Journal of an Agent Ch. 20

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Dean decides Angelina Jolie needs a little grooming.
7.9k words
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Part 18 of the 28 part series

Updated 10/23/2022
Created 05/22/2001
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Back on track now, hope to finish series by end of the year. Feedback and suggestions always welcome.

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Standard Disclaimer:

You must be 18 to read this story, be able to read erotica in your community, not be offended by the contents of it...blah blah, you know the rest.

This story may be distributed freely, for commercial or non-commercial use, but PLEASE leave my email/name on it! That's all I ask!

This is Part 20 of an ongoing series. Yes I know the celebs don't act like this in real life, but this is a fantasy after all.

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I sat across from Angelina Jolie in my office. Angelina was wearing a white "wife beater" t-shirt and a pair of tattered blue jeans as she stared at me with a sort of dissident gaze, absentmindedly flicking the ash from her cigarette onto the carpet of my just-cleaned carpets. I didn't want to bring up the issue of not being able to smoke in an office building in California, I had bigger fish to fry.

I rested my head on my hand as I sat in my chair across from her in my wooden desk. We had been sitting like this for about five minutes, ever since she had walked in, sat down and looked at me. She looked like a spoiled child, her over-puffed lips stuck almost in a permanent pout. With a sigh, I decided to break the ice.

"You know why you are here Angelina, because of the request of the United Nations," I said to her. Angelina just nodded - though she had been my client for the past three months (she had come to my firm when her husband Billy Bob also signed with us), I had hardly spoken to her. She was so hot right now that I really didn't even have to try and sell her, so any project that wanted her as the lead got faxed to her mansion. If she liked it, she took the script. Otherwise, I never saw it again.

But the reason she was here today was different. Since being named the UN Goodwill Ambassador in August, Angelina had moved from the silver screen to the world of politics - there was quiet murmuring and whispers of disapproval that someone who was known to be as promiscuous, openly sexual and a bad example for some kids with her vices, would be chosen as a "goodwill" ambassador. The more conservative countries had made enough of a stink about it that the UN had called my office and asked that I "work with Angelina to make her more presentable for the world". And while I thought that the whole position was just a figurehead, I figured that this kind of free, good publicity only comes along once in a great while, so I might as well make the most of it. I had brought Angelina in to ask her how she felt about an etiquette or manners class. Hence, the pouty expression.

"I know that we haven't exactly become chums since you joined the firm," I said, "But the UN holds some of the biggest political weight in the world, and politics eventually trickle down to Hollywood. That Oscar may be hot right now, but if you piss off the wrong people then you may find yourself back making movies like 'Hackers',"

"Fine. If you want me to stop smoking, I will. I'll get away from acting so sexually aggressive in public, even though it really is no big deal, and I'll quell those rumors about me and my brother by not appearing with him in public anymore. But I am NOT going to a fucking manners class," Angelina said, stubbing the cigarette out on the fabric armrest of the chair.

I winced a little, knowing how expensive that chair would be to get re-upholstered, but shifted my attention back to the problem at hand.

"Look Angelina, you don't have a choice here. As your agent and friend I will NOT let you squander away the chance for some incredible PR for helping the UN. Think about it on the trailers - 'Oscar Winner and Humanitarian Ambassador Angelina Jolie'. What could be better than that? It shows you are a great actress AND you care about people," I said, trying not to come off as sounding too crass. The truth was, without abiding by the UN's request, Angelina may become in effect blacklisted from Hollywood. This wasn't about any marquee display, it was about her career. Unfortunately I couldn't tell her all this or else she would think I was a nut.

"I'll think about it Dean, that's all I will say," Angelina said, getting up to go. "I've got lunch with Billy Bob right now, so I have to go. Give me a call later about it,"

I watched her go and went ahead and made the decision for her, calling up all the manners schools in Los Angeles and asking their recommendations on what to do with someone as notoriously wild as Angelina. I finally decided on a resort style manner school way out near San Pedro that was not only isolated but highly recommended by even the other companies competition.

I heard later that week from them that, after they placed a call to Angelina's house to confirm her arrival time, she had gotten into a vicious shouting match with the woman on the phone, but had eventually caved in and agreed to attend the classes. I breathed a sigh of relief and quietly mused at my desk about my new "title" - Dean Simonds, agent to the Ambassador. I liked the sound of that :)

But things didn't go exactly as I had planned - the school Angelina was attending, called Proper Woman Academy, said that Angelina had been asked to leave not even two weeks into the training. When pressed for details, the obviously shy woman on the other end of the phone made up some excuse about having to go and cut our conversation short. As I hung up the phone, I was puzzled as to what could have POSSIBLY caused a school known for it's commitment to "refining ladies" to kick Angelina out. I decided to hear it straight from the source, so I got Angelina to come in the next day.

Unlike before when she had been resentful and arrogant towards the idea of being taught anything (don't think this was just one of Angelina's traits...it happens in almost all of my clients, sadly), now she had an heir of a disenchanted child about her; that is, she acted like she KNEW that the manners classes were good for her but that she was too proud to admit to it.

Angelina took a seat in the same chair she had sat in a few weeks earlier and folded her arms across her chest, her breasts resting gently on the crooks of her arm. Angelina wore just a light gray men's work shirt underneath a thick and heavy leather jacket, and a pair of black form fitting dress pants, of which the outfit blurred and obscured her renowned curves and numerous tattoos.

"So what happened? How did you get kicked out?" I asked her, my hands folded on the desk in front of me. I felt like I was her father, lecturing her about doing poorly in school. "Angelina, could you answer my question please?" I asked again.

Rather than responding, she just looked around my office. After a few seconds, she got up from the chair and began walking around the room, oblivious to me completely. I was now getting a little angry.

"Look Angelina, you may be a big star but when you are in this office, you are just another client and you need to answer my questions. WHY did you get kicked out of that school" I asked, now standing up from the chair, for what reason I don't know (perhaps my anger made me rise).

Angelina continued walking around the room slowly, running her long fingers over anything that caught her eye. I saw she was paying very close attention to my wall of photos, most of which had been of my father with various stars from the 60s to the late 90s. She spoke at last though.

"I got caught fucking Billy Bob on school grounds," Angelina said nonchalantly, her back turned to me.

I was almost dumbfounded, although I don't why I was - I should have seen this coming. I tried to think of what to say in response to that.

"Well...I'm sure that, now that I know that, if I call the CEO of the school, Mrs...uh, Robbins, we can sort this thing out," I said, confident in my solving of the problem.

"I don't know...we were doing the fucking on top of her desk," Angelina said, this time turning to look at me in the eyes as she spoke from across the room. My throat had gone dry as the image of Angelina bent over a desk not unlike the one in front of me, getting slammed hard from behind, filled my thoughts.

"Oh," I said dryly. "Well, what did you do when she walked in?" I asked.

"She joined us. You know, for a woman who spends so much time around sexually aggressive women, you'd think she would know how to eat pussy better!" Angelina said exasperatedly, like having sex in the middle of some strange woman's office on your agent's dime was an every day occurrence. Of course, with Angelina, I never knew.

She was now standing in front of the desk now, her palms flat on the desktop and her narrow ass arched high behind her. Her long brown hair, in a ponytail when she walked in, now hung over her left shoulder softly as she stared at me.

That added bit of information had made it even harder for me to concentrate on the situation. I suddenly realized that I had a quite large erection and that Angelina was probably staring right at it. Embarrassed a little, I sat back down in my chair.

"Ok Angelina but," I started to say, but was cut off. Angelina now sat on the desk halfway, her gorgeous ass half on and half off the desk, her long nails clinking on the laminated wood top of the desk as she sat in thought.

"Look Dean, let's be honest about some things right off the bat. You don't like me very much do you?" Angelina asked.

"Now Angelina, I didn't say that. I just thought..." I said before being cut off again.

"Let's keep these answers simple alright? Yes or no. I know how you agents like to go off on these long-winded speeches. So just answer me, yes or no" Angelina said.

"But.." I stammered, but Angelina had put a finger to her lips and motioned for me to follow her instructions. I felt like I was playing a game now with an adolescent child, but I knew in reality that if Angelina was anything besides an actress, it was that of a sexual huntress. I knew I had to tread lightly through these questions if I wanted to get anywhere.

"No, I don't, not really. But that's just your person-" I said, but Angelina shushed me. It suddenly dawned on me that Angelina and my eyes had been locked for I don't know how long, and that she was leaning closer to me.

"That's fine. I know not everyone in the world is going to like me, but in our case we need to work something out," Angelina said. "Now, even though you don't like me, do you find me attractive?"

"Yes," I blurted out, regretting that I was thinking with my head rather than the head with my BRAIN in it.

"Good. As do I with you. Now an even more important question: Would you fuck me?" Angelina asked. Her bee-stung lips were now just a few inches from mine as she leaned down on the desk. It suddenly hit me - I was being seduced. But to what end?

I hesitated for a moment before replying, trying to map out every scenario for where this was going. Choosing what I thought was a safe road, I answered:

"Well, yes I'd like to but the whole issue with your husband, Mr. Billy Bob Thornton seems to be a bit of a roadblock. Besides, you only fuck him right? That's what you've been telling all the magazines," I said, confident in my reply to the question.

Angelina began laughing at my question loudly, a rather throaty and deep laugh. She seemed to get a real kick out of something I said.

After calming down, but still giggling, she said: "Boy you really WERE wet under the ears when you took over this firm weren't you? That whole 'I only fuck Billy Bob' thing was an idea created by YOUR father one night while he was fucking the shit out of me in the back of that car you drive, that BMW whatever,"

"So then you don't just sleep with Billy Bob?" I asked, my confidence in keeping my relative monogamy with Natalie Portman now growing weaker every day.

"Oh, I do sleep with Billy Bob a lot. He's a great fuck, that's why I married him. But if you think someone like me is going to be satisfied with one man, you are horribly mistaken. That reputation I have in Hollywood didn't just appear out of thin air. Although I do think a lot of it came from that one producer who I wouldn't let cum in my pussy. What was his name again?" Angelina pondered wistfully. The absurdity of this conversation was increasing with every passing word.

"And Billy Bob knows about all this? He doesn't mind and actually takes part in it?" I asked.

"Oh yea. He loves watching me with another girl. And I get off on knowing he's there, waiting to fuck me when we get home after I'm done fucking a total stranger. But he REALLY loves it when I fuck another guy. We have this whole charade we put on, where he acts like the surprised husband who comes in and catches us. He gets all pissed off at the guy and threatens to shoot his balls off but then I 'magically' calm him down and Billy Bob joins in," Angelina said. "I don't know, it's some kind of power trip thing. But I have to admit that we put on a pretty fucking good show. Oscar caliber stuff for sure,"

"I find your sex life to be oh-so fascinating Angelina, but what does that have to do with you getting kicked out of that school and why you are now just a few inches away from me on my desk?" I asked, leaning back in my chair. My hands rested on the arm rests and were a little sweaty from the raw sexual tension and energy that seemed to emanate from Angelina's body. She was a sex kitten, without a doubt.

"Well, the school thing was just a misunderstanding. You can probably fix that - Billy had just brought me some lunch to eat since he had the day off and one things led to another," Angelina replied.

"You on the other hand," she said, taking my tie in her hand "are a different issue. I know we don't get along real well and in fact hardly see eye to eye on anything. But I think that for both of our sakes and our working relationship," she said, leaning so close I could feel her warm breath on my upper lip "you should fuck the living shit out of me,"

With a sudden movement, Angelina shot her hand down to my crotch, that had become incredibly hard in the past few minutes. Still, I was trying to come to grips with this relative insanity - I knew first hand that mixing sex with a working relationship (my psycho ex-assistant Julie) was NOT a good idea.

"So how about it Dean? I'll let you do whatever you want," she purred, her tongue dragging on the word "whatever".

"So if we fuck, that will make things better between us and we will get along. That's your brilliant idea?" I asked. I was incredibly turned on by this whole thing and getting more so by the minute as Angelina's hand began moving slowly up and down my shaft as she squeezed and fondled my balls through my pants. The idea had a very kinky allure to it, being able to compete (so to speak) for dominance by the sheer power of fucking.

Angelina didn't reply to my question, she just very, very, very slowly nodded her head, a sexy "come hither" smile on her face.

Leaning in to kiss me, we were interrupted by a buzz on the speaker phone: "Dean, you've got a call from Warner Brothers on line 3. You want me to take a message?"

"No Damon, I'll get it. Thanks," I replied, looking at Angelina.

"Who was that on the speaker phone? He sounded sexy," Angelina said, now sitting on the edge of the desk with her legs dangling in front of my crotch.

"That was Damon, my assistant," I replied.

Angelina connected the name with a face and her eyes lit up "Ooo, call him in here. Then we can really have some fun," she said.

"No. I have to take this phone call. I'll talk to you later about your...idea. Now, if you will excuse me," I said. Angelina looked a little hurt but I really did need to talk to Warner Brothers. They wanted a new show for Shannon Doherty now that she was off 'Charmed' and wanted me to try and work something out. I glanced at Angelina as she sat on the desk, looking pouty again.

I motioned for her to leave, but it was to no avail. She mouthed 'I'm not leaving till I get what I want'. I was getting a little angry as I tried to carry on a conversation with them.

"No, I agree completely. I think that if Shannon had complete creative control of the show, she wouldn't get into any more fights or trouble. Besides, it would give her something to do besides pick up trash on the freeway," I said jokingly. Angelina had hopped off the desk now but had dropped to her knees on the floor. With considerable strength, she parted my legs and went straight for the zipper on my slacks.

I tried to resist her and still not let on to the WB that my attention was not fully on what they were saying but Angelina had basically already won. She had darted a hand inside my zipper as soon as it was down and was fishing around for my cock, trying to pull it out from the zipper. I glanced down at her as I watched her struggle with the clasp and gave her an exasperated look as I undid the top button of my pants. If she was hell bent on giving me a blowjob, at least I could make sure she didn't rip my balls off in the process.

My pants sliding free, Angelina pulled my hard prick and dangled it in front of her mouth.

"Yummy...I always like appetizers before the main course," she said. And like a lightning bolt, her mouth engulfed my cock.

To say that it felt good inside of her mouth would be the most drastic understatement in history. There was something amazing inside Angelina's mouth and whether it was a natural ability, lots of experience or maybe even those puffy lips of hers, she knew how to give a blow job.

Her mouth warm and wet, like a sauna with suction, felt incredible around my cock. I had almost shot my load when she had wrapped her lips around me, but managed to control myself (a technique that I had been taught just a few weeks earlier by Lucy Liu and Zhang Ziyi) and delay orgasm. Angelina's lips bobbed up and down on my shaft, the skin moving in time with her lips and she sucked and licked greedily like a popsicle.

I suddenly realized that I hadn't said anything in the phone for at least 2 minutes, but was saved by the fact that they were still talking about what an idiot Aaron Spelling was. "Uh-huh," I said into the mouthpiece, trying to keep my breath from sounding too labored.

Angelina removed her mouth from my cock but lifted it up to lick it on the underside, mimicking something a porn star would do, as she ran her fingers over my balls, tickling and teasing them as they hung below my purple headed shaft. Angelina popped my meat back in her mouth and went back to work sucking me off. She had managed to work her way under the desk so that if anyone walked in, they wouldn't have the slightest idea what we were up to (although I think the heavy sweat on my brow would have been a dead giveaway).

I tried to focus my attention back to the phone. "Yes sir, go on. I think we are headed in the right direction," I gasped into the phone, still hoping I wasn't too obvious. My hands, which had been fidgeting on top of the desk and moving around to try and keep myself occupied, now acted on instinct and moved down, gripping Angelina's head in my palms and moving her head up and down on my crotch while I held the phone against my ear with my shoulder.

Angelina really knew how to give a blowjob, as every time her tongue would touch my sensitive cock, it felt like a spark of electricity shot from her mouth and onto my prick, charging it up and bringing about the most intense pleasure. She seemed to sense that I was close to cumming, so she began sucking hard on my prick, waiting for my load to come.

I felt my balls tense up and then explode my load in a torrential flood of semen, shooting it straight into her mouth and down her throat. I had to bite my lip to keep from groaning too loud into the phone while Warner Brothers talked. As I felt my orgasm subsiding, Angelina removed her mouth from my prick and licked a little droplet that sat perfectly on top of my head clean, leaving my prick still hard though. Angelina climbed out from under my desk and wiped her mouth with her little pinky, smearing the remaining cum onto her tongue.