A Man and his Faults

I set out to write a story about a man with a shoe fetish, but as I wrote I became more interested in the character and the things he values: great legs in nylons and heels, good whiskey, fine cigars, illicit sex, and, above all, making money. It morphed into more of a character sketch. Sometimes the story just takes control. Please feel free to leave comments.

All characters in this story are over the age of 18.

It's a lovely fall day in Northern California. I'm sitting on the little deck at the back of my houseboat in Sausalito enjoying a fine Cuban cigar and a glass of 20 year old Lagavulin Scotch whisky. I'm also enjoying the second year following my most recent divorce (number three if my memory is correct). Divorces are an acquired taste. Each one is different and it takes a bit of time (months at least) for your most recent divorce to settle in and let you appreciate just how much better off you are.

They are all expensive of course. But what fine things aren't. This Cuban cigar and the glass of Lagavulin I'm enjoying didn't come cheap, and the rent on this houseboat is exorbitant compared to what you would pay on a square foot basis for a home in a cookie cutter subdivision (Ugh!). And the cost of the most recent divorce--more money than I ever thought I would have when I was 18.

The Lagavulin can be purchased at any quality liquor store, but if you want the twenty year old, be prepared to pay up. Enough said.

The Cubans are a bit more complex since it is against the law to bring them into the country. Now that my long term marijuana supplier's business model has been destroyed by the legalization of recreational marijuana, he has had to find something else illegal to sell. His view is that if the product is clearly illegal there are no pesky and expensive taxes to pay and regulations to comply with. Minimizes overhead, improves return on sales, and simplifies his life. He has always specialized in selling to folks with enough money so they didn't quibble about his prices and were unlikely to get themselves in trouble utilizing his products (he avoids the Hollywood types who are notoriously unstable). With his main product suddenly legalized he has simply found other lines of illegal merchandise that the well-off are willing to pay-up for. He tells me that his business in Cuban cigars is quite good. I'm careful not to ask what else he deals in.

And the houseboat you might ask? I waited in line for four years to get this houseboat lease. I could see my third divorce coming and I was positioning myself for something new and different. Something that my now ex-wife wouldn't view as an asset she wanted part of. Rumor has it that the notorious early Twentieth century Madame, Sally Stanford lived on this boat, but I doubt that. Still the neighborhood has a lot of history, much of it scandalous and undocumented. I love it.

And a divorce? The price of a divorce is always just a bit more than you think you can afford--until you consider the pain and suffering involved in continuing a bad marriage. Then you tell your lawyer to pay up and get it done.

As I sit here in the midday sun south looking across the Bay at San Francisco I ask myself why I ever got married. My ex-wives have cost me a fortune in alimony and property settlements, including three very nice homes, one in Atherton, one on Green Street in the Pacific Heights portion of the City, and one particularly nice home in nearby Mill Valley. My little houseboat in Sausalito is not nearly as grand as any of those edifices, but it is quite comfortable and not nearly as expensive to maintain as those homes were. Not to mention the maintenance expense for each of the wives who shared those homes with me. I seem to have a real skill for picking high maintenance women to marry.

So why haven't I been able to stay married? I know lots of people who stay married for years even decades; happily married at that. Good question. I pull on the cigar and savor it and follow it with a sip of this lovely Scotch. I can't answer the question with any certainty, but a few things come to mind.

First, I'm convinced that I'm just not cut out for monogamy. Of course none of my ex-wives seemed to be very inclined that way either, so I can't say my tendency to wander was really the cause of the failure of any of my marriages. My ex-wives did have a bit of a problem with falling in love with and wanting to marry their lovers--a problem I never have. For me a fling is just a fling. Something to be enjoyed, even savored, but not a long term thing. A bit like a truly fine cigar, I think as I draw on the Cuban again. But of course a good fling lasts longer than the life of a good cigar, but perhaps not nearly so long as a couple of boxes of good cigars. And then of course there were always the quickies. I smile as I think how many of them didn't last as long as a single good cigar, but were none-the-less very satisfying.

In addition, as all of my wives were quick to point out, I am obsessed with work. I have to acknowledge the truth of that. I'm in the finance business, venture capital to be more specific, and it has been very profitable. I'm the Managing Partner of my own firm now, but getting there required a lot of work including a lot of time spent flying around the country finding potential portfolio companies to invest in (the eternal search for the 'next big thing'), wooing investors in my firm's various funds (ultimately this business is built on what we call OPM (Other People's Money)), engineering the liquidation of portfolio companies (IPOs, sales, and I'm sad to say occasionally bankruptcy followed by asset liquidation. Not everything is a winner). I confess to having left my wives to their own devices far too much. But care and feeding of a growing company and a needy wife sometimes (perhaps always?) add up to more than a full time job, and my bias was to put the company first--an economically sound decision as the money I've made in the venture capital business far exceeds the cost of all three of my divorces combined. As I approach middle age I have occasionally asked myself if I should ease back on the throttle at work, let some of the younger guys carry the load. But then what's the fun in that, especially now that I'm again single? I love my job. The only thing I can say I enjoy more is sex with women I'm not supposed to be with.

And I'm not going to go into any detail about any of my ex-wives. I believe there are mutual non-disparagement clauses in each of my settlement agreements. Those plus the size of the property settlements were intended to preclude tell all books. After all I do have a reputation to maintain and so do they. What's past is past and should stay that way. Besides I think you would find my history of obsessive sexual conduct far more interesting:

My Obsessions

There is no point in telling you about the details of my obsessive business life. It would just bore you, unless you happen to be one of my competitors or involved in the finance business in some other way. We will skip that. Suffice it to say, I've been more than a little obsessed by it, frequently to the detriment of my relationships with others.

But I will confess to being a bit obsessed about sex and that makes for much more interesting discussion:

As I approach middle age I've been wondering: Do I have a stocking fetish? I like to tell myself that if I have one, it's not very extreme. I'm not a guy who gets off on sniffing a woman's smelly shoes or her well used stockings. I've tried sucking a woman's toes a couple of times, but it was usually in a bath tub. It mostly resulted in a lot of marijuana fueled laughing and giggling. But still--nothing will distract me, even obsess me, like a woman's legs displayed in sheer nylons combined with a killer set of high heels. And if that is all she has on below the waist, all the better. They can be thigh highs, garter assisted or not, or even panty hose. Any of those combined with heels will get me going. And where I go from there usually depends on the woman and where she wants, or is willing, to go.

I think I've had this obsession (and yes, I admit it's an obsession) ever since I was eighteen. My mother re-married that year and I discovered a trove of sex magazines hidden beneath my new step-father's bed. I don't want to claim my step-dad was kinky. His mags seemed to cover a full range of sex acts--naked women; sexy lingerie (yeah, even men in sexy lingerie); large cocks; masturbation (male, female, and mutual), oral sex (cock sucking and cunnilingus); lesbian sex; gay sex; anal sex; group sex; interracial sex; BDSM; creative uses of sex toys; and, most important to me, women in nylons--thigh highs, with and without garters, panty hose, often with the crotch torn out, and tall heels in combination with any of the foregoing; and then of course there were the scenes in which nylon clad feet were masturbating a rigid erect cock. It went on and on. My new step-dad had a lot of magazines.

Given the wide variety of smut under my parents' bed I couldn't reach any conclusions about whether my step-dad had specific preferences or not. As near as I could tell he just liked sex. Pretty healthy. As I got older I wondered whether the smut under the bed was just his, or was it his and Mom's joint collection? I mean, why should I assume my step-dad was the only perv in the family? I know they had a healthy sex life (Mom was loud). But, I wasn't about to have a chat with either of them about who owned, and who enjoyed, the smut beneath their bed. I was just thankful it was there and I could peruse it when they were away. It was the lending library that I used to supplement the woefully inadequate sex education classes I had received when I was younger. The important thing to understand is that by the time I went away to college at the end of that summer I knew the hosiery pictures and the high heels were a turn on. Why? Who the fuck knew? Just the way I was wired I decided. I've never stressed over it.

Now you shouldn't get the idea that I was obsessed with my little kink about nylons and heels to the extent that it interfered with developing a reasonably normal range of other male sex interests. To put it bluntly, I was a horny young fellow in college. I got it whenever and however I could and took care of myself regularly when I didn't have a partner. I even tried gay sex a time or two, but it never really turned my crank. I did thoroughly enjoy watching women go to it the few times I had the opportunity. Pretty normal I thought. Just like my step-dad.

I also paid attention to my studies and did well in college and in the MBA program I went on to. In college and graduate school there wasn't a lot of opportunity to pursue my little fetish with real women. Standard collegiate dress where I went to school was pretty much jeans and a T-shirt. Maybe if I had gone to Harvard it would have been different, but the climate is so much better at Stanford. I had relationships with a couple of women during graduate school that I tried to convince to accommodate my fetish, and while they were happy to fuck my brains out on a regular basis in pretty much every position we could bend ourselves into, I could never convince them to indulge my kink.

Things got better once I entered the business world. I'm not old enough to have experienced the 50's and 60's when all men wore suits and ties and all women wore dresses, heels and panty hose, which most of the men felt free to try to talk them out of any time the urge struck them. But when I started in the finance business the first thing I noticed, beside the fact that the banks weren't hiring anywhere near the number of women who were coming out of the MBA programs, was that jeans and T-shirts were not the standard dress. Women wore dresses and the ones who were above the administrative assistant level wore women's business suits (dark blue pencil skirt stopping at some level above the knee; white blouse (with or without what we used to call a blow lunch tie); dark blue blazer; and of course killer heels). And nylons? Well that seemed to be optional, but when a woman opted in for hosiery, I noticed, whatever her rank in the organization. It could be quite distracting.

A Quickie

Quickie's are an interesting concept. You never know when they are going to happen, but when the opportunity arises you should take advantage of it. They are always 'here today, gone tomorrow' opportunities, and they almost always involve sex with a person who shouldn't be screwing with you (neighbor's wife, boss' secretary or even better his daughter home from college, current or past sister-in-law, current or ex-wife's best friend, etc.) or, at least, in a place where the two of you shouldn't be doing it (master bedroom at someone's Christmas Party, office (yours or hers), behind the bushes in the front yard with a horny mail delivery lady, etc.). When you decide to pass up an opportunity for a quickie you may find yourself regretting it for days as your imagination keeps reminding you of how hot the sex you passed up would have been. But since it never happened, you can't convince yourself you didn't miss anything. I'm inherently an optimist.

One of the more memorable quickies of my life was with Melinda, a senior partner of a major Wall Street Bank.

Melinda

My first real experience with making love with a woman in nylons and heels came a year or so after I finished college and joined a major Wall Street Investment Bank. By that time the Wall Street banks had suffered major title inflation. I was a lowly Associate which translates to 'do what I tell you and get it done by tomorrow first thing even if you have to flog that spread sheet all night.' Fair enough. I understood what I was signing up for when I took the job. The next level above we lowly Associates were the Vice Presidents. Sounds like a big title, an important job. Not really. It just meant you had survived a couple of years as an Associate without screwing up bad enough to get fired and, more importantly, that you might now have a couple of Associates of your own to lord it over. Above the Vice Presidents came the Directors (with, depending on the bank, a variety of title qualifiers such as Assistant, Deputy, etc.) It was best to be a straight 'Director' with perhaps a specific portfolio of responsibilities attached to the title (e.g., Director, Leveraged Finance), except of course in an organization that had implemented that august title, 'Managing Director.' Then, of course, there were the 'Partners.' They were, if not actual gods, people who sat at the right hand of god and should be treated as such, if they ever deigned to speak to you. It was rare that a Partner spoke to a lowly first year Associate. They would even delegate your ass chewing if you did something wrong.

Around the middle of my second year as an Associate I had a quickie with an honest to god Partner. It was also my first real hands on experience with a woman in sexy heels and nylons. Prior to that my experience had always been one of lusting after hosiery clad women I saw in the office or elsewhere and of course in the various porn sources I utilized. But this experience was real--so much better than my imagination or the efforts of the porn merchants.

I was working on a project for a major Silicon Valley firm. Our client firm was seeking to borrow $1.5 Billion from a consortium of banks led by one of the major Wall Street banks. It was about two in the morning and as far as I knew everyone in the building had gone home for the night. I was sitting by myself in a conference room in front of a lap top flogging away at a spread sheet in an effort to squeeze out a semi-optimistic forecast of the client firm's future performance in a downside scenario. Would be lenders always want to know what is going to happen in the worst scenarios they can imagine. Then, if the borrower still is forecast to remain solvent, they want to see another case that is one step worse.

I heard the door to the conference room open and I looked over my shoulder to see an honest to god Partner of our firm walk in. A Partner at two o'clock in the morning? And this wasn't just any Partner. This was Melinda Gibson, one of the only three women Partners in the firm and a member of Partners' Executive Committee which undoubtedly made her the most powerful woman in the firm.

"Hello Rodney. How is the model coming?"

Shit, I thought. She actually knows my name. How did that occur? I'd never met her before. Hell I'd never met anyone who had met her. The only reason I recognized her was that I had seen her head shot in the Bank's annual report.

"It's coming along," I responded. "I'm just about to wrap it up and e-mail a copy to Ralph."

"Who?" she asked.

"Ralph Bildough," I responded. "He's the Vice President I work for."

"Oh yes, Ralph," she said.

Not wanting to look directly into the eyes of a god for fear of having my own vision incinerated, I kept my back to her, my hands on the keyboard and my eyes glued to the screen. But I could hear her heels clicking as she walked across the hard floor towards me. It was the sound of impending doom. Then without warning she was sitting on the table right next to my lap top facing me. There was no hope of keeping my eyes from her now, but they weren't on her face. My vision was locked onto just about the longest, sexiest, pair of legs I had ever seen. As she hopped up on the table her dark blue pencil skirt (even the gods wore the uniform) had pulled up to the middle of her thighs. Her legs hung over the edge of the table with one leg crossed over the other, and she was leaning back on her hands, her blue blazer hanging open and her breasts standing out beneath her white blouse. But what really had my attention nailed, just riveted, were the sheer black stockings and the pair of gleaming black Jimmy Choo pumps she wore. Her legs and feet were without doubt the sexiest thing I had ever seen. The pictures in the mags under my parents bed were trivial by comparison.

Before she walked into the room sex was the farthest thing from my mind. I was sharply focused on how to squeeze a profit (or at least enough pre-tax cash flow to service debt) out of my financial model of the client firm under the absurd downside economic assumptions the lender was insisting on. But all that disappeared from my thoughts as I stared at her nylon clad legs and sexy pumps. I could feel my cock rapidly growing and raising a lump in my trousers. Fuck she was hot!

"I don't believe we've met Rodney, but I'm Melinda Gibson." I realized she was reaching forward with her hand offering me a handshake, so with great reluctance I tore my eyes away from her legs and feet and took her hand. I could see the details of her bra beneath the sheer white blouse she wore. The bra was enclosing a good sized pair of jugs which I noticed with minimal erotic effect given my obsession with her legs. I dragged my vision farther up until I was looking at her face. Melinda was in her mid-forties and very well preserved, with long dark hair tied in a knot behind her head. Her makeup emphasized her high cheek bones and her large brown eyes. Her lipstick was a bright red that looked recently refreshed.

We shook hands and each leaned back a bit. I watched her face long enough to realize that she was not staring at mine. Her vision had drifted downward so she was staring at my crotch and the rapidly growing lump in my trousers. But then who was I to complain. My focus likewise quickly reverted to her incredibly sexy legs.

We chatted a bit about my financial model and the deal. She asked me a number of questions about my model which surprised me a bit in the depth of knowledge about the client firm they disclosed. I guess you don't get to be a Partner without doing the work. She may not have known who the Vice President I worked for was, but she knew a hell of a lot about the client firm. But the whole discussion of the client firm, the deal, and my financial model was simply a thin cover for what was really going on in the room. Every minute or two Melinda would rock back a bit on the table and un-cross and re-cross her long legs, letting her skirt slide up just a bit each time and giving me a peak between her thighs. I didn't see her panties, but after about the third adjustment I was sure I had seen a flash of the creamy skin of her inner thigh above the top of her nylons and the straps descending from the garter belt ensuring the stockings stayed stretched tight, smooth, and sexy. Meanwhile my dick had reached full erection status and I was forced to take my hands off the keyboard and the mouse for a brief effort to adjust my trousers. I looked up at her face as I did it and saw her lick her lips, her eyes glued to my hands adjusting the crotch of my trousers. Busted, I thought, and Melinda is clearly interested in something more than just the financing project.