Hollywood Hills: Drake

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A film star's devoted personal assistant pleasures her boss.
2.7k words
4.05
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Part 1 of the 2 part series

Updated 08/30/2017
Created 07/21/2011
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Drake Eden looked down at the Carmen Electra lookalike who was working her mouth on his cock. She was what his personal assistant, Claudia bitingly called a "mattress"- model/actress/waitress. In this case, she was a 'flight attendant' for all the studio knew. Drake had noticed her at an industry party. She had been serving cocktails in a micro-mini skirt and stripper heels. Usually, Drake went for classier women, but it wasn't like he wanted to date her. Drake didn't want to date anyone, really. The last movie was a blockbuster, and the one before that earned him massive praise in Cannes. There was the promotion tour coming up that would take him all over Europe, Asia and Latin America, and the new film would start shooting in two months. There was no time for dating. Drake sipped his almost trademark glass of cognac as the WannaBeCarmenElectra sucked sloppily on his cock. He was getting bored with this. It was an awful blow job really. No technique.

Mr. Big Time Hollywood Movie Star Drake Eden would never admit this in public, but he really didn't care too much for banging women who were tens. The thing was, tens feel they don't have to work at all. They think their looks will make up for laziness in bed, among other things. In Drake's opinion, great sex required intelligence, and that was something that women like this usually lacked. But bless her, she was making a good show of being ridiculously hot while failing at the blowing part of the job. He shifted a little, giving her a better angle. She was on her knees in front of him, the hum of the G550 private jet overriding any humming she might be doing. He took a handful of her hair and began working her head on his cock at a respectable pace. She suddenly put her hands up and mumbled around his shaft,

"Careful, you'll yank out my extensions."

And just killed it for him. His cock went a little limp in her mouth. Not completely soft, but enough to put him off. Maybe he was jaded. This kind of fuck didn't do it for him, despite her phenomenal looks. He withdrew from her mouth and stuffed his cock back in his pants, making a polite but quick excuse about stress and how he couldn't concentrate. He told her to drink some champagne, enjoy the flight, have fun in London, which was a polite way of saying have fun... but not with me. She didn't seem to mind. She gave him a wink and busied herself at the plane's bar, pouring herself a glass of champagne. Drake was considering sticking his hand down his pants and finishing the job, just to take his mind off of it, when he heard Claudia's voice just behind him. How long had she been there?

Fuck yes, Claudia, he thought. That was exactly what he needed. Claudia Reed, of the big luscious breasts and the impossibly tight pussy that stayed tight no matter how many times she fucked. Claudia Reed, of the sweet, angelic face that could have been fourteen or forty, but in fact she was thirty-three. Claudia Reed, who was married to a buffoon, Martin Reed, who owned a furniture store in Van Nuys and did cheesy late night furniture store commercials with fucking parrots and pirate costumes. Claudia had been a housewife for years, completely ignored by her husband, who up until she began working for Drake, had been her first and only lover. She had claimed to not have much interest in sex after thirteen years of marriage to a man who fucked her on average of once a month for approximately four minutes, and every time he finished on top of her with a grunted "aw fuck yeah baby! Ugh!" before he emptied his drippy load and promptly went to sleep. Claudia might have had little interest in sex, but that was before Drake bounced her on his cock until she came so hard she blacked out for a few seconds. After that, Claudia Reed was a changed woman. Drake taught her the real Hollywood business; the negotiations, the game, the parties, the bullshit... and he taught her how to fuck.

"Feeling a little frustrated, Boss Man?" She purred into his ear. She had been born and raised in New Orleans and that lingering touch of Southern belle instantly made him hard again. He was already thinking of her full red lips on his cock, sucking him dry.

"I'll bet you could fix me right up." He said with a sly smile he knew she loved.

Claudia, bless her, moved in front of him and dropped a pillow onto the floor to kneel on. She gathered up her mass of raven black curls that made her look like a Fellini starlet and wrapped it in a loose knot behind her head- out of her way. Claudia was serious about blow jobs. Off came the trendy gold frame glasses that masked her huge green eyes. She was all curves; tits, hips and ass, thick thighs and shapely legs. It was her tits that made men lose their minds. She was not a ten, but her tits were a fifteen. She was a small woman, at only five foot one, though a bit plump. Those tits were the kind of tits that when you see them, your mouth waters instantly. Big and still sitting up high on her chest, they were natural, and milky white and had perfect half-dollar size nipples the color of dusky roses that seemed to stay perpetually hard. The kind of tits you expect to suck and feel milk squirt from. Tits of Eternal Nourishment.

Claudia had a little weight around the tummy. Not much, but she was by no means any kind of waif. This one small bodily "flaw" as she considered it was what made most men in the ranks of Hollywood overlook her. Drake liked it. He liked fucking her doggy style and smacking her plump ass, watching the ripple of flesh. He liked watching her big tits bounce in his face while she rode him. There was one other gem of a natural talent Claudia reed possessed: she had a delicious pussy. Drake had eaten some pussy in his lifetime, but never had he tasted a pussy as sweet and delicious as Claudia Reed's perfect little honey-pot. It was a beautiful pussy, neatly tucked in, none of that meat curtains bullshit. No, Claudia had a model perfect cunt. She liked that word too- cunt. She liked it when he said, "show me your pretty cunt" and she would open her legs and spread those juicy pink lips for him. She tasted like fruit and honey, and he would eat that pussy like it was the only meal he'd had in weeks any time Claudia wanted.

Right now, she was on her knees, working his cock in her little manicured hand, looking up at him with a sweet wicked smile. She tugged down the straps of the simple black dress she wore, and pushed down the lace bra as well, letting those magnificent tits bounce free. She sucked at him, working her mouth expertly on his cock, all the way down, then up to lave at the swollen head. She knew just how he liked it. He had taught her. She had Drake's cock all the way in the back of her throat, and she let it slide out with a delicious pop. He looked down at her with an appreciative smile,

"You wanna ride me? Come up here and bounce that pussy on me. C'mon, show that bitch how it's done." The bitch in question- WannaBeCarmenElectra- was busy watching an animated movie about penguins on the big screen TV and did not hear this, or seem to care.

"We land in an hour, and we have to go straight to the press junket. I don't have time to shower and get ready if you come all over me, and you know you will. I vote you come down my throat and I will swallow it up neatly like a good girl. No mess."

"I love how you think." He sighed, and felt her envelop his cock in her mouth again, this time sucking hard and serious, which is what would get him off in a matter of seconds.

She knew how to do that flicker thing with her tongue just under the head, and how to cradle his balls in her hand as she worked him, and just at the final second, she knew to carefully scrape her teeth along his shaft. She did all this and he came, shooting a thick, creamy load right down her throat. As promised, she swallowed every drop. She didn't let him go at all. She milked his cock dry, and when he had not a drop of semen left in his body, she got up to wet a cloth from the bar and kneel down again to gently clean him up. He would never admit it out loud to her, because he felt it made him kind of a wuss, but this was his favorite part. She always did this for him, the clean up. She did it with care, as if his cock and balls were precious jewels. She always licked away any stray cum with her tongue, then massaged him clean with a warm, wet towel that felt like a huge tongue. Sometimes she did it as he lulled away to sleep. When he was all clean, she would kiss the head of his cock and go right back to whatever she was doing before the blow job started- usually working. Claudia was not only a fantastic fuck, but she was also the best assistant he had ever had.

Today, before the mind blowing blow job, she had been quietly reviewing script notes for director Ravi Khan's action sci-fi flick "Modern World." Drake had been offered the lead, and he would probably take it, if his $15 million price tag was met. He might even come down on the price tag a bit if Khan agreed to cast the right people around him. Rather presumptuously, he had instructed Claudia to draft a letter to Khan, stating that he would take the role, with the price tag, and that he strongly suggested the Ukranian actress Mila Rostov for the love interest. Drake's penis tried to remind him of what he thought of tens, but Mila Rostov was the hottest thing out there, and even if he didn't nail her, nailing her on screen would boost his stock in the business. Claudia went back to studying the script, looking for anything that would need to be changed to suit Drake and Drake's on screen style. Drake watched her go into the bathroom and wash her mouth out with Listerine before she went back to work, and he smiled. Best personal assistant ever.

Drake hadn't always been this ravenously horny. He had always had a great appetite for sex, but he usually managed to keep it in his pants (not always, but usually) while he was married. When he had been married, the ten inch cock he had become infamous for sporting after an ex-girlfriend leaked photos of his dick to TMZ, had been mostly reserved for his wife of seven years, Adriana Hollister. His wife had been an aspiring model when he met her, and his love of beautiful faces overwhelmed his brain. She had been a gold digger. She had faked a pregnancy to try to get Drake to marry her, and then dramatically faked a miscarriage. Drake had known she was crazy, but his family was pressuring him to settle down, find a wife, start a family. Against his better judgement, he married her. He thought for a while that he did, in fact, love her. He truly believed that in some strange way, she loved him too. She might have, but she loved money and coke even more. The cocaine became a serious problem and her three stints in rehab were half assed. She was high every time, the day she got out.

She posed for Sports Illustrated once and never really got past that. That had been her one and only break. There were simply too many gorgeous women and Adriana tended to be the girl that showed up loaded. She was not given many more chances. Their marriage began to fail. She started fucking other people. Drake did the same. She blew $25,000 a pop on shopping sprees on a regular basis. He didn't say anything about it, until she bought one of her lovers a Mercedes with his money. That was the end of it. She was bleeding him dry, financially and emotionally. They had stuck it out for seven miserable years. He wanted his life back.

The divorce process had been fast, but painful. She got half. He still had a lot. After his six year run on the hit medical drama "Chicago Rescue" playing the complicated Dr. Robert Fischer, he had three Emmys, a Golden Globe and a cool million dollars per episode in the last two seasons that ensured he wasn't going broke any time soon. He had done the show before he had been married and Adriana had not gotten a penny of that stash. The show was being rebooted and Drake had made several guest appearances with the new cast, and even, for the sake of nostalgia, considered playing out a full season, for the right amount of money, of course. Claudia thought this was a bad idea, since Chicago Rescue was on in the same time slot as "House" and the characters were quite similar. People would draw comparisons constantly between his Dr. Robert Fischer and Hugh Laurie's Dr. Gregory House. It would be annoying, and there was no need to go back to TV unless you're broke, Claudia had said. That seemed like good advice.

After the divorce two years ago, Drake had become ravenous for fucking. He had to have it, not just once, but several times a day. A girlfriend was out of the question. He had just gotten his life back in order. No need to complicate things with relationships he had no time for. Picking up girls for casual sex when you are a celebrity can lead to scary shit; women showing up on your doorstep claiming they had your baby nine months later (twice and paternity tests proved otherwise), stalkers (one had broke into his house and left a bloody pig's heart with nails in it), and gold diggers who wouldn't let go. That left hiring the high priced professionals who were admittedly fun, but risky if he got caught. Drake had no interest in Charlie Sheening his way through the tabloids. There were still occasionally the pros, and occasionally the casual sex with this or that actress or model, but for the most part, Drake kept his cock to a handful of select regulars; women he knew well and trusted. Claudia had been a godsend with her insatiable sexual appetite and her eagerness to please. When Claudia was not around, there was Caitlin, the hot shot film producer's daughter who went to UCLA and hung around Drake's pool to smoke pot and fuck away from Daddy's watchful eye. There was Grace, who was tall and blond and elegant and his age, who ran a swanky art gallery in Beverly Hills, and there was Gina, who used to be his agent before she gave up her career to get married and have twins and bake muffins. She was married but the husband didn't mind that she fucked a movie star, as long as he could watch every once in a while. The wild card was Pacia, the exotic Spanish actress whom he only saw two or three times a year but when he did, she brought along her sister, Gisela, who looked like a twin, and the two would fuck in front of him. It was sick, and he loved it.

He was thinking about just that when the voice of the pilot, Jeff, came over the speaker,

"Sir, we're going to be landing at London Heathrow in twenty minutes. We ask that all passengers put on their seat belts and prepare for landing. Thank you."

Claudia moved to the seat next to him and buckled in as she briefed him on what was to be expected at the press junket at the Ryall Hotel. After the press junket, there would be an interview with Virgin Radio, another with BBC2 and that night an appearance on Graham Norton. He would be on zero sleep, and a lot of caffeine.

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