11 comments/ 114822 views/ 18 favorites Serving Jessica By: Milene 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. =============================== 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." _________________________ 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. Serving Jessica I reacted swiftly, removing my clothes and climbing onto the bed, positioning myself at her feet, between her outstretched legs. Jessica stared at me there, closely watching my every move as I prepared to make love to her. I started simply, lifting her left foot and running my hands tenderly up and down the length of her outstretched leg, drawing a nice "Mmmmmm" from my famous mistress. Moving back to her foot, so delicate and pretty, I kissed and licked it in several places. I looked up to see her reaction and was pleased to see a big, contented smile on her face. She seemed to enjoy this kind of worship. Now my gaze was drawn down the length of her lovely leg, into her crotch, already gleaming with moisture. Above it, I could see that delicate patch of fine blonde hair, almost invisible in the dim light of the bedroom. I was a little surprised by that, since "bare" was the thing these days, but on her it looked very pretty and feminine. Raising her leg straight up in the air, I continued to kiss and lick at her foot and calf, at the same time inching toward that luscious treat in her crotch. When I reached her knee, I swirled my tongue against the sensitive area behind it and was rewarded with a breathy sigh. I let my hands move down to caress her thigh, then run lightly over the bottom swells of her ass. Jessica sighed again, which I took as my cue to move further still. I licked ever so lightly at the skin of Jessica's left thigh, just inches from her quivering quim. The scent of her arousal filled my head as I continued to tease her. She was trembling now, clearly in need of some satisfaction, which I was not about to give, not yet anyway. I pulled away, just a bit, to assess the physical affects I was having on her. I gazed at her cunt, so close now to my eyes and my lips. It looked incredible, so good, and so ready for attention that it was hard to ignore. Jessica was clearly aroused, and it showed in the overheated maw between her legs - beautiful, engorged petals of pink, meaty flesh, the inner lips protruding boldly and wetly through the over challenged sheath of the outer ones. Her cunt was a succulent, dew-covered delicacy, the most scrumptious-looking tidbit of flesh I'd seen in a long time. Nonetheless, I did ignore it, continuing to focus my lips on her inner thighs, while my fingertips traced delicate circles over the flat expanse of her mid-drift, barely making contact with her skin, trying to drive her crazy. It seemed to be working, based on the delightful whimpering noises she was making and the tremors I could feel coursing through her body. I had to smile to myself. If Jessica was at this point already, before I had even touched her pussy, then this was going to be a truly extraordinary sexual experience. I could tell she wanted it badly, needed it badly. I thanked the gods for her recent celibacy and thought of how I would drive her up the wall before making her shiver and shake with a totally satisfying orgasm. It made me shiver as well in anticipation. Wasting no more time, I started with a soft, delicate kiss right at the center of her open cleft, producing a wonderful little gasp from her. I pulled away slightly and licked all around the little crevice, teasing the surface of her lips, sometimes venturing inside a little to savor the warm nectar that was now flowing freely. Then I settled into a long series of easy tongue-strokes, licking her there like a contented puppy, with the tip of my tongue just barely inside her. I looked up from my place there, up over the flat expanse of her abdomen, past the perfect mounds of her breasts, to her face. Jessica was wide-eyed, intent, entranced by the sight of me slaving there between her sweet thighs. I caught her gaze and held it as I continued to work my tongue into her, telling her with my eyes how good she tasted, how wonderful her warm, sticky flesh felt as it grabbed at my invading tongue. Jessica kept her eyes on mine for a while, clearly excited that I was enjoying her so much, then closed her eyes as a huge smile filled her face. Her hips continued to move easily up and down in response to the wet little muscle exploring inside her. Mmmmmm," she murmured. "Yeah, I could get used to this. Soooo good. Nnnghh. I had no idea." Looking down at me working on her, she teased, with a little-girl smile, "You think you could just live in my closet and do this whenever I wanted it?" The thought of that - being at her beck and call for extended oral pleasure - sounded wonderful at that moment. Jessica's body was delicious, and being between her legs was absolutely divine. In my current state of arousal, her idea sounded like paradise, and I honestly think part of her thought it was a possibility, but my reality-checker was on-line and I knew it was just a crazy statement. Even if she were serious about keeping me around (though not in the closet!) and even if I were ready to give up the rest of my life for the taste of her pussy, it could never last. I knew that constantly being around this shallow, intellectually challenged woman would absolutely rot my brain. Still, her suggestion, mindless as it was, further inflamed my desire, and I was even more determined to give her the best head she'd ever had. My licking became more intense now, stronger strokes all over her genital area. I traveled up to the base of her clit, lapping firmly at the underside of her inflamed button, feeling her rise up and shimmy against me as I did it. I thrust my tongue way up inside her, as deep as it would go, worming around, enjoying the delicious heat that surrounded it, then swirled around the edges of her hole and back up to her engorged clittie. From the sounds and motions of her body, I knew Jessica was enjoying my attention, but surprisingly, after pleasuring her for a good twenty minutes, she still seemed far from a climax. I remembered CaCee's comments about the hookers and wondered if I had, in fact, taken on a challenge I couldn't fulfill. Surely I could satisfy this woman, couldn't I? I tried not to be discouraged and hoped it was just a matter of time before she exploded into the orgasm we both wanted. At last, I decided to stop worrying and just go with the flow. As Jessica's rear end rose slightly off the bed, I reached under her to cup her creamy, soft buns in both hands, then closed my eyes and gobbled her up, concentrating totally on my own enjoyment of her body. I was feverishly eating her, lost in my own reverie, when I felt a soft touch on my right hand, which was still lifting her sweet bottom up to my mouth. I let her down gently as her delicate fingers gripped my wrist and pulled my hand up to her lips, slipping my middle and index fingers into her mouth. The silky heat of Jessica's tongue applied a generous coat of saliva to their full length, sending a tingle up my spine and a new flood of moisture between my legs. The act was intensely erotic, and at first I thought she was just playing, but then she raised her hips again and directed my arm downward, into the hot crevice of her ass, positioning my well-lubricated digit directly at her anus. "Nnnghhhhh, there," she groaned, "put it in there!" Delighted with her direction, I continued lapping at her sweet folds as I pressed the tip of my middle finger into the clenching heat of her sphincter. "Ohhhhh mmmmmm, fuck... more," she murmured as I pushed deeper into her, up to the first knuckle, adding a gentle shimmy to my hand as I did so. Encouraged and excited, I looked up at her and studied her features while I continued to extract the pleasure from her lovely body. Jessica's tongue snaked lustily around her own quivering lips and our gazes locked together as she watched me, eagerly anticipating the next step. Suddenly her eyes opened wide and a wonderful little-girl squeal escaped her lips as she felt the entire length of my finger go up her butt. Her hips came high off the bed and shook with sensation as her anal channel clutched franticly at my invading digit. A huge grimace-smile crossed her face, her pelvis jerked hard in a single spasm of pleasure, and she hissed a long, fervent "Yeessssssssss" before her head dropped back into the pillows. I left my finger right there, holding firm, then drilled even deeper into her, drawing another pleasurable "unnnnggghh!" from above me. My god, it was so hot in there! As I reveled in the warm grip of her most private place around my little explorer, my tongue delved far into her other hole, working frantically to slurp up the juices that were now running generously down my chin. At that point I was very aroused and really went to work eating her out. My tongue worked eagerly over the edges of her lips and then deep inside her, where her sweet cream flowed in abundance. I pulled a little glob into my mouth and took it down, thinking to myself, I'm drinking Jessica Simpson juice! I squeezed my thighs together, got a little jolt, and licked some more, swirling my tongue all around inside the delicious heat of her cunt. I continue to work my finger in and out of her asshole, feeling the contractions of her little muscle ring as her excitement grew. Her eyes were closed now and her legs spread wide, almost completely out, and she was in another world, moaning loudly, a deep, rhythmic growl that switched to a high-pitched shriek when I washed over her clit or jammed my finger deep into her bottom. Her baby-fine pussy hair tickled my nose as I took her open cunt in my mouth and sucked. The warm, delicate flesh slid into my mouth, rushing against my tongue, bathing it with another thick coat of fluid. Looking up, I could see Jessica straining for her orgasm. Her head tilted back, her mouth open and slack, her back arched up, and her firm tits pointed upward, as her arms reached out to feverishly grip the bed sheets. Sensing she was close, I shimmied my head back and forth and hummed a low tone over her clit. At the same time, I eased a second finger into her rear and wriggled them both all the way up her ass, finally setting her off. Guttural, animal sounds filled the room, punctuated with a series of "Yeahs" and rapid-fire "oh fuck oh fuck oh fuck FUCKKKKKK!" Jessica's whole body jerked hard several times, about two seconds apart, her hips jutting up at me as her rear hole clutched frantically at my fingers and even more juice poured into my mouth. I licked it up and kept going, reaching up with my other hand to fondle her magnificent breasts, tweaking her nipples as she continued to spasm, keeping her floating in that oblivion of passion until she came again, and then again, before I let her down, licking softly at her folds until I felt her relax completely. I let my fingers slip out of her bottom, but she hardly seemed to notice. "Ohhhh ... sweet Jesus," she moaned. "Holy fuck ... oh damn ... ohhhhhh ... good." She was babbling, completely overcome by the sensation of her orgasms. Her hips still moved easily up and down, like she was remembering the feeling of my tongue there inside her. Finally she looked down at me, her eyes barely open. Still she said nothing, but she seemed amazed at the feelings I had just produced in her body. I just looked back at her, quite proud of how I had satisfied her. Then finally I said smugly, "I think you liked that," and she just smiled in return. I let her relax for a bit while I simply admired her body. My god, she looked incredible lying there. Her breasts now especially caught my eye, two magnificent mounds of softness, spread out on her chest, topped by the pinkish-tan circles of her nipples, their perky tips thrusting upward, clear indicators of her continuing arousal. I've always been fascinated by large, well-shaped breasts, I guess because I'm small on top myself, and Jessica's were just beautiful. Finally, I could hold back no more and had to ask for what I wanted. "Can I suck these for you? " I asked hesitantly, indicating her breasts. "They look like they could use some attention." "Oh yeah, sure!" she sighed, apparently thrilled that I found them so attractive, "help yourself!" She thrust her chest out a bit for emphasis. I started with my hands, taking one luscious globe in each, savoring the warm flesh as it overflowed their capacity. Then I leaned in and let myself enjoy them completely, brushing my cheeks lightly over the silky surface, letting the rubbery little nubs run gently under my open lips. Then I opened my mouth wide and took in her left nipple, eagerly suckling her like a hungry child. My tongue ran excitedly over the rough-soft surface, feeling the tiny bumps all around the center. We were both moaning now as I sucked her harder, at the same time tickling her tip with quick little strokes. I kept that up for a while, then moved to her right one, giving it the same treatment while my hand continued to stimulate its partner. I could tell Jessica was enjoying this, but now her body started to writhe and I knew it was time to move downward. I started slowly, reluctantly leaving her precious tits, traveling down over her ribcage to the flat expanse of her abdomen. There I licked in tiny circles over the surface, feeling the response as I teased her unmercifully, running my tongue into the tiny crater of her navel. Finally I reached lower, placing delicate kisses into the hollows of her hipbones, until the main course was there in front of me. Her pussy looked as yummy as ever, all pink and moist. I let my tongue wander up and down it, still going excruciatingly slow, feeling her straining upward to catch it. She was open wide now, and I licked all around the sensitive edges, up one side and down the other, ending in a erotic swirl around the circle of her anus. That brought an extra little quiver and squeal from Jessica. "Oh yeah," she breathed, "I like that. ... more ... ohhh, more." I did give her more, happily licking over her anal ring as she uttered a long, heartfelt "Mmmmmmmmmmm." until finally I felt her hand on my head, gently pushing me away. "Wait a sec," she muttered, and with that she flipped over onto her stomach, pulling two of the pillows under her hips to raise her luscious butt farther off the bed. Then she reached back with one hand to pull her left cheek to the side, lewdly exposing the spot where she wanted my full attention. "Okay, you can really do it now," she sighed. "come on." She arched her back slightly as her sweet bottom reached higher, her head pulled back to almost face the ceiling. When I failed to act immediately, she looked back over her shoulder, wrinkled her nose cutely, and drawled in a tone both sweet and nasty, "Mmmmm, go ahead, babe... kiss my ass!" That sounded unbelievable hot, and I did just as I was told, gently spreading her cheeks with my palms and bending forward to place a light, tender kiss right at the center of Jessica's lovely little butt hole. That drew a cute little laugh from her. Then I licked wetly all over it, hearing a soft "Ahhhhh" each time I did it. I put the tip of my tongue at the very center of her little tan ring, pushed slightly, and felt Jessica tremble. Her hole felt hot, and the muscle was firm but yielding. I knew I could get inside if I wanted to. Each time my tongue tip grazed directly over her hole, Jessica flinched and uttered another delightful "Oooh" or "Ahhhh." "Oh god.... I love that," she moaned, rolling her hips to emphasize her words. Her southern accent was becoming more pronounced as she slipped into sexual delirium. "Oh yeah ... eat my aaass" she drawled. "Mmmmmmmmmm." I pulled back for a second, and Jessica's head immediately swiveled to look at me. There was a look of near panic in her eyes, as if she were frightened I would stop what I was doing. No way. I had simply paused to take in the whole situation. I couldn't believe it - I was eating Jessica Simpson's ass! I quickly put my tongue back on her asshole. I began to push, slowly but firmly. I felt that lovely ring of muscle give way just a bit and the very tip of my tongue slipped inside, her asshole clenching warmly around the tip. I moved my tongue as sensuously as I could, making it squirm inside her anal ring. "Unnnghh yeah. ... Oh god, yeah...." she moaned, almost pleading now for more pleasure. "Oh fuck, mmmmm ... Yeah ... oh god, get up there ... up my ass!" She reached back and pushed my head deeper into her crack, making sure I stayed right there, but it wasn't necessary. I had my face buried in Jessica's butt, and there was no other place I wanted to be at that moment. I licked over her anal area, repeatedly easing my tongue against her little crater, testing it, until I finally felt her hole relax, opening just a little more. Then, using both hands to spread her perfect buns, I tightened my mouth muscle and pushed forward. I felt her shudder with the pleasure, heard a barely audible "Oh, Jesus", and then a long, pathetic groan that grew in intensity until finally my mouth was wide open against her opening, my face completely buried in the heat between her cheeks. Jessica quivered and cried at the exquisite feeling in her backside, and her little muscle clenched at the root of my tongue. I realized then that the whole thing was now up inside her, all the way up her butt, and I became so wildly stimulated that I couldn't resist touching myself. That single touch, together with the awareness of what I was doing, was enough to do me in. Suddenly I was in the throes of an intense orgasm, twitching and moaning as I struggled to keep my tongue buried deep in the delicious heat of Jessica's ass. As I came back down, I looked up to see Jessica staring wide-eyed over her shoulder, apparently incredulous that I had become that excited by her ass. She gave me a quick, questioning look, and then, as she realized I was going to continue, her eyes closed and her head settled back onto the pillow, blissful and content. Jessica's beautifully round bottom was still in front of me, still raised high atop the pillows, looking even better than I ever imagined it would. As my eyes were glued on her butt crack her hand once again reached back to nudge one cheek aside - a not-so-subtle hint that her delicate brown eye needed more attention. Gathering myself, I leaned forward once more, placing my lips firmly around her hole. I kissed it passionately several times, licking wetly all around the rim and tickling at the very center while she quietly moaned in satisfaction. At some point Jessica's own hand had moved between her legs, and her palm rubbing over her clittie while two fingers plunged deeply into her depths. Her fingers and my mouth worked in tandem, and we continued that way for several minutes, until she returned to the groaning, trembling state she had been in before my own ill-timed orgasm. Then, as my tongue eased into her again, I added a gentle suction, pulling the firm ring of her asshole into my mouth. I wormed my tongue inside and softly sucked on her. Jessica gave a little squeal and then she was over the edge, emitting a long, drawn-out series of grunts as she bucked her hips back at me. She buried her face in the pillow and worked her fingers furiously over her pussy as the waves of pleasure drove through her. Her muffled whimpers and squeals drove me wild as I groveled shamelessly behind her, twisting and squirming my tongue, going deep into her asshole again as we both rode out her orgasm. Even after she came, I kept my face in her luscious ass for a while, licking a little, but mostly just enjoying the feel of her silky cheeks, the musky heat surrounding my face. Finally I eased out of her and she relaxed, dropping her pelvis back onto the bed, a dreamy, contented look still on her face. She looked back at me from her pillow. "Da-yam," she breathed, her drawl more obvious than ever, "you really like ass, don't you? I can't believe how good you did that. Felt so nice. And you got off on it! Damn, what a rush!" Serving Jessica I was a little embarrassed by my own wantonness, but I couldn't deny it. "I do love your ass,' I said, letting my hand roam over the smooth expanse of her bottom. "It's so beautiful. I really did enjoy that." "Mmmmmm," she sighed. "Some girls won't do that, you know. Not even the hookers." She laughed softly, then added, her face just lighting up, "I think I like you!" We lay there for a while like that, Jessica recovering, me once again admiring her body while I waited for the next act. Jessica was on her back again, propped up as before on her mound of pillows. Her fingers ran lazily between her legs, brushing lightly over her lips, occasionally teasing herself with a brief circling of her clitoris. "You can do me again now," she said at last. "I'm ready again." She smiled as she said it, like she was doing me a favor, as if she were offering me another drink or a sweet snack. The idea that she might actually ask me for this never entered her mind. She just expected it. I stared at her for a moment, still somewhat astonished by her attitude. She was totally self-absorbed, and there was nothing on her mind, nothing in her world except what Jessica wanted. Finally noticing the look of surprise on my face, she reacted a little defensively. "Told ya I was horny!" she drawled, wrinkling her nose petulantly. She giggled and lewdly opened her legs."Come onnnnn," she whined. "Don't ya want it?" She reached down with both hands to spread herself wide open, revealing the delicious pink flesh inside, hoping to lure me back into her. My reaction was visceral - an uncontrollable shudder of lust at the sight of her steaming pleasure pit. Jessica's lower lip extended in an exaggerated pout as she continued her little-girl tease. "Look, I'm allll WET again!" Indeed, she was quite wet again. I could see a small pool of moisture glistening in the bright pink bowl between her cuntlips. She ran her index finger lightly over the inside and shivered exquisitely from the sensations, then used the same digit to beckon me back to her, smiling her best flirty smile. The girl was delightfully insatiable, and she knew she had me. Even if I wanted to stop, there was no way I could resist at that point. With a feeble, barely audible "Yeah, okay," I started toward her. Jessica's deep brown eyes lit up as she watched me slip back between her lovely legs and knew for sure that she was going to get some more. There was no need for preliminaries this time, so I moved in immediately for a soft, sensuous kiss right on her needy hole. I felt her juices ooze lightly over my lips in response. I heard a soft gasp and sigh above me, 'Shsssssss ... ahhhhhhhh ... yeahhhhh," and Jessica's butt cheeks flexed slightly, an involuntary reaction that raised her hips and cunnie up just a bit, eagerly reaching for more pleasure from my mouth. Her pelvis returned to that wonderful rolling movement that I'd seen the first time, feeding me her sex with a delicious, primitive rhythm. I couldn't believe how much she wanted. By this time my jaw was aching from eating her so long, but I knew what was expected, and I wanted more myself, so I went right back to work on her. She enjoyed my tongue for another hour before she was satisfied and sent me back to my room, the taste of her still lingering on my palate. By my count, she had come at least five times, and perhaps as many as eight. It was amazing. After that first night, I settled into a clear routine with Jessica. She wanted me in her room – in her bed – almost every weeknight, except for those few when she was busy with other things. Weekends were usually off, since she generally had other engagements to attend. During the week, ten o'clock seemed to be the time, and I was usually there for a couple of hours, pleasuring her completely until she was ready to sleep. The girl was simply obsessed with sex. It was like she wanted to see just how many times she could come in one setting. And as CaCee had predicted, there was never any reciprocation, just me doing her, though as time went on, we did add some heavy make-out sessions to the routine. We were both naked, of course, and the feel her body rubbing against mine as we kissed was intensely erotic. Sometimes she let me clutch her thigh between mine, and I could usually come at least once just from that. She really was incredibly sexy, and playing with her, licking and caressing her incredible body, making her come over and over, was extremely exciting. One day, about three weeks after the start my nightly "Jessica sessions", CaCee asked me to step into her office. As I did, she closed the door behind me, which immediately raised my concerns. Was something wrong? Was I in trouble again? "Is something wrong?" I asked hesitantly. CaCee seems startled. "Huh? Wrong? ... uh ... oh, no, not at all. Everything's fine. I just wanted to talk to you about something." She seemed distracted or confused, like she didn't know where to start. Finally she appeared to settle on her approach and she continued. "You know, Milene, Jessica seems to be really happy with your 'performance'." I noticed a little smirk at her use of the word. We both knew she wasn't talking about my regular job. I told her that I was glad Jessica was pleased, and that I was quite happy with the situation, too. "Yeah, I kind of got that idea," she responded, again with that little smirk, like we were sharing an inside joke. "The fact is," she continued, "I happened to be walking to my room last night while you were in with Jess. The door doesn't muffle the sound much, you know." She paused for effect, then continued, "It sounded very ... uh ... interesting." I could feel myself blushing. Jessica had been extraordinarily passionate the night before, even louder and more vocal than usual. If CaCee was outside the door at the right times, she would have heard quite a show. She was eyeing me now, gauging my reaction as she continued, "It could tell that Jess was having a really, really good time. Made me think back to that day a few weeks ago..." I could see where this was going now, and I didn't need any more hints. Without being asked, I dropped to my knees, urging her back against the desk as I had that other day, reaching up for her belt buckle. "Damn," she said, "you are an eager one, aren't you?" She seemed amused at how "easy" I was. Then she continued, "Not here. This time, let's make it different, more relaxed. Over there." She gestured with her head toward the loveseat that sat in the corner of her office. We moved to the loveseat and CaCee undid her belt and started easing her cutoffs down over her hips. I quickly moved to help her, pulling them down and off, revealing the lacy white thong that she wore beneath them. She was right, I was eager. Although Jessica had been the focus of my fantasies, and I enjoyed all my sessions with her, I had been thinking about CaCee ever since she'd given me my little "audition". In her own way, CaCee was every bit as sexy as Jessica, and her strong personality was just the type that always turned me on. My hands were trembling as I slipped her flimsy panties down over her thighs. I couldn't wait to please her again. CaCee eased down onto the loveseat and opened hr legs. I quickly knelt between them, caressing the insides of her thighs as she whispered "Oh yes... that's what I need." Her eyes closed and she lay back, content to get the same kind of treatment I had given Jessica the night before. Of course, we didn't have time for all that, but I gave her the best I could, kissing up and down the entire surface of her legs until she was beside herself with passion, then finishing her off with a wild bout of oral love, thrusting my tongue way up inside her, the way I knew she liked it, before licking her to completion. She came beautifully, using a throw pillow to muffle her cries of ecstasy as she thrashed about on the loveseat. I cleaned her up with my tongue and then she dismissed me, but I knew I'd be back before long. From that point on, things got even more interesting. Of course I continued my nightly trysts in Jessica's room, but in addition, several times a week, CaCee would call me into her office. She would immediately lock the door and I would know what to do. I'd go down on her for a half hour or so, always bringing her to climax, often more than once. Usually she would simply raise her skirt or lower her pants like she had the first couple times, but occasionally we'd have more times and we'd both strip naked, which definitely added to my own enjoyment. CaCee seemed especially interested in what I did with Jessica, always asking for details and often wanting me to do the same things for her. And once, saying she wanted to "try it", CaCee even went down on me. She did a pretty good job for a relative novice, and I actually got off from it. Just the fact that she wanted to do it was very exciting. But there was more to it than that. CaCee was indeed a dominant personality, and it came out more and more as our sexual relationship grew. In addition to our sessions in her office, CaCee began to "loan me out". She seemed to get a special thrill from offering my services to other women, enjoying the control she now had over me, though not in a mean or nasty way. It started with the girl who worked for the courier service, a cute little brunette who eagerly accepted CaCee's offer of a "good time" as an extra tip. I ate her out in CaCee's office while she watched, an act that seemed to add something for both of them. The girl came really hard, and after she left, I spent another half hour satisfying CaCee's needs. A week later, I did the same thing for the woman who cleaned the pool, an athletic Latino woman in her late twenties. She wouldn't let CaCee watch, but afterwards, I gave her a full accounting, followed by some long-lasting "lip service" to make up for what she had missed. And there were others, whenever CaCee saw an opportunity and sensed that the women in question would be open to some extra fun. She quickly hooked me up with Kelly, who turned out to be just as sexy as I had imagined, a veritable wonderland of pink and white femininity, and completely into girls as well. CaCee arranged for some free time in Kelly's schedule (in return for my full account of our lovemaking), and we got together regularly during the day, and some nights as well, when Jessica was away, spending long hours thoroughly pleasuring each other. There was also a woman from UPS – I don't know how all these gay and bi women ended up at Jessica's house - and then this darling Asian girl, Japanese, I think, whom I swear CaCee just picked up somewhere. I never saw any indication of a business relationship; she just showed up one afternoon and I did her while CaCee watched. The most extreme, however, was when CaCee gave me, without asking of course, to a record company executive. I don't know what CaCee got in return, if anything, but she told this woman I was hers for the whole weekend. Not that I really minded. She was in her late thirties, maybe older, but quite pretty, in good shape, and, as I soon discovered, a very talented lover. I've always found "older women" attractive, and the things we did were just divine. She was so appreciative of my attention - I can still hear her sweet murmurs of "baby" and "sweetheart" as I gave her a long and tender licking, culminating in a rather subdued but nonetheless exhilarating series of orgasms. She expertly returned the favor, introducing me as well to the pleasures of her strap-on. The contrasting feel of her soft body rubbing against me and that hard thing driving inside me was new and absolutely wonderful. And of course through all this, my nights with Jessica continued. I really thought that over time her desires would decrease or the novelty would wear off, but that wasn't the case at all. Four or five nights a week, I'd be down on her, with Jessica invariably experiencing multiple, gut-wrenching orgasms. She still was the pillow princess, but I could tell she appreciated what I did for her. I'm not sure she even knew about everything else I was doing, but I'm sure she didn't care, as long as she got hers. In any case, between her and all the others, it was just unbelievable. I'd never eaten so much pussy in my life. I guess I was essentially the house whore, but I absolutely loved it. Of course, all good things come to an end, and such was the case with my little dream job. After two months, my co-op term was up, and it was time to say goodbye to Jessica, CaCee, and all the others. It had obviously been much different than I expected, but I had actually learned some things about the industry, in between all the hot sex. Luckily, I packed early, because that last day was just crazy. Just before lunch CaCee pulled me into her office for one last dose of the "Milene treatment", as she called it. Later that day, Kelly and I snuck off to the cabana, where we spent a long time sixty-nining each other to a blissful stupor. And then I spent the entire night with Jessica, as she kept me awake and busy into the early morning hours. When I left the next day, she gave me a big hug and told me how much she'd miss me, wiggling her tongue obscenely to emphasize her point. It was a little crude, but sweet nonetheless, and I knew I really would miss her, too. Both she and CaCee took my number and told me that they would call if they were ever in my area. I begged them to keep that promise, as I imagined an amazing scene where I would do both of them together.