Best Little Whorehouse

Jay Starre

Bobby Burns had just turned eighteen when he met Reginald James Howard III. It was summer, and he had taken a break from his job on a ranch to visit the big city of Houston, Texas.

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.