This is one in a series of stories based on the premise of selling myself as a call girl catering to rich and famous women, managed by CaCee Cobb, Jessica Simpson's former personal assistant. The premise may be a little shaky, but it's a fun concept and it reflects a real fantasy of mine.
NOTE: This is a work of complete fiction and has no reation to the real lives of the people depicted.
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The mid-afternoon California sun poured into the window in CaCee's office as we sat together on her plush new sofa. She had finally decorated the office and just spent fifteen minutes walking me through all the choices she'd made in the process. But now she was down to business, telling me about our latest client. "Soooo, my little Leenie, I've got a new one for you. A little different, but from what you've told me in the past, I don't think you'll have any problem with her." I wondered what she meant by "different". I'd been at this now for a several months and had seen a number of clients, most of them famous, all of them rich, Hollywood women. Some (most, really) had been pretty self-centered and spoiled, but none had been nasty or kinky. I wondered if that was what was coming.
CaCee rambled on as thought back to how this all started, several months ago. CaCee called me with what seemed like a crazy idea - to become a "lesbian call girl" under her management. CaCee knew of my sexual proclivities from my time as a summer intern for her and her best friend (and then her boss) Jessica Simpson, when, through an odd series of events, I ended up spending a lot of "quality time" with both of them. Those activities, however, were a far cry from prostitution, which is really what CaCee was proposing. She argued that it would all be very high class and safe, with rich and famous clients in the entertainment business, and that, from her own experience, I would be great at it. And she assured me there was a market for this, plenty of high-profile women, many of them older, who would pay for it, either for a special thrill, or for easy access to an attractive young girl, or just to satisfy their needs in a discrete, no-strings-attached environment. But there was no escaping the reality of the job, so my first reaction was an emphatic "Hell no." However, after I got over the initial shock and thought more about it, I reconsidered. CaCee was she was talking about big money, which I could certainly use. And adding in the adventure and the beautiful women she assured me I'd be with, I decided to give it a try. CaCee was thrilled, as she had just quit as Jessica's assistant and needed the income herself. She had been keeping me busy ever since.
I came out of my reverie and realized that CaCee was still talking about our latest client. "I know you say you like older women, hon, but this one's older than any of the others." That did catch my attention. Yes, older women interested me, and I'd been with several "older" women already, but that was relative to my own age. The oldest so far was close to forty, which isn't really old at all. CaCee's cautious comments made me wonder where this was going.
It was time to cut to the chase. "So what's the story, CaCee," I asked. "Who's the client?"
CaCee answered my question with one of her own: "Do you ever watch 'Desperate Housewives'?"
"Hmmm,.. No," I said, "I watched it the first year, but only off and on since. It got kind of silly." As I spoke, I was leafing through the cast in my mind, wondering who this mystery woman might be. The big stars were all close to forty, and still very attractive, but there were a few bit players who were much older. I wasn't sure how I felt about that - it could be a little strange. On the other hand, this was a job, and I knew things could go this way when CaCee first proposed it to me.
"Well," CaCee continued, "if you haven't watched recently, you may not know our latest 'adventurer'. Are you familiar with Dana Delaney?"
Omigod, I thought - Dana Delaney! Yes, I was familiar with her. In fact, I'd had a girl-crush on her for years. In my early teens, watching reruns of "China Beach" on cable, my response to Dana was one of the first indications of the direction of my budding sexuality. I had seen her in a few more recent things, but had yet to see her on "Desperate Housewives". I was surprised to hear her spoken of as "old".
Snapping back to the present, I answered CaCee's question. "Yeah, I know her. But she's not really that old, is she?"
"Not sure of her age, but I know she's over fifty. That better be okay, babe, because I already committed you. I told you at the start that you wouldn't always be with hot little sexpots. Plus, it's a good deal - all day, and she's paying a premium for it."
"Sure, it's fine," I assured her, and I meant it. I realized that I hadn't seen Dana in anything recently, and that she was already in her thirties when I first noticed her, but it was still hard to believe that she was fifty. I assumed she had stayed in shape, but I wondered what she looked like these days. Our age difference was considerable, but on the positive side, that could add extra excitement, a little extra kink to the encounter.
"Cool," she said, beaming proudly at me, her little project, "You're so easy to work with. Now where were those notes I had on this?" CaCee moved to her desk and rummaged through the piles of papers she had there. As she bent over the desk, I admired her lovely backside, so perfect there in her tight pink capris. Her halter-top shifted up to expose a long expanse of smooth, tan skin on her back. I felt myself responding to the sight and realized that it had been a while since I'd had any sex. But that was about to change.
We stood together by the desk as CaCee filled me in on the details - where I was to go, what time, as well as a cover story for why I was there, in case it was needed. And she reiterated that Dana had paid for the whole day, which meant, in theory at least, that she could have me until the following morning, almost twenty-four hours. I'd never made that long a commitment, but as CaCee noted, she had paid extra for it.
I was about to go, but as I turned for the door, CaCee placed a hand on my shoulder to stop me. "Oh, yeah, Milene, I almost forgot... Jess wants to see you tonight." Then she added with a roll of her eyes, "I think she's feeling 'needy'."
I had to laugh at that. Part of the deal with CaCee was that I would continue to service Jessica whenever she wanted it, so I knew what that "needy" meant. It meant two or three hours parked between Jessica's legs, eating her pussy and ass until she had more orgasms than most people could even think about. And of course, Jessica just took them for granted, as something she was naturally entitled to. I didn't mind, though. Even after so many times with her, I still enjoyed Jessica's luscious body, and I really loved her insatiability and the way she responded to my lovemaking. It would be a fun night.
