t sing to neither one.”

His sigh echoed my own. “But you are a cowboy, right?”

I nodded, even if only for my own benefit. “Uh-huh.”

“Hundred and fifty,” he barked. “Take it or leave it.”

Since all rotten things travel in threes, my last sigh was the loudest. “Where and when, mister?” I asked, resignedly. “And please tell me it’s not first thing in the morning.”

Well, first thing, no. But not too much later, as it turned out. Guess seven-year-olds get bored after ten in the morning. Go figure. And, to be quite honest, I could sing. Sure, I’m no Gene Autry, but ain’t nobody gonna cover their ears, I figured. And as for that Benjamin and a half, it’d pay for groceries until a real gig came along. That or a decent paying rodeo. Either way, it was easy money.

Or so I thought.

Though it did start off easy enough, with me showing up right on time even. Place was some big ranch miles and miles out of town. Father of the birthday boy rented the whole kit and caboodle. Even had a nice mare for me to ride once I got there. Jason, the newly crowned seven-year-old, had one too, just a smaller version of my own.

He sat on his little filly alongside my mare while I did some fancy rope tricks my daddy had taught me, the same ones his daddy had taught him. The kids down front oohed and ahed and clapped with childish glee, Jason included. That oohing and aahing amped up a notch when I started galloping around them, my lasso high overhead, the rope nothing but a blur once I sent it spinning, a boy down front lassoed a moment later. Funny thing was, no cowboy worth his boots ever did this sort of stuff, not in real life, but, truth be told, I was having fun.

That is, until… “Now time for some singing!” shouted the father, who clearly didn’t know a good act when he saw one. Not even when the oohing and aahing turned to boos and catcalls. I mean, what little kid wants to hear a grown man sing instead of performing rope tricks?

Still, that’s what I was getting paid to do, so that’s what I’d do. Plus, they’d already wheeled the cake out, and I knew that no amount of roping was gonna compete with that, at least not for long. Now all I had to do was sing a couple of old-fashioned cowboy songs, ending of course with the traditional “Happy Birthday to You.”

Except, I never got that far. No sir, no how.

See, while no one covered his ears, the horses, as it turned out, didn’t have the option to, Jason’s horse in particular. Guess my yodel spooked the filly. Though it was a mighty good guess considering that when I hit my highest register, the young horse hit the ground running.

Up the filly jumped, Jason’s face going from bemused to terror-stricken, worse so once his mount charged through a fence of bushes and on to points unknown. I of course, being the good cowboy that I am, instantly took chase. Through the bushes I went, my mare whinnying and snorting as she catapulted her wide expanse of chest through the dense patch of green, brambles and leaves and twigs raking across my denim shirt.

I held on tight, sweat suddenly trickling its way down my face as I veered my mare in Jason’s direction. We were in a field now, so there was no way for me to corral the young gal, to maneuver her into some sort of dead end. Instead, I galloped ahead and quickly found myself alongside them.

“You okay?” I hollered to the kid above the din of hurtling horse hooves.

He was holding on tight, legs gripping the filly’s sides. “No,” he whimpered, tears streaming down his face.

So much for that happy birthday.

I galloped closer now, the two horses barely a couple of inches apart, both of them charging at full steam. My legs grabbed on to my mare as I let go of her reins. I quickly reached across and grabbed the filly’s. I tugged with all my might, eyes in a concentrated squint, until she gradually slowed, snorted, and then, at last, came to a complete stop, kicking up dust all the while. Take that, Gene Autry.

“That was some riding, kid,” I said, with a wink.

Jason wiped the snot from his nose. “Really?”

I nodded and tousled his hair. “Sure as shootin’.”

I wasn’t certain he understood the compliment. Not that it mattered, though, because all of a sudden his father came driving up from our left, another mare from our right, both sides quickly converging on the pair of us.

“Looks like the cavalry is a comin’, boy,” I made note.

He giggled. “Too late, um, Mister Cowboy, sir.”

I shrugged. “Better late than never, I s’pose.”

The father came to a screeching halt by his son’s side and hopped out of the car fast as lightning. “You scared the filly,” he snarled, staring my way as he helped his boy off his horse.

I couldn’t help but chuckle. “You’re welcome,” I said in reply.

He hugged his boy as he set him down in the car. Suffice to say, I never got my thanks. Not even a tip. Instead, he handed me my cash and stormed off, muttering that he should never have listened to his wife. He and the boy drove away, leaving me in a cloud of dust.

Well, not just me, really.

“I dunno,” said the stranger, who’d galloped up to see what all the fuss was about, once the dust settled. “I kind of liked your singing.”

I squinted his way and sucked in my breath as my eyes landed on his, on so much blue you could just about take a dip in them, the sapphire orbs sitting atop an aquiline nose, plump lips below and scruff-dense cheeks that would’ve made the Marlboro Man jealous. A wave of amber hair flowed out from beneath his Stetson and a matching down poked out from the collar of his denim shirt.

“Um, thanks,” I managed to reply. “Sorry you missed my encore.”

He laughed; the sound like the wind whipping through the prairie grass. “Oh, I reckon I caught it, mister.”

I held out my hand as I trotted over. “Mark.”

He took my mitt in his, flesh meeting up with flesh as a white-hot bolt sizzled up my spine. “Jesse,” he informed me. “Pleasure.” And talk about your gross understatements. “I caught your act, by the way. Where did you learn all them rope tricks and fancy riding?”

A flush of red worked its way up my stubble neck. “Daddy was an all-state rodeo champion three years running. Granddaddy topped him by a year.”

“And you?”

That blush of mine widened. “Just the one, but that was a bunch of years ago.”

It was then I noticed that his hand was still in mine, the horses nuzzling each other like old pals. Reluctantly, I released my grip as I again stared into those mesmerizing eyes of blue. “Care for a ride?” he asked.

I laughed, nervously. “I think I already had one.”

He nodded. “This one will be gentler,” he replied. “If that’s how you like it.”

The words were innocent enough, but they certainly didn’t come across that way. In any case, my nod echoed his and the horses took off, side by side, at a slow, easy trot.

The land stretched far as the eye could see, cattle in the distance, a few rugged hills here and there, green on top of green, if you forgot about Jesse’s sea of blue. Which, of course, was impossible to forget. “This your ranch?” I eventually asked, pushing down on the stiffy that had formed in my tight jeans the moment I laid eyes on him.

“Nope,” he replied. “I manage the place.” He glanced over just as my hand left my crotch. He grinned and then stared back out into the distance. “Five hundred acres, by the way, give or take.”

I blew an appreciative whistle. That much land for a ranch was a rarity these days. “Big property.”

He nodded and mimicked my hand gesture on his own crotch. “Big,” he replied, again looking my way, the smile wide, white, and beguiling, dimples appearing within the scruff.

My grin matched his, my hand back on my denim-encased prick. “Big, huh?”

His nodding picked up steam as the horses rounded a bend, the path blocked on three sides by rough terrain and rocky hillsides. “Mighty big.” He pulled back on his reins, his mare stopping in place, whinnying as she did so. “And gettin’ bigger by the second.”

My own horse came to a stop. “I reckon we’re not talking about acreage no more, are we?”

He slowly unzipped his fly. “Wanna make a bet on that?”

My cowboy was going commando, his cock, with great effort, extricated from inside his jeans, the mighty steed rearing once before coming to a wobbling halt. I licked my lips as I stared at the glistening head. “I think I might’ve already won it.”

I hopped off my horse and ambled over to his, my ambling impeded by my rigid prick begging for its own release. Jesse hopped down and closed the gap between us, his hands around my waist, yanking me in as his cock pressed up tight against my belly. “Howdy,” he rasped his lips on mine in a dazzling flash, that ocean of blue at last spread out before me.

The kiss made my knees quake and my belly rumble. The fact that my zipper held was testament to one Mister Levi Strauss. When our lips at last parted, I breathlessly echoed, “Howdy.” I then popped open my fly and managed, with rather great difficulty, to release my impossibly stiff prick, adding with a relieved sigh, “Better.”

He stared down. “Much.” His grin returned, even more seductive than before. “You ever get ridden sidesaddle, Mark?”

I grabbed a hold of his tool. It throbbed and pulsed and promptly leaked in my grip. “’Course I’ve ridden sidesaddle.”

He took hold of my crowbar of a cock. My eyelids fluttered upon impact. “Not ridden. Get ridden.”

He stroked as I stroked, while his words swirled around my head, soon enough lining up like the tumblers in a slot machine’s. “Wait a sec,” I finally replied, gazing downward as our thick tools got mutually worked. “You want to fuck me while we ride?” I scratched my head. “Sounds dangerous.”

“Says the man working a child’s birthday party.”

“Good point,” I allowed, squeezing the head of his bulbous prick as I breathed in the musk and sweat of him. “Good point indeed.”

He reached into his back pocket and retrieved one lone rubber and an equally lone small bottle of lube. “And that point’s gonna be buried far up that pretty little ass of yours soon enough.”

I moaned at the thought. “You do indeed come prepared.”

“That’s my motto,” he boasted, releasing my prick so he could get undressed.

“I thought that was for the Scouts.”

He shrugged. “Cowboys, too.”

“Yep.”

“Yep.”

And, nope, it didn’t take two randy cowboys all that long to undress neither. Meaning, one minute we were in jeans, cocks poking out (like way out), and the next we were stark naked, hard as granite, covered in a sheen of sweat and making out until the cows came home, which, judging by the fiery orb in the sky, wouldn’t be for hours yet.

He hopped on his mare, legs dangling over the side, beautiful dick pointing sky-high. I stared up and smiled at the sight of him. “You do this to all the cowboys around these parts, Jesse?”

He shook his head in earnest. “Just the singing ones, Mark.” And then he reached his hand down and helped me up, until the two of us were riding that mare sidesaddle, back the way we came, this time heading farther away from the main house.

“Not what I imagined when I started the day,” I freely admitted as I watched him stretch the rubber down the length and breadth of his meaty prick before lubing it up but good.

He laughed, cock swaying from side to side as he did so. Me, I was already sidling over and up, aiming my portal at his wide expanse of dickhead, all while balancing on the horse, who, for her part, ignored our shenanigans as she moseyed on along. Wasn’t easy, no, but well-trained cowboy that I am, it didn’t take too long for his cock to be up my ass, one hand wrapped around my dick, the other balancing backward on the mare, with me holding on to both as best I could.

I ground into him and let out a howl. “Now that’s some fancy trick riding if I ever saw it.” I moaned in delight as he pumped my prick and my ass, all of it aided and abetted by the bouncing ride below.

The horse whinnied, I grunted, and Jesse panted, while we rode and fucked, fucked and rode, my ass and dick getting a mighty fine workout. I’d ridden in every conceivable position before, for money, for fun, for work, but this, this was something brand-spankin’-new.

“Fuuuck,” I panted, balls bouncing as I rode him like a bucking bronco.

“Yeah,” he whispered in return, his mouth on my neck, sucking away, the come building as he jacked and jacked and filled my throbbing hole until I was sure his dick would come popping out the front of my mouth.

When the mare took off in a trot that was about all she wrote for us. By then, he was battering up against my farthest reaches something fierce and I was… “Close, Jesse. So. Fucking. Close.”

“Mmm,” he hummed. “Come with me then.”

I nodded and gulped, sweat flinging off my forehead. “Gladly.”

The mare hopped over a log, and that was that. Come flew up and out, drenching the ground beneath us. In fact, it would take weeks for me to regain my protein store. As planned, he came as I came, his moan joining mine as both our heads flew back and the charger beneath us suddenly halted in her tracks.

I chuckled as he shook the last vestiges of spunk from my steely prick, my entire body trembling now, legs quaking as he teased my now-sensitive head. “Well,” I managed to squeak out, “that was some ride.”

His laughter joined mine. “Plenty more where that, pardon the expression, came from.” He paused and rubbed my belly. “If’in, I mean, you’re looking for some real cowboy work.”

My heart nearly leapt to my throat. “Singing included?”

He shrugged from behind me. “Optional, I reckon.”

Then it took some wrangling, but eventually I was behind him instead of on top, my arms wrapped around his waist as we galloped off into the sunset (or what would eventually be just that). My cheek was pressed to his broad expanse of back as I sang Gene Autry’s “Back in the Saddle Again.”

Seemed befitting, all things considered.