Disclaimer: This story is about men having sex with men. If that's not your thing or you're too young to read it, please leave now. The author has no knowledge of Ryan Phillippe's sexuality, nor that of any other famous personality mentioned here, and has written this purely as a work of erotic fantasy fiction. Enjoy!
RYAN'S HOLE
by Backlash29
Chapter 1: Grunt Work
As far as he could tell, Brady Jones had the greatest job in all of Hollywood. At 30, he was the assistant to a well-known and sought-after talent agent, Jerry Coswell. The job paid well, and provided him with infinite connections around Hollywood, where he hoped someday to succeed as a screenwriter. But it was the little "perks" of the job--the ones he never could have predicted--that made it so worthwhile.
Coswell & Sons (of which Brady's boss, Jerry, was the only remaining son) was a small outfit that represented a few dozen of the hottest rising stars of the last decade. Jerry himself was very infrequently around the office, as his role required him to travel extensively, schmoozing the talent he already represented, and attracting new business along the way. That left Brady and a staff of five other assistants to do all the "grunt work" associated with the day-to-day business.
In Brady's case, this entailed following the stars around and catering to their every whim: chartering flights when they needed to travel, handling their expenses and logistics when they were making a public appearance, and just generally making their day-to-day lives as glamorous people as painless as possible.
Brady knew going into this career that it would be a lot of hard work, and he'd have to deal with a great number of difficult, spoiled people. But he could never have predicted how rewarding the job would be, in areas of his life that weren't technically in his contract. For example, a significant number of the stars represented by his office required very low-profile hook-ups for sexual gratification, and as personal assistant to many of them, he had access to the Hollywood underground network of hustlers, hookers, call girls, rent boys, and escorts of every variety under the sun.
All of the "players" (as they were known) were known to be of high quality and very discreet. Their sexual health was on-record and checked regularly by doctors who were on the payroll of the agency. In short, a big part of Brady's job was assuring that his stars could get laid, safely and discreetly, anywhere and anytime they ever wanted. And the network was not only systematic and reliable, it was profitable as hell. Heidi Fleiss didn't have shit on this underground organization. Many of the players made over $200K per year. As a great-looking guy himself, Brady thought more than once about whether he should give it a try.
Most of the time, making these arrangements was as simple as hooking up straight male celebrities with a stripper for the evening when they were stuck in a distant hotel, or flying some beachy hunk to a starlet's remote shoot to fuck her silly in the evenings after a long day under the lights. Most players were based in California or New York, but there were several in the other states and in Europe as well, and regardless, all were familiar with the travel requirements of their chosen jobs.
Brady knew, as soon as he took the job, that he would be introduced to the gay side of this Hollywood lifestyle as well as the straight. Naturally, he was curious about which of their stars would request this style of service. Throughout his first year of employment at Coswell & Sons, however, none of the stars he was signed-on to assist had ever made such inquiries. Every once in a while the other assistants around the office would mention needing a gay or lesbian player to go to so-and-so, but it was rarely a star of any public stature or reputation. He figured, rightly, that many of their high-profile celebrities did in fact request same-sex hook-ups, but that for the sake of their reputation is was kept hush-hush among senior members of the firm.
Until that fateful day, in 1998, when Brady was 27 and still learning the ropes after a full year of employment, when Jerry Coswell invited him out for lunch.
"I need you to take over the Ryan Phillippe account," Jerry told him. "Alan's got too much on his plate, and I think I'm going to need him in Europe anyway for a while."
Brady was silent. This was a huge promotion; the next biggest star he'd ever helped out with was a two-month gig onsite with Selma Blair in San Diego. Plus, he wasn't sure he'd ever assisted anyone as purely beautiful as Ryan. He had always been jealous of Alan--his hot, forty-something straight co-worker--for having the excuse to cater to the gorgeous blond stud's beck and call.
"Do you think you can handle it?" Jerry asked. "Naturally, we can get rid of some of the smaller clients you're helping with in order to make time for this. Ryan Phillippe is a very big deal for this agency."
"No kidding," Brady mumbled, still in shock. "Hell, sure, I can handle it. It's an honor, really."
"Well, you do great work," Jerry told him. "That, and..."
Brady looked quizzically at his boss. He wasn't accustomed to seeing him at a loss for words.
"Well, uh..." Jerry stammered, then laughed nervously. "Well, Ryan has some special needs. Alan can fill you in on all this, or I can just tell you about it now."
Brady was up for anything, as long as it meant him getting this account. "Shoot. I can handle it."
Jerry took a deep breath. "You gotta keep this under wraps, obviously. The kid likes boys."
Brady's eyes widened. Had he heard him correctly? "He likes...boys?"
"Yes," Jerry said, matter-of-fact, and took a swig of his wine. "He likes them a LOT."
"No shit..." Brady let his mind wander to some evil place for a minute, then quickly re-focused on their discussion. "But...isn't he hooked-up with his co-star currently? I heard they were getting married." (At this time, Ryan and Reese Witherspoon were still just an item in the tabloids; it would be another year before their wedding and the birth of their baby girl.)
"Reese. Yes. Well...they work around that, I suppose. Many couples do." Jerry looked his assistant squarely in the eye at this point. "Listen, what they're up to is their business. It's not our place to gossip, or presume, or even really to observe. We're here to make them happy, and give them what they want."
Brady nodded, getting excited in spite of himself. "And in Ryan's case...?"
"And in Ryan's case, that means a lot of sex. With men. From what I hear, he's insatiable."
As it turns out, "insatiable" barely described it. In the first few weeks after getting Ryan's file from Alan, Brady was on the phone with players up and down the southern California coast, as well as a few "favorites" from out-of-town. On average, there were arranged visits to Ryan's Hollywood house every other day when he was in residence there, and when he traveled (unless Reese was with him) he generally took at least two players along.
Brady had access to all of the personal information about each player: Their stats, their kinks, their locations, their clean bills of health. Overall, Ryan seemed to prefer bigger, slightly older men who were moderately kinky and very well-hung. Brady's mind reeled at this. So far, he had been handling the paperwork only; Alan still managed the star's account. But all of that would be changing soon. Alan was traveling to Europe for an extended stay, which meant that Brady would finally meet his new client face-to-face.
"So, any last questions on Ryan?" Alan asked one night when they were working late at the office.
"Yeah, a few," Brady said. "When's your flight?"
"Tomorrow morning, first thing. So, you can ask me now, or wait until I land in Paris."
"No," Brady said. "I have an appointment to meet him tomorrow afternoon, so I better brush up on things now. So, how does his arrangement with Reese work?"
"They have a guest apartment next to their house," Alan explained evenly. "Ryan meets the guys there. I guess Reese knows about it and doesn't care. I'm not sure about their exact arrangement."
"I see." Brady looked over his notes for any other questions. "One last one. What do these 'plus' signs mean in your notes? I see them next to several players' names, on the days when they visited Ryan."
"Oh, that means they brought friends along," Alan said. "Sometimes Ryan likes entertaining several guys at once."
That did it. Brady almost creamed his pants right there. He had a few other questions for Alan, but those questions would have to wait.
The following afternoon, Brady arrived on the location where Ryan was filming scenes for his latest movie, "Cruel Intentions". The set was a large empty house, a true Hollywood classic, and when he arrived he was directed to a service wing over the garage that had been set up as a temporary office and actor's trailer.
"Ryan's filming for the next half-hour or so," a handsome young office attendant informed him. "After that he'll get out of make-up and meet you here. You can wait around if you like."
The room was a small bedroom at the top of a skinny back stairs. It had a secondary entrance from the outside, leading to an outdoor stairway that connected it to the driveway. Brady supposed this was designed as the chauffeur's quarters when the house was new, several decades ago. The room was sparsely furnished with a makeshift dressing table, a couple of large trucks, and a modern platform double bed. In one corner was a small desk and filing cabinet, which he recognized as the portable office Alan usually set up for his larger accounts.
Standing in front of the dressing mirror, Brady took a moment to check himself out. A former college rugby player in the Midwest, he still had a great body for being 27 years old, and his short dark buzz-cut and steel-blue eyes gave him (he was told) a real movie-star appearance. In fact, it had been his last boyfriend in Ohio who had originally suggested Brady travel out to Hollywood to look for work. And now, here he was, in Ryan Phillippe's trailer, looking at himself in the star's own mirror. His pressed shirt and khakis hung well on him, flattering his package and his overall physique.
Brady approached the desk and examined some of the papers sitting on top. Most were bills and other paperwork for recent trips Ryan had made to promote his recent movies, "54" and "Playing By Heart". In the desk drawers, he found only a few office supplies, and in the filing cabinet, most of the file folders had boring names like RECEIPTS-NEW YORK and PLANE TX-1997. However, toward the back of one drawer was a box labeled: "Backstage Photo Shoot at '54."
Curious, Brady started taking out the box, but then hesitated. Then, he figured: Well, this whole cabinet is the property of Coswell & Sons, so why shouldn't I take a look? He carried the box to the bed and lifted the lid off. And as active as his imagination had been in recent weeks, he wasn't quite prepared for what he found inside.
It was a pile of polaroids, maybe five dozen total, that were obviously taken on the set of "54", supposedly inside the famed New York night club of the same name. Brady was aware that they had extensively re-built the club for the movie on a soundstage in Studio City. Although the lighting was dim and the Polaroid was a crappy exposure, it was unmistakable what he was looking at: Pictures of men, all of them naked and beautiful, having sex or in other suggestive positions.
The first few he looked at were simply full-body shots of men in different stages of undress. Brady vaguely recognized them, and figured they were probably extras or crew. But in the fourth picture, he beheld an amazing and thoroughly tantalizing sight: A slender boy bent over a table, his beautiful ass up in the air, his blond head turned to one side as a line of nude men seemed to be forming behind him. The men were undoubtedly preparing to fuck him, and the blond in question was undoubtedly Ryan himself.
Brady stared at the photo, stunned. He then flipped to the next one, and the next after that, until finally he simply emptied the box of polaroids all over the bed. In ever single photograph, Ryan was being fucked. He got it on his back on the table, bent over the table, on all fours on a couch, sitting down on a guy's lap, and in every other position he could think of. Whoever took the photos was focused on Ryan, capturing the blond stud's blissful expression, his face contorted in ecstasy as the men banged him over and over. In many of the shots you could see the hard bodies of the other men as well, grabbing his slim hips as they thrust into him or jacking-off their big hard-ons as they waited their turns in line.
There was no way Brady could continue looking at these photos and not release the raging boner they gave him. So, without thinking that anyone could walk in, he opened his khakis and pulled out his nine inches of meat, stroking it slowly as he spread out the polaroids on the bed.
His favorite one, he decided, had Ryan with his sculpted legs pointing up and out at an angle, as a tall, well-built black dude drilled into his bottomless ass. From other photos, Brady knew that the black guy had an incredible cock, and in this one it was buried all the way inside Ryan up to the hilt. Standing nearby, smiling as he gazed on the scene, was a goodlooking white guy, whom Brady suddenly recognized as Breckin Meyer! How was this possible? He knew the boys had acted together in the movie, but had no idea that Breckin would indulge in these sorts of acts of passion. Of course, until a few weeks ago, he wouldn't have guessed (though he did often dream) that Ryan was the type to participate himself...
"Ah, you found my stash," came a voice suddenly from the doorway.
Brady about shit. He jumped up from the bed, his back to the door, and was in the process of re-buttoning his slacks before he even registered who the unexpected visitor might be. Bashfully, with nowhere else to turn, he began a slow pivot toward the bedroom door.
Ryan was there, smiling exuberantly. He was dressed in old blue jeans and a simple white T-shirt. "Don't worry about it, man. You're Brady, right? From Coswell?" Brady nodded. "Jeez, you're cute!"
Brady didn't know how to respond to the compliment, and he was a bit star-struck anyway, so he decided to ignore it for now. "Ryan...Mr. Phillippe, I'm so sorry...I was going through the files..."
"Hey, like I said, don't sweat it, man," Ryan told him, entering the room and setting down a leather knapsack next to the dressing table. "It's just what I'm into. The sooner you found out, the better."
Still flustered, Brady began assembling the photographs to put them back in the box where he found them.
"Nah, don't bother with that," Ryan said. "Sean and Eric are on their way up here with Josh, and I don't think I've shown them those photos yet, anyway. Come on over here and sit down."
Brady sat down in a chair next to the star, regaining his composure as his new client wiped the last vestiges of make-up away from his beautiful face.
"Well, really...I'd rather our introduction wasn't so awkward...but anyway, I'm Brady Jones. I'll be taking over your account from Alan." He extended his hand for Ryan to shake.
"Great!" Ryan shook his hand, and held it for an extra moment, looking up Brady's well-muscled arm, at his solid chest, and into his beautiful eyes. "Alan was a nice guy, and it was great of him to take those pictures for me...but really, I have a feeling you and I are going to get along better in the long run."
The words and the touch sent a shiver up Brady's spine. He couldn't believe his luck!
"I hope so," Brady intoned, as suggestively as he dared.
Then, to Brady's delighted surprise, Ryan lifted off his T-shirt, exposing his gorgeous chest. "Listen, a few of the guys are headed up here, and we're going to have fun before I have to head home for dinner with Reese. So our conversation might get cut short a bit once they get here. Do we have anything specific to talk about?"
Fixated on Ryan's cute, understated pec muscles, Brady said: "Uh, no. I don't think so." He looked back up at Ryan. "So...fun? You mean...?"
"Yeah." Ryan unbuttoned the fly of his Levi's and began pulling them off his sexy legs. "Look, I hope this doesn't shock you, and I know Alan filled you in somewhat, but I like guys, and I need to get fucked. You can probably guess this much from those pictures. Anyway, I get it as often as I can. When I'm not working, and I'm not hanging out with Reese, this is what I'm doing. I guess you'd say it's pretty much my number one hobby. I'm a total slut for cock!"
Brady gulped back any words he might have been tempted to utter, choosing instead to behold this perfect hunk getting naked in front of him and baring his sexual soul. Finally, he said: "You get...fucked?"
"Fuckin' right!" Ryan beamed. "You want some?" He got on the bed, among the polaroids, and spread his legs suggestively. He was still wearing a pair of white briefs, but a moment later he reached into those to pull out an impressive thick, uncut hard cock. He gave it a few jerks while waiting for Brady's response.
"You mean...?"
"Sure, what the fuck. You're very hot, you know. And I guess you liked what you saw in these pictures." Ryan reached over to a cardboard box next to the bed, where a nightstand would traditionally be, and pulled out a tube of lube. He squeezed some onto his fingers, then replaced the tube and lifted his legs so that he could work the lube into his ass with his fingers.
"Alan even fucked me once or twice. Good ol' straight Alan. He's pretty hot, you know. Nice dick. And during the '54' press tour I used to give him blowjobs just about every night we were on the road."
Brady couldn't stand it any more. His dick led the way to the bed where Ryan lay waiting. In an instant his slacks and shirt were off, and he was nestling comfortably between the star's legs. As he leaned forward over Ryan, their dicks and chests touched. With one last look of disbelief, he brought his lips to Ryan's and the two shared a long, erotic kiss. Brady thought he was in heaven.
"Man, you're good," Ryan told him, more softly now. The star clutched Brady's strong shoulder muscles and ran a fingertip down his firm back. "You've got a great build, my man. And one mean-looking cock!"
They both looked down. Brady's nine inches were throbbing with desire and spitting precum onto Ryan's sexy belly. Brady looked back up at his passive prey and grinned. "Yeah? You want that?"
"Yesss..." Ryan hissed. "I want it right now!"
And before Brady even realized what was happening, Ryan had swung his legs up and around both sides of Brady's body, locking his heels over the larger stud's shoulders. Ryan then reached down and with both hands, worked the tip of Brady's hard-on into his puckered, hungry ass.
"Ohh...yeah..." Ryan moaned slightly at the pain of the intrusion, but it obviously was something he knew he could handle. With a quick inhale, Brady pushed a little bit more of his cock inside, and then suddenly Ryan's ass seemed to suck it in all on its own. Amazing!
"OH! Man...yeah..." the blond bottom cooed. "Jesus-fuckin'-christ, that is so good... Fuck me, stud. Fuck me good and hard!"
Not waiting to be asked twice, Brady withdrew his entire dickstem and then sunk it into the star's hole once more, then followed with another stroke and another, plunging in and out of the superstar's ass.
"Harder, man," Ryan commanded urgently. "Don't worry, I can take it. I like it pretty rough."
So, Brady repositioned himself, getting up onto his haunches for better leverage. This gave him the added advantage of looking down at Ryan's impossibly cute face and sexy body as he fucked him. With a deep breath, he pushed all the way back into him and then began throttling him in a quick rhythm, banging into his beautiful ass as hard as he could. As Brady fucked him, Ryan started bouncing on the bed, in and out of the mattress, slightly at first and then building and building to a more vigorous pace. Ryan's face took on an expression that made it look like he was crying, but from the pleasurable moans he was emitting Brady understood they were tears of joy.
It was, Brady realized, the best fuck he had ever had. Unlike most bottoms he was with in this position, Ryan wasn't even touching his own cock, and seemed to desire letting the fuck last as long as possible. Brady decided to give him the full treatment, and hold off cumming as long as he could. He banged the hot boy as hard as possible while still keeping himself from the brink of orgasm, stopping momentarily now and again but then seconds later drilling right back in for more.
Over twenty minutes or so, the effect of this game was to take Ryan from a state of pleasure to a state of unparalleled sexual gratification. As the time rolled by, as the strokes into his asshole grew even more relentless and powerful, he mentally detached himself so that he seemed to be hovering up in the room, riding a tide of total ecstasy. He loved nothing in the world more than being ridden hard by a handsome stud with a big cock, and Brady was definitely delivering the goods. He felt consumed by Brady's dick.
Finally, when it seemed impossible to find any additional energy for warding off the inevitable, Brady allowed himself to start bringing on an orgasm. And what a climax it was. The 27-year-old felt it in his back, in his loins, his legs...every part of his body. All of his many muscles were focused on the job at hand, which was to fuck like a piston in and out of this blond hunk's hole. When the orgasm descended, his whole form locked up for a half-second, until the first spray of seed was released deep inside Ryan's asshole. Following that, Brady's energy seemed to double itself, and he madly exerted himself to thrust as much cum as deep inside the boy as possible. He grunted and screamed, and before it was done was had emptied more than a dozen spurts of semen into Ryan's famous, perfect little ass.
When there was clearly no more to give, he collapsed forward onto the boy, half-conscious and recklessly kissing every sweet-smelling area his lips could find around Ryan's face, ears, shoulders and neck.
A minute later, he was suddenly aware of other people in the room--voices and sounds, people speaking excitedly and getting undressed. He rolled off of Ryan and squinted, looking out into the room. Three young men had joined them, and were pulling off their clothes, presumably to join the action on the bed. "Uh...who's this?" Brady mumbled.
"You know these guys," Ryan told him. "Josh Jackson, Sean Thomas, and Eric Mabius. They're all working with me on this movie." Brady indeed recognized the young stars, who were now nearly naked and seemed to be smiling approvingly at his body and deflated cock.
"Anyway, you'll need to move over and make room for them," Ryan continued. "C'mon Josh, you're next!"
To be continued...
What do you think? Feedback and suggestions? backlash29@hotmail.com
My other stories are "Buttsex Junkie" in Bisexual/Beginnings and "Cup of Joe" in Gay/Authoritarian.