They took turns banging the sprawled cowboy, one hard dick after the other, complimenting Bobby on his tight sphincter and his beautiful big cowboy butt.
That was the beginning of a constant supply of young friends Reggie brought out to the ranch. Bobby always received a generous tip after the hard fuckings, which he didn’t mind at all. The truth was, he was in a constant state of expectation, never knowing when the next hard dick was going to ream his increasingly hungry butthole. Bobby understood what was happening to him, and he didn’t mind that at all either. He was becoming Reggie’s personal whore, and the boss was his pimp. The thought of it was nastily exciting. He trusted Reggie, and gave little more thought to it.
Bobby’s butthole was growing accustomed to all the dicks plowing it after a long hot summer getting fucked, yet it remained a tight slot for Reggie and his pals. Bobby had also learned to be more than obliging, waving his can in front of the men with unbridled enthusiasm, shooting his load even if they didn’t bother with his dick.
Reggie began to bring Bobby up to the main house and asked him to spend afternoons sunbathing and swimming in the spacious pool. He claimed he wanted Bobby to be tan, and he wanted him available in case they had company.
Bobby was out on the pool deck on a pleasantly warm September afternoon when he experienced his first gang-bang. He was half asleep, having worked hard all morning with the horses. Lounging by the pool, he was wearing only a small g-string that Reggie had laughingly insisted he wear when swimming. The strains of country music twanged from nearby speakers. A sudden commotion disturbed the cowboy, who glanced up groggily from his face-down position on a lounge chair.
Loud whistles greeted him as a half dozen young men in suits spilled out onto the pool deck. “You were right, Reggie, your young cowboy has the sweetest-looking butt in the south of Texas,” a tall dark-haired stranger commented, moving toward the awakening Bobby.
“But can he take dick up the ass?” Another sturdy-looking Houston businessman chortled, he too moving in on Bobby.
“What’s going on, boss?” Bobby barely had time to sputter as the men descended on him. Reggie was right there with them, and he was smiling down at Bobby, his soft expression putting the young man at ease.
“Open wide, Bobby. No sense talking when you can be earning your pay.” He chuckled. He was already fishing out his fat dong, and before Bobby could utter another word he was feeding it between Bobby’s lips.
Hands were all over the sprawled cowboy, hands on his back, his arms, his waist and thighs. His legs were pulled apart, and hands slid over his browned butt cheeks. More whistles accompanied the groping hands, and lewd jokes.
“What a pair of butt mounds. Smooth and clean, and wow! Get a look at that hairless little asshole!”
“Yeah! Finger that tight slot. Spread his butt wide!”
Bobby was grunting with the shocking abruptness of the experience, his thighs shaking, his body in sudden heat from the probing male hands all over him. Someone was prying at his bunghole with a pair of fingers, and now that he had some experience down there, he was able to lift his butt and unclench his hole to ease the violation.
He was rolled over onto his back by the myriad hands on him. His head hung down and Reggie’s dick slowly slid into his wide-open throat. Bobby snuffled over the big dick, tasting the copious supply of pre-cum that his boss fed him. At the same time his legs were held up and apart by stroking hands.
“Rubbers, dudes. Everyone put them on or there’s no cowboy butt for any of you!” Reggie laughed as the guests crowded around Bobby.
Out of the corner of his eye, Bobby saw suits, pants, and ties flying as the businessmen disrobed in a frenzy of lust for the hired hand.
A whole slew of messy lube was wiped over Bobby’s cowboy hole. The warm pit was almost immediately filled with another pair of digging fingers that were screwed around inside him in all directions, stretching his fucktunnel and teasing his prostate. Bobby was ready when the first dick entered.
“This teen hunk is not only damn handsome, like you said, Reggie, but he obviously likes his butthole poked. Look at the stiff whanger on him, y’all!”
Hands began to stroke and tease his dick, the tiny g-string he was wearing pulled to the side. His balls were tickled and teased along with his dick, and so many sensations were bombarding him at once that he couldn’t hold back. An eruption of juicy seed unloaded all over his chest.
“Hot damn! We fucked the jizz right out of him. I gotta come too!” someone yelled. Bobby was in a fog, his gullet stuffed full of Reggie’s fat throbber, his own dick spurting, and now a dick up his butthole was exploding with a load of cum.
“My turn,” someone else claimed.
Another dick entered, Bobby’s squishy hole wide-open by then. For a good half hour the six men took turns plying his sweet butt while he lay back and snuffled over Reggie’s throat-stroking meat. Reggie caressed the cowboy’s lips, cheeks, and hair while he fucked his face and encouraged his friends to fuck the young stud’s asshole. Bobby floated in a dream of male hands, mouths, and odors. All the while it was Reggie’s crooning voice rising over the others. Bobby had never yet felt so completely immersed in sexuality. He was an open pit for dick, and he held nothing back.
They were finally finished. Bobby was lifted up and dumped in the cool water of the pool. He was exhausted, but the water reinvigorated him and when he rose dripping and naked from the water, Reggie approached and hugged him close, pressing a goodly amount of hard cash into his hands.
“You did well, Bobby. I think I’ll swing a lucrative business deal now that my friends are in a good mood.” He slapped Bobby’s naked ass and winked.
Bobby felt great. The money was awesome, but Reggie’s appreciation was even better. He realized he was growing very fond of his boss.
The autumn approached and a string of clients moved through the ranch, Bobby taking the men out for rides on the Texas ranch. He always ended up offering his bubble-butt or his lush mouth, or any part of his body the men craved. He was the one fucked, and he did enjoy it. But when the last of the leaves were falling and December rolled around, Reggie sprang quite a surprise on his teen escort.
It was a bright day, crisp and cool, when Reggie ordered Bobby to saddle the horses up for three. Bobby was a little surprised when Reggie arrived with someone who had to be as young as Bobby. He didn’t look like the usual customer or business acquaintance.
“This is our new hand, Terry. He’s going to be helping you out around here. We’ll go for a ride and show him the place this afternoon.”
Reggie was grinning. He had a hand on the youngster’s shoulder, and for a brief moment Bobby was almost overcome with jealousy. Was he going to be replaced by this new youth as Reggie’s cowboy escort?
But then Reggie’s soft eyes met his. There was trust there, and a twinkling of humor. What was going on? Then Bobby had a flash of inspiration. Reggie was almost shoving the young man forward, as if offering him to Bobby. That was it!
Bobby suddenly smiled at the young cowboy, who must have been about the same age as him. Blond like Reggie, but with a buzz-cut that showed off a nice scalp and a plump, attractive face, Terry was staring with wide eyes at Bobby, as if he wanted to eat him up. Bobby glanced down at the cowboy’s crotch, and sure enough under his clinging jeans there was a growing bulge.
“Uh, hi, Terry. Saddle up and we’ll show y’all around.”
The three of them rode out over the ranch under a blue December sky. Their breath steamed in the air as they chatted amiably. It seemed Terry was from a small Texas town just like Bobby. He was anxious to please, and Bobby felt a sympathy for Terry replacing his earlier jealousy. When they reached the creek and a grassy knoll perfect for fucking, Reggie dropped down from his horse and nodded to Bobby.
By then the young cowboy knew his boss well, and he realized that showing the newcomer the ropes was something Reggie wanted to happen right now, right in front of him. Bobby grinned, the blond teen smiling back. They tethered the horses to the bole of a cottonwood, and Reggie stood aside and nodded to Bobby.
Bobby faced Terry. He grabbed the young cowboy by the shoulders and shoved him to his knees.
“When the boss has fellas here, you gotta treat them right. Get my drift, Terry? Let’s see if you can suck.” Bobby was laughing as he glanced over at Reggie, who was watching with interest.
“Test him out.” Reggie laughed back. “He’s all yours, and he is new to this.”
Bobby was suddenly possessed by lust. He gazed down at the young man who was shaking with nervousness, but grinning with an equally powerful eagerness. On the surface, nothing was any different. Bobby did what his boss asked, with whoever his boss asked him to. But a rush of blood to his stiffening cock and his flushing face warned Bobby there was a difference. Another change on the ranch was happening. Terry was it.
Before Terry could say a word, Bobby fished out his dick and stuffed it into the blond’s gaping mouth, knocking off his cowboy hat. Terry gagged a bit but then sucked Bobby’s prick right to the nostrils, reaching out and grabbing hold of Bobby’s sturdy hips.
Reggie had stripped quickly and was already stroking his own stiff dick as he watched the two young men go at it. Bobby enthusiastically face-fucked the cowboy Reggie had newly hired. He recalled all the times he had been in a similar position, only he had been the one on his knees. Bobby was so excited he could barely control himself.
Bobby shoved Terry back on the dewy grass, sprawling over him with his thighs on either side of the cowboy’s face, driving his dick down into the soft gullet of the surprised but willing youth. He reached back and stripped off Terry’s jeans and cowboy boots while Terry struggled and mewled and pretended to be reluctant. The look in his eyes told a different story, and the hard dick that Bobby found also revealed Terry’s true feelings. Bobby stroked the boner, playing with the plum head and working an ooze of pre-cum out of the slit. He got up and ripped his own clothes off, watching as the moaning cowboy on his back in the grass shook all over. Terry licked his lips as his eyes roamed over Bobby’s muscular body and tight hard ass. Terry reached up and grabbed the smooth asscheeks, his own lust now kindled to uninhibited heights.
“You might like that ass, but it ain’t for you today. I’m intending on showing y’all what you gotta do to please the boss and his buddies. So open up those legs and get ready for dick up the butt.” Bobby grunted, stroking his flushed dick over the cowboy’s face.
“We gotta do this for Reggie’s friends?” Terry began to question. But Bobby threw one of Terry’s legs up, exposing his hairless hole, and rammed a finger right up it. Terry moaned with both surprise and aching pleasure.
Bobby held the naked cowboy on his side, one thigh shoved toward his chest, Terry’s hard dick and dangling balls within easy reach, and his quaking assrim wide open for Bobby’s exploration. Reggie came over and bent down to squirt a stream of liquid lube over Terry’s ass crack, and then even rolled a condom over Bobby’s stiff dick for him. They exchanged a grin, then Reggie moved back and squatted on the grass to watch.
Bobby felt a rising sense of power possess him. He was in control of the young cowboy naked beneath him, even if Reggie was really in control of them both. His position on the ranch had changed again. Bobby’s gaze dropped down to Terry’s open ass.
Lube glistened all over Terry’s unblemished white butt cheeks. The small anus clutched tightly at Bobby’s fingertip digging into it. Bobby dug deeper, past the knuckle, then added another finger while Terry grunted and shook from head to toe.
“I’m going to fill your tight asshole with my hard dick, and you’re gonna love it, trust me,” Bobby said, gazing into Terry’s eyes.
“Yeah! I want your dick up my hole, fuck my tight ass,” the cowboy suddenly urged, a grin on his own face. Bobby grinned back. But his next action wiped the smirk right off the cowboy’s face. Bobby jerked his fingers out of the Terry’s clamping hole and replaced them with his stiff rod. Gritting his teeth against the spasms of Terry’s constricting ass lips, Bobby shoved, his dickhead entering, then his shaft right behind.
“YEAH! A tight asshole! What a ride,” Bobby yelled out.
But then Bobby felt a body behind him. The sight of the two young men about to fuck had proved too much for Reggie. He shoved his own hard, condom-covered dick up Bobby’s asshole even as Bobby was ramming deep into Terry’s hole.
Bobby was in heaven. For the first time he realized he was in love with Reggie, and was happy to have Reggie’s dick ramming his asshole. But the feeling of his own dick up a tight hole was something new and wonderful. They rocked back and forth in the grass, pumping and grunting, dick up squishy hole, while the December sun splashed down on them. The cold air could not compete with their hot young bodies and they soon grew bathed in lather. Reggie pounded up Bobby’s ass while Bobby drilled Terry under him. Finally Reggie shouted out his arriving orgasm.
As Reggie filled him with his heavy load, Bobby knew complete satisfaction. As he shoved his tongue between Terry’s sweet lips and felt Reggie’s lips on his neck, he realized his life was perfect. He blew up Terry’s ass as Terry’s dick spewed on Bobby’s belly.
Reggie left the two young cowboys to clean up, hopping on his horse with the cum drying in his underwear. “Expect company later this evening. Some acquaintances are arriving for dinner and I want you two to dress up in your best cowboy gear and join the party.”