Celebrity DILF's
This is a fictional story that involves consensual sex between people over the age of 18 and does not imply the sexuality of the people involved.
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This series will be short-Ish stories based on the hottest DILF's in Hollywood as they plough their way through the new 18+ talent in the industry.
Celebrity DILF's part 1- Ryan Phillipe & Tom Holland
Ryan Phillipe loved awards ceremonies, he loved dressing up and getting his photo taken on the red carpet, dining with some of the top celebs and drinking until he couldn't see anymore. These were some of the reasons why he loved these ceremonies, and the 2018 awards were going to be one of the best yet. But the main reason he loved these ceremonies was that usually by the end of it he had someone bouncing up and down on his cock as he slammed them into the mattress. Ryan didn't care the gender of the person bouncing on his cock, a pussy, or an asshole as long as it felt good to him, and they pleased him well then it could be anybody getting the present of his cum deep inside them. And this year was even more special, he was hosting a little... well, a rather large party afterwards so there would be an array of talent for him to choose from. As Ryan walked the carpet he smiled for the cameras and once inside he was impressed at the talent that was to offer. As he sat down at his table he looked over and saw the cast of the latest Avengers film at the table opposite him, he stared at the cast scoping out the talent that was to offer stopping at young Tom Holland who at 22 was an up-and-coming star in the making. As the cast chatted Tom looked over and saw Ryan staring at him, he awkwardly smirked as Ryan winked at the young star making Tom awkwardly blush as he turned away and continued chatting, "Fight it all you want boy... I know you want it." He grinned carrying on with the night. As the night continued, he just became hornier and hornier and as he saw Tom walking towards the toilets he sprung to his feet, "Phase 1 initiated", he grinned to himself following the boy. As he walked into the toilets, he saw that they were empty, Tom must have used a cubicle but nevertheless it wouldn't be a problem. He went up to the urinal pulling out his semi hard cock and waited. After a minute he heard the door unlock and out walked Young Mr Holland, Ryan turned, "Ahhhh Tom... Tom Holland isn't it" he grinned as Tom blushed again, "Yes Mr Phillipe... nice to meet you." Tom walked to the sinks and began washing his hand as the man began to piss, "Great job in Spiderman," he grinned as Tom just blushed, "Although... that tight costume I couldn't do it... it'd be a bit tight on the old... down below" he chuckled. "Oh yeah really" Tom stuttered as Ryan put his hand on the sink, "Really...don't think those suits are designed for big cocks like mine." He stopped pissing and looked down as he saw Tom glimpse over and look down, the boy's mouth falling open at the size of his soft cock, "Yeah...I'd love to play a superhero but I don't think they have one called Captain big cock" he grinned as Tom ran over to dry his hands, "Y...yeah I don't think so...See you Later Mr Phillipe". Ryan chuckled to himself as he stuffed his cock back into his trousers.
That was phase 1 of his plan completed, he had sparked interest in the boy and now it was time for phase 2. As the night ended the celebs were chatting and Ryan saw young Tom about to get into a taxi. "TOM... TOM" He shouted as the boy turned around and went bright red, "Hi Mr Phillipe" he muttered as Ryan slapped his shoulder, "Hey were friends... call me Ryan," Tom nodded as Ryan raised a brow, "So Tom you aren't going home, are you?" Tom nodded as Ryan smirked, "Why don't you come to my after party...it's only a small gathering but I think you'll have loads of...fun" he grinned winking at the boy, "I can't...I got to go..." he muttered as Ryan looked disappointed, "Oh now come on a young hunk like you not going to a party...I'll DM you my address", Tom nodded again, "umm...ok I'll come" he muttered as Ryan walked away. He got out his phone and typed in his address but not before "Accidently" sending Tom a little present, a photo of him in his underwear, blue tight boxers where his bulge looked insanely big, "Shit sorry man...wrong photo", he replied grinning as he wrote down his address and waited for a response. A couple minutes later Tom replied, "It's ok Mr Phillipe...and yeah you couldn't fit in a superhero costume that's for sure," Was the man flirting with him, either way Ryan liked it. Cut to an hour later and at his party the drinks flowed, and Ryan had gotten into the hot tub with some celeb friends. As he sat there he saw Tom approach, "TOOOOOOOOM, glad you could make it man" he grinned standing up to reveal the same blue boxers as in the picture making Tom's eyes bulge out of his head, "Wow you're...nearly naked" he chuckled as Ryan scoffed, "I'm not naked...yet...anyway why don't you come join us" Tom shook his head, "I can't I don't have any shorts". Ryan frowned, "Now...now I'm not wearing shorts... just get in wearing underwear you can borrow some underwear off me." Tom looked around and nodded, "Ok fine" he chuckled removing his shirt and trousers, the man's smooth slightly muscled chest making Ryan's cock throb. As Tom got in Ryan turned on the bubbles and a few minutes later Tom was sat next to him. Unknown to the boy Ryan removed his underwear letting his large cock sway back and forth hidden under the water. "See not that bad, is it?" Ryan asked as Tom shrugged his shoulders, "Nah not bad at all and thanks for inviting me I'm having a great time." "No problem anytime," Ryan grinned as he pulled the boy in for a hug "Accidently slapping the glass of wine from Tom's hand sending it into the water. "Oh fuck...I'll get it" Tom grinned reaching into the water gripping something hard before his eyes flew open and he looked at the grinning man, Tom had the man's hard cock in his hand wrapped around the man's large girth, Tom couldn't say a word he didn't want to ruin the party. He felt the man thrust a little and Ryan bite his lip as Ryan wrapped his hand around the boy's and pulled it up and down... still with 6 others in the tub.
Tom felt the cock go up and down getting harder and harder, as Ryan continued talking to the other guests. Tom couldn't believe this was happening, he had never been with a man before but as he wanked the man off, he realised his own cock was hard as a rock. Ryan stifled his moans as the jerking got faster and faster, he didn't want to cum in the hot tub, so he pushed the man's hand away and swam over to the other side as Tom sat there dumbfounded. Tom made shallow conversation with all the guests in the tub every now and then Ryan looked over at him and bit his lip lifting up the man's leg and rubbing his foot on his cock. It felt so fucking good, he had the boy right where he wanted him, but he enjoyed toying with the boy, at one point he asked Tom to fill his glass up making the boy have to swim next to him to pour, as he did this Ryan gently kicked the boy's leg making him fall on top of him, as he fell Ryan pulled the back of his underwear down and the boy fell ass first onto his crotch, the man's hard cock rubbing up and down the boy's crack as Tom went wide eyed once more as he felt it against his hole. "Oops sorry man" Ryan grinned as Tom stuttered, "It's all right Mr... Phill... I mean... Dadd... I mean Ryan." As the party died down it was just Ryan and Tom in the hot tub sat at opposite ends. Ryan sipped his drink and looked at the boy, "So Tom... you had a good night?" Tom blushed again, "Yes...it's been...eventful" Ryan smirked, "Oh yes it sure has...it doesn't have to end you know", Tom looked confused as Ryan leant over and turned off the bubbles revealing his rock solid cock that he had been jerking the whole time, "We can carry on this party if you want?" Tom was nervous as hell, "I... I can't...it was fun, but I can..." He was cut off as the man leant up, his cock breaking free from the water and Ryan pursed his lips and spat down onto it making it glisten, "You sure?" Tom licked his lips as Ryan walked closer and reached out grabbing the boy's hand and wrapping it around his shaft once more, "Fuck...so thick" Tom muttered looking up at Ryan who just smirked, it was the first time Tom had seen it hard, the bubbles had hidden it before and it looked fucking hot, 9.5 inches long and as thick as a cucumber, his head light pink and his shaft slightly curved upwards, his pubes brown and neatly trimmed and his balls were slightly tight in the sack because of the cold and were lightly haired. He jerked it back and forth making Ryan grunt and mutter, "Fuck yeah," Ryan looked down at the boy and said 3 words, "Wanna suck it?"
Before Tom knew it, he felt a hand on the back of his head and his mouth had opened and he was sucking off Ryan Phillipe, the man's cock head in his mouth as he licked around it. Now Tom lied earlier, he had been with 1 man before, Chris Evans had fucked him on the set of Civil war but that was a while ago but Tom had seen enough porn to know how to suck a cock, he pulled the head out and lapped at it sliding his tongue around the sensitive head smearing pre-cum all over it as he flicked his tongue at the man's piss slit, "Oh fuck yeahhhh" Ryan moaned looking back making sure the garden was empty, he could see Chris Hemsworth butt naked face down in the grass passed out, "I don't think he'll tell anyone" he grinned as he put his hands on the back of Tom's head and began to push the boy down. Ryan thrusted hard grinning at the boy as a loud gurgle sound that filled the garden as his cock completely disappeared down the boy's throat, his pubes hitting the boy's nose. Ryan smirked looking down at the fat cock that was all the way down Tom's throat. The boy had tears in his eyes as he looked up at the hunk above him reaching up and stroking the man's toned stomach. Ryan groaned into his hands as he felt the warmth of the boy's throat around in on his cock. This was a tight throat he knew the boy hadn't sucked many cocks before. Ryan pulled back holding the head in the boy's mouth as Tom coughed before he stuck out his tongue and began to lick around the head collecting the salty pre-cum of the stud swirling it around on his tongue. Ryan grinned chuckling to himself as Tom began to lap and suck flicking his tongue at the piss slit all while rubbing the older man's furry balls, rolling them around his fingers and pulling on them slightly, making Ryan grunt and moan, "oh fuck...of Fuuuuuck you sure you haven't done this before". Tom looked up at the man and smiled As Ryan pushed hard on the back of his head as his mouth began to sink down on the cock, Ryan's eyes widened as inch after inch of his thick man meat disappeared into his throat, Tom was either a liar and had sucked cock before or he was naturally talented at sucking cock, as he inhaled the cock without gagging or choking and as his nose pressed against Ryan's pubes Ryan reached out and wrapped his hands around Tom's head. He began to fuck his cock into the boys throat his hips thrusting back and forth and his ass wobbling with each thrust. Ryan could see his cock bulging in the boy's throat turning him in even more, "Ahhhh fuck...take it...take all my big fucking cock". He grunted as Tom finally began to cough and splutter as he pushed hard leaning over the boy pinning him to his cock, Tom spluttered salvia pouring down his face as Ryan rammed his cock hard and pulled the boy's face back and forth coating his throat in pre-cum. Saliva dripped down his balls as Ryan felt Tom's hand slapping his ass. "Fuuuuuck boy... you're a natural at this" Ryan grinned feeling his cock throb in the tight throat as it gripped his shaft making each thrust more pleasurable than the one before. Suddenly the men heard a noise.
Ryan looked over and saw Chris Hemsworth starting to wake up, "Fuck...get out hide" he muttered pushing Tom out of the hot tub and jumping out himself, As he stood behind the tub Chris stood up, "Fuck man...what did I drink?" he asked as Ryan who was covered by the tub lifted up his cock and pushed the boy into his hairy balls, "Uhhh...man you drank a lot...like a lot" he tried not to moan as the boy lapped at his balls before sucking hard on the left nut tasting the man's salty balls letting the favour wash over his tongue, "Fuck why am I naked?" Chris asked as Ryan shrugged his shoulders, "Man I have no idea... but your clothes are inside I think" Chris nodded "Cheers man I'm gonna go... enjoy your night." Ryan smirked watching the man's muscled ass as he walked up the garden and into the house. "Fuuuuuck "Ryan moaned looking down at the boy who had both of the man's balls in his mouth and sucked them hard making them drip saliva. Ryan reached out and rubbed his balls all around the boy's mouth staring at the boy's innocent eyes looking up at him before he pulled the boy up and pulled him upwards sliding his tongue inside the boy's mouth hungrily tasting the boy as their lips clashed together. It was clear that Ryan was in charge of this kiss and as he pulled away a string of saliva connected the pair. "Wow Mr Philippe that was close" Ryan smirked, "Too close... why don't we go inside and continue this party" Tom nodded and as he went to walk away Ryan slapped the boy's pert smooth cheeks making them wobble, "Fuck I need to destroy him" Ryan grinned.
As soon as the men got inside Ryan grabbed Tom and pushed the boy onto the pool table, "Hold your legs up boy...you're about to feel sensations you never felt before" Ryan grinned spitting down onto his finger before rubbing it against the boy's tight pink hole, "Fuck that's a hot little pussy" Ryan grinned as he watched the boy's eyes widen as he pushed his wet finger inside the boy, whistling as the boy's hole gripped it tightly, "Fuck Mr Phillipe...that feels good" Tom moaned as Ryan curled his finger around like a hook and played the boy's prostate like a guitar. Wave after wave of pleasure shot through the boy making him throw himself up as Ryan caught him and held him whilst he added a second finger inside staring at the boy and grinning as Tom's hole was stretched open. "Wow boy...you're hole is so tight" he grinned as Tom's legs shook, he was wearing the boy like a finger puppet and as he slammed his fingers in and out he felt Tom grip his fat cock and begin to suck on the head hungrily lapping at the head pulling the pre-cum from his cock as he used the boy's hole like a toy stretching his fingers apart making the boy squeal, "AHHH FUCK...FUCK MR PHILLIPE...YES...YESSSSSS" Tom Screamed as Ryan thrusted his cock in and out of the boy's throat. Turning the boy around on the table so his head hung over the edge he pulled the boy's ass upwards and sunk his cock into his throat leaning over trapping Tom on his cock whilst still having 2 fingers deep in the boy's guts. As he held the boy down, he felt the boy's hole spasm around his fingers going impossibly tight the longer he held the boy down. He looked down at the tear-stricken boy watching his cock bulge in the boy's throat. He loved breaking in the new talent in Hollywood, and he was incredibly good at it. Ryan rammed his fingers in hard feeling the boy squeal on his cock before ripping them from his hole grinning at the slightly gaping hole that winked at him. Tom coughed and spluttered as Ryan reached down and thrusted his fingers into the boy's mouth, "Suck them" he ordered as the boy lapped his tongue over the fingers tasting his own hole as Ryan just stood there grinning. "You did good boy... really good" he muttered pulling his fingers out of the boy's mouth and helping him to his feet before wrapping his hands around the boy's legs and lifting him off the ground. Tom wrapped his legs around the hunk as Ryan leant over and whispered, "You did good pleasuring Daddy... Time for Daddy to pleasure you" he smirked carrying the boy over to the kitchen counter. He instructed Tom to raise his legs once more, "I'm gonna eat that pretty pussy" he winked, "Thank you Daddy" Tom grinned.
Ryan spread the boy's cheeks his cock throbbing at the sight of the pink pucker once more. "Oh, this is gonna be so good" he grinned crashing his tongue against the tight pink quivering pucker. He immediately began to lap and suck at the hole; Ryan loved eating ass had eaten a few women's holes in the past, but man ass was his favourite, he could make a man squirm just by a lick of his tongue and he fucking loved making men squirm. Tom thrusted back and began grinding his hole. against the man's face feeling sensations never felt before, the tickling wetness felt so good he just wanted more and more, he shook his cheeks on the man's face before shoving it hard feeling Ryan' stubble scratching his hole which sent tingles up and down his cock, Tom looked down and noticed his cock was rock hard , he reached down and began to jerk his cock thrusting hard against Ryan's face. Tom pushed hard, his eyes rolling back in his head moaning "MMMMM FUCK YES" as Ryan's tongue was deep in the hole slurping and sucking at the tight heat. This ass tasted fucking amazing; it was intoxicating. Ryan was going crazy in the hole ramming his tongue as hard as he could squeezing the fat cheeks around his face and sucking the hole hard. Ryan pulled out briefly licking his lips all he could taste was tight boy hole and he fucking loved it. "Keep licking Daddy please" Tom moaned pushing the man back between his cheeks as Ryan ate his ass out like it was his last meal whilst jerking his own cock making pre-cum ooze onto the marble floor below. Ryan licked all the way up the boy's hole before lapping up the boy's balls and taking him by surprise by putting the boy's cock into his mouth and sucking up and down the shaft tasting all the boy's pre-cum as he sucked with gusto easily taking the whole cock as Tom stared down at him in shock ad Ryan pulled off and licked around the head whilst grinning at the boy, "You got a tasty cock there boy" he grinned sucking down like a vacuum making Tom's legs shake and his eyes roll back yet again. Ryan continued to rub the boy's hole whilst sucking his cock getting it ready for what was going to happen next. He pulled off the boy and helped him to his feet before kissing the boy passionately holding him under his chin as their lips collided and He slid his tongue in and out of the boy's mouth before gently pulling away, a string of saliva connecting them as he leant over and whispered, "Now Daddy pleased you why don't you please Daddy by letting me stick my cock in your ass". Tom went wide eyed, he looked down at the solid hard cock, "It's so big Mr Phillipe...I don't think I can take it" Ryan stroked the boy's cheek, "You can take it...I'll go slow ok" He stared at Tom who nodded, "Ok Mr Phillipe just be gentle". Ryan smirked; he would be gentle...at first.
"I think we should do this in the bedroom... make it more comfortable baby" Ryan grinned as Tom nodded. Ryan grabbed the boy's hand and pulled him up the stairs, his cock bobbing up and down with each step making Tom nervous, how could that monster fit inside him...it was gonna hurt and he knew it. Ryan opened the bedroom door and Tom grinned at the emperor size bed, "Big enough" Ryan grinned as Tom nodded. Ryan pulled Tom onto the bed kissing the boy before making his way down the boy's body planting kisses down his chest, stomach, cock and then down his legs before lifting them up onto his strong shoulders as he reached down and slapped his cock against the hole before spitting down onto the hole rubbing it into it and making it glisten. He then repeated this rubbing the saliva onto his cock as he braced his legs and aimed at the hole, "Ready boy?" Tom nodded his eyes rolling back as he felt Ryan press against his hole. It put up a lot of resistance making Ryan grunt and push harder and harder until finally his fat head burst inside the boy...as well as 4 inches of thick Daddy cock. "FUCK" Tom wailed shooting up as Ryan grinned, "Maybe I pushed a bit too hard but HOLY FUCK IS THIS ASS TIGHT" Ryan grinned holding his cock in place letting the boy's spasming hole get used to his fat cock that stretched him wide open. Tom led there panting, he was nervous as hell, the thickest part of the man wasn't even inside him yet. Slowly Ryan began to push pulling the boy onto his cock as it split the boy's hole wide open, "AHHHH FUCK...STOP MR PHILLIPE...IT'S TOO BIG", Tom screamed as a tear rolled down his cheek, "Boy I'm nearly all the way...just take it" Ryan grunted as a loud slapping sound filled the room as the rest of his cock smashed inside the boy. Tom opened his mouth to scream but no sound came out as he looked up at the hunk who just grinned, "See told you it wasn't that bad" he chuckled as Tom wailed, "Easy...for...you to say...It fucking...fucking hurts man" Tom squealed as his hole gripped the shaft hard. Ryan leant down to kiss the boy, his cock shifting inside making the boy wail into his mouth as he slowly pulled back and thrusted back inside slowly fucking the boy as they kissed pulling more and more out with each thrust until when only 2 inches was inside he rammed inside the boy grinning as he began to fuck the boy fast and hard leaning up and using the boy's legs to pull him onto his cock as he thrusted inside. Tom moaned in a mixture of pleasure and pain as his ass was torn apart by the fat cock that was rearranging his insides looking up at the hunk who looked so fucking sexy, his chest glistened with sweat and his pecs bouncing with each thrust, "It should be illegal to be that hot" Tom smirked to himself as he was used like a human fleshlight.
Ryan's balls slapped against the man's hole faster and faster echoing around the room. Tom reached out and ran his hands up Ryan's sexy body feeling the man's hard toned pecs between his fingers, reaching up and taking the man's sexy pink nipple between his fingers and tweaking it making the older man growl and his cock throb inside, "Like my tits boy...well next time you can suck them" he chuckled. Ryan slammed into the boy hard over and over slap after slap of his hairy balls were all that could be heard, they switched positions into doggy so Ryan could slam the boy harder, He stared at the boy's gaping hole, it made him excited that his fat cock had caused this. He put his arm around Tom's throat and pulled him back sliding himself inside once more and pounding the boy mercilessly. Ryan was thrusting in so hard at one point Tom's eyes shot open and Ryan continued to fuck faster and faster his arm wrapped around Tom's waist holding him in the air using the bending of Tom's body to thrust in harder, Tom smirked and moaned, "YESSS...YESSSS DADDY FILL ME", This inflated Ryan's ego because his thrusts became almightily fast, Tom Leaned back and began to kiss Ryan's tight taught chest before taking his very sensitive right nipple into his mouth before slowly biting and sucking on it. Making the top growl as he smashed into the boy's hole feeling every inch milk the pre-cum from his cock. Tom lapped and sucked at the man's nipple sending shivers up and down Ryan's thick cock before pulling hard making the top growl, "You trying to make me cum boy...you want my fucking cum...yeah...YEAHHH", "Yes DADDY...FUCK ME...BREED MY ASS" Tom squealed as Ryan pulled the boy up and turned around slowly sitting on the bed as he led down with Tom on top he ordered, "Lie back" Tom did as told as Ryan raised his legs folding the boy in half, "Prepare...this is gonna be rough". Ryan began to pound the boy his teeth gritted as he ground his cock in and out pulling all the way out before slamming back inside. making the boy's eyes roll back and his cock flail up and down, his balls slamming against the boy as he fucked harder and harder and harder. Tom could feel the man's warm sweaty body stuck to his own and it turned him on even more, the man might have been in his mid-40s, but he still fucked like a man half his age. Tom then did something that surprised even himself, he squeezed hard on the shaft making each thrust tighter and tighter, "Oh fuck... OH, FUCK BOY YOU'RE GONNA MAKE ME CUM" Ryan moaned as his balls tightened up and each thrust became more intense, his thrusts became erratic, and his cock throbbed. With an almighty slam making Tom wail in pain Ryan screamed, "I'M CUMMING... FUUUUUUCK I'M FUCKING CUMMING," His legs shook, and his eyes rolled back as his cock pumped load after load of cum deep inside the boy's hole. His cock pulsed visibly as he shot a mammoth 11 ropes of thick DILF cum deep in the boy's guts. As the last spurt shot out, he sighed and collapsed letting go of the boy as his cock slipped from the hole and dribbled the last spurt onto his leg. Tom immediately rolled off wincing at the pain in his hole.
Ryan led there for a while, his balls feeling empty as Tom squeezed his hole shit to keep the cum inside. Finally, after a while Ryan looked over, "Not how you expected this night to go is it?" he smirked as Tom ran his fingers over the man's sweaty chest, "Not exactly... but I'm so happy it turned out this way" he grinned as Ryan pulled him in for a steamy kiss. "Fuck... I'm covered in sweat... need a shower" Ryan muttered before grinning at tom. "Wanna join me boy... see if this old man can fuck you again" Tom reached down grabbing the man's semi hard cock, "There's nothing old about you" he grinned pulling the man by the cock into the bathroom and closing the door.
Thank you for reading this story, I love reading comments on my stories so any feedback is gratefully received and any suggestions for the next chapter will be taken into consideration. I will do any male celeb from either the UK or the USA. Send ideas to Anonbucket1995@outlook.com