Chapter Three: The Pool Party
"You weren't shitting me? You haven't been fucked by a man before?"
Whalen was standing just inside the door of his bedroom—a large room dominated by a gigantic bed. Dillon hadn't failed to see the restraint leads curled on the floor at the four corners of the bed. He had stripped down to his briefs as Whalen had ordered him to do. Whalen was dressed in a lounge suit, though, of some sort of diaphanous material that showed the red Speedo he was wearing underneath. This supposedly was a pool party, but they were in his bedroom. He was barefoot. He was in great shape for a man of his age and appetites for the good life. His "good life" obviously included a lot of painful hours in the gym. Appearances were everything in Hollywood.
Dillon had been the first to arrive and had been ushered right up to the bedroom. He assumed that his new agent, Whalen, wanted a crack at him before the pool party started and the guests started filing in. He'd been told to arrive an hour earlier than Scott had.
"No, I haven't," Dillon answered.
"But, in order to stay on my list, you'll—?"
"Yes, I understand."
"You'll be restrained. There won't be any backing out. If you wind up doing a lot of yelling for mercy, he's likely to like that and step it up."
"Uh, OK, I guess."
When Dillon had been spread-eagled, face down, on the bed, sans briefs, tied off at the four corners, and a wedge stuffed under his lower belly, Whalen opened the door and let a middle-aged man in who was big—as in close to, but not quite, obese. He was a good six and a half feet tall too, which, with his age, saved him from quite being called fat. He was nearly bald, with a fringe of reddish gray hair around his head. His face was craggy, but it had an aspect of command about it. He was wearing a dressing gown, but it was hanging loose on him and didn't hide either his reddish blond bush or his presentable erection.
"This is Mr. X, Dillon. You don't need to know his real name. All you need to know is that he's a big backer of movies and you'd be good to make a friend out of him." With that, Whelan left the room.
After a somewhat slobbering ass eating and opening exercise, Mr. X fucked Dillon doggie style, crouching high over Dillon's hips with his hands gripping Dillon's waist, and bouncing up and down on the young man's pelvis. Dillon had done what he could over the previous day and a half with a lathered dildo Scott had given him, but still the pain at first was excruciating. It got better, though, and Dillon got the inkling—as he had with the dildo—that over time it wouldn't be that bad at all.
Fighting through the pain, he concentrated on the phrases "big backer" and "make him your friend," and he put his acting skill into high gear.
"God, you're huge. You're killing me. Yes, yes, screw me to the bed. Give it to me. Give me your cum. Shit, you're a stud. Fuck, I'm glad my first time is with a stud like you?"
"Your first time?" Mr. X asked, with awe.
"Yes, my first time."
"Well, shit," Mr. X said and took it a little slower—was more solicitous at least at the beginning. He took his time getting inside Dillon, understanding now that the young man to be a virgin and having a hole tight enough to confirm that. He knew what he was doing, and his guidance to Dillon to relax and open to him—and how to do that—eventually worked. He obviously was pleased that he was giving the young man first-time instructions and benefiting from the tight fit.
He wasn't particularly thick or long, although Dillon had nothing with which to compare it to other than the dildo. And other than the opening to it, that actually was better with the real dick than the rubber one, there was little to prepare Dillon for the real dick. He controlled the dildo and could pull it out when it became too uncomfortable. It was just the point of it becoming too uncomfortable that Mr. X pushed his in further—and pulled it out further and then in deeper—and when he picked up the pace.
"God, you're sweet," the man exclaimed through gritted teeth, and then they were off to the races. Mr. X lost control and pounded Dillon's ass like he was a rent-boy. Dillon endured. This was just the beginning of his career.
With a yelp of victory, Mr. X gave Dillon his cum. Taking Dillon's word for it being the first time, there was no protection, so it had been skin on skin and cum in passage core. The man had pledged extra money to a movie deal Whalen was involved in for that extra privilege.
"Big backer; make him your friend," Dillon was thinking, as they were cooling down and Mr. X was going flaccid inside him, Dillon murmured, "I need you again. But not tied up like this. Untie me; let me make love to you. I want to learn to do it right. Teach me, Daddy."
Mr. X sighed through the second blow job Dillon had ever given a man, but Dillon was careful not to let him come. The man was sitting on the end of the bed, and Dillon climbed up into his lap, facing him, and swallowed the cock with his channel. Groaning to accompany Dillon's moans, the man clutched and spread Dillon's butt checks and pulled his passage up and down on the cock until he creamed Dillon again deep inside.
"He was very pleased," Whalen said, when the man was gone and Whalen had reappeared—this time still in the diaphanous lounge suit but not the red Speedo, which revealed, by the lighter area now not covered by the Speedo, the tanned body of the agent in erection. "I want to be pleased too before we go downstairs."
Dillon was kneeling at the end of the bed, facing the headboard, as Whalen, standing at the foot of the bed, fucked him from behind, one hand on Dillon's belly, pulling and releasing to match the rhythm of the fuck, and the other hand cupping the young man's chin and pulling Dillon's head back into the hollow of Whalen's shoulder. Whalen sucked on Dillon's earlobe as he fucked him, again bareback.
Dillon enjoyed this fuck more—indeed, he was feeling that he would increasingly enjoy the fucking as he did more of it. Whalen was younger and more fit than Mr. X was. He was more expert at working his cock inside Dillon to his pleasure, and there was more lubricant—Mr. X's two ejaculations—inside Dillon now to aid the slide of the shaft. Dillon was also beginning to get the knack of going with the rhythm of the fuck and manipulating his passage walls to make love to the invading cock. Whalen remarked on how Dillon was quickly improving his technique as they fucked on.
Whalen declared he was as pleased as Mr. X had said he was when he was finished—and Dillon again had given what he thought was an award-winning performance of wanting what he got and moaning deeply to it.
"Pick out a swim suit that fits—but fits tight—from that drawer over there and come down to the pool," Whalen said as he pulled on his own red Speedo under his lounge suit and left the room. Dillon hadn't come with a swim suit, apologizing and saying he didn't have one that met the specifications Whalen had given him. Whalen didn't seem to mind; he had plenty of swim suits in his guest room to hand out—as well as other forms of sexy clothes for young men.
Downstairs, on the pool terrace, about a dozen men, more of them middle aged than young, were milling around the pool, glasses and beer cans in hand, and eating off trays that a couple of young, cut men in Speedos were passing around. One of them was Scott. Whalen leaned over and whispered in Dillon's ear, "Tell Scott to lose the tray and then I want the two of you to do a couple of circuits of the pool. Then you can go into the pool and horse around with each other for a while. When I signal, I want the two of you to go back upstairs on the bed. Remember that these all are men who can promote your career. You'll pull a train, won't you?"
"Yes, sure," Dillon asked without knowing what that meant.
As Scott and Dillon walked around the pool, sometimes arm and arm, sometimes in single file and catching the eyes of men and smiling at them, Dillon saw that the rising star, Cory Corbin, who he'd lost his name to, was there. And he was busy. There was an older, chunkier but still hunky, and deeply tanned Western movie star, Fletcher Farwell, there, lying on a chaise lounge. Cory Corbin was straddling Farwell's hips. Both of them were naked, their Speedos on the stones beside the lounge bed. Corbin had the palms of his hands pressed into Farwell's beefy pecs and he was using the leverage of his feet on either side of the chaise to raise and lower his channel on Farwell's cock.
There was other sex going on around the pool too, but as Scott and Dillon dove into the pool and started tossing a ball to each other and then doing some wrestling, most of the eyes turned to them.
It was nearly a pied piper parade when Whalen gave the signal and Scott and Dillon got out of the pool, dried off and, at a signal from Whalen and accompanied by gasps all around, stepped out of their Speedos and went into the house and up the stairs to the bedroom.
The two of them lay on the bed on their backs on opposite sides. They embraced each other's heads with their hands and kissed as a progression of men stepped up to split their legs, move in between their thighs, and fuck their asses.