Serving Jessica

Okay, I admit it – Jessica Simpson has always been one of my fantasy girls. I'm a little embarrassed by that, so it's definitely a guilty pleasure. I've also never indulged in celebrity fantasy stories, because they just don't pass my "realism test", but I finally gave in to my own secret desires and put this one on paper. So try to "suspend your disbelief" for a little bit, and treat this story as harmless fluff. If you're like me and think that Jessica is just sexy as hell, regardless of any other qualities, then you may just enjoy it.

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I couldn't believe my luck. When I switched my major to Entertainment Management, I knew that program included a co-op feature, and I was happy that I would get a chance to actually work in the business before I got my degree and was thrown into the "real world". But I had assumed that I would spend a semester at some mundane job, maybe working for a local talent agent or, at best, at a booking agency in a larger city. Imagine my surprise when I found out that the university had contacts all over New York and Hollywood, and that I had a chance to work for a couple of months in one of the centers of the entertainment world.

I got another surprise a couple months later when I saw the list of possible co-op assignments. Scanning down the page, I recognized a few agencies, etc., but what caught my eye was one entry about halfway down: "Personal Assistant - Jessica Simpson". The music industry in general was my preferred area, and being a "Personal Assistant" seemed like a chance to really see things from the inside. Plus, while I've never been a fan of Jessica's music, I've always thought she was smoldering hot. Just being around her would be incredibly exciting. I signed up immediately, and two months later was on a plane bound for Los Angeles.

When I got there, it turned out the job was just a little overstated. In reality, I was not to be Jessica's personal assistant, but the assistant to her personal manager, her good friend CaCee Cobb. Still, it wasn't a bad position, since CaCee pretty much ran everything in Jessica's life. Jessica was really "hands-off" and for the most part clueless about the business side of things. CaCee handled some of the everyday business functions and also managed the entire household, especially now that Jessica had separated from Nick. I was actually surprised that CaCee was there, since I had heard she left Jessica a while back, but it seems that she came back, at least temporarily, to help Jessica after the split. She was once again living in the house, and as it turned out, I was able to do the same – an extra little perk that would allow me to save money, experience things first hand and, I hoped, meet some other celebrities. I was very excited.

For the most part, I was just a "gopher", but I didn't mind since I was still surrounded by the entertainment business. Since the house was our office, everything was very casual, including the dress, which usually amounted to cutoffs and tees, or casual skirts and dresses. That was another interesting thing: the entire staff seemed to be female. I couldn't tell if this was by design or just coincidence, but in any case, it certainly made me feel comfortable coming in. On the other hand, because of my sexual preference, and since I had no current sexual outlet, it could also be a distraction. For example, during the first couple weeks, I often caught myself staring at the house secretary, Kelly, a cute little redhead whose full breasts and curvy body were a treat that was I just dying to sample. I had to watch myself so my hidden yearnings did not become obvious.

I really didn't see much of Jessica. She left everything to CaCee, with whom I spent a lot of time over those first couple weeks, learning the routine and adjusting to my role. I was really impressed with her. CaCee was very business-like, always on top of things and always in control. She was also very attractive. When I took the position, I had thought about how exciting it would be to be around Jessica all the time. I had always thought that she was one of those girls who just oozed of natural sexuality, and that feeling only grew with the little time I spent with her. On the other hand, CaCee was also attractive and very sexy in her own right. Like Jessica, she was blonde, but taller and not as voluptuous. Her personality was different too - strong, smart, and confident, which really appealed to me, and made her, in my eyes, even more attractive than Jessica, though not as overtly sexy.

Unfortunately, about two weeks into my stay, I screwed up pretty badly. CaCee asked me to bring Jessica's new car around. It was a very expensive little sports car, and the power surprised me. As I pulled it out of the garage, it suddenly surged forward and I lost control, driving into the concrete wall next to the drive. It really wasn't my fault, but the bottom line was some serious damage to the front left side of the car.

I went to CaCee in tears, apologizing profusely, and though she was sympathetic, this was Jessica's brand new car, her toy, her baby, and she wouldn't be pleased. CaCee warned me that Jessica was not very tolerant about these things and that, unfortunately, she may have to let me go. I was devastated.

CaCee talked to Jessica and from what I could tell, it didn't go so well, but she didn't say anything the rest of the day. The next morning, however, she called me into her office to talk about "my situation". A feeling of dread filled me as I stood there in front of her.

"Well, Jess is pretty pissed," she said. "Her first reaction was 'Just get rid of her.' But I'm still hoping we can work something out. I like you and you do good work." I thanked CaCee for her faith in me and held out hope that things would be okay. "Whatever I can do to make it up, I will," I pleaded. "I really want to stay."

CaCee was supportive, but she said that Jessica could be a real brat sometimes. Insurance would cover the cost, but she was really upset about her car, and CaCee had to find some way to appease her. She stood there staring off in space for a while, then looked at me, then off again. I could sense the gears working in her brain.

When she finally spoke, it was an odd change of topic. "You know, I saw you looking at Kelly the other day." She paused, her eyes searching mine, like she was waiting for some reaction. "She's a nice looking girl, isn't she?"

She caught me off guard, but I could tell there was something more to her line of conversation. I worried that she had noticed my real interest in Kelly, and my defenses immediately rose, but I responded simply, "Uh ... yeah, Kelly's a cute girl. Seems pretty sweet, too. I like her."

CaCee was eyeing me as I spoke. She seemed to be trying to interpret my response. Then, looking me straight in the eye, she continued, "Yeah, I could tell you like her. Actually, I think you like her a lot."

Now I was really worried. It was clear that CaCee had figured out that I was gay. I never thought my sexual orientation would be an issue, especially in the entertainment business, but I was already in trouble, on shaky ground. Maybe CaCee and Jessica were homophobes, or their "Christian values" caused them to look at lesbians as "sinners". Whatever it was, it didn't look good.

"Hey, look," I started. "I don't know what you're thinking, but..."

CaCee interrupted before I could finish. "Don't worry, Milene. I understand how you feel, and I'm perfectly cool with it. You like girls, right? It's okay, really."

I didn't say anything, just looked at her, but my silence answered her question quite clearly. "I have no problem at all with your 'interests', hon. I've been known to sample the 'soft side' myself on occasion. So you're not in trouble. In fact, this might help out with your other problem."

Now she had my attention. Anything that could help me stay on as a co-op was definitely of interest to me. "How so?" I asked.

"Well," she started, trying to choose her words properly, "I'm thinking maybe you can make up for your mistakes by providing some "extra services' ... like for another girl." She paused again to let her meaning sink in. "Does that sound interesting?"

Now my mind was racing, trying to take in this totally unexpected proposal. It seemed almost like blackmail, forcing me to do this in return for her leniency, but at the same time, it was wildly exciting! As I thought things over, I looked at CaCee there before me. She looked beautiful in her light sundress, which did nothing to hide the lovely shape of her body. I knew that doing her would be more pleasure than obligation. I was imagining myself on my knees before her when she seemed to read my mind and broke into my private thoughts...

"I'm not talking about me, hon," she said. "Though I am flattered." She smiled to make me feel better. "I'm talking about the lady who pays the bills ... Jessica."

Wow, this was a shock. "Jessica?", I asked. "Jessica's gay?"

"Of course, not, silly," she answered. "But lately she's been 'branching out'. After the whole Nick fiasco and a couple of messy, short-lived flings, Jessica got really down and kind of swore off men for a while. But she has these needs, you know?" I nodded my understanding. "So lately she's been trying the girl thing. It was my idea, actually - sexy, no-strings fun, mostly one-nighters, no drama. I told her how girls can really be better in a lot of ways: softer, longer lasting, more giving. And let me tell you, Jess seems to need a LOT of giving!" CaCee snickered at her own little joke. "Anyway, so far it's worked out pretty good for her, I think. The only problem I've had is finding the right girls, ones who are interested in this, but also discreet. Jess has no desire to become the next celebrity sex show."

Wow. This was definitely interesting, and I quickly told CaCee so, but I still had lots of questions. CaCee answered them all: This would have no impact on my other responsibilities, which thankfully, I would hold onto. These would be "extra duties", which would usually be at night, in Jessica's room, unless she was traveling and wanted to take me with her. I would be expected to be there whenever she wanted, to "service" her, with no additional compensation. And, to insure the discretion aspect, I'd have to sign a non-disclosure agreement, saying I would not reveal anything about the arrangement or my sessions with Jessica, with a hefty financial penalty if I broke it.

"Oh, and I like I said before," CaCee continued, "She does need a lot of attention. I guess she has pretty strong needs. I can tell you that a couple of times, I tried hiring high-class call girls, and they were in there a long, long time. The last one even told me not to call her again - she just couldn't eat that much pussy! Haaa!" CaCee really got a kick out of that comment. "That was almost a month ago, and Jess has been after me to find someone else. She's definitely 'in need'."

"Oh, and one more thing," she went on, "don't expect to get anything yourself. This is all about Jess, nothing more. She's the classic pillow princess, if you know what I mean. Just wanted to warn you. But the good news is... you do get to keep your job."

This was all so amazing to me, almost surreal. The idea that I was going to keep my position by making love to Jessica Simpson was just too incredible. Too incredible, but also too good to be true. I felt like I was winning on all counts. I told CaCee I was definitely in, and I hoped I could satisfy Jessica, though in my heart, I was sure I could. CaCee seemed happy. She said if this worked out, it would save her a lot of time and headaches.

Now CaCee was staring at me intently. "There's just one other thing," she said. "I need to make sure you're good enough." I didn't understand, but then she backed up to her desk and beckoned me toward her. As I reached her, she hiked up her dress and with a firm hand on the top of my head, lowered me to my knees before her. "Go ahead," she said looking intently into my eyes, "show me what you can do."

Ahhh, I understood now. This was the test, the "interview". Without hesitation, I reached for her panties, a lacy black wisp of fabric that looked sexy as hell against her pale, pink skin. With both hands, I pulled them down, over her thighs and calves. CaCee stepped daintily out of her underwear and leaned back against the desk, spreading her legs a little wider as she did. Her full, meaty lips were right in front of me. I wondered for a moment which way to go with her - slow and easy or down and dirty - but CaCee made the decision for me, reaching down to grab a handful of my hair and pulling my head up into the heat of her crotch. Suddenly my mouth was full of pussy, and my instincts just took over.

All the talk on the subject must have turned CaCee on, because she was already wet when I took my first lick, a deep, delving probe into the moist confines of her cunt. I explored inside her for a while, licking her walls, turning on the spigots of girljuice. CaCee's hand was still in my hair, grinding me into her insistently as she made earthy noises of satisfaction: "Unnghhh ... Ohhhh ... ahhhh ... Unnnghhhhh!!!!" She definitely seemed to be enjoying it.

By this time I was really turned on, too, by the whole situation. There I was, on my knees in the office, eating out this beautiful blonde who also happened to be my boss. I couldn't wait to make her come. I grabbed onto her hips, my fingertips reaching back to the silky roundness of her buttocks as I pulled her forward and dug deeper into her. "Unnnnnhhh ... " she muttered. "Ohhh ... my god! ... long tongue!" That made me really happy, but my satisfied smile was hidden in the depths of her musky folds. She loosened her grip a bit, giving me more room to work, and I took the opportunity to run my tongue up and down the length of her lips, sucking gently at various spots along the way. The hand on my head was trembling now, but when I moved up to kiss her clit, it tightened. She tensed up with pleasure, then shook even more urgently as she jammed me back against her. "Ohhhh! Yeah! ... do me there ... oh god ... right there!!!"

She obviously wanted a quick release, and I knew just what to do. Licking lightly over the underside of her clit, I teased it with the flat of my tongue, shaking my head back and forth to accentuate the feelings in her little nub. The volume of CaCee's moans increased noticeably and I knew she was almost there. I took her clittie between my lips and sucked a bit while my tongue washed over its sensitive tip. That did it. CaCee's body tensed, her back arched a bit, and both hands dug painfully into my hair. There was a little scream, smothered in her throat, then another, then a long, drawn-out "ahh" that had several hitches in it as her hips twitched in tempo with her voice. It was a really good come.

Once she settled down, CaCee pulled me up for a deep sweet "thank you" kiss, followed by a sarcastic "Yeah, you'll do." Then she added, wiping a bit of her juice from my chin, "Maybe I should have kept you for myself."

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The rest of that day and the next were difficult for me. I had kept my job, so I had work to do, but of course, I couldn't concentrate. Jessica was busy the first day, so CaCee couldn't talk to her about me, but the next morning she told me that that she had talked to her, told her I was really into girls, and (with a wink) that I was "very, very good." She said that Jessica seemed excited and expected me in her room that night at 10:00. Knowing what I'd be doing that night, I was totally distracted, constantly thinking about sex. To make matters worse, I spent most of my time with CaCee, and every time I saw her, I saw how sexy she was and remembered how much fun I had going down on her. I was just completely horny all the time.

By the time I reached Jessica's room, I was more than ready. At 9:00, I was pacing the floor in my room, unable to concentrate on anything except my "job" for the night. By 9:30, I gave up and just went on to Jessica's room. Standing in the hall outside her door, I could hear the shower running inside. Then it stopped and in a few minutes, I heard a hair dryer, then silence, then the sound of soft footsteps, and finally silence again. I was still only 9:45, but I just couldn't wait any longer. I knocked quietly on the door and from within heard a pleasant and common "Yeah! Come on in."

The first thing I saw when I opened the door was Jessica's bed – a canopied California king piled wit more pillows than I'd ever seen before. And next to it, there she was, wearing a short terrycloth robe that confirmed she had just gotten out of the shower. "Hey!" she said brightly, "How ya doin'?"

"Ummmm ... Doing good," I responded. I was tongue tied, not really knowing what to say. I felt nervous and shy, both because she was so famous and because of what knew I was about to do. That feeling intensified a moment later when Jessica's robe suddenly dropped to the floor, revealing that incredible body that I had been thinking about all day. In profile, the lush curves of her breasts and her ass were outlined for just a second, before she jumped onto the bed like a playful little girl, her boobs bouncing lightly on her chest.

"So you like pussy, huh?" Jessica was grinning, biting her lower lip. I couldn't tell if she was embarrassed by her question or if she was suppressing a mocking giggle. In any case, her question set me back for a moment. I never expected her to be so direct, and my response was a lame "Uh, yeah." It didn't matter, though - she wasn't really paying attention, anyway.

I watched, enraptured, as she lay back in the huge pile of pillows, marvelously naked, arms and legs all stretched wide, her blonde hair spread out like a golden veil over the clean, white linen. She squirmed a little on the bed, trying to get comfortable, then settled in, her head lolling lazily to the side as she got ready for a long session of luxurious pleasure. She looked absolutely beautiful, a vision of sex, like some hedonistic queen, splaying herself open, exposing her private parts so her slave could service her. Almost subconsciously, her pelvis inched up slightly off the bed, subtly begging for attention, or perhaps offering up what she sensed I wanted. My god, her thighs were just lovely, perfectly proportioned to her body, creamy tan, shapely and smooth. And between them, topped by a small tuft of feather blonde hair, was nestled the most beautiful font of femininity I'd ever seen - a juicy, pink morsel just begging for an intimate touch.

Finally she spoke again. "Well I've got the pussy," she breathed, "I just hope you're good, 'cuz it's been way damn long! I'm really, really horny." With a devilish grin she continued, "You might be in there a while." Her eyes were steamy - bedroom eyes, I thought - and her hips had now begun a slow, rhythmic pumping, subtle but undeniable, adding even more sensuality to an already erotic scene. I could feel myself becoming more aroused by the second. "You can take you're clothes off if you want," she said indifferently, "or leave 'em on - whatever. But don't take long. ... I'm ... ready right now."

Jessica settled back farther into the pillows and seemed to just be waiting, not entirely patiently. She was oblivious to me, off in another world now, her eyes dreamy and half-closed, not even looking at me. She hadn't even called me by name. I thought back to CaCee's comment about the "pillow princess" and chuckled at how literally true that seemed right now. My train of thought was broken after a few seconds, however, when Jessica realized that I had yet to move toward her. Her eyes opened with a look of mild surprise, like she couldn't understand where I was. "Well come on, I said I'm ready," she said quietly. It was half a request, half a command.