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.
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.