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
backlash29@hotmail.com
Chapter 6: Around Hollywood
Working with Ryan is like working with a full-time professional cum-hole. And of course, I mean that in the best possible way. He takes loads up his ass left and right, as readily and as often as any goodlooking guy with a nice cock is ready to give them. Knowing this gives me a raging hard-on whenever I'm with him, and most days, he even helps me do something about it. To be precise, he gets naked and takes my rock-hard dick into his wet, soft, tight, warm cum-hungry hole. Hell, he gives me a hard-on even when I'm not around him! At dinner, at the gym, at home in my bed at night, I often picture him getting fucked, and it always occurs to me that, at that moment, that's probably exactly what is happening. I think about his coy smile and his luscious butt, and immediately--even subconsciously--I imagine my hard cock sliding all the way into it. I also picture his response, which is always more or less the same: a quick, sharp intake of breath, followed by a grateful moan and a long exhale, a perfect, satisfied sigh.
It is now summer of 2000. Ryan and I have worked together for nearly one year. I scored big points setting him up to be gang-fucked by those ballplayers in Toronto (see Chapter 4). By way of thanks, he not only let me fuck him silly after I arrived at the Toronto location, he also invited a few of the Toronto Blue Jays to stop by and join us, including Shawn Green, who by his account had been one of the hottest fucks of his life. (Shawn, it turns out, had come by Ryan's hotel every night since their initial meeting.) After Shawn and I had nailed Ryan full of two loads each, we let the other ball players take over servicing his hole, and while I laid back next to Ryan on the hotel bed, Shawn fucked my ass good and deep--just the way I like it.
Ryan also became more forthcoming with me about the other celebrities who used his hole, and with the consent of a few of them, began letting me join in occasionally when they stopped by. In this way, I came to observe the very private details, including dick size and sexual habits, of various famous Hollywood types. The examples are too numerous to mention them all, but a few of Ryan's regular fucks stand out in my memory: Cameron Mathison, who met Ryan following his soap opera days when he joined the cast of "54", was a voracious and very sexy fuck, who also stuck around to fuck and get fucked by me on one occasion; Jason Priestly, who possesses a cock so big it has taken on its own legend in Hollywood circles, both gay and straight; his "90210" co-star, Brian Austin Green, who typically preferred bottoming, especially for Jason's monster cock, but cheerfully made an exception when it came to plundering Ryan's hole; Patrick Muldoon and Caspar Van Dien, who were shooting "Starship Troopers" nearby and loved nothing more than unloading their cum into Ryan at the end of a long day; and, of course, that consummate cock-hound Scott Wolf, who had been fucking Ryan regularly (it turns out) ever since "White Squall".
Then, there were the musicians. Ryan watches MTV almost constantly, and because my agency has many connections into the music industry, he frequently asks me to try and introduce him to studs who are new and hot and young. Especially young--Ryan loved the boy-bands. He was getting fucked by Justin Timberlake months before Brittney Spears and he started dating. Even now, whenever Ryan sees an NSynch video, he complains about not getting Justin's long, fat log-like dick as often as he used to, and how he was a much better pussy than Brittney could ever hope to be.
But the best of all was scheduling the "housewarming" party at Ryan's remodeled studio apartment, attached to his and Reese's house up in the Hollywood Hills. I was having a conversation one afternoon with Ethan Hawke, at a fairly secluded outdoor table of a restaurant on Wilshire Boulevard. Like Ryan, he was a young married stud who enjoyed frequent dalliances with other men, with the tacit approval of a busy, loving superstar wife. A total top, he was a good match for Ryan's voracious sexual appetite: the two of them met once or twice per month, depending on their schedules, and Ryan would get filled by Ethan's over-large uncut cock. I set up these encounters, but had never witnessed one previously.
"I was up at Ryan's and Reese's a few weeks ago, for a dinner party," he told me. "There were a couple of contractors working on the studio. The younger one looked pretty hot."
"Yeah," I chuckled. "Ryan hand-picked that one. He's a frequent guest after-hours as well. Both he and his boss know their way to Ryan's apartment after a long day on the job." At this point, Ryan hadn't yet moved everything out of his old apartment; he and Reese lived together at the house, but he kept the old place for his sexual rendez-vous.
"No shit," Ethan said, picking thoughtfully at his pasta salad. "Well, maybe this contractor boy and I should join forces sometime. You know, I could get some other guys involved too, and all of us together could show Ryan's hot little ass a hell of a party..."
"I'm pretty sure he'd like that," I said, looking in Ethan's beautiful eyes. I assumed that by bringing it up with me, he meant that I myself could get a piece of this action.
And so the housewarming idea was born. At first, we were going to just surprise Ryan on the day it was done, throw a few temporary mattresses on the floor, and do our thing. However, a few days later, Ethan called me back with the idea about the sling.
"He has a lot of toys; I know, because I've seen them," Ethan said. "But he also told me he's never done it in a sling. I go to the sex clubs sometimes when I'm out-of-town, and let me tell you, fucking a dude in a sling is some of the best sex there is. So, I wonder if he's ever considered putting one into his new place?"
I told Ethan I'd check with Terry, the young stud contractor. Terry, it turned out, was no stranger to sex clubs and slings himself, and got instantly excited by the idea of installing one in Ryan's new space. We also discussed finishing the far wall next to the sling as an open storage system for Ryan's collection of dildos, vibes, lubes, beads, and other toys and supplies.
Then Ethan mentioned who else he was planning on inviting. I couldn't believe how hot this guest list was. It seems all the "straight" male stars around L.A. who play with other male celebs are in some kind of secret circle. Go figure. Anyway, I guess Ethan trusted me, because he made it known that the three finest slingmasters he knew personally were none other than Matt Damon, Jude Law, and Mark McGrath (the singer from a band I like, Sugar Ray). Mark, he told me, was a horse-hung top who fucked like a maniac and had a grandiose verbal ability that he exercised while doing so. Matt, similarly, was an aggressive top, but more of the quiet, simmering variety. Jude was the kinkiest of all. He loved every kind of sex--men or women, top or bottom--and was very adventurous when it came to trying out new things. In particular, he had played frequently with domination, and with his long, sinewy arms and icy stare, was developing a reputation among their secret elite for being a safe, sexy and effective fisting top.
The day we all met at Ryan's, our combined erotic energy was through the roof. I had stopped by earlier to hang out with the guys, but Terry was having some-last minute problems with the ceiling support for the sling, so they needed someone to delay Ryan for another hour. No problem--I met him at our favorite sleazy motel on Sunset and gave him a good, hard high-energy pre-surprise-party fuck. When we finally arrived on the scene, he was truly shocked and turned-on by what we had spent those few weeks preparing...and by what we all knew was coming next.
"Get in, baby," Ethan cooed to Ryan as he walked behind us to shut and lock the studio door.
Ryan looked around at all of us. Jude had finished snapping the long glove onto his right hand and forearm, and regarded our bottom-host with a smoldering, intense stare. Matt, having pulled the shades, leaned back in the shadows against a column next to the sling; his pants were open, and his fat, treacherous dick was in his right hand, where he pulled on it silently, daring our prey to come forward.
Mark was smiling an excited grin. He had his dick out, too; he had been wearing a thin pair of jam shorts, which were now at his ankles as he stroked and caressed his fat log in anticipation of the fuck we would all enjoy. "Go on, babe," he said to Ryan, motioning at the sling. "You're going to love it."
"Fuckin' right you will," Matt spoke up, his gruff "Southie" accent serving him perfectly for such a scenario. "These two" --he gestured at Mark and Jude-- " have been licking my big cock and tight ass for the last half-hour waiting for you to get here...so get in that fuckin' sling and let's get started!"
Ryan obeyed, three parts eager to one part meek. Although Ethan had claimed Ryan had never been in a sling before, I kind of doubted that to be true, especially when I observed the ease with which Ryan got in. I had helped Terry pull Ryan's clothes off as he looked around the room in wonder at his toys, boys, and shiny new fuck-pad. Naked, he shifted his butt in the sling so that his tantalizing hole was right at the front edge of the leather padding, and hoisted his cute legs slowly up to rest them on the heavy vertical chains.
Matt, kicking his pants aside and pulling off his polo shirt, stepped over to the sling and fixed Ryan's ankles into the restraints. "That oughta hold him," he muttered when he was done. "Gentlemen--do your worst. Fuck him, fist him, do whatever--he wants it all in his hole. We know this bitch is going to love it."
Hearing Matt's words, I swooned. This was my first experience ever meeting this hot stud in the flesh. I wanted more than anything else to someday see him and Ben Affleck in action, since through my conversations with Ryan I basically knew the age-old rumor about the two Boston buddies to be true. Today, anyway, I was pleased to at least see Matt, my favorite of the two, naked and hard, in the flesh. I'd probably beat off to his image a hundred times since I first saw "Good Will Hunting", wishing it were my ass and not Ben's (or Ryan's!) taking that fat, blunt missile into my lower depths.
Jude approached Ryan's upturned hole. He was wearing the glove, and had slathered a Crisco-like lubricant onto the whole of it, including the sexy area of his forearm just under the elbow where the glove ended and his impossibly tender tan skin began. Dipping his gloved hand back in the can of lube, he took a huge dollop and dabbed it on Ryan's asshole. The hole was leaking cum by the pint, my own being the freshest load. Jude gently swirled the thick lube around the hole, mixing it with the ejaculate that was pouring forth, until he had effectively stopped the leaking. Then, he started massaging the lubricant slightly deeper in Ryan's ass in circular motions, then deeper still, until he was working all four fingers easily in and out in twisting strokes.
"Okay, cunt," he muttered, his refined accent taking on a sinister tone. "I'm going to put this hand inside your hole now. You want this, right?" It was hardly a question that he needed to ask.
"Oh, fuck yes," Ryan sighed. "Please. Give it to me. I want you inside my ass."
"Yeah?" Jude continued stroking and teasing the hole. As we watched, Ryan's sphincter seemed to gasp longingly under Jude's strong, even command. "You like this? You want a roomful of men having their way with your pretty arse?"
"Yes, please..." Ryan said, breathless with anticipation.
"Tell me."
"I want..." Ryan moaned. "I want...you to fuck me...fist me...do it, please..."
"You want my hand in your hole, bitch?" Jude taunted. "Cunt, is that what you're after?"
"Fuck, yes, PLEASE!" Ryan pleaded. "I need it! Please...I need all of you, deep inside me! NOW!"
There was silence for a moment, and then, in a long gradual movement, Jude reached all the way back with his elbow, so that his fingertips just grazed Ryan's cummy opening; then he paused, but only for a second; and then, with a long twist, sent his hand in up to the wrist. One moment we were viewing Ryan's familiar, gaping pucker, and the next, Jude's hand was totally inside him, up to the wrist. A generous backload of Crisco and cum oozed out around Jude's hand simultaneous with the action, and Ryan let out a scream of desire.
"FU-U-UCKK! Oh... OH, man! Fuck...oh, Jude, fuck me, do me, that feels so GOOD...."
Jude kept the hand inserted for a moment, then slowly began twisting it around some more. With every tiny movement he made, Ryan's whole body trembled with erotic response. Soon, I noticed, he was well past the wristline, and was making his way to the elbow. His position in front of the sling was ideal, allowing him to insert his beautiful arm straight down at an angle, the most natural way gravity could pull it. Each time he pushed in another half-inch, he stopped, twisted his way out backward a bit, and then twisted it back in again, making Ryan moan happily at the new intrusion, way down inside him, deeper still.
I had only witnessed a fisting once before, a few years earlier. I was at one of the sleazier L.A. sex clubs, just after I moved from Ohio, and a very cute chicken-boy (probably around 18 years old) was kneeling dutifully over a bench as a handsome leather-daddy rammed his entire thick forearm in and out of the high-schooler's ass. From the confidence the top was exuding and the pleasure with which the young stud was taking it, I could tell they were both very skilled and practiced at this maneuver. It was hot as hell to watch. Later that night, when the leather-daddy was fucking me in a side room, he gruffly asked if I wanted his fist in me after his dick. I gulped and said no, I'd never done that before. But I thought about it frequently ever since.
Similarly, the way Jude and Ryan were going at it, I could tell they were no strangers to this experience, either. I vaguely recalled Ryan telling me that one or two of the players I hooked him up with were fisting tops, and that he sometimes took their hands and forearms up his hole as a prelude or postlude to high-energy fucking. From the look on his face in the current situation, it was a violation he fully enjoyed. And Jude was amazing, also. Here was this fantastic-looking Hollywood star, a few feet in front of me, anally penetrating my celebrity client in the most extreme way possible, with experience and intensity and zeal, pushing his arm in to make Ryan cry out, then pulling back slightly, releasing lube and cum around the sides of the opening, before ravishing the hole again. He reminded me of a plumber, a very sexy plumber, working diligently on a stubborn drain.
This went on for some time, and all of us were spellbound while watching. Matt's eyes were glazed over with lust. Mark was slack-jawed, the cutest smile on his lips as he eagerly jerked off his fat dick. Ethan moaned and grunted while flogging his uncut meat as well. Terry and I did the same. Eventually, Jude pulled out of the hole completely and backed away from the sling, removing his glove. I looked back at Ryan's ass, and his sphincter was more dilated than I'd ever seen it, a gaping cooze, flooded with lube and cum, hungry for further violation, free of one stud to fill him and aching for the next.
For the rest of that afternoon, I mostly enjoyed the role of voyeur. Although it was hot as hell to be in the company of these sexy celebrity studs, I wasn't sure what the boundaries were for engaging with them in any kind of contact or hot play. Besides, it was Ryan's party. Just watching his ass take on the oversized dicks belonging to these sexy fantasy studs was going to be some of the best sex I'd ever had.
First up to fuck Ryan was Mark. It was clear he was chomping at the bit to sink his cock and his load into Ryan's hole. "Oh fuck..." he moaned as his throbbing cock finally made its way inside. The sling was at a perfect height for all of us to simply stand and lean forward into the fuck, as Mark did now. His strong, sexy legs arced and flexed slightly as he commenced his vigorous in-and-out strokes.
"Ooohhh... Ohhh..." Ryan moaned lovingly as Mark stuck him deep. "Oh god Mark, yess... fuck me, man... oh shit, your dick feels so good up my ass..."
"Yeah!" Mark whooped, and stepped up the pace. "Shit, this fuckin' whore really needed some dick!"
I smiled. Ryan had told me at the motel he'd already been fucked several times that day around town, and had twenty fresh hot loads stewing up inside his ass, supplied by more than a dozen studs. If you counted the evening before, the number of cocks and loads was nearly twice that number. In twenty-four hours, Ryan got thirty-some loads inside him, courtesy of two dozen willing studs. Talk about a charmed life!
The others all knew this, of course, and that was why they felt free to use Ryan as they saw fit. We all knew he was a cock-crazed slut who always wants more and more men to use his ass. I could hardly wait for the chance to dive between his legs, as I often did, and suck out the remains of all these hot studs from his aching hole. There would be one hell of a meal for me in there after these boys were done!
I had my pants and shirt off by now, and was pulling on my engorged dick as I focused on the gorgeous dimples in Mark's ass as he threw a mean, hard fuck into Ryan's pussy. "Yeah, do it, Mark," I urged him. "Plow his cunt. He loves getting fucked hard. The harder to better. Use him!"
"Fuck, yeah," Jude chimed in. "He's just a fuckin' cum-dump. He wants all our loads in his hole."
Matt looked my way. Our eyes met, and to my thrill and surprise, he walked over to me a moment later. He stood next to me, took my hand, and put it on his dick. As I wrapped my fist around his enormity, he reached over and did the same to me. We continued, beating each other's hard cocks as we returned to watching the scene in the sling. Terry, the contractor, was on his knees, sucking Ethan's superstar dick.
Soon, Mark couldn't hold out any longer. "Yee-eee-aaa-aarg-gghh!!" he yelled, and slowed himself to about ten hard, cathartic thrusts, each one spraying a huge load of seed inside Ryan's asshole.
When Mark pulled out and stepped away, Jude was quick to take his place. Ryan's cumhole, on full display between his splayed thighs, was truly a sight to behold: A gaping hole, oozing and leaking with Mark's jizz and god knows who else's, expanding and contracting, seemingly breathing with a life of its own. It had contracted some since Jude's fisting, conforming to the thickness of Mark's cock as he thrusted in and out, but still looked open and alive and ready for the next violation.
While Ryan and Mark had been fucking, Jude had set up a portable table next to the sling, almost like a TV tray but taller. On it, he placed a couple of big, intimidating dildos and the open can of Crisco-like lube.
"Let's see how this cunt likes a few toys in his asshole," Jude said. Ryan moaned loudly in response.
As Ryan stared intently at Jude, his mouth fixed in a slack-jawed expression of anticipation and sheer bliss, Jude worked the first toy into his hole: a fat, black 11-inch dildo with a handle at one end. Of course, Ryan sucked up the whole thing without much problem; he gulped and whimpered briefly, then continued looking to Jude, curious about what came next. Jude gripped the handle, pulled the toy mostly out of Ryan's asshole, and then slowly pushed it in again. This time, the force of Jude's thrust gave Ryan extra stimulation and pleasure, and he shut his eyes for a moment, savoring the sensation of being violated by the enormous toy. A moment later, Jude settled into a fast rhythm with the dildo, plunging it in and out of the hole at a rapid, crazy pace, until Ryan's groans mounted a crescendo and became shrill screams of joy. Jude leaned into the sling for better leverage and showed no mercy as he throttled the fat substitute cock in and out.
"Shit, man," Ethan moaned, enjoying his blowjob from Terry in the corner next to Matt and me. "Work that big thing into him, man. His hole is bottomless. Just fuckin' rape it with that big toy. He loves that shit!"
After a few minutes of this, Ryan was almost hysterical with happiness. Jude stopped suddenly, and Ryan's ass ejected the black monster. Next, Jude reached for an even larger toy--fatter and longer, about 13" by 6" wide--which I also now noticed had a dial attached to its base. It was the biggest vibrator I'd ever seen! Was this from Ryan's collection or had Jude brought it along today as a special treat?
Just like the first toy, Jude worked it in carefully at first, then once he knew Ryan had it, proceeded to thrust repeatedly, almost violently, in and out of the hot slut's hole. Ryan reacted with the same jubilation as before, writhing about in the sling, his legs pulling on the restraints that solidly held his ankles, spread apart and aloft. He screamed with joy at Jude's masterful application of dominance over his hungry hole.
"Fuckin' A," Matt whispered to me, with a look of wonder, as he clutched my cock even tighter, and I felt his lurch and spit precum in my grasp. "What a fuckin' whore."
"Yeah," I whispered back. "He gets so many fuckin' cocks in there, and he still wants more."
Ryan was wildly playing with his cock as this beautiful torture was performed on his hole. Because his ass is nearly always his "business end", I often forgot how hot and turgid his dick is, and he looked sexy as hell playing with it now. With all of the exquisite pleasure he was receiving, he beat it wildly and seemed to be on the edge of shooting. "Shit guys, I think I'm gonna cum..."
"No bitch! Wait..." Jude cried sharply. Keeping the toy inside with one hand, he grabbed both of Ryan's wrists with the other and prevented him from going further. "You don't fuckin' cum unless we say so."
Jude stopped plunging the toy into Ryan, and instead just left it inside. He produced a simple elastic belt that attached to the base of the artificial cock, and wrapped it around both of Ryan's hot, slender thighs, securing the toy in place. Then he began twisting the dial, and we all heard a humming sound. By the time it was at its highest setting, Ryan was delirious, and Jude had to grab his arms and put them in the front restraints to keep him from touching himself again.
"You don't cum unless we say so," Jude repeated. "And right now, I know just how I want you to do it."
His next move surprised me. There was Ryan, all four limbs tied above him, helpless, with a raging hard-on ready to explode and a 13-inch vibrator filling his lower intestine and making his whole body shake. What does Jude do? He takes Terry's workbench, a low table that was sitting nearby, and slides it under the sling. It fits perfectly, with about twelve inches of "bounce room" to spare. Then, Jude climbs onto the table and straddles Ryan's cock, reaching behind himself to aim it into position. Was he...?
"I've wanted this cock in me for quite a while, pussy-boy," he sneered. "You're such a fuckin' whore that you always just want more and more hard cock in your hot cunt. But some of us have those needs, too."
"Holy shit..." Ethan exclaimed from behind us, moving closer to the scene to see what was about to happen.
Matt and I quit jerking each other for a moment, and just clutched each other's pricks, in awe of the sudden change of position. "Shit," Matt muttered. "I guess Jude here wants a little ass action of his own..."
Jude's sculpted, sexy legs braced him as he hunched into position, and a moment later, his cute, hard ass has sunk down completely onto Ryan's throbbing cock. "Ooohh...yess..." he cooed. "That's it, that's the cock I wanted. Fuck my ass, Ryan. Fuck your top-daddy, good and hard. I want to feel your load go in my hole!"
In his position, Ryan could hardly thrust, what with his arms and legs in restraints and a giant vibrator stuck deep inside his entire body. So, Jude helped things along by riding Ryan's cock as the toy continued to fuck him. He soon found a hearty rhythm, grabbing the front chains of the sling and using his sinewy legs to support himself as he rode away on Ryan's pole.
"Yeah! That's it! Fuck your daddy!" Jude shouted. "Fuck, Ryan, that feels so fuckin' fine! Ride my hole!"
Matt and I, newly recharged by this latest development, returned to beating off each other's meat. Terry was still sucking Ethan's cock, and Ethan kept inching closer to the sling, to the point where both young men were partially blocking our view. So, Matt told Terry to stand up, grabbed him, and then forced him back down to his knees in front of us. Ethan stood next to us and beat off, as Terry took Matt's dick and mine in each hand and started alternately deep-throating us as we continued taking in the scene.
Meanwhile, Ryan himself was struggling like I'd never seen him before. Moments before, he had been on the verge of cumming just from jerking himself off in the sling. Now, instead of his own hand, he had Jude Law's sexy ass-tunnel stretched over his fat prick, working its way up and down. It took only a few more minutes of this before Ryan noisily shot his bottom-cream into Jude's hole.
"OOOOHHH! Oooohh, fuck...yes...oh, man...a-a-a-a-AAAR-RGGH!!" Ryan shouted as he came.
"Yeah, that's it," said Jude in a near-whimper. "Oh, I've wanted this cum in me for so long."
I was in danger of cumming myself, and so was Matt, so we pushed Terry over to Mark, who had reclined on the bed and was working his prick back to a state of readiness. As Terry took Mark in his mouth, Ethan, Matt and I approached the sling. Matt slowly turned down the dial on the vibrator until it was off. Ethan undid the elastic fasteners and removed the toy from Ryan's hole. The gaping cunt was even more wide-open now, like a woman's pussy, frothing with jism but alive and ready for more.
"Shit," Ethan chuckled. "Sure enough, the whore wants more."
"Of course he does," Matt said. "He always wants more. We can fuck him here all night and he won't be satisfied. I want to sink a few loads into him myself, then sit back and watch the rest of you do the same."
I stroked my cock gingerly, in anticipation. "Works for me."
Matt's hard cock was like a baseball bat, and it throbbed and jumped in front of him like it had a mind of its own. It kept leaking pre-cum, in obvious anticipation of being buried inside Ryan's ass. Matt lined up his cock with the hole and immediately thrust in, making Ryan yelp with pleasure at the re-entry.
Jude, meanwhile, did not dismount Ryan's spent cock. In fact, he continued riding it a little, and I could see from where it entered his ass that it never totally lost its hardness. How hot was this? He was going to continue riding Ryan while the rest of us took our turns on Ryan's ass! I was so accustomed to the idea of Ryan being a power-bottom that the idea of him fucking anyone had never really occurred to me. And now Jude Law, possessing one of the sexiest asses in show business (and one of the sexiest bodies and smiles as well) was using his ass to give Ryan pleasure, and seemed to enjoy it plenty himself as well.
Matt rode Ryan's ass good and hard, cumming twice in quick succession. I guess my hand-job and Terry's blow-job, together with all of the visual stimulation we'd been enjoying, was too much for Matt to handle. I relished the view, however brief it was, of hunky Matt Damon gripping Ryan's slender thighs and ramming his thick cock in and out of that bottomless hole. Like Mark before him, Matt had a fantastic, muscular jock ass that dimpled beautifully and deeply with every thrust he made into Ryan's rectum. Someday, I vowed, I must have this sexy stud on top of me, pounding away in my asshole the same way he's doing to Ryan now.
Ethan was a little too turned on by all of this also, and he came all over himself around the time Matt was shooting his second load into Ryan's hole. Terry was still very involved with the expert head he was giving matinee pop idol Mark. Jude was still riding Ryan's cock like the randy British cum-hound we now all knew him to be. So, that left me. I stepped up, sinking my cock into Ryan's sloppy ass. It was pure heaven. For all of the times I had fucked Ryan (it had to be over a hundred times by now, up to and including our motel encounter earlier that afternoon) I don't recall feeling his boy-pussy quite so stretched-out and filled to the brim with man-juices. Nor had I had the exquisite pleasure of fucking Ryan while his own prick was being gloriously ridden by another gorgeous stud.
As I railed in and out of Ryan's hungry hole, Jude bounced on Ryan's cock a few inches before me. At one point, I got an idea. I slowed down my fucking for a moment, got Jude's attention, and asked him to spin around. A moment later, Jude had done a 180 on Ryan's cock, and he continued riding but was now facing my direction. I leaned forward and got the tip of Jude's juicy prick in my mouth, making him moan and shoot in my mouth a moment later, the action of his bouncing on Ryan's cock causing him to fuck my face on each up-stroke. This set off a chain reaction: I lost control into Ryan's asshole, adding my load to the huge pile already stored there, ecstatic at the taste of Jude's hot lava spewing into my mouth; and, right on cue, Jude yelled: "Yes Ryan! Cum in daddy's hole!" And I looked down to observe a copious load being sprayed up into Jude's hot ass, and oozing back out of it, down Ryan's cock.
After me, Terry took a turn, banging Ryan good and hard as well all cheered him on. He was getting probably the best fuck of his young life, and he deserved it in my opinion for helping us set this up. When he came, Ethan took over, pounding Ryan's juicy man-cunt for all he was worth. Meanwhile, through all of this, Jude continued riding Ryan like a stallion. When Ethan came, Jude finally dismounted and fucked Ryan himself, starting the whole chain over again: Mark, then Matt, then me, then Terry, then Ethan.
By sundown, we were all spent exhausted and had to get home. Ryan, still in the sling, thanked us for his housewarming present, saying that it was the best way of "christening" the new space that he could possibly think of. The others left, and true to my nature, I knelt dutifully before Ryan's splayed legs and ate my dinner, lapping and sucking and snorting and slurping all of the amazing loads these hot fuckers had planted there. Twenty minutes later, I finally helped Ryan out of the sling and left, my face coated with slime and jizz, and feeling intoxicated by the taste and fullness of eating up the left-overs of truly hot sex.
In addition to the studio apartment, which incidentally became nicknamed "The Playpen" or just "Ryan's Place," a lot of sex also occurred in his trailer at the job site, wherever he was shooting. Like most successful stars, Ryan owned a luxurious trailer, fully tricked out with the amenities pampered actors come to expect: a full kitchen and bar, a shower, a high-tech TV/DVD/stereo tower, and at the back, a huge king-sized bed. Actually, it was a custom mattress that was even wider and slightly longer than most king-sized units; it stretched over eight feet from one side of the trailer to the other, and the foot of it came directly up to the folding door that secluded it from the rest of the interior.
In late 2000, he did a movie called "Antitrust". Some of the scenes were shot in the Seattle area, its supposed location. However, after a few recognizable shots were done for the sake of local flavor, the crew quickly packed up and returned to a soundstage in Los Angeles. Ryan was the start and was required to be on-site nearly full-time every day, even though many of the technical scenes didn't feature him for more than a few minutes here or there. So, for the remaining weeks of the shoot, apart from regular hot sessions in his new playpen, his trailer became his second home.
Nearby, a film was shooting called "Dude, Where's My Car?" The project caught my eye because of the ludicrous title, and the fact that it starred two hot young gentlemen who until that time had not enjoyed leading-role status in any film: Ashton Kucher, the dreamboat from TV's "That 70's Show", and Seann William Scott, a sexy stud who I had first noticed in "American Pie." When I told Ryan about the film and who it starred, he seemed intrigued, and his eyes lit up with a familiar look of lust. Sure enough, a few days later, I got a call from Seann.
"Um, yeah...calling about maybe, uh, getting some time with Ryan?" The boy was cocky, but unsure how to make his desire known. "I mean, everyone knows what he gets into, and when I talked with him the other day he told me you were the one who sets this stuff up..."
I laughed. Most stars didn't call me directly; they had their agents or other assistants do the dirty work, like I did. "Sure thing, stud," I said. "These days, he's in his trailer relaxing for most of the later morning and early afternoon, until 3pm or so. Since you're in the neighborhood, I'd say just stop by."
"Cool, dude. Later," he said. I didn't know if he was just in character, or if this was the real deal.
The next day, I had to admit I was intrigued by seeing Ryan with Seann William Scott, so I hung out at his trailer a bit more than usual. I spread out some of my papers on the table at the front of the trailer, and made a few cell phone calls. Around 10 in the morning, Ryan walked in while I was in the middle of a call. As I arranged details of an upcoming trip, I watched Ryan strip naked, then step into the tiny washroom for a douche. This was his usual routine around this time of day. When he re-emerged, he walked naked to the door of the trailer and opened it. Immediately, a sexy young extra wearing a cap and shorts stepped inside and followed Ryan back to the bed. Minutes later, the extra was crouched on the bed facing away from me, and Ryan's legs were visible over his strong back. He poked deep into Ryan's love tunnel, and Ryan's moans soon mounted to a familiar crescendo, so I rang off my phone call and sat back to watch.
The extra was a cute blond guy, probably about 25, and when he stood up after cumming in Ryan's trench I could tell he had a dick of death. Shit, I'd moan too. He pulled on his shorts just as two more extras, a little older than the first one but even more sexy, entered the trailer, greeted me with smiles, and headed back to take their turns.
I was glad to have this steady supply of dicks for Ryan. We barely ever hired players any more. Between the extras and the film crews, on any film at any location we could generally round up enough hard cock to keep him satisfied. His work schedule was easy enough to work around, especially with the retrofitted trailer set up as a haven for non-stop fucking. Ryan would sometimes drive home to get sling-fucked in his playpen and then return to the shoot, but the truth was it was about a half-hour drive each direction. When he realized he could probably get his ass plowed and take three or four guys during that time, the driving trip was soon cut out. As a result, the playpen got used mostly on evenings and week-ends, or for extended periods when Reese was out of town and Ryan's filming schedule was free for several days.
Around noon, the line of film crew studs had dwindled. Ryan had taken eleven loads in two hours; it was a good day, even for him. Rob, the blond extra, had returned for more and was drilling his fat rod in and out of Ryan's hole. I was at a stopping point for lunch, and when I looked outside, I didn't see any other tops waiting. So I made my way back to the bed where my boss-bitch was getting drilled, stripped, and knelt on the bed next to him.
"Oooohh...ohhh..." he was moaning softly as I approached. I looked down: Close-up and rock-hard, Rob's cock was particularly impressive. With every plunge it took into Ryan's hole, some of the eleven loads of cum squirted out onto the bedclothes. I knelt at Ryan's face, slapping his cute face a few times with my dick until he pivoted his neck and sucked me into his mouth. As usual, his lips and tongue were velvety and wet.
I put one hand on Rob's shoulder, to steady both of us. He was getting very close inside Ryan's love trench. A moment later, he screamed: "YEAH!! FUCK...take my cum, bitch...! Take my fuckin' hot load!!"
He continued thrusted, hard and deep, shoving his huge rod and his big load into Ryan's pussy as far as it would go. When he finally withdrew, breathless and happy, the hot cum gurgled out of Ryan's tight pucker. I reached down and scooped up a little, tasting it for myself and then spreading it on Ryan's handsome cheeks, which puffed and swelled as he continued dutifully sucking my raging hard-on.
Once again, Rob dressed and left, and I was just about to move in front of Ryan's vacated hole and plow into him for a fuck of my own when we suddenly heard a knock on the trailer door. Without waiting for a response, the person knocking opened the trailer door and stepped inside.
To my delight, it was Seann William Scott, and he wasn't alone: Right behind him was his co-star, Ashton Kucher. A total score!
"Du-ude..." Ashton said to Seann as soon as they saw us on the bed. "Fuck man, this is an awesome scene!"
"Fuckin' right," Seann mumbled as they pulled the trailer door shut and slowly made their way back to join us.
"Hi," I greeted them, my dick still in Ryan's mouth. "I'm Brady. I think we spoke on the phone."
"Yeah," Seann responded, still numb with shock. "Right on."
"So..." Ashton said. "This is our little pussy-boy?"
"Yep, this is him," I replied. "He's a real nympho. He'll take your cock as hard and as deep as you can give it to him, for as long a time as you're willing to spend."
"Jesus, what a total whore," Seann whistled.
"Yep," I agreed. "Ryan here loves giving pleasure to men. He's a regular fuckin' cum-slut. He loves getting fucked more than anything else in the world. Like you can see here..." I grabbed Ryan's legs and held them spread-eagle above the bed.. "...he's gotten stretched and lubed already today. So, he's ready for anything you've got to give him."
"Jesus Christ," Ashton said, reaching to finger the cum that was trickling out of Ryan's cooze and forming a lake of jism on the bedspread. "How many loads are in here?"
"About a dozen, right now," I told them. "He'll probably have twice that or more by the end of today."
Seann chuckled. "Sweet, man!" he exclaimed, slapping his friend Ashton on the shoulder. "We got us a live one here, a real live pussy-hole!"
With that, Seann started stripping out his cargo pants and T-shirt, and likewise Ashton removed his slacks and button-down chemise. First up, Seann got down on his haunches and prepared to lick Ryan's leaking hole. "Damn, this is some sweet-tasting cum," he said after the first few licks. "No sense in letting it go to waste!" He spent the next several minutes making oral love to Ryan's hot cum-filled asshole, hungrily slurping up all of the loads of jizz the studs had shot there.
Meanwhile, Ashton stood behind his friend, smiling incredulously and jerking off his impressive pole. He had about ten inches, long and thin and white, just like he was. His body looked as terrific and sinewy as I had always expected and dreamed. Totally naked and rock-hard, he soon grew impatient from being excluded.
"Dude," he said in a low tone to Seann, "I came here to breed some boy's hole. If you don't move away from that star-pussy in the next few seconds, I'm going to ram into your hot little jock-tube and blow my load in you instead."
"Go ahead, stud," Seann retorted, pausing his pussy-eating long enough to reach back with one hand and hold open his tight, hairy buttcheeks. "Fuck knows, it's our lunch break, and if we weren't over here, this is what you'd be doing anyways. You know I love your meat inside me Ashton. Give it to me nice and hard, just like you always do."
"Fuckin' right," Ashton said, giddy with horniness. "You asked for it." He lined up his slim missile with Seann's hot brown hole, and in one long fluid motion, pressed the whole thing inside. Seann let out a loud exclamation of mixed pain and desire. Seconds later, he was back to eating Ryan's cum-filled trench with renewed passion as Ashton throttled his star-meat in and out of Seann's butch hole.
After a while of this, Ryan pulled his mouth off my cock, jerking it as he whimpered: "Dudes, that tongue feels good but I need some real meat inside me. Now!!"
On cue, Ashton pulled out of Seann, and Seann sat upright, leaving Ryan's hot pussy exposed, fresh and clean. "It's all yours, stud," he said to Ashton. "Fill him up...go nuts."
And that's exactly what Ashton did. His long dick probed deep into Ryan's ass, and after he bottomed-out in the blond boy's bitch-pussy, he immediately withdrew and began a fevered assault. Even Ryan was taken off-guard by this. Ashton had leverage and power, and he used both to hammer as relentlessly deep and hard as possible. Ryan was screaming with lust and satisfaction: "Yeah! Oh, yes! Ashton! Fuck me...use my hole, please! Oh man, fuck me, dude, do it...your big cock feels so fuckin' good..."
Meanwhile, Seann got onto the mattress next to me, kneeling and then grabbing me by the shoulder into a solid lip-lock. I melted into his strong embrace. Instinctively, I wanted him to fuck me. I figured Ashton would take a while, and during his assault on Ryan's ass, no one would miss either Shawn or myself.
So I got onto all fours next to Ryan's squirming, ecstatic body, and moments later I felt Seann's hot dick pushing into my chute. It was an inch or so shorter than his co-star's mammoth cock, but it was also significantly thicker. His dick inside my horny cum-tube filled me with pleasure and wild sexual abandon. I reached over and tongue-kissed Ryan deeply as Seann continued pummeling my back door. Both Ryan and I love to kiss while we are being deep-fucked, and in this situation, it was remarkably hot: The sexy studs of a new movie were ass-banging us while we made out with each other!
Both boys continued until, before long, we felt their loads escaping into our hungry twats. I knew Ryan was the star of this sex show, so I respectfully moved aside to see what would happen next. The answer surprised me.
Seann's dick never quite went soft after cumming in my hole. Likewise, Ashton was at full-mast. He pulled on it playfully as he asked Ryan: "OK, slut-boy. You ever take two dicks at once?"
Ryan's eyes flared with excitement. "Yes," he answered, somewhat meekly. "But not in a long while." I could tell he was instantly aroused by the idea. So was I!
"OK, get up and let me lie there," Ashton commanded. Ryan obediently rose and got up off the bed. Ashton laid down in his place. His body looked fantastic, and his hard cock was thick and ready to shoot more cum. "Now, sit on my cock."
Ryan straddled Ashton's sexy midsection, reaching behind himself to grab the young star's pole and line it up with his own hungry pucker. With Ashton's previous cum-load as lube, the giant cock made it back inside easily. When they were situated, Ashton waved his buddy over.
"Oh man, yes Ryan, that feels good," he praised the boy as Ryan began some gentle up-and-down motions on his cock. "Alright, buddy," he said to Seann. "You know what to do. Just like that time with your brother."
Ashton grabbed Ryan's torso and pulled him as far forward as possible, while keeping Ashton's big prick plunged fully inside the bottom's sexy ass. Seann spit in his hand, lubing up his hard cock, and then got on his knees on the mattress, lining-up his fat cock with the portion of Ryan's pucker that was exposed above Ashton's dick. Hard as a rock, he pointed his dick at the hole, and with a little wiggling, pushed the head through."
"OH!! FU-U-U-UCK..." Ryan yelled at the intrusion. "OH...man, shit..oh fuck...yes, wait, wait...yes, that's it...oh man, it's really in there...please stud, please fuck me...double-breed my hole..."
That was all the encouragement they needed. Sure enough, Seann had gotten his hole fat cock inside Ryan's impossibly accommodating ass-ring, and was soon hammering in and out of him in long, forceful strokes. I had never seen Ryan (or anyone) get double-penetrated before, so I sat and leaned against the wall of the trailer, beating myself off. Both huge meaty dicks stayed 100% hard as they treated Ryan's sloppy butt to the fuck of his life. Seann did most of the stroking, but Ashton was able to get into the action as well, thrusting upwards to sink his dick in as far as possible, or otherwise just letting the friction of being pressed between Ryan's ass-walls and Seann's plunging dick give him all the pleasure it could. On each stroke, Seann's heavy balls slapped against Ashton's where they hung below the sexy hole to which they were giving their attention.
Seann was the first to cum. He shot most of his load inside Ryan's ass, but the orgasm must have made his dick slippery, because it popped out soon enough, and the last several jets shot in a steady stream onto Ryan's lower back. When Seann was done shooting, Ryan and I weren't far behind. Ryan sat upright, now riding only one monster cock, and unleashed a terrific volley of boy-juice all over Ashton's sexy chest. At the same time, I lurched forward and sprayed my own load in about the same place. Finally, Ashton fucked Ryan powerfully from the bottom, staring deep into the boy-toy's smoldering eyes and jackhammering his dick straight up into the slut's twat repeatedly until he screamed loudly and delivered a powerful load up into Ryan's belly.
To complete the round-robin, I got on my back and let Ashton drill me hard with his third fuck-load of the day. Meanwhile, Ryan got some one-on-one action with Seann, lying back next to me and spreading his legs for the jock stud to pound his hole mercilessly in and out. Again, Ryan and I kissed deeply as our visiting studs pounded the hell out of us. After both superstar guests shot their third and final loads of baby sauce into our hungry asses, they informed us they were late getting back to their own movie, but would definitely be by again soon for some additional lunchtime fun.
As they exited the trailer, it was a sign for others who had been waiting outside to join in. A queue of four or five more extras, all sexy and hung (I'd made sure of this with the production assistant during casting), were all outside, smoking or just chatting, waiting their turn. As the first few entered the trailer, I snuck down between Ryan's hot legs for a little lunch of my own, and I sucked out the hot loads that Seann and Ashton had shot there. Moments later, I stood up, cum covering my face and chin, smiled at Ryan, and then turned to go back to the front of the trailer, where my clothes and my paperwork and my cell phone waited.
In the process, I passed the first extra coming by for his trick-time with Ryan. He was gorgeous, a strapping, scruffy type in his early thirties who I hadn't seen on the shoot before. (I found out later he was an assistant cameraman, hired that day to replace another one who'd quit.) I smiled with lust when I saw him and the big cock he had hanging between his strong legs. Looking him deep in his blue eyes, I said:
"He's all yours, man. Fuck this cunt's hot sloppy ass with everything you've got. He lives for cocks and cum!"
Once, a few weeks later, I happened to stop by Ryan's house with some papers. There was no answer at the front door, so I walked around to the playpen, only to find the door locked...an unusual occurrence, because in general Ryan schedules his sex invitations close enough together that the tops who arrive to fuck him can just let themselves in. Puzzled, I called his cell phone, but got his voicemail instead of his voice in response. I listened at the door: he was definitely having sex, very good sex from the sounds of it. In fact, he seemed to be hollering breathlessly as some one (or several people?) eagerly pounded his hole.
I finally went back to my car in the street and made some other business-related calls. About twenty minutes later, the door to the playpen opened, and two familiar men made their way quickly to a car parked next to Ryan's in the driveway. It was Ben Affleck and Matt Damon! Of course, I had watched Matt once in action at Ryan's new love nest, that day he fucked Ryan silly in the sling. But I had still never met Ben, nor had I had any contact with Matt since that special occasion. I had assumed from things Ryan had told me that the two of them were lovers. The sight of them now, together, made my dick jump instantly, even before I put together the fact that they had just been fucking my client. This was Ben and Matt, in public and in the flesh, hurriedly departing a tag-team bang on Ryan's hole. God, what fantastic luck!
"Please," I begged Ryan the next day. "You've got to let me tag along sometime when you're with them."
I generally didn't make such requests of Ryan or any client--I had been in the business long enough that I didn't get starstruck easily. But the thought of Ben and Matt fucking Ryan--together!--was too tantalizing to pass by. It dominated my fantasies for weeks after this chance encounter.
"Can't do, sorry," Ryan said, unfazed by my uncharacteristic schoolgirl-like behavior. "With Ben and Matt, when they both visit together, it's a locked door. Unless, I guess, they personally invite you along."
We both knew there probably wasn't much chance of that happening. "But what about that time? With Matt? In the sling...?"
Ryan shrugged. "Special occasion, I guess. How did you get ahold of him that day? Didn't you set it up?"
"No," I said. "I just arranged it with Ethan and the contractor dude. Ethan brought the other three along."
A few weeks later, it became an issue again. I stopped by Ryan's trailer to drop off some mail that had come to our office on his behalf. Ryan didn't know I was dropping by, so he was slightly surprised when I let myself into the trailer to find him naked on the bunk, alone, his legs bent and propped up on a nearby table, and a dreamy look that generally meant a guy had just satisfied himself up Ryan's ass.
"You missed it," Ryan said. "Ben and Matt were just here...they left about five minutes ago."
I did a double-take, incredulous. "Here? In the trailer?"
"Uh-huh. It was hot." Ryan's bent, slender legs were spread like a butterfly. He reached casually between them, sticking the bent tip of his middle finger up inside his asshole, producing a long string of cum which extended upward as he carried a scoop of it to his tongue. "Mmmmm..." he moaned. "That's good stuff. You want some?"
I was transfixed, and didn't reply; I simply dropped between Ryan's legs, fully clothed, and pressed his thighs apart with my palms. He shuffled down to more of a slouching position, giving me better access. I dug my tongue into his cum-filled asshole, drinking out the loads. I was sucking Ben's and Matt's cum out of Ryan Phillippe's ass. It was the best, most intoxicating sensation in the world.
"Mmm-mmm..." Ryan continued, louder. "Oh yeah, that's good. Suck my sore hole. They fucked it hard!"
I pulled away, breathless. "Oh yeah? How many times did they cum?"
"Four," Ryan replied. "Matt only came once, but Ben was a three-timer. That animal...!"
I groaned with happiness as I resumed eating my superstar jizz-meal. It was the closest I've come to this day to ever observing the south Boston duo in action, but Ryan has told me tales about them that no one else knows, so I get my thrills vicariously, I suppose. Besides, it's still only the year 2000...maybe in the new century my luck could change?
To be continued...
Sorry this chapter took so long. 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.