Bobby was strolling the downtown streets, craning his head upward in awe at the incredible height of the office towers above him, when he bumped right into Reginald Howard.
“Hey, cowboy, better watch where you’re going.” Reginald laughed, taking hold of Bobby’s substantial biceps with a firm grip.
Their eyes met, and that was it. Bobby took off his cowboy hat and began to apologize in a rush, while Reginald stood with a quiet grin and surveyed this teenage hunk in front of him.
“You can call me Reggie. Or how about
boss?
Want a job?” he finally asked when he could get a word in.
Bobby had to say yes. He was in awe of the handsome young city slicker in the fancy suit and tie. Reggie Howard was suave and tanned with perfectly combed blond hair, a smooth white smile, and soft brown eyes. The dude seemed to be everything Bobby was not, mature for his age, confident, and rich.
Bobby immediately moved to Reggie’s sprawling ranch. On the outskirts of Houston not far from Bobby’s own small hometown, it was light-years from the life Bobby had led so far. Bobby had ostensibly been hired to care for Reggie’s stable of blue-blood horses, but it took Reggie less than twenty-four hours to offer Bobby added duties.
“Would you like to earn a regular bonus?” Reggie asked. It was Bobby’s second day on the job and Reggie had strolled out to the horse stalls to check up on his teen employee.
“Sure,” Bobby agreed enthusiastically. He was eager to please his new boss.
Reggie’s suave grin remained in place as he pulled the mystified youth over to an abandoned stall, freshly bedded with redolent straw. He was still smiling as he gently pressed Bobby’s shoulders down, compelling him to kneel in front of him. Reggie gazed down at the look of innocence on the young cowboy’s face and realized he just had to shove his dick between the lush, parted lips.
Bobby was taken completely by surprise as his new employer unzipped his fancy pants and pulled out a swollen dick. Bobby’s blue eyes grew wide as he gawked at the stiffening meat waving in front of his nose. Bobby could smell it, clean but musky like a man’s dick should be.
“Come on, Bobby. Lick it. Open those sweet lips and suck dick. I know you’ll like it,” Reggie urged, shoving his hips forward and rubbing the hard flesh against Bobby’s cheek.
Bobby had no qualms about doing just that. Although it would be his first time, he wanted to please Reggie, and he was springing a boner of his own just smelling the big one in his face. He opened up his mouth and closed his eyes. He shook all over when the warm dickhead plunged between his lips.
He gagged, and choked at first, then slurped it up, revelling in the silky feel of it, the hardness and the sticky taste of stuff oozing out of the slit on the bulbous head. He reached out and clutched at Reggie’s firm butt. It was meaty and full, pumping steadily as the businessman drove his dick in and out of Bobby’s mouth.
Bobby was possessed by a passion he hadn’t realized he was capable of. He ripped down Reggie’s pants and underwear, his hands roaming all over the man’s crotch and ass. He moaned as he rolled Reggie’s big balls in his hands, slid his fingers between Reggie’s parted thighs, and found the warm flesh between his clamped butt cheeks. Reggie had a big butt, although it was hard with muscle. Bobby avidly stroked the down-covered cheeks, but his attention was centered on the dick in his mouth. It was stiff as a fencepost and rapidly plying his tonsils, oozing pre-cum continually.
“Good job, Bobby,” Reggie huffed, his breathing as rapid as his pistoning dick.
He gazed down at the cowboy on his knees in the horse stall. His thick mane of auburn hair was in disarray, his cowboy hat discarded on the floor. Bobby’s full lips were spread wide, Reggie’s glistening shaft drilling in and out. Bobby’s eyes were closed, which Reggie found fetching.
Reggie realized he probably had a virgin, and he was intrigued by the very thought of it. He wanted Bobby naked, and he wanted his butt. He wanted it, so he took it.
“Get your clothes off, Bobby. I want your sweet ass,” Reggie ordered breathlessly, pulling his dick out of Bobby’s mouth.
Bobby opened his eyes and looked up at his blond employer. Although he was only about a half dozen years older, he seemed to be a man where Bobby felt like he was still a boy. He could not disobey him, and besides, he was getting paid. He reckoned he had to oblige.
Bobby rolled backward onto the hay and began to strip. He lifted his legs and pulled off his cowboy boots, then skinned out of his tight jeans and underwear. Reggie hovered over him, stroking his dick, his own pants and silk underwear down around his knees. He was still wearing his dress shirt and tie, since he had been on his way to work. He licked his lips as Bobby lifted his muscular thighs to pull off his underwear, displaying a rippled stomach with a rock-hard dick bouncing against it. But what sent a shiver of lust though the oil tycoon was the glimpse of Bobby’s snug asshole between his upraised thighs.
Reggie shoved his pants down to his ankles and dropped to his knees over the half-naked Bobby. The cowboy was attempting to remove his shirt when Reggie seized Bobby’s hips and shoved them backward. Bobby’s white butt rose up in the air between them. Reggie looked down at a pair of hairless buns, equally hairless balls, and a swollen dick. He gasped at the sight of that puckered asshole, quivering as Bobby’s body shook with a mixture of fear and excitement. Reggie had to touch it. He poked a finger at the hole, ramming the digit between the tight ass lips and into the heated love tunnel beyond.
Bobby squealed like a stuck pig. His thighs were crunched up against his chest and his shirt was tangled around his head and shoulders. He couldn’t see what was going on. But the sensation of air on his naked ass and the painful aching of a finger rammed up his tight chute had been pleasing in a nasty way.
“I ain’t never done it before,” he shouted. His voice rose several octaves with the sharp ache of that intrusion, though his dick continued to jerk lustily between his spread legs.
Reggie snorted out a rude laugh. He was intrigued by the feeling of his finger inside Bobby’s tight hole and the way the cowboy was squirming. He didn’t want to hurt the teen, but he had to have that butthole. He spat down on the hairless opening and worked the saliva into Bobby’s hole. This elicited a low moan and a grunt from Bobby’s shirt-entangled face. That was better than the yelp he’d hollered earlier, Reggie thought.
“I’m going to bust this cherry of yours today, Bobby. Your new duties will include getting a dick up the butt on a regular basis,” Reggie drawled.
Bobby managed to untangle his shirt from his body and gazed up at the blond businessman. He was so damn good-looking, his amber eyes were kind, and he seemed a great dude. Reggie’s finger was beginning to feel good up Bobby’s throbbing bunghole. Bobby impulsively clutched his own thighs and pulled them apart, thinking that he could open up his asshole a bit that way. It worked.
“Yeah, cowboy. Spread those legs. Open up your tight slot for me,” Reggie crooned, his powerful lust negating any inhibitions he had about porking a virgin teen who worked for him.
He spat on the hole again and worked in another finger, the tight orifice expanding with the parting of the cowboy’s thighs and Bobby’s increasing stimulation. Still, it was a tight fit, and Reggie loved every spasm of the clamping anal lips over his probing fingers.
He had to have his dick up there. “I’m going to fuck your virgin ass. You want that?” he asked, his soft eyes boring into Bobby’s glittering blue ones.
Bobby nodded silently, not yet able to speak the nasty words out loud, although Reggie’s lewd language was exciting him.
Reggie had not lost his head entirely. He reached down into his tangled pants and found his wallet. Inside he had a condom, which he quickly pulled out and rolled over his dick. Then he scooted up between the eighteen-year-old’s parted thighs and pointed his rod directly at the spit-wet butt entrance. Two of his fingers were buried to the knuckle, but even together they weren’t as large as the shaft eager to replace them. Reggie withdrew his fingers, watching as the stretched ass ring clamped back down tightly. He was shaking more than the young cowboy as he planted the head of his dick at the snug fuck entrance. He gobbed more spit down, the juicy lube landing on his dickhead and the puckered asshole. He began to shove, but it was so constricting he slid away, his dickhead rubbing against the butt crack raised up in front of him.
Reggie grabbed hold of Bobby’s hips and held them firm, again pointing his dick at the hole between the quaking buns. “Hold still. I’m going to pork your ass, no matter how tight a fit it is!”
Bobby put his hands on his own butt cheeks and yanked them apart, hoping in that way to open up for the dick poking at his hole. He wanted it; his asshole was hot and throbbing and it felt great when Reggie shoved at it with his dickhead. But he wasn’t sure if the big thing was going to fit up the tight tunnel of his virgin asshole.
Reggie held his dick against the squishy fuckhole. The puckered lips were beginning to open up, and he pressed just a bit while he allowed Bobby to squirm and groan beneath him. He held the teen’s ass firmly, and all that wiggling served to drive the tip of his dick halfway past the muscled assrim. Bobby grunted loudly and really began to squirm.
“Oh man, your dick is so big. It feels like you got a fence post up there!” he squealed.
“I don’t even have the head inside yet. Your butthole has gotta open up more than that,” Reggie groaned. His excitement increased as his dickhead was squeezed by the snug orifice clamping over it. He couldn’t control himself any longer. He took a deep breath and shoved.
Half his dick went up Bobby’s butthole in that one thrust.
“OOOHHH! NOOOO! Goddamn! Your dick is up my asshole!” the young cowboy shouted, his face beet red, his eyes squinted in pain.
Reggie was nuts now that his dick was buried in Bobby’s butt-oven. He began to fuck the lad with abandon, driving his rod deep, pulling almost all the way out, then ramming back in. Bobby kept up a staccato grunting of both “noes” and “yesses” while tossing his head from side to side and holding his own butt cheeks apart for the first porking of his life.
Reggie pummelled Bobby’s butt, driving himself to a wild orgasm. The clinging fuckhole massaged his bone unbearably, squeezing it with irresistible heat. He yanked it out at the last minute, whipped off the condom, and ejaculated all over the cowboy’s ass crack. Bobby had been driven close to the edge himself and when he looked up and saw Reggie’s swollen dickhead spewing nutcream all over him, his own balls emptied. His aching asshole clenched around the emptiness it suddenly felt. The rampaging dick that had just been inside it was now shooting gooey cream while Reggie rocked with gasping emotion.
Bobby’s dick hadn’t even been touched, but the sensation of a gut-wrenching assfuck had been enough to get him off. Lying back on the clean straw, his body sprawled out beneath his boss’s spewing dick was an awesome moment. Bobby felt as if he could come forever.
But he had to dress and get back to work. Reggie kissed him affectionately and promised him a fat bonus for his extra labor. Bobby rubbed his aching butt and grinned as he returned to work.
Bobby may have been innocent, but he knew what was going on. His boss was paying to fuck him. Yet, that was fine with him. Bobby worked hard on the chores, feeding and exercising the horses, and was paid for that. Why shouldn’t he get paid to spread his legs for the boss? Especially since they both liked it so much.
But that was only to be the first of his new duties. Reggie began to show up at any time of the day, or night, and with a cool grin and wink offer the teen cowboy another bonus.
“How about a bonus boner up your tight hole?” Reggie chuckled as he entered the cowboy’s room above the stables in the middle of the night. Reaching beneath the young man’s blankets and searching out his hot ass, he dug into the snug cotton underwear until his hands were deep in the teen’s butt crack. With condom-covered dick he fucked Bobby’s ass for half the night.
He surprised Bobby out in the open, beneath the cover of the cottonwoods beside the creek that ran through Reggie’s sprawling ranch. Home early from the office in Houston, he discovered Bobby hard at work. Reggie shoved the lad down in the grass and lifted his legs to screw the living daylights out of him with his pounding cock.
Bobby always obliged, and always shot a load of his own when Reggie sprayed him with his juicy jizz. He loved the feeling of that dick stretching his tight hole, and the sight of Reggie’s big bone spewing milky cum all over him. The bonuses he received after these bouts of love-drilling were large, and Bobby felt as if he was adequately satisfying his handsome boss.
A few months passed before there was an alteration in their schedules. An added duty was imposed on the cowboy. He found himself entertaining young wealthy friends of Reggie’s on weekends. Bobby would be asked to take the young men for rides. At first he just assumed it meant with the horses. After he had taken a redheaded Houston acquaintance out on a sunny afternoon, they had returned to find Reggie waiting in the barn for them.
“Lance here is offering a real nice tip if you show him your other area of expertise.” The blond businessman smirked.
Before the innocent cowboy realized what was happening, Reggie had him stripped and crouched on his hands and knees in the straw.
“What a bubble-butt! How’s the cowboy’s asshole? Nice and tight?” Lance asked, his own clothing discarded alongside Reggie’s.