Planning Ahead


Disclaimer: This is an erotic story, however your mileage may vary. You must be 18 years or older to read this story, be able to read erotica in your community and not be offended by the contents of it. If you are not at least 18, live in an overly repressed community, or are easily offended, move on. This is not for you.

This story is fiction and as such is protected under the first amendment. The people referred to in this story do not behave this way in real life, this is a fantasy and any resemblance to real people or situations is merely a coincidence. Any copyrighted names, works, etc. remain property of their respective owner(s).

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And now the story -

* * * * * * * * *

The life of a financial planner is generally not an overly exciting one. Sure, if you don't really know what a financial planner does you might be willing to believe that it's exciting and glamorous, especially if your clientele includes some of Hollywood's A-list and many young hope-to-be's. But trust me, Bruce Willis and Tom Cruise won't be playing me in any bio-pics anytime soon. My life is far less that of a super-cop or international spy and more that of a glorified CPA. Minus the really nifty pocket-protectors accountants seem to have co-opted from the IT guys of course.

Take that part about Hollywood A-listers and rising young stars. Sounds glamorous right? Get to meet with George Clooney and Brad Pitt, schmooze with Sandy Bullock and Sarah Michelle Gellar. Offer stock tips to Jennifer Garner. Right? Wrong. Try meet with the business managers, schmooze with the assistants and give stock tips to the relatives with all the financial acumen of a tree stump.

For instance, the other day I had my quarterly meeting scheduled with Shannen Doherty. I'd been her financial planner for some years now and it was time to get together to discuss her portfolio. What to buy and what to drop, what real estate holdings were newly available in her market and how her existing holdings were performing, her income and projected growth and what's in store for her when the casting directors are no longer calling. Not exactly the most exciting topics on earth, particularly if, like me, you do it all day long, every day, year after year. And it's even less thrilling if you're used to the glitz and glamour of a Hollywood lifestyle. So was I excited about my meeting with Shannen? About being face to face with an incredibly hot young actress? Of course not. Shannen wouldn't be coming within a mile of my office. The only thing I was going to be face to face with that afternoon was her business managers, two guys far older and even more stuffy than I was. And they cared about just one thing. Was I increasing Shannen's net worth? If so, then they were happy. Deliriously so. The more it increased the better since their compensation was tied in to her total income. So, while the meeting was going to be a lengthy one, lasting almost all afternoon, it certainly didn't promise to be an exciting one. Unless your idea of excitement is watching dough rise.

Which sort of explains why I felt safe doing what I did before the meeting.

Let me explain.

See, I'm the kind of guy who has long-term relationships with women. I'm not a serial dater, at least not the way one usually defines serial dater. I go out with a woman and more often than not it develops into a relationship that can last for quite some time. And if, or when as has been the case every time up to now, it eventually comes to an end, I wait awhile and meet someone else and another relationship begins. That's how it's always been. It's kind of like a routine for me. Habitual. Stable. Predictable. Tedious.

So, as expected, my last fling ended, some eight months ago, and for some reason, this time, after I got over feeling sad about the demise of one more relationship, I was unable to get into the frame of mind I needed to allow me to move on and begin something new. I just wasn't very interested in meeting women. I found the whole thing... boring. Much like I was finding everything else in my life at the time. Boring. Now in and of itself it's not such a huge problem to be a little tired of the whole dating ritual, except... I was horny. Very, very horny.

And horniness, as I bet you can imagine, is a great motivator. Having the ability to do everything from getting teenage boys to comb their hair and brush their teeth through getting grown men to sit and watch The English Patient on up to being the underlying reason for countless wars. Sure, the books all say it was 'for the love of a woman' but that's just code for the guy wasn't getting any and he was horny and he thought that if he just, pick one of the above, the girl would give it up. Sometimes it even works and that just reinforces the belief in horny men everywhere. If I just do this, maybe she'll have sex with me. And so it was for me too. It was horniness that finally forced me back out there and, against the better judgment of every man on the planet, I found myself being set up on a blind date with a co-worker of the wife of one of my best friends. Yes, I know, that was pretty dumb of me. But I was horny, remember?

The first date went okay, and for some not so inexplicable reason I agreed to a second, and that went okay too, as did the third and the fourth and before I knew it I found myself slipping down the slope into yet another relationship, complete with a weekend in the wine country for two. What does any of this have to do with my meeting with Shannen's people you ask? Don't worry, I'm getting there. So anyway, my meeting with Shannen's representatives was on Friday afternoon, my last appointment before the weekend. After the meeting I was supposed to meet my new lady friend and we were going to drive up the coast to a bed and breakfast. As you might expect if you were going to spend two days away with someone, I assumed we were going to have sex at some point during the weekend. Just one tiny problem though, the prospect did not excite me. I mean, the thought of finally having sex after having gone so long without thrilled me, but not the person I was going to be with. She didn't really do it for me. Not at all. Don't get me wrong, she was attractive enough. I guess. Just not to me. So why did I agree to go away with her for the weekend? Did you get the part about how horny I was?

Anyway, I was going to be alone with this woman and I knew one of us was probably going to make some sort of move and, in spite of the fact that it was an overwhelming feeling of horniness that had gotten me into this in the first place, I still had my doubts about my... response if and when the time finally arrived. Would my ambivalence about the situation leave me so turned off that I couldn't even get it up? Or would the eight long, long months without sex make it so that it didn't matter how little attraction I felt towards her, I would be raring to go. So raring that it might even all be over before it started. I just didn't know. And neither possibility was particularly appealing to me. I know, I should have just canceled the whole thing and said my goodbyes and gone home to watch some porn, but I didn't. Instead I came up with a plan. It's what I do, as you might have guessed from my job title. I plan. And my plan called for me to see a doctor about a prescription for a little performance boost. You know, something that -- cut to tremendously sexy woman clad only in a man's dress shirt -- improves the 'quality of the experience'. I figured that this way I was covered no matter how I responded. If I was having trouble getting in the mood, presto, chemically induced hardon, and if I was a little too eager, well, presto, chemically induced second hardon. See. I was covered. Of course I didn't explain all this to the doctor, I just gave him the usual song and dance about how my erections were no longer as satisfactory as they used to be. Job related stress I offered. Not that I think the doctor really cared why I wanted the pills, he just wanted to push his drug of choice, but I didn't want him to think there was anything permanently wrong with me. The male ego really is a fragile thing where some subjects are concerned. So anyway, I told my sob story, the doctor bought it and twenty minutes later I was on my way back to my office with a sample pack of Cialis in my pocket and a prescription for a two week supply.

So I went to a doctor to get some pills for erectile dysfunction, what's the big deal you ask? Well, if it had ended there then I suppose it wouldn't be anything to get worked up over, but it didn't end there. That was really just the beginning. Because after I got back to my office I did something that seemed harmless at the time, but could have had the potential to destroy my entire career. I took one of the samples. The 20mg pill. The strongest dosage they make. Yes, I can be exactly that stupid. Now do you see the big deal?

Of course I didn't really see any problem at the time. The doctor had told me that the pill would remain in my system for up to 36 hours and I would not have any reaction until I was sexually stimulated. Well I don't know about you but I've never been sexually stimulated during a business meeting with two old men. Guess I'm just old fashioned that way. So I felt perfectly safe taking the pill a half hour or so before the meeting was scheduled to start. I took it partly because I didn't want to have to stop to pop a pill after things had already started with my lady friend, and partly because it felt, naughty. You know what I mean. Knowing that this drug was in my system just waiting for the right moment to be triggered while I sat through a monotonous business meeting with two clueless codgers made me feel, somehow less dull. Less like I was trapped in a never-ending rut. Less like a puffed up accounting clerk. Less boring. I know, I know, odds were both of the old coots popped Viagra like breath mints and wouldn't be at all shocked to find out I was taking something similar, but I wasn't thinking about that. All I could think about was that I had done something completely out of character for me. Something different. Something not boring.

Now here's where it gets interesting.

They never showed up. No phone call, no e-mail. Nothing.

Is that unusual you ask? Hell yeah! This was a meeting about money, and if there is one thing I've learned in my time in financial planning, it's that there is nothing on earth fat, old men like talking about more than money. Forget expensive cars, fine wines, Cuban cigars or hot trophy wives. These guys really, really like to talk about money. How much they have, how much they made, how much they're going to make. Even when, technically speaking, it's not theirs, they still want to talk about it. They love it, it's like a drug to them. So for a couple of guys to not show up to a meeting to get their fix, yeah, that's pretty unusual.

So I waited.

Ten minutes turned into twenty then thirty and then, after about forty minutes, just as I was about to give up and take off for the day, I heard someone approaching my office door. Finally. I stood up to greet them as they entered, fixing a smile to my face and getting ready to pretend that I wasn't at all put out that they were over half an hour late and hadn't even bothered to call. The door opened and I started to speak before they were even in the room.

"Ah, good. You made it. I was beginning to get wor... Shannen! I mean Ms. Doherty. How nice to see you!"

"It's nice to see you too. Sorry I'm late. My lunch meeting ran longer than expected. And please, call me Shannen. We've known each other too long for you to call me Ms. Doherty."

She closed the door behind her and approached my desk as I stepped out from behind it to greet her. I held out my hand and she took it in both of hers, shaking it warmly and holding onto it for a few seconds. When she let go I looked over her shoulder to see if perhaps her missing associates were coming in behind her.

"Shannen it is then. And will your managers be joining us?"

"Frick and Frack? I fired their fat asses. They were getting too greedy and they cost me two shows and a movie deal. So they're gone. I'll be handling my own business affairs for the foreseeable future."

"Ah. Well. Sounds like a prudent move. I'm sure you'll do just fine. Please, why don't you take a seat."

I gestured her to one of the chairs that faced my desk and she took a seat, adjusting her skirt as she sat down before crossing her legs while I perched on the corner of my desk. We made some small talk for a short time, catching up on recent events that had occurred since the last time Shannen and I had seen each other. Actually Shannen did most of the catching up, my small talk being somewhat smaller than usual, due to the fact that I was far more interested in checking out Shannen's incredible legs than I was in chitchat. Surreptitiously of course. It would never do for me to be obvious about ogling a client's goodies.

Say what you will about Shannen, in my opinion she is one of the most beautiful women in Hollywood. As for her anger issues, I can only say that she's never been anything but nice to me. Still, I've heard some of the stories naturally, she comes across as being something of a terror when angry and I'd rather not find myself on the receiving end of her displeasure, even if she is only 5'3". When it comes to volatile women I find that discretion is the better part of keeping your gonads unharmed. So I was being very careful as I gaped at Shannen's legs.

I mentioned before that she was wearing a skirt, but I did not say what kind of skirt it was. Or how short it was. Almost scandalously so. And her top. I guess it wouldn't be considered too revealing, if you didn't notice the deeply scooped neckline and the square yards of cleavage it revealed. What's that? You think that's inappropriate attire for a business meeting? Maybe for New York, but this is Hollywood and Shannen is one of the beautiful people and is expected to dress a certain way. And whatever you may think of her looks or her disposition, there is one thing that I believe cannot be disputed, the woman knows how to dress to kill. Her choice in apparel was no less appropriate for a business meeting in L.A. than my own short-sleeved knit shirt and Dockers. Hell, at least we both were wearing shoes and not wearing sunglasses and believe me I've been in many meetings where participants did just the opposite. And these meetings were not taking place outside by a pool.

But I'm getting off track here. The point is, Shannen was dressed to thrill and while she sat there filling me in on her horses and dogs and her new pickup truck, I sat there scoping out her legs. Among other things. Which wasn't a problem as long as I at least made the appearance of keeping up my side of the conversation. Something that I was doing without any problem. Until Shannen leaned forward in her seat and her top billowed out from her chest and that combined with my elevated position gave me an excellent view down her blouse and the yards of exposure became acres.

That was the beginning of my trouble.

"... and that's when I found out I'd been dropped from consideration for the role. All because those jerkoffs priced me out of the producer's range."

"Fantastic. That's... fantastic."

When I realized that Shannen was no longer speaking I finally tore my eyes away from her chest and focused fully on what she had been saying. She had been telling me about how her former business managers had screwed up her chances for a plum role in Kevin Smith's next movie and I had answered... Oh Shit!

Embarrassment colored my cheeks at my verbal gaffe and I looked at Shannen only to see her peering at me with the beginnings of a frown on her face. I didn't even know how to start apologizing for my blunder so I opted to ignore it, instead suggesting that we get down to the reason she was there in the first place. I pointed to the small conference table by the windows and began to move in that direction. After a second's hesitation Shannen moved to join me and as she started to rise she glanced down and apparently noticed for the first time just how much of her chest was on display. When she looked back up the frown was gone and she caught my eye and gave me a knowing smirk, the brief smile conveying all too clearly that she now knew exactly what I had been staring at and why I had responded so strangely to her last statement. I was surprised at first that her reaction to my peeping wasn't stronger, but then I guess it stands to reason. Women do not dress the way Shannen was if they don't want to be looked at. Look, but do not touch.

We moved over to the round table and Shannen took a seat across from me and we started to go over her portfolio. Many of the things in it she was hearing about in detail for the very first time, her former managers not having been very interested in passing on the specifics. When I started to review her real estate holdings she sat there in wide-eyed wonder as she listened to me list all the places she had some sort of stake in.

"So you're saying I own a car wash?"

"Yes, in Yonkers, New York. A piece of it anyway, about 7%"

"And a donut shop?"

"In Duluth, Minnesota. 10% of that."

"And all these other things as well?"

"A Laundromat, a bakery, two small apartment buildings, yep you have a share in them all. Plus your stocks, treasury notes, muni's and the mutual funds you're in."

"Shouldn't we be considering selling the apartment buildings? Isn't the real estate bubble going to burst soon?"

"For private and two family homes, yes. It can't keep going up indefinitely without some sort of major adjustment. But rental units are in short supply in most metropolitan areas and remain a sound holding."

"Oh Okay. And what about Charmed? I still own a piece of Charmed, right?"

"Oh yeah. I wouldn't dump that just as the early seasons are coming out on DVD. That triggers the bonus clause and you go up to 10% from 5%. Should mean enough for that vacation home in Hawaii you were talking about."

Her voice took on a teasing note as she responded "Oh so you heard that did you? And here I thought you weren't paying any attention to me. Well, to what I was saying anyway."

Once again I flushed in embarrassment at having been caught looking down Shannen's shirt, but as I had the first time, I simply ignored it and tried to move on to discussing future acquisitions that I thought we should pursue. Shannen accepted the change of subject easily, but the small smile that remained on her lips told me she was having some fun teasing me about my wandering eyes.

Unfortunately that small reminder got me thinking about the ripe melons that were barely concealed under her top and I soon found myself sneaking quick glances at Shannen's chest again whenever I thought she wouldn't notice. I knew I shouldn't be doing that, it isn't exactly what I would consider professional, but I was powerless to resist. I really was very, very horny.

Up to this point I'd been enjoying the meeting with Shannen more than any other get-together I'd had for a long time. It was nice to actually sit down with the person on whose behalf I'd been making all these arrangements for the past several years, instead of with some proxies. And it was even nicer to be spending time with such a beautiful woman, especially one who was so ridiculously hot, sitting there in a micro-mini and low-cut top and giving me tantalizing glimpses of one of the most perfect sets of tits I'd ever seen. I was having fun and I'd been able to put my weekend dilemma completely out of my mind for a while. I was feeling, not exactly calm - I was still way too much on edge for the word calm to be used in regards to my emotional state -- more like, content, with my situation for the first time in weeks.

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